AU674948B2 - Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them - Google Patents
Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them Download PDFInfo
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- AU674948B2 AU674948B2 AU65034/94A AU6503494A AU674948B2 AU 674948 B2 AU674948 B2 AU 674948B2 AU 65034/94 A AU65034/94 A AU 65034/94A AU 6503494 A AU6503494 A AU 6503494A AU 674948 B2 AU674948 B2 AU 674948B2
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- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- C07C255/65—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
- C07C255/66—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms having cyano groups and nitrogen atoms being part of hydrazine or hydrazone groups bound to the same carbon skeleton
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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
0050/43960 Imino-substituted phenylacetamides, their preparation and fungicides containing them Description The present invention relates to substituted phenylacetamides of the formula I where the substituents have the following meanings:
Y
is oxygen or the group NR 6
Z
1 and Z 2 are independently of one another hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, cyano or nitro; is hydrogen, alkyl, haloalkyl or aryl; is hydrogen, or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heteroarylalkyl, heterocyclyl, cycloalkenyl, arylalkyl, aryl, heteroaryl, arylalkenyl, heteroarylalkenyl, aryloxyalkyl, heteroaryloxyalkyl, acyl, arylcarbonyl, heteroarylcarbonyl or alkoxycarbonyl;
R
3
R
4
R
5 and R 6 are independently of one another hydrogen or alkyl; or R 6 and R 2 together with the nitrogen whose substituents they are, can be a ring.
0050/43960 2 The invention additionally relates to processes and intermediates for preparing these compounds.
It has been disclosed to use imino-substituted phenylacetic acid derivatives as fungicides (EP 499 823). However, their action is unsatisfactory in many cases.
An object of the present invention is therefore compounds having improved action and an increased spectrum of action.
We have now found the compounds I defined at the beginning.
We have additionally found that compounds of the formula I have a good insecticidal, nematicidal and acaricidal action. The fungicidal action is preferred.
With respect to their biological effectiveness for the control of harmful fungi, suitable compounds I are those in which the substituents have eg. the following meanings: Z' and Z 2 are hydrogen, halogen such as fluorine, chlorine, bromine and iodine or eg. methyl, methoxy, cyano and nitro;
R
3
R
4
R
5 and R 6 are hydrogen
C
1
-C
6 -alkyl 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-methylphenyl, 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; R1 is hydrogen
C
1
-C
4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
4 -haloalkyl, particularly C 1
-C
2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 0050/43 960 3 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-trichioroethyl and pentafluoroethyl; unsubstituted or substituted aryl such as phenyl, naphthyl and anthryl, preferably phenyl and naphthyl, in particular phenyl; is hydrogen; Cl-C 4 -alkyl as mentioned above; unsubstituted or substituted
C
3
-C
1 5 -alkenyl, particularly C3-C 6 -alkenyl 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, 4-hexenyl, 5-hexenyl, l-methyl-2-pentenyl, 2-methyl--2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2--pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2, 2-dimethyl-3-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-direthyl-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, 1-ethyl-l-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl; unsubstituted or substituted C 3
-C
8 -alkynyl such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl--2-butynyl, 1-methyl-3--butynyl, 2-methyl--3-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,. 5-hexynyl, l-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl--4-pentynyl, 3-methy).-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; unsubstituted or substituted C 3 -C-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; 0050/43960 4 Cl-C 4 -alkoxycarbonyl-C 1
C
4 -alkyl such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propyloxycarbonylmethyl, 1-methylethyloxycarbonylmethyl, butyloxycarbonyirnethyl, 1-methyipropyloxycarbonylmethyl and 1, 1-dixethylethyioxycarbonylmethyl; unsubstituted or substituted C 5
-C
8 -cycloalkeny. such as cyclopent-1-enyl, cyclopant-2-enyl, cyclopent-3-enyl, cyclohex-l-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyciohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cycl,,hex-2-enyl [sic], cyclohex-3-enyl [sic), cyclohept-l-eny. [sic], cyclohept-2-eny. (sic], cyclohept-3-enyl [sic], cyclohept-4-enyl cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl and cyclooct-l-enyl [sic]; unsubstituted or substituted aryl (eg. phenyl, naphthyl, anthryl); unsubstituted or substituted aryl-Cl-C 4 -alkyl (eg. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 4-phenylbutyl); unsubstituted or substituted acyl, eg. Cl-C 4 -alkylcarbonyl such as acetyl, propionyl, butyryl, phenylacetyl and chioroacetyl; unsubstituted or substituted arylcarbonyl such as benzoyl and 2, 4-dichlorobenzoyl; unsubstituted or substituted heteroarylcarbonyl such as 2-pyridylcarbonyl; unsubstituted or substituted aryl-Cl-C 4 -alkenyl (eg.
phenyl-l-ethenyl, 2-pheilyl-l-propenyl, 2, 2-diphenylethenyl, 1-phenyl-l-propen-2-yl and 1-phenylbu-tenyl); unsubstituted or substituted aryloxy-Cl-C 4 -alkyl such as phenoxymethyl, phenoxyethyl and phenoxypropyl; unsubstituted or substituted heteroaryl (eg. 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 1-pyrazo~lyl, 3-pyrazolyl, 4-pyrazolyl, 2-pyrazinyl, 2-pyrimidyl, 4-pyrimidyl, 1-indazolyl, 3-indazolyl, 2-furyl, 3-f uryl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-thiophenyl, 3-thiophenyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 2-is oindolyl, 1-indolyl, 1-indazolyl, 1 ,2-benzothiazol-3-yl, 1, 3-benzothiazol-2-yl, 3-isoxazolyl, 4-isoxazolyl, 0050/43960 3-isothiazolyl, 4-isothiazolyl, 1,2-benzoxazol-3-yl, 1,3-benzoxazol-2-yl, 1,2,4-triazolyl, 1,3, 4-triazolyl, 7-purinyl, 2-quinolyl, 3-guinolyl, 4-quainolyl, 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; unsubstitut d or substituted heteroaryl-Cl-C 4 -alkyl (eg.
2-pyridylmethyl, 3-pyridylmethyl); unsubstituted or substituted heteroaryl-C 2
-C
4 -alkenyl (eg.
2' -furyl-2-ethenyl, 2 '-thienyl-2-ethenyl, 3 '-pyridyl-2-ethenyl); unsubstituted or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1, 3--dioxanyl, 3-tetrahydrothiopyranyl).
In addition to hydrogen, the radicals designated as unsubstituted or substituted contain eg. the following radicals: halogen such as fluorine, chlorine, bromine and iodine; Cl-C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methvlbutyl, 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-dimet 1 -vlbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbu.yl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl and 1-ethyl-2-methylpropyl;
C
1
-C
6 -alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1, 1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 3-methylbutyloxy, 1, 1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1, 1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1, 3-dimethylbutyloxy, 2, 2-dimethylbutyloxy, 2, 3-dimethylbutyloxy, 3, 3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutiloxy, 1,1, 2-trimethylpropyloxy, 1,2,2-tr' Iylpropyloxy, 1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy; 0050/43960 6 2 1
,-C
6 -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butyithio, 1-methylpropyithio, 2-methylpropylthio, 1, 1-dirnethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutyithio, 2, 2-di-methylpropylthio, 1-ethyipropyithia, hexylthio, 1 ,1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1-diin-thylbutylthio, 1, 2-dimethylbutyithia, 1, 3-dimethylbutylthio, iethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethylbutyithia, 1-ethylbutylthio, 2-ethylbutyithio, 2-trimethylpropylthio, 1,2, 2-trimethylpropylthio, 1-ethyl-1--methylpropylthio and 1-ethyl-2-methylpropylthio; Cl-C 4 -haloalkyl, particularly CI-C 2 -haloalkyl such as chioromethyl, dichloromethyl, trichioromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chiorofluorolaethyl, dichlorofluoronethyl, chiorodifluoromethyl, 1-f luoroethyl, 2-f luoroethyl, 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; Cl-C 4 -haloalkoxy, particularly Cl-C 2 -haloalkoxy such as chloromethyloxy, dichloroinethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chiorodifluoromethyloxy, 1-f luoroethyloxy, 2-f luoroethyloxy, 2, 2-difluoroethyloxy, 2,2, 2-tritluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2, 2-difluoroethyloxy, 2, 2-dichloro-2-fluoroethyloxy, 2,2, 2-trichloroethyloxy and pentafluoroethyloxy;
C
2
-C
6 -alkenyloxy such as ethenyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-rethyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-mothyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-xethyl-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-diinethyl-2-propenyloxy, 1-ethyl-l-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy, 0050/43960 7 3-methyl-1-opentenyloxy, 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl--2-pentenyloxy, 3-rnethyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-u..entenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4--pentenyloxy, 1, i-dimethyl-2-butenyloxy, 1, 1-dimethyl-3-butenyloxy; cyano; cyanato, thiocyanato; nitro; amino; hydroxyl; carboxyl; di-Cl-C 6 alkyl amino, particularly di-C, -C 4 -alkyl amino such as N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-di -methylethyl) amino, N,N-dibutylamino, N, N-di C1-methylpropyl) amino, N, N-di (2-methyipropyl )amino, N, N-di 1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N--methyl-N-( 1-methylethyl)amino, N-butyl-N-methyl amino, N-methyl-N- (l-methylpropyl) amino, N-methyl-N-( 2-methylpropyl )aminio, 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, 1-methylpropyl )-N-propylamino, 2-methylpropyl )-N-propylamino, 1, 1-dimethylethyl)-N-propylamino, N-butyl-N-( 1-methylethyl )amino, 1-methylethyl 1-methylpropyl) amino, 1-methylethyl 2-methylpropyl )amino, 1, 1-dimethylethyl 1-methylethyl) amino, N-butyl-N-( l-methylpropyl )amino, N-butyl-N-( 2-methylpropyl )-amino, N-butyl-N-( 1, 1-dimethylethyl)amino, Nl-( 1-methylpropyl)-N-( 2-methylpropyl )amino, 1, 1-dimethylethyl)-N-( 1-methylpropyl)amino and 1, 1-dimethylethyl 2-methyipropyl )amino; phenyl, phenoxy, phenylthio and phenylamino which, for their part, can carry one to five halogen atoms as mentioned above; and/or one to five C 1 -CG-alkoxy groups as mentioned above; and/or one to five Cl-C 6 -alkylthio groups as mentioned above; and/or one to five Cl-C 4 -haloalkyl groups as mentioned above; 0050/43960 8 and/or one to four C 1
-C
6 -alkoxyiminomethyl groups such as methoxyiminomethyl, ethoxyiminomethyl, n-propoxyiminomethyl, n-butoxyiminomethyl, n-pentoxyiminomethyl, n-hexoxyiminomethyl, allyloxyiminomethyl, benzyloxyiminomethyl, iso-propoxyiminomethyl, iso-butoxyiminomethyl and tert-butoxyiminomethyl, and/or one to four C 1
-C
6 -alkoxyiminoethyl groups such as methoxyiminoethyl, ethoxyimino-1-ethyl, n-propoxyimino-1-ethyl, n-butoxyimino- 1-ethyl, n-pentoxyimino-l-ethyl, n-hexoxyimino-l-ethyl, allyloxyimino-1-ethyl, benzyloxyimino-1-ethyl; and/or phenyl, phenoxy and benzyloxy; and/or a C 1
-C
4 -alkyliminomethyl group such as methyliminomethyl and ethyliminomethyl; and/or one to four C 3
-C
6 -cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The novel compounds of the general formula I can be obtained during preparation as E/Z isomer mixtures on account of the C=C or C=N double bonds. These can be separated into the individual components in a customary manner by crystallization or chromatography.
Both the individual isomeric compounds and their mixtures are comprised by the invention and can be used as fungicides.
Particularly preferred compounds of the formula I are those in which
Y
is oxygen or the group N-R 6
Z
1 and Z 2 are independently of one another hydrogen, methyl, methoxy, chlorine, bromine or trifluoromethyl,
R
I
is hydrogen, methyl or trifluoromethyl, R2 is hydrogen, or unsubstitued or substituted alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, heteroarylalkyl, aryloxyalkyl or heteroaryloxyalkyl and 0050/43960 9
R
3
R
4
R
5 and R 6 are hydrogen, methyl or ethyl.
Additionally, compounds of the formula I are preferred in which Y is oxygen,
Z
1 and Z 2 are hydrogen,
R
3 and R 4 are methyl,
R
5 is hydrogen and in which
R
1 is hydrogen or methyl and
R
1 [sic] is hydrogen, alkyl, allyl, propargyl, arylalkyl, heteroarylalkyl, aryloxyalkyl or heteroaryloxyalkyl.
In addition, compounds I are preferred in which R 1 is hydrogen and
R
2 is (3-trifluoromethyl)benzyl.
Compounds I are additionally preferred in which R 1 is methyl and
R
2 is (3-trifluoromethyl)benzyl.
The compounds of the general formula I as claimed in claim 1 are prepared, for example, as described in scheme 1 (Z 1 and Z 2 denote hydrogen).
Scheme 1 0 0 0
(II)
R
7 =Alkyl preferably CH 3 C
H
2
NR
4
'CM
R
2
Y-N
HNR
4
R
5 (111) w
IR
2 y-NH 2 (if approp. x FIX) (VIII) R 5
H)
R
1 RN 0 04N'R N- 0 R 3 (VI) (VII)
(IV)
.0050/43960 11 The compounds of the general formula I can be prepared, for example, from the esters of the general formula II (preparation disclosed in EP 499 823) by reacting II with ammonia or amines
(III).
Compounds of the general formula I in which R5is H can be prepared by reacting a carbonyl compound of the general formula IV (preparation see EP 393 428, R 1 H and EP 499 823, R 1 other than H) with a monoalkylamine V to give a cyclic hemiaminal VI, which is in equilibrium with its aldehyde or keto form VII and reacts as the carbonyl compound VII with a hydroxylamine or hyrrazine derivative VIII cr one of its acid addition salts, the substances of the general formula I (where R 4 alkyl and R 5 H) being formed.
The intermediates of the formula VI or VII can also be prepared from the compound X (Scheme (which is accessible in a known manner from phenylglyoxylate estzrs by reaction with alkoxyamine hydrochloride and monoalkylamine), by doubly metallating X (to give XI), for which purpose metal 2lkyls such as butyllithium (J.
Org. Chem. 29 (1964), 853) or metal amides such as eg. magnesium diisopropylamide (EP 418 013) are suitable, and reacting XI with a carboxylic acid derivative XII, eg. a carboxylic acid chloride, anhydride or ester, or converting XI with an aldehyde XIII into the carbinol XIV, which is then oxidized to the carbonyl compound VII (or its cyclic form VI) in a manner known per se.
A, LI ,00so/43960 Scheme 2 0 O
(IX)
1) H 2
NOR
3 x HX 2) H 2
NR
4 0 1'0W N R4,N.H (x 2 R-M (M Li) or M(NR2)2 (M Mg) 0
R
1 -CX (XII) x--
R-
M
(XI)
RCH
(XIII)
(VII)
HO
(XIV)
(VI)
Hydroxylamine derivatives of the gene: al formula VIII (Y 0) are either known or can be prepared according to known methods in a similar manner to Houben-Weyl X/1, pp. 1192 and 1183.
Hydrazine derivatives of the general formula VIII (Y NR 6 are either known or can be prepared, also according to known methods, in a similar manner to Houben-Weyl X/2, pp. 271, 280 and 740.
Amines (III and phenylglyoxylate esters carboxylic acid derivatives (XII) and aldehydes (XIII) are generally known.
The following procedures and examples will illustrate the preparation of the novel active compounds and intermediates.
,0050/43960 13 Example 1 a) Preparation of l-hydroxy-2-methyl-4-methoxyimino-1,2,3,4-tetrahydroisoquinolin-3-one (Compound of the formula VI in Scheme 1; RI=H, R 3
=R
4
=CH
3 11.0 g (50 mmol) of the aldehyde of the formula IV [(RI=H,
R
3 =R7=CH 3 preparation see EP 393 428)] are dissolved in 200 ml of THF and stirred at 25'C for 30 min with 10 ml of a 40% strength aqueous methylamine solution (112 mmol). The resulting compound VI partially precipitates; the precipitate is filtered off with suction, washed with ether and dried. Further product is obtained by concentrating the mother liquor, triturating the residue with diisopropyl ether and filtering off with suction. Colorless crystals, m.p. 116 168°C, yield 9.0 g (82% of theory).
1 H-NMR (CDC1 3 ,D scale): 2.2 2.5 (br, OH), 3.26 3H, NCB 3 4.06 3H, OCH 3 4.06 3H, OCH 5.71 1H, CH-OH); 7.2 3H) and 8.41 (dd, 1H; aromatic protons) 13C-NMR (CDC13,D scale): 33.0 NCH 3 64.0 OCH 3 82.6 (d, HC-OH; 125.0 127.6/128,7/130.2/130.6 (4d, tertiary aromatic 135.6 C-CHOH); 141.6 161.4 C=0) IR (KBr,v in cm- 1 3295, 1648, 1576, 1021, 765.
b) Preparation of 2-(0-3-bromobenzyloximinoethyl)-a-methoxyimino-N-methylphenylacetamide (Compound No. 58 in Table 1) 1.7 g (7.7 mmol) of hemiaminal of the formula VI as prepared above according to a) are refluxed for 1 h with 2.3 g (7.7 mmol) of 3-bromobenzyloxyamine hydrochloride of the formula VIII
(R
2 -y=3-BrC 6
H
4
CH
2 in 150 ml of THF. After cooling, the reaction mixture is washed twice with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residual oil is chromatographed on silica gel using cyclohexane/ethyl acetate 90:10 to 70:30 and the oily product is crystallized by triturating with diisopropyl ether. Almost colorless crystals, m.p.
103 105'C, yield 1.1 g (38% of theory).
1H-NMR (CDC13, D scale): 2.88 3H, NCH 3 3.90 3H, OCH3); 5.10 2H, OCH2); 6.73 (br 2, 1H, NH); 7.1 7.8 8H, aromatic protons); 7.94 1H, CH=N-O).
.0050/43960 14 Example 2 Preparation of -3-methylbenzyloximinomethyl)-a-methoxyimino- N-methylphenylacetamide (Compound No. 36 in Table 1) 13.6 g (40 mmol) of methyl 2-(O-3-methylbenzyloximinomethyl)c-methoxyiminophenylacetate (preparation see EP 499 823) are dissolved in 100 ml of tetrahydrofuran, 12 ml of 40% strength aqueous methylamine solution 150 mmol of CH 3
NH
2 are added and the mixture is stirred at 40°C for 7 h.
It is allowed to cool to 25°C, diethyl ether is added, the phases are separated, and the organic phase is washed with water, dried over sodium sulfate and concentrated in vacuo.
Yellowish oil, yield 13.0 g 96% of theory.
IR (film, v in cm- 1 1669, 1527, 1411, 1035, 980, 785, 756.
The Tables below give examples of active compounds which can be prepared in the manner described: ,0050/43960 Table 1
*CH
3 CH3 -N .H Compd.
R
2 No.
1 H physical data NMR (ppm)) 2 3 4 5 6 0113
CH
3
CH
2
CH
3
CH
2
CH
2
C
2
=CH-CH
2
CH
2 =C(Cl)-C!H2 M.p. 98C NMR 2.94 (d,3H), 3.97 4.68 (s,21i), 5.43 (d,2H), 6.8 7.2-8.0 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27
CH
3 -CH=CH-CH H 3
CH
2 =C (CH 3
)-CH
2
HC=C-CH
2
CH
3
-O-CH
2 -C11 2
C
2
H
5 -O-C11 2
-CH
2 Cl-CH 2
-CH
2 CClo-C 3
H
5
-CH
2 C11 3 -CH=CH-C H
CH
2
=CH-CH
2 -C11 2
CH
3
-C=-CCH:!
CH
3
CH
2
C-=C-CH
2
CH
3 -(CH2) 3
CH
3
-(CH
2 4
(CH
3 3
C
Cyclo-CGH1, 2-CH 3 -Cy-Clo-C 6
H
1 0
C
6
H
5
-CH
2 2-F-C 6
H
4
-CH
2 3-F-C 6
H
4 -C1 2 4-F-C 6
H
4 -CT 2 2-Cl-C 6
H
4
-CH
2 M.p. 940C M.p. 116-119 0
C
,0050/43960 28 3-Cl-C 6
H
4
-CH
2 29 4-Cl-C 6
H
4
-CEI
2 2, 3-C1 2
-C
6
H
3
-CH
2 31 2, 4-C 2
-C
6
H
3
-CH
2 32 3 ,5-Cl 2
-C
6
H
3
-CH
2 33 2, 6-C1 2
-C
6
H
3
-CH
2 34 3, 4-Cl 2
-C
6
H
3
-CH
2 2-CH 3
-CSH
4
-CH
2 36 3-CH 3
-C
6
H
4
-CH
2 37 4-CH 3
-C
6
H
4
-CH
2 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 2, 3- (CH 3 2
-C
6
H
3
-CH
2 2, 4-(CH 3 2
-C
6
H
3
-CH
2 2, 5-(C1 3 2
-C
6 H3-CH 2 3 4- (CE 3 2
-C
6
H
3
-CH
2 3, 5- (CE 3 2
-C
6
H
3
-CH
2 4 ,5-(CE 3 2
C
6
H
3
-CH
2 2, 3, 4-(CH 3 3
-C
6 2
-CH
2 2, 4,5- (C1 3 3
-C
2
-CH
2 2 4, 6- CH 3 3
-C
6
H
2
-CH
2 2, 3, 6- (CH 3 3
-C
6
HI
2 -CHi 2 2-Cr 3
-C
6
H
4
-CH
2 3-CF 3
-CGH
4
-CH
2 4 -CF 3
-C
6
H
4 -1:H 2 2-CH 3 -3-CF 3
-C
6
H
3 -C1 2 2-CH 3 -4-CF 3
-C
6
H
3
-CH
2 2-CF 3 -3-C 3
-C
6
H
3
-CH
3 2-CF 3 -4-CH 3
-C
6
H
3
-CH
2 2-CF 3 -5-C 3
-C
6
H
3
-CH
2 2-CH 3 -5-CF 3
-C
6
H
3
-CH
2 2-Br-C 6
H
4
-CH
2 3-Br-C 6
H
4
-CH
2 4-Br-C 6
H
4
-CH
2 2- isopropyl -C 6
H
4
-CH
2 3- isopropyl.) -C 6
H
4
-CH
2 4- (isopropyl -C 6
H
4
-CH
2 2- isopropyl..) -3-C1-C 6
H
3
-CH
2 2- isopropyl -4-Cl-C 6
H
3
-CH
2 2- (isopropyl )-5-Cl-C 6
H
3
-CH
2 2-CH 3 isopropyl -C 6
H
3
-CH
2 2-CH 3 (iSOPropyl )-C 6
H
3
-CH
2 IR: 1667, 1527, 1028, 978, 787, 700 M.p. 142 0
C
M.p. 92 0
C
NMR: 2.9 3.93 5.1 (s,2H), 6.8 (s,2H) and 7.2-8.0 (xn,3H) IR: 1667, 1526, 1036, 980, 747 IR: 1669, 1527, 1411, 1035, 980, 785, 756 1661, 1522, 1492, 1087, 1035 M.p. 166 168 0
C
M.p. 103 1050'C 0050/43960 72 73 74 76 77 78 79 81 82 83 17 2-CH 3 iSopropyl) -C 6
H
3
-CH
2 2-t-C 4 H g-C 6
H
4
-CH
2 3-t-C 4 H9-C 6
H
4
-CH
2 4-t-C 4 H9-C 6
H
4
-CH
2 2-CH 3 -3-t-C 4 Hq-C 6
H
3
-CH
2 2-CH 3 -4-t-C 4 Hq-C 6
H
3
-CH
2 2-CH 3 -5-t- 4
H-C
6
H
3
-CH
2 3-CH 3 -4-t-C 4 Hq-C 6
H
3
-CH
2 3 -CH 3 5-t-C 4
H
9
-C
6
H
3
-CH
2 2-Cl-3-t-C 4
H
9
-C
6
H
3
-CH
2 2-Cl-4-t-C 1 Hq-CfH 3
-CH
2 2-C1-5-t-C 4
H-C
6
H
3
-CH
2 3-cl- 4-t-C 4 Hq-CH 3
-H
2 3-Cl-5-t-C 4
H-C
6
H
3
-CH
2 2-OCH 3
-C
6
H
4
-CH
2 3-OCH 3
-C
6
H
4
-CH
2 1NMR: 1.91 (s,911), 2.9 3.90 (s,3H), 5.15 6.7 (s,1H) and 7.18-8.0 (in, 9) NMR: 2.8 3.80 3.9 (s,3H), 5.75 6.7 6.8-8.0 (m,9H) 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 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-CH 3
-C
6
H
3
-CH
2 3-CH 3 -5-OCH- 3
-C
6
H
3
-CH
2 2-Cl-3-OCH -CH 3
-CH
2 2-Cl-4-OCH-,-C 6
H
3
-CH
2 2-Cl-5-OCH- -C 6
H
3
-CH
2 2-OCH 3 -3-CJ.-C 6
H
3
-CH
2 2-OCHi 3 4-C1 -C 6
H
3
-C-H
2 2-0CH 3 -5-C2-C 6
H
3
-CH
2 2-CH 3 cyclohexyl.) -C 6
H
3
-CH
2 2-CH 3
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 2-CH 3 (iethoxyiminoinethyl) -C 6
H
3
-CH
2 2-Methoxyirninomethyl-C 6
H
4 -CH4 3-Methoxyininomethyl-C 6
H
4 -CH4 2-C11 3 (inethoxyiminomethyl -C 6
H
3
CH
2 2-PhenyJ.-C 6
H
4
-CH
2 3-Phenyl-C 6 i 4
-CH
2 4-Phenyl-C 6
H
4 -CH2 2-Phenoxy-C 6
H
4
-CH
2 -0050/43960 108 109 110 ill 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 3-Ph enoxy-C 6
H
4 -CH2 4-Phenoxy-C 6
H
4
-CH
2 2-BenZY10XY-C 6
H
4
-CH
2 3 -Benzyloxy-C 6
H
4
-CH
2 4-BenzyloXY-C 6
H
4
-CH
2 1-Naphthyl-CH 2 2-NaphthYl-CH 2 9-Anthryl-CH 2 2-CH 3 -3-Cr 5
O-C
6
H
3
-CH
2 2-CH 3 -4-C 6
H
5 0-C 6
H
3
-CH
2 2-CH 3 -5-C 6
H
5 0-C 6
H
3
-CH
2 3 -CH 3 4 -C 6 HS -C 6
H
3
-CH
2 4-CH 3 -5-C 6
H
5 0-C 6
H
3
-CH
2 2-C1-3-C 6
H
5 0-C 6
H
3
-CH
2 2-Cl-4-C6 5
O-C
6
H
3
-CH
2 2-C1-5-C 6
H
5 0-C 6
H
3
-CH
2 3-C1-4-C 6
H
5 0-C 6
H
3
-CH
2 3-Cl -5 -C 6
H
5 0OC 6 H8 3
-CH
2 2-CH 3 -4-C0 2
CH
3 -C6H 3
-CH
2 2-CH 3 -4-CO 2
CH
3
-C
6
H
3
-CH
2
C
6 H5-CH(CH 3 2-F-C 6
H
4 -CH CH 3 2-F-C 6
H
4 -CH (CH 3 4-F-C 6
H
4 -CH (CH3) 2-C1-C 6 fl 4 -CH (CH 3 3-C1-C 6
H
4 -CH (CH 3 4-Cl-C 6
H
4 -CH CH 3 2, 3-Cl 2
-C
6
H
3 -CH (CE 3 2, 4-Cl 2 -C6H 3 -C CH 3 2, 5-Cl 2
-C
6
H
3 -CH (CE 3 2, 6-C1 2
-C
6
H
3 -CH CE 3 3, 4-Cl 2
-C
6
H
3 -CH CE 3 2-CH 3
-C
6
H
4 -C CE 3 3-CH 3 -C6H 4 -CH (CH3) 4-CHy--C 6
H
4 -C CE 3 2, 3- (CH 3 2 -Cr 6
H
3 -CH (CH 3 2, 4- (CH 3 2
-C
6
H
3 -CH (CH 3 2, 5- (CH 3 2
-C
6
H
3 -CH (CH 3 3, 4- (CE 3 2
-C
6
H
3 -CH CE 3 3, 5- (CH 3 2
-C
6
H
3 -CH (CH 3 4, 5- (CE 3 2
-C
6
E
3 -CH CH 3 2, 3, 4- (CH 3 3
-C
6
H
2 -CE (CH 3 IR: 1669, 1526, 1035, 979, 819, 754 M.p. NMR: 1.58 2.9 3.8 (s,3H), 5.22 1H), 6.69 (s,1H) and 7.18-8.0 (in, 9) M.p. 1140C 135 136 137 138 139 140 141 142 143 144 145 146 147 148 150 ,0050/43960 19 151 2,4- (CH 3 3 -C41 2 -CH (CH 3 152 2g, -(CH 3 3
-C
6 1 2 CH (CH3) 153 2, 2, L-(CH 3 3
-C
6
H
2
-CH(CH
3 154 2-CF 3
-C
6 Ei 4
-CH(CH
3 155 3---CH-H(H NMR: 1.6 2.9 3.85 (s,3H), 5.3 1H), 6.8 (s,1H) and 7.1-8.0 (m,9H) 156 4-CF 3
-C
6
H
4
-CH(CH
3 157 2-CH 3 -3-CF-C 6
H
3 -CH CH 3 158 2-CH 3 -4-CF3-C 6
H
3 -CH CH 3 159 2-CH 3 -3-CH 2
C
6
H
3 -CH CH 3 160 2-CH 3 -4-CH-.-C 6
H
3 -CH CH 3 161 2-Cl1 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 1 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 isopropyl)-C 6
H
4
-CH(CH
3 169 2- isopropyl) -3-Cl-C 6 1 3 -CH CH 3 170 2- isopropyl -4-C.-C 6
H
3 '-CH CH 3 171 2-(isopropyl)-5-C-CH 3
-CH(CH
3 172 2-CH 3 isopropyl) -C 6
H
3 -CH CH 3 173 2-C11 3 isopropyl -C 6
H
3 -CH CH 3 174 2-CH 3 isopropyl 6
H
3 -CH CH 3 175 2-t-C 4
H
9
-C
6
H
4 -CH- CH 3 176 3-t-C 4
H
9
C
6
H
4 -CH- (CH 3 177 4-t-C 4
H-C
6 -1 4 -CH- C CH 3 178 2-CH 3 -3-t-C 4
H
9
-C
6
H
3 -CH (CH 3 179 2-CH 3 -4-t-C 4
H
9
-C
6
H
3 -CH (CH 3 180 2-CH 3 -5-t-C.
4
H
9
-C
6
H
3 -CH CH 3 181 3-CH 3 -4-t-C 4 H9-C 6
H
3 -CH (CH 3 182 3-CH 3 -5-t-C 4
H
9
-C
6
H
3 -CH (CH 3 183 2-Cl-3-t-C 4
H
9
-C
6
H
3 -CH (CH 3 184 2-C1-4-t-C 4 8 9
-C
6
H
3 -CH CH 3 185 3-C1-4-t-C 4
H-C
6
H
3 -CH CH 3 187 3-C1-5-t-C 4
H-C
6
H
3 -CH (CH 3 188 2-OCH 3
-C
6
H
4
-CH
2 -CH CH 3 189 3-OCH 3
-C
6
H
4
-CH
2 -CH CH 3 190 4-OCH 3
-C
6
H
4 -C11 2 -CH (CH 3 191 2-CH 3 -3-OCH 3
-C
6
H
3 -CH (CH 3 192 2-CH 3 -4-OCH 3
-C
6
H
3 -CH(CH3) 193 2-CH 3 -5-OCH 3
-C
6
H
3 -CH (CH 3 194 3-CH 3 -5-OCH 3
-C
6 H3-CH (CH3) -0050/43960 195 3-CH 3 -5-OCH 3
-C
6
H
3 -CH (CU 3 196 2-Cl-3-OCU 3
-C
6
H
3 -CH (CU 3 197 2-Cl-4-OCH 3
-CGH
3 -CH (CU 3 198 2-C1-5-OCH 3
-C
6
H
3 -CH CH 3 199 2-OCH 3 -3-Cl-C 6 ri 3 -CH (CH 3 200 2-OCH 3 -4-Cl-C 6
H
3 -CH (CU 3 201 2-OCH 3 -5-C-C 6
H
3 -CH (CU 3 202 2-CH 3 cyclohexyl -C 6
H
3 -CH (CH 3 203 2-CH 3 -4-C 6
H
5
-C
6
H
3 -CH (CH3) 204 2-CH 3 -3-Br-C 6
H
3 -CH (CH 3 205 2-CH 3 -4-Br-C 6
H
3 -CU (CH 3 206 3-CH 3 -5-Br-C 6
H
3 -CH( CU 3 207 2-CH 3 (methoxyizninomethyl) -CGH 3 -CH (CU 3 208 2-Methoxyiminomethyl-C 6
H
4 -,CH CH 3 209 3-Methoxyiminomethyl-C 6
H
4 -CH (CU 3 210 2-CH 3 (methoxyiminomethyl -C 6
H
3 -CH CU 3 211 2-Phenyl-C 6
H
4 -CH CH 3 212 3-Phenyl-C;H 4 -CH (CU 3 213 4-Phenyl-C 6
H
4 -CH CfH 3 214 2-Phenoxy-C 6
H
4
-CH(CH
3 215 3-Phenoxy-C 6
F
4 -CH( CH 3 216 4-PhenCXY-C 6
H
4 -CH( CH 3 217 2-BenzyloXY-C 6
H
4 -CU (CU 3 218 3-BenzyloXY-C 6
H
4 -CH CU 3 219 4-Benzyloxy-C 6 4
-CH(CH
3 220 1-Naphthyl-CH( CU 3 221 2-Naphthyl-CH(CH3) 222 9-Anthryl-CH (CH 3 223 2-CH 3 -3--C 6
H
5 0-C 6
H
3 -CH (CU 3 224 2-CH 3 -4-C 6
H.
5
O-C
6
H
3 -CH (CH 3 225 2-CH 3 -5-C 6
H!,O-CEU
3 -CH CH 3 226 3-CH 3 -4-C 6
H
5 0-C 6
H
3 -CH( CU 3 227 4-CH 3 -5-C 6
H
5 0-C 6
H
3 -CH (CU 3 228 2-Cl-3-C 6
H
5 0--C 6
H
3 -CU (CH 3 229 2-Cl-4-C 6
U
5 0-C 6
U
3 -CH (CH 3 230 2-Cl-5-C 6
U
5 0-C 6
U
3 -CU CH 3 231 3-Cl-4-C 6
H
5 O-C6H 3 -CU (CH 3 232 3-Cl-5 -C 6
H
5 0-C 6
H
3 CH (CU 3 233 2-CH 3 -4-CO 2
CH
3
-C
6
H
3 -CU (CH 3 234 2-CH 3 -5-CO 2
CH
3
-CSH
3 -CU (CH 3 235 C 6
H
5
-(CH
2 2 236 2-F-C 6
H
4
-(CU
2 2 237 3-F-C 6
U
4
-(CU
2 2 238 4-F-C 6
H
4
-(CU
2 2 239 2-Cl-C 6
U
4 -(C1 2 2 240 3-Cl-C 6
H
4
-(CH
2 2 241 4-Cl-C 6
H
4
-(CU
2 2 0050/43960 21 242 2,3-C1 2
-C
6
H
3
-(CH
2 2 243 2,4-C1 2 -CsH 3
-(CH
2 2 244 2, 5-Cl 2
-C
6
H
3 (C1 2 2 245 2, 6-C1 2
-C
6
H
3
(CE
2 2 246 3,4-Cl 2
-C
6
H
3
-(CH
2 2 247 2-CH 3
-C
6
H
4
(CH
2 248 3-CH 3
-C
6
H
4 -(Cli 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 2,3-(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 -C6H 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 3
(CH
2 2 256 2, 3,4- (CH 3 3
-C
6
H
2
(CH
2 2 257 2,4,5-(C 3 3
-C
6
H
2
-(CH
2 2 258 2,4,6-(CH 3 3 -C6H 2
-(CH
2 2 259 2,2,6-(CH3) 3
-C
6
H
2
-(CH
2 2 260 2-CF 3
-C
6
H
4
-(CH
2 2 261 2-CF 3
-C
6
H
4
-(CH
2 2 ze6 2 4-CF 3 -C6H 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
(CE
2 2 265 2-CF 3 -3-CH 3
-C
6
H
3
(CE
2 2 269, 2-CF 3 -4-CH 3
-C
6
H
3
-(CH
2 2 267 2-CF 3 -5-CH 3
-C
6
H
3
(CE
2 2 268 2-CH 3 3-CE 3
-C
6
H
3
CH
2 2 269 2-Br-C 6
H
4
CH
2 2 270 3-Br-C 6 11 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-(isopropyl)-C 6
H
4
-(CH
2 2 274 4-(isopropyl)-C 6
H
4
-(CH
2 2 275 2- (isopropyl) -3-C1-C 6
H
3
(CH
2 2 276 2-(isopropyl)-4-Cl-CGH 3
-(CH
2 2 277 2-(isopropyl)-5-C1-C 6
H
3
-(CH
2 2 278 2-CH 3 -3-(isopropyl)-C 6
H
3
-(CH
2 2 279 2-CH 3 (isopropyl) -C 6
H
3
(CH
2 2 280 2-CH 3 (i sopropyl)-C 6 3
(CH
2 2 281 2-t-C 4 H9-C 6
EH
4
-(CH
2 2 282 3-t-C 4 H9-CE1 4
(CH
2 2 283 4-t-C 4 H9-C6H4-(CH 2 2 284 2-CH 3 -3-t-C 4
H
9
-C
6
H
3
-(CH
2 2 285 2-CH 3 -4-t-C 4 H9-CGH 3
(CE
2 2 286 2-CH 3 -5-t-C 4 H9-C 6
H
3
(CH
2 2 287 3-CH 3 4-t-C 4 H9-C 6
H
3
(CE
2 2 288 3-CH 3 -5-t-C 4
E,
9
-C
6
H
3
(CE
2 2 0050/43960 22 289 2-Cl-3-t-C 4 9
-C
6
H
3
-(CH
2 2 290 2-Cl-4-t-C 4
U
9
-C
6
H
3 (C:1 2 2 291 2-C1-5-t-C 4
H
9
-C
6
H
3 CH2 292 3-Cl-4-t-C 4 H9-C 6
H
3
(CU
2 2 293 3-C1-5-t-C 4 Hq-C 6
H
3
(CH
2 2 294 2-OCH 3
-C
6
H
4
-(CH
2 )2 295 3-OCH 3
-C
6
H
4
(CU
2 2 296 4-OCH 3
-C
6
H
4
-(CH
2 2 297 2-CH 3 -3-OCH 3
-CG
6 r' 3
(CH
2 2 298 2-CH 3 -4-OCH 3
-C
6
H
3
-(CH
2 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
(CU
2
Z
301 3-CH 3 -5-OCH 3
-C
6
H
3
-(CH
2 2 302 2-C1-3-OCH 3
-C
6
H
3
(CH
3 2 303 2-Ci-4-OCH 3
-C
6
H
3
-(CH
3 2 304 2-Cl-5-OCH 3
-C
6 7i 3
CR
3 2 305 2-OCH 3 -3-Cl-C 6
H
3
(CU
3 2 30C6 2-OCH 3 -4-C1-C 6
H
3
(CR
3 2 307 2-OCH 3 -5-Cl-C 6
H
3
CH
3 2 308 2-CH 3 (cyclohexyl) -C 6 3
(CH
2 2 309 2-CH 3 -4-C 6
H
5
-C
6
H
3
(CU
2 2 310 2-CH 3 I-Br-C 6
U
3
(CR
2 2 311 2-CU 3 -4-Br-C 6
U
3
(CR
2 2 312 2-CH 3 -5-Br-C 6
U
3
(CH
2 2 313 2-CH 3 (methoxyiminomethyl) -C 6
U
3
(CU
2 2 314 2-Methoxyiminomethyl-C 6
H
4
(CU
2 2 315 3-Methoxyiminomethyl-C 6
U
4
(CR
2 2 31GC 2-CH 3 (miethoxyiminomethy..) -C 6
H
3
(CR
2 2 317 2-Phenyl-C 6
U
4 C2 318 3-Phenyl-C 6
R
4
-(CR
2 2 319 4-Phenyl-C 6
H
4
(CH
2 2 320 2-Phenoxy-C 6
U
4
-(CR
2 )2 321 3-Phenoxy-C 6
U
4
(CU
2 2 322 4-Phenoxy-C 6
R
4
(CR
2 2 323 2-BenZYloXY-C 6
H
4
-(CH
2 2 324 2-Benzyloxy-CsR 4
(CR
2 2 325 4-Benzy1oXY-C 6
R
4
CR
2 2 326 1-Naphthyl-(CH 2
)Z
327 2-Naphthyl-(CH 2 2 328 9-Anthryl-(CH 2 2 329 2-CH 3 -3-C6HSO-C 6
H
3
(CU
2 2 330 2-CH 3 -4-C 6
H
5
O-C
6 3
(CH
2 2 331 2-CU 3 -5-C 6
H
5 0-C 6
R
3 C2 332 3-CH 3 -4-C 6
H
5 0-C 6
R
3
(CU
2 2 333 4-CH 3 -5-C 6
H
5 0-C 6 3
-(CU
2 2 334 2-Cl-3-CGR 5 0-C 6
H
3
(CR
2 2 335 2-C1--4-C 6
H
5 0-C 6
H
3
(CR
2 )2 -0050 /43960 336 2-Cl-5-C 6 H~iO-C 6
IH
3 337 3-Cl-4-C 6
H!;O-C
6
H
3
(CH
2 1 2 338 3-Cl-5-C 6 r5O-C 6
H
3
CH
2 2 339 2-CHa4CO 2
CH
3
-C
6
H
3
(CH
2 2 340 2-CH 3 -5-CO 2 C2H 3
-C
6
H
3
-(CH
2 2 341 C 6
H
5
-CH=CH-CH
2 342 2-F-C 6
H
4
-CH=CH-CH
2 343 2-F-C 6
H
4 -CfH=CH-CH 2 344 4-F-C 6
H
4 -Cf=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
2 348 2, 3-Cl 2
-C
6 11 3 -CH=CH-CHi 2 349 2, 4-C1 2
-C
6 fE 3
-CH=CH-CH
2 350 2, 5-Cl 2
-C
6 1 3
-CH=CH-CH
2 351 2, 6-Cl 2
-C
6 11 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 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-CI
2 361 4, 5- CH 3 2
-C
6
H
3
-CHCH-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
6
H
2
-CH=CH-CH
2 364 2, 4, 6- (CH 3 3
-C
6
H
2
-CH=CHI-CH
2 365 2, 3, 6- (CH 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
2 368 4-CF 3
-C
6
H
4 -Cli=CH-CH 2 369 2-CH 3 -3 -CF 3 -C6 3
-CH=CH-CH
2 370 2-CH 3 -4 -CF 3
-C
6 Ii 3
-CH=CH-CH
2 371 2-CF 3 -3-CF 3
-C
6
H
3
-CH=CH-CF.
2 372 2-CF 3 -4-F 3
-C
6
H
3
-CH=CH-CI
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 .r-i 2 )3 376 C 6
H
5 2) 4 377 C 6
H
5 -Cfl 2
CH=^CR-CH
2 378 4-F-C 6
H
4 -CH=CH- (C2 379 CH 3
O-CO-CH
2 380 CH3CH 2 0-CO-CO 2 381 CH 3
-CO-CH
2
-CH
2 382 t-C 4 Hq0-CO-CH 2 0050/43960 383 t-C 4 H9O-CO-- (CH 2 2 384 t-C 4 HqO-CO--CH(C1 3 385 386 387 388 389 390 391 392 393 394 395 396 n-C 4
H
9 0-CO--CH 2 iSO-C 4 H0--CO-CH 2 n-C 3
H
7 0-CO--CH 2 s eC-C 4
H
9 0-COCH 2
C
6
;H
5 -CO-C1 2 2-CH 3 -C 6
H
4
C-CO-CR
2 3-CH 3 -C 6
H
4
C--CO-CH
2 4-CH 3 -C 6
H
4
C-CO-CR
2 2-Cl-C 6
H
4 0-CO-CH 2 3-Cl-C 6
H
4 0-CO-CH 2 4-Cl-C 6
H
4 -CO -CR 2
C
6
H
5
-C(CE
3
)=CH-CH
2 NMR: 1.42 2.96 (d,3H), 3.97 4.62 6.87 (s,1H), 7.18-8.0 (in,9H) IR: 1662, 1527, 1445, 1035, 987, 757 397 398 399 N CH 2 NCH2 Cl N CH 2 NCH2
CF
3 NGCTz 400 401 402 0050/43960 Br 403 N CRI Br 404
I
F
N CR 2 i540
CH
2 24076R N C 20409 N C (N CR 2 CH2 409 CR 412
H
1 -0050/43960 26
CH
3 413 Br CN CHi t
C'
414 Gil 3 N CH2 Br 415 Gi 3 N CH 2
~CH
3 416
CH
3 N CH 2 C 1 3 417 Gil 3 N CH 2
CF
3 cl 418 N Cl-I 2
CI
419 i i Cl N CH 2 Cl ~QCl 420Gi C-N CH) 421 Gil 3 N C 2 .0050/43960 27
OCH
3 422 423 Cl Nl CR 2 Br 424 0 2 N N C-Hz 426I I 0 Cl 427 1Cl- 2 2428 [7~jI.Cl-h
CH
2 429 I7J 430 N J 1 cH 3
CH.-
431J 431 N
&H
3 432 'N
CH
2 0 ,0050/43960 28 433 C: 2 CH 2 434 N 'N H 435 N 7 1l- CH 2 100 436 ~IC is ci 437 201 2438 NI
CH
N CH N CH 2
CH
3 C1 440 N CH 2 41 Cl "r CH3 N% CH.
02 442CH UCH2 443 443
C-
.0050/43960 29
CI
4447 1 1 2
CI
445
CH
2
CH
2 447 N C1 Cl 2448 177 CH EI7~l CH 2 449
,CH
3
OH
450 LjN
CH
2 CHl 3 0~C 0 453
NCH
2 N
CH
3 .0050/43960 456 FO0 r NcH 2
CH
3 O0 N NCH 2
CH
3 O0 Cjj71 457 458 459 460 0-7
CH
3
RCH
NH
3 CH 2 CH 3 Ni
CH
3
CH
3
O
CH 3
H
461 35462 463 464 465 466 467 t-BuO-CH 2
-CH=CH-CH
2
(CH
3 2
-C=CH-CH
2
-CH
2 -C (CH 3
=CH-CH
2
(CH
3 2
CHCCH-CH
2
-CH
2 -C CH 3
=CH-CH
2
C
6
H
5 -0-CH CH 3
-CH
2 4-Cl-C 6 11 4 -O-CH CU 3
-CH
2 NMR: 1.3 2.9 3.9 (s,3H), 4.1-4.35 4.65 6.8-7.9 (in, lU) 0050/43960 Table 2
CH
3 N -H Compd. No.
1 2 3 4 6 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34
R
2
H
CH
3
CH
3 CEi 2
CH
3
CH
2
CH
2
CH
2
=CH-CH
2
CH
2 =C (Cl) -CE 2
CH
3 5-CH=CH-CH (CH 3
CH
2 =C (CE 3 -C2 HC=C-CE1 2
CH
3 -0-CH 2
-CH
2
C
2
H
5
-O-CH
2
-CH
2 Cl-CH 2
-CH
2 CClo-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
CCclO-C 6
H
1 1 2-CH 3 -CYClo-C 6
H
1 0
C
6
H
5
-CEI
2 2-F-C 6
H
4
-CH
2 3-F-C 6
H
4
-CH
2 4-F-C 6
H
4
-CH
2 2-Cl-C 6
H
4
-CH
2 3-Cl-C 6
H
4
-CH
2 4-C1-C6H 4
-CH
2 2, 3-Cl 2
-C
6
H
3
-CH
2 2, 4-C1 2
-C
6
H
3
-CH
2 3, 5-C1 2
-C
6
H
3 -C1 2 2, 6-C1 2 -C6H 3
-CH
2 3, 4-C1 2
-C
6
H
3
-CH
2 2-CH 3 -c 6
H
4
-CH
2 ,0050/43960 32 37 4-CH 3 -1: 6
H
4
-CH
2 38 2,3-(CH 3 2
-C
6
H
3
-CH
2 39 2, 4- (CR 3 2
-C
6
H
3
-CH
2 2, 5-(CH 3 2
-C
6
H
3
-CH
2 41 3, 4-(CHi 3 2
-C
6
H
3
-CH
2 42 3, CR 3 2
C
6
H
3
-CH
2 43 4, CH 3 2
-C
6
H
3
-CH
2 44 2, 3,4- (CH 3 3
-C
6
H
2
-CH
2 2, 4, 5-(CH 3 3
-C
6
H
2
-CH
2 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 48 2-CF 3
-C
6
H
4
-CH
2 49 3-CF 3
-C
6
H
4
-CH
2 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 -C6H 3
-CH
2 2-CF 3 -5-CH 3
-C
6
H
3
-CH
2 56 2-C.H 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 59 4-Br-C 6
H
4
-CH
2 2- (isopropyl) -C 6
H
4
-CH
2 61 3- (isopropyl) -C 6
H
4
-CH
2 62 4- (isopropyl) )-C 6
H
4 -C1 2 63 2- (isopropyl) -3-C1-C 6
H
3
-CH
2 64 2- (isopropyl) -4-C-C 6
H
3
-CH
2 2- (isopropyl) -5-Cl-C 6
H
3
-CH
2 66 2-CH 3 isopropyl) -C 6
H
3
-CH
2 67 2-CH 3 isopropyl.) -C6H 3
-CH
2 68 2-CH 3 isopropyl.) -C 6
H
3
-CH
2 69 2-t-C 4
H
9
-C
6
H
4
-CH
2 3-tC 4
H-C
6
H
4
-CH
2 71 4-t-C 4
HI
9
-C
6 4
-CH
2 72 2-CH 3 -3-t-C 4
H-C
6
H
3
-CH
2 73 2-CH 3 -4-t-C 4
H-C
6
H
3
-CH
2 74 2-CH 3 -5-t-C 4
H-C
6
H
3
-CH
2 3-CH 3 -4-t-C 4
H-C
6
H
3
-CH
2 76 3-CH 3 5-t-C 4 H9-CGH 3
-CH
2 77 2-Cl-3-t-C 4
H-C
6
H
3
-CH
2 78 2-Cl-4-t-C 4
H-C
6
H
3
-CH
2 79 2-Cl-5-t-C 4
H-C
6
H
3
-CH
2 3-Cl-4-t-C 4
H-C
6
H
3
-H
2 81 3-Cl-5-t-C 4
H-C
6
H
3
-CH
2 82 2-OCH 3
-C
6
H
4
-CH
2 83 3-OCE1 3
-C
6
H
4
-CH
2 0050/43960 33 84 4-OCH!-C 6
H
4
-CH
2 2-CH 3 3-OCH 3
-C
6
H
3
-CH
2 86 2-CH 3 5-OCH 3
-C
6
H
3
-CH
2 87 3 -CH 3 4OCH 3
-C
6
H
3
-CH
2 88 3-CH 3 5-CH 3
-C
6
H
3
-CH
2 89 2--Cl- 2-0H 3
-C
6
H
3
-CH
2 2--C1-4-OCH 3
-C
6
H
3 -CHt 2 91 2-C1-E-CH 3
-C
6
H
3
-CH
2 92 2-OCH 3 -3-Cl-C 6
H
3
-CH
2 93 2-OCH 3 -4-C1-C 6
H
3
-CH
2 94 2-OCH 3 -5-C1-C 6
H
3
-CH
2 2 -CH 3 (cyclohexyl -C 6
H
3
-CH
2 96 2-CH 3 -4-(C6H-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 (methoxyiminomethyl.) -C 6
H
3
-CH
2 101 2-Methoxyiminmethy-C 6 4
-CH
4 102 3-Methoxyiminomethy-C 6
H
4
-CH
4 103 2-CH 3 (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-Pheny-C 6 4 Cl 2 107 2-Phenoxy-C 6
H
4
-CH
2 108 3-Phenoxy-C~fI 4
-CH
2 109 4-Phenoxy-C 6
H
4
-CH
2 110 2-Benzyloxy-C 6
H
4
-CH
2 ill 3 -Benz Yloxy-C 6
H
4
-CH
2 112 4-Benzyloxy-C 6
H
4
-CH
2 113 1-Naphthyl-CH 2 114 2-Naphthyl-CH 2 115 9-Anthryl-CH 2 116 2-CH 3 -:3-C 6 H!;0-C 6
H
3
-CH
2 117 2-CH 3 -4I-C 6
H
5 0-C6H 3
-CH
2 118 2-CH 3 -5-C 6
H
5 0-C 6
H
3
-CH
2 119 3-CH 3 4-C 6
H
5 0-C 6 1 3
-CH
2 120 4-CH 3 -5;-C 6
H
5 0-C 6
H
3
-CH
2 121 2-C1-3-C 6
H
5 0-C 6
H
3
-CH
2 122 2-C1-4-C 6 HS0-C 6
H
3
-CH
2 123 2-Cl-5-CH 5 0-CH 3
-CH
2 124 3 6
H
5 0-C 6
H
3 -CH2 125 3 6
H
5 0C 6
H
3
-CH
2 126 2-CH 3 -4-CO 2
CH
3 -C6H 3
-CH
2 127 2-CH 3 -4CO 2
CH
3
-C
6
H.
3
-CH
2 128 C 6
HS-CE(CH
3 129 2-F-C 6 11 4
-CH(CH
3 130 2-F-C 6 11 4 -CH (CH 3 0050/43960 34 131 4-F-C(,H 4 -CU (CH 3 132 2-CJ.-C 6
H
4
-CH(CFI
3 133 3-C1-C, 6
H
4 -CH( CU 3 134 4-Cl-C 6
H
4
-CH(CH
3 135 2, 3-C.
2
-C
6
U
3 -CU (CH 3 136 2, 4-C1- 2
-C
6
H
3 -CH (CU 3 137 2, 5-C1 2
-C
6
H
3 -CH (CH 3 138 2, 6-C1.
2
-C
6
H
3 -CR (CU 3 139 3, 4- CI- 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(CI1 3 142 4-CH 3
-C
6
H
4 -C CH 3 143 2, 3- (C 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- (C 3 2
-C
6
H
3 -CH (CH 3 146 3, 4- (CH 3 2
-C
6
H
3 -CH (CH 3 147 3, 5- (C 3 2
-C
6
H
3 -CH (CH 3 148 4, 5- (CH 3
-C
6
H
3 -CH (CH 3 150 2,3, 4- (C 3 3
-C
6
H
2 -CH (CH 3 151 2, 4,5- (C 3 3
-C
6
H
2 -CH (CH 3 152 2,4, 6- (C 3 3
-C
6 2 -CH (CH 3 153 2, 2,6- (CH 3 3
-C
6
H
2 -CH (CH 3 154 2-CF 3
-C
6
H
4 -CH( CU 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 (CU 3 158 2-CH 3 -4-CF 3
-C
6
H
3 -CH (CU 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 (CR 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
-CU(CU
3 163 2-Br--C 6
H
4
-CH(CH
3 164 3-Br-C 6
H
4 -CH (CU 3 165 4-Br-C 6
H
4
-CH(CH
3 166 2-(isopropyl)-C 6
H
4
-CH(CH
3 167 isopropyl)-C 6
H
4
-CH(CH
3 168 4- isopropyl.) -C 6
H
4 -CH( CU 3 169 2- isopropyl -3-C1-C 6
H
3 -CH (CU 3 170 2- isopropyl -4-Cl-C 6
H
3 -CH (CU 3 171 2- (isopropyl) -5-C--C 6
U
3 -CH (CH 3 172 2-CH 3 3- isopropyl -C 6
U
3 -CH (CU 3 173 2-CH 3 (isopropyl) -C 6
H
3 -CH (CU 3 174 2-CH 3 isopropyl.) -C 6
U
3 -CU (CU 3 175 2-t-C 4 H9-C 6 iH 4 -CU- (CU 3 176 3-t-C 4 H9-C 6
H
4 -CH- (CH 3 177 4-t-C 4
H
9
-C
6
U
4 -CH- (CU 3 178 2-CH 3 -3'-t-C 4 H9-C 6
H
3
-CH(CU
3 0050/43 960 179 2-CH 3 -4-t-C 4
H
9
-C
6
H
3 -CH (CR 3 180 2-C113--5-t-C 4 Hg-C 6
H
3 -CH (.CH 3 181 3-CH 3 -4-t-C 4 9
C
6
H
3
-CH(CH
3 182 3-CH 3 -5-t-C 4
H
9
-C
6
H
3 -CH (CH 3 183 2-C2-3-t-C 4
H
9
-C
6
H
3 -CH (CH 3 184 2-Cl-4-t-C 4 Hq-C 6
H
3 -CH (CH 3 185 3-'C1-4-t-C 4
H
9
-C
6
H
3 -CH (CH 3 187 3-Cl-S -t-C 4 Hq-C 6
H
3 -C CR 3 188 2-0CH 3
-C
6 E1 4
-CH
2 -CH (CH 3 189 3-OCH 3
-C
6
H
4
-CH
2 -CH (CH 3 190 4-OCEI 3
-C
6
H
4
-CH
2 -CH Cl 3 191 2-CH 3 3-OCH 3
-C
6
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
6
H
3 -CH (CH 3 194 3-CH 3 -5-C1 3
-C
6
H
3
-CR(CH
3 195 3-CH 3 -5-OCH 3
-C
6
H
3 -CH (CR 3 196 2-Cl-3-OCH 3
-C
6
H
3 -CH (CH 3 197 2-Cl-4-OCH 3
-C
6
H
3 -CH (CH 3 198 2-Cl-5-C1 3
-C
6
H
3
-CH(CH
3 199 2-OCH 3 -3-Cl-C 6
H
3
-CH(CH
3 200 2-QCH 3 -4-C1-C 6 1 3 -CH( CH 3 201 2-OCH 3 -5-C1-C 6
H
3
-CH(CH
3 202 2-CH 3 (cyclohexyl) -C 6
H
3 -CH (CH 3 203 2-CR 3 4-C 6
H
5
-C
6
H
3 -CR (CR 3 204 2-CH 3 3-Br-C 6
H
3 -CR (CH 3 205 2-CH 3 4-Br-C 6
H
3 -CH (CH 3 206 3-CH 3 -5-Br-C 6
H
3 -CH (CH 3 207 2-CH 3 3- (methoxyiminomethyl -C 6
H
3 -CH (CR 3 208 2-Methoxyirninomethyl-C 6
R
4 -CH CH 3 209 3-Methoxyixinomethyl-C 6
R
4 -C CH 3 210 2-CR 3 (methoxyiminomethyl -C 6
R
3 -CR (CR 3 211 2-PhenYl-C 6
H
4 -CH CR 3 212 3-PhenYl-C 6
H
4 -CH (CH 3 213 4-Phen Yl-C 6
R
4 -CH (CR 3 214 2-Phen OXY-C 6
H
4 -CH (CH 3 215 3-PhenOXY-C 6
H
4 -CH (CR 3 216 4-Phenoxy-C 6
H
4 -CR CH 3 217 2-BenzyloXY-C 6
R
4 -CH (CR 3 218 3-Benzyloxy-C 6
H
4 -CR (CR 3 219 4-BenzyloXY-C 6
H
4 -CR (CH 3 220 1-Naphthyl-CH(CR 3 221 2-Naphthyl-CR(CH 3 222 9-Anthryl-CR(CR 3 223 2-CR 3 -3-C 6
H
5 0-C 6
R
3 -CH (CH 3 224 2-CH 3 -4-CG 5
-C
6 3 -'CH (CR 3 225 2-CR 3 -5-C 6
H
5 0-C 6
H
3 -CR (CR 3 226 3-CH 3 -4-C 6
R
5 0-C 6
R
3 -CH (CH 3 0050/43960 36 227 4-CH 3 -5-CGH 5
O-C
6
H
3 -CH (CH 3 228 2-Cl-3-C 6
H
5 0-C 6
H
3 -CH (CH 3 229 2-C1-4-C 6
H
5 0-C 6
H
3 -CH(d11 3 2-Cl-5-C 6
H
5 O-C6H 3 -CH (CH 3 231 3-Cl-4-C6H 5
O-CGH
3 -CH CH 3 232 3-Cl-5 -C 6 H0-C 6
H
3 -CH (CH 3 233 2-CH3--4-CO 2
CH
3 -CgH 3 -CH( CH 3 234 2--11 3 5-CO 2
CH
3
-C
6
H
3 -CH (CH 3 235 C 6 Hs-(CH 2 2 236 2-F-C 6
H
4
-(CH
2 2 237 3-F-C 6
H
4
-(CH
2 2 238 4-F-C 6
H
4
-(CH
2 2 239 2-Cl-C' 6
H
4
(CH
2 2 240 3-C1-C: 6
H
4
(CH
2 2 241 4-Cl-C 6 11 4
(CH
2 2 242 2,3-Cl 2
-CGH
3
-(CH
2 2 243 2,4-C.
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 (d1 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-C6H 3
(CH
2 2 251 2, 3- (CH 3 2
-C
6 1 3 (CF1 2 2 252 2, 5- (CH 3 2
-C
6
H
3 (Ci 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 2,2,6-(CH 3 3
-C
6
H
2
-(CI
2 2 260 2-CF 3
-C
6
H
4
-(CH
2 2 261 2-CF 3
C
6
H
4 (C1 2 2 262 4-CF 3 6
H
4
CH
2 2 263 2-CH 3 -:3-CF 3
-C
6
H
3
(CB
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 B1 3
(CH
2 2 266 2-CF 3 -4-CH 3
-C
6
H
3
-(CH
2 2 267 2-CF 3 -3-CH 3
-C
6
H
3
CH
2 2 268 2-CH 3 -3I-CH 3
-C
6
H
3
(CH
2 2 269 2-Br-C;H 4
(CH
2 2 270 3-Br-C;H 4
(CH
2 2 271 4-Br--Ci;H 4
(CH
2 2 272 2- (isopropyl) -C6H 4
(CH
2 2 273 3- (is opropyl -C 6
H
4
CH
2 2 0050/43960 37 274 4- isopropyl -C 6
H
4 (Cl! 2 2 275 2- (isopropyl) -3-Cl-C 6
H
3
(CH
2 2 276 2-C isopropyl -4-C1-C 6
H
3 (Cl! 2 2 277 2- (isopropyl) -5-Cl-C 6 3 2 278 2-Cl! 3 (isopropyl) -C 6 3
(C!
2 2 279 2-C! 3 4- (isopropyl) -C 6 3
(CH
2 2 280 2-C! 3 (isopropyl) -C 6 l! 3
(CH
2 2 281 2-t-C 4 H9g-C 6 4
(C!
2 2 282 3-t-C 4
H
9 -CGl! 4
(CH
2 2 l0 283 4-t-C4 9
-C
6 4 2 2 284 2-CH 3 -3-t-C 4 Hg-C 6 l! 3
-(CH
2 2 285 2-CH 3 -4-t-C 4 Hg-C 6 3 -(Cl 2 2 286 2-Cl! 3 -5-t-C 4 9
-C
6
H
3 (Cl! 2 2 287 3-CH 3 -4-t-C 4 9
-C
6
H
3 (Cl! 2 2 288 3-Cl! 3 -5-t-C 4 Hg-C 6 l! 3
(CH
2 2 289 2-Cl-3-t-C 4 Hg-C 6
H
3 (Cl! 2 2 290 2-Cl-4-t-C 4 Hg-C 6
H
3 (Cl! 2 2 291 2-Cl-5-t-C 4 Hg-C 6 l! 3 (Cl! 2 2 292 3-Cl-4-t-C 4 9
-C
6
H
3 (Cl! 2 2 293 3-Cl-5-t-C 4 Hg-C 6 l! 3 (Cl! 2 2 294 2-OC! 3
-C
6 4 (Cl! 2 )2 295 3-0C1 3
-C
6 l! 4
(CH
2 2 296 4-OCl! 3
-C
6 l! 4 (Cl! 2 2 297 2-Cl! 3 3-OCl! 3
-C
6 3
(C!
2 2 298 2-Cl! 3 -4-OCl! 3
-C
6 l! 3
(C!
2 2 299 2-CH! 3 -5-OCl! 3
-C
6 l! 3 (Cl! 2 2 300 3-CH 3 -4-OCl! 3
-C
6 l! 3
(C!
2 2 301 3-CH 3 -5-OC! 3
-C
6 l! 3 (Cl! 2 2 302 2-Cl-3 -OCH 3
-C
6 l! 3
(C!
3 2 303 2-Cl-4 -OC! 3
-C
6
H
3
(C!
3 2 304 2-Cl-5 -0CH 3
C
6 l! 3 (Cl! 3 2 305 2-OCH3y-3-Cl-C 6
H
3
(C!
3 2 306 2-OCl! 3 -4-Cl-C 6 3
(C!
3 2 307 2-OCl! 3 -5-Cl-C 6
H
3 (Cl! 3 2 308 2-Cl!J-4- (cyclohexyl) -C 6 3
(C!
2 2 309 2-Cl! 3 -4-C 6 l! 5
-C
6
H
3 (Cl! 2 2 310 2-Cl! 3 -3-Br-C 6 l!3- (Cl! 2 2 311 2-CH 3 -4-Br-C 6 l! 3 (Cl! 2 2 312 2-CH 3 -5-Br-C 6 3 (Cl! 2 2 313 2-Cl! 3 (methoxyiminomethyl -C 6 l! 3 (Cl! 2 2 314 2-Methoxyiminomethyl-C 6 l! 4 (Cl! 2 2 315 3-Methoxyiminomethyl-C 6
H
4 (Cl! 2 2 316 2-Cl! 3 (methoxyiminomethyl.) -C 6 l! 3 (Cl! 2 2 317 2-Phenyl-C 6 4
-(CH
2 2 415 318 3-Phenyl-C 6 4 -(Cl! 2 2 319 4-Phenyl-C 6 4 2 2 320 2-Phenoxy-CsH 4 (Cl! 2 2 0050/43960 38 321 3-Phenoxy-C 6
H
4
(CH
2 2 322 4-PhenOXY-C 6
H
4
CH
2 2 323 2-Ben ZY10XY-C 6
H
4
(CH
2 2 324 2-Benzy1oXY-C 6 i 4
CH
2 2 325 4-Benzy1oXY--C 6
H
4
(CH
2 2 326 1 -Naphthyl- (CH 2 2 327 2-Naphthyl- Ch2 2 328 9-Anthiryl- (CH 2 2 329 2-CH3-3-C6IISO-C6H 3 (C1 2 2 330 2-CH 3 -4-C 6 h 5
O-C:
6
H
3
(CH
2 2 331 2-CH 3 -5-C 6
H
5 0-C 6
H
3
(CH
2 2 332 3-CH 3 -4-C 6
H
5 0-C 6
H
3
(CH
2 2 333 4-CH 3 -5C 6
HS
5 0C 6
H
3
(CH
2 )2 334 2-C1-3-C 6
H
5 0-C 6
H
3
(CH
2 2 335 2-C1-4-C 6 HS0-C 6
H
3
(CR
2 2 336 2-Cl-B-C 6
H
5 0-C 6
H
3
(CH
2 2 337 3-Cl-4-C 6
H
5
C
6 1 3
(CH
2 2 338 3-C1-5-C 6
H
5 0-C 6
H
3
(CR
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 -c7H=CH-CH 2 342 2-F-C 6
H
4
-CH=CH-CH
2 343 2-F-C 6
H
4
-CH=CH-CH
2 344 4-F-C 6 Ei 4
-CH=CH-CH
2 345 2-C1--C 6
H
4
-CH;=CH-CH
2 346 3-C1--C 6
H
4
-CH=CH-CH
2 347 4-Cl-C 6
H
4
-CH=CH-CH
2 348 2, 3-Cl 2
-C
6
H
3 -CH=CH-C1 2 349 7, 4-Cl 2
-C
6
H
3
-CH=CH-CH
2 350 2, "5-C 2
-C
6 3
-CH=CH-CH
2 351 2, 6-C1 2 -C6H 3
-CH=CH-CH
2 352 3 ,4-Cl 2
C
6 H3-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=CR--CH
2 355 4-CH 3
-C
6
H
4
-CHCHCH;
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 (CRH) 2
-C
6
H
3
-CH=CH-CH
2 359 3 4 (CR 3 2
-CGH
3
H=CH-CH
2 360 i, 5- (CH 3 2
-CH--CH=CH-CH
2 361 4, 5- (CH 3 2
-C
6
H
3
CH=CH-CH
2 362 2, 3, 4- ItCH 3 3
-C
6
H
2
-CH=CH-CH
2 363 2, 4, 5- 1,CH 3 3
-C
6
H
2
-CH=CH-CH
2 364 2, 4, -C 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 0050/43960 39 368 4-CF 3
-C
6
H
4 -Cl=CH-CH 2 369 2-CH 3 -3-CF 3
-C
6
H
3
-CH=CH-CH
2 37U 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
HS-(CH
2 3 376 C 6 Hs-('H 2 4 377 C 6
H
5
-CEI
2
CH=CH-CH
2 378 4-F-C 6
H
4 -CH=CH- (CH 2 2 379 CH 3 0-CO-CH 2 380 CH 3
CH
2 :J-CO-C0 2 381 CH 3
-CO-CH
2
-CH
2 382 t-C 4 F1 9
'-CO-CH
2 383 t-C 4
H
9 'D-CO- C2 384 t-C 4 HqO-CO-CH (CH 3 385 n-C 4 H9gO-CO-CH 2 386 iSO-C 4
H
9 0-CO-CH 2 387 n-C 3
H
7 0)-CO-CH 2 388 sec-C 4
H
9 0-COCH 2 389 C 6
H
5 -Co-C'H 2 390 2-CH 3
:Z
6
H
4 0-CO-C1 2 391 3-CH 3
-C:
6
H
4 C -CO-CH 2 392 4-CH 3
-CGH
4
CJ-CO-CH
2 393 2-Cl-C 6
H
4
O-CO-CH
2 394 3-Cl-C 6
H
4 0-CO-CH 2 395 4-Cl-C 6
H
4
-CO-CH
2 396 C 6
H
5
-C(CU
3
=CH-CH
2
CH
2 i 398 N CH 2 cI 399I'i 6"CH N CH 2 0050/43960
CH
3 N CH 2 CF3 402
NCH
Br 403 N CH 2 Br N 'GH 2
F
405 N -CH 2 406
'CH
N
OH
2 407
N
408 CN j CR 2 409 NI
H
N
4 1 0 I C H 0050/43960 41 CH3 411 Gl
NCH
2
CI
412 WI
H
CH
3 Br 4131
'N'CH
2 414 c
CH
3 N Gil 2 415
B
CH
3 N CH 2 3 416
CH
3 N CH 2
CH
3 417
CH
3 N Gi 2
CIF
3
CI
418
N'CH
2 ci 419 Cl N' CR 2 0050/43960 42 Cl Cl 4201 N CH 2 421 Cl' 7
CH
3 N CH 2
OCH
3 Cl 422 N CH 2
F
423 Cl N CH 2 Br 424 0 2 N N CH 2 425 07- CH 2 46CH 2 Cl 427 16 CH 2 428 F-I I CH 2
N
CH
2 429 0050/43960 43 430 FN- CH 2
(OH
3
CH
2 431 I~7 6B 3 432
OH
2 0 43
OH
2 2434 N. J- CH2 435 N. H 2 CH2 4 3 6 O H 2 O' H 2 438 1 N H 0
H
OH3 439 *Nl,
CH
OH
3 01 440
OH
0050/43960 44 cl CH 3 441 aH 0 442 ci-i7LCH 2
'H
443 ill~~ 444 ~f CH 2
CE
2 446 447 c 2
CI
48N IsCH 2
CI
449
CE
2 450 N CE 2 CE1 451 N. Gl 2 0050/43960 452 cL7J1.s...
0 453
CH
2 '7 11 454 CH N CH, CH3 Fj 45 C1 CN T
C[H
3 0 a 458 Nj CI 2
CH
3 0 CiH 460 CH 3
O
1% 303 61CH 3 7k 2 462 462 NC-CHi 2 0050/43960 46 463 t-BuO-CH 2
-CH=CH-CH
2 464 (CH 3 2 -C=CIl-CH 2
-CH
2 -C CH 3
=CH-CH
2 465 (CH 3 2
CH-C=CH-CH
2
-CH
2 -C CH3 =CH-CH 2 466 C 6
H
5
-O-CH(CH
3 )-C1 2 467 4-Cl-C: 6
H
4
-O-CH(CH
3 1s 0050/43960 Table 3
R
2 N N
I
6 Y1
OCH
3
C=N
O=C-NHCH
3 Compd. No.R 1 1 H 2 H 3 H 4 H
H
6 H 7 H 8 H 9 H
H
11 H 12 H 13 H 14 H
H
16 H 17 H 18 H 19 H
H
21 H 22 H 23 H 24 H
H
26 H 27 H 28 H 29 H
H
31 H 32 H 33 H 34 H
H
R
2
H
CHi 3 t-'C 4
H
9
CH
2
=CH-CH
2
CE
2 =C (-Cl )-CH 2
CE.
2
=C(CH
3
)-CH
2
CE
3
CH=CH-CH
2
HC=-CCH
2
CH
3
C=-C-CH
2 cy clo-C 6
H
1 1
C
6
H
5
-CH
2 2-F-C 6
H
4
-CH
2 3-F-C 6
H
4
-CH
2 4 -F-C 6
H
4
-CH
2 2-Cl-C 6
H
4
-CH
2 3-C1-C 6
H
4
-CH
2 4-Cl-C 6
H
4
-CH
2 2-Br-C 6
H
4
-CH
2 3-Br-C 6
H
4
-CH
2 4 -Br-C 6
H
4
-CH
2 2-CH 3
-C
6
H
4
-CH
2 3-CH 3
-C
6
H
4
-CH
2 4-C-H 3
-C
6
H
4
-CH
2 2-C-F 3
-C
6
H
4
-CH
2 3-^CF 3
-C
6
H
4
-CH
2 4-C-F3-CrH 4
-CH
2 2-i-C 3
H
7
-C
6
H
4
-CH
2 3- i-C 3
H
7
-C
6
H
4
-CH
2 4- i-C 3
H
7
-C
6
H
4
-CH
2 2-t-C 4 H9-C 6
H
4
-CH
2 3-t-C 4 H9-C 6
H
4
-CH
2 4--t-C 4 H9-C 6
H
4
-CH
2 2-CH 3 0-C 6
H
4
,-CH
2 3-CH 3 0-C 6
H
4
CH
2 4-CH 3 0-C(;H 4
-CH
2 0050/43960 48 36 H 2--Cyancl-C 6
H
4
-CH
2
H
37 H 3--Cyaro--C 6
H
4
-CH
2
H
38 H 4-Cyano-C 6
H
4
-CH
2
H
39 H 2-Nitro-C 6
H
4
-CH
2
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-C1 2
-C
6
H
3
-CH
2
H
44 H 3, 5-Cl 2
-C
6
H
3
H
45 H 2, 6-Cl 2
-C
6
H
3
-CH
2
H
46 H 2, 4- (CH 3 2 6
H
3
-CH
2
H
47 H 2,5-(CH 3 2 -C-1 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 1--Naphthyl-CH 2
H
51 H 2--Naphthyl-CH 2
H
52 H C 6
H
5
-CH(CH
3
H
53 H 2--C1-C 6
H
4
-CH(CH
3
H
54 H 3--Cl-C 6
H
4
-CH(CH
3
H
55 H 4-'Cl-C 6
H
4
-CH(CH
3
H
56 H 2--CH 3 -C6H 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-C 6
H
4
-CH(CH
3
H
62 H 2- t-C 4 H9-C 6
H
4 -CH (CH 3
H
63 H 3-t-C 4
H
9
-C
6
H
4 -CH (CH 3
H
64 H 4-t-C 4
H
9
-C
6
H
4 -CH (CH 3
H
65 H 2-CH 3
O-C
6
H
4
-CH(CH
3
H
66 H 3-CH 3
O-C
6
H
4
-CH(CH
3
H
67 H 4-CH 3
O-C
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
'7 0 H 4-Cyano-C 6
H
4 -CH (CH3) H 71. H 2, 4-C1 2
-C
6 1H1-CH (CH 3
H
72 H 3, 4-C 2
-C
6
H
3 -CH(CH3) 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 00C-CH 2
H
77 H C 2 1- 5 00C-CH 2
H
78 H i-C 3
H
7 00C-CH 2
H
79 H t-C 4 HqOOC-CH 2
H
80 H t-C 4 H9OOC-CH(CH 3
H
81 H N-=C-CH 2
H
82 H Cr,25CO-CH 2
H
*0050/43960 49 83 H Pyrid-2-yl-xnethyl H 84 H Pyrazin-2-yl-methyl H H Pyrimidin-2-yl-nethyj H 86 H Fur-2-yl-methyl H 87 H Pyrrol-2-y.-methyJ. H 88 H N-Methylpyrrol-2-ylmethyl H 89 H Thien-2-ylmethy3. H H IEsoxazol-5-ylmethyl H 91 H Thiazol-2-ylmethyl H 92 H Thiazol-5-ylmethyl, H 93 H Ox:azol-2-ylmethy. H 94 H Pyrazol-3-ylmethyl H H Benzofuran-2-ylnethyl H 96 H Irndol-2-ylmethyl H 97 H Irndol-3-ylmethyl H 98 H Benzothiazol-2-ylnethy. H 99 H Quinolin-2-ylmethyl H 100 H 4-C1-C 6
H
4 OCH (CH 3
-CH
2
H
101 CH 3 H H 102 CH 3
CE-
3
H
103 CH 3 t-'C 4 H9 H 104 CH 3
CI*.
2
=CH-CH
2
H
105 CE 3 C1 2 =C -CH 2
H
106 CH 3
C(CH
3
)-CH
2
H
107 CE 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 CE 3 CYClo-C 6
H
1 1
H
ill CH 3
C
6
H
5
-CH
2
H
112 CH 3 2-F-C 6
H
4
-CH
2
H
113 CH 3 3-F-C 6
H
4
-CH
2
H
114 CH 3 4-F-C 6
H
4
-CH
2
H
115 CE 3 2-C1-C 6
H
4
-CH
2
H
116 C43~ 3-C1-C 6
H
4
-CH
2
H
117 CH 3 4--C1-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 CE 3 3-CH 3
-C
6
H
4
-CH
2
H
123 CE 3 4-CH 3
-C
6
H
4
-CH
2
H
124 CE 3 2-CF 3
-C
6
H
4
-CH
2
H
125 CE 3 3-CF 3
-C
6
H
4
-CH
2
H
126 CH 3 4-CF 3
-CGH
4
-CH
2
H
127 CF 3 2-i-C 3
H
7
-C
6
H
4
-CH
2
H
128 CE 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
H
129 CE 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
H
0050/43960 130 CH 3 2--t-C 4
H
9
-C
6
H
4
-CH
2
H
131 CU 3 3-t-C 4 H9-C 6
H
4
-CH
2
H
132 CU 3 4-t-C 4
H
9
-C
6
U
4
-CH
2
H
133 CU 3 2-CH 3
O-C
6
H
4
-CH
2
H
134 CU 3 3-CH 3
O-C
6
H
4
-CH
2
H
135 CU 3 4--CH 3 O-C6H 4
-CH
2
H
136 CH 3 2--Cyano-C 6
H
4
-CH
2
H
137 CU 3 3-Cyano-C 6
H
4
-CH
2
H
138 CU 3 4-Cyano-C 6
H
4
-CH
2
H
139 CU 3 2--NitrO-C 6
U
4
-CH
2
H
140 CH 3 3--NitrO-C 6
H
4
-CH
2
H
141 CU 3 4-Nitro-CU-CH 2
H
142 CU 3 2,4-C 2
-C
6
H
3
-CH
2
H
143 CU 3 3,4-C 2
-C
6
U
3
-CH
2
H
.L44 CU 3 3, 5-C1 2
-C
6
U
3
-CH
2
H
145 CU 3 2, 6-Cl 2
-C
6
H
3
-CU
2
H
146 CU 3 2,4-(CU 3 2
-C
6
H
3
-CU
2
H
147 CU 3 2,5-(CH 3 2
-C
6
H
3
-CH
2
H
148 CU 3 3,4-(CH 3 2
-C
6
H
3
-CH
2
H
149 CU 3 3,5-(CH 3 2
-C
6
H
3
-CU
2
H
150 CU 3 1--Naphthyl-CH 2
U
151 CU 3 2--Naphthyl-CU 2
H
152 CU 3
C
6
H
5
-CH(CU
3
H
153 CU 3 2-C1-C 6
H
4
-CH(CH
3
H
154 CU 3 3-Cl-C 6
U
4
-CU(CH
3
H
155 CU 3 4-C1-C 6
U
4
-CH(CH
3
H
156 CU 3
CH
3
-C
6
U
4
-CU(CU
3
U
157 CU 3 3-CH 3
-C
6
U
4
-CH(CH
3
H
158 CU 3 4-CU 3
-C
6
U
4
-CU(CU
3
U
159 CU 3 2-CF 3
-C
6
U
4
-CH(CU
3
U
160 CU 3 3-CF 3
-C
6
U
4
-CH(CU
3
U
161 CU 3 4-CF 3
-C
6
U
4
-CH(CU
3
H
162 CU 3 2-t-C 4
U
9
-C
6
H
4 -CU (CU 3
H
163 CU 3 3-t-C 4
U
9
-C
6
H
4 -CH (CH 3
U
164 CU 3 4-t-C 4 Ug-C 6
H
4
-CU(CU
3
H
165 CU 3 2-CU 3
O-C
6
U
4
-CH(CH
3
U
166 CU 3 3-CU 3 0-C 6
H
4
-CH(CU
3
U
167 CU 3 4-CU 3
O-C
6
U
4
-CU(CU
3
H
168 CU 3 2-Cyano-C 6
U
4 -CU (CU 3
H
169 CU 3 3-Cyano-C 6
U
4
-CU(CH
3
U
170 CU 3 4-Cyano-C 6 4
-CU(CU
3
H
171 CU 3 2, 4-Cl 2
-C
6
H
3 -CU CU 3
U
172 CU 3 3,4-C1 2
-C
6
U
3
-CU(CH
3
U
173 CU 3 3, 5-C1 2
-C
6
H
3 -CH (CU 3
H
174 CU 3 2, 4- (C 3 2
-C
6
H
3 -CH (CU 3
U
175 CU 3 2,5-(CH 3 2
-C
6
H
3
-CH(CH
3
H
176 CU 3
CH
3 00C-CH 2
H
0050S/43960 51 177 CE 3
C
2
!H
5 00C-CH 2
H
178 CE 3 i--C 3
H
7 00C-CH 2
H
179 CE 3 t-C 4 Hq00C-CH 2
H
180 CE 3 t-C 4
H
9 00C-CH(CH 3
H
181 CE 3
N=-C-CH
2
H
182 CE 3 C(,H5CO-CH 2
H
183 CE 3 Pyrid-2-yl--methyl H 184 CE 3 Pyrazin-2-yl-methyl H 185 CE 3 Pyrimidin-2-yl-niethyl H 186 CE 3 Fur-2-yl-methy. H 187 CE 3 Pyrrol-2-yl-rnethyl H 188 CH 3 N--Methylpyrrol-2-ylmethyl H 189 CE 3 Thien-2-ylrethyl H 190 CE 3 Isoxazol-5-ylmethyl H 191 CE 3 Th~iazol-2-ylmethyl H 192 CE 3 Thiazol-5-ylmethy. H 193 CE 3 Oxazol-2-ylrnethyl H 194 CE 3 Pyrazol-3-ylmethyl H 195 CE 3 BEnzofuran-2-ylmethyl H 196 CE 3 Indol-2--ylmethyl H 197 CE 3 Indol-3-ylmethy. H 198 CE 3 Benzothiazol-2--ylmethyl H 199 CE 3 QtuinoJlin-2-ylmethyl H 200 CE 3 4-Cl-C 6
E
4 OCH (CE 3
)-CE
2
H
201 H H CE 3 202 H CH 3
CE
3 203 H t-C 4 H9 CE 3 2 04t H CH' 2
=CH-CE
2
CH
3 205 H CH 2 =C(-Cl)-CH 2
CE
3 206 H CH 2
=C(CE
3
)-CE
2
CE
3 207 H CH 3
CH=CH-CH
2
CH
3 208 H HC=-CCH 2
CE
3 209 H CH 3
C=-C-CH
2
CE
3 210 H CYClo-C 6
H
11
CE
3 211 H C 6 E1 5
-CH
2
CE
3 212 H 2-F-C 6
H
4
-CH
2
CE
3 213 H 3-F-C 6
H
4
-CH
2
CE
3 214 H 4-F-C 6
H
4
-CH
2
CE
3 215 H 2-Cl-C 6
H
4
-CE
2
CE
3 216 H 3-Cl-C 6
H
4
-CH
2
CE
3 217 H 4-Cl-C 6
H
4
-CE
2
CE
3 218 H 2-Br-C 6
H
4
-CH
2
CE
3 219 H 3-Br-C 6
E
4
-CE
2
CE
3 220 H 4'--9r-C 6
H
4
-CH
2
CH
3 221 H 2-CH 3
-C
6
E
4
-CH
2
CE
3 222 H 3-CH 3
-C
6
H
4
-CH
2
CE
3 223 H 4-CH 3
-C
6 iH 4
-CH
2
CE
3 0050/43960 52 224 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-i-C 3
H
7
-C
6
H
4
-CH
2
CH
3 229 Hi 4-i-C 3
H
7
-C
6
H
4
-CH
2
CH
3 230 H 2--t-C 4
H
9
-C
6
H
4
-CH
2
CH
3 231 H 3-t-C 4
H
9
-C
6 1 4
-CH
2
CH
3 232 H 4--t-C 4
H
9
'CGH
4
-CH
2
CH
3 233 H1 2-CH 3
O-C
6
H
4
-CH
2
CH
3 234 H 3-CH 3 0-C 6
H
4
-CH
2
CH
3 235 H 4-CH 3 O0-C.6H 4
-CH
2
CH
3 236 H 2-Cya-lo--ClH 4
-CH
2
CH
3 237 H 3--Cyano-C 6
H
4
-CH
2
CH
3 2$3 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-C 6
H
4
-CH
2
CH
3 241 H 4--Nitro-C 6
H
4
-CH
2
CH
3 242 H 2,4-C1 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-C1 2
-C
6
H
3
-CH
2
CH
3 2 5 H 2, 6-C1 2
-C
6
H
3
-CH
2
CH
3 246 H 2, 4- (CH 3 2
-CGH
3
-CH
2
CH
3 247 H 2,5-(CH 3 2
-C
6
H
3
-CH
2
CH
3 248 H 3,r4- (CH 3 2
-C
6
H
3 -CH2 CH 3 249 H 3,5-(CH 3 2
-C
6
H
3
-CH
2
CH
3 250 H 1-Naphthyl-CH 2
CH
3 251 H 2-Naphthyl-CH 2 CH3 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-CGH 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-t-C 4
H
9
-C
6
H
4 -CH (CH 3
CH
3 263 H 3-t-C4 9 g-C 6
H
4 -CH (CH 3
CH
3 264 H 4-t-C 4 H9-C 6
H
4 -CH (CH 3
CH
3 265 H 2-CH 3
O-C
6
H
4
-CH(CH
3
CH
3 266 H 3-CH 3
O-C
6
H
4
-CH(CH
3
CH
3 267 H 4-CH 3 0-C 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(CH3) CH 3 270 H 4-Cyano-CH 4 -CH (CH 3
CH
3 0050/43960 53 271 H 2, 4-Cl2-C 6
H
3 -CH(CH3) 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
OH
3 275 H 2, 5- (CH 3 2
-C
6
H
3 -CH (CH 3
CH
3 276 H CEH 3 00C-CH 2
CH
3 277 H C 2
H
5 000-CH 2
OH
3 278 H i-C 3
H
7 00C-CH 2
CR
3 279 H t-'C 4
H
9 00C-CH 2
CH
3 280 H t--C 4
H
9 00C-CH (CH 3
OH
3 281 H N-=C-CH 2
CH
3 282 li C 6
H
5
CO-CH
2
CH
3 283 H Pyrid-2-yl-methyl H 284 H PIyrazin-2-yl-methyl CH 3 285 H Pyrimidin-2-yl-methyl CH 3 286 H Fur-2-yl-xuethyl CH 3 287 H Pyrrol-2-yl-methyJ. CH 3 288 H N-Methylpyrrol-2-ylmethyl CH 3 289 H Thien-2-ylmethyl OH 3 290 H Isoxazol-5-ylmethyl CH 3 291. H Thiazol-2-ylmethyl OH 3 292 H Thiazol-5-ylmethyl CH 3 293 H oxazol-2-ylrnethyl CH 3 294 H Pyrazol-3-ylmethyl CH 3 295 H Benzofuran-2--ylmethyl CH 3 296 H Indol-2-ylmethyJ. CH 3 297 14 Indol-3-ylmethyl
CH
3 298 H Benzothiazol-2-ylmethyl CH 3 299 H Quinolin-2-ylmethyJ. CH 3 300 H 4-C1-C 6
H
4 0CH(CH 3
)-CH
2
CR
3 301 CHR 3 H CH 3 302 OH 3 CH3i CH 3 303 CH 3 t-C 4 H9 CH 3 304 CH 3
CH
2
=CH-CH
2
CH
3 305 OH 3
CH
2 =C -CH 2
CH
3 306 Cu 3
CH
2
=C(CH
3
)-CH
2
OH
3 307 OH 3
CH
3
CH=CH-CH
2
CH
3 308 CH 3
HC=-CCH
2
CR
3 309 OH 3
CH
3
C=-C-CH
2
OH
3 310 Cu 3 cyclo-C 6 Hii CR 3 311 OH 3 0 6 11 5
-CH
2
CH
3 332 OH 3 2-F-C 6
H
4 -0R 2
CH
3 313 CR 3 3-F-C 6
H
4
-CH
2
CR
3 3214 OH 3 4-F-C 6
H
4
-CH
2
CR
3 315 CH 3 2-Cl-C 6
H
4
-CH
2
OH
3 316 OH 3 3-"2.-CGH 4
-CH
2
CH
3 317 OH 3 4---C 6
H
4
-CH
2
CH
3 0050/43960 54 318 Cr1 3 2-Br-C 6 1 4
-CH
2
CH
3 319 CH 3 3-Br-C 6
H
4
-CH
2 Cr1 3 320 CE! 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 Cr1 3 323 CH 3 4-CH 3 -CGr1 4
-CH
2
CE!
3 324 CE! 3 2-CF 3
-C
6
H
4
-CH
2
CE!
3 325 CH 3 3--CF 3
-C
6
H
4
-CH
2 Cr1 3 326 CH 3 4-CF 3
-C
6
H
4
-CH
2
CH
3 327 CE! 3 2-i-C 3 7
-C
6
H
4
-CH
2
CH
3 328 CE! 3 3-i-C 3
H
7
-C
6 4 -CH2 Cr1 3 329 Cr1 3 4-i-C 3 7
-C
6
H
4
-CH
2
CH
3 330 CE! 3 2-t-C 4
H
9
-C
6
H
4
-C!
2
CH
3 331 Cr1 3 3-t-C 4 Hg-C 6
H
4 -C1 2 Cr1 3 332 CE! 3 4-t-C 4 9
-C
6 1 4
-CH
2
CE!
3 333 CE! 3 2-CE! 3 0-C 6
H
4
-CH
2 Cr1 3 334 CE! 3 3-CH 3
O-C
6
H
4
-CE!
2 Cr1 3 335 Cr1 3 4-CH 3
O-C
6
H
4
-CE!
2
CE!
3 336 Cr1 3 2-Cyano-C 6 4
-CH
2 Cr1 3 337 Cr1 3 3-Cyano-C 6 4 -C!2 Cr1 3 338 CE! 3 4-Cyano--C 6
E!
4
-CH
2
CE!
3 339 Cr1 3 2-Nitro-C 6 i 4
-CH
2 Cr1 3 340 CH 3 3-Nitro-C 6 4
-C!
2
CE!
3 341 Cr1 3 4-N'itro-C 6 4
-C
2 Cr1 3 342 Cr1 3 2, 4-C 2
-C
6 3
-CH
2 Cr1 3 343 Cr1 3 3, 4-C 2
-C
6 3 -C1 2 Cr1 3 344 Cr1 3 3, 5-C 2
-C
6
H
3
-C!
2
CE!
3 345 Cr1 3 2, 6-Cl 2
-C
6
H
3
-CE!
2
CE!
3 346 Cr1 3 2, 4- (C! 3 2
-C
6 3
-C!
2
CE!
3 347 Cr1 3 2, 5- (C! 3 2
-C
6 3
-C!
2
CE!
3 348 Cr1 3 3, 4- (C! 3 2
-C
6 3
-CH
2
CE!
3 349 Cr1 3 3, 5 (Cr1 3 2
-C
6 r1 3 -C1 2 Cr1 3 350 Cr1 3 1-Naphthyl-C! 2 Cr1 3 351 Cr1 3 2-Naphthyl-C! 2 Cr1 3 352 CE! 3
C
6
E!
5
-CE!(CH
3
CE!
3 353 CE! 3 2-Cl-C 6 4
-C!(CI
3
CE!
3 354 Cr1 3 3-Cl-COE 4 -Cr1 CH 3
CE!
3 355 CE! 3 4-Cl-C 6 4 -CH (C! 3
CE!
3 356 CE! 3 2-CH 3
-C
6 4 -CH (C! 3
CE!
3 357 CE! 3 3-C! 3
-C
6
E!
4 3
CE!
3 358 CE! 3 4-C! 3
-CE!
4
CE!
3 359 CE! 3 2-CF 3
-C
6 4 3 Cr1 3 360 Cr1 3 3-CF 3
-C
6
H
4
-C!(CH
3
CE!
3 3 61 CE! 3 4-CF 3
-CGH
4
-CH(CH
3
CE!
3 352 CE! 3 2-t-C41 9
-C
6
H
4 -CH (C! 3
CE!
3 363 CE! 3 3-t-C 4
H
9
-C
6
H
4 -CH (C! 3
CE!
3 364 CE! 3 4- t-C 4 9
-C
6
E!
4 -CH (CH 3
CE!
3 0050/43960 365 CE 3 2-CH 3
O-C
6
H
4
-CH(CH
3
CH
3 366 CH 3 3--(H 3
-C
6
H
4 -CH (CH 3
CH
3 367 CE 3 4--CH 3
-C
6
H
4
-CH(CH
3
CR
3 368 CE 3 2--Cyanc-,C 6
H
4 -CH (CH 3
CH
3 369 CE 3 3--Cyano-C 6
H
4 -CH (CH 3
CR
3 370 CE 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 CE 3 3, 4-C1 2
-C
6
H
3 -C CH 3
CH
3 3 73 CH 3 3,5-C1 2
-C
6
H
3
-CH(CH
3
CH
3 374 CE 3 2, 4- (C 3 2
-C
6
H
3 -CH (CH 3
CH
3 375 CE 3 2, 5- (CE 3 2
-C
6
H
3 -CH CR 3
CH,
376 CE 3
CH-
3 00C-CH 2
CH
3 377 CE 3
C
2 HS00C-CH 2
CH
3 378 CH 3 i-C 3
H
7 00C-CH 2
CH
3 379 CE 3 t-C 4 Hq00C-CH 2
CH
3 380 CE 3 t-C 4
H
9 00C-CH(CH 3
CH
3 381 CE 3
N=-C-CH
2
CH
3 382 CE 3
C
6
H
5 C0-CE 2
CH
3 363 CE 3 Pyrid-2-yl-niethyl CR 3 384 CE 3 Pyrazin-2-yl-mxethyl CH 3 385 CE 3 Pyrimidin-2-yl-methyl CR 3 386 CE 3 Fur-2-yl-methyl CH 3 387 CE 3 Pyrrol-2-yl-methyl CH 3 388 CE 3 N-Methylpyrrol-2-ylmethyl CR 3 389 CE 3 Thien-2-ylmethyl CR 3 390 CE 3 Isoxazol-5-ylmethyl CH 3 391 CE 3 Thiazol-2-ylmethyl CR 3 392 CE 3 Thiazol-5-ylmethyl CH 3 393 CE 3 Oxazol-2-ylxnethyl CR 3 394 CE 3 Pyrazol-3-ylmethyl CH 3 395 CE 3 Benzofuran-2-ylmethyl CR 3 396 CH 3 Indol-2-ylmethyl CH 3 397 CE 3 Indol-3-yJlmethyl CR 3 398 CE 3 Benz othiazol- 2-ylmethy. CH 3 399 CE 3 Quinolin-2-ylmethyl CH 3 400 CE 3 4-Cl-C 6
E
4
OCR(CH
3
)-CR
2 1 (050/43960 Table 4
R
2 0.N
OCH
3 O=C
NHR
4 Compd. No.R 1 is51 H 2 H 3 H 4 H
H
6 H 7 H 8 H 9 H
H
11 H 12 H 13 H 14 H
H
16 H 17 H 18 H 19 H
H
21 H 22 H 23 H 24 H
H
26 H 27 H 28 H 29 H
H
31 H 32 H 33 H
H
CH
3 t-C 4
H
9
CH
2
=CH-CH
2
CH
2 =C -CH 2
CH
2 =C (CH 3
)-CH
2
CH
3
CH=CH-CH
2
HC=-CCH
2
CH
3 C=-C-CHi 2 CYClo-C 6
H
1 1
C
6
H
5
-CH
2 2-F-C 6
H
4
-CH
2 3-F-C 6
H
4
-CH
2 4-F-C 6
H
4
-CH
2 2-Cl-C 6
H
4
-CH
2 3-Cl-C 6
H
4
-CH
2 4-Cl-C 6
H
4
-CH
2 2-Br-C 6
H
4
-CH
2 3-Br-C 6
H
4
-CH
2 4-Br-C 6
H
4
-CH
2 2-CH 3
-C
6
H
4
-CH
2 3-CH 3
-C
6
H
4
-CH
2 4-CH 3
-C
6
H
4
-CH
2 2-CF 3
-C
6
H
4
-CH
2 3-CF 3
-C
6
H
4
-CH
2 4-CF 3
-C
6
H
4
-CH
2 2-i-C 3
H
7
-C
6
H
4
-CH
2 3-i-C 3
H
7
-C
6
H
4
-CH
2 4-i-C 3
H
7
-C
6
H
4
-CH
2 2-t-C 4 H9-C 6
H
4
-CH
2 3-t-C 4
H
9
-C
6
H
4
-CH
2 4-t-C 4 Hq-CGH 4
-CH
2 2-CH 3
O-C
6
H
4
-CH
2 0050/43960 57 34 H 3--CH 3 0-C 6
H
4
-CH
2
H
H 4-CH 3
O-C
6
H
4
-CH
2
H
36 H 2-Cyano-C 6
H
4
-CH
2
H
37 H 3-Cyano-C 6
H
4
-CH
2
H
38 H 4-Cyano-C 6
H
4
-CH
2
H
39 H 2-Nitro-C 6
H
4
-CH
2
H
H 3-Nitro-C 6
H
4
-CH
2
H
41 H 4-Nitro-C 6 1 4
-CH
2
H
42 H 2,4-C 2
-C
6
H
3
-CH
2
H
43 H 3,4-Cl 2
-CGH
3
-CH
2
H
44 H 3,5-C 2
-C
6
H
3
-CH
2
H
H 2,6-C 2
-C
6
H
3
-CH
2
H
46 H 2,4-(CH 3 2
-C
6
H
3
-CH
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
H 1-Naphthyl-CH 2
H
51 H 2-Naphthyl-CH 2
H
52 H C 6
HS-CH(CH
3
H
53 H 2-Cl-C 6
H
4
-CH(CH
3
H
54 H 3-C1-C 6
H
4
-CH(CH
3
H
H 4-Cl-C 6
H
4
-CH(CH
3
H
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
H 3-CF 3
-C
6
H
4
-CH(CH
3
H
61 H 4-CF 3 -C6H 4
-CH(CH
3
H
62 H 2-t-C 4
H
9
-C
6
H
4
-CH(CH
3
H
63 H 3-t-C 4 Hq-C 6
H
4
-CH(CH
3
H
64 H 4-t-C 4 H9-C 6
H
4
-CH(CH
3
H
H 2-CH 3
O-C
6
H
4
-CH(CH
3
H
66 H 3-CH 3
O-C
6
H
4
-CH(CH
3
H
67 H 4-CH 3
O-C
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
H 4-CyanO-C 6
H
4 -CH (CH 3
H
71 H 2,4-C 2
-C
6
H
3
-CH(CH
3
H
72 H 3,4-C 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 -C1 3 -CH (CH 3
H
H 2, 5- (CH 3 2
-C
6
H
3 -CH (CH 3
H
76 H CH 3 00C-CH 2
H
77 H C 2 H1 5 00C-CH 2
H
78 H i-C 3
H
7 00C-CH 2
H
79 H t-C 4 H9OOC-C '.H H t-C 4
H
9 00C-CH(CH 3
H
.0050/43960 58 81 H N=-C-CH 2
H
82 H C 6
HSCO-CH
2
H
83 H Pyrid-2-yl-methyl H 84 H Pyrazin-2-yl-methyJ. H 85 H Pyrimidin-2-yl-methyl H 86 H Fur-2-yl-niethyl H 87 H Pyrrol-2-yl-methyl H 88 H N-Methylpyrrol-2-ylmethy2. H 89 H Thien-2-ylxuethyl H 90 H Isoxazol-5-ylmethyl H 91 H Thiazol-2-ylmethyl H 92 H Thiazol-5-ylmethyl H 93 H Oxazol-2-ylinethyl H 94 H Pyrazol-3-ylmcG hyl H 95 H Benzofuran-2-ylmethy. H 96 H Indol-2-ylmethyl H 97 H Indol-3-ylmethy. H 98 H Benzothiazol-2-ylmethyl H 99 H Qcuinolin-2-ylmethyl H 100 H 4-C1-C 6
H
4 OCH (CH 3
-CH
2
H
101 CF! 3 H H 102 CF! 3
CH
3
H
103 CH 3 t-C 4 H9 H 104 CF! 3
CH
2
=CH-CH
2
H
105 CF! 3
CH
2 =C(-C1)-CH 2
H
106 CF! 3 C (CH 3
-CH
2
H
107 CF! 3
CH
3
CH=CH-CH
2
H
108 CF! 3
HC=-CCH
2
H
109 CH 3
CH
3
C=-C-C!
2
H
110 CF! 3 CYC1O-C 6
H
1 1
H
il1 CF! 3
C
6
H
5
-CH
2
H
112 CF! 3 2-F-C 6 4
-CH
2
H
113 CF! 3 3-F-C 6
H
4
-CF!
2
H
114 CF! 3 4-F-C 6
H
4
-CH
2
H
115 CH 3 2-Cl-CGH 4
-CH
2
H
116 CF! 3 3-C1-C 6
H
4
-CH
2
H
117 CH 3 4-C1-C 6
H
4
-CH
2
H
118 CF! 3 2-Br-CGF! 4
-CH
2
H
119 CH 3 3-Br-C 6
H
4
-CF!
2
H
120 CH 3 4-Br-C 6
H
4
CH
2
H
121 CF! 3 2-CH 3
-C
6
H
4
-CF!
2
H
122 CH 3 3-CH 3
-C
6
H
4
-CF!
2
H
123 CF! 3 4-CH 3 -CrH 4
-CH
2
H
124 CH 3 2-CF 3
-C
6 2 -CH- 2
H
125 CF! 3 3 C F 3 -C 6 H4- C'11 2
H
126 CH 3 4-CF 3
-C
6
H
4
-CH
2
H
127 CF! 3 2-i-C 3
F!
7
-C
6
F!
4
-CF!
2
H
.0050/43960 59 128 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
H
129 CH 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
H
130 CH 3 2-t-C 4
H
9
-C
6
H
4
-CH
2
H
131 CU 3 3--t-C 4 H9-C 6
H
4
-CH
2
H
132 CH 3 4--t-C 4
H
9
-CGH
4
-CH
2
H
133 CU 3 2--CH 3 0-C 6
H
4
-CH
2
H
134 CU 3 3--CH 3 0-C 6
U
4
-CH
2
H
135 CU 3 4-CU 3
O-C
6
U
4
-CH
2
H
136 CU 3 2--Cyano-C 6
H
4
-CH
2
H
137 CU 3 3-.Cyano-C 6
H
4
-CH
2
H
138 CH 3 4-Cyano-C 6
H
4
-CH
2
H
139 CU 3 2--Nitro-C 6
H
4
-CU
2
H
140 CU 3 3-Nitro-C 6
H
4
-CU
2
H
141 CH 3 4-'Nitro-C 6
H
4
-CH
2
H
142 CH 3 2, 4-C 2
-C
6
H
3
-CH
2
H
143 CH 3 3, 4-Cl 2
-C
6
H
3
-CH
2
H
144 CU 3 3,5-C 2
-C
6
H
3
-CH
2
H
145 CU 3 2, 6-Cl 2
-CGH
3
-CU
2
H
146 CU 3 2,4-(CH 3 2
-C
6
H
3
-CH
2
U
147 CU 3 2,5-(C 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 CU 3 3,5-(CH 3 2
-C
6
H
3
-CH
2
H
150 CU 3 1-Naphthyl-CH 2
H
151 CU 3 2-Naphthyl-CH 2
H
152 CU 3 CG6 5
-CH(CH
3
H
153 CU 3 2-Cl-C 6
H
4
-CH(CH
3
H
154 CU 3 3-Cl-C 6
H
4
-CH(CH
3
H
155 CU 3 4-C1--C 6
H
4
-CH(CU
3
H
156 CU 3
CH
3
-C
6
H
4
-CH(CH
3
H
157 CU 3 3-CU 3
-C
6
H
4
-CH(CH
3
H
158 CU 3 4-CH 3
-C
6
H
4
-CH(CH
3
H
159 CU 3 2-CF 3
-C
6 4 -CH (CU 3
U
160 CU 3 3-CF 3
-C
6
H
4
-CH(CH
3
U
161 CU 3 4-CF 3
-C
6
H
4
-CU(CU
3
H
162 CU 3 2-t-C 4 H9-C 6
H
4 -CH (CH 3
H
163 CU 3 3-t-C 4
H
9
-C
6
H
4 -CH (CH 3
H
164 CU 3 4-t-C 4 Ug-C 6
H
4 -CU (CH 3
H
165 CU 3 2-CH 3
O-C
6
U
4
-CH(CH
3
H
166 CU 3 3-CH 3
O-C
6
H
4 -CH (CH 3
H
167 CU 3 4-CH 3
O-C
6
H
4 -CH (CU 3
H
168, CU 3 2-Cyano-C 6
H
4
-CH(CH
3
U
169 CU 3 3-Cyano-C 6
H
4
-CU(CH
3
H
170 CU 3 4-Cyano-C 6
U
4 -CU(CH3) H 171 CU 3 2, 4-Cl 2
-C
6
H
3 -CU (CU 3
U
172 CU 3 3, 4-C 2
-C;H
3
-CU(CU
3
H
173 CU 3 3, 5-Cl 2
-C
6
U
3 -CU (CU 3
U
174 CU 3 2,4-(CU 3 2
-C
6
H
3
-CU(CH
3
U
0050/43960 175 CH 3 2, 5- (CH 3 2
-C
6
H
3 -CH (CH 3
H
176 CH 3
CH
3 00C-CH 2
H
177 CH 3
C
2
H
5 00C-CH 2
H
178 CH 3 i-'C 3
H
7 00C-CH 2
H
179 CH 3 t-C 4 Hq00C-CH 2
H
180 CH 3 t-'C 4 H9OOC-CH(CH 3
H
181 CH 3
N-==C-CH
2
H
182 CH 3
C
6
HSCO-CH
2
H
183 CH 3 Pyrid-2-yl-methyl H 184 CH 3 Pyrazin-2-yl-methyl H 185 CH 3 Pyrimidin-2-yl-methyl H 186 CH 3 Ftr-2-yl-methyl H 187 CH 3 Pyrrol-2-yl-methyl H 188 CH 3 N-Methylpyrrol-2-ylmethyl H 189 CH 3 Thien-2-ylnethyl H 190 CH 3 Isoxazol-5-ylmethyJ. H 191 CH 3 T~iazol-2-ylmethyl H 192 CH 3 Thiazol-5-ylmethyl H 193 CH 3 oxazol-2-ylxnethyl H 194 CH 3 Pyrazol-3-y..rethyl H 195 CH 3 Benzofuran-2-yimethyl H 196 CH 3 Indol-2-ylmethyJ. H 197 CH 3 Indol-3-ylmethyl H 198 CH 3 Benzothiazol-2-ylmethyJ. H 199 CH 3 Quinolin-2-ylmethyl H 200 CH 3 4-Cl--C 6
H
4
OCH(CH
3
)-CH
2
H
201 H H C 2
H
202 H CH 3
C
2
H
203 H t-C 4 Hq C 2
H
5 204 H CH 2
=CH-CH
2
C
2
H
205 H CH 2 =C(-Cl)-CH 2
C
2
H
206 H CH 2
=C(CH
3
)-CH
2
C
2
H
207 H CH 3
CH=CH-CH
2
C
2
H
208 H HC-=CCH 2 C2H 209 H CH 3
C=-C-CH
2
C
2
HS
210 H CYClo-C 6
H
1 1
C-H
211 H C 6
H
5
-CH
2
C
2
H
212 H 2-F-C 6
H
4
-CH
2
C
2
H
213 H 3-F-C 6
H
4
-CH
2
C
2
H
214 H 4-F-C 6
H
4
-CH
2
C
2
H
215 H 2-Cl-C 6
H
4
-CH
2
C
2
H
216 H 3-Cl-C 6
H
4
-CH
2
C
2
H
217 H 4-Cl-C 6
H
4
-CH
2
C
2
HS
218 H 2-Br-C 6
H
4
-CH
2
C
2
H
219 H 3-Br-C 6
H
4
-CH
2
C
2
H
220 H 4-Br-C 6
H
4
-CH
2
C
2
HS
221 H 2-CH 3
-C
6
H
4
-CH
2
C
2
H
0050/43960 61 222 H 3-'CH 3
-C
6
H
4
-CH
2
C
2
H
223 H 4-CH 3
-C
6
H
4
-CH
2
C
2
H
224 H 2--CF 3
-C
6
H
4
-CH
2
C
2
H
225 H 3-CF 3
-C
6
H
4
-CH
2
C
2
H
226 H 4--CF 3
-C
6
H
4
-CH
2
C
2
H
227 H 2-4i-C 3
H
7
-C
6
H
4
-CH
2
C
2
HS
228 H 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
229 H 4-'i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
230 H 2-'t-C 4 H9-C 6
H
4
-CH
2
C
2
H
231 H 3-t-C 4 HS, -C 6
H
4
-CH
2
C
2
H
232 H 4-'t-C 4
H
9
-C
6
H
4
-CH
2
C
2
HS
233 H 2-CH 3
O--C
6
H
4
-CH
2
C
2
H
234 H 3-CH 3
O-C
6
H
4
-CH
2
C
2
H
235 H 4--CH 3
O-C
6
H
4
-CH
2
C
2
H
236 H 2-Cyano-C 6
H
4
-CH
2
C
2
H
237 H 3--CyanO-C 6
H
4
-CH
2
C
2
H
238 H 4-.Cyano-C 6
H
4
-CH
2
C
2
H
239 H 2-NitrO-C 6
H
4
-CH
2
C
2
HS
240 H 3-Nitro-C 6
H
4
-CH
2
C
2
H
241 H 4-Nitro-C 6
H
4
-CH
2
C
2
H!;
242 H 2,4-C1 2
-C
6
H
3
-CH
2
C
2
H
243 H 3, 4-C1 2
-C
6 8 3
-CH
2
C
2
H
244 H 3,5-C.
2
-C
6
H
3
-CH
2
C
2
H
245 H 2, 6-Cl 2
-C
6
H
3
-CH
2
C
2
H
246 H 2, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
247 H 2,5-(CH 3 2
-C
6
H
3
-CH
2
C
2
H
248 H (CH 3 2
-CGH
3
-CH
2
C
2
H
249 H 3,5-(CH3) 2
-C
6
H
3
-CH
2
C
2
H
250 H 1-Naphthyl-CH 2
C
2
H
251 H 2-N'aphthyl-CH 2
C
2
H
252 H C 6
HS-CH(CH
3
C
2
H
253 H 2-C1-C 6
H
4 -CH(CH3) C 2
H
254 H 3-C1-C 6
H
4
-CH(CH
3
C
2
H
5 i 255 H 4-C1-C 6
H
4
-CH(CH
3
C
2
H
256 H 2-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
257 H 3-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
258 H 4-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
5 i 259 H 2-CF 3 -CrH 4
-CH(CH
3
C
2
HS
260 H 3-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
261 H 4-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
262 H 2-t-C 4
H
9
-C
6
H
4 -CH (CH 3
C
2
H
263 H 3-t-C 4
H
9
-C
6
H
4
-CH(CH
3
C
2
HS
264 H 4-t-C 4 H9-C;H 4 -CH (CH 3
C
2
H
265 H 2-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
266 H 3-CH3O-C 6
H
4
-CH(CH
3
C
2
H
267 H 4-CH 3
O-C
6
H
4
-CH(CH
3
C
2
HS
268 H 2-Cyano-C 6
H
4
-CH(CH
3
C
2
HS
0050/43960 62 269 H 3-Cyano-C 6
H
4
-CH(CH
3
C
2
H_
270 H 4--Cyano-C 6
H
4 -CH (CH 3
C
2
H
271 H 2 ,4-C 2
-C
6
H
3
-CH(CH
3
C
2
H
272 H 3, 4-Cl 2
-C
6
H
3
-CH(CH
3
C
2
H
273 H 3, 5-C 2
-C
6
H
3
-CH(CH
3
C
2
H
274 H 2, 4- (CH 3 2
-C
6
H
3 -CH (CH 3
C
2
H
275 H 2, 5-(CH 3
)-C
6
H
3
-CH(CH
3
C
2
H
276 H CE 3 00C-CH 2
C
2
H
277 H C 2
H
5 00C-CH 2
C
2
H
278 H i-C 3
H
7 00C-CH 2
C
2 279 H t- C 4
HOOC-CH
2
C
2 280 H t-C 4 H9OOC-CH(CH 3
C
2
H
281 H N=-=C-CH 2
C
2
)H
282 H C 6
H
5
CO-CH
2
C
2
H
283 H Pyrid-2-yl-methyl C 2
H
284 H Pyrazin-2-yl-methyl C 2
H
285 H Pyrimidin-2-yl-nethyl. C 2
H
286 H Fur-2-yl-methyl C 2
H
287 H Pyrrol-2-yl-methyJ. C 2
HS
288 H N-Methylpyrrol-2-ylxuethyl C 2
H
289 H Thien-2-ylmethyJ. C 2
H
290 H Isoxazol-5-ylmethy2. C 2
H
291 H Thiazol-2-ylmethyJ. C 2
H
292 H Thiazol-5-ylnethyl C 2
H
293 H oxazol-2-ylmethyl C 2
H
294 H Pyrazol-3-ylmethyl C 2
H.
295 H Benzofuran-2-ylme thyl C 2
H
296 H Indol-2-ylmethyl C 2
H
297 H Indol-3-yJlmethyl C 2
H
298 H Benzothiazol-2-ylmethyJ. C 2
H
299 H Quinolin-2-ylmethyl C 2
H
300 H 4-Cl-CGH 4 0CH (CH 3
-CH
2
C
2
H
301 CH 3 H C 2
H
302 CH 3
CH
3
C
2
HS
303 CH 3 t-C 4
H
9
C
2
H
304 CH 3
CH
2
=CH-CH
2
C
2
HS
305 CH 3
CH
2 =C(-C1)-CH 2
C
2
H
306 CH 3
CH
2
=C(CH
3
)-CH
2
C
2
H
307 CH 3
CH
3 CH=CH-CH,? C 2
H
308 CH3 HC=-CCH 2
C
2
HS
309 CH 3
CH
3
C=-C-CH
2
C
2 310 CH3 CYC1o-C 6
H
1 1
C
2
H
311 CH 3
C
6 1-CH 2
C
2
H
332 CH 3 2-F-C6H 4
-CH
2
C
2
H!
313 CH 3 3-F-C 6
H
4
-CH
2
C
2
H
314 CH 3 4-F-C 6
H
4
-CH
2
C
2
H
315 CH 3 2-C1-C 6
H
4
-CH
2
C
2
H
0050/43960 63 316 CH 3 3-C1-C 6
H
4
-CH
2
C
2
H
317 CH 3 4-Cl-C 6
H
4
-CH
2
C
2
H
318 CH 3 2-Br-C 6
H
4
-CH
2
C
2
H
319 CH 3 3-Br-C 6
H
4
-CH
2
C
2
H
320 CH 3 4-Br-CGH 4
-CH
2
C
2
H
321 CH 3 2--CH3-C 6
H
4
-CH
2
C
2
H
322 CH 3 3--CH 3
-C
6
H
4
-CH
2
CH
323 CH 3 4-CH 3
-C
6
H
4
-CH
2
C
2
H
324 CH 3 2-CF 3
-C
6
H
4
-CH
2
C
2
H
325 CH 3 3-CF 3
-C
6
H
4
-CH
2
C
2
H
326 CH 3 4-CF 3 -C4-1 4
-CH
2
C
2
H
327 CH 3 2-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
328 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
329 CH 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
330 CU 3 2-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
HS
331 CH 3 3-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
HS
332 CH 3 4-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
H
333 CH 3 2-CH 3
O-C
6
H
4
-CH
2
C
2
H_
334 CU 3 3-CH 3
O-C
6
H
4
-CH
2
C
2
H
335 Cl1 3 4-CH 3
O-C
6
H
4
-CH
2
C
2
H
336 CU 3 2-Cyano-C 6
H
4
-CH
2
C
2
H
337 CH 3 3-Cyano-C 6
H
4
-CH
2
C
2
H
338 CH 3 4-Cyano-C 6 1 4
-CH
2
C
2
H
339 CH3 2-Nitro-C 6
H
4
-CH
2
C
2
H
340 CH 3 3'-Nitro-C 6
H
4
-CH
2
C
2
H
341 CU 3 4-Nitro-C 6
H
4
-CH
2
C
2
H
342 CU 3 2, 4-Cl 2
-C
6
H
3
-CH
2
C
2
H
343 CH 3 3, 4-C1 2
-C
6
H
3
-CH
2
C
2
H
344 CU 3 3, 5-Cl 2
-C
6
;H
3
-CH
2
C
2
H
345 CU 3 2,6-C 2
-C
6
H
3
-CH
2
C
2
H
346 CU 3 2, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
347 CH3 2, 5- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
348 CH 3 3,4-(CH 3 2
-C
6
H
3
-CH
2
C
2
H
39C 3 3, 5- (CU 2
C
6
H
3
-CH
2
C
2
H
350 CU 3 1-Naphthyl-CH 2
C
2
H
351 CU 3 2-Naphthyl-CH 2
C
2
H
352 CU 3
C
6
HS-CH(CH
3
C
2
H
353 CU 3 2-Cl-C 6
H
4
-CH(CH
3
C
2
H
354 CU 3 3-C1-C 6
H
4
-CH(CH
3
C
2
H-
355 CH 3 4-Cl-C 6
H
4
-CH(CH
3
C
2
H
356 CH 3 2-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
357 CU 3 3-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
358 CH 3 4-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
359 CH 3 2-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
360 CU 3 3-CF 3
-C
6 4
-CH(CH
3
C
2
H
361 CU 3 4-CF 3
-C
6
H
4
-CH(CH
3
C
2
HS
362 CU 3 2-t-C 4
H
9
-C
6
H
4 -CH (CH 3
C
2
H
'0050/43960 64 363 CU 3 3-t-C 4
H
9
-C
6
H
4 -CH (CH 3
C
2
H
364 CU 3 4- t-C 4 H9-C 6
U
4 -CH CU 3
C
2
H
365 CU 3 2-CU 3 O-C41 4
-CH(CH
3
C
2 Hc 366 CU 3 3-CH 3
O-C
6 Af 4
-CH(CH
3
C
2
H
367 CU 3 4-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
368 CH 3 2-Cyano-C 6
H
4 -CH CH 3
C
2
HS
369 CH 3 3-Cyano-C 6
H
4 -CH (CH 3
C
2
H
370 CU 3 4-Cyano-C 6
H
4
-CH(CH
3
C
2
H
371 CU 3 2,4-C1 2
-C
6
H
3 -CHI 7H 3
C
2
H
372 CH 3 3,4-C 2
-C
6
H
3
-CH(CH
3
C
2
H
373 CU 3 3, 5-C 2
-C
6
H
3 -CH (CH 3
C
2
H
374 CU 3 2,4-(C 3 2
-C
6
H
3
-CH(CH
3
C
2
H
375 CU 3 2,5-(CI 3 2
-C
6
H
3
-CH(CH
3
C
2
H
376 CU 3
CH
3 00C-CH 2
CZHS
377 CU 3
C
2 HS00C-CH 2
C
2
H
378 CU 3 i-C 3
H
7 00C-CH 2
C
2
HU
379 CH 3 t-C 4 HqOOC-CH 2
C
2
HS
380 CH 3 t-C 4
H
9 00C-CH(CH 3
C
2
HU
381 CU 3
N=-C-CH
2
C
2
H
382 CU 3
C
6
H
5
CO-CH
2
C
2
HS
383 CU 3 Pyrid-2--yl-methyl C 2
H
384 CU 3 Pyrazin-2-yl-methyl C 2
H
385 CU 3 Pyrimidin-2-yl-methyl C 2
H
386 CU 3 Fur-2-yl-methyl C 2
H
387 CU 3 Pyrrol-2-yl-methyl C 2
HS
388 CU 3 N-Methylpyrrol--2-ylmethyl C 2
U
389 CU 3 Thien-2-ylmethyl C 2
H
390 CU 3 Isoxazol-5-ylnethyl C 2
H
391 CH 3 Thiazol-2-ylmethyl C 2
H
392 CH 3 Thiazol-5-ylmethy2. C 2
H
393 CU 3 oxazol-2-ylmethyJ. C 2
U
394 CU 3 Pyrazol-3-ylmethyl C 2
H
395 CU 3 Benzofuran-2-ylmethyl C 2
H
396 CU 3 Indol-2-ylmethyl C 2
H
397 CU 3 Indol-3-ylmethyl C 2
HS
398 CU 3 Benzothiazol-2-ylxnethyl C 2
HS
399 CU 3 Quinolin-2-ylmetllyl C 2
H
400 CU 3 4-UC-C 6 4 OCH (CH 3
-CH
2
C
2
H
0050/43 960 Table
CH
3 Compd. No.
1 2 3 4 6 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34
R
2
H
CH
3 t-C 4
H
9
CH
2
=CH-CH
2
CH
2 =C -CH 2
CH
2 =C (CR 3
-CR
2
CH
3
CH=CH-CH
2
HC---CCH
2
CH
3
C=-C-CH
2 CYClo-C 6
H
1 1
C
6
H_
5
-CH
2 2-F-C 6
H
4
-CH
2 3-F-C 6
H
4
-CH
2 4-F-C 6
H
4
-CH
2 2-Cl-C 6
H
4
-CH
2 3-Cl-C 6 1 4
-CH
2 4-Cl-C 6
H
4
-CH
2 2-Br-C 6
H
4
-CH
2 3-Br-C&H 4
-CH
2 4-Br-C 6 1 4
-CH
2 2-CH 3
-C
6
H
4
-CH
2 3-CH 3
-C
6
H
4
-CH
2 4-CH 3
-C
6
H
4
-CH
2 2-CF 3 -C6H 4
-CH
2 3-CF 3
-C
6
H
4
-CH
2 4-CF 3
-C
6
H
4
-CH
2 2-i-C 3
H
7
-C
6
H,,-CH
2 3-i-C 3
H
7
-C
6
H
4
-CH
2 4-i -C 3
H
7
-C
6
H
4
-CH
2 2-t-C 4 H9-C 6
H
4
-CH
2 3-t-C 4 H9-C 6
H
4
-CH
2 4 -t-C 4
,H
9
-C
6
H
4
-CH
2 2-CH 3
O-C
6
H
4
-CH
2 3-CH 3
O-C
6
H
4
-CH
2 0050/43960 66 H 4-CH 3
O-C
6
H
4
-CH
2 36 H 2-Cyano-C 6
H
4
-CH
2 37 H 3-Cyano-CGH 4
-CH
2 38 H 4-Cyano-C 6
H
4
-CH
2 39 H 2-Nitro-C 6
H
4
-CH
2 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-C1 2
-C
6
H
3
-CH
2 44 H 3, 5-C 2
-C
6 H-4-CH 2 H 2, 6-01 2
-C
6
H
3 -Ci 2 46 H 2, 4- (CH 3 2
-C
6 3
-CH
2 47 Hl 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- (C1 3 2
-C
6
H
3
-CH
2 H 1-Naphthyl-CH 2 51 H 2-Naphthyl-CH 2 52 H C 6
H
5
-CH(CH
3 53 H 2-C1--C 6
H
4
-CH(CH
3 54 H 3-Cl-C 6
H
4
-CH(CH
3 H 4-Cl-C(ri 4
-CH(CH
3 56 H 2-CH 3 6
H
4
-CH(CH
3 57 H 3-CH 3 2 6
H
4 -CH (CR 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 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-t-C 4 Hq-C 6
H
4
-CH(CH
3 63 H 3-t-C 4
H
9
-C
6
H
4
-CH(CH
3 64 H 4-t-C 4 H9-C6H 4 -CH (CH 3 H 2-CH 3
O-C
6
H
4
-CH(CH
3 66 H 3-CH 3 O-Cf 6
H
4 -CH (CH 3 67 H 4-CH 3
O-C
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 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 H 2, 5- CH 3 2
-C
6
H
3 -CH CH 3 76 H CH 3 00C-CH 2 77 H C 2 HS00C-CH 2 78 H i-C 3
H
7 000 -CH 2 '79 H t-C 4
H
9 00C-CH 2 H t-C 4 H9OOC--CH(CH 3 81 H N=-C-CH 2 0050/43960 67 82 H C 6
H
5
CO-CH
2 83 H Pyrid-2-yl-methyl 84 H Pyrazin-2-yl-methyl H Pyrixidin-2-yl-rnethyl 86 H Fur-2-yl-methvJ.
87 H Pyrrol-2-yl-niethyl 88 H N-Methylpyrrol-2-yJlmetliyl 89 H Thien-2-ylmethyl H 91 H Tbiazol-2-ylmethyl 92 H 9 iH oxazol-2-ylnethy.
94 H Pyrazol-3-ylmethyl H Benzofuran-2-ylmethyl 96 H Indol-2-ylmethyl 97 H Indol-3-ylnethyl 98 H Benzothiazol-2-ylmethy.
99 H Quinolin-2-ylmethyl 100 H 4-C1--C 6
H
4
OCH(CH
3
)-CH
2 101 CH 3
H
102 CH3 CH 3 103 CH 3 t-C 4 H9 104 CH 3
CH
2
=CH-CH
2 105 CH 3
CH
2 =C(-Cl)-CH 2 106 CH 3
C(CH
3
)-CH
2 107 CH3 CH3Cfl=CH-CH 2 108 CH 3
HC=-CCH
2 109 CH 3
CH
3
C=-C-CH
2 110 CH 3 cyclo-C 6
H
1 1 111 CH 3
C
6
H
5
-CH
2 112 CH 3 2-F-C 6
H
4
-CH
2 113 CH 3 3-F-C 6
H
4
-CH
2 114 CH 3 4-F-C 6
H
4
-CH
2 115 CH 3 2-C1--CGH 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 6
H
4
-CH
2 119 CH 3 3-Br--C 6
H
4
-CH
2 120 CH 3 4-Br-C 6
H
4
-CH
2 121 CH 3 2- CH 3
-C
6
H
4
-CH
2 122 CH 3 3-CH 3
-C
6
H
4
-CH
2 123 CH 3 4-CH 3
-C
6
H
4
-CH
2 124 CH 3 2-CF 3
-C
6
H
4
-CH
2 125 CM 3 3-CF 3
-C
6
H
4
-CH
2 126 CM 3 4-CF 3
-C
6
H
4
-CH
2 127 CH 3 2-i-C 3
H
7
-C
6
H
4
-CH
2 128 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2 10050/43960 68 129 CTi 3 4-i-C 3 7
-C
6
H
4
-CH
2 130 CH 3 2-t-C 4
H
9
-C
6
H
4
-CH
2 131 CU 3 3-t-C 4
H
9
-CGH
4
-CH
2 132 CU 3 4-t-C 4 9
-C
6 4
-CH
2 133 CU 3 2-CH 3
O-C
6
H
4
-CH
2 134 CE 3 3-CH 3
O-C
6
H
4
-CH
2 135 CE 3 4-CH 3
O-C
6
H
4
-CH
2 136 CH 3 2-Cyano-C 6
H
4
-CH
2 137 CH 3 3-Cyano--C 6
H
4
-CH
2 138 CH 3 4-Cyano-C 6
H
4
-CH
2 139 CH 3 2-Nitro-C 6
H
4
-CH
2 140 CH 3 3-Nitro-C 6 4
-CH
2 141 CH 3 4-NitrO--C 6
H
4
-CH
2 142 CH 3 2,4-Cl 2
-C
6
H
3
-CH
2 143 CE 3 3,4-Cl 2
-C
6
H
3
-CH
2 144 CH 3 3, 5-Cl 2
-C
6
H
3
-CH
2 145 CU 3 2, 6-Cl 2
-C
6
H
3
-CH
2 146 CH 3 2,4-(CH 3 2 -C41 3
-CH
2 147 CH 3 2,f5- (CH 3 2
-C
6
H
3
-CH
2 148 CH 3 3,4-(C 3 2
-C
6
H
3
-CH
2 149 CE 3 3,5-(CH 3 2
-C
6
H
3
-CH
2 150 CH 3 1-Naphthyl-CH 2 151 CH 3 2-Naphthyl-CH 2 152 CE 3
C
6
HS-CH(CH
3 153 CH 3 2-Cl-C 6
H
4
-CH(CH
3 154 CU 3 3-Cl-C 6
H
4
-CH(CH
3 155 CE 3 4-Cl-C 6
H
4
-CH(CH
3 156 CH 3
CH
3
-C
6
H
4
-CH(CH
3 157 CE 3 3-CH 3
-C
6
H
4
-CH(CH
3 158 CH 3 4-CH 3
-C
6
H
4
-CH(CH
3 159 CH 3 2-CF 3
-C
6
H
4
-CH(CH
3 160 CE 3 3-CF 3 -C6H 4 -CH(CH3) 161 CE 3 4-CF 3
-C
6
H
4
-CH(CH
3 162 CE 3 2-tC 4 H9gC 6 4
-CH(CH
3 163 CU 3 3-t-C 4
U
9
-C
6
H
4 -CE (CE 3 164 CU 3 4-t-C 4 Hg-C 6
H
4 -CH (CH 3 165 CU 3 2-CH 3
O-C
6
H
4
-CH(CH
3 166 CE 3 3-CH 3
O-C
6
H
4
-CH(CH
3 167 CE 3 4-CH 3
O-C
6
;H
4
-CH(CH
3 168 CE 3 2-Cyano-C 6
H
4
-CH(CH
3 169 CU 3 3-Cyano-C 6
H
4
-CH(CH
3 170 CE 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 CU 3 3,4-Cl 2 -C(.1 3
-CH(CH
3 173 CE 3 3,5-Cl 2
-C
6
H
3
-CH(CH
3 174 CU 3 2,4-(CH 3 2 -C6H 3
-CH(CH
3 175 CH 3 2.5-(CH 3 2
-C
6
H
3
-C(CH
3 2 10050/43960 69 176 CE 3
CH
3 00C-CH 2 177 CE 2 C2H 5 00C-CH 2 178 CE 3 i-C 3
H
7 00r7-CH 2 179 CH 3 t-C 4 Hq00C-CHi 2 180 CH 3 t-C 4
H
9 00C-CH(CH 3 181 CH 3
N=-C-CH
2 182 CE 3
C
6
H
5
CO-CH
2 183 CE 3 Pyrid-2-yl-methyl 184 CE 3 Pyrazin-2-yl-xnethyl 185 CE 3 Pyrimidin-2-yl-me-thyl 186 CH 3 Fur-2--yl-methyl.
187 CH 3 Pyrrol-2-yl-niethyi.
188 CE 3 N-Methylpyrrol-2-ylmethyl 189 CE 3 Thien-2--ylmethyl 190 CH 3 191 CE 3 Thiazol-2-ylniethyl 192 CE 3 193 CE 3 oxazol-2-ylmethyj.
194 CE 3 Pyrazol-3-ylmethy.
195 CH 3 Benzofuran-2-ylmethyl 196 CE 3 Indol-2-ylmethy.
197 CE 3 Indol-3-ylmethyl 198 CE 3 Benzothiazol-2-ylmethyl 199 CE 3 Quinolin-2-ylinethyl 200 CE 3 4-Cl-C 6
H
4 OCH (CH 3
-CH
2 10050/43960 Table 6
C=N
N=C
R6 I
OCH
3
O=C-NHR
4 Compd. No.
1 2 3 4 6 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34
H
CH
3 t-C 4
H
9
CH
2
=CH-CH
2
CH
2 =C (-Cl )-CH2
CH
2
=C(CH
3
)-CH
2
CH
3
CH=CH-CH
2
HC=-CCH
2
CH
3
C-=C-CH
2 CYClo-C 6
H
1 1
C
5
H
5
-CH
2 2-F-C 6 1 4
-CH
2 3-F-C 6H 4
-CH
2 4-F-C 6
H
4
-CH
2 2-Cl-C 6
H
4
-CH
2 3-Cl-C 6
H
4
-CH
2 4-Cl-C 6
H
4
-CH
2 2-Br-C 6
H
4
-CH
2 3-Br-CH 4
-CH
2 4-Br-C 6
H
4
-CH
2 2-CH 3
-C
6
H
4
-CH
2 3-CH 3
-C
6
H
4
-CH
2 4-CH 3
-C
6
H
4
-CH
2 2-CF 3
-C
6
H
4
-CH
2 3-CF 3
-C
6
H
4
-CH
2 4-CF 3
-C
6
H
4
-CH
2 2-i-C 3
H
7
-C
6
H
4
-CH
2 3-i-C 3
H
7
-C
6
H
4
-CH
2 4-i-C 3
H
7
-C
6
H
4
-CH
2 2-t-C 4 H9-C 6
H
4
-CH
2 3-t-C 4 Hq-C;H 4
-CH
2 4-t-C 4 H9-C 6
H
4
-CH
2 2-CH 3
O-C
6
H
4
-CH
2 3-CH 3
O-C
6
H
4
-CH
2 4-CH 3
O-C
6
H
4
-CH
2 0050/43960 71 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-C 6
H
4
-CH
2 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-C 2
-C
6
H
3
-CH
2 H H 43 H 3 ,4-Cl 2
-C
6
H
3
-CH
2 H H 44 H 3,5-C 2 -0 6
H
3 -qH 2 H H 45 H 2, 6-C 2
-C
6
H
3
-CH
2 H H 46 H 2,4-(CH 3 2
-C
6 H3-CH 2 H H 47 H 2, 5- (CH 3 2
-C
6 H3-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 1-14aphthyl-CH 2 H H 51 H 2-Naphthyl-CH 2 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 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 -C6H 4
-CH(CH
3 H H 59 H 2-CF 3
-C
6
H
4
-CH(CH
3 H H 60 H 3-CF 3
-C
6
H
4
-CH(CH
3 H H 61 H 4-CF 3
-C
6
H
4
-CH(CH
3 H H 62 H 2-t-C 4 H9-C 6
H
4 -CH (CH 3 H H 63 H 3-t-C 4 H9-C 6
H
4 -CH (CH 3 H H 64 H 4-t-C 4
H
9
-C
6
H
4
-CH(CH
3 H H 65 H 2-CH 3
O-C
6
H
4
-CH(CH
3 H H 66 H 3-CH 3
O-C
6
H
4
-CH(CH
3 H H 67 H 4-CH 3
O-C
6
H
4 -CH (CH 3 H H 68 H 2-Cyano-C 6
H
4
-CH(CH
3 H H 69 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-C 2
-C
6
H
3
-CH(CH
3 H H 72 H 3,.4-C 2
-C
6
H
3
-CH(CH
3 H H 73 H 3,5-C 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 00C-CH 2 H H 77 H C 2
H
5 00C-CH 2 H H 78 H i-C 3
H
7 00C-CH 2 H H 79 H t-C 4
H
9 00C-CH 2 H H 80 H t-C 4 H9OOC-CH(CH 3 H H 81 H N-=C-CH 2 H H 82 H C 6
HSCO-CH
2 H H .0050/43960 72 83 H Pyrid-2-yl-methyl H H 84 H Pyrazin-2-yl-methyl H H H Pyrimidin-2-yl-methyl H H 86 H Fur-2--yl-niethyl H H 87 H Pyrrol-2-yl-methyl H H 88 H N-Methylpyrrol-2-ylmethyl H H 89 H Thien-2-ylmethyl H H H Isoxazol-5-ylmethyl H H 91 H Thiazol-2-ylmethyl H H 92 H Thiazol-5-ylmethyl H H 93 H Oxazol-2-ylmethy. H H 94 H Pyrazol-3-ylniethyl H H H Benzofuran-2--ylmethyl H H 96 H Indol-2-ylmethyl H H 97 H Indol-3-ylmethyl H H 98 H Benzothiazol-2-ylmethyJ. H H 99 H Quinolin-2-ylxnethyl H H 100 H 4-Cl-C 6
H
4 OCH (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
9 H H 104 CH 3
CH
2
=CH-CH
2 H H 105 CH 3
CH
2 =C(--Cl)-CH 2 H H 106 CH 3 C (CH3) -CH 2 H H 107 CH 3
CH
3
CH=CH-CH
2 H H 108 CH3 HC- CCH 2 H H 109 CH 3
CH
3
C=-C-CH
2 H H 110 CH 3 CYClo-C 6
H
1 1 H H ill CH 3
C
6
HS-CH
2 H H 112 CH 3 2-F-C 6
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 6 Hi 4
-CH
2 H H 115 CH 3 2-Cl-C 6
H
4
-CH
2 H H 116 CH 3 3-C1-C 6
H
4
-CH
2 H H 117 CH 3 4-C1-C 6
H
4
-CH
2 H H 118 CH3 2-Br-C 6
H
4
-CH
2 H H 119 CH 3 3-Br- 6
H
4
-CH
2 H H 120 CH 3 4-Br-C 6
H
4
-CH
2 H H 121 CH3 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 11253 CH 3 3-CF 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-i-C 3
H
7
-C
6
H
4
-CH
2 H H 128 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2 H H 129 CH 3 4-i-C 3
H
7
-C
6
H
4
-CH
2 H H 10050/43960 73 130 CH 3 2-t-C 4
H
9
-C
6
H
4 -11 2 H H 131 CH 3 3-t-C 4 H9-C 6
H
4
-CH
2 H H 132 CH 3 4-t-C 4
H--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
O-C
6
H
4
-CH
2 H H 135 CH 3 4-CH 3
O-C
6
H
4
-CH
2 H H 136 CH 3 2-Cyano--C 6
H
4
-CH
2 H H 137 CH 3 3-Cyano-C 6
H
4
-CH
2 H H 138 CH 3 4-Cyano-C 6
H
4
-CH
2 H H 139 CH 3 2-Nitro-C 6 1 4
-CH
2 H H 140 CH 3 3-Nitro-C 6
H
4
-CH
2 H H 141 CH 3 4-Nitro-C 6
H
4 -CHi H H 142 CH 3 2, 4-Cl 2
C
6 1' 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
6
H
3
-CH
2 H H 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 H3-CH 2 H H 147 CH 3 2,5-(CH 3 2
-C
6
H
3
-CH
2 H H 148 CH 3 3,4-(CH3) 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 1-Naphthyl-CH 2 H H 151 CH 3 2-Naphthyl-CH 2 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 H 156 CH 3
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-t-C 4 H9-C 6
H
4 -CH (CH 3 H H 163 CH 3 3-t-C 4 H9-CGH 4 -CH (CH 3 H H 164 CH 3 4-t-C 4
H
9
-C
6
B
4 -CH (CH 3 H H 165 CH 3 2-CH 3
O-C
6
H
4
-CH(CH
3 H H 166 CH 3 3-CH 3
O--C
6
H
4
-CH(CH
3 H H 167 CH 3 4-CH 3
O-C
6
H
4
-CH(CH
3 H H 168 CH 3 2-Cyano-C 6
H
4 -,H(CH3) H H 169 CH 3 3-Cyano-C 6
H
4 -CH(CH3) H H 170 CH 3 4-Cyano-C 6
H
4
-CH(CH
3 H H 171 CH 3 2,4-C 2
-C
6
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
6
H
3 -CH (CH 3 H H 174 CH 3 2,4-(CH 3 2
-C
6
H
3
-CH(CH
3 H H 175 CH 3 2,5-(CH 3 2
-C
6
H
3
-CH(CH
3 H H 176 CH 3
CH
3 00C-CH 2 H H 10050/43960 74 177 CH 3
C
2 HS00C-CH 2 H H 178 CHj i-C 3
H
7 00C-CH 2 H H 179 CH 3 t-C 4 H9OOC-CH 2 H H 180 CH 3 t-C 4
H
9 00C-CH(CH 3 H H 181 Cl! 3
N=-C-CH
2 H H 182 Cl! 3
C
6
H
5
CO-CH
2 H H 183 Cl! 3 Pyrid-2-yl-methyj. H H 184 CH 3 Pyrazin-2-yl-methy. H H 185 Cl! 3 Pyrimidin-2-yl-methyl H H 186 CH 3 Fur-2-yl-methyl H H 187 Cl! 3 Pyrrol-2-yl-methyl. H H 188 Cl! 3 N-Methylpyrrol-2-ylmethyl H H 189 Cl! 3 Thien-2-ylmethyl H H 190 CH 3 Isoxazol-5-ylmethyl H H is 191 Cl! 3 Thiazol-2-ylmethyl H H 192 Cl! 3 Thiazol-5--ylmethyl H H 193 Cl! 3 oxazol-2-ylmethyl H H 194 Cl! 3 Pyrazol-3-ylmethyl H H 195 Cl! 3 Benzofuran-2-ylmethyl H H 196 Cl! 3 Indol-2-ylmethy. H H 197 CH 3 Indol-3-ylmethyl H H 198 CH 3 Benzothiazol-2--ylmethyl H H 199 Cl! 3 Quinolin-2-ylmethyl H H 200 Cl! 3 4-Cl-C 6
H
4 OCH(Cl! 3
)-CH
2 H H 201 H H C 2
H
5
H
202 H CH 3
C
2
H
5 j H 203 H t-C 4 l! 9
C
2
H
5
H
204 H Cl! 2
=CH-C!
2
C
2 l! 5
H
205 H CH 2 =C -CH 2
C
2
H
5
H
206 H Cl! 2 =C(Cl! 3 2
C
2 l! 5
H
207 H Cl! 3
CH=CH-CH
2
C
2
H
5
H
208 H HC=-CCH 2
C
2 HS5 H 209 H Cl! 3
C=-C-C!
2
C
2
H
5
H
210 H -,yclo-C 6 Hll C 2
H
5
H
211 H C 6 l! 5
-CH
2
C
2
H
5
H
212 H '-F-C 6
H
4
-CH
2
C
2
H
5
H
213 H 3-F-C 6
H
4
-CH
2
C
2
H
5
H
214 H 4-F-C 6
H
4
-CH
2
C
2 Hs H 215 H 2-C1-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 6
H
4
-C!
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 -Cli 2
C
2 HS H 222 H 3-CH 3
-C
6
H
4
-C!
2
C
2 Hr, H 223 11 4-CH 3
-C
6
H
4
-CH
2
C
2 HS H .0050/43960 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
-CH
2
C
2
H
5
H
227 H 2-i-C 3
H
7
-C
6
H
4
-CH
2
C
2 HS H 228 H 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
H
229 H 4-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
H
230 H 2-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
H
5
H
231 H 3-t-C 4 H9-C 6
H
4
-CH
2
C
2
H
5
H
232 H 4-t-C 4 H9-C 6
H
4
-CH
2
C
2 H5 H 233 H 2-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
H
234 H 3-CH3O-C 6
H
4
-CH
2
C
2
H
5
H
235 H 4-CH 3
O-C
6
;H
4
-CH
2
C
2
H
5
H
236 H ;2-Cyano-C 6
H
4
-CH
2
C
2
H
5
H
237 H 3-Cyano-C 6
H
4
-CH
2
C
2
H
5 q H 238 H 4-Cyano-C6H 4
-CH
2
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 H5 H 241 H 4-Nitro-C 6
H
4
-CH
2
C
2
H.
5
H
242 H 2,4-Cl 2 -C6H 3
-CH
2
C
2
H
5
H
243 H 3,4-C 2
-C
6
H
3
-CH
2
C
2
H
5
H
244 H 3,5-Cl 2
-C
6
H
3
-CH
2
C
2
H
5
H
245 H 2, 6-Cl 2
-C
6
H
3 -C~i 2
C
2
H
5
H
246 H 2, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
H
247 H 2, 5- (C1 3 2
-C
6
H
3
-CH
2
C
2 HS H 248 H 3, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
H
249 H 3,5-(CH 3 2
-C
6
H
3
-CH
2
C
2 HS H 250 H 1-Naphthyl-CH 2
C
2
H
5
H
251 H 2-Naphthyl-CH 2
C
2
H
5
H
252 H C 6
HS-CH(CH
3
C
2
H
5
H
253 H 2-Cl-C6H 4
-CH(CH
3
C
2
H
5
H
254 H 3-Cl-C 6
H
4
-CH(CH
3
C
2 HS H 255 H 4-Cl-C- 6
H
4
-CH(CH
3
C
2
H
5 i H 256 H 2-CH 3
-C
6
H
4
-CH(CH
3
C
2 HS H 257 H 3-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
5
H
258 H 4-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
5
H
259 H 2-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
5
H
260 H 3-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
5
H
261 H 4-CF 3
-C
6
H
4
-CH(CH
3
C
2 HS H 262 H 2-t-C 4
H
9
-C
6
H
4 -CH (CH 3
C
2
H
5
H
263 H 3-t-C 4 H9-C 6
H
4
-CH(CH
3
C
2 HS H 264 H 4-t-C 4 H9-C 6 H4-CH(CH 3
C
2
H
5
H
265 H 2-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
5 q H 266 H 3-CH 3
O--C
6
H
4
-CH(CH
3
C
2
H
5
H
267 H 4-CH 3
O-C
6
H
4
-CH(CH
3
C
2 HS 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
5
H
270 H 4-Cyano--CGH 4
-CH(CH
3
C
2
H
5
H
.0050/43960 76 271 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(Cri 3
C
2 HS 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 HS H 275 H 2115- (CH 3 2
-C
6
H
3 -CH (CH 3
C
2 HS H 276 H CH 3 00C-CH 2
C
2
H
5
H
277 H C 2
H
5 00C-CH 2
C
2
H
5
H
278 H i-C 3
H
7 00C-CH 2
C
2
H
5
H
279 H t-C 4 Hq00C-CH 2
C
2 HS H 280 H t-C 4
H
9 00C-CH(CH 3 CED H 281 H N=-C-CH 2
C
2
H
5
H
282 H C 6
H
5
CO-CH
2
C
2
H
5
H
283 H Pyrid-2-yl-methyJ.
C
2 H5 H 284 H Pyrazin-2-yl-methyl C 2
H
5
H
285 H Pyrimnidin-2-yl-methyj.
C
2
H
5
H
286 H Fur-2-yl-methyJ. C 2
H
5
H
287 H Pyrrol-2-yl-methyl
C
2
H
5
H
288 H N-Methylpyrrol-2-ylmethylC 2
H
5
H
289 H Thien-2-ylmethyl C 2
H
5
H
290 H Isoxazol-5-ylmethyl C 2
H
5 S H 291 H Thiazol-2-ylmethyl C 2 11 5
H
292 H Thiazol-5-ylmethy2. C 2 HS H 293 H oxazol-2-ylmerthyl C 2
H
5
H
294 H Pyrazol-3-ylmethy1 C 2
H
5
H
295 H Benzofuran-2-ylrnethyl
C
2
H
5
H
296 H Indol-2-ylmethyJ. C 2
H
5
H
297 H Indol-3-ylmethyl C 2
H
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-C1--C 6
H
4
OCH(CH
3
)-CH
2
C
2 HS 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 L79 C 2
H
5
H
304 CH 3
CH
2
=CH-CH
2
C
2
H
5
H
305 CH 3
CH
2 =C(-Cl)-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 HS H 308 CH 3
HC=-CCH
2
C
2
H
5
H
309 CH 3
CH
3
CMC-CH
2
C
2
H
5
H
310 CH 3 cyclo-CGH 1 1
C
2 HS H 311 CH 3
C
6
;HS-CH
2
C
2
H
5
H
332 CH 3 2-F-C 6
H
4
-CH
2
C
2
H
5
H
313 CH 3 3-F-C 6
H
4
-CH
2
C
2
H
5
H
314 CH 3 4-F-C 6
H
4
-CH
2
C
2
H.
5
H
315 CH 3 3-Cl-C 6
H
4
-CH
2
C
2
H
5 i 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 HS H .0050/43960 77 3 19 CH 3 3-Br-C 6
H
4
-CH
2
C
2 HS H 320 CH 3 4-Br-C 6
H
4
-CH
2
C
2
H
5 i H 321 CH 3 2-CH 3
-C
6
H
4
-CH
2
C
2
H
5
H
322 CH3 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 HS H 325 CH 3 3-CF 3
-C
6
H
4
-CH
2
C
2
H
5
H
326 CH 3 4-CF 3 -C6H 4
-CH
2
C
2
H
5
H
327 CH3 2-iC 3
H
7 -CfiH4CH 2
C
2
H
5
H
328 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
H
329 CH 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
H
330 CH 3 2-t-C 4 H9-C 6
H
4
-CH
2
C
2
H
5
H
331 CH 3 3-t-C 4 H9--C 6
H
4
-CH
2
C
2
H
5
H
332 CH 3 4-t-C 4 H9-C 6
H
4
-CH
2
C
2
H
5
H
333 CH 3 2-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
H
334 CH 3 3-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
H
335 CH3 4-CH 3
O-C
6
H
4
-CH
2
C
2
H
5 i H 336 CH 3 2-Cyaxio-C 6
H
4
-CH
2
C
2
H
5
H
337 CH 3 3-Cyano-C 6
H
4
-CH
2
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-INitro-C 6
H
4
-CH
2
C
2
H
5
H
340 CH 3 3-Nitro-C 6
H
4
-CH
2
C
2 H5 H 341 CH 3 4-Nitro-C 6
H
4
-CH
2
C
2
H
5
H
342 CH 3 2,4-C.
2
-C
6
H
3
-CH
2
C
2
H
5
H
343 CH 3 3,4-Cl 2
-CGH
3
-CH
2
C
2
H
5
H
344 CH 3 3,5-Cl 2
-C
6
H
3
-CH
2
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
-CH
3
-CH
2
C
2
H
5
H
347 CH 3 2,5-(CH 3 2 -C6H 3
-CH
2
C
2
H
5
H
348 CH 3 3, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2 HS H 349 CH 3 3, 5- (CH 3 2 -C6H 3
-CH
2
C
2
H
5
H
350 CH 3 1-Naphthyl-CH 2
C
2
H
5
H
351 CH 3 2-Naphtliyl-CH 2
C
2
H
5
H
352 CH 3
C
6
H
5
-CH(CH
3
C
2 HS 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
356 CH 3 2-CH 3
-C
6
H
4
-CH(CH
3
C
2 HS 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-t-C 4
H
9
-CGH
4
-CH(CH
3
C
2
H
5
H
363 CH 3 3-t-C 4 Hq-C 6
H
4
-CH(CH
3
C
2
H
5
H
364 CH 3 4-t-C 4
H
9
-C
6
H
4
-CH(CH
3
C
2
H
5
H
365 CH 3 2-CH 3
O--C
6
H
4
-CH(CH
3
C
2
H
5
H
.0050/43960 78 366 OH 3 3-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
5
H
367 CH 3 4--CH 3
O-C
6
H
4 CH (CH 3
CAH
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 HS H 370 OH 3 4-Cyano-C 6
H
4 -CH CRi) C 2 HS H 371 OH 3 2, 4-C 2 6
H
3 -CH (CHi 3
C
2 HS FH 372 CH 3 3, 4-Cl 2
-C
6
H
3 -CH (CH 3
C
2
H
5
H
373 OH 3 3,5-C 2
-C
6
H
3
-CH(CH
3
C
2
H
5
H
374 CH 3 2,4-(CH 3 2 6
H
3
-CH(CH
3
C
2
H.
5
H
375 CH 3 2,5-(CH 3 2 6
H
3
-CH(CH
3
C
2
H
5
H
376 CH 3
CH
3 000-CH 2 C2HS H 377 CH.
3
C
2
H
5 000-CH 2
C
2
H
5
H
378 CH 3 3.-C 3
H
7 00C-CH 2
C
2
H
5
H
379 CH 3 t-C 4 HqOOC-CH 2
C
2
H
5
H
380 CH 3 t-C 4 HqOOC-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
HSCO-CH
2
C
2 HS H 383 CH 3 Pyrid-2-yl-methyl C 2
H
5
H
384 CH 3 Pyrazin-2-yl-methyl C 2
H
5
H
385 CH 3 Pyrimidin-2-yl-methyl C 2
H
5
H
386 CH 3 Fur-2--yl-methyl C 2
H
5
H
387 CH 3 Pyrrol-2-yl-methyl C 2
H
5
H
388 CH 3 N-Methylpyrrol-2-ylmethy. C 2 HS 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 Th,,iazol-2-ylmethyl C 2
H
5
H
392 CH 3 Thiazol-5-ylmethyl C 2
H
5
H
393 OH 3 oxazol-2-ylmethyi C 2
H
5
H
394 C"J Pyrazol-3-ylmethy. C 2
H
5
H
395 CH 3 Benzofuran-2--ylmethyl C 2
H
5
H
396 OH 3 Indol-2-ylinethyl C 2 HS 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 OH 3 4-Cl-CH 4 OCH (CH 3
-CH
2
C
2
H
5
H
401 H H H1 CH 3 402 H OH 3 H CH 3 403 H t-C 4
H
9 H OH 3 404 H CH 2
=CH-CH
2 H CH 3 405 H CH 2 =C(-Cl)-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 OH 3 408 H HC=-CCH 2 H CH 3 409 H CH 3
C=-C-CH
2 H OH 3 410 H CYC10- 6 Hll H CH 3 411 H C 6
H
5
-CH
2 H OH 3 412 H 2-F-C 6
H
4
-CH
2 H OH 3 .0050/43960 79 413 H 3-F-C 6
H
4
-CH
2 H CH 3 414 H 4-F-C 6
H
4
-CH
2 H CH 3 415 H 2-Cl-C 6
H
4
-CH
2 H CH 3 416 H 3-Cl-C 6
H
4
-CH
2 H CH 3 417 H 4-Cl-C 6
H
4
-CH
2 H CH 3 418 H 2-Br-C 6
H
4
-CH
2 H OH 3 419 H 3-Br-C 6
H
4
-CH
2 H OH 3 420 H 4-Br-C 6
H
4
-CH
2 H CH 3 421 H 2-CH 3 -CbH 4 -CF2 H CH 3 422 H 3-CH 3
-C
6
H
4
-CH
2 H OH 3 423 H 4-CH 3
-C
6
H
4
-CH
2 H OH 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 3 426 H 4-CF 3 6
H
4
-CH
2 H CH 3 427 H 2-i-C 3
H
7
-C
6
H
4
-CH
2 H CH 3 428 H 3-i- 3
H
7
-C
6
H
4
-CH
2 H OH 3 429 H 4-i- 3
H
7
-C
6
H
4
-CH
2 H CH 3 430 H 2-t- 4
H
9
-C
6
H
4
-CH
2 H CH 3 431 H 3-t-C 4 H9-C 6
H
4
-CH
2 H CH 3 432 H 4-t-C 4 Hq- 6 Hl 4
-CH
2 H OH 3 433 H 2-CH 3
O-C
6
H
4
-CH
2 H OH 3 434 H 3-CH 3
O-C
6
H
4
-CH
2 H CH 3 435 H 4-CH 3 0-C 6
H
4
-CH
2 H CH 3 436 H 2-CyanO- 6
H
4
-CH
2 H OH 3 437 H 3-Cyano- 6
H
4
-CH
2 H 0113 438 H 4-Cyano-C 6
H
4
-CH
2 H CH 3 439 H 2-Nitro- 6
H
4
-CH
2 H CH 3 440 H 3-Nitro-C 6
H
4
-CH
2 H CH 3 441 H 4-NitrO- 6
H
4
-CH
2 H OH 3 442 H 2,4-C 2
-C
6
H
3 -0H 2 Hi CH 3 443 H 3,4-Cl 2 6
H
3
-CH
2 H CH 3 444 H 3,5-C 2
-C
6
H
3
-CH
2 H OH 3 445 H 2,6-Cl 2
-C
6
H
3
-CH
2 H OH 3 446 H 2,4-(CH 3 2 6
H
3
-CH
2 H OH 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 OH 3 449 H 3,5-(CH 3 2 6
H
3
-CH
2 H OH 3 450 H 1-Naphthyl-CH 2 H CH 3 451 H 2-Naphthyl-CH 2 H CH 3 452 H C 6
HS-CH(CH
3 H CH 3 453 H 2-Cl-0C 6
H
4
-CH(CH
3 H OH 3 454 H 3-Cl-C 6
H
4
-CH(CH
3 H 0113 455 H 4-Cl-C 6
H
4
-CH(CH
3 H OH 3 456 H 2-CH 3
'-C
6
H
4 -CH (CH 3 H OH 3 457 H 3-CH 3
C
6
H
4
-CH(CH
3 H OH 3 458 H 4-CH 3
C
6
H
4 -CH (CH3) H OH 3 459 H 2-CF 3 -0 6
GH
4 -CH(CH3) H OH 3
I
0050/43960 B0 460 H 3-CF 3
-CGH
4
-CH(CH
3 H CH 3 461 H 4-CF 3
-C
6
H
4 -CH (CE 3 H CE 3 462 H 2-t-C 4 H9-C 6
H
4 -CH (CH 3 H CH 3 463 H 3-t-C 4
H
9
-C
6
H
4
-CH(CH
3 H CH 3 464 H 4-t-C 4
H
9
-C
6
H
4 -CH (CH 3 H CE 3 465 H 2-CH 3
O-C
6
H
4 -CH (CH 3 H CH 3 466 H 3-CH 3
O-C
6
H
4
-CH(CH
3 H CE 3 467 H 4-CH 3
O-C
6
H
4
-CH(CH
3 H CE 3 468 H 2-Cyano-C 6
H
4
-CH(CH
3 H CE 3 469 H 3-Cyano-C 6
H
4 H CE 3 470 H 4-Cyano-C 6
H
4
-CH(CH
3 H CE 3 471 H 2,4-Cl 2
-C
6
H
3
-CH(CH
3 H CE 3 472 H 3,4-Cl 2
-C
6
H
3 -CH(CH3) H CE 3 473 H 3,5-Cl 2
-C
6
H
3
-CH(CH
3 H CE 3 474 H 2,4-(CE 3 2
-C
6
H
3
-CH(CH
3 H CE 3 475 H 2,5-(C 3 2
-C
6
H
3
-CH(CH
3 H CE 3 476 H CH 3 00C-CH 2 H CE 3 477 H C 2
H
5 00C-CH 2 H CE 3 478 H i-C3H 7 00C-CH 2 H CE 3 479 H t-C 4 HqOOC-CH 2 H CE 3 480 H t-C 4 H9OOC-CH(CH 3 H CE 3 481 H N-=C-CH 2 H CE 3 482 H C6H 5
CO-CH
2 H CE 3 483 H Pyrid-2-yl-methyl H CE 3 484 H Pyrazin-2-yl-methyl H CE 3 485 H Pyrimidin-2-yl-methy. H CE 3 486 H Fur-2--yl-methyl H1 CE 3 487 H Pyrrol-2-yl-methy. H CE 3 488 H N-Methylpyrrol--2-ylmethyl H CE 3 489 H Thien-2-ylmethy. H CE 3 490 H Isoxazol-5-ylmxethyl H CE 3 491 H Thiazol-2-ylmethyl H CE 3 492 H Thiazo2.-5-ylmethyl H CE 3 493 H oxazol-2-ylmethyl H CE 3 494 H Pyrazo2.-3-ylmethyl H CH 3 495 H Benzofuran-2-yYlmethyl H CE 3 496 H Indol-2-ylmethy- H CE 3 497 H Indol-3-ylmethy- H CE 3 498 H Benzothiazo-2-y'.methyl H CE 3 499 H Quinolin-2-ylma thyl H CE 3 500 H 4-Cl-CGH 4
OCH(CH
3 )-CH2 H CE 3 501 CE 3 H H CE 3 502 CE 3
CE
3 H CE 3 503 CE 3 t-C 4 H9 H CE 3 504 CE 3
CH
2
=CH-CH
2 H CE 3 505 CE 3
CH
2 =C(-Cl)-CH 2 H CE 3 506 CE 3
C(CH
3
)-CH
2 H CE 3 sm 10050/43960 81 507 CH 3
CH
3
CH=CH-CH
2 H CH 3 508 CH 3
HC=-CCH
2 H CH 3 509 CH 3
CH
3 C=C-rCH 2 H CH 3 510 CH 3 c YClo-C 6
H
1 1 H CH 3 511 CH 3
C
6
H
5
-CH
2 H CH 3 512 CH 3 2-F-C 6
H
4
-CH
2 H CH 3 513 CH 3 3-F-C 6
H
4
-CH
2 H CH 3 514 CH 3 4-F-C 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-Cl-C 6
H
4
-CH
2 H CH 3 517 CH 3 4-Cl-C 6
H
4
-CH
2 H CH 3 518 CE 3 2-Br-C 6
H
4
-CH
2 H CE 3 519 CH 3 3-Br-C 6
H
4
-CH
2 H CH 3 520 CE 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 C91 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 CE 3 524 CE 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
-CH
2 H CH 3 527 CE 3 2-i-C 3
H
7
-C
6
H
4
-CH
2 H CE 3 528 CH 3 3-i-C 3
H
7
-C
6
H
4
-CH
2 H CE 3 529 CE 3 4-i-C 3
H
7
-C
6
H
4
-CH
2 H CE 3 530 CE 3 2-t-C 4 H9-C 6
H
4
-CH
2 H CE 3 531 CH 3 3-t-C 4
H
9
-C
6
H
4
-CH
2 H CH 3 532 CH 3 4-t-C 4 H9-C 6
H
4
-CH
2 H CE 3 533 CH 3 2-CH 3
O-C
6
H
4
-CH
2 H CH 3 534 CE 3 3-CH 3
O-C
6
H
4
-CH
2 H CE 3 535 CH3 4-CH 3
O-C
6
H
4
-CH
2 H CE 3 536 CE 3 2-Cyano-C 6
H
4
-CH
2 H CE 3 537 CE 3 3-Cyano- 6
H
4
-CH
2 H CE 3 538 CH 3 4-CyanO--C 6
H
4
-CH
2 H CE 3 539 CE 3 2-NitrO-C 6 4
-CH
2 H CE 3 540 CH 3 3-NitrO-C 6
H
4
-CH
2 H CE 3 541 CE 3 4-Nitro-C 6
H
4
-CH
2 H CE 3 542 CE 3 2,4-C 2
CH
3 CH,! H CH 3 543 CH 3 3,4-C 2
-C
6
H
3
-CH
2 H CE 3 544 CE 3 3, 5-Cl 2
-C
6
H
3
-CH
2 H CH 3 545 CE 3 2, 6-C 2
-C
6 3
-CH
2 H CH 3 546 CE 3 2, 4- (C 3 2
-C
6
H
3
-CH
2 H CH 3 547 CE 3 2, 5-(C 3 2
-C
6
H
3
-CH
2 H CE 3 548 CE 3 3, 4- (CH 3 2 -C6H 3
-CH
2 H CE 3 549 CE 3 3,5-(CH 3 2
-C
6 3
-CH
2 H CE 3 550 CE 3 1-Naphthyl-CH 2 H CH 3 551 CE 3 2-Naphthyl-CH 2 H CE 3 552 CE 3
C
6
HS-CH(CH
3 H CE 3 553 CE 3 2-Cl-C 6
H
4
-CH(CH
3 H CE 3 .0050/43960 82 554 CH 3 2-Cl-CGH 4
-CH(CH
3 H CE 3 555 CH 3 4-Cl-C 6
EH
4
-CH(CH
3 H CH 3 556 CH 3
CH
3
-C
6
H
4
-CH(CH
3 H CE 3 557 CH 3 3-CH 3
-C
6
H
4
-CH(CH
3 H CH 3 558 CE 3 4-CH 3
-C
6
H
4
-CH(CH
3 H CE 3 559 CE 3 2-CF 3
-C
6
H
4
-CH(CH
3 H CH 3 560 CE 3 3-CF 3
-C
6
H
4
-CH(CH
3 H CH 3 561. CE 3 4-CF 3
-C
6
H
4
-CH(CH
3 H CE 3 562 CE 3 2-t-C 4
H
9
-C
6
H
4 -CH (CH 3 H CH 3 563 CE 3 3-t-C 4 9
-C
6
H
4 -CH (CH 3 H CE 3 564 CE 3 4-t-C 4
H
9
-C
6
H
4 -CH (dH 3 H CE 3 565 CE 3 2-CH 3
O-C
6
H
4
-CH(CH
3 H CE 3 566 CE 3 3-CH 3
O-C
6
H
4
-CH(CH
3 H CE 3 567 CE 3 4-CE 3
O-C
6
H
4
-CH(CH
3 H CH 3 568 CE 3 2-Cyano-CrE 4 -CH (dH 3 H CE 3 569 CE 3 3-Cyano-C 6
E
4 -CE (CE 3 H CE 3 570 CE 3 4-Cyano)-C 6
H
4 -CH (CH 3 H CE 3 571 CE 3 2,4-C 2
-C
6 3
-CH(CH
3 H CE 3 572 CE 3 3,4-Cl 2
-C
6
H
3
-CH(CH
3 H CE 3 573 CE 3 3, 5-C.
2 -CrH 3 -CH (CH 3 H CE 3 574 CE 3 2, 4- (C 3 2
-C
6
H
3 -CE (CE 3 H CE 3 575 CE 3 2, 5- (C 3 2
-C
6
H
3 -CE (CH 3 H CE 3 576 CE 3
CH
3 00C-CH 2 H CE 3 577 CE 3
C
2 HS00C-CH 2 H CE 3 578 CE 3 i-C 3
H
7 00C-CH 2 H CE 3 579 CE 3 t-C 4 HqOOC-CH 2 H CE 3 580 CE 3 t-C 4
H
9 00C-CH(CH 3 H CE 3 581 CE 3
N=-C-CH
2 H CE 3 582 CE 3
C
6
E
5
CO-CH
2 H CE 3 583 CE 3 Pyrid-2-yl-methyl H CE 3 584 CE 3 Pyrazin-2-yl-methyl H CE 3 585 CE 3 Pyrimidin-2-yl-iethy2. H CE 3 586 CE 3 Fur-2-yl-methyl H CE 3 587 CE 3 Pyrrol-2-yl-methyl H CE 3 588 CH 3 N-Methylpyrrol-2-ylmethylH CE 3 589 CE 3 Thien-2-ylinethyl H CH 3 590 CE 3 Isoxazol-5-ylmethyl H CE 3 591 CE 3 Thiazol-2-ylmethyl H CE 3 592 CE 3 Thiazol-5-ylmethyl H CE 3 593 CE 3 oxazol-2-ylmethyl H CE 3 594 CE 3 Pyrazol-3-ylmethy. H CE 3 595 CE 3 Benzofuran-2-yJlnethyl H CE 3 596 CE 3 Zndal-2-ylmethyl H CE 3 597 CE 3 Ind&')-3-ylmethyl H CH 3 598 CE 3 Benzothiazol-2-yluethyl H CE 3 599 CE 3 Quinolin-2-ylmethyl H CE 3 600 CE 3 4-Cl-C 6
H
4
OCH(CH
3
)-CH
2 H CE 3 00050/43960 83 601 H H C 2 HS CH 3 602 H CH 3
C
2
H
5
CH
3 603 H t-C 4 H9 C 2
H
5
CH
3 604 H CH 2
=CH-CH
2
C
2
H
5
CH
3 605 H CH 2 =C(-Cl)-CH 2
C
2
H
5
CH
3 606 H CH 2
=C(CH
3
)-CH
2
C
2
H
5
CH
3 607 H CHCH=CH-CH? C 2
H
5
CH
3 608 H HC=-CCH 2
C
2 HS CH 3 609 H CH 3
C=-C-CH
2
C
2
H
5
CU
3 610 H cyclo-C 6
H
1 1
C
2
H
5
CH
3 611 H C 6
H
5
-CH
2
C
2 H5 CU 3 612 H 2-F-C 6
H
4
-CH
2
C
2
H
5
CH
3 613 H 3-F-C 6
H
4
-CH
2
C
2
H
5
CH
3 614 H 4-F-C 6
H
4
-CH
2
C
2
H
5
CU
3 615 H 2-C1-C 6
H
4
-CH
2
C
2
H
5 CH3 616 H 3-Cl-CGH 4
-CH
2
C
2
H
5
CH
3 617 H 4-C1-C 6
H
4
-CH
2
C
2
H
5
CH
3 618 H 2-Br-C 6
H
4
-CH
2
C
2 HS CH 3 619 H 3-Br-C 6
H
4
-CH
2
C
2
H
5
CU
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
-CH
2
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
CU
3 624 H 2-CF 3
-C
6
H
4
-CH
2
C
2
H
5 s CH 3 625 H 3-CF 3
-C
6
H
4
-CH
2
C
2
H
5
CH
3 626 H 4-CF 3
-C
6
H
4
-CH
2
C
2
H
5
CU
3 627 H 2-i-C 3 H7-C 6
H
4
-CH
2
C
2
H
5
CU
3 628 H 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
CH
3 629 li- 4-i-C 3
H
7
-CH
4
-CH
2
C
2 11 5
CH
3 630 H 2-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
H
5
CU
3 631 H 3-t-C 4
H
9
-C
6
H
4
-CH
2
C
2 H5 CH 3 632 H 4-t-C 4
H
9
-C
6
H
4
-CH
2
C
2
H
5
CU
3 633 H 2-CH 3
O--C
6
H
4
-CH
2
C
2
H
5
CH
3 634 H 3-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
CH
3 635 H 4-CH 3
O-C
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-C 6
H
4
-CH
2
C
2
H
5
CU
3 638 H 4-CyanO-C 6
H
4 -CH2 C 2
H
5
CH
3 639 H 2-Nitro-CH 4
-CH
2
C
2
H
5
CH
3 640 H 3-Nitro-CAH-CH 2
C
2
HU
5
CU
3 641 H 4-Nitro-C 6
H
4
-CH
2
C
2
H
5
CH
3 642 H 2, 4-C 2
-C
6
H
3
-CH
2
C
2
H
5
CU
3 643 H 3 4-Cl 2
-C
6
U
3 -CH2 C 2
H
5
CU
3 644 H 3 5-Cl 2
-C
6
H
3
-CH
2
C
2
H
5
CU
3 645 H 6-Cl 2
-C
6
H
3
-CH
2
C
2
H
5
CU
3 646 H 2,4-(CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
CU
3 647 H 2,5-(CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
CU
3 10050/43960 84 648 H 3,4-(CH 3 2
-C
6 H3-CH 2
C
2
H
5
CH
3 649 H 3,5-(CH 3 2 -C6H 3
-CH
2
C
2
H
5
CH
3 650 H I-Naphthyl-CH 2
C
2
H
5
CH
3 651 H 2-Naphthyl-CH 2
C
2
H
5
CH
3 652 H C 6
H
5
-CH(CH
3
C
2 HS CH 3 653 H 2-Cl-C 6
H
4
-CH(CH
3
C
2
H
5
CH
3 654 H 3-Cl-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
3 656 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
H
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
C
2
H
5
CH
3 661 H 4-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
5
CH
3 662 H 2-t-C 4
H
9
-C
6
H
4
-CH(CH
3
C
2
H
5
CU
3 663 H 3-t-C 4 H9-C 6
H
4
-CH(CH
3
C
2 HS CH 3 664 H 4-t-C 4 Hq-C 6
H
4
-CH(CH
3
C
2
H
5
CH
3 665 H 2-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
5
CH
3 666 H 3-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
5
CH
3 667 H 4-CH 3
O-C
6
H
4
-CH(CH
3
C
2
H
5
CH
3 668 H 2-Cyano-CGH 4 -CH (CH 3
C
2
H
5
CH
3 669 H 3-Cyano-CH 4 -CH(CH3) C 2
H
5 S CU 3 670 H 4-Cyano-C 6
H
4
-CH(CH
3
C
2
H
5
CU
3 671. H 2,4-Cl 2
-C
6
H
3
-CH(CH
3
C
2
H
5
CU
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
CU
3 674 H 2,4-(CH 3 2
-C
6
H
3
-CH(CH
3
C
2 HS CH 3 675 H 2,5-(CH 3 2
-C
6
H
3
-CH(CU
3
C
2
H
5
CU
3 676 H CH 3 00C-CH 2
C
2
FH
5
CH
3 677 H C 2
H
5 00C-CH 2
C
2
H
5
CU
3 678 H i-C 3
H
7 00C-CH 2
C
2
H
5
CH
3 679 H t-C 4 HqOOC-CH 2
C
2 HS CU 3 680 H t-C 4 H9OOC-CU(CH 3
C
2
H
5
CU
3 681 H N=-C-CH 2
C
2
H
5
CH
3 682 H C 6
HSCO-CH
2
C
2
H
5
CH
3 683 H Pyrid-2-yl-methyl
C
2
H
5
CU
3 684 H Pyrazin-2-yl-methy-
C
2
H
5
CH
3 685 H Pyrimidin-2-yl-methyl
C
2 HS CU 3 686 H Fur-2-yl-methyl
C
2
H
5
CH
3 687 H Pyrrol-2-yl-methyl
C
2 HS CH 3 688 H N-MethylpyrroJ--2-y~lmethyl C2H5 CU 3 689 H Thien-2-ylmethy-
C
2 HS CH 3 690 H Isoxazol-5-ylmethy-
C
2
H
5
CH
3 691 H Thiazol-2-ylmethy-
C
2
H
5
CH
3 692 H Thiazo2-5-ylmethyl
C
2
H
5
CH
3 693 H oxazol-2-ylmethyl
C
2
H
5
CH
3 694 H Pyrazol-3-ylhiethyl
C
2
H
5
CU
3 10050/43960 695 H Benzofuran-2-ylrnethyl C 2 HS CR 3 696 H Indol-2-ylmethyl C 2
H
5
CR
3 697 H Indol-3-ylmethyi. C 2
H
5
CR
3 698 H Benzothiazol-2-ylmethyJ. C 2
H
5
CH
3 699 H Quinolin-2-ylmethyl C 2
H
5
CR
3 700 H 4-Cl-C 6
H
4
OCH(CH
3
)-CH
2
C
2
H
5
CR
3 701 CH 3 H C 2
H
5
CH
3 702 CH 3
CH
3
C
2
H
5
CH
3 703 CH 3 t-C 4 H9 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(-Cl)-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 CR 3
CH
3
CH=CH-CH
2
C
2
H
5
CH
3 708 CH 3
HC=-CCH
2
C
2
H
5
CR
3 709 CR 3
CH
3
C=-C-CH
2
C
2
H
5
CH
3 710 CH 3 cyclo-C 6
H
1 1
C
2
H
5
CH
3 711 CH 3
C
6
H
5
-CH
2
C
2
H
5
CH
3 712 CR 3 2-F-C 6
H
4
-CH
2
C
2
H
5
CR
3 713 CR 3 3-F-C 6
H
4
-CH
2
C
2
H
5
CR
3 714 CR 3 4-F-C 6
H
4
-CH
2
C
2 HS CH 3 715 CR 3 2-Cl-C 6
H
4
-CH
2
C
2
H
5
CH
3 716 CH 3 3-Cl-C 6
H
4
-CH
2
C
2
H
5
M
717 CH 3 4-Cl-C 6
H
4
-CH
2
C
2
H
5
CR
3 718 CH 3 2-Br-C 6
H
4
-CH
2
C
2 HS CR 3 719 CR 3 3-Br-C 6
H
4
-CH
2
C
2
H
5
CR
3 720 CR 3 4-Br-C 6
H
4
-CH
2
C
2
H
5
CR
3 721 CR 3 2-CH 3
-C
6
H
4
-CH
2
C
2
H
5
CR
3 722 CR 3 3-CH 3
-C
6
H
4
-CH
2
C
2
H
5
CR
3 723 CR 3 4-CH 3
-C
6
H
4
-CH
2
C
2 HS CR 3 724 CR 3 2-CF 3
-C
6
H
4
-CH
2
C
2 HS CR 3 725 CR 3 3-CF 3
-C
6
H
4
-CH
2
C
2
R
5
CR
3 726 CR 3 4-CF 3
-C
6
H
4
-CR
2
C
2
H
5
CR
3 727 CR 3 2-i-C 3 H7-C 6
H
4
-CH
2
C
2
H
5
CR
3 728 CR 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
CR
3 729 CR 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
C
2
H
5
CR
3 730 CR 3 2-t-C 4
H
9
-C
6
H
4
-CH
2
C
2 HS CR 3 731 CR 3 3-t-C 4 H9-C 6
H
4
-CH
2
C
2
HR
5
CR
3 732 CR 3 4-t-C 4
H
9
-C
6
H
4
-CH
2
C
2 HS Vl 733 CR 3 2-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
CR
3 734 CR 3 3-CH 3
O-C
6
H
4
-CH
2
C
2
H
5
CR
3 735 CR 3 4-CH 3
O-C
6
H
4
-CH
2
C
2 HS CR 3 736 CR 3 2-Cyano-C 6
H
4
-CH
2
C
2
H
5
CR
3 737 CR 3 3-Cyano-C 6
H
4 -CH2 C 2
H
5
CR
3 738 CR 3 4-Cyano-C 6
H
4
-CH
2
C
2
H
5
CR
3 739 CR 3 2-Nitro-C 6 4
-CH
2
C
2
H
5
CR
3 740 CR 3 3-Nitro-C 6
H
4 -CH2 C 2
H
5
CR
3 741 CR 3 4-Nitro-C 6
H
4
-CH
2
C
2
H
5
CR
3
I
10050/43960 86 742 CH 3 2, 4-C 2 -C6 3
-CH
2
C
2
H
5
CH
3 743 CH 3 3, 4-C 2
-C
6
H
3
-CH
2
C
2 11 5
CR
3 744 CH 3 3, 5-C1 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
CM
3 746 CM 3 2,4-(CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
CM
3 747 CM 3 2, 5- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
C'M
3 748 CH 3 3, 4- (CH 3 2
-C
6
H
3
-CH
2
C
2
H
5
CR
3 749 CH 3 3, 5- (C 3 2
-C
6
H
3
-CH
2
C
2
H
5
CR
3 750 CM 3 1-Naphthyl-CH 2
C
2
H
5
CH
3 751 CR 3 2-Naphthyl-CH 2
C
2 HS CR 3 752 CH 3
C
6
H
5
-CH(CH
3
C
2
H
5
CM
3 753 CM 3 2-Ca-C6H 4
-CH(CH
3
C
2
H
5
CR
3 754 CM 3 3-Cl-C 6
H
4
-CH(CH
3
C
2
H
5
CR
3 755 CM 3 4-Cl-C 6
H
4
-CH(CH
3
C
2
H
5
CM
3 756 CM 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
CM
3 758 CH 3 4-CH 3
-C
6
H
4
-CH(CH
3
C
2
H
5
CM
3 759 CM 3 2-CF 3
-C
6
M
4
-CH(CH
3
C
2 HS CM 3 760 CH 3 3-CF 3
-C
6
H
4
-CH(CH
3
C
2 HS CM 3 761 CM 3 4-CF 3
-C
6
H
4
-CH(CH
3
C
2
H
5
CM
3 762 CM 3 2-t-C 4
H
9
-C
6
H
4 -CH (CH 3
C
2
H
5
CR
3 763 CM 3 3-tC 4 H9gC 6 4
-CH(CM
3
C
2 HS CM 3 764 CM 3 4-t-C 4 9
-C
6 4 -CM CM 3
C
2
H
5
CH
3 765 CR 3 2-CM 3
O-C
6
M
4
-CR(CH
3
C
2
H
5
CR
3 766 CM 3 3-CH 3
O-C
6
H
4
-CH(CH
3
C
2
M
5
CR
3 767 CM 3 4-CH 3
O-CGH
4
-CH(CH
3
CAM
5
CR
3 768 CM 3 2-Cyano-C 6
H
4
-CH(CH
3
C
2 HS CM 3 769 CR 3 3-Cyano-C 6
M
4 -CR (CR 3
CAS
5
CM
3 770 CM 3 4-Cyano-C 6
H
4
-CH(CH
3
C
2
H
5
CM
3 771 CM 3 2,4-C 2
-C
6
H
3
-CH(CH
3
CAS
5
CM
3 772 CH 3 3,4-C 2
-C
6
H
3
-CH(CH
3
C
2 HS CR 3 773 CH 3 3,5-C 2
-C
6
H
3
-CH(CH
3
C
2
H
5
CR
3 774 CM 3 2, 4- (CM 3 2
-C
6
M
3 -CM (C 3
CAS
5
CH
3 775 CM 3 2, 5- (CM 3 2
-C
6
M
3 -CM (CR 3
C
2
R
5
CM
3 776 CR 3
CH
3 00C-CH 2
C
2
H
5
CR
3 777 CR 3
C
2
H
5 00C-CH 2
C
2
H
5
CR
3 778 CM 3 j-C 3
H
7 00C-CH 2
C
2
H
5
CM
3 779 CM 3 t-C 4 Hq00C-CH 2
C
2
H
5
CM
3 780 CM 3 t-C 4 H9OOC-CH(CH 3
C
2
H
5
CH
3 781 CM 3
N=-C-CH
2
CAS
5
CM
3 782 CM 3
C
6
H
5
CO-CH
2
C
2
H
5
CR
3 783 CM 3 Pyrid-2-yl-methyl C 2
H
5
CR
3 784 CM 3 Pyrazin-2-yl-methyl
C
2
H
5
CM
3 785 CR 3 Pyrimidin-2-yl-methyl
C
2
H
5
CM
3 786 CR 3 Fur-2-yl-methyl
C
2
H
5
CR
3 787 CM 3 Pyrrol-2-yl-methy2.
C
2 HS CM 3 788 CH 3 N-Methylpyrrol-2-ylethyl C2H5 CM 3 10050/43960 87 789 CH 3 Thien-2-ylmethyl C 2
H
5
CH
3 790 CH 3 Isoxazol-5-ylmethyl C 2 11 5
CH
3 791. CH 3 Thiazol-2-ylmethyJ. C 2
H
5
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-yJlmethyl C 2
H
5
CH
3 795 CH 3 Ben'iofuran-2-ylanethyl C 2 HS 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 0050/43960 Table 7 R2-,.
R6c
OCH
3 0 C-N(CH 3 2 Compd. No.
1 2 3 4 6 7 8 9 11 12 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34
H
CH
3 t-C 4
H
9
CH
2 =CH-C 2
CH
2 =C(-Cl)-CH 2
CH
2 =C(CH3)-CH 2
CH
3
CH=CH-CH
2
HC=-CH
2
CIH
3
C=-C-CH
2 CYClO-C 6
H
11 CrH 5
-CH
2 2-F-C 6 11 4
-CH
2 3-F-C 6
H
4
-CH
2 4-F-C 6
H
4
-CH
2 2-C1-C 6
H
4
-CH
2 3-Cl-C 6
H
4
-CH
2 4-C1-C 6
H
4
-CH
2 2-Br-CGH 4 -CH2 3-Br-C 6
H
4
-CH
2 4-Br-C 6
H
4
-CH
2 2-CH 3
-C
6
H
4
-CH
2 3-C11 3
-C
6
H
4
-CH
2 4-CH 3
-C
6
H
4
-CH
2 2-CF 3
-C
6
H
4
-CH
2 3-CF 3
-C
6
H
4
-CH
2 4-CF 3
-C
6 1 4 -C1 2 2-i-C 3
H
7
-C
6
H
4
-CH
2 3-i-C 3
H
7
-C
6 4
-CH
2 4-i-C 3
H
7
-C
6
H
4
-CH
2 2-t-C 4 H9-C 6
H
4
-CH
2 3-t-C 4
H
9
-C
6
H
4
-CH
2 4-t-C4 9
-CH
4
-CH
2 2-CH 3
O-C
6
H
4
-CH
2 3-CH 3
O-C
6
H
4
-CH
2 4-CH 3
O-C
6
H
4
-CH
2 10050/43960 89 36 H 2-Cyano-C 6
H
4
-CH
2
H
37 H 3-Cyano-C 6
H
4
-CH
2
H
38 H 4-Cyano-C 6
H
4
-CH
2
H
39 H 2-Nitro-C 6
H
4
-CH
2
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-C 2
-C
6
H
3
-CH
2
H
43 H 3,4-Cll -H 3
-CH
2
H
44 H 3,5-C 2
-C
6
H
3
-CH
2
H
45 H 2,6-C 2
-C
6
H
3
-CH
2
H
46 H 2, 4- (CH 3 2
-C
6
H
3
-CH
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 1-Naphthyl-CH 2
H
52. H 2-Naphthyl-CH 2 't 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
55 H 4-Cl-C 6
H
4
-CH(CH
3
H
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-t-C 4
H
9
-C
6
H
4 -CH (CH 3
H
63 H 3-t-C 4 H9-C 6 H, -CH (CH 3
H
64 H 4-t-C 4 H9-C 6
H
4
-CH(CH
3
H
65 H 2-CH 3
O-C
6
H
4 -CH (CH 3
H
66 H 3-CH 3
O-C
6
H
4
-CH(CH
3
H
67 H 4-CH 3
O-C
6
H
4 -CH(CH3) 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-C6H 4 -CH(CH3) H 71 H 2,4-C 2 -C6H 3
-CH(CH
3
H
72 H 3,4-C 2
-C
6
H
3
-CH(CH
3
H
73 H 3,5-C 2
-C
6
H
3 -CH(CH3) H 74 H 2,4-(CH3) 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 00C-CH 2
H
77 H C 2
H
5 00C-CH 2
H
78 H i-C 3
H
7 00C-CH 2
H
79 H t-C 4
H
9 O0C-CH 2
H
80 H t-C 4
H
9 00C-CH(CH3)
H
81. H N=-C-CH 2
H
82 H C 6
HSCO-CH
2
H
10050/43960 83 84 86 87 88 89 92 93 94 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 ill 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
U
H
H
CU
3
CH
3
CH
3
CU
3
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
CU
3
CH
3
CU
3
CU
3
CH
3
CU
3
CU
3
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
CU
3
CU
3
CH
3
CU
3
CH
3
CH
3 Pyrid-2-yl-methyl U Pyrazin-2-yl-methyl U Pyriniidin-2-yl-niethyl U Fur-2-yl-methyl H Pyrrol-2-yl-methy. U N-Methylpyrrol-2-ylmethyl U Thien-2-ylmethyl U Isoxazol-5--lethyl H Thiazol-2-ylmethyl H Thiazol-5-ylmethyl H Oxazol-2-ylmethyl H Pyrazol-3-ylmethyl U Benzofuran-2-ylmethyl H Indol-2-ylmethyl H Indol-3-ylmethyl H Benzothiazol-2-ylmethyl U Quinolin-2-ylmethyl H 4-Cl-C 6
H
4 OCU (CU 3
)-CU
2
H
H H
CU
3
H
t-C 4 Ug
H
CH
2
=CU-CH
2
H
CH
2 =C(-C1)-CH 2
H
C(CH
3
)-CH
2
U
CH
3
CU=CH-CH
2
H
HC-=CCH
2
H
CH
3
C=-C-CH
2
H
CYC10-C6H 1 1
H
C
6
H
5
-CH
2
H
2-F-C 6
H
4
-CH
2
H
3-F-CSH 4
-CH
2
H
4-F-C 6
H
4
-CH
2
H
2-Cl-C 6
H
4
-CU
2
H
3-Cl-C 6
H
4
-CH
2
H
4-C1-C 6
H
4
-CH
2
H
2-Br-C 6
H
4
-CU
2
H
3-Br-C 6
H
4
-CH
2
H
4-Br-C 6
H
4
-CH
2
H
2-CH 3
-C
6
H
4
-CH
2
H
3--CH 3
-C
6
H
4
-CH
2
H
4-CH 3
-C
6
H
4
-CH
2
U
2-CF 3
-C
6
H
4
-CH
2
H
3-CF 3
-C
6
H
4
-CU
2
H
4-CF 3
-C
6
H
4
-CH
2
H
2-i-C 3
H
7
-C
6
H
4
-CH
2
H
3-i-C 3
H
7
-C
6
H
4
-CU
2
H
4-i-C 3
H
7
-C
6
H
4
-CH
2
H
10050/43960 91 130 CU 3 2-t-C 4
H
9
-C
6
H
4
-CH
2
H
131 CU 3 3-t-C 4
H
9
-C
6
H
4
-CH
2
H
132 CH 3 4-t-C 4 H9-C 6
H
4
-CH
2
H
133 CU 3 2-CH 3
O-C
6
H
4
-CH
2
H
134 CH 3 3-CH 3
O-C
6
H
4
-CH
2
H
135 CU 3 4-CH 3
O-C
6
H
4
-CH
2
H
136 CH 3 2-Cyano-C 6
H
4
-CH
2
H
137 CU 3 3-Cyano-C 6
H
4
-CH
2
H
138 CH 3 4-Cyano-C 6
H
4
-CH
2
H
139 CU 3 2-Nitro-CGH 4
-CH
2
H
140'V CH 3 3-Nitro-C 6 4
-CH
2
H
141 CH 3 4-Nitro-C 6
H
4 -C'i 2
H
142 CH 3 2,4-Cl 2
-C
6
H
3
-CH
2
H
143 CH 3 3,4-Cl 2
-C
6
H
3
-CH
2
H
144 CU 3 3,5-Cl 2
-C
6
H
3
-CH
2
H
145 CU 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 CU 3 2,5-(C 3 2
-C
6
H
3
-CH
2
H
148 CU 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
U
150 CU 3 1-Naphthyl-CH 2
H
151 CU 3 2-Naphthyl-CU 2
H
152 CU 3
C
6
HS-CH(CH
3
H
153 CU 3 2-Cl-C 6
H
4
-CU(CH
3
U
154 CU 3 3-Cl-C 6
H
4
-CH(CH
3
U
155 CU 3 4-Cl-C 6
H
4
-CH(CU
3
H
156 CU 3
CH
3
-C
6
H
4
-CH(CH
3
U
157 CU 3 3-CH 3
-C
6
H
4
-CH(CH
3
U
158 CU 3 4-CH 3
C
6
H
4 -CH (CH 3
H
159 CU 3 2-CF 3
-C
6
H
4
-CH(CH
3
H
160 CU 3 3-CF 3
-C
6
H
4
-CH(CU
3 h1 161 CU 3 4-CF 3
-C
6
H
4
-CH(CH
3
H
162 CU 3 2-t-C 4
H
9
-C
6
U
4 -CH (CH 3
H
163 CU 3 3-t-C 4
H
9
-C
6
U
4
-CH(CH
3
H
164 CU 3 4-t-C 4 H9-C 6
H
4
-CH(CH
3
H
165 CU 3 2-CH 3
O-C
6
H
4
-CH(CU
3
H
166 CU 3 3-CH 3
O-C
6
U
4
-CH(CH
3
H
167 CU 3 4-CH 3
O-C
6
U
4 -CH(CH.3) H 168 CU 3 2-Cyaio--C 6
U
4 -CU (CU 3
H
169 CU 3 3-Cyano-C 6
H
4
-CH(CH
3
H
170 CU 3 4-Cyano-C 6
H
4
-CH(CH
3
H
171 CU 3 2,4-Cl 2
-C
6
H
3
-CH(CH
3
U
172 CU 3 3,4-Cl 2
-C
6
U
3
-CH(CH
3
H
173 CH3 3,5-C 2
-C
6
H
3
-CH(CH
3
H
174 CU 3 2,4-(CH 3 2
-C
6 3
-CHC
3
U
175 CU 3 2, 5- (CU 3 2
-C
6
U
3
-'OUH(CH
3
H
176 CU 3
CH
3 00C-CU 2
U
1 050/43960 92 177 CE 3
C
2
H
5 00C-CH 2
H
178 CH 3 i-C 3
H
7 00C-CH 2
H
179 CE 3 t-C 4 Hq00C-CH 2
H
180 CE 3 t-C 4 H9OOC-CH(CH 3
H
181 CE 3
N=-C-CH
2
H
182 CE 3
C
6
H
5
CO-CH
2
H
183 CE 3 Pyrid-2-yl-methyl H 184 CE 3 Pyrazin-2-yl-methy. H 185 CE 3 Pyrimidin-2-yl-nethy. H 186 CH 3 Fur-2-yl-methyl H 187 CE 3 Pyrrol-2-yl-methy. H 188 CE 3 N-Methylpyrrol-2-ylmethyl H 189 CE 3 Thien-2-ylmethyl H 190 CE 3 Isoxazol-5-ylmethyl H 191 CE 3 Thiazol-2-ylmethyl H 192 CE 3 Thiazol-5-ylmethyl H 193 CE 3 Oxazol-2-ylmethyl H 194 CH 3 Pyrazol-3-ylmethyl H 195 CE 3 BenZOfuran-2-ylxnethyl H 196 CFL 3 Indol-2-ylmethyl H 197 CE 3 Indol-3-ylmethyl H 198 CE 3 Benzothiazol-2-ylmethyl H 199 CE 3 Quinolin-2-ylmethyl H 200 CE 3 4-Cl-C 6
H
4
OCH(CH
3
)-CH
2
H
201 H HCE 3 202 H CE 3
CE
3 203 H t-C 4 H9 CE 3 204 H CH 2
=CH-CH
2
CE
3 205 H CH 2 =C(-Cl)-CH 2
CE
3 206 H CH 2
=C(CH
3
)-CH
2
CE
3 2607 H CE 3
CH=CE-CH
2
CE
3 208 H HC=-CCH 2
CE
3 209 H CH 3
C=-C-CH
2
CE
3 210 F. CYC1o-C 6
H
1 1
CH
3 211 H C 6
H
5
-CH
2
CE
3 212 H 2-F-C 6
H
4
-CH
2
CE
3 213 H 3-F-C 6
H
4
-CH
2
CE
3 214 H 4-F-C 6
H
4
-CH
2
CE
3 215 H 2-Cl-C 6
H
4
-CH
2
CE
3 216 H 3-Cl-C 6
H
4
-CH
2
CE
3 217 H 4-Cl-C 6
H
4
-CH
2
CE
3 218 H 2-Br-C 6
H
4
-CH
2
CE
3 219 H 3-Br-C 6
H
4
-CH
2
CE
3 220 H 4-Br-C 6
H
4
-CH
2
CH
3 221 H 2-CH 3
-C
6
H
4
-CH
2
CE
3 222 H 3-CH 3
-C
6
H
4
-CH
2
CE
3 223 H 4-CH 3
-C
6
H
4
-CH
2
CE
3 10050/43960 93 224 H 2-CF 3
-C
6
H
4
-CH
2 CH3 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-i-C 3
H
7
-C
6
H
4
-CH
2
CH
3 229 H 4-i-C 3
H
7
-CH
4
-CH
2
CH
3 230 H 2-t-C 4
H
9
-C
6
H
4
-CH
2
CH
3 231 H 3-t; C 4
H
9
-CGH,
1
-CH
2
CH
3 232 H 4-t-C 4 H9-C 6 H1 4
-CH
2
CH
3 233 H 2-CH 3
O-C
6
H
4
-CH
2
CU
3 234 H 3-CH 3
O-C
6
H
4
-CH
2
CH
3 235 H 4-CH 3
O-C
6
H
4
-CH
2
CH
3 236 H 2-Cyano-C 6
H
4 -CH2 CH 3 237 H 3-Cyano-C 6
H
4
-CH
2
CU
3 238 H 4-Cyano-C 6
H
4
-CH
2
CH
3 239 H 2-NitrO-C 6
H
4
-CH
2
CU
3 240 H 3-Nitl'o-C 6
H
4
-CH
2
CH
3 241 H 4-Nitro-C 6
H
4
-CH
2
CU
3 242 H 2,4-Cl 2
-C
6
H
3
-CH
2
CH
3 243 H 3,4-Cl 2 -C6H 3
-CH
2
CH
3 244 H 3,5-Cl 2
-C
6
H
3
-CH
2
CH
3 245 Hl 2,6-C.
2
-C
6
H
3
-CH
2
CH
3 246 H 2, 4-(CU 3 2
-C
6
H
3
-CH
2
CH
3 24' H (CH 3 2
-C
6
H
3
-CH
2
CU
3 2,8 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
CU
3 250 H 1-Naphthyl-CH 2
CU
3 251 H 2-Naphthyl-CH 2
CU
3 252 H C 6
H
5 -CH (CH 3
CH
3 253 H 2-C1--C 6
H
4 -f"H(CH 3
CH
3 254 H 3-C1--C 6
H
4
-CH(CH
3
CH
3 255 H 4-Cl-C 6
H
4
-CH(CH
3
CU
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 Hi 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-t-C 4
H
9
-C
6
H
4 -CH (CH 3
CH
3 263 H 3-t-C 4
H
9
-C
6 1 4 CH (CH 3
CU
3 264 H 4-t-C 4
H
9
-C
6
H
4 -CH (CH 3
CH
3 265 H 2-CH 3
O-C
6
H
4
-CH(CH
3
CU
3 266 H 3-CH 3
O-C
6
H
4
-CH(CH
3
CH
3 267 H 4-CH 3
O-C
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
CU
3 270 H 4-CyanO-C 6
H
4 -CH(CH3) CU 3 0050/43960 94 271 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
CU
3 273 H 3,5-C1 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 00C-CH 2
CH
3 277 H C 2 HS00C-CH 2
CH
3 278 H i-C 3
H
7 00C-CH 2
CU
3 279 H t-C 4 H9OOC-CH 2
CU
3 280 H t-C 4 H9OOC-CH(CH 3
CH
3 281 H N=-C-CH 2
CH
3 282 H C 6
HSCO-CH
2
CH
3 283 H Pyrid-2-yl-methyl CH 3 284 H Pyrazin-2-yl-methyl CH 3 285 H Pyrimidiri-2-yl-methyl CU 3 286 H Fur-2-yl-methyl CH 3 287 H Pyrrol-2-yl-methyl CU 3 288 H N-Methylpyrrol-2-ylmethyl CU 3 289 H Thien-2--ylmetriyl CH 3 290 H Isoxazol-5-ylmethyl CU 3 291 H Thiazol-2-ymet'AiyJ CH 3 292 H Thiazol-5-ylmethyl CU 3 293 H oxazol-2-ylmethy. CH 3 294 H Pyrazol-3-ylmethyl CU 3 295 H Benzofuran-2-yi.methyl CH 3 296 H Indol-2-ylmethyl CH 3 297 H Indol-3-ylmethyl CU 3 298 H Benzothiazol-2-ylmethyl CU 3 299 H Quinolin-2-ylmethyl CH 3 300 H 4-Cl-C 6
H
4
OCH(CH
3
-CH
2
CH
3 301 CH 3 H CH 3 302 CH 3
CU
3
CU
3 303 CU 3 t-C 4 H9 CU 3 304 CU 3
CH
2
=CH-CH
2
CU
3 305 CU 3
CH
2 =C(-C1)-CH 2
CH
3 306 CU 3
CH
2
=C(CH
3
)-CH
2
CU
3 307 CU 3
CH
3
CH=CH-CH
2
CU
3 308 CU 3 HC=-sCCH 2
CU
3 309 CU 3
CH
3
C=-C-CH
2
CU
3 310 CU 3 CYClO-C 6
H
1 1
CH
33 311 CU 3
C
6
H
5
-CH
2
CU
3 332 CU 3 2-F-C 6
H
4
-CH
2
CH
3 313 CH 3 3-F-C 6
H
4
-CH
2
CU
3 314 CU 3 4-F-C 6
H
4
-CH
2
CU
3 315 CU 3 2-Cl-C 6
H
4
-CH
2
CU
3 316 CU 3 3-C1--C 6
H
4
-CH
2
CU
3 317 CU 3 4-Cl-C 6
H
4
-CH
2
CU
3 0050/43960) 318 CR 3 2-Br-C 6
H
4
-CH
2
CR
3 319 CR 3 3-Br-C 6
H
4
-CH
2
CH
3 320 CR 3 4-Br-C 6
H
4
-CH
2
CR
3 321 CR 3 2-CRi 3
-C
6 iH 4
-CH
2
CH
3 322 CR 3 3-CH 3
-C
6
H
4
-CH
2
CR
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
3 325 CH 3 3-CF 3
-C
6
H
4 -dH 2
CR
3 326 CH 3 4-CF 3
-C
6
H
4
-CH
2
CH
3 327 CH 3 2-i-C 3
H
7
-C
6
H
4
-CH
2
CEH
3 328 CR 3 3-i-C 3
H
7
-C
6
H
4
-CH
2
CR
3 329 CR 3 4-i-C 3
H
7
-C
6
H
4
-CH
2
CR
3 330 CR 3 2-t-C 4
H
9
-C
6
H
4
-CH
2
CR
3 331 CH 3 3-t-C 4 Hq-C 6
H
4
-CH
2
CR
3 332 CR 3 4-t-C 4 H9-C 6
H
4
-CH
2
CR
3 333 CR 3 2-CH 3
O-C
6
R
4
-CH
2
CR
3 334 CR 3 3-CRi 3
O-C
6
H
4
'H
2
CH
3 335 CR 3 4-CH 3
O-C
6
R
4
-CE
2
CR
3 336 CR 3 2-Cyano-C 6
H
4
-CH
2
CR
3 337 CR 3 3-Cyano-C 6
H
4
-CH
2
CH
3 338 CR 3 4-Cyano--C 6
H
4
-CH
2
CR
3 339 CR 3 2-Nitro-C 6 4
-CH
2
CR
3 340 CR 3 3-NitrO-C 6 4
-CH
2
CR
3 341 CR 3 4-Nitro-C 6 4
-CH
2
CR
3 342 CR 3 2,4-Cl 2
-C
6
H
3
-CH
2
CR
3 343 CR 3 3, 4-Cl 2
-C
6
H
3
-CH
2
CH
3 344 CR 3 3, 5-Cl 2
-C
6
H
3
-CH
2
CH
3 345 CR 3 2, 6-C1 2
-C
6
R
3
-CH
2
CR
3 346 CH.) 2,4-(CH 3 2
-C
6
H
3
-CH
2
CR
3 347 CR 3 2,5-(CH 3 2
-C
6
H
3
-CH
2
CR
3 348 CR 3 3,4-(CH 3 2
-C
6
H
3
-CH
2
CR
3 349 CR 3 3,5-(CH 3 2 -C6H 3
-CH
2
CR
3 350 CR 3 1-Naphtiyl-CH 2
CR
3 351 CR 3 2-Naphthyl-CH 2
CR
3 352 CR 3
C
6
H
5
-CH(CH
3
CR
3 353 CR 3 2-Cl-C 6
H
4
-CH(CH
3
CR
3 354 CR 3 3-Cl-C 6
H
4
-CK(CH
3
CR
3 355 CR 3 4-Cl-C 6
H
4
-CH(CH
3
CR
3 356 CR 3 2-CH 3
-C
6
H
4
-CH(CH
3
CR
3 357 CR 3 3-CH 3
-C
6
H
4
-CH(CH
3
CR
3 358 CR 3 4-CH 3
-C
6
H
4
-CH(CH
3
CR
3 359 CR 3 2-CF 3
-C
6
H
4
-CH(CH
3
CR
3 360 CR 3 3-CF 3
-C
6
H
4
-CH(CH
3
CR
3 361 CH 3 4-CF 3
-C
6
H
4
-CH(CH
3
CR
3 362 CR 3 2-t-C 4 H9-C 6
H
4 -CH (CH 3
CR
3 363 CR 3 3-t-C 4 H9-C 6
H
4 -CH (CH 3
CR
3 364 CR 3 4-t-C 4 Hq-C 6
H
4
-CH(CH
3
CR
3 0050/43960 96 365 CM 3 2-CH 3
O-C
6
H
4
-CH(CH
3
CM
3 366 CH 3 3-CH 3
O-C
6
H
4
-CH(CH
3
CM
3 367 CM 3 4-CH 3 0-C 6
H
4
-CH(CH
3
CH
3 368 CM 3 2-Cyano-C 6
H
4
-CH(CH
3
CH
3 369 CH 3 3-Cyano-C 6
H
4
-CH(CH
3
CM
3 370 CH 3 4-Cyano-C 6
H
4
-CH(CH
3
CM
3 371 CM 3 2,4-Cl 2
-C
6 3
-CH(CH
3
CM
3 372 CH 3 3,4-C 2
-C
6
H
3
-CH(CH
3
CM
3 373 CM 3 3,5-Cl 2 -C6 3
-CH(CH
3
CM
3 374 CM 3 2,4-(C 3 2
-C
6 3
-CH(CH
3
CM
3 375 CH 3 2, 5-(CH 3 2
-C
6
H
3
-CH(CH
3
CM
3 376 CM 3
CH
3 00C-CH 2
CM
3 377 CM 3
C-)H
5
OOC-CH
2
CM
3 378 CM 3 i-C 3
H
7 00C-CH 2
CH
3 379 CM 3 t-C 4 H9OOC-CH 2
CM
3 380 CM 3 t-C 4
H
9 00C-CH(CH,) CM 3 381 CM 3
N=-C-CH
2
CM
3 382 CM 3
C
6
H
5
CO-CH
2
CM
3 383 CM 3 Pyrid-2-yl-methyl CM 3 384 CM 3 Pyrazin-2-yl-methyl CH 3 385 CM 3 Pyrimidin-2-yl-n.ethyi CM 3 386 CM 3 Fur-2-yl-raethyJ. CM 3 387 CM 3 Pyrrol-2-yl-methyl CM 3 388 CM 3 N-Methylpyrrol-2-ylmethyl CM 3 389 CM 3 Thien-2-ylrnethyl CM 3 390 CM 3 Isoxazol-5-ylmethyl CM 3 391 CM 3 Thiazol-2-ylmethyl CM 3 392 CM 3 Thiazol-5-ylmethyl CM 3 393 CM 3 Oxazol-2-ylmethyl CM 3 394 CM 3 Pyrazol-3-ylmethyl CM 3 395 CM 3 Benzofuran-2-ylmethyl CM 3 396 CM 3 Indol-2-ylmethyl CM 3 397 CM 3 Indol-3-ylmethyi CM 3 398 CM 3 Benzothiazol-2-ylmethyl CM 3 399 CM 3 Quinolin-2-ylmethyl CM 3 400 CM 3 4-Cl-C 6
H
4
OCH(CH
3
)-CH
2
CM
3 The novel compounds of the formula I are suitable as fungicides.
The novel compounds, or the compositions containing them, can be used, for example, in the form of directly sprayable solutions, powdere, suspensions, also high percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting compositions, scattering compositions or granules by spraying, atomizing, dusting, scattering or watering. The use forms depend on the intended applications; in any case, they 0050/43960 97 should if possible guarantee the finest dispersion of the active compounds according to the invention.
Normally, the plants are sprayed or dusted with the active compounds or the seeds of the plants are treated with the active compounds.
The formulations are prepared in a known manner, eg. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents when water is used as a diluent. Suitable auxiliaries for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silicic acid, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Suitable surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg.
lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and also of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.
Powder, scattering and dusting compositions can be prepared by mixing or joint grinding of the active substances with a solid carrier.
Granules, eg. coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
Solid carriers are mineral earths such as silica qel, silicic 0050/43960 98 acids, silica gels [sic], silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and vegetable products, such as cereal meal, tree bark, wood and nutshell meal, cellulose powder or other solid carriers.
Examples of such preparations are: I. a solution of 90 parts by weight of the compound No. 2 from Table 1, ie. 1/2, and 10 parts by weight of N-methyl-a-pyrrolidone, which is suitable for use in the form of very fine drops; II. a mixture of 20 parts by weight of the compound No. 36 from Table 1, ie. 1/36, 80 parts by weight of xylene, parts by weight of the addition product of 8 10 mol of ethylene oxide to 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the addition product of mol of ethylene oxide to 1 mol of castor oil; a dispersion is obtained by fine distribution of the solution in water; III. an aqueous dispersion of 20 parts by weight of the compound No. 1/49, 40 parts by weight of cyclohexanone, parts by weight of isobutanol and 20 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil; IV. an aqueous dispersion of 20 parts by weight of the compound No. 1/58, 25 parts by weight of cyclohexanol, parts by weight of a mineral oil fraction of boiling point 210 280°C and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil; V. a mixture, ground in a hammer mill, of 80 parts by weight of the compound No. 1/2, 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic [sic] acid, parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel; a spray liquor is obtained by fine distribution of the mixture in water; 0050/43960 99 VI. an intimate mixture of 3 parts by weight of the compound No. 1/36 and 97 parts by weight of finely divided kaolin; this dusting composition contains 3% by weight of active compound; VII. an intimate mixture of 30 parts by weight of the compound No. 1/49, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation gives the active compound a good adhesion; VIII. a stable aqueous dispersion of 40 parts by weight of the compound No. 1/58, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted; IX. a stable oily dispersion of 20 parts by weight of the compound No. 1/2, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol-polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
The novel compounds are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the Ascomycetes and Basidiomycetes class. In some cases, they are systemically active and can be employed as foliar and soil fungicides.
They are of particular importance for the control of a multiplicity of fungi on various crop plants such as wheat, rye, barley, oats, rice, maize, grass, cotton, soybean, coffee, sugar cane, grapes, fruit and decorative plants and vegetables such as cucumbers, beans and cucurbits, and also on the seeds of these plants.
The compounds are applied by treating the fungi or the seeds, plants, materials or the soil to be protected from fungal attack with a fungicidally active amount of the active compounds.
Application is carried out before or after infection of the materials, plants or seeds by the fungi.
0050/43960 100 The novel compounds are especially suitable for the control of the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and grass, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries and vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.
The novel compounds can also be employed in the protection of materials (preservation of wood), eg. against Paecilomyces variotii.
The fungicidal compositions in general contain from 0.1 to preferably from 0.5 to 90, by weight of active compound.
Depending on the effect desired, the application rates are from 0.02 to 3 kg of active compound per ha.
In the treatment of seed, in general amounts of active compound from 0.001 to 50 g, preferably 0.01 to 10 g, per kilogram of seed are required.
The compositions according to the invention can also be present as fungicides in the application form together with other active compounds, the [sic] eg. with herbicides, insecticides, growth regulators, fungicides or alternatively with fertilizers.
On mixing with fungicides, in many cases an increase in the spectrum of fungicidal action is obtained here.
0050/43960 101 The following list of fungicides with which the compounds according to the invention can be used jointly are to illustrate the combination possibilities, but not to restrict them: sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc N,N-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zinc (N,N'-propylenebisdithiocarbamate), N, N'-polypropylenebis (thiocarbamoyl) disulfide; nitro derivatives, such as dinitro -methyiheptyl )phenyl crotonate, 2-sec-butyl-4, 6-dinitrophenyl 3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl isopropylcarbonate, diisopropyl heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2, 4-dichloro-6- (o-chloroanilino )-s-triazine, 0, 0-diethyl phthalimidophosphonothioate, (dimethylamino) phosphinyl '-3-phenyl-1, 2, 4-triazole (sic], 2, 3-dicyano-1 ,4-dithioanthraquinone, 2-thio-1 ,3-dithiolo34, 5-b' quinoxaline [sic], methyl 1- (butylcarbamoyl )-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2- (2-f uryl )benzimidazole, 2- (4-thiazolyl )benzimidazole, N- 2-tetrachloroethylthio )tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N' -dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1 3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1, 4-di'chloro-2, 4-(2-chlorophenylhydrazono)--3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide [sic), 8-hydroxyquinoline or its copper salt, 0050/43960 102 2, 3-dihydro-5--carboxanilido-6-methyl-1 ,4-oxathiin, 2,3-dihydro- z:arboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, hydro-4H-pyran-3-c arboxanilide, 2-methylfuran-3-carboxanilide, 2, 5-dixnethyJ liran-3-carboxanilide, 2, 4 5-trime'...v Ls' furan-3-carboxanilide, N-cyclohexyl-2, 5-dimethylfurari-3-carboxamide, N-cyclohexyl-N-methoxy-2, 5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-f ormyl-N-morpholine-2, 2, 2-trichioroethyl acetal, piperazine-1, 4-diylbis 2,2, 2-trichloroethyl)formamide sic], 1- 4-Dichioroanilino) -1-f ormylamino-2, 2, 2-trichioroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N- p-tert-butylphenyl )-2-methylpropyl ]-cis-2, 6dimethylmorpholine, N- (p-tert-butylphenyl )-2-methyipropyl )piperidine, 2-(2,4-dichlorophenyl)-4-ethyl-1 ,3-dioxolan-2-ylethyl]- 1H-1, 2, 4-triazole 1-[E2- 4-dichiorophenyl )-4-n-propyl-1 ,3-dioxolan-2-ylethyl 1- 1H-1, 2, 4-triazole N- (n-propyl 4,6-trichlorophenoxyethyl '-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dirnethyl-1-(1H-1,2,4-triazol-1-yl)- 2-butanone, a- (2-chiorophenyl 4-chiorophenyl 5-butyl-2-dimethylamino-4-hydroxy-6-nethylpyrimidine, bis- (p-chlorophenyl )-3-pyridinemethanol, 1, 2-bis-(3-ethoxycarbonyl-2-thioureido)benzene, 1, 2-bis-83-methoxycarbonyl-2-thioureido)benzene [sic], and also various fungicides, such as dodecylguanidine acetate, 3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl) )glutarimide, hexachlorobenzene, DL-methyl-N- 6-dimethyiphenyl )-N-2-furoyl alaninate, DL-N- 6-dimethyiphenyl -methoxyacetyl )alanine methyl ester, 2, 6-dimethylphenyl )-N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- 6-dimethylphenyl )-N-phenylacetylalanine methyl ester, 5-methyl-5-vinyl-3- 5-dichlorophenyl 4-dioxo-1, 3oxazolidine, 3- 3, 5-dichiorophenyl (-5-methyl-5-methoxymethyl 1-1 ,3-oxazolidine- 2,4-dione [sic], 3-(3,5-dichlorohenyl)-l-isopropylcarbamoylhydantoin [sic], 0050/43960 103 N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-l,2-dicarboximide, 2-cyano-[N-ethylaminocarbonyl-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-a-(1H-l,2,4-triazolylmethyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.
Use Examples Methyl 2-(methoximino-0-[(3-trifluoromethyl)phenylmethyl]phenylglyoxylate 0-methyl oxime and methyl 2-(methoximino- 0-[(3-bromo)phenylmethyl]phenylglyoxylate O-methyl oxime both disclosed in EP 499 823, were used as comparison active compounds.
Use Example 1 Activity against Plasmopara viticola Leaves of potted vines of the variety M5 ller Thurgau were sprayed with aqueous spray liquor which contained 80% active compound and emulsifier in the dry matter. In order to be able to assess the duration of action of the active compounds, the plants were stood in a greenhouse for 8 days after the spray coating had dried on. Only then were the leaves infected with a Zoospore suspension of Plasmopara viticola (vine Peronospora). The vines were then initially stood for 48 hours in a water vapor-saturated chamber at 24°C and subsequently for 5 days in a greenhouse at temperatures from 20 to 30°C. After this time, the plants were stood in the moist chamber for 16 hours once again to accelerate the Sporangia carrier outbreak. The extent of the fungal outbreak on the bottoms of the leaves was then assessed.
In this test, 15% or less of the [lacuna] with a 16 ppmcontaining preparation of the compounds (Table/No.) 1/32, 1/34, 1/49, 1/58, 1/114, 1/128, 1/134, 1/145 and 1/155 showed attack, while up to 70% of the untreated plants were attacked. Up to of the plants treated in this test with 16 ppm-containing preparations of the known active compounds A and B were attacked.
0050/43960 104 Use Example 2 Activity against Pyrenophora teres Barley seedlings of the variety Igri were sprayed in the two-leaf stage until dripping wet with aqueous suspensions which contained active compound and 20% emulsifier in the dry matter. After 24 hours, the plants were inoculated with a spore suspension of the fungus Pyrenophora teres and placed at 18°C for 48 hours in a climatic chamber having a high atmospheric humidity. The plants were then cultivated for a further 5 days in a greenhouse at from to 22°C and 70% relative atmospheric humidity. The extents of the leaf attack was then determined.
The result shows that the active compounds from Table 1, No. 49 and No. 58, when used as a spray liquor containing 63 ppm or 16 ppm of active compound, show a better fungicidal action (5 or attack of the leaves) than the known comparison active compounds A and B (50% attack of the leaves).
Use Example 3 Activity against Fusarium culmorum on wheat Primary leaves of pot-grown wheat of the variety Kanzler were sprayed until dripping wet with aqueous spray liquor which contained 80% active compound and 20% emulsifier in the dry matter.
On the following day, they were inoculated with a spore suspension of Fusarium culmorum and then cultivated at 22-24°C in a climatic chamber having a high atmospheric humidity After 6 days, the extent of symptom development was assessed visually.
In this test, 15% or less of the [lacuna] with a 500 ppmcontaining preparation of the compounds (Table/No.) 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 showed attack, while up to 80% of the untreated plants were attacked. Up to 80% or 60% respectively of the plants treated in this test with 500 ppm-containing preparations of the known active compounds A and B were attacked.
Claims (9)
1. A compound of the formula I where the substituents have the following meanings: Y is oxygen or the group NR 6 Z 1 and Z 2 are independently of one another hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, cyano or nitro; is hydrogen, alkyl, haloalkyl or aryl; is hydrogen, or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heteroarylalkyl, heterocyclyl, cycloalkenyl, arylalkyl, aryl, heteroaryl, arylalkenyl, heteroarylalkenyl, aryloxyalkyl, heteroaryloxyalkyl, acyl, arylcarbonyl, heteroarylcarbonyl or alkoxycarbonyl; R 3 R 4 R 5 and R 6 are independently of one another hydrogen or alkyl; or R 6 and R 2 together with the nitrogen whose substituents they are, can be a ring.
2. A fungicide, containing an inert carrier and a fungicidally active amount of a compound of the formula I as claimed in claim 1. 0050/43960
3.o 3. A process for the contr, o- fungi, which comprises treating the fungi or the material -ants, seeds or the soil threa- tened by fungal attack with a fungicidally active amount of a compound of the formula I as claimed in claim 1.
4. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting an ester of the formula II (where R7=alkyl) R 2 /N Y" with an amine of the formula III R4 (III) or ammonia. A process for preparing compounds of the formula I as claimed in claim 1, in which R 5 is hydrogen, which comprises reacting a mixture of the cyclic hemiaminal VI and the carbonyl com- pound VII HO- R4-N R3 R 4 N-H (VI) (VII) with a hydroxylamine or hydrazine derivative VIII NR 6 I 0050/43960 107 R 2 Y-NH 2 (VIII) or one of its acid addition salts.
6. A compound of the formula VI as in claim 5 [sic].
7. A process for preparing a compound of the formula VI as in claim 5, which comprises reacting an ester of the formula IV (R 7 =alkyl) (IV) with a primary amine of the formula V H 2 N-R 4 (V)
8. A process for preparing a compound of the formula VI as in claim 5 where R 1 H, which comprises converting a monoalkyl a-alkoximinophenylacetamide of the formula X OR N.O'R3 R 4 N. H (where R 3 alkyl) into a metallation product containing two metal radicals and reacting the metallation product with a carhoxylic acid derivative of the general formula XII I -I c~ 108 R 1 C X (X=CI, OCOR7 or OR7 where R7 alkyl or aryl). Q. A process for preparing a compound of the f)rmula VI as in claim which comprises converting a monoalkyl a-alkoximinophenylacetamide of the formula X as in claim 7 [sic] (where R3 alkyl) into a metallation product containing two metal radicals, reac'ing the metallation product with the aldehyde XIII R1 C (XII) and oxidizing the resultant carbinol XIV HO R CH (XIV) R NH R4" A compound of the formula X as in claim 8 [sic], where R3 and R4 are alkyl.
11. A compound of the formula XIV as in claim 9 [sic], where R3 and R4 are alkyl and Ri has the meanings mentioned in claim 1. S 0050/43960 Imino-substituted phenylacetamides, their preparation and fungi- cides containing them Abstract of the disclosure: Compounds of the formula I where Y is oxygen or an NR 6 [sic] group Z 1 and Z 2 are hydrcgan, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkeny- loxy, haloalkyl, haloalkoxy, haloalkenyloxy, cyano or nitro, R 1 is hydrogen, alkyl, haloalkyl or aryl, R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, aryloxyalkyl, heteroaryloxyalkyl, acyl, arylcarbonyl, heteroarylcarbonyl or alkoxycarbonyl, R 3 R 4 R 5 and R 6 are hydrogen or alkyl and R 6 and R 2 can together be a ring, and fungicides containing them are described. INTERNATIONAL SEARCH REPORT international application No. PCT/EP 94/00877 A. CLASSIFICATION OF SUBJECT MATTER Int. C1.5 C07 C 251/48, C 07 C 251/86, C 07 D 217/22, A 01 N 37/50 According to International Patent Classification (IPC) or to both national classification and IPC B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) Int. C1.5 C 07 C 251/00, C 07 D 217/00, A 01 N Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched Electronic data base consulted during the international search (name of data base and, where practicable. search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category" Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. A EP, A2, 0 499 823 (BASF) 1-3, 26 August 1992 (26.08.92), 5-7 claims 1,4-7 (cited in the description) A EP, Al, 0 477 631 (BASF) 1-3,7 01 April 1992 (01.04.92), claims 1,5,8,9 A EP, Al, 0 463 488 (BASF) 1-3,5 02 January 1992 (02.01.92), claims 1,4,6,7 A WO, Al, 92/13 830 1-4 (IMPERIAL CHEMICAL INDUSTRIES) August 1992 (20.08.92), claims 1,8-10 -II Further documents are listed in the continuation of Box C. 7 See patent family annex. Special categories of cited documents: laterdocument publishedafter the inteational filingdateorpriority document defining the general state of the a which is not considered dae and not in conflict with the appliion but cited to understand to be of particular relevance the principle or theory underlying the invention earlier document but published on orafer the international filing date document of particular relevance; the claimed invention cannot be considered novel or cannot be considered to involve an inventive document which may throw doubts on priority claim(s) or which is step when the document is taken alone cited to establish the publication date of another citation or other special reason (as specified) document of particular relevance; the claimed invention cannot be document referring to an oral disclosure, use, exhibition or other considered to involve an inventive step when the document is means combined withoneor more othersuch documents,such combination being obvious to a person skilled in the art P" document published prior to the international filing date but later than the priority date claimed document member of the same patent family Date of the actual completion of the international search Date of mailing of the international search report 1 July 1994 (01.07.94) 22 July 1994 (22.07.94) Name and mailing address of the ISA/ Authorized officer European Patent Office Facsimile No. Telephone No. Form PCT/ISA/210 (second sheet) (July 1992) *INTERNATIONAL SEARCH REPORT intern3tional application No. PCT/EP 94/00877 C (Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. A EP', A2, 0 398 692 1-4 (SHIONOGI SEIYAKU KABUSHIKI KAISHA) 22 November 1990 (22.11.90), claims 1,10,14,15 A EP', Al 0 331 061 (BASF) 1,2 06 September 1989 (06.09.89), abstract Form PcT/ISI210 (continuation of second sheet) (July 1992) IN'1'ENATIONALEIZ RECIIEIRC1WCNjER1I1' lniv''iionaics AkienZCgehen PCT/EP 94/00877 C 07 C 251/48,C 07 C 251/86,c 07 D 217/22,A 01 N 37/50 Nach der Intcrnauonaien V'aten~assirlkation (111K) ocr nach dcr nationaJen Klasstrikation und der 111K Recherchiertcr Mindc-stpru fo (Klassifikationssystemn und Klassifikationssymbolc) C 07 C 251/00,C 07 D 217/00,A 01 N Recherchicrtc aber nicht zumn Mindiestprufswofr geh6cende Vcrer~ntlichungen, soweit diese tinter die recherchierten Gebiete fallen Wihrend der internatsonalen Recherche kordlticrte clektronische Datenbank (Name der Datcnban~k tind evil. ves-wendete Suchbegnffe) C. ALS W1LSENTLICH ANGESEHENE UNTERLAGEN Kategone, Bczeichnung der Ver6 (fend tchung, zoweic erforderlich tinter Angabe der in Betracht koinmenden Teile Betr. Anspruch Nr. A EP, A2, 0 499 823 1-3, (BASF) 5-7 26 August 1992 (26.08.92), Ansprfiche 1, 4-7 (in der Beschreibung zitiert). A EP, Al, 0 477 631 1-3,7 (BAS F) 01 April 1992 (01.04.92), Ansprdche 1,5,8,9. A EP, Al, 0- 463 488 1-3,5 (BAS F) 02 Januar 1992 (02.01.92), Ansprache 1,4,6,7. A WO, Al, 92/13 830 1-4 (IMPERIAL CHEMICAL El ter Ve 1 rd((entlichungen sind der Fortseizunig von Feld C zu [I Siehe Anhang Putali Besondere Kategonien von angegebenien Veratfendichungen Spitere Ver~ffenliekiung, die nach dem interriationalen Anmdecdatumr *A Verdientlichung, die den ailgemeinen Stand der Techeuk definiert, oder dem Priontits'datuim verdffcntlicht worden ist und mit der abet nicht als esonders bedeuteam arizusechen is Antmeldlung richt kollidiert. sondemn nur zum Verstindnis des der Erfindlung zugrundeliegenden Prtnzips oder der ihr zugrundelihegenden lteres Dokcument, das jeedoch erst am oder nzarh dem intemnationalecn Theorie angegeben ist, Arneldedatumn vetotfentlieht worden ist 'X Verdifentlichung von besonderer Becdeutung-, die beanspruchte Erfindung L Verdffenelichung, die gecignet is;, cineni Pnrinttsanspruch zweifelhaft er. karin allein auf~-ud dieser Verdfrendichung nicht als neti oder auf scheinen zu lasscen, oiler durch die das Vero ffend ichungsdatum einer erfindenscher I Aigie berulihend beirachtet werden anderen im Reeherehenbencht lienarneen Veroffeneliehung belege werden VerWferaichung von besonderer Bedeutung; die beantspruchle Erfindung soil oder die aus cincm anderen besonderen Grund angegeben ist (w"c kan nicht ala auf erfinderiseher Titgleest beruhend betrachtet au.sgefuhrt) werdas, warn die Veroffentlichung mit ciner oder mehrereni andcren Verdffendichung, die sich auf etne mUndliche Offenbarung. Verdienihichungen diesct Kategone in Verbindunig gebrache wird tird ecne BEnumung, cine Aumctelung oder anderc Mal~nahmen bezaeht dimse Verbindung ffir cinema Fachnsann nakieiegend ist l'Vetoffenelmchung, die vot dim intemnatiogialen Antmeldedlalum, abet nach .~Verdfflentlichung, die Mitglied derseben Patentfarrulic ist dem beanspruchten Pnionettdaturm verdffenmcht worden ist Datum des Absclumes der intematmonalen Recherche Absendedatum des tritemationalen Recherchenbencbts 01 Juli 1994
22. 17 no Name und Postanschrmft der Internationale Recherchcnbehdrde Bevolitlchtigt Bediensceter Europsches Pateneasne. P.B. 58 18 Patentlin, 2 NL 2280 HV Rijswijk Tel. 31-70) 340.2040, Txc. 31 651 cpo rd REIF e h Fax 31.70) 340-3016 Formblitt PCT ISA. 210 (Biatt 2) IJuli 1992) IN [CRNA'Ii( NA LU~l PCT/EI 94/00877II~~ I 1K Internationales Aktenzatchen PT/P9/087 111,EINSCHLAGIGE VEROFFENTLICHUNGEN (Fartsetzung van Blatt 2) Art 1 Kennzeichnung dler Verotfentlichung. soweit erforderlich unter Angabe der ma~geblichen Teile IBetr. Anspruch Nr. 1 INDUSTRIES) August 1992 (20.08.92), Anspriache 1,8-10. A EP, A2, 0 398 692 1-4 (SHIONOGI SEIYAKU KABUSHIKI KAI SHA) 22 November 1990 (22.11.90), Anspr(iche 1,10,14,15, A EP, Al, 0 331 061 1,2 (BASF) 06 September 1989 (06.09.89), Zusanmerifassuig. 1 Formblatt PCT/ISA/210 (Zusarzbogen) (Januar 1985) zum internationalen Rechercben- bericht liber die internationale Patentanmeldung Nr. o4M ME=- X to the International Search Report to the International Patent Application No. 0b "M E X E: au rapport de recherche inter- national relati4 A la demande de brevet internation& n' PCT/EP 94/00277 SAE 88213 In diesem (Anhana sind die Mitglieder der Patentiamilien der iio obenge- nannten internationalen Recherchenbericht anaef~hrten Patentdokumente anaegeben. Diise Angaben dienen nur zur Uter- richtung und erfolgen ohne Gew~hr. This Aninex lists the patent family members relating t-o the patent documents cited in the above--mentioned inter- national search report. The Office is in no way liable for these particulars which are given merely -for the purpose of information. La pr~sente annexe indique les mesibres de la famille de brevets relatifs aux docueents de brevets citbs dans le rapport de recherche inter- national visde ci-dessus. Les resigne- aents fournis sont donn~s A titre indiCE tif et n'engagent pas la responsibilitt de l'Office. Im Recherchenbericht Datum der Nitglied(er) -der Datum der angef 6hrtes Patentdokument Verbffentlichung Patentfamil ie Ver~f4entlichung Patent docusient cited Publication Patent family Publication in search report date seaber(s) date Document de brevet citt Date de Mebre(s) de la Date de dans le rapport de recherche publication iamille de brevets publication ER P 1 499823 26-08E-92 AtU Al1 11037/974 27-09-92 AU B2 6428 10 8- 9 10-93 CA W 2061407 2 1 8V-92 CS -9 3 92004-37 J. 6-09-92 DE A 1 4 10,)516':' 27-08 92 EFR A3' 4923 1-9; HU AO0 9200537 2B-8 S", H-U At2 60596 28 J. 0-92 I L AO0 100704 (o6-09492 JP At2 6025132 0 1-029 N Z At 24 1658 27-04-94 US At 5254717 19-:10-93 F' A 1 477631 01-04-92 AtU A 1 84656/91 26-0:3-92 AtU B2 637 5,7 77-05-93 CS At3 9102872 15-04-92 DE A 1 407-0038 26-03-92 HU PtO 913023 29-01-92 HU A2 58691 30-03-92 I L AO0 9911J3 15-07-92 JP A2~ 4288045 1.3-1092 NZt A 39853 25-11-93 EF Al1 463:,498 02-01-92 AtU A 1 79296/91 29-01-93 CAt AA 2045725 28 -1 CS A3 9101966 19-02-92 DE A i 4020388 02-01-92' HUJ A 0 5, 12 14 3 :30-1291 HU A 2 58692 7.C-.)19 I L AL) 96626 15-07-92 JR F1 2 4261.147 17-0-9-92 us At 5194662 1603-93 US At 5292759 08-03-94t DE AlI. 4-020384 02-01-92 ZA 9104915 31-0393 WO Al1 9213830 20-08-92 AP AO 9200346 31-01-92 AtU Al1 11619/92 07-09-92 CN At 1065658 28- 10-?2 EF A I 569364. 186 11-93 GB At0 9117530 02-10-91. GB AO0 9200635 IL Pt0 100671 06-09-92 JP T2 6504538 2 6 9 4 PT PA 100072 31 u -9 TR At 25492 1 -1593 US At 5221691. 22.-06-93 GB At 910(-2038 13 ZAi A 9200277 28-10-92 ER F' A 398692 22-1:1-90 AtU Al1 55088/90 2211-90 AL) B2 62897 21-09-9" BR Pk 9002311 06-8- J. CAt AA~ 2017076 1 EF' A 3 3798692 29--05-9 1 us 5.135342 c,1 jR P 2 :24-6268 0 Ii Zt AP 9()0-368e9 27-02-121 E P ;3 10 61 0.-6-o9-89 AT' E 54308 Atu Al. 30866/e9 017-09-89P ALJ B2 608125 211--0 3 -91. DE CO 5890000O4 09-03l-9c EP PI :77 1. 061 0-79 GR T3. 3000973 is-:[1 1-91 IL C' G 9 2573 1 (-09 89 JP A2 2003651 o9-0:1-90 1\Z z 228091 28-08-90) Lis A 49563B7 1 1-09'-90 ZA 8901572 28-41-90
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4310143 | 1993-03-29 | ||
| DE4310143A DE4310143A1 (en) | 1993-03-29 | 1993-03-29 | Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them |
| PCT/EP1994/000877 WO1994022812A1 (en) | 1993-03-29 | 1994-03-19 | Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them |
Publications (2)
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| AU6503494A AU6503494A (en) | 1994-10-24 |
| AU674948B2 true AU674948B2 (en) | 1997-01-16 |
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| AU65034/94A Ceased AU674948B2 (en) | 1993-03-29 | 1994-03-19 | Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0691950B1 (en) |
| JP (1) | JPH08508726A (en) |
| KR (1) | KR960701002A (en) |
| CN (1) | CN1037766C (en) |
| AT (1) | ATE157648T1 (en) |
| AU (1) | AU674948B2 (en) |
| BR (1) | BR9406032A (en) |
| CA (1) | CA2158066A1 (en) |
| CZ (1) | CZ254195A3 (en) |
| DE (2) | DE4310143A1 (en) |
| DK (1) | DK0691950T3 (en) |
| ES (1) | ES2108440T3 (en) |
| GR (1) | GR3025222T3 (en) |
| HU (1) | HUT73145A (en) |
| IL (1) | IL108987A0 (en) |
| NZ (1) | NZ263804A (en) |
| SK (1) | SK119695A3 (en) |
| TW (1) | TW261512B (en) |
| WO (1) | WO1994022812A1 (en) |
| ZA (1) | ZA942163B (en) |
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| JP4114948B2 (en) * | 1994-06-10 | 2008-07-09 | バイエル、クロップ、サイエンス、アクチェンゲゼルシャフト | Process for producing α-methoxyiminocarboxylic acid methylamide and intermediate product thereof |
| JPH08319265A (en) * | 1995-05-23 | 1996-12-03 | Mitsubishi Chem Corp | Production of n-methyl-methoxyiminoacetamide derivative and its intermediate |
| WO1996038408A1 (en) * | 1995-05-31 | 1996-12-05 | Mitsubishi Chemical Corporation | Process for producing n-methyl-methoxyiminoacetamide derivatives and intermediates thereof |
| AR087515A1 (en) * | 2011-08-12 | 2014-03-26 | Basf Se | N-TIO-ANTRANILAMIDE COMPOUNDS AND THEIR USES AS PESTICIDES |
| JP2014522873A (en) * | 2011-08-12 | 2014-09-08 | ビーエーエスエフ ソシエタス・ヨーロピア | Anthranilamido compounds and their use as insecticides |
| CN112661732B (en) * | 2020-12-23 | 2023-08-04 | 湖南化研院检测技术有限公司 | Furanol derivative and preparation method and application thereof |
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| DE3806874A1 (en) * | 1988-03-03 | 1989-09-14 | Basf Ag | SUBSTITUTED HYDRAZONE AND FUNGICIDES CONTAINING THEM |
| US5185342A (en) * | 1989-05-17 | 1993-02-09 | Shionogi Seiyaku Kabushiki Kaisha | Alkoxyiminoacetamide derivatives and their use as fungicides |
| DE59108900D1 (en) * | 1990-06-27 | 1998-01-22 | Basf Ag | O-benzyl oxime ether and crop protection agents containing these compounds |
| DE4030038A1 (en) * | 1990-09-22 | 1992-03-26 | Basf Ag | New 2-substd. phenyl-acetamide derivs. - useful as fungicides, insecticides, acaricides and nematocides |
| EP0569384B2 (en) * | 1991-01-30 | 2000-10-04 | Zeneca Limited | Fungicides |
| DE4105160A1 (en) * | 1991-02-20 | 1992-08-27 | Basf Ag | IMINO-SUBSTITUTED PHENYL DERIVATIVES, THEIR PRODUCTION AND THEIR FUNGICIDES CONTAINING THEM |
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1993
- 1993-03-29 DE DE4310143A patent/DE4310143A1/en not_active Withdrawn
-
1994
- 1994-03-15 IL IL10898794A patent/IL108987A0/en unknown
- 1994-03-16 TW TW083102292A patent/TW261512B/zh active
- 1994-03-19 DE DE59403967T patent/DE59403967D1/en not_active Expired - Lifetime
- 1994-03-19 JP JP6521622A patent/JPH08508726A/en active Pending
- 1994-03-19 WO PCT/EP1994/000877 patent/WO1994022812A1/en not_active Application Discontinuation
- 1994-03-19 BR BR9406032A patent/BR9406032A/en not_active Application Discontinuation
- 1994-03-19 AT AT94912490T patent/ATE157648T1/en not_active IP Right Cessation
- 1994-03-19 CN CN94191640A patent/CN1037766C/en not_active Expired - Fee Related
- 1994-03-19 CZ CZ952541A patent/CZ254195A3/en unknown
- 1994-03-19 CA CA002158066A patent/CA2158066A1/en not_active Abandoned
- 1994-03-19 EP EP94912490A patent/EP0691950B1/en not_active Expired - Lifetime
- 1994-03-19 KR KR1019950704188A patent/KR960701002A/en not_active Application Discontinuation
- 1994-03-19 DK DK94912490.3T patent/DK0691950T3/en active
- 1994-03-19 SK SK1196-95A patent/SK119695A3/en unknown
- 1994-03-19 NZ NZ263804A patent/NZ263804A/en unknown
- 1994-03-19 HU HU9502831A patent/HUT73145A/en unknown
- 1994-03-19 AU AU65034/94A patent/AU674948B2/en not_active Ceased
- 1994-03-19 ES ES94912490T patent/ES2108440T3/en not_active Expired - Lifetime
- 1994-03-28 ZA ZA942163A patent/ZA942163B/en unknown
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1997
- 1997-10-29 GR GR970402859T patent/GR3025222T3/en unknown
Also Published As
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|---|---|
| GR3025222T3 (en) | 1998-02-27 |
| DE59403967D1 (en) | 1997-10-09 |
| WO1994022812A1 (en) | 1994-10-13 |
| CN1120333A (en) | 1996-04-10 |
| ZA942163B (en) | 1995-09-28 |
| NZ263804A (en) | 1996-07-26 |
| BR9406032A (en) | 1996-01-02 |
| DK0691950T3 (en) | 1997-10-06 |
| EP0691950B1 (en) | 1997-09-03 |
| CZ254195A3 (en) | 1996-01-17 |
| EP0691950A1 (en) | 1996-01-17 |
| JPH08508726A (en) | 1996-09-17 |
| ATE157648T1 (en) | 1997-09-15 |
| CN1037766C (en) | 1998-03-18 |
| DE4310143A1 (en) | 1994-10-06 |
| TW261512B (en) | 1995-11-01 |
| IL108987A0 (en) | 1994-06-24 |
| HU9502831D0 (en) | 1995-11-28 |
| KR960701002A (en) | 1996-02-24 |
| SK119695A3 (en) | 1996-02-07 |
| HUT73145A (en) | 1996-06-28 |
| AU6503494A (en) | 1994-10-24 |
| ES2108440T3 (en) | 1997-12-16 |
| CA2158066A1 (en) | 1994-10-13 |
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