AU686304B2 - Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them - Google Patents
Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them Download PDFInfo
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- AU686304B2 AU686304B2 AU14547/95A AU1454795A AU686304B2 AU 686304 B2 AU686304 B2 AU 686304B2 AU 14547/95 A AU14547/95 A AU 14547/95A AU 1454795 A AU1454795 A AU 1454795A AU 686304 B2 AU686304 B2 AU 686304B2
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- alkyl
- amino
- methyl
- alkylamino
- carbonyl
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
0050/4457$ Phenylacetic acid derivatives, preparation thereof and intermediates theref or, and compositions containing them The present invention relates to phenylacetic acid derivatives of the formula I R50N=C(R4)-C(R3)=NOCH<-
(R)
C=NOCH
3
O=C-SRI
where the substituents and the index have the following meanings: RI is hydrogen or Cl-C 4 -alkyl;
R
2 is cyano, nitro, trif luoromethyl, halogen, CI-C 4 -alky2. or
C
1
-C
4 -alkoxy; m is 0, 1 or 2, it being possible for the R 2 radicals to be different if m is 2;
R
3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, Cl-C 4 -alkyl, C-C 4 -haloalkyl, CI-C 4 -alkoxy, Cl-C 4 -haloalkoxy, Cl-C 4 -alkylthio, Cl-C 4 -alkylamino or di-C, -C 4 alkyl amino;
F,
4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, Cl-C 6 -alkyl, Cl-C 6 -alkoxy, CI-C-alkylthio, Cl-C 6 -alkylamino, di-C 1
-C
6 -alkylamino, C 2 -C-alkenyl, C 2
-C
6 -alkenyloxy,
C
2
-C
6 -alkenylthio, C 2 -CG-alkenylamino, N-C 2
-C
6 -alkenyl- N-C, -C 6 -alkyl amino, C 2
-C
6 -alkynyl, C 2
-C
6 -alkynyloxy,
C
2
-C
6 -alkynylthio, C 2
-C
6 -alkynyl amino, N-C 2
-C
6 -alkynyl- N-Cl-C 6 -alkyl amino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aiuninothiocarbonyl, halogen, C 1 -C 6 -alkyl aminocarbonyl, di-Cl-C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothioo arbonyl, di-C 1
-C
6 -alkylaminothiocarbonyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 1
-C
6 -alkoxy, C 1
-C
6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-C I-C 6 -alkyl amino, C 2
-C
6 -alkenyloxy, C 3
-C
6 -cycloalkyl,
C
3
-C
6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-Cl-C 4 -alkoxy, arylthio, aryl-Cl-C 4 -alkylthio, RA /hetaryl, hetaryloxy, hetaryl-Cl-C 4 -alkoxy, hetarylthio,
(~UR
0050//A4575 2 hetaryl-Cl-C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitrc Tdroxyl, mercapto, amino, carboxyl, aminocarbonyi, aminoti~acarbonyl, Cl-CG-alkyl, Cl-C 6 -haloalkyl, CI-C 6 -alkylsulfonyl, Cl-C 6 '-alkylsulfoxyl, C 3
C
6 -cycloalkyl, CI-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, C-C 6 -alkylthio, Cl-C 6 -alkylaxnino, di-C 1
C
6 -alkylamino, Cl-C 6 -alkylaxninocarbonyl, di-Cl-C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2
-C
6 -alkenyl,
C
2
-C
6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(=NOR6)-A,-R 7
C
3
-C
6 -cycloalkyl, C 3
-C
6 -cycloalkoxy, C 3
-C
6 -cycloalkylthio, C 3 -C 6 -cycloalkyl amino, N-C 3
-C
6 -cycloalkyl-N-C 1
-C
6 -alkylamino,
C
3
-C
6 -cycloalkenyl, C 3
-C
6 -cycloalkenyloxy, C 3
-C
6 -cycloalkenylthio, C 3
-C
6 -cycloalkenylami-no, N-C 3
-C
6 -cycloalkenyl-N-C 1
-CG-
alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-Cl-C 6 -alkyl amino, aryl, aryloxy, arylthio, arylainino, N-aryl-N-Cl-C 6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetaxylamino, N-hetaryl- N-Cl-C 6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl, C 1
-C
6 -haloalkyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3
-C
6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, C-C 6 -alkylthio, Cl-C 6 -alkyl amino, di-Cl-C 6 -alkyl amino, C 1
-C
6 -alkyl aminocarbonyl, di-Cl-C 6 -alkylaminocarbonyl, C-C 6 -alkylaminothiocarbonyl, di-C 1
-C
6 -alkylaminothiocarbonyl, C 2
-C
6 -alkenyl,
C
2
-C
6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R
5 is hydrogen, Cl-C 1 0 -alkyl, C 3
-C
6 -cycloalkyl, C 2
-C
1 0 -alkenyl, C 2
-C
1 -alkynyl,
C
1
-C
1 0 -alkylcarbonyl, C 2
-C
1 0 -alkenylc arbonyl, C 3
-C
1 0 -alkynylcarbonyl or Cl-Cl 0 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amifio, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C-C 6 -alkyl, Cl-C 6 -haloalkyl, C-C 6 -alkylsulfonyl, Cl-c 6 -alkylsulfoxyl, Cl-C 6 -alkoxy, CI-C 6 -haloa). 3xy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, CI-C 6 -alkyl amino, di-C, -C 6 -alkyl amino, Cl-C 6 -alkylaminocarbonyl, di-C 1
-C
6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-CI-C 6 -alkylaminothiocarbonyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkenyloxy, eL, A 71 )U ./VT o
I
0050/44575S 3
C
3
-C
6 -cycloalkyl, C 3
-C
6 -CYCloalkoxy, heterocyclyl, he tero-T cyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl,
C
1
-C
6 -haloalkyl, Cl-C 6 -alkylsulfonyl, C 1
-C
6 -alkylsulfoxyl,
C
3
-C
6 -cycloalkyl, Cl-C 6 -alkoxy, CI-C 6 -haloalkoxy,
CI-C
6 -alkoxycarbonyl, Cl-C 6 -alkylthio, C 1 -C 6 -alkyl amino, di-C, -C 6 -alkyl amino, C 1
-C
6 -alkylaminocarbonyl, di-C7 -C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-C C 6 -alkylaminothiocarbonyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, 1hetaryl, hetaryloxy, hetarylthio or C (=NOR 6 7
.F
aryl, arylca.rbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups; cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, CliC 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylcarbonyl, Cl-C 6 -alkylsul fonyl, Cl-C 6 -alkyl sulfoxyl, C 3
-C
6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 al koxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-C, -C 6 -alkyl amino, C 1
-C
6 -alkyl aminocarbonyl, di-C 1
-C
6 -alkylaminocarbonyl, Cl-CG-alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2
-C
6 -alkenyl,
C
2
-C
6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NOR 6 )-An-R 7 where.
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or CI-C 6 -alkyl; n is 0ori1;
R
6 is hydrogen or C 1
-C
6 -alkyl and
R
7 is hydrogen or Cl-C 6 -alkyl, and their salts.
The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.
0050/44575 4 Phenylacetic acid derivatives for pest control are disclosed in the literature (EP-A 432 503, EP-A 463 488).
It is an object of the present invention to provide novel compounds having improved action.
We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use within this context.
The compounds I are obtainable in various ways by processes known per se in the literature.
Fundamentally, it is insignificant in the synthesis of the compounds I whether the group -C(NOCH 3
)-COSR
1 or the group
-CH
2 0N=C(R 3
)-C(R
4
)=NOR
5 is constructed first.
The construction of the group -C(NOCH 3
)-COSR
1 is disclosed, for example, in the literature cited at the outset.
The manner of the synthesis of the -CH20N=C(R 3
)-C(R
4
)=NOR
5 side chain essentially depends on the nature of the substituents R 3 and
R
4 1. In the case in which R 3 and R 4 are not halogen, the construction of the group -CH20N=C(R 3
)-C(R
4
)=NOR
5 in general proceeds by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.
7S -o (NT O 0050/44575
R
5
-ON=C(R
4
)-C(R
3 )=NOH
L
1 -CH2 (R)
C=NOCH
3
III
O=C-SR
I
II
(R
2 )m 4- RS-ON=C(R 4
)-C(R
3 )=NOCH(R2
C=NOCH
3
I
1=C-SRI
L
1 in the formula II is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 370 ff and Houben-Weyl, Vol. 10/1, p. 1189 ff.
The hydroxyimine III required is obtained by reaction of a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
R
5
-L
2
HON=C(R
4
)-C(R
3
)=NOH
VI
IV
R
5
-ON=C(R
4
)-C(R
3
)=NOH
III
L
2 in the formula VI is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; I 0050/44575 6 Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff; Houben-Weyl, Vol. E5, p. 780 ff.
1.1 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyl oxime of the formula V using the dihydroxyimino derivative IV, V then being reacted with the nucleophilically substituted reagent VI to give I.
R
2 )m
HON=C(R
4
)-C(R
3 )=NOH L 1 -CH2 (R2
C=NOCH
3
IV
O=C-SR
1
II
S(R
2 m 20 HON=C(R 4
)-C(R
3 )=NO-CH (R2
C=NOCH
3
V
O=C-SR
I
R
5
-L
2
(R
2
R
5
-ON=C(R
4
)-C(R
3 )=NOCH VI
C=NOCH
3
I
O=C-SR
1 The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. 10/1, p. 1169 ff; Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff; Houben-Weyl, Vol. p. 780 ff.
1.2 In a similar manner, it is also possible to prepare .ne required hydroxyimine of the formula III from a carbonylhydroxyimine VIIa by reaction with a hydroxylamine IXa or its salt IXb.
7 ,v o I 0050/445715
R
5
-ONH
2 IXa 0=C(R 4
)-C(R
3
)=NOH
R5-ONH3 Q I Xb VIla
R-
5
-ON=C(R
4
)-C(R
3
)=NOH
Q' in the formula IXb is the anion of an acid, in particular of an i'iorganic acid, eg. halide such as chloride, The reaction is carried out in iF -manner known per se in~ an inert organic solvent according to the methods described in EP-A 513 580; Houben-Weyl, Vol. 10/4, p. 73 ff; Houben-Weyl, Vol. Rl4b, p. 369 ff and, p. 385 ff.
1.3 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyloxyimine of the formula VIII using the carbonylhydroxyimino derivative VIla, VIII then being reacted with the hydroxylaxnine !Xa or its salt IXb to give I.
O=C(R
4
)-C(R
3 )=NOH Ll-CH 2
C=NOCH
3 II I
O-~C-SR
1 VII a
(R
2
O=C(R
4
)-C(R
3
)=N
VTI
O=C-SR
1 IXa/IXb
R
5 -QN=C
(R
4 -C (R 3 =NOCH2q
R)
C=NOCH
3
O=C-SRI
RA4 0050/44575 8 The reaction is carried out in a manner known per se in an inert organic solvent accor ing to the methods described in Houben-Weyl, Vol. E14b, p. 369 ff; Houben-Weyl, Vol. 10/1, p. 1189 ff and Houben-Weyl, Vol. 10/4, p. 73 ff or EP-A 513 580.
1.4 Another possibility for preparing the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to the benzylhydroxylamine IIa and the further reaction of IIa with a carbonyl compound X.
0
(R
2 )m N-OH L1-CH 2
SC=NOCH
3 O II
O=C-SR
1
(R
2 )m
H
2
NNH
2
C=NOCH
3
O=C-SR
1 /C43(R2)m
H
2
NO-CH
2 7r
C=NOCH
3
O=C-SRI
IIa
R
5
-ON=C(R
4
)-C(R
3 )=O IIa The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488 and German Appl. No. 42 28 867.3.
The carbonyl compound X required is obtained, for example, by reaction of a corresponding hydroxyiminocarbonyl VIIb with a nucleophilically substituted reagent VI
R
5
-L
2
HON=C(R
4
)-C(R
3
R
5
-ON=C(R
4
)-C(R
3 )=0 VIIb rl ~s 0050/44575 9 or by reaction of a corresponding dicarbonyl compound XI with a hydroxyla-mine IXa or its salt IXb
R
5
-ONH
2 IXa
O=C(R
4
)-C(R
3 )=0
E)
RS-ONH
3
Q
IXb RS-ON=C (R 4 -C (R 3 =0 x The reactions are carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55 ff, p. 73 ff, p. 180 ff and p. 217 ff; Houben-Weyl, Vol. E14b, p. 307 ff and 369 ff, Houben-Weyl, Vol. E5, p. 780 ff.
Correspondingly, the compounds I can also be obtained by converting the benzylhydroxylamine Iha first to the corresponding benzyloxyimine of the formula V using the hydroxyimino- VIIb, V then being reacted with the nucleophilically substituted reagent VI to give I as described above.
HON=C(R
4
)-C(R
3 )=o
H
2
NO-CH
2 VIIb Iha 0=C-SR 1
(R
2
HON=C(R
4
)-C(R
3
O=C-SRI
(R
2
R
5
-L
2
VI
R
5 0N=C(R 4
)-C
000/4457$ 1.6 In a similar manner, the compounds I can also be prepared by converting the benzylhydroxylamine IIa first to the benzyloxyimine using the dicarbonyl of the formula XI and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.
(R
2
O=C(R
4
)-C(R
3
H
2
NO-CH
2 2
C=NOCH
3 XI IIa I 0=C-SR 1
(R
2 1 O=C(R 4
)-C(R
3
)=NO-CH
2
C=NOCH
3
VIII
20 =C-SR 1 IXa/IXb R 2 m
RN=C(R
4
)-C(R
3 )=NO-CH 2
C=NOCH
3 I
I
O=C-SR
1 2. Compounds in which R 3 and/or R 4 are a halogen atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf.
Houben-Weyl, Vol. E5, p. 631; J. Org. Chem. 36 (1971), 233; J. Org. Chem. 57 (1992), 3245). Preferably, the corresponding reactions to qive the halogen derivative are performed oAThe.
stages and VIII.
A A 3. Compounds in which R 3 and/or R 4 are bonded to the structure via an O, S or N atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a halogen atom (cf. Houben-Weyl, Vol. E5, p. 826 ff and 1280 ff, J. Org. Chem. 36 (1971), 233, J. Org. Chem. 46 (1981), 3623). Preferably, the corresponding conversions of the halogen derivative are performed in stages I and VIII.
0050/44575 11 4. Compounds in which R 3 and/or R 4 are bonded to the structure via an oxygen atom are in some cases also obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. ES, p. 826-829, Aust. J. Chem. 27 (1974), 1341-9).
Preferably, the corresponding reactions to give the alkoxy derivatives are performed in stages I and VIII.
Compounds in which R 3 is not halogen are preferably obtained by first converting a compound X to the corresponding benzoic acid XIII according to the methods described in EP-A 493 711 using a lactone XII and converting XIII via the corresponding halides to the cyanocarboxylic acids XIV, which are then converted by way of the Pinner reaction (Angew. Chem. 94 (1982), 1) to the a-keto esters XV. The corresponding thioesters, which are subsequently converted to the compounds I, are obtained by "transesterification" of the derivatives XV.
R
5
-,ON=C(R
4
)-C(R
3
)=NOH
(R
2 ii 11\
XII
(R
2 )m
R
5
-ON=C(R
4
)-C(R
3
XIII
(R
2 (Hal=Ha1ogen)
-R
5
-ON=C(R
4
)-C(R
3 XIII.a
(R
2 in
RS-ON=C(R
4
-C(R
3
=NO-CH
2
(R
C=0
XIV
-I i I II Y11 0050/ 44575
R
5
-ON=C(R
4
)-C(R
3
)=NO-CH
2 C O
XVI
C02R
R;H)
(R
2 )m
R
5 -O1=C((R 4
)-C(R
3
XVI
O=C-SR
I
(R
2 )m
R
5
ON=C(R
4
)-C(R
3
)=NOCH
C=NOCH
3
O=C-SR
1 6. In another procedure, the compounds I, for example, are also obtained starting from the compounds XV by first converting the keto group to the oxime ether and then converting the ester function via the carboxylic acid either directly or after activation (formation, for example, of the carbonyl chlorides) to the corresponding thioesters [Organikum, 16th edition (1985), pp. 415, 423 and 622].
a, ss~ I 0050/407S 13 R2
R
5
-ON=C(R
4
)-C(R
3
)=NO-CH
2 (ReH)
C=O
XV
(R
2 m
RS-ON=C(R
4
)-C(R
3
)=NO-CH
2
C=NOCH
3
XV
CO
2
R
R
5
-ON=C(R
4
)-C(R
3
)=NO-CH
2
R
C=NOCH
3 1 CO2H
I
The compounds II can be prepared by the methods described in EP-A 432 503, EP-A 463 488, EP-A 386-561.
On account of their C=C and C=N double bonds, the compounds I can be obtained during preparation as E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, eg. by crystallization or chromatography.
If isomer mixtures are obtained during the synthesis, in general, however, a separation is not absolutely necessary, as the individual isomers can in some cases be converted to one another during preparation for application or during application (eg. under the action of light, acid or base). Corresponding conversions can also take place after application, for example during the treatment of plants, in the treated plant or in the harmful fungus or animal pest to be controlled.
With reference to the C=NOCH 3 double bond, the E isomers of the compounds I are preferred with respect to their activity (configuration based on the -OCH 3 group in relation to the -COSR 1 group).
~L rl--~ OOSO/4457 14 With reference to the -C(R 3
)=NOCH
2 double bond, the cis isomers of the compounds I are preferred with respect to their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups: halogen: fluorine, chlorine, bromine and iodine; alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, eg. 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-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, i,i-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-l-methylpropyl and l-ethyl-2-methylpropyl; alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atc.is as mentioned above; dialkylamino: an amino group which carries two straight-chain or branched alkyl groups which are independent of one another and each have 1 to 6 carbon atoms as mentioned above; alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms, which are bonded to the structure via a carbonyl group alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms, which are bonded to the structure via a sulfonyl group 2 alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via a sulfoxyl group alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group 0050/44575 dialkylaminocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a carbonyl group alkvlaminothiocarbonvyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a thiocarbonyl group dialkylaminothiocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a thiocarbonyl group haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, eg. C 1
-C
2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl; alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom eg. C 1
-C
6 -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-metbylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl- 2-methylpropoxy; alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via an oxycarbonyl group haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, and these groups being bonded to the structure via an oxygen atom; 1 0050/44575 16 alkylthig: straight-chain or branched al~kyl groups having I to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom eg. Cl-C 6 -alkylthio su.ch as methyithic, ethylthio, propylthio, 1-xnethylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, I-ethylpropylthio, hexyithio, 1, 1-dimethylpropylthio, 1, 2-diiethylpropylthio, 1-methylpentyltio 2-methylpentylthio, 3-methyJlpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethlylbutylthio, 1-ethylbutylthio, 2-ethytlbutylthio, 1,1, 2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1-ethyl--1-methylpropylthio and 1-ethyl-2-methylpropylthio; 1s cycloalkyl: monocyclic alkyl. groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; alkenyl:- straight-chain or branched alkeny. groups having 2 to 6 or 10 carbon atoms and a double bond in any desired position, eg. C 2
-C
6 -al)LanyI such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, I-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-1--propenyl, 1-methyl-2--propenyl, 2-methyl- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-penteny., 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyi, 3-methyl-2-butenyl, 1-methyl-3--butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl- 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl--1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1--pentenyl, 4-methyl-1-pentenyl, 1-methyl-2--pentenyl, 2-methyl-2--pentenyl, 3-methyl-2-pente. 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-penteny., 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dirnethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-l-butenyl, 1, 3-dimethyl-2--butenyl, 1, 3-dimethyl-3-butenyl, 2, 2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3, 3-dimethyl-2-butenyl, 2-ethyl-i -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1, 2-trimethyJ.-2-propenyl, 1-ethyl-i-me thyl--2-propenyJ., I-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
W
o00o/44575 17 alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure via an oxygen atom alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to 10 carbon atoms and a double bond in any desired position, which are bonded to the structure via a carbonyl group alkenvlthio or alkenylamino: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure (alkenylthio) via a sulfur atom or (alkenylamino) a nitrogen atom; alkynyl: straight-chain or branched alkynyl groups having 2 to carbon atoms and a triple bond in any desired position, eg.
C
2
-C
6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl- 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl- 4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; alkynyvcarbonyl: straight-chain or branched alkynyl groups having 3 to 10 carbon atoms and a triple bond in any desired position, which are bonded to the structure via a carbonyl group alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any desired position, which are bonded to the structure (alkynyloxy) via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom; cvcloalkox or cvcloalkylthio and cycloalkylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure (cycloalkoxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; cycloalkenyl or cycloalkenyloxy, cyvcloalkenylthio and cycloalkylamino rsicl: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure directly or (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) a sulfur 0050/44570 18 atom or (cycloalkenylamino) via a nitrogen atom, eg. cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl; heterocyclyl or heterocvclvloxy, heterocycivithbio and heterocyclylamino: three- to six-membered, saturated or partly unsaturated mono- or polycyclic haterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamir~o) via a nitrogen atom, such as eg. 2-tetrahydrofuranyl,, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tettahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl (sic], 4-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazcolidinyl, 2-oxazolidinyl, ,4-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2, 4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1,2, 4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3, 4-oxadiazolidin-2-yl, 1,3, 4-thiadiazolidin-2-yl, 1, 3,4-triazolidin-2-yl, 2, 3-dihydrofur-2-yl, 2, 3-dihydrofur-3-yl, 2, 3-dihydrofur-4-yl, 2, 3-dihydrofur-5-yl, 2, 5.dihydrofur-2-yl, 2, 5-dihydrofur-3-yl, 2, 3-dihydrothien-2-yl, 2, 3-dihydrothien- 3-yl, 2, 3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2, 5-dihydrothien-2-yl, 2, 5-dihydrothien-3-yl, 2, 3-dihydropyrrol-2-yl, 2, 3-dihydropyrrol-3-yl, 2, 3-dihydropyrrol-4-yl, 2, 3-dihydropyrrol-5-yl, 2, 5-dihydropyrrol-2-yl, 2, pyrrol-.3-yl, 2, 3-dihydroisoxazol-3-yl, 2, 3-dihydroisoxazol-4-yl, 2, 3-dihydroisoxazol-5-yl, 4, 5-dihydroisoxazol-3-yl, isoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 2, 3-yl, 2, 5-dihydroisothiazol-4-yl, 2, 2, 3-dihydroisopyrazol-3-yl, 2, 3-dihydroisopyrazol-4-yl, 2, 3-dihydroisopyrazol-5-yl, 4, 5-dihydroisopyrazol-3-yl, 4, droisopyrazol-4-yl, 4, 5-dihydroisopyrazol-5-yl, pyrazol-3-yl, 2, 5-dihydroisopyrazol-4-yl, 2, 2, 3-dihydrooxazol-3-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-di- 4, 5-dihydrooxazol-3-yl, 4, 5-dihydrooxazol-4-yl, 4, 5-dihydrooxazol-5-yl, 2, 5-dihydrooxazol-3-yl, 2, oxazol-4-yl, 2, 5-dihydrooxazol-5-yl, 2, 3-dihydrothiazol-2-yl, 2, 3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4 thiazol-2-yl, 4, 5-dihydrothiazol-4-yl, 4, 2, 5-dihydrothiazol-2-yl, 2, 5-dihydrothiazol-4-yl, 2, 2, 3-dihydroimidazol-2-yl, 2, 3-dihydroimidazol-4-yl, 2, 3-dihydroimidazol-5-yl, 4, 5-dihydroimidazol-2-yl, 4, imidazol-4-yl, 4, S-dihydroimidazol-5-yl, 2, 2-yl, 2, 5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 00530/40$7S 19 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tatrahiydropyrimidinyl, pyrimidinyl, 2-tetrahydropyraziny., 1,3, 5-tetrahydrotriazin-2-yl, 1,2, 4-t-etrahydrotriazin-3-yl, 1, 3-dihydrooxazin-2-yl, 1, 3-dithian-2-yl, 2-tetrahydropyranyl. 1, 3-dioxolan-2--yl, 3,4,5,6tetrahydropyridin-2-yl, 4H-1, 3-thiazin-2-yl, 4H-3, 1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1, 3-dihydrooxazin-2-yl, 1,3-dithian-2-yl; aryl or-aryloxy. arvlthio. aryicarbonyi and arvisulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure directly or (aryloxy) via an -,xygen atom or (arylthio) a sulfur atom (arylcarbonyl) via a carbonyl group or (arylsulfony!) via a sulfonyl group (-SO 2 eg.
phenyl, naphthyl and phenanthrenyl or phenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals; arviamino: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure via a nitrogen atom; hetarvi or hetaryloxy. hetarvlthio. hetarvlcarbonyl and hetarvisulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, additionally can contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure directly or (hetaryloxy) via an oxygen atom or (hetarylthio) a sulfur atom (hetarylcarbonyl) via a carbonyl group or (hetarylsulfonyl) via a sulfonyl group eg.
5-membered heteroaryl. containing one to three nitrogen Atoms. 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3, 4-triazol-2-yl; 5-membered heteroarvl. containing one to four nitrogen atoms or-one to-three nitrogen atoms -and a sulfur or oxygen-atom-or an-oxyenoa suu atom: 5-mezubered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, eg.
2-f uryl, 3-f uryl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 0050/44575 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl; benz.o-fused 5-membered heteroarvyl, containing one to three nitrogen atoms or one nitrogen atom and/or an oxygen or sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene- 1,4-diyl group; 5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryL bonded via nitrogen, containing one to three nitrogen atoms: ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the structure via one of the nitrogen ring members; 6-membered heteroaryl, containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazinyl; benzo-fused 6-membered heteroarvyl, containing one to four nitrogen atoms: 6-membered ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene- 1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline, or the corresponding oxy, thio, carbonyl or sulfonyl groups; RA4
-T
0050/44575 21 hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure via a nitrogen atom.
The statement partly or completely halogenated is intended to express that in the groups characterized in this way the hydrogen atoms can be partly or completely replaced by identical or different halogen atoms as mentioned above.
With respect to their biological action, compounds of the formula I are preferred in which m is 0.
Equally preferred are compounds of the formula I in which R 1 is methyl.
In addition, compounds I are preferred in which hydroxyl, cyclopropyl, chlorine, methyl, ethyl, methoxy, methylthio or phenyl.
Compounds I are additionally preferred in which In addition, compounds I are preferred in which Compoun-s I are additionally preferred in which In addition, compounds I are preferred in which In addition, compounds I are preferred in which hydroxyl, cyclopropyl, chlorine, methyl, ethyl, thoxy or methylthio.
Compounds I are additionally preferred in which In addition, compounds I are preferred in which Compounds I are additionally preferred in which In addition, compounds I are preferred in which
R
3 is hydrogen, 1-methylethyl,
R
3 is methyl.
R
3 is methoxy.
R
3 is hydroxyl.
R
3 is chlorine.
R
4 is hydrogen, isopropyl, me-
R
4 is methyl.
R
4 is methoxy.
R
4 is hydroxyl.
R
4 is ethyl.
Compounds I are additionally preferred in which R 4 is isopropyl.
Compounds I are additionally preferred in which R 4 is cyclopropyl.
In addition, compounds I are preferred in which R 4 is aryl or hetaryl.
0050/44575 22 Compounds I are additionally preferred in which R 4 is phenyl.
Compounds I are additionally preferred in which R 5 is methyl or ethyl.
In addition, compounds I are preferred in which R 5 is arylalkyl or hetarylalkyl.
Compounds I are additionally preferred i which R 5 is aryloxyalkyl or hetaryloxyalkyl.
In addition, compounds I are preferred in which R 4 is unsubstituted or substituted aryl or hetaryl.
In addition, compounds I are preferred in which R 4 is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridaziryl or triazinyl.
In addition, compounds I are preferred in which R 4 is unsubstituted or substituted furyl, thienyl or pyrrolyl.
In addition, compounds I are preferred in which R 4 is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
In addition, compounds I are preferred in which R 4 is unsubstituted or substituted oxdiazolyl [sicl, thiadiazolyl or triazolyl.
Compounds I are additionally preferred in which R 4 is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Cl-C 4 -alkoxy,
C
1
-C
4 -haloalk )xy, C 1
-C
4 -alkylamino, di-C 1
-C
4 -alkylamino, Cl-C 4 -alkylsulfonyl, Cl-C 4 -alkoxycarbonyl, Ci-C 4 -alkylaminocarbonyl or di-C 1
-C
4 -alkylaminocarbonyl.
Compounds I are additionally preferred in which R 5 is aryl or hetaryl.
The compounds I compiled in the following tables are particularly preferred with respect to their use.
L v I- -a i g-- 0050/44575 23 Table 1 Compounds of the general formula I.1 in which (R 2 )m is hydrogen and the combination of the substituents R 3
R
4 and R 5 for a compound in each case corresponds to one line of Table A
R
3
R
5 O N NO CI
NO-C-
2 I.1 OCH3
O=C-SR
1 Table 2 Compounds of the general formula I.1 in which (R 2 )m is chlorine and the combination of the substituents R 3
R
4 and R 5 for a compound in each case corresponds to one line of Table A.
0050/44S375 KI&A4 7,' Table A No. RR4R 1 CR 3
CH
3
H
2 CR 3
CH
3
CR
3 3 CR 3
CH
3
C
2
H
4 CR1 3 1
CH
3 n-C 3
H
7 5 CR 3
CR
3 i-C 3
H
7 6 CR 3
CR
3 Cyclopropyl 7 CR 3
CR
3 n-C 4
H
9 8 CR 3
CR
3
S-C
4 H9 9 CR 3
CR
3 i-C 4
H
9
CR
3
CR
3 t-C 4
H
9 11 CR 3
CR
3 n-C 5
H
1 1 12 CR 3
CR
3 i-C 5
RH
1 1 13 CR 3
CR
3 neO-C 5
H
1 1 14 CR 3
CR
3 Cyclopentyl.
CR
3
CR
3 n-C 6
H
1 3 16 CR 3
CR
3 Cyclohexyl 17 CR 3
CR
3 n-CeH 1 7 18 CR 3
CR
3
CH
2
CH
2 Cl 19 CR 3
CR
3
(CH
2 4
CJ.
CR
3
CR
3
CH
2
CN
21 CR 3
CR
3
CH
2
CR
2
CN
22 CR 3
CR
3
(CH
2 3
CN
23 CR 3
CR
3
(CH
2 4
CN
24 CR 3
CR
3
(CH
2 6
CN
CR
3
CR
3 CyclohexylmethyJ.
26 CR 3
CR
3 2-Cyclohexyleth-1-yl 27 CR 3
CR
3 Cyclopropylmethyl 28 CR 3
CR
3 2-Cyclopropyleth-I-yl 29 CR 3
CR
3 2-Methoxyeth--y.
30 CR 3
CH
3 2-Ethoxyeth-1-yl 31 CR 3
CH
3 2-Isopropoxyeth-1-yl 3 2 CR 3
CR
3 3-Methoxyprop-1-y.
33 CR 3
CR
3 3-Ethoxyprop-1-yl 34 CR 3
CR
3 3-Isopropoxyprop-1-yl 35 CR 3
CR
3 4-Methoxybut-1-y.
36 CR 3
CR
3 4-Isopropoxybut-1-yl
I
0050/44575 No. RR4R 37 CH 3
CE
3 Propen-3-yl 38 CH 3
CH
3 But-2-en-1-yl 39 CE 3
CH
3 3-Methylbut-2-en-1-yl
CE
3
CE
3 2-Vinyloxyeth-1-yl 41 CE 3
CE
3 Allyloxyeth-1-yl 42 CE 3
CE
3 2-Trifluoromethoxyeth--1-yl 43 CE 3
CE
3 3-Trifluoromethoxyprop-1-yl 44 CE 3
CE
3 4-Difluoromethoxybut-1-y.
CE
3
CE
3 Hydroxycarbonylmethyl 46 CE 3
CE
3 Methoxycarbonylmethyl 47 CE 3
CE
3 Aininocarbonylmethyl 48 CE 3
CE
3 N-Methylaminocarbonylrnethyl 49 CE 3
CE
3 N,N-Dimethyaminocarbonylmethyl
CE
3
CE
3 2-Hydroxycarbonyleth-1-yl 51 CE 3
CE
3 2-Methoxycarbonyleth-1-yl 52 CE 3
CE
3 2-Aminocarbonyleth-1-yl 53 CE 3
CE
3 2-N-Methylaminocarbonyleth-1-y.
54 CE 3
CE
3 2-Dimethylaminocarbonyleth-1-yl
CE
3
CE
3 2-Axninoeth-1-yl 56 CE 3
CE
3 2-Axninoprop-1-y.
57 CH 3
CE
3 4-Aminobut-1-yl 58 CE 3
CE
3 3-Dimethylaminoprop-1-yl 59 CE 3
CE
3 4-Aminothiocarbonylbut-1-yl
CE
3
CE
3 2-Oxopropyl 62. CE 3
CE
3 Cyclohexyl 62 CE 3
CE
3 Cyclopropyl_____ 63 CE 3
CE
3 Cyclopentyl 64 Cl-I 3
CE?
3 2-Methoxyiminoprop-1-yl
CE
3
CE
3 2-Methoxyiminoeth-1-yl 66 CE 3
CE
3 6-Aminocarbonylhex-1-yl 67 CE 3
CE
3 3-Aminothiocarbonylprop-1-y.
68 CE 3
CH-
3 2-Axninothiocarbonyleth-1-y.
69 CE 3
CE
3 Aminothiocarbonylnethyl
CE
3
CE
3 4-(N,N-Dimethylbut-1-yl 71. CE 3
CE
3 2-(Methylthio)eth-1-yl 72 CE 3
CE
3 2-(Methylsulfonyl)eth-1-yl 0050/44I575 No. R 3 R4R 73 CH 3
CUH
3 4-(Methylthio)prop---yl 74 CH 3
CU
3 4-(Methylsulfonyl)prrn-1-y1 1 76 C3 CH32-F-C 6
H
4
-CH
2 77 CH CH33-F-C 6
H
4
-CH
2 78 CH CH34-F-C 6
H
4
-CH
2 79 CH CH32, 3-F 2
-C
6
UH
3
-CH
2 CH CH32, 4-F 2
-C
6
H
3
-CH
2 81 CU 3
CH
3 2,5-F 2
-C
6
H
3
-CH
2 82 CU 3
CU
3 2, 6-F 2
-C
6
H
3
-CH
2 83 CU 3
CH
3 3,4-F 2
-C
6
H
3
-CH
2 84 CH 3
CU
3 3 ,5-F 2
-C
6
H
3
-CH
2
CU
3
CH
3 2-C1--C 6
H
4
-CH
2 86 CU 3
CH
3 3-Cl-C 6
H
4
-CH
2 87 CU 3
CH
3 4-Cl-C 6
H
4
-CH
2 88 CU 3
CU
3 2, 3-Cl 2
-C
6
H
3
-CH
2 89 CU 3
CU
3 2, 4-Cl 2
-C
6
H
3
-CH
2
CH
3
CH
3 2,5-Cl 2
-C
6
H
3
-CH
2 91 CU 3
CU
3 2, 6-Cl 2
-C
6
H
3
-CH
2 92 CU 3
CU
3 3 ,4-Cl 2
-C
6
H
3
-CH
2 93 CU 3
CU
3 3,5-C 2
-C
6 3
-CH
2 94 CU 3
CU
3 2, 3, 4-C1 3 -CjlI,-CH 2
CU
3
CU
3 2,3,5-C 3
-C
6 2
-CH
2 96 CU 3
CU
3 2,3,6-C 3
-C
6
H
2
-CH
2 97 CU 3
CU
3 2, 4, 5-C1 3
-C
6
H
2
-CH
2 98 CU 3
CU
3 2, 4, 6-C 3
-C
6 2
-CH
2 99 CU 3
CU
3 3,4,5-C 3
-C
6
H
2
-CH
2 100 CU 3
CU
3 2-Br-C 6
U
4
-CH
2 101 CU 3
CU
3 3-Br-C 6
H
4
-CH
2 102 CU 3
CU
3 4-Br-C 6
H
4
-CH
2 103 CU 3
CU
3 2,3-Br 2
-C
6
U
3
-CH
2 104 CH 3
CU
3 2,4-Br 2
-C
6
H
3
-CH
2 105 CU 3 C 17- 3 2,5-Br 2
-C
6
H
3
-CH
2 106 CU 3
CU,
3 2, 6-Br 2
-C
6
H
3
-CH
2 107 CH 3
CU
3 3,4-Br 2
-C
6
H
3
-CH
2 108 CU 3
CU
3 31 5-Br 2
-C
6
U
3
-CH
2 109 1CU 3
CU
3 2-F, 3-Cl-C 6
H
3
-CU
2 110 ICU 3
ICU
3 2-F, 4-Cl-C 6
U
3
-CU
2 0050/'4s5 7S
"NO
No. RR4R 111 CU 3
CH
3 2-F, 5-Cl-C 6
H
3 -CH2 112 CH 3
CH
3 2-F, 3-Br-CGH 3
-CH
2 113 CH 3
CH
3 2- F, 4-Br-C 6
H
3
-CH
2 114 CU 3
CU
3 2-F, 5-Br-C 6
H
3
-CH
2 115 CU 3
CU
3 2-Cl, 3-Br-C 6
H
3
-CH
2 116 CU 3
CU
3 2-Cl, 4-Br-C 6
H
3
-CH
2 117 CU 3
CU
3 2-Cl, 5-Br-C 6
H
3
-CH
2 118 CU 3
CU
3 3-F, 4-Cl-C 6
H
3
-CH
2 119 CU 3
CU
3 3-F, 5-Cl-C 6
U
3
-CH
2 120 CU 3
CU
3 3-F, 6-Cl-C 6
H
3
-CH
2 121 CU 3
CU
3 3-F, 4-Br-C 6
U
3
-CU
2 122 CU 3
CU
3 3-F, 5-Br-C 6
U
3
-CU
2 12 3 CU 3
CU
3 3-F, 6-Br-C 6
U
3
-CU
2 124 CU 3
CU
3 3-Cl, 4-Br-C 6
U
3
-CU
2 125 CU 3
CU
3 3-Cl, 5-Br-C 6
H
3
-CU
2 126 dU 3
CU
3 3-Cl, 6-Br-C 6
U
3
-CU
2 127 CU 3
CH
3 4-F, 5-Cl-C 6
U
3
-CU
2 128 CU 3 C 4-F, 6-Cl-C 6
H
3
-CU
2 129 CU 3
CU
3 4-F, 5-Br-C 6
U
3
-CU
2 130 CU 3
CU
3 4-F, 6-Br-CGH 3
-CU
2 131 CU 3
CU
3 4-Cl, 5-Br-C 6
U
3
-CH
2 132 CU 3
CU
3 5-F, 6-Cl-C 6
U
3
-CU
2 133 CU 3 Ck 3 5-F, 6-Br-C 6
H
3 -CU2 134 CU 3
CU
3 5-Cl, 6-Br-C 6
U
3
-CH
2 135 CU 3
CU
3 3-Br, 4-Cl, 5-Br-C 6
U
2
-CU
2 136 CU 3 3 2-CN-C 6
H
4
-CH
2 137 CU 3
CU
3 3-CN-C 6
H
4
-CH
2 138 CU 3
CU
3 4-CN-C 6
H
4
-CH
2 139 CU 3
CU
3 2-N0 2
-C
6
H
4
-CH
2 140 CU 3
CU
3 3-N0 2
-C
6
H
4
-CU
2 141 CU 3
CU
3 4-N0 2
-C
6
H
4
-CH
2 142 CU 3
CH
3 2-CH 3
-C
6
H
4
-CU
2 143 CU 3
CU
3 3-CH 3
-C
6
H
4
-CH
2 144 CU, 3
CU
3 4-CH 3
-C
6
H
4
-CH
2 145 CU 3
CU
3 2,3-(CH 3 2
-C
6
H
3
-CH
2 146 CU 3
CU
3 2,4-(CH 3 2
-C
6
H
3
-CH
2 147 CU 3
CU
3 2,5-(CH 3 2
-CH
3
-CH
2 148 CU 3
CU
3 2,6-(CU 3 2
-C
6
H
3
-CH
2 0050/44575 x V-u jA3 No. R R 149 CH 3
CH
3 3, 4- (C 3 2
-C
6
H
3
-CH
2 150 CE 3
CE
3 3,5-(CH 3 )2-C 6 H3-CH 2 151 CE 3
CH
3 2-C 2
H
5
-C
6
H
4
-CH
2 152 CE 3
CE
3 3-C 2
H
5
-C
6
H
4
-CH
2 153 CE 3
CE
3 4-C 2
HS-C
6
H
4
-CH
2 154 CE 3
CE
3 2-i-C 3
H
7
-C
6
H
4
-CH
2 155 CE 3
CE
3 3-i-C3H 7
-C
6
H
4
-CH
2 156 CH 3
CE
3 4-i-C 3
E
7
-C
6
H
4
-CH
2 157 CE 3
CE
3 2-Cyclohexyl-C 6
H
4
-CH
2 158 CE 3
CE
3 3-Cyclohexyl-C 6
H
4
-CH
2 159 CE 3
CE
3 4-Cyclohexyl-C 6
H
4
-CH
2 160 CH 3
CE
3 2-Vinyl-C 6
H
4
-CE
2 161 CE 3
CE
3 3-Viriyl-C 6
H
4
-CE
2 162 CE 3
CE
3 4-Vinyl-C 6
H
4 -CH2 163 CE 3
CE
3 2-AllYl-C 6 4
-CH
2 164 CE 3
CE
3 3-Allyl-C 6
E
4
-CH
2 165 CE 3
CE
3 4-Allyl-C 6 4
-CH
2 166 CE 3
CE
3 2-C 6
E
5
-C
6
H
4
-CH
2 167 CE 3
CE
3 3-C 6
HS-C
6
H
4
-CE
2 168 CE 3
CE
3 4-C 6 Hr-C 6
H
4
-CH
2 169 CE 3
ICE
3 3-CE 3 5-t-C 4
E
9
-C
6
E
3
-CE
2 170 CE 3
CE
3 2-OE--C 6
H
4
-CE
2 171 CE 3
CE
3 3-OH-C 6
E
4
-CH
2 172 CE 3
CE
3 4-OH-C 6
H
4
-CH
2 173 CE 3
CE
3 2-OCH 3
-C
6
H
4
-CH
2 174 CE 3
CE
3 3-OCH 3
-C
6
H
4
-CE
2 175 CE 3
CE
3 4-OCH 3
-C
6
H
4
-CH
2 176 CE 3
CE
3 2,3-(OCH 3 2
-C
6
H
3
-CH
2 177 CE 3
CE
3 2,4- (OCH 3 2
-C
6
E
3
-CH
2 178 CE 3
CH
3 2, 5--(OCE 3 2
-C
6
E
3
-CE
2 179 CE 3
CE
3 3,4-(OCH 3 2
-C
6
H
3
-CH
2 180 CE 3
CE
3 3,5- (OCE 3 2
-C
6
H
3
-CE
2 181 CE 3
CE
3 3,4,5-(OC 3 3
-C
6 2
-CH
2 182 CE 3
CE
3 2-0C 2
E
5
-C
6
H
4
-CH
2 183 CE 3
CE
3 3-0C 2
E
5
-C
6
E
4
-CH
2 184 CE 3
CE
3 4-0C 2
H
5
-C
6
E
4
-CH
2 185 CE 3
CE
3 2-0- (n-C 3
H
7
-C
6
E
4
-CE
2 186 CE 3
ICE
3 3-0- (n-C 3
E
7
)-C
6
E
4
-CE
2 OOSO/44575 No. R 4R 187 CH 3
CU
3 14-0- (n-C 3
H
7
)-C
6
H
4
-CH
2 188 CH 3
CH
3 2-0-C(i-C 3
U.
7 -C6H 4
-CH
2 189 C-H 3
CU
3 3-0- (i-C 3
H
7
)-C
6
H
4
-CH
2 190 CU 3
CU
3 4-0- (i-C 3
H
7
)-C
6
H
4
-CU
2 191 CU 3 4 CH 3 4-0- (n-C 4
H
9
)-C
6
H
4
-C-H
2 192 CU 3
CH
3 3-0-(t-C 4 9
)-C
6
H
4
-CH
2 1931 CU 3
CU
3 4-0- (r-C 6
H
1 3
-C
6
H
4
-CH
2 194 CU 3
CU
3 2-0-,Allyl-CS 4
-CH
2 195 CUHU 3-0-AllYl-C 6 4
-CH
2 196 CU 3
CU
3 4-0-AllYl-C 6 4
-CH
2 197 CU 3
CU
3 2-CF3--C 6
H
4
-CH
2 198 CU 3
CU
3 3-CF 3
-C
6
U
4
-CH
2 199 CU 3
CU
3 4-CF 3
-C
6
H
4
-CH
2 200 CU- 3
CU
3 2-Acetyl-C 6
H
4
-CH
2 201 CU 3
CU
3 3-Acetyl-C 6
H
4
-CH
2 202 CU 3
CU
3 4-Acetyl-C 6
H
4
-CH
2 203 CU 3
CU
3 2-Methoxycarbonyl-C 6
H
4
-CH
2 204 CU 3
CU
3 3-Methoxycarbonyl-C 6
H
4
-CH
2 205 CU 3
CU
3 4-Methoxycarbonyl-C 6 4
-CH
2 206 CU 3
CU
3 2-Aminocarbonyl-C 6
H
4
-CH
2 207 CU 3
CU
3 3-Aminocarbonyl-C 6
U
4
-CH
2 4 208 CU 3
CU
3 4-Aminocarbony-C6H 4 -CH2___ 209 CU 3
CU
3 2-Dimethylamriocarbonyl-C 6
H
4
-CH
2 210 CU 3
CU
3 3-Dimethylaminocarbonyl-C 6
H
4
-CH
2 211 CH 3
CU
3 4-Diniwctyaminocarbo- 212 CU 3
CU
3 2-(N-Nethylaminocarbonyl )-C 6
H
4
-CH
2 213 CU 3
CU
3 3-(N-Methylaminocarbonyl )-C 6
H
4
-CU
2 214 CU 3
CU
3 4-(N-Methylaminocarbo- 215 CH 3
CU
3 .2-H 2
N-C
6
H
4
-CH
2 216 CU 3
CU
3 3-H 2
N-CGU
4
-CH
2 217 CU 3
CU
3 4-U 2
N-Q
6
U
4
-CH
2 218 CU 3
CU
3 2-Aminothiocarbonyl-CGH 4
-CH
2 219 CU 3
CU
3 3-Aiminothiocarbonyl-C 6
H
4
-CH
2 220 CU 3
CU
3 4-n :ohiocarbonyl-C 6
U
4 -CH2_ 0050/44575~ No. RR4R 221 CU 3
CU
3 2 -Methoxyimi nomethyl -C 6 4
-CH
2 222 CU 3
CU
3 3-Methoxyiminomethyl-C 6 4
-CH
2 223 CU 3
CU
3 4-Methoxyiminomethyl-C 6 4
-CH
2 224 CH 3 CU3 2-Formyl-C 6
H
4
-CH
2 225 CU 3
CU
3 3-Formvl-C 6
H
4
-CH
2 226 CU 3
CU
3 4-Formyl-C 6
H
4
-CH
2 227 CU 3
CH
3 2-(l'-Methoxyiminoeth-1 -C 6
H
4
-CH
2 228 CU 3
CU
3 3-(1',4vethoxyiminoeth-1 -C 6
H
4
-CH
2 229 CU 3
CU
3 4-(l'-Methoxyiminoeth-1 -C 6
U
4
-CU
2 230 CU 3
CU
3 2-SCH 3
-C
6
H
4
-CH
2 231 CU 3
CU
3 3-SCH 3
-C
6
H
4
-CH
2 232 CU 3
CU
3 4-SCH 3
-C
6
H
4
-CH
2 233 CU 3
CU
3 2-SO 2 CF1 3
-C
6
H
4
-CH
2 234 CU 3
CU
3 3-SO 2
CH
3
-C
6
H
4
-CH
2 235 CU 3
CU
3 4-SO 2
CU
3
-C
6
H
4
-CFU
2 1236 CU 3
CU
3 OC36H-2 -3 CU 3 CU -OCF 3
-C
6
U
4
CU
238 CU 3
CU
3 4-,OCF 3
-C
6
U
4
-CH
2 239 CU 3
CU
3 2-OCHF 2
-C
6
H
4
-CU
2 240 CU 3
CU
3 3-OCHF 2
-C
6
H
4
-CH
2 241 CU 3
CU
3 4-OCHF 2
-C
6
H
4
-CU
2 242 CU 3
CU
3 j 3-CF 3 4--OCF 3
-C
6
H
3
-CU
2 243 CU 3
CU
3 1-Naphthyl-CH 2 244 CU 3
CH
3 2-Naphthyl-CH 2 245 CU 3
CU
3 2-Phenoxyeth-1-yJ.
246 CU 3
CU
3 2-(2'-.Chlorophenoxy)eth-1.-yl 247 CU 3
CU
3 2-(3'-Chlorophenoxy)eth-1-yl 248 CU 3
CU
3 2-(4'.-Chlorophenoxy)eth-1-yl 249 CH 3
CU
3 250 U 3
C
3 2- 2~Cyanphenxy~eh---y 251 CU 3
CU
3 2-(3'-Cyanophenoxy)eth-1-yl 252 CU 3
CU
3 2-(4'-cyanophenoxy)eth-l-.yl 253 CU 3
CU
3 2- (2 '-Methyphenoxy) eth-1-y2.
254 CU 3
CU
3 2-(3'-Methylphenoxy)eth-1-yl 255 CU 3
CU
3 2-(4 '-Methylphenoxy)eth-1-yl 0050/44575 No. R 4R 256 CR 3
CH
3 2-(3'-t-Butylpheneth-1-yl 257 CR 3
CR
3 2-(4'-t-Butylphenoxy)- _____eth-1-yl 258 CH 3
CH
3 2- (2 '-Nitrophenoxy)eth-1-y.
259 CH 3
CH
3 3 -Nitrophenoxy)eth-1-yl 260 CR 3
CH
3 2-(4'-Nitrophenoxy)eth-1-yl 261 CH 3
CH
3 2-(2'-Methoxyphenoxy)- 262 CH 3
CR
3 2-(3'-Methoxyphenoxy)eth-1-yl 263 CR 3
CH
3 2-(4'-Methoxyphenoxy)eth-1-yl 264 CH 3
CR
3 2-(2'-Trifluoromethyleth-1-yl 265 CR 3
CR
3 2-(3'-Trifluoromethyl eth-1-yl 266 CR 3
CR
3 2-(4'-Trifluoromethyl )eth.-1-y.
267 CR 3
CR
3 2 -Acetylphenoxy)eth-1-yl 268 CR 3
CR
3 3 -Acetylphenoxy)eth---yl 269 CR 3
CR
3 4'-Acetylphenoxy)eth-1-yl 270 CR 3
CR
3 2-(2'-Methoxyeth-1-y.
271 CR 3
CR
3 2-(3'-Methoxyeth-1-yl 272 CR 3
CR
3 2-(4'-Methoxyeth-1-y.
273 CR 3
CR
3 2-(2'-Dimethylamino- 274 CR 3
CR
3 2-(3'-Dimethylaminocarbonyl )eth-1-y.
275 CR 3
CR
3 2-(4'-Dimethylaminocarbony)eth-1-yl 276 CR 3
CR
3 2-(2'-Aminothiocarbo- )eth- l-yl 277 CR 3
CR
3 2-(3'-Aminothiocarbonyl )eth-1-y.
278 CR 3
CR
3 2-(4'-Aininothiocarbo- )eth-1--yl 279 CR 3
CR
3 2-(2'-Methyl- )eth-1-y.
280 CR 3
CR
3 2-(3'-Methyl- )eth-1-yl 0050/44575 No. RR4R 281 CH 3
CH
3 2-(4'-Methyl- )eth-1-yl 282 CH 3
CR
3 3-Phenoxyprop-1-y.
283 OH 3
CH
3 3-(2'-Chlorophenoxy)prop- -y 2 284 CR 3
OH
3 3-(3'-Chlorophenoxy)prop- 1 -yJ- 285 CR 3
OH
3 3- -Chiorophenoxy )prop- -yl 286 CR 3
CR
3 3-(3',5',Dichlorophenoxy)- 287 CH 3
CR
3 3-(2'-Cyanophenoxy)prop-1-yl 288 CR 3
CR
3 3-(3'-Cyanophenoxy)prop-1-yl 289 CR 3
CH
3 3-(4'-Cyanophenoxy)prop-1-yl 290 CR 3
CH
3 3-(2'-Methylprop- 1-yl 293. OH 3
CH
3 3-(3'-Methyl- )prop- 1-yl 292 CH 3
CR
3 3-(4'-Methylphenoxy )prop- i-yi 293 CR 3 CR3 3-(2'-Methoxyphenoxy )prop- 1-yl 294 CH3 CH 3 3-(3'-Methoxyphen- 295 CH 3
CR
3 3-(4'-Methoxyphenoxy) prop-1-yl 296 CR 3
CR
3 3-(2'-Trifluoromethylpheioxy )prop-1-y.
297 CR 3
CR
3 3-(3'-Trifluoromethylphenprop-1-y.
298 CR 3
CR
3 3-(4'-Trifluorornethylphenoxy )prop-1-y.
299 CR 3
CR
3 4-Phenoxybut-1-yl 300 CR 3
CR
3 2-PhenyJleth-1-yl 301 CR 3
CH
3 2 -Chlorophenyl)eth-1-yl 302 CH 3
CR
3 3 -Chlorophenyl)eth-1-yl 303 CR 3
CR
3 4'-Chlorophenyl)eth-1-y.
304 CH 3
CRH
3 ,5'-Dichlorop ,'enyl)eth-1-yl 305 CR 3
CR
3 2 -Cyanophenyl)eth-1-yl 306 CR 3
CR
3 3 -Cyanophenyl)eth-1-yl 307 CR 3
CH
3 2-(4 '-Cyanophenyl)eth-1-y.
308 jCR 3
CR
3 2-(2 '-Methylphenyl)eth-1-y 0050/44575 No. R3145 309 CH 3
CH
3 2-(3'-Methylphenyl)eth-1-yl 310 CU 3
CU
3 4 -Methylphenyl)eth-1-yl 311 CH 3
CH
3 2- (2 '-Methoxyphenyl)eth-1-y.
312 CU 3
CH
3 3 -Methoxyphenyl )eth-1-yl 313 CU 3
CH
3 2-(4 '-Methoxyphenyl)eth-1-yl 314 CU 3
CH
3 2-(2'-TrifJluoromethylphenyl.) eth-1-yl 315 Cu 3
CU
3 2-(3'-Trifluoromethyleth-1-y.
316 CU 3
CH
3 2-(4'-Trifjluoromethylphenyl) eth-1-yl 317 CH 3
CH
3 3-Phenylprop-1-y.
318 Cu 3
CU
3 2 -Chlorophenyl~prop-1-yl 319 CU 3
CU
3 3 -Chlorophenyl)prop-1-yl 320 CU 3
CU
3 4 -Chlorophenyl)prop-1-yl 321 CU 3
CU
3 3-(2 '-Cyanophenyl)prop-1-yl 322 CU 3
CU
3 3-(3'-Cyanophenyl)prop-1-yl 323 CU 3
CH
3 4 -Cyanophenyl)prop-1-y 324 CU 3
CU
3 3-(2'-Trifluoromethy.- )prop-1-yl 325 CU 3
CU
3 4-Phenylbut-1-yl 326 CU 3
CU
3 4 -ChJlorophenyl)but-1-y.
327 CU 3
CU
3 6-(4 '-Chlorophenyl)hex-1-y- 328 CU 3
CU
3 2-Pyridylmethyl 329 CU 3
CU
3 3-Pyridylmethy.
330 CU 3
CU
3 4-Pyridylmethy.
331 CU 3
CU
3 4-Chloropyridin-2-ylmethy.
332 CU 3
CU
3 5-Chloropyridiri-2-ylmethyl 333 CU 3
CU
3 6-Chloropyridin-2-ylnethyl 334 CU 3
CU
3 5-Chloropyridin-3-ylmethyl 335 CU 3
CU
3 6-Chloropyridin-3--ylmethyl 336 CU 3
CU
3 2-chloropyridin-4-yJlmethyl 337 CU 3
CU
3 2-Pyrimidinylmethyl 338 CU 3
CU
3 4-Chloropyrimidin-2-ylmethyl 339 CU 3
CU
3 5-chloropyrimidin--2-ylme'thyl 340 CU 3
CU
3 2-Chloropyrimidin-4-ylmethyl 341 CU 3
CU
3 6-Chloropyrimidin-4-ylmethy.
342 CU 3
CU
3 343 CU 3
CU
3 4-Pyridazinylmethyl 344 CU 3 3 12-Pyrazinylmethyl 0050/44575 No. R3R 4
R
34 1~ 3 3 5-Chloropyrazin-2-ylmethyl 346 CR 3
CR
3 6-.Chloropyrazin-2-yl.methy.
347 CR 3
CH
3 3-Pyridazinylmethyl 348 CR 3
CH
3 6-Chloropyridazin-3-ylmethyl 349 CH 3
CR
3 1,3,5-Triazinylmethyl 350 CH 3
CH
3 2-Furylmethyl 352. CR 3
CH
3 3-Furylmethyl 352 CR 3
CR
3 4-Bromofur-2-yr'-Tyl 353 CR 3
CR
3 5-Chlorofur-2-ylmethyl 354 CR 3
CR
3 j 2-Thienylmethy.
355 CR 3
CR
3 3-Thienylmethyl 356 CH 3
CH
3 5-Methylthien-3-ylnethy.
357 CR 3
CR
3 5-Chlorothien-2-ylmethy.
358 CR 3
CH
3 2-Chlorothien-4-ylnethyl 359 CH 3
CR
3 2-Pyrrolylmethyl 360 CR 3
CR
3 3-Pyrrolylmethy.
361 CR 3
CR
3 2-Oxazolylmethyl 362 CR 3 c- 3 4-Methyloxazol-2-ylnethy.
363 CR 3
CR
3 5-Methyloxazol-2-ylmethy.
364 CH 3
CR
3 4-ChlorooxazoJ.-2-ylmethyl 365 CH 3
CR
3 1 5-ChlorooxazoJ.-2-ylmethyl 366 CR 3
CR
3 I4-Oxazolyirnethyl 367 CR 3
CR
3 12-Methylcxazol-4-ylmethyl 368 CR 3
CR
3 5-Methyloxazol-4-ylmethyl 369 CR 3
CR
3 2-Chlorooxazol-4-ylmethyl 370 CR 3
CR
3 5-Chlorooxazol-4If ylmethyl 371 CR 3
CR
3 372 CR 3
CR
3 373 CR 3
CR
3 374 CR 3
CR
3 375 CR 3
CR
3 4-Chlorooxazo.-S-ylmethy.
376 CR 3
CR
3 2-Thiazolylmethyl 377 CR 3
CH
3 4-Methylthiazol-2-ylmethyl 378 CR 3
CR
3 5-Methylthiazol-2-ylmethyl 379 CR 3
CR
3 4-Chlorothiazol-2-ylmethyl 380 CR 3
CR
3 5-Chlorothiazol-2-ylmethyl 31 CR 3
CR
3 4-Thiazolylmethy.
32 CR 3
CR
3 2-Methylthiazol-4-ylmethyl )000/ 440i7b A HA4 1 No. R30R R 383 CU 3
CU
3 5-Methylthiazol-4-ylmethyl 384 CU 3
CH
3 2-Chlorothiazol-.4-ylmethyl 385 CU 3 CH,? 5-Chlorothiazol-4-ylmethyl 386 CU 3 C11 3 387 CH 3
CU
3 388 CU 3
CU
3 389 CU 3
CH
3 390 CU 3 Ci-1 3 391 CU 3
CU
3 3-Isoxazolylmethyl 392 CU 3
CU
3 4-Methylisoxazol-3-ylmethyl 393 CH 3
CH
3 5-Methylisoxazol-3-ylmethyl 394 CU 3
CH
3 4-Chloroisoxazol-3-ylmethyl 395 CU 3
CH
3 5-Chlor-oisoxazol-3-ylmethyl 396 CU 3
CH
3 4-Isoxazolylmethy.
397 CU 3
CU
3 3-Methylisoxazol-4-ylmethyl 398 CH 3
CH
3 5-Methylisoxazol-4-ylmetbyl 399 CU 3
CH
3 3-Chloroisoxazol-4-ylmethy.
400 CH 3
CU
3 5-Chloroisoxazol-4-ylmethyl 401 CU 3
CU
3 402 CU 3
CU
3 403 ~CH 3
CU
3 404 CU 3
CU
3 405 TCH 3
CU
3 406 CU 3
CU
3 3-Isothiazolylmethyl 407 CU 3
CH
3 4-Methylisothiazol-3-yl- _____methyl 408 CU 3
CU
3 5-Methylisothiazol-3-yI- 409 CU 3
CU
3 4-Chloroisothiazol-3-yl- 410 CU 3
CU
3 5-Chloroisothiazol-3-ylmethyl 411 CU 3
CU
3 4-Isothiazolylmethyl 412 CU 3
CU
3 3-Eethylisothiazol-4-ylmethyl 4.13 CU 3
CU
3 5-Methylisothiazol-4-yl- ___methyl 414 413 CU 3 3-Chloroisothiazol-4-yl- ___methyl 415 5-Chloroisothiazol-4-ylmethyl
L
000/449$79 No. R 3 R4R 416 CV 3
CH
3 417 CU 3
CU
3 methyl' 418 CU 3
CH
3 419 CU 3
CH
3 methyl 420 CU 3 CH3 methyl 421 CU 3
CH
3 4-Imidazolylmethyl 422 CH 3
CH
3 1-Phenylpyrazol-3-ylmethyl 423 CU 3
CH
3 1-Methylimidazol-4--ylmethyl 424 CU 3
CH
3 1-Phenyl-1,2,4-triazol-3-yl- 425 CU 3
CH
3 1,2,4-oxadiazol-3-ylmethyl 426 CU 3
CU
3 5-Chloro-1,2,4-oxadiazol-3- _________ylmethyl 427 CU 3
CU
3 5-Methyl-1,2,4-oxadiazol-3ylmethyl 428 CU 3
CU
3 5-Trifluoromethyl-1,2,4- _______________oxadiazol-3-ylmethyl 429 CU 3
CH
3 1,3,4-Oxadiazol-2-ylmethyl 430 CU 3
CU
3 5-Chloro-1,3,4-oxadiazol-2- 43i. CU 3
CU
3 5-Methyl-1 4-oxadiazol-2ylmethyl_ 432 CU 3
CU
3 5-Methoxy-1,3,4-oxadiazol-2- ___ylmethyl 433 CU 3
CU
3 1,2,4-Thiadiazol-3-ylmethyl 434 CU 3
CU
3 5-Chloro-1,2,4--thiadiazol-3ylmethyl 435 CH 3
CU
3 5-Methyl-1,2,4-thiadiazol-3ylmethyl 436 CU 3
CU
3 1,3,4-Thiadiazol-2-ylmethyl 437 CU 3
CU
3 5-Chloro-1,3,4-thiadiazol-2- _________ylmethyl 438 CU 3
CU
3 5-Methyl-1,3..4-thiadiazol-2- 439 CU 3
CU
3 5-Cyano-1,3,4-thiadiazol-2ylmethyl 440 CU 3
CU
3 2-(2'-Pyridinyloxy)eth-1-yl 441 CU 3
CU
3 2-(3 '-Pyridinyloxy)eth-1-yl 442T CU 3
CU
3 2-(4 '-Pyridinyloxy)eth-1-yl 0050o/449791 No. R 3 R4R 443 CR 3
CR
3 2(21-Pyrimidinyloxy )eth-1-y.
444 CR 3
CR
3 2-(4'-Pyrimidinyloxy) eth-1-yl 445 CH 3
CR
3 eth-1-yl 446 CR 3
CH
3 2-(2'-Pyrazinyloxy)eth-1-yl 447 CH 3
CR
3 2-(2'-Pyridazinyloxy) eth-1-y 448 CR 3
CH
3 2-(3'-Pyridazinyloxy )eth-1-yl 449 CH3 CH 3 2-(1',3',5'--Triazinyloxy) eth-1-yl 450 CR 3
CR
3 2-(5'-Methylisoxazol-3'-yleth-1-yl 451 CH 3
CR
3 2-(5'-Chloroisoxazol-3'-yloxy) eth-1-y.
452 CR 3
CR
3 2-(2'-Methoxythiazol-4'-yloxy)eth-1-yl 453 CR 3
CR
3 2-(4'-Chlorooxazol-2'-yloxy)eth-l-.yl 454 CR 3
CH
3 2-(l'-Phenyl--1'H-1',2',4'triazol-3 '-yloxy) eth.-1-yl 455 CR 3
CR
3 2-(l'-Phenylpyrazol-3'-yloxy) eth-1-yl 456 CH 3
CH
3
C
6
H
457 CR 3
CR
3 2-Cl-C 6
R
4 458 CH 3
CR
3 3-Cl-C 6
H
4 459 CR 3
CR
3 4-Cl-C 6
H
4 460 CR 3
CR
3 2,3-C.
2
-C
6
R
3 461 CR 3
CH
3 2,4-Cl 2
-C
6
H
3 462 CR 3
CR
3 2,5-Cl 2
-C
6
H
3 463 CR 3
CR
3 3,4-Cl 2
-C
6
H
3 464 CR 3
CR
3 3,5-Cl 2
-C
6
H
3 465 CR 3
CR
3 4-CN-C 6
H
4 466 CR 3
CR
3 2-N0 2
-C
6
H
4 467 CR 3
CR
3 3-N0 2
-C
6 11 4 468 CR 3
CR
3 4-N0 2
-C
6
H
4 469 CR 3
CR
3 2,4-(N0 2 2
-C
6
H
3 470 CR 3
CR
3 2-CH 3
-C
6
H
4 471 CR 3
CR
3 3-CH 3
-C
6
H
4 472 CR 3
CR
3 4-CH 3
-C
6
H
4 000~0 /44970/ No. R 4R 473 CE 3
CE
3 2f3-(CH 3 2
-C
6
H
3 474 CE 3
CE
3 2, 4- (CH 3 2
-C
6
H
3 475 CH 3
CE
3 2,5-(CH 3 2
-C
6
H
3 476 CE 3
CE
3 2,6-(CH 3 2
-C
6
E
3 477 CE 3
CE
3 2-C 6
HS-C
6
H
4 478 CE 3
CE
3 3-C 6
HS-C
6
H
4 479 CE 3
CE
3 4-C 6 1- 5
-C
6
H
4 480 CE 3
CE
3 3-OCH 3
-C
6
H
4 481 CE 3
CE
3 4-OCH 3
-C
6
H
4 482 CH 3
CE
3 3-Acetyl-C 6
H
4 483 CH 3
CH
3 4-Acetyl-C 6
H
4 484 CH 3
CE
3 3-Methoxycarbonyl-C 6
H
4 485 CE 3
CH
3 4-.Methoxycarbonyl-C 6
H
4 486 CE 3
CE
3 3-CF 3
-C
6
H
4 487 CE 3
CE
3 4-.CF 3
-C
6
H
4 488 CE 3
CH
3 2-Naphthyl 489 CE 3
CE
3 6-Chloropyridazin-3-yl 490 CE 3
CE
3 5-Chloropyrazin-2-yl 491 CE 3
CE
3 Quinolin-2-yl 492 CE 3
CE
3 2,5-Dimethyl.pyrazin-3-yl 493 CE 3
CE
3 Pyrazin-2-yl 494 CE 3
CE
3 3-Chloropyrid-2-y.
495 CE 3
CH
3 6-Chloropyrid-2-yl 496 CH 3
CE
3 4-Trifluoromethy sic], 6-Chloropyrid- 2-yJ.
497 CE 3
CE
3 4-Trifluoromethylpyrid-2-yl 498 CE 3
CE
3 6-Trifluoromethylpyrid-2-yl 499 CE 3
CE
3 6-Methoxypyrid-2-yl 500 CE 3
CE
3 5-Chloropyrid-2-y.
501 CE 3
CE
3 Pyrid-2-yJ.
502 CE 3
CE
3 Benzothiazol-2-yl 503 CE 3
CH
3 7-Chloroquinolin-4-yl 504 CE 3
C.H
3 3-Nitropyrid-2-y.
505 CE 3
CE
3 Pyrrol-3-yl 506 CE 3
CE
3 Pyrrol-2-y.
507 CE 3
CE
3 2,6-Dioctylpyrid-4-yl 508 CE 3
ICE
3 5-Nitropyrid-2-yl 509 CE 3
CE
3 Pyrid-4-y.
510 'CE 3
CE
3 Pyrid-3-yl 000fl0 /440~7 511 CU 3
CH
3 Pyrimiclin-2-y.
512 CU 3
CU
3 Pyrimidin-4-yl 513 CU 3
CU
3 Quinazolin-4-yl 514 CU 3
CU
3 6-Chloropyrimidin-4-y.
515 CU 3
CU
3 6-Methoxypyrimidin-4-y.
516 CU 3
CU
3 2,5,6-Trichloropyrimidin- 4-yl 517 CU 3
CH
3 2,6-Dimethylpyrimidin-4-yl 518 CU 3
CU
3 2-Methyl, 6-Chloropyrimidin-4-yl [sic] 519 CU 3
CU
3 2-Methyl, 6-Ethoxypyrimi- ___din-4-yl (sic] 520 CU 3
CU
3 4,5,6-Trichloropyrimidin- 2-yl 521 CU 3
CU
3 4,6-Dimethoxypyrimidin-2-y.
522 CU 3
CU
3 4,6-Dimethylpyzimidin-2-yl 523 CU 3
CU
3 4,6-Dichloropyrimidin-2-y.
524 CU 3
CU
3 4-Methyl, 6-methoxypyrimidin-2-yl (sic] 525 CU 3
CU
3 4-Chloro, 6-methoxypyrimidin-2-y. [sic] 526 CU 3
CU
3 6-Chloroquinoxalin-2-yl 527 CU 3
CU
3 3,6-Dichloro-1,2,4-tri- 528 CU 3
CU
3 4-Methoxy-1,3,5-triazin-2-y.
529 CU 3
CU
3 4-Ethoxy-1,3,5-triazin-2-y.
530 CU 3
CU
3 4,6-Dichloro-1,3,5-tri- _____azin-2-yl 531 CU 3
CU
3 4-Ethoxy, 6-Chioro- [sic] 532 CU 3
CU
3 -isoxazol-3-y.
533 CU 3
CU
3 Thien-2-yl 534 CU 3
CH
3 Fur-2-yl 535 CU 3
CU
3 536 CU 3
CU
3 (E)-1-Chloropropen-3-y.
537 CU 3
CU
3 (E)-4-(4'-Chlorophenyl)but- 2-en-i -yl 538 CU 3
CU
3 Propyn-3-yl 539 CU 3
CU
3 Methylcarbony.
540 CU 3
CU
3 Ethylcarbonyl 541 CU 3
CU
3 n-Propylcarbonyl 542 CU 3
CU
3 i-Propylcarbonyl 0000/44970 No. R 3 R4A RS 543 CU 3
CR
3 n-Butylcarbony.
544 CH3 CR 3 s-Butylcarbonyl 545 CR 3
CH
3 i-Butylcarbony.
546 CH 3
CH
3 t-Butylcarbony.
547 CU 3
CU
3 n-Pentylcarboiyl 548 CR 3
CH
3 i-Pentylcarbonyl 549 CH3 CH 3 neo-Pentylcarbonyl 550 CU 3
CH
3 n-Hexylcarbonyl 551 CU 3
CH
3 n-octylcarbony.
552 CR 3
CU
3 1-Propenylcarbonyl 553 CR 3
CU
3 2-Penten-1-yl-carbony.
554 CU 3
CH
3 2,5-Heptadien-1-ylcarbonyl 555 CU 3
CU
3 Benzoy.
556 CU 3
CU
3 2-Chlorobenzoy.
557 CH 3
CU
3 3-Chlorobenzoy.
558 CH 3
CU
3 4-Chlorobenzoyl 559 CU 3
CR
3 2-Cyanobenzoyl 560 CU 3
CU
3 3-Cyanobenzoy.
561 CU 3
CH
3 4-Cyanobenzoyl 562 CR 3
CR
3 4-Methoxybenzoyl 563 CU 3
CH
3 2-Pyridylcarbony.
564 CR 3
CU
3 3-Pyridylcarbonyl 565 CR 3
CR
3 4-Pyridylcarbonyl 566 CR 3
CR
3 2-Pyrimidinylcarbony.
567 CU 3
CU
3 2-Oxazolylcarbonyl 568 CR 3
CU
3 carbonyl 569 CU 3
CR
3 Methylsulfony.
570 CR 3
CU
3 Ethylsulfonyl 571 CU 3
CU
3 n-Propylsulfonyl 572 CR 3
CH
3 i-Propylsulfonyl 573 CU 3
CU
3 n-Butylsulfonyl 574 CU 3
CU
3 t-Butylsulfony.
575 CU 3
CR
3 n-Pentylsulfonyl 576 CU 3
CU
3 neo-Pentylsulfony.
577 CR 3
CH
3 n-Hexylsulfonyl 578 CU 3
CU
3 n-Octylsulfony.
57 CU CU 3 Phenylsulfonyl 0000/ 44373 No. R 3
R.
4
R
580 CU 3
CU
3 2-Chlorophenylsulfony.
581. CU 3
CH
3 3-Chlorophenylsulfony.
582 CU 3
CU
3 4-Chlorophenylsulfonyl 583 CU 3
CH
3 2-Cyanophenylsulfonyl 584 CU 3
CU
3 3-Cyanophenylsulfonyl 585 CU 3
CU
3 4-Cyanophenylsulfony.
586 CU 3
CH
3 2-Pyricdylsulfony.
587 CU 3
CH
3 3-Pyridylsulfonyl 588 CU 3
CU
3 4-Pyridylsulfonyl 589 CU 3
CH
3 2-Pyrimidinylsulfonyl 590 CU 3
CH
3 4-Oxazolylsulfonyl 591 CH 3
CU
3 5-Chlorothiazol-2y.sulfonyl 592 CH 3
CU
3 2-t-C 4
U
9
-C
6
H
4
-CH
2 593 CU 3
CU
3 3-t-C 4
H
9
-C
6
H
4
-CH
2 594 CH 3
CH
3 4-t-C 4 g-C 6 4
-CH
2 595 CH 3
CU
3 2-(4'-Chlorothiazol-2' yl- )eth-1-yl 596 CU 3
CH
3 2-(1'-Methylpyrazol-4'-y.- )eth-1-y2 597 CU 3
CU
3 4-Br-C 6
H
4 598 CU 3
CU
3 1 3,5-(CU 3 2
-C
6
H
3 599 CU 3
CH
3 4-C 2
H
5
-C
6
U
4 600 CU 3
CU
3 3-Dimethylaminocarbonyl-C 6 U4 601 CU 3
CU
3 4-Dimethylaminocarbonyl-C 6 H4 602 CU 3
CU
3 2-Hydroxyprop-1-yJ.
603 CU 3
CU
3 6-Hydroxy-2-methy2.pyrimidin- 4-ylmethyl 604 CU 3
CU
3 [6-OU,2-CH(CH 3 2 -pyrimidin-4- YlJ -CU 2 605 CU 3
CU
3 (6-OU,2-CU(CH 2 2 -pyrimidin-4yl) -CU 2 606 CU 3
CH
3 5-(2'-Furan)-pent-1-yl 607 CU 3
CU
3 5-(2'-N--Methylpyrro))-pent-1-yl 608 CU 3
CU
3 (4-cl-C6U 4 -OXazol-4-yl)-
CU
2 609 CU 3
CU
3 3-CF 3 -pyridin-2-yl 610 CU 3
CH
3 5-CF 3 -pyridin-2-yl 611 CU 3
CH
3 6-(2'-Thienyl)hex-1-yl 612 ICU 3 It-C 4 Ug U 0050449180 No. RR4R 613 CE 3 t-C 4
H
9
CH
3 614 CH 3 t-C 4
H
9
C
2
HS
615 CH 3 t-C 4 H9 n-C 3
H
7 616 CE 3 t-C 4
H
9 i-C 3
H
7 617 CH 3 t-C 4
H
9 Cyclopropyl 618 CE 3 t-C 4 H9 n-C 4 H9 619 CE 3 t-C 4
H
9 t-C 4
H
9 620 CH 3 t-C 4 H9 n-C 6
HI
3 621 CH 3 t-C 4 Eg (E)-1-Chloropropel-3-yl 622 CE 3 t-C 4 H9 Propyn-3-yJ.
623 CE 3 t-C 4 H9 3-Methylbut-2-el- 1-yJ.
624 CH 3 t-C 4
E
9 2-Naphthyl-CH 2 625 CE 3 t-C 4 H9 4-C1-C 6
H
4
-CH
2 626 CE 3 t-C 4 H9 (E)-4-(4'-Chlorophel)but-2 -en-1-yl 627 CE 3 t-C 4
H
9 6-(4'-Chloropheflyl)hex-1-yl 628 CH 3 t-C 4 H9 3-CF 3 -C6H 4 629 CE 3
C
6
H
5
H
630 CE 3
C
6
H
5
CE
3 631 CE 3
C
6
H
5
C
2
H
632 CE 3
C
6
H
5 n-C 3 H-7 633 CE 3
C
6
H
5 i-C 3
H
7 634 CE 3
C
6
H
5 cyclopropyl 635 CE 3
C
6 Hs n-C 4
H
9 636 CE 3
C
6
H
5 t-C 4 H9 637 CE 3
C
6
E
5 n-C 6
H
1 3 638 CE 3
C
6
HE
5 4-Cl-C 6
H
4
-CH
2 639 CE 3
C
6
H
5 3-CF 3 -CGE4 640 CE 3
C
6
H
5 6- -Chlorophenyl.) hex-1-yl 641 CE 3 CGH5 (E)-4-(4'-Chlorophel)but- 2-en-1-y.
642 CE 3 H
H
643 CE 3 H CE 3 644 CE 3 H
C
2
HS
645 CE 3 H n-C 3
H
7 646 CE 3 H i-C 3
H
7 647 CE 3 OH
H
648 CE 3 OH CE 3 649 CE 3 OH
C
2
H
0000/4075h No.- R 3 R4R 650 CU 3 OH n-C 3
H-
7 651. CH 3 OH iCH 652 CU 3 Cl CU 3 653 CH 3 Cl C 2
H
654 CU 3 Cl n-C 3
H
7 655 CU 3 Cl iCH 656 CU 3
OCH
3
H
657 CU 3
OCH
3
CU
3 658 CU 3
OCH
3
C
2
H
659 CH 3
OCH
3 n-C 3
U
7 660 CU 3
OCH
3 iCH 661 CU 3
SCH
3
H
662 CU 3
SCH
3
CU
3 663 CU 3
SCH
3
C
2
HS
664 CU 3
SCU
3 n-C 3
H
7 665 CU 3
SCU
3 i-C 3
H-
7 666 CU 3 Cyclopropy2. H 667 CU 3 Cyclopropyvl ICU 3 668 CU 3 CyclopropyJ. C 2
HS
669 CU 3 CyclopropyJ. n-C 3
U
7 670 CU 3 Cyclopropy). i-C 3
H
7 671 CU 3 2--Pyridyl
H
672 CU 3 2-Pyridyl CU 3 673 CU 3 2-Pyridyl C 2
H
674 CU 3 2-Pyridyl n-C 3
H
7 675 CU 3 2-Pyridyl i-C 3
H
7 676 CU 3 3-Pyridyl H 677 CU 3 3-Pyridyl CU 3 678 CU 3 3-Pyridy. C 2
U
679 CU 3 3-Pyridy. n-C 3
H
7 680 CU 3 3-Pyridyl 681 CU 3 4-Pyridyl
U
682 CU 3 4-Pyridyl CU 3 683 CU 3 4-Pyridyl
C
2
HUS
684 CU 3 4-Pyridyl 685 CU 3 4-Pyridy. li-C 3
U
7 686 CU 3 2-Pyridimidyl U 687 CU -yiiiyl CU 3 0090/44rfl6 No. RR4R 688 CH 3 2-Pyridimidy). C 2
HS
689 CU 3 2-Pyridimidyl n-C 3
H
7 690 CU 3 2-Pyridimidy). i-C 3
H
7 691 CU 3 4-Pyridimidy H 692 CU 3 4-Pyridimidy. CU 3 693 CU 3 4-Pyridimidyl C 2
H
694 CU 3 4-PyridimidyJ. n-C 3
H
7 695 CU 3 4-Pyridimidyl iCH 696 CU 3 5-Pyridimidyl H 697 CH 3 5-Pyridimidy. CU 3 698 CU 3 5-Pyridimidyl C 2
HS
699 CU 3 5-Pyridimidy. n-C 3
H
7 700 CU 3 5-Pyridimidy. i-C 3
U
7 701 CU 3 1,3,5-Triazinyl U 702 CU 3 1,3,5-Triazinyl CU 3 703 CU 3 1,3,5-Triazinyl C 2
U
704 CU 3 1,3,5-Triaziny. n-C 3
U
7 705 CU 3 1,3,5- Ilriazinyl i-C 3
H
7 706 CU 3 2-Furyl U 707 CU 3 2-Furyl CU 3 708 CU 3 2-Furyl C 2
H
709 CU 3 2-Furyl n-C 3
H
7 710 CU 3 2-Furyl i-C 3
H
7 711 CU 3 3-Furyl U 712 CU 3 3-Furyl CU 3 713 CU 3 3-Furyl
C
2
HU
714 CU 3 3-Furyl n-C 3
H
7 715 CU 3 3-Furyl i-C 3
H
7 716 CU 3 2-Thienyl
U
717 CU 3 2-Thieny. CU 3 718 CU 3 2-Thienyl
C
2
H
719 CU 3 2-Thienyl n-C 3
H
7 720 CU 3 2-Thienyl i-C 3
H
7 721 CU 3 3-Thieny. H 722 CU 3 3-Thienyl CU 3 723 CU 3 3-Thieny. C 2
U
724 CU 3 3-Thienyl n-C 3
U
7 725 ICU 3 3-Thienyl iCU 00 !00 /449~7 No. R 3 R4R 726 CU 3 2-Oxazoly2.
727 CU 3 2-Oxazolyl CU 3 728 CU 3 2-Oxazolyl C 2 729 CH 3 2-Oxazolyl n-C 3
U
7 730 CH 3 2-Oxazoly2. i-C 3
HU
7 731 CU 3 4-Oxazolyl H 732 CU 3 4-Oxazolyl CH 3 733 CU 3 4-OxazolyJ. C 2
H
734 CU 3 4-Oxazolyl n-C 3
H
7 735 CU 3 4-Oxazolyl i-C 3
H
7 736 CU 3 I2-Thiazolyl H 737 CU 3 2-Thiazoly. CU 3 738 CU 3 2-ThiazolyJ. C 2
H
739 CU 3 2-ThiazoJlyl n-C 3
H
7 740 CU 3 2-Thiazoly). :-C 3
H
7 741 CU 3 4-Thiazolyl H 742 CU 3 4-Thiazoly. CU 3 743 CU 3 4-Thiazoly. C 2
H
744 CU 3 4-Thiazoly. n-C 3
H
7 745 CU 3 4-Thiazolyl i-C 3
H
7 746 CU 3 3-Isoxazolyl U 747 CU 3 3-Isoxazolyl CU 3 748 CU 3 3-Isoxazoly. C 2
H
749 CU 3 3-Isoxazolyl n-C 3
H
7 750 CU 3 3-Isoxazolyl n.-C 3
H
7 751 CU 3 5-Isoxazolyl H 752 CU 3 5-Isoxazolyl CU 3 753 CU 3 5-Isoxazoly. C 2
HS
754 CU 3 5-Isoxazoly. n-C 3
H
7 755 CU 3 5-Isoxazolyl i-C 3
H
7 756 CU 3 2-Imidazolyl H 757 CU 3 2-Imidazolyl CU 3 758 CU 3 2-Iiidazoly. C 2
H
5
S
759 CU 3 2-Imidazolyl n-C 3
H
7 760 CH 3 2-Imidazoly i-C 3
H
7 761 CU 3 3-Pyrazolyl H 762 CU 3 3-Pyrazoly. CU 3 73 CU 3 3-Pyrazolyl I 2
U
005/4467rfl '0A No. R 3 R R 764 CH- 3 3-Pyrazolyl n-C 3
H
7 765 CH 3 3-Pyrazolyl i-C 3
H
7 766 CE 3 4-Pyrazolyl H 767 CE 3 4-Pyrazolyl CH 3 768 CH 3 4-Pyrazolyl C 2
H
769 CE 3 4-Pyrazoly. n-C 3
H
7 770 CE 3 4-Pyrazolyl -CH 771 OCH 3 H H 772 OCH 3 H CH 3 773 OCH 3 H C 2
H
774 OCH 3 H n-C 3
H
7 775 OCH 3 H i-C 3
H
7 776 OCH 3 OH H 777 OCH 3 OH CH 3 778 OCH 3 OH C 2
H
779 OCE 3 OH n-C 3
H
7 780 OCE 3 OH iCH 781 OCE 3 Cl n-C 4
H
9 782 OCE 3
CE
3 783 OCH 3 Cl
C
2
H
784 OCH 3 Cl n-C 3
H
7 785 OCH 3 Cl i-C 3
H
7 786 OCE 3
OCH
3
H
787 OCE 3
OCH
3
CH
3 788 OCE 3
OCH
3
C
2
H
789 OCE 3
OCH
3 n-C 3
E
7 790 OCH 3
OCH
3 i-C 3
H
7 791 OCH 3
SCH
3
H
792 OCH 3
SCH
3
CH
3 793 OCE 3
SCH
3
C
2
H
794 OCH 3
SCH
3 n-C 3
H
7 795 OCH 3
SCH
3 i-C 3
H
7 796 OCE 3
CH
3
H
797 OCH 3
CH
3
CE
3 798 OCH 3
CH
3
C
2
E
799 OCH 3
CE
3 n-C 3
H
7 800 1OCH 3
CE
3 i-C 3
H
7 801 JOCH 3 cyclopropyl
H
0090/44975 No. R 4Rs 802 OCR 3 Cyclopropyl CH 3 803 OCR 3 Cyclopropy. C 2
H
804 OCR 3 Cyc2.opropyl n-C 3
H
7 805 OCH 3 Cyclopropy. 806 OCH 3 2-Pyridyl H 807 OCR 3 2-Pyridyl. CH 3 808 OCH 3 2-Pyridy. C 2
H
809 OCH 3 2-Pyridyl n-C 3
R
7 810 OCR 3 2-Pyridyl i-C 3
R
7 812. OCR 3 3-Pyridyl H 812 OCR 3 3-Pyridyl CR 3 813 OCR 3 3-Pyridyl C 2
R
814 OCR 3 3-Pyridyl n-C 3
H
7 815 OCR 3 3-Pyridyl iCH 816 OCH 3 4-Pyridyl H 817 OCR 3 4-Pyridyl CR 3 818 OCR 3 4-Pyridyl C 2
HR
819 OCR 3 4-Pyridyl n-C 3 H7 820 OCR 3 4-Pyrimidyl i-C 3
H
7 821 OCR 3 2-Pyrimidyl H 822 OCR 3 2-PyrimidyJ. CR 3 823 OCR 3 2-Pyrimidy). C 2
H
824 OCR 3 2-Pyrimidy. n-C 3
H
7 825 OCR 3 2-Pyrimidy- i-C 3
R
7 826 OCR 3 4-Pyrirnidyl H 827 OCR 3 4-Pyrimidy. CR 3 828 OCR 3 4-Pyrimidy. C 2
R
829 OCR 3 4-Pyrimidy. n-C 3 R7 830 OCR 3 4-Pyrimidyl iCH 831 OCR 3 5-Pyrimidy. H 832 OCR 3 5-Pyrimidyl. CR 3 833 OCR 3 5-Pyrimidyl C 2
R
834 OCR 3 5-Pyrimidyl n-C 3
H
7 835 OCR 3 5-Pyrimidyl i-C 3
R
7 836 OCR 3 1,3,5-Triazinyl. H 837 OCR 3 1,3,5-Triaziriyl CR 3 838 1OCR 3 1,3,5-Triaziny. C 2
R
839 JOCR 3 1,3,5-Triaziy. n-C 3
R
7 005/ 40 i73 No. R 3 R4S 840 0CM 3 1,3,5-Triaziny. i-C 3
H
7 841 0CM 3 2-Furyl H 842 0CH 3 2-Furyl CH 3 843 OCH 3 2-Furyl C 2
M
844 0CM 3 2-Furyl n-C 3
H
7 845 OCM 3 2-Furyl ,i-C 3
H
7 846 0CH 3 3-Furyl H 847 OCH 3 3-Furyl CH 3 845 0CM 3 3-Furyl C 2
H
849 0CH 3 3-Furyl n-C 3
M
7 850 0CM 3 3-Furyl i-C 3 H7 851 0CM 3 2-Thienyl H 852 0CM 3 2-Thienyl CM 3 853 0CM 3 2-Thicayl C 2
H
854 0CM 3 2-Thienyl n-C 3
H
7 855 0CM 3 2-Thienyl. i-C 3
M
7 856 0CM 3 3-Thienyl H 857 OCM 3 3-Thienyl CH3 858 0CH 3 3-Thienyl
C
2
HS
859 0CM 3 3-Thienyl n-C 3
H
7 860 0CM 3 1 3-Thienyl i-C 3
H
7 861 0CM 3 12-Oxazolyl H 862 OCH 3 12-oxazolyl CM 3 863 0CM 3 2-Oxazolyl C 2
HS
864 0CM 3 2-OxazolyJ. n-C 3
H
7 865 0CM 3 2-Oxazolyl i-C 3
H
7 866 0CM 3 4-Oxazolyl H 867 0CM 3 4-Oxazolyl CM 3 868 0CM 3 4-Oxazolyl C 2
H
869 0CM 3 4-Oxazolyj. n-C 3
H
7 870-T6CZ1 3 4-OxazolyJ. i-C 3
F
7 871 0CM 3 *2-Thiazolyl H 872 OCH 3 2-Thiazoly). CM 3 873 0CM 3 j 2-Thiazolyl C 2
M
874 0CM 3 2-Thiazoly). n-C 3
H
7 875 0CM 3 2-ThiazoJlyl i-C 3
H
7 876 0CM 3 4-ThiazoJlyl H 877 0CM 3 4-ThiazolyJ. CM 3 0050/44579 110 R R R 878 OCH 3 4-Thiazoly. C 2
H
879 0CH 3 4-Thiazolyl n-C 3
H
7 880 OCH 3 4-Thiazolyl i-C 3
H
7 881 OCH 3 3-Isoxazolyl H 882 OCH 3 3-Isoxazolyl CH 3 883 OCH 3 3-Isoxazolyl C 2
H
884 OCH 3 3-Isoxazolyl n-C 3
H
7 885 O)CH 3 3-Isoxazolyl i-C 3
H
7 886 OCH 3 5-.Isoxazolyl. H 887 OCH 3 5-Isoxazolyl CH 3 888 OCH 3 5-Isoxazoly. C 2
H
889 OCH 3 5-Isoxazolyl n-C 3
H
7 890 OCH 3 5-Isoxazolyl i-C 3
H
7 891 OCH 3 2-Irnidazolyl H 892 OCH 3 2-Irftidazolyl CH 3 893 OCH 3 2-Imidazoly. C 2
HS
894 OCH 3 2-Imidazolyl n-C 3
H
7 895 OCH 3 2-Imidazolyl i-C 3
H
7 896 OCH3 3-Pyrazolyl H 897 OCH 3 3-Pyrazoly. CH 3 898 OCH 3 3-Pyrazolyl C 2
HS
899 OCH 3 3-Pyrazolyl n-C 3
H
7 900 OCH 3 3-Pyrazoly. i-C 3
H
7 901 OCH 3 4-Pyrazolyl H 902 OCH 3 4-Pyrazoly. CH 3 903 OCH 3 4-Pyrazoly. C 2
H
904 OCH 3 4-Pyrazoly. n-C 3
H
7 905 OCH 3 4-Pyrazolyl i-C 3
H
7 906 OH IH H 907 OH H CH3 908 OH H C 2
HS
909 OH H n-C 3
H
7 910 OH H i-C 3
H
7 911 OH OH 912 OH olCH 3 913 OH OH C 2
HS
914 OH n-C 3
H
7 0050/4457S No. R R 915 OH OH iCH 916 OH cl n-C 4
H
9 917 OH Cl CH 3 918 OH Cl C 2
H
919 OH Cl n-C 3
H
7 920 OH Cl i-C 3
H
7 921 OH OCH 3
H
922 OH OCH 3
CH,%
923 OH OCH 3
C
2
HS
924 OH OCH 3 n-C 3
H
7 925 OH OCH 3
'-C
3
H
7 926 OH SCH 3
H
927 OH SCH 3
CH
3 928 OH SCH 3
C
2
H
929 OH SCH 3 n-C 3
H
7 930 OH SCH 3 i-C 3
H
7 931 OH CH 3
H
932 OH CH 3
CH
3 933 OH CH 3
C
2
H
934 OH CH 3 n-C 3
H
7 935 OH CH 3 i-C 3
H
7 936 OH Cyclopropyl H 937 OH Cyclopropy. CH 3 938 OH Cyclopropyl C 2
H
939 OH Cyclopropy. n-C 3
H
7 940 OH Cyclopropyl i-C 3
H
7 941 OH 2-Pyridyl H 942 OH 2-Pyridyl CH 3 943 OH 2-Pyridyl C 2
H
5 q 944 OH 2-Pyridyl n-C 3
H
7 945 OH 2-Pyridyl i-C3H 7 946 OH 3 -Pyridyl H 947 OH 3-Pyridyl CH 3 948 OH 3-Pyridyl C 2
H
949 OH 3-Pyridyl n-C 3
H
7 950 OH 3-Pyridyl li-C 3
H
7 9571 OH 4-Pyridyl IH 000/4470~ No. R 3 R4R 952 OH 4-Pyridy. CH 3 953 OH 4-Pyridy. C 2
H
954 OH 4-Pyridyl n-C 3
H
7 955 OH 4-Pyridy. i-C 3
H
7 956 OH 2-Pyrinidy. H 957 OH 2-Pyrimidy. CH 3 958 OH 2-Pyrimidyl C 2
H
959 OH 2-Pyrimidyl n-C 3
H
7 960 OH 2-Pyrimidy.-CH 961 POH 4-Pyrimidyl H 962 OH 4-Pyrimidy. CH 3 963 OH 4-Pyriinidyl C 2
H
964 OH 4-Pyrimidyl n-C 3
H,
7 965 OH 4-Pyrimidyl i-C 3
H
7 966 OH 5-Pyrimidyl H 967 OH 5-Pyriinidyl CH 3 968 OH 5-Pyrimidyl C 2
H
969 OH 5-Pyrimidy. n-C 3
H
7 970 OH 5-Pyrimidyl i-C 3
H
7 971 OH 1,3,5-Triaziny. H 972 OH 1,3,5-Triaziny. CH 3 973 OH 1,3,5-Triazinyl C 2
H
974 OH 1,3,5-Triazinyl n-C3H 7 975 OH 1,3,5-Triazinyl i-C 3
H
7 976 OH 2-Furyl H 977 OH 2-Furyl CH 3 978 OH 2-Furyl C 2
H
979 OH 2-Furyl n-C 3
H
7 980 OH 2-Furyl iCH 981 OH 3-Furyl H 982 OH 3-Furyl CH 3 983 OH 3-Furyl C 2
HS
984 OH 3-Furyl n-C 3
H
7 985 OH 3-Furyl i-C 3
H
7 986 OH 2-Thienyl H 987 IOH 2-Thienyl CH 3 988 OH 2-Thieny. C 2
H
989 OH i2-Thienyl n-C 3
H
7 No. R 3 R4R 990 OH 2-Thienyl i-C 3
H
7 991 OH 3-Thienyl H 992 OH 3-Thieny. CH 3 993 OH 3-Thieny. C 2
HS
994 OH 3-Thienyl n-C 3
H
7 995 OH 3-Thieny. i-C 3
H
7 996 OH 2-Oxazoly. H 997 OH 2-Oxazoly. CH 3 998 OH 2-Oxazoly. C 2
H
999 OH 2-Oxazoly. n-C 3
H
7 1000 OH 2-Oxazolyl -CH 1001 OH 4-Oxazolyl H 1002 OH 4-Oxazoly.. CH 3 1003 OH 4-Oxazoly. C 2
H
1004 OH 4-Oxazolyl n-C 3
H
7 1005 OH 2-Thiazoly. i-C 3
H
7 1006 OH 2-Thiazolyl H 1007 OH 2-Thiazolyl CH 3 1008 OH 2-Thiazolyl C 2
H
1009 OH 2-Thiazolyl n-C 3
H
7 1010 OH 2-Thiazoly. i-C 3
H
7 1011 OH 4-Thiazoly. H 1012 OH 4-Thiazolyl CH 3 1013 OH 4-Thiazolyl C 2
H
1014 OH 4-Isoxazolyl n-C3H 7 1015 OH 4-Isoxazolyl i-C 3
H
7 1016 OH 3-Isoxazolyl H 1017 OH 3-Isoxazolyl CH 3 1018 OH 3-Isoxazolyl C 2
H
1019 OH 3-Isoxazoly. n-C 3
H
7 1020 OH 3-Isoxazoly. i-C 3
H
7 1021 OH 5-Isoxazolyl H 1022 OH 5-Isoxazolyl CH 3 1023 OH 5-Isoxazolyl C 2
H
1024 1OH 5-Isoxazoly. n-C 3
H
7 1025 OH 5-Isoxazolyl iCH 1026 OH 2-Imidazoly. H 1027 OH 2-Imidazolyl CH 3 0000/44M$ No. R 3 4R 1028 OH 2-Imidazolyl C 2
H
1029 OH 2-Imidazolyl n-C 3
H
7 1030 OH 2-Imidazoly.-CH 1031 OH 3-Pyrazolyl H 1032 OH 3-Pyrazoly. CH 3 1033 OH 3-Pyrazolyl C 2
H
1034 OH 3-Pyrazoly. n-C 3
H
7 1035 OH 3-Pyrazoly. i-C 3
H
7 1036 OH 4-Pyrazoly. H 1037 OH 4-Pyrazolyl CH 3 1038 OH 4-Pyrazoly C 2
H
1039 OH 4-Pyrazolyl n-C 3
H
7 1040 4-Pyrazolyl i-C 3
H
7 104 Hi H H 104',I R H CH 3 1043 YHC 2
H
1044 H H n-C 3
H
7 1045 H H i-C 3
H
7 1046 H OH H 1047 H OH CH 3 1048 H OH C 2
H
1049 H OH nl-C 3
H
7 1050 H OH i-C 3
H
7 1051 H cl n-C 4
H
9 1052 H Cl CH 3 1053 H Cl C 2
HS
1054 H Cl n-C 3
H
7 1055 H Cl i-C 3
H
7 1056 H OCH 3
H
1057 H OCH-3 CH 3 1058 H OCH 3
C
2
H
1059 H OCH 3 n-C 3
H
7 1060 H OCH 3 i-C 3
H
7 1061 H CH 3
H
1062 H CH 3
CH
3 1063 H CH 3
C
2
H
1064 H OH 3 n-C 3
H
7 1065 IH CH 3 x-j-C 3
H
7 0060/445rI0 No. R 3 R4S 1066 H Cyclopropyl H 1067 H Cyclopropy. CH 3 1068 H Cyclopropyl C 2
HS
1069 H Cyclopropyl n-C 3
H
7 1070 H Cyclopropyl iCH 1071 Cl H H 1072 Cl H CH 3 1073 Cl H C 2
H
1074 Cl H n-C 3
H
7 1075 Cl H i-C 3
H
7 1076 Cl OH H 1077 Cl OH CU 3 1078 Cl OH C 2
H
1079 Cl OH n-C 3
H
7 1080 Cl OH i-C 3
H
7 1081 Cl Cl n-C 4
H
9 1082 Cl Cl CH 3 1083 Cl Cl C 2
H
1084 Cl CJ. n-C 3
H
7 1085 Cl Cl i-C 3
H
7 1086 Cl OCH 3
H
1087 Cl OCH 3
CU
3 1088 Cl OCH 3
C
2
HS
1089 Cl OCH 3 n-C 3
H
7 1090 Cl OCH 3 i-C 3
H
7 1091 Cl CU 3
H
1092 Cl CU 3
CH
3 1093 Cl CU 3
C
2
HS
1094 Cl CU 3 n-C 3
H
7 1095 Cl CU 3 i-C 3
H
7 1096 Cl Cyclopropyl H 1097 Cl Cyclopropyl CU 3 1098 Cl Cyclopropyl C 2
H.
1099 Cl Cyclopropyl n-C 3
H
7 1100 Cl Cyclopropyl i-C 3
H
7 1101 SCU 3 H H 1102 SCH 3 H CU 3 1103 SCH 3 H C 2
H
0090/44910! No. R 3 R4R 1104 SCH 3 H n-C 3
H
7 1105 SCH 3 H i-C 3
H
7 1106 SCH 3 OH
H
1107 SCH 3 OH CH 3 1108 SCH 3 OH
C
2
H.
1109 SCH 3 OH n-C 3
H
7 1110 SCH 3 OH i-C 3
H
7 1111 SCH 3
CH
3
H
1112 SCH 3
CH
3
H
1113 SCH 3
CH
3
CH
1114 SCH 3
CH
3 nCH 1115 SCH 3
CH
3 -37 1116 SCM 3
SCH
3 1117 SCM 3
SCM
3
CH
3 1118 SCM 3
SCH
3
C
2
H
1119 SCH 3
SCH
3 n-C 3 H7 1120 SCH 3
SCH
3 i-C 3
H
7 1121 SCM 3 CyclopropyJ.
H
1122 1SCH1 3 Cyclopropy- CM 3 1123 SCM 3 Cyclopropyl
C
2
HS
1124 SCM 3 Cyclopropy. n-C 3
H
7 1125 SCM 3 Cyclopropyl i-C 3
H
7 1126 Cyclo- H
H
propyl 1127 Cyclo- H CH 3 propy.
1128 Cyclo- H
C
2
H
5 g propyl 1129 Cyclo- H n-C 3
H
7 propyl 1130 Cyclo- H i-C 3
H
7 propyl. 1131 Cyclo- OH
H
propy.
1132 Cyc2.o- OH
CH
3 propyl 1133 Cyclo- OH
C
2
H
5 g propy. 1134 Cyclo- OH n-C 3
H
7 propyl I 4'r 0060/44575 No. 3R
R
1135 Cyclo- OH i-C 3
H
7 propyl 1136 Cycl o- Cl n-C 4 Hq propyl 1137 Cyclo- Cl CF! 3 propyl 1138 Cyclo- Cl
C
2
H
propyl 1139 Cyclo- Cl n-C 3
H
7 propyl 1140 Cyclo- Cl a.-C 3
H
7 ___propyl 1141 Cyclo- OCH 3
H
propyl 1142 Cyclo- OCH 3
H
propyl 114!3 Cyclo- OCH 3
CH
propy. 1144 Cyclo- OCH 3 nCH propyl 1145 Cyclo- OCH 3 iCH propyl 1146 Cyclo- SCH 3
H
1147 Cyclo- SCH 3
CH
3 propy.
1148 Cyclo- SCH 3
C
2
H
1149 Cyclo- SCH 3 n-C 3
H
7 propyl 1150 Cyclo- SCH 3 i-C 3
H
7 propy.
1151 Cyclo- CH 3
H
1152 Cyclo- CF! 3
CH
3 propyl 1153 Cyclo- CH 3
C
2
H
propyl 1154 Cyclo- CH 3 n-C 3
H
7 propyl 1155 Cyclo.- CH 3 i-C 3
H
7 propyl 1156 CF! 3 2-F-C 6
H
4
H
1157 1CH 3 2-F-C 6
H
4
CH
3 115 BCH 3 2F-C 6
H
4
C
2
H
5 j 000O/40~70 1159 CH 3 2-F-C 6
H
4 nCH 1160 CH 3 2-F-C 6
H
4 i-C 3
H
7 1161 CH 3 2.-F-C 6 11 4 n-C 4
U
9 r 1 16 CU 3 2-F-C 6
H
4 tCH 1 6~ 3
CH
3 2-F-C 6
H
4 nl-C6H13 1164 CU 3 2-F-C 6
H
4 Prop-l-en-3-yl 1165 CU 3 2-F--C 6
H
4 (E)-1-Chloroprop-1-efl- 3 -yl 1166 CU 3 2-F-C 6
H
4 Propyn-3-yl 1167 CU 3 2-F-C 6
H
4 3-Methyl-but-2-el-y 1168 CU 3 3-F-C 6
H
4
H
1169 CU 3 3-F-CGU 4
CU
3 1170 CH 3 3-F-C 6
H
4
C
2
U
1171 CH 3 3-F-C 6
H
4 n-C 3
H
7 1172 CU 3 3-F-C 6
H
4
ICH
1173 CU 3 3-F-C 6
H
4 n-C 4 H9 1174 CH 3 3-F-C 6
H
4 t-C 4 H9 1175 CU 3 3-F-C 6
U
4 n-C 6
H
1 3 1176 CU 3 3-F-CGH 4 Prop-l-en-3-y 1177 1CU 3 3-F-C 6
H
4 (E)-1-Chloroprop-l-efl-3-yl 1178 CU 3 3-F-C 6
H
4 Propyn-3-yl 1179 CU 3 3-F-C 6
H
4 3-Methyl-but-2-el-1-yJ 1180 CU 3 4-F-C 6
H
4
H
1181 CU 3 4-F-C 6
H
4
CU
3 1182 CU 3 4-F-C 6
H
4
C
2
U
1183 CU 3 4-F-C 6
U
4 n-C 3
H
7 1184 CU 3 4-F-C 6
H
4
'CH
1185 CU 3 4-F-C 6
H
4 rI-C 4
H
9 1186 CU 3 4-F-C 6
H
4 t-C 4
H
9 1187 CU 3 4-F-C 6
U
4 n-C 6 Hl 3 1188 CU 3 4-F-C 6
H
4 Prop-1-en-3-yl 1189 CU 3 4-F-C 6
H
4 (E)-1-Chloroprop---efl-3-y- 1190 CU 3 4-F-C 6
U
4 Propyn-3-y3.
1191 CU 3 4-F-C 6
H
4 3-Methyl-but-2-el-1-y- 1192 CU 3 2-Cl-C 6
H
4
U
1193 CU 3 2-Cl-C 6
U
4
CU
3 1194 CU 3 4-CI-C6H 4 CqUs 1195 CU 3 2-Cl-C 6 U4 n-C 3
H
7 1196 CU 3 2-G-H 4 i-C 3
H
7 000~0 /44071 No.
1197 1198 1199 1200 1201 1202 1203 1204 1205 1206 1207 1208 1209 1210 1211 1212 1213 1214 1215 1216 1217 1218 1219 1220 1221 1222 1223 1224 1225 1226 1227 1228 1229 1230 1231 1232 1233 1234
C
3
CH
3
C
3
CH
3
CH
3
CE
3
CE
3
CE
3
C
3
CE
3
CE
3
CH
3
CE
3
CE
3
CE
3
CH
3
CE
3
CE
3
CH
3
CE
3
CE
3
CH
3
CE
3
CE
3
CE
3
CE
3
CE
3
CE
3
CE
3
CE
3
CE
3
CH
3
CE
3
CE
3
CE
3
CE
3
CH
3
CE
3 2-Cl-C 6 fE 4 2-Cl-C 6
H
4 2-Cl-C 6
H
4 2-Cl-C 6
H
4 2-cl-C 6
H
4 3-Cl-C 6
E
4 3-C1-C 6
H
4 3-Cl-C 6
H
4 3-Cl-C 6
H
4 3 -Cl-C 6
E
4 3-Cl-C 6
E
4 3-Cl-C 6
H
4 3 -Cl-C 6
E
4 3-Cl-C 6
H
4 3-Cl-C 6
H
4 3-Cl-C 6
H
4 3-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4 -Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 4-Cl-C 6
H
4 2, -C-C 6
E
3 2, -C-C E 3 2, 3-C1 2
-C
6
E
3 2, 3-C1 2
-C
6
E
3 2, 3-C1 2
-C
6
H
3 2, 3-Cl 2
-C
6 H3 2, 3-C1 2
-C
6
E
3 1R n-C 4
H
9 t-C 4
H
9 n-C 6 Hl 3 Prop--en-3-yl -1-Chloroprop-l-Cfl- 3 -yl Fropyn- 3-yl 3-Methyl-but- 2-.-an 1 -yl
H
CE
3
C
2
H
n-C 3
H
7 i-C 3
E
7 n-C 4 H9 t-C 4
H
9 n-C 6
HI
3 Prop-i-en- 3-yl -1-Chloroprop-1-en- 3 -yl Propyn- 3-yl n-C 3
H
7 i-C 3
H
7 n-C 4 H9 t-C 4
H
9 n-C 6 Hl 3 Prop-1-en-3-yl -1-Chloroprop-1-en- 3 -yl Propyn-3-yl
H
CH
3
C
2
HS
n-C 3
H
7 3.-C 3
H
7 n-C 4 H9 t-C 4 Hg 005/144 5 I No. R 4R 1235 CH 3 2, 3-C1 2
-C
6
H
3 n-CrHI3 1236 CH 3 2,3-C 2
-C
6 H3 Frop-l-en-3-yl 1237 CH 3 2,3-Cl 2
-C
6
H
3 (E).-1-Chloroprop-1-e1-" 3 -yl 1238 CH 3 2,3-Cl 2
-C
6
H
3 Propyfl- 3 yl 1239 CH 3 2,3-Cl 2
-C
6
H
3 3-Methyl-but-2-efl-1-yl 1240 CH 3 2,4-Cl 2
-C
6
H
3
H
1241 CH 3 2,4-Cl 2
-C
6
H
3
CH
3 1242 CH 3 2,4-Cl 2
-C
6
H
3
C
2
HS
1243 CH 3 2,4-Cl 2
-C
6
H
3 n-C 3
H
7 1244 CH 3 2,4-Cl 2
-C
6
H
3 i-C 3
H
7 1245 CH 3 2,4-Cl 2
-C
6
H
3 n-C 4 H9 1246 CE 3 2,4-Cl 2
-C
6 1 3 t-C 4 H9 1247 CH 3 2,4-Cl 2
-C
6
H
3 n-C 6 Hl 3 1248 CH2. 2,4-Cl 2
-C
6
H
3 Prop-l-en-3-y).
1249 CH 3 2, 4-Cl 2
-C
6
H
3 -1-Chloroprop-1-efl- 3 -yl 1250 2, 4-Cl 2
-C
6
H
3 1251 3 2,1 2
-C
6
H
3
I
1252 2, 5-Cl 2
-C
6
H
3 125is3 1254 1255 2, 5-Cl 2
-C
6
E
3 2, 5-C1 2
-C
6
H
3 CE 3 I CH3 2, 5-Cl 2
-C
6
H
3 -l 1256 CH 3 2, 5-C1 2
-C
6
H
3 125 CH -C 2
CE
1258 CE 3 2,5-C1 2
-C
6
H
3 1259 CE 3 2,5-Cl 2
-C
6
H
3 1260 CE 3 2 5-Cl 2
-C
6
H
3 1261 CE 3 2,5-Cl 2
-C
6
H
3 1262 CH 3 2, 5-Cl 2
-C
6
H
3 1263 CE 3 2, 5-Cl 2
-C
6
H
3 1264 CE 3 2,6-Cl 2
-C
6
H
3 1265 CH 3 2, 6-Cl 2
-C
6
H
3
H
CH
3
C
2
HS
n-C 3
H
7
-C
3
H
7 n-C 4 H9 t-C 4
H
9 n-C 6
HI
3 Prop-1-en-3-yJ.
(E -1Chloroprop-l-el- 3 -yl Propyn-3-y.
3-Methyl-but-2-el- 1-y 2
H
CE
3
C
2
H
n-C 3
H
7 n-C 4 H19 t-C 4 H9 1266 2, 6-C1 2
-C
6
H
3 1267 CH 3 2,6-Cl 2
-C
6
H
3 1268 CH 3 2,6-Cl 2
-C
6
H
3 1269 CH 3 2,6.-Cl2-C6H3
I
1270 2, 6-C1 2
-C
6
H
3 1 4 1 1271 1272
CE
3
CH
3 2, 6-C1 2
-C
6
H
3 2, 6-Cl 2
-C
6
H
3
I
n-CGH 1 3 ir-op-l-en- 3 -y- 000/4079~ No. R 4R 1273 CU 3 2,6-Cl 2 -C6H3 (E)->-Chloroprop-1-el-3-yJ.
1274 CH 3 2, 6-C12-C6H3 Propyn-3".yl 1275 CU 3 2, 6-C1 2
-C
6 H3 3-MthyJ-but-2-Ofl-1-y2 1276 CU 3 3,4-Cl 2
-CGH
3 Hi 1277 CU 3 3, 4-C1 2
-COU
3
CH
3 1278 CU 3 3, 4-C1 2
-C
6
H
3
C
2
H
1279 CU 3 3,4-C1 2
-C
6
H
3 n-C 3
H
7 1280 CU 3 3,4-Cl 2
-C
6
H
3 i-C 3
H
7 1281 CH 3 3, 4-Cl 2 -Cr-U 3 n-C 4 Ug 1282 Cl- 3 3,4-Cl 2
-C
6
H
3 t-C 4 Hq 1283 CU 3 3,4-Cl 2
-C
6
H
3 n-C 6
H
1 3 1284 CU 3 3, 4-Cl 2
-C
6
U
3 Prop-1--en--3-yl 1285 CH 3 3, 4-CJ- 2
-C
6
H
3 (E)-1--Chloroprop-1-Gfl-3-yl 1286 CU 3 3,4-Cl 2
-C
6
H
3 Propyn-3-yl 1287 CU 3 3, 4-Cl 2
-C
6
H
3 3-Methyl-but-2-efl-1-yJ.
1288 CH 3 3,5-Cl 2
-C
6
H
3 lH 1289 CH 3 3,5-C 2
-C
6
H
3
CU
3 1290 CU 3 3,5-Cl 2
-C&H
3
C
2
H
1291 CU 3 3, 5-Cl2-C 6
H
3 n-C 3
H
7 1292 CU 3 3,5-Cl 2
-C
6
H
3 i-C 3
H
7 1293 CU 3 3,5-Cl 2
-C
6
H
3 n-C 4
H
9 1294 CU 3 3,5-Cl 2
-C
6
U
3 t-C 4 H9 1295 CU 3 3,5-C1 2
-C
6
H
3 n-C 6
H
1 3 1296 CU 3 3,5-Cl 2
-C
6
H
3 Prop-1-en-3-yJ.
1297 CU 3 3,5-Cl 2
-C
6
H
3 (E)-1-Chloroprop--el-3-yJ- 1298 CU 3 3,5-CJ.
2
-C
6
H
3 Propyn-3-y.
1299 CU 3 3,5-CI 2
-C
6
H
3 3-Methyl-but-2-el-1-y).
1300 CU 3 2-Br-C 6
U
4
U
1301 CU 3 2-Br-C 6
H
4
CU
3 1302 CU 3 2-Br-C 6
U
4
C
2
H
1303 CU 3 2-flr-C 6
H
4 n-C 3
H
7 1304 CU 3 2-Br-C 6
U
4 i-C 3
H
7 1305 CU 3 2-Br-C 6
H
4 n-C 4 H9 1306 CU 3 2-Br-C 6
H
4 t-C 4 Ug 1307 CU 3 2-Br-C 6
U
4 n-C 6
H
13 1308 CU 3 2-Br-C 6
H
4 Prop-1-ei-3-y.
1309 CU 3 2-Br-C 6
H
4 i(E)-1-Chloroprop-1-el- 3 1310 ICU 3 2-Br-C 6
U
4 Prpn3-y.
005!~0 /44675 1311 CU 3 2-43r-C 6
H
4 3-Methyl-but-2-efl-1-Y1 51312 CH 3 3-Br-CGU 4
H
1313 CH 3 3-Br-C 6
U
4
CH
3 1314 CH 3 3-flr-C 6
U
4
C
2
HS
1315 CU 3 3-Br-C 6
H
4
-CH
1316 CU 3 3-Br-C 6
H
4 i-C 3
H
7 137C 3 3B-CU iC11 1318 CH 3 3-Br-C 6
H
4 n-C 4
H
9 1319 CU 3 3-Br-C 6
H-
4 n-C 6
U
1 3 1320 CH 3 3-Br-C 6
H
4 Prop-1-en-3-yl 1321 CU 3 3-Br-C 6
U
4 (E)-i-Chloroprop---e-3-y 3 1322 CH 3 3-Br-C 6
U
4 P;rcpyn-3-yl 1323 CU 3 3-Br-C 6
UI
4 3-Methyl-but-2-el-1--yl 1324 CU 3 4-Br-C 6
U
4
H
1325 CH 3 4-Br-C 6
U
4
CUH
3 1326 CU 3 4-Br-C 6
H
4
C
2
H
1327 CU 3 4-Br-C 6
H
4 n-C 3
U
7 1328 CU 3 4-Br-C 6
H
4 i-C 3
H
7 251329
CU
3 4-Br-C 6
H
4 n-C 4 H9 1330 CU 3 4-Br-C 6
H
4 t-C 4
H
9 1331 CU 3 4-Br-C 6
H
4 n-C 6
H
1 3 1332 CU 3 4-Br-C 6
H
4 Prop-1-en-3-yl 1333 CU 3 4.-Br-C 6
H
4 (E)-l-Chloroprop-1-efl- 3 -yl 1334 CU 3 4-Br-C 6
H
4 Propyn-3-yl 1335 CU 3 4-Br-C 6
U
4 3-Methyl-but-2-efl-1-yJ.
1336 CU 3 2-I-C 6
U
4
U
1337 CU 3 2-I-C 6
H
4
CU
3 1338 CU 3 2-I-C 6
U
4
C
2
,H
1339 CU 3 2-I-C 6
U
4 n-C 3
H
7 1340 CU 3 2-I-C 6
H
4 i-C 3
H
7 1341 CU 3 2-I-C 6
U
4 n-C 4 H9 40"342 CU 3 2-1-C 6
H
4 t-C 4 H9 1343 CU 3 2-I-C 6
U
4 n-CGH 1 3 1344 CU 3 2-I-C 6
H
4 Prop-.1-en-3-'yl 1345 CU 3 2-I-C 6
H
4 (E)-l-Chloroprop-l-Qfl- 3 -yl 1346 CU 3 2-I-C 6
U
4 Propyn-3-yl 451347 CU 3 2-I-C 6
H
4 3-Methyl-but-2-e-1 -yl T1348 CU 3 3XCU 41) 00 610 /449~7 No'. R 1.349 CU 3 3-X-C 6
U
4
CH
3 1350 CH3 3-1-CG1 4 -1C 2 1-1 1351 CH 3 3-I-CF1 4 n-C 3
H
7 1352 CH3 3-1-CGU 4 C 17 1353 CU 3 3--CU 4 t-C 4 H9 1354 CU 3 3--64t-C 4
H
9 1355 CU 3 3-I--C 6
H
4 n-C 6
H
1 3 1356 CH 3 3-.t-C 6
H
4 Prop-1-en--3-yl 1357 CU 3 3-1-C 6
H
4 (E)-.1-Chloroprop-1-efl-3-yl 1358 CH 3 3-I-C 6
H
4 Propyn-3-y3.
1359 CU 3 3-I-CC;U 4 3-Methyl-but-2-efl--yl 1360 CU 3 4-1-CSU 4
H
1361 CU 3 4-I-C 6
H
4
CU
3 1362 CH 3 4-I-C 6
H
4
C
2
H
1363 CU, 3 4-I-C 6
H
4 n-C 3
H
7 1364 CH 3 4-I-C 6
H
4 i-C 3
H
7 1365 CH 3 4-I-CGU 4 n-C 4 H9 1366 CU 3 4-I-C 6
H
4 t-C 4 H9 1367 CU 3 4-I-C 6
U
4 n-C 6
H
1 3 1368 CU 3 4-I-CUH 4 Prop-1-eiv-3-yl 1369 CU 3 4-I-C 6
U
4 (E)-1-ChJloroprop-1-el-3-y- 1370 CU 3 4-I-C 6
H
4 Propyn-3-y.
1371 CU 3 4-I-C 6
H
4 3-Methyl-.but-2-en-1-yl 1372 CU 3 2-CN-C 6
U
4
U
1373 CU 3 2-CN-C 6
U
4
CU
3 1374 CU 3 2-CN-C 6
H
4
C
2
H
1375 CU 3 2-CN-C 6
U
4 n-C 3
H
7 1376 CU 3 2-CN-C 6
U
4 i-C 3
H
7 1377 CU 3 2-CN-C 6
U
4 n-C 4
H
9 1378 CU 3 2-CN-C 6
H
4 t-C 4
H
9 1379 CU 3 2-CN-C 6
H
4 n-C 6
U
1 3 1380 CH 3 2-CN-C 6
H
4 Prop-1-en-3-yl 1381 CU 3 2-CN-C 6
U
4 (E)-l-Chloroprop-1-efl-3-yl "382 CU 3 2-CN-C 6
H
4 Propyri-3-yJ.
1383 CU 3 2-CN-C 6 11 4 3-Methyl-but-2-efl-1-yl 1384 ICU 3 3-CN-C 6
H
4
U
1385 CU 3 3-CN-C 6
U
4
CU
3 1386 CU 3 3-CN-C 6
H
4
IC
2
U
0000/446V70 No. R 3 R R 1387 CH 3 3-CN-C6H 4 ri-C 3
H
7 1388 CH 3 3-CN-C 6
H
4 i-C 3
H
7 1389 CH 3 3-CN-C 6
H
4 n-C 4
H
9 1390 CH 3 3-CN-C 6
H
4 t-C 4
H
9 13 1§1 CH 3 3-CN-C 6
H
4 n-C 6
HI
3 1392 CH 3 3-CN-C 6
H
4 Prop-1-en-3-y- 1393 CH 3 3-CN-C 6
H
4 (E)-.1-Chloroprop-1--efl-3-yl 1394 CH 3 3-CN-C 6
H
4 Propyn-3-y.
1395 CH 3 3-CN-C 6
H
4 3.-Methyl-but-2-efl-1-yl 1396 CH 3 4-CN-C 6
H
4
H
1397 CH 3 4-CN-C 6
H
4
CH
3 1398 CH 3 4-CN-C 6
H
4
C
2
HS
1399 CH 3 4-CN-C 6
H
4 n-C 3
H
7 .1400 1CR 3 4-CN--C 6
H
4 i-C 3
H
7 1401 ICR 3 4-CN-C 6
H
4 n-C 4
H
9 1402 CR 3 4-CN-C 6
H
4 t-C 4 H9 1403 CH 3 4-CN-C 6
H
4 n-C 6
H
1 3 1404 CR 3 4-CN-C 6
H
4 Prop-.-en-3-yl 1405 CH 3 4-CN-C 6
H
4 (E)-l-Chloroprop-1-el-3-yl 1406 CR 3 4-CN-C 6
H
4 Propyn-3-yl 1407 CH 3 4-CN-C 6
H
4 3-Methyl-but-2--en-1-yl 1408 CH 3 2-N0 2 -Cr-H 4
H
1409 CH 3 2-N0 2
-CGH
4
CH
3 1410 CH 3 2-N0 2
-C
6
H
4
C
2
HS
1411 CH 3 2-N0 2
-C
6
H
4 n-C 3
H
7 1412 CR 3 2-N0 2
-C
6
H
4 i-C 3
H
7 1413 CH3 2-N0 2
-C
6
H
4 n-C 4
H
9 1414 CH 3 2-N0 2
-C
6
H
4 t-C 4 H9 ,1415 CR 3 2-N0 2
-C
6
H
4 n-C 6
H
1 3 1416 CH 3 2-N0 2
-C
6
H
4 Prop-1-eni-3--yl 1417 CR 3 2-N0 2
-C
6
H
4 (E)-.1-Chloroprop-1-efl-3-yl 1418 CH 3 2-N0 2
-C
6
H
4 Propyn-3-y.
1419 CH 3 2-N0 2
-C
6
H
4 3-Methyl-but-2-en-1-yl 1420 CH 3 3-N0 2
-C
6
H
4
H
1421 CH 3 3-NO 2
-C
6
H
4
CRH
3 1422 CH 3 3-N0 2
-C
6
H
4
C
2
HS
1423 CH 3 3-NO 2 -C6H 4 n-C 3
H
7 1424 CH 3 3-N0 2
-C
6
H
4 li-C 3
H
7 0050/44070 ~No. R3 4R 1425 CU 3 3-N0 2
-C
6
H
4 n-C 4 Hi 9 1426 CU 3 3-N0 2
-C
6
H
4 t-C 4
H
9 1427 CU 3 3-N0 2
-C
6
H
4 n-C 6
HI
3 1428 CU 3 3-N0 2
-C
6
H
4 Prop-1-en-3-yJ.
1429 CH 3 3-N0 2
-C
6
H
4 (E)-1--Chloroprop-1-Gfl-3-yl 1430 CH 3 3-N0 2
-C
6
H
4 1431 CH 3 3-N0 2
-C
6
H
4 3-Methyl-but-2-en-1-yl 1432 CH 3 4-N0 2
-C
6
H
4
H
1433 CH 3 4-N0 2
-C
6
U,
4
ICH
3 1434 CU 3 4-N0 2
-C
6
H
4
C
2
H
1435 CH 3 4-N0 2
-C
6
H
4 n-C 3
H
7 1436 CU 3 4-N0 2
-C
6
H
4 i-C 3
H
7 1437 CU 3 4-N0 2
-C
6
H
4 n-C 4 H9 1438 CU 3 4-N0 2
-C
6
H
4 t-C 4 H9 1439 CU 3 4-N0 2
-C
6
H
4 n-C 6 Hl 3 1440 CU 3 4-N0 2
-C
6
H
4 Prop-1-en-3-yl 1441 CU 3 4-N0 2
-C
6
H
4 (E)-1-Chloroprop-1-efl-3-yl 1442 CU 3 4.-N0 2
-CGH
4 Propyn-3-yl 1443 CU 3 4-N0 2
-C
6
H
4 3-Methyil-but-2-en-1-yl 1444 CU 3 2-CH 3
-C
6
H
4
U
1445 'CU 3 2-CH 3
-C
6
U
4
CU
3 1446 CU 3 2-CH 3
-C
6
U
4
C
2 HS 1447 CU 3 2-CH 3
-C
6
U
4 n-C 3
H
7 1448 CU 3 2-CH 3
-C
6
H
4 iCH 1449 CU 3 2-CH 3
-C
6
H
4 n-C 4 H9 1450 CU 3 2-CH 3
-C
6
H
4 t-C 4 H9 1451 CU 3 2-CH 3
-C
6
H
4 n-C 6
H
13 1452 ,CU 3 2-CH 3
-C
6
U
4 Prop-l-en-3-yJ.
1453- CU 3 2-CH 3
-C
6
H
4 (E)-1-Chioroprop--el-3-yl 1454 CU 3 2-CH 3
-C
6
H
4 Propyn-3--yl 1455 CU 3 2-CH 3
-C
6
H
4 3-Methyl--but-2-en-1-yl 1456 CU 3 3-CH 3
-C
6
H
4
H
1457 CU 3 3.-CH 3
-C
6
H
4
CU
3 1458 CU 3 3-CH 3
-C
6
H
4
C
2
U
1459 CU 3 3-CH 3
-C
6
H
4 n-C 3
H
7 1460 CU 3 3-CH 3
-C
6
H
4 iCH 1461 CU 3 3-CH 3
-C
6
H
4 n-C 4
H
9 1462 CU 3 .3-CH 3
-C
6
H
4 t-C 4
U
9 0000/44070 No. 3R
R
1463 CU 3 3-CH 3
-CGH
4 fl-C6H1 3 1464 CU 3 3-CU 3
-C
6
H
4 Prop-1-en-3-yl 1465 CU 3 3-CH 3
-C
6
H
4 (E)-l-ChJloroprop-l-el-3-yl 1466 CH 3 3-CH 3 -C6H4 Propyn-3--yl 1467 CU 3 3-CH 3
-CGH
4 3-Methyl-but-2-efl-1-yl 1468 CU 3 4-C11 3
-C
6
H
4
H
1469 CH 3 4-CH 3
-C
6
H
4
CU
3 1470 CU 3 4-CH 3
-C
6
H
4
C
2
U
1471 CU 3 4-CH 3
-C
6
H
4 n-C 3
H
7 1472 CU 3 4-CH 3
-C
6
H
4
'-C
3
H
7 1473 CU 3 4-CH 3 -C I rn-C 4 H9 1474 CU 3 4-CH 3
-CGH
4 t-C 4
H
9 1475 CU 3 4-CH 3
-C
6
H
4 n-C 6
H
1 3 1476 CU 3 4-CU 3
-C
6
H
4 Prop-1-en-3-yJ.
1477 CU 3 4-CH 3
-C
6
H
4 (E)-1-Chloroprop-1-en-3-yl 1478 CU 3 4-CH 3
-C
6
H
4 Propyn-3-yl 1479 CU 3 4-CH 3
-C
6
H
4 3-Methyl-but-2-el-1-yJ.
1480 CU 3 2,3.-(CU 3 2
-C
6
U
3
H
1481 CH 3 2, 3- (CU 3 2
-C
6
H
3
CU
3 1482 CU3 2,3-(C 3 2
-C
6
U
3
C
2
H
1483 CU 3 2,3-(CH 3 2
-C
6
H
3 n-C 3
U
7 1484 CU 3 2, 3- (CH 3 2
-C
6
U
3 i-C 3
U
7 1485 CU 3 2,3-(CH 3 2
-C
6
U
3 n-C 4 Ug 1486 CU 3 2,3-(CH 3 2
-C
6
H
3 t-C 4 H9 1487 CU 3 2,3-(CU 3 2
-C
6
H
3 n-C6H 1 3 1488 CU 3 2, 3- (CH 3 2
-C
6
U
3 Prop-1-en-3-yl 1489 CU 3 2,3-(CU 3 2
-C
6
H
3 (E)-1-Chloroprop-1-el-3-yl 1490 CU 3 2,3-(CH 3 2
-C
6
U
3 Propyn-3-y.
1491 CH 3 2,3-(CH 3 2
-C
6
H
3 3-Methyl-but-2-efl-yl 1492 CU 3 2,4-(CU 3 2
-C
6
H
3
U
1493 CU 3 2,4-(CH 3 2
-C
6
H
3
CU
3 1494 CU 3 2, 4- (CH 3 2
-C
6
U
3
C
2
H
1495 CU 3 2,4-(CH 3 2
-C
6
U
3 n-C 3
H
7 1496 CU 3 2, 4- (CH 3 2
-C
6
H
3 i-C 3
H
7 1497 CU 3
CU
3 2
-C
6
U
3 n-C 4 H9 1498 CU 3 2,4-(CH 3 2
-C
6
H
3 t-C 4
U
9 1499 CU 3 2,4-(CH 3 2
-C
6 H3 n-C 6
H
1 3 1500 ICU 3 2,4-(CU 3 2
-C
6
H
3 Prop-1-en-3-yl No. R 4R 1501 CB 3 2,4-(CH 3 2
-C
6
H
3 (E)-1-Chloroprop--el-3-y.
1502 CB 3 2, 4- (CH 3 2 -C6B 3 Propyn-3-yl 1503 CB 3 2,4-(GB 3 2
-C
6
H
3 3-Methyl-but-2-en-1-yl 1504 GB 3 2,5-(CH 3 2
-C
6
H
3
H
1505 GB 3 2,5-(CH 3 2
-C
6
H
3
CH
3 1506 GB 3 2,5-(CB 3 2
-C
6
B
3
C
2
B
1507 GB 3 2,5-(CB 3 2
-C
6
H
3 n-C 3
H
7 1508 GB 3 2, 5- (CE1 3 2
-C
6
H
3 i-C 3
H
7 1509 GB 3 2,5-(CH 3 2
-C
6
H
3 n-C 4 Bg 1510 CB 3 2r5-(CB 3 2
-C
6
H
3 t-C 4 H9 1511 GB 3 2,5-(CB 3 2
-C
6
H
3 n-C 6 Hl 3 1512 GB 3 2,5-(CB 3 2
-C
6
B
3 Prop-1-en-3-yJ.
1513 GB 3 2,5-(C 3 2
-C
6
H
3 (E)-1-Chloroprop-l-efl-3-yl 1514 CH 3 2,5-(CB 3 2
-C
6
B
3 Propyn-3-yJ.
1515 GB 3 2,5-(CH 3 2
-C
6
B
3 3-Methyl-but-2-el-1-y- 1516 CH 3 2,6-(CB 3 2
-C
6
B
3
H
1517 GB 3 2,6-(CB 3 2
-C
6
B
3
CB
3 1518 GB 3 2,6-(GB 3 2
-G
6
B
3
C
2
B
1519 GBH 3 2,6-(GH 3 2
-G
6
B
3 n-G 3
B
7 1520 GB 3 2,6-(CB 3 2
-C
6
B
3 i-C 3
B
7 1521 GB 3 2,6-(CH 3 2
-C
6
B
3 n-C 4
B
9 1522 GB 3 2,6-(CB 3 2
-C
6
B
3 t-C 4
B
9 1523 GB 3 2,6-(CB 3 2
-C
6
B
3 n-G 6
B
1 3 1524 GB 3 2, 6- (G, 3 2
-C
6
H
3 Prop-l-en-3-yl 1525 GB 3 2,6-(CB 3 2
-C
6
B
3 (E)-1-Cliloroprop--1-efl-3-yl 1526 GB 3 2,6-(CB 3 2
-C
6
B
3 Propyn-3-yl 1527 GB 3 2,6-(CB 3 2
-C
6
H
3 3-Methyl-but-2--ef-1-yl 1528 GB 3 3,4-(CB 3 2
-C
6
B
3
B
1529 GB 3 3, 4- (CB 3 2
-C
6 3
GB
3 1530 GB 3 3,4-(CB 3 2
-C
6
H
3
C
2
H
1531 GB 3 3,4-(CH 3 2
-C
6
H
3 n-C 3
B
7 1532 GB 3 3,4-(CB 3 2 6
H
3 i.-C 3
B
7 1533 CB 3 3,4-(CB 3 2
-C
6
B
3 n-C 4 Bg 1534 GB 3 3,4-(CB 3 )2-C 6
B
3 t-C 4 H9 1535 GB 3 3,4-(CB 3 2
-G
6
B
3 n-C 6
B
1 3 1536 GB 3 3,4-(CB 3 2
-C
6
B
3 Prop.-l-en-3-yJ.
1537 GBC 3 3,4-(CH 3 2
-C
6
B
3 (E)-1-=Ghloroprop-1--efl-3-yl 1538GB 3 3,4-(CB 3 2
-C
6
B
3 Propyn-3-y.
0000/44979 No. R 3 R4R 1539 CH3 3, 4-(CUH 2
-C
6
H
3 3-Methyl-but-2-en-1-y! 1540 CH 3 3,5-(CH 3 2
-C
6
H
3
H
1541 CU 3 3,5-(CH 3 2
-C
6
H
3
CU
3 1542 CU 3 3r5-(CH 3 2
-C
6
H
3
C
2
H
1543 CU 3 3,5-(C 3 2
-C
6
H
3 n-C 3
H
7 1544 CU 3 3,5-(C 3 2
-C
6
H
3 i-C 3
H
7 1545 CU 3 3,5-(CH 3 2
-C
6
H
3 n-C 4
H
9 1546 CU 3 3,5-(CH 3 2
-C
6
H
3 t-C 4 H9 1547 CU 3 3,5-(CH 3 2
-C
6
H
3 n-C 6
H
1 3 1548 CU 3 3,5-(CH 3 2
-C
6
H
3 Prop-l-en-3-yl 1549 CU 3 3,5-(CH 3 2
-C
6
H
3 (E)-1-Chloroprop--en-3-yJ 1550 CU 3 3,5-(CH 3 2
-C
6
H
3 Propyn-3-yl 1551 CU 3 3,5-(CH 3 2
-C
6
H
3 3-Methyl-but-2-el-1-y.
1552 CU 3 2-C 2
H
5
-C
6
H
4
U
1553 CU 3 2-C 2
H
5
C
6
H
4
CU
3 1554 CU 3 2-C 2
HS-C
6
H
4
C
2
H
1555 CU 3 2-C 2
H
5
C
6
H
4 n-C 3
H
7 1556 CU 3 2-C 2
HS-C
6
H
4 iCH 1557 CU 3 2-C 2
HU
5
-C
6
H
4 n-C 4 H9 1558 CU 3 2-C 2
H
5
-C
6
H
4 t-C 4 H9 1559 CU 3 2-C 2
H
5
-C
6
H
4 -63 1560 CU 3 2-C 2
H
5
-C
6
U
4 Prop-l-en-3-yl 1561 CU 3 2-C 2
U
5
C
6
H
4 (E)-1-Chloroprop--el-3-y- 1562 CU 3 2-C 2
H
5
-C
6
U
4 Propyn-3-yJ.
1563 CU 3 2-C 2
H
5
-C
6
U
4 3-Methyl-but-2-efl-1-yl 1564 CU 3 3-C 2
H
5
-C
6
H
4
H
1565 CU 3 3-C 2
H
5
-C
6
H
4
CU
3 1566 CU 3 3-C 2
H
5
-C
6
H
4
C
2
HS
1567 CU 3 3-C 2
H
5
-C
6
H
4 n-C 3
H
7 1568 CU 3 3-C 2
HU
5
-C
6
U
4 i-C 3
H
7 1569 CU 3 3-C 2
H
5
-C
6
H
4 n-C 4 H9 1570 CU 3 3-C 2
HS-C
6
H
4 t-C 4
H
9 1571 1CU 3 3-C 2
H
5
-C
6
U
4 n-C 6
H
1 3 1572 CU 3 3-C 2
HU
5
-C
6
H
4 Prop-l-en-3-y2 1573 CU 3 3-C 2
HS-C
6
U
4 (E)-l-Chloroprop--1-efl- 3 -yl 1574 CU 3 3-C 2
U
5
-C
6
H
4 Propyn-3-yl 1575 CU 3 3-C 2
H
5
-C
6
H
4 _3-Methyl-but-2-efl-1-yJ.
1576 CU 3 4C 2
U
5
-CGU
4
U
No. R 3 R R 1577 CH 3 4-C 2
H
5
-C
6
H
4
CU
3 1578 CH 3 4-C 2
HS-C
6
H
4
C
2
H
1579 CU 3 4-C 2
H
5
-C
6
H
4 n-C 3
H
7 1580 CH 3 4-C 2
H
5
-C
6
H
4 i-C 3
H
7 1581 CU 3 4-C 2
H
5
-C
6
H
4 n-C 4 Hq 1582 CU 3 4-C 2
HS-C
6
H
4 t-C 4 H9 1583 CH 3 4-C2H 5
-C
6
H
4 n-C 6
HI
3 1584 CU 3 4-C 2 1i 5
-C
6
U
4 A Prop-l-en-3-yl 1585 CU 3 4-C 2
H
5
-C
6
H
4 (E)-l-Chloroprop--e-3-y 1586 CU 3 4-C 2
HS-C
6
H
4 Propyn-3-yl 1587 CU 3 4-C 2
HS-C
6
H
4 3-Methyl-but-2-en-1-yl 1588 CU 3 2-i-C 3
H?-C
6
H
4
H
1589 CU 3 2-i-C 3
H
7
-C
6
H
4
CU
3 1590 CU 3 2-i-C 3
H
7
-C
6
H
4
C
2
H
1591 CU 3 2-i-C 3
H
7
-C
6
H
4 n-C 3
H
7 1592 CU 3 2.-i-C 3
H
7
-C
6
H
4 i-C 3
U
7 1593 CU 3 2-i-C 3
H
7
-C
6
H
4 n-C 4 Hq 1594 CU 3 2-i-C 3
U
7
-C
6
H
4 t-C 4 H9 1595 CU 3 2-i-C 3
H
7
-C
6
H
4 n-C 6
H
1 3 1596 CU 3 2-i-C 3
H
7
-C
6
H
4 Prop-1--en-3-yJ.
1597 CU 3 2-i-C 3
H
7
-C
6
H
4 (E -lChloroprop-1-Gfl-3-y1 1598 CU 3 2-i-C 3
H
7
-C
6
H
4 Propyn-3-yl 1599 CU 3 2-i-C 3
H
7
-C
6
H
4 3-Methyl-but-2-en-1-yl 1600 CH 3 3-i-C 3
H
7
-C
6
H
4
H
1601 CU 3 3-i-C 3
H
7
-C
6
H
4
CU
3 1602 CU 3 3-i-C 3
H
7
-C
6
H
4
C
2
H
1603 CU 3 3-i-C 3
H
7
-C
6
H
4 n-C 3
H
7 1604 CU 3 3-i-C 3
H
7
-C
6
H
4 i-C 3
H
7 1605 CH 3 3-i-C 3
H
7
-C
6
H
4 n-C 4 Hq 1606 CU 3 3-i-C 3
H
7
-C
6
H
4 t-C 4 H9_ 1607 CU 3 3-i-C 3
H
7
-C
6
H
4 n-C 6
H
1 3 1608 CU 3 3-i-CU 7
-C
6
U
4 Prop-1.-en-3-yl 1609 CU 3 3--i-C 3
H
7
-C
6
H
4 -1-Chloroprop-1-ei-3-y.
1610 CU 3 3-i-C 3
H
7
-CGH
4 Propyn-3--yl 1611 CU 3 3-i-C 3
H
7
-C
6
H
4 3-Methyl-but-2-en-1-y- 1612 CU 3 4-i-C 3
H
7
-CGH
4
U
1613 CU 3 4-i-C 3
U
7
-C
6
H
4
CU
3 1614 CU 3 14-i-C 3
H
7
-C
6
U
4
C
2
HS
000/ 44070 No. R 4R 1615 CU 3 4-i-C 3 H7-CSH 4 n-C 3
H
7 1616 CU 3 4-i-C 3 7 -C11 4 i-C 3
H
7 1617 CH 3 4-i-C 3
H
7
-C
6
H
4 n-C 4
H
9 1618 C H 3 4-i-C 3
H
7
-C
6
H
4 t-C 4
H
9 1619 CU 3 4-j-C 3
H
7
-C
6
H
4 n-C 6
H
1 3 1620 CU 3 4-i-C 3
H
7 -CsH 4 Prop-1-en-3-yJ.
1621 CU 3 4-i-C 3
H
7
-C
6
H
4 -1-Chloroprop-l-efl-3-y1 1622 CU 3 4-i-C 3
H
7
-C
6
H
4 Propyn-3--yJ.
1623 CH 3 4-i-C 3
H
7
-C
6
H
4 3-Methyl-but-2-efl-1-yl 1624 CH 3 2-OH-C 6
H
4
H
1625 CH 3 2-OH-C 6
H
4
CH
3 1626 CU 3 2-OH-C 6
H
4
CH
1627 CH 3 2-OH-C 6
H
4 n-C 3
H
7 1628 1CU 3 2-OH-C 6
H
4 iCH 1629 CH 3 2-OU--C 6
H
4 n-C 4
H
9 1630 CU 3 2-QU-C 6
H
4 t-C 4 H9 1631 CH 3 2.-OH-C 6
H
4 n-C 6
H
1 3 1632 CU 3 2-OH-C 6
H
4 Prop-l.-en-3-yl 1633 CU 3 2-OU--C 6
H
4 (E)-1-Chloroprop--el-3-y- 1634 CU 3 2-OH-C 6
H
4 Propyn-3-yl 1635 CU 3 2-OU-C 6
H
4 3-Methyl-but-2-en-1-yl 1636 CU 3 3-OH-C 6
H
4
H
1637 CU 3 3-OH-C 6
H
4
CU
3 1638 CU 3 3-OH-C 6
H
4
C
2
U
1639 CU 3 3-OU-C 6
H
4 n-C 3
H
7 1640 CU 3 3-OU-CGH 4 i-C 3
U
7 1641 CU 3 3-OU--C 6
U
4 n-C 4 Ug 1642 CU 3 3-OH-C 6
H
4 t-C 4 H9 1643 CU 3 3-OU-C 6
H
4 n-C 6
H
1 3 1644 CU 3 3-OH-C 6
H
4 Prop-1-en-3-yl 1645 CU 3 3-OU-C 6
H
4 (E)-1-Chloroprop-l-efl-3-yl 1646 CU 3 3-OU-C 6
H
4 Propyn-3-yl 1647 CU 3 3-OH-C 6
H
4 3-Methyl-but-2-en-1-yl 1648 CU 3 4-OU-C 6
H
4
U
1649 CU 3 4-OH-C 6
H
4
CU
3 1650 CU 3 4-OH-C 6
H
4
C
2
U
1651 CU 3 4-OU-C 6
H
4 n-C 3
U
7 1652 CU 3 4-OU-CGU 4 i-C 3
H
7 0000/44WflN No. R 3 R4
R
1653 CU 3 4-OH-CGU 4 n-C 4 H9 1654 CU 3 4-OH-C 6
H
4 t-C 4 Ug 1655 CU 3 4-OH-C6H 4 n-C 6 Hl 3 1656 CU 3 4-OH-C6H 4 Prop-1-en-3-yl 1657 CU 3 4-OH-C 6
H
4 (E)-1-Chloroprop-1-el-3-yJ- 1658 CU 3 4-OU--C 6
H
4 Propyn-3--yl 1659 CU 3 4-OH-C 6
H
4 3-Methyl-but-2-en-1-yl 1660 CU 3 2-OCH 3
-C
6
H
4
H
1661 CU 3 2-OCH 3
-C
6
U
4
CH
3 1662 CU 3 2-OCH 3
-C
6
H
4
C
2
H
1663 CU 3 2.-OCH 3
-C
6
H
4 n-C 3
H
7 1664 CU 3 2-OCH 3
-C
6
H
4 i-C 3
H
7 1665 CU 3 2-OCH 3
-C
6
H
4 n-C 4 H9 1666 CU 3 2-OCH 3
-C
6
H
4 t-C 4
H
9 1667 CU 3 2-OCH 3
-C
6
H
4 n-C 6
HI
3 1668 CU 3 2-OCH 3
-C
6
H
4 Prop-l-en-3-yl 1669 CU 3 2-OCH 3
-C
6
H
4 (E)-l-Chloroprop-l-el-3-y2.
1670 CU 3 2.-OCH 3
-C
6
H
4 Propyn-3-yJ.
1671 CU 3 2-OCH 3
-C
6
H
4 3-Methyl-but-2-efl-1-yl 1672 CU 3 3-OCH 3
-C
6
H
4
H
1673 CU 3 3-OCH 3
-C
6
H
4
CU
3 1674 CU 3 3-OCH 3
-C
6
H
4
C
2
H
1675 CU 3 3-OCH 3
-C
6
H
4 n-C 3
H
7 1676 CU 3 3-OCH 3
-C
6
U
4 i-C 3 H7 1677 CU 3 3-OCH 3
-C
6
H
4 n-C 4 H9 1678 CU 3 3-OCH 3
-C
6
H
4 t-C 4 H9 1679 CU 3 3-OCH 3
C
6
H
4 nC;j 1680 CU 3 3-OCH 3
-C
6
H
4 Prop-1--en--3-yl 1681 CU 3 3-OCH 3
-C
6
H
4 (E)-l-Chloroprop--el-3-yJ- 1682 CU 3 3-OCH 3
-C
6
H
4 Propyn-3-yJ.
1683 CU 3 3-OCH 3
-C
6
U
4 3-Methyl-but-2-el-1-yl 1684 CU 3 4-OCH 3
-C
6
U
4
U
1685 CU 3 4-OCH 3
-C
6
H
4
CU
3 1686 CU 3 4-OCH 3 -CGU4 C 2
HS
1687 CU 3 4-OCH 3
-C
6
H
4 n-C 3
H
7 1688 CU 3 4-OCH 3
-C
6
H
4 i-C 3
H
7 1689 CU 3 4-OCH 3
-C
6
H
4 n-C 4
H
9 1690 CU 3 4-OCH 3
-CGH
4 t-C 4 H9
RA
~4 No. 3R4R 1691 CH 3 4-OCH 3
-C
6
H
4 n-C 6
HO
1692 CR 3 4-OCH 3
-C
6
H
4 Prop-1-en-3-y3.
1693 CH 3 4-OCH 3
-C
6 fR 4 (E)-1-Chloroprop-1-en-3-y.
1694 CH 3 4-OCHi 3
-C
6
H
4 Propyn-3-yl.
1695 CR 3 4-OCH 3
-C
6
H
4 3-Methy1-but-2-en-1-yl 1696 CR 3 2-0C 2
H
5
-C
6
H
4
H
1697 CR 3 2-0C 2
H
5
-C
6
H
4
CH
3 1698 CH 3 2-0C 2 H_9-C 6
H
4
C
2
H
1699 CR 3 2-0C 2
HS-C
6
H
4 n-C 3
H
7 1700 CR 3 2-0C 2
H
5
-C
6
H
4 i-C 3
H
7 1701 CH 3 2-0C 2
H
5
-C
6
H
4 n-C 4
H
9 1702 CR 3 2-0C 2
H
5
-C
6
H
4 t-C 4
H
9 1703 CR 3 2-0C 2
H
5
-C
6
H
4 n-C 6
H
1 3 1704 CR 3 2-0C 2
H
5
-C
6
H
4 Prop-1--en-3-yl 1705 CR 3 2-0C 2
H
5
-C
6
H
4 (E)-1-Chloroprop--el-3-y 1706 CR 3 2-0C 2
R
5
C
6
H
4 Propyn-3-yl 1707 CR 3 2-0C 2
H
5
-C
6
H
4 3-Methyl-but-2-en-1-yl 1708 C11 3 3-0C 2
H
5
-C
6
H
4
H
1709 CH 3 3-0C 2
HS-C
6
H
4
CR
3 1710 CR 3 3-0C 2
H
5
-C
6
H
4
C
2
H
1711 CR 3 3-0C 2
H
5
-CGH
4 n-C 3
H
7 1712 CR 3 3-OC 2 H5-C 6
H
4 i-C 3
H
7 1713 CR 3 3-0C 2
H
5
-C
6
H
4 n-C 4
H
9 1714 CR 3 3-0C 2
H
5
-CGH
4 t-C 4
H
9 1715 CR 3 3-0C 2
HR
5
-C
6
H
4 n-C 6
H
1 3 1716 CR 3 3-0C 2
H
5
-C
6
H
4 Prop-.1-en-3-yl 1717 CR 3 3-0C 2
H
5
-C
6
H
4 -1-Chloroprop-1-en-3-yl 1718 CR 3 3-0C 2
H
5
-CGH
4 Propyn-3-yJ.
1719 CR 3 3-0C 2
H
5
-C
6
H
4 3-.Methyl-but-2-en-1-yl 1720 CR 3 4-0C 2
H
5
-C
6
H
4
H
1721 CR 3 4-0C 2
H
5 -CfH 4
CH
3 1722 CR 3 4-0C 2
H
5
-C
6
H
4
C
2
H
1723 CR 3 4-0C 2
H
5
-C
6
H
4 n-C 3
H
7 1724 CR 3 4-0C 2
H
5
C
6
H
4 i-C 3
H
7 1725 CR 3 4-0C 2
H
5
-C
6 Ei 4 n-C 4
H
9 1726 CR 3 4-0C 2
HS-C
6
H
4 t-C 4
H
9 1727 CR 3 4-0C 2
H
5
-C
6
R
4 n-C 6
H
1 3 1728 CR 3 4-QC 2 H5-CsR 4 Prop-1-en--3-yl 00 90 44 "7 0 No. R 4R 17 29 CH 3 4-0C 2
HS-C
6
H
4 -1-chloroprop-1-efl-3-yl 1730 CU, 3 4-0C 2
U
5
-C
6
U
4 Propyrn-3-yi 1731 CH 3 4-OC2HS-C 6
H
4 3-Methyl-but-2-en--1-yl 1732 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4
H
1733 CH 3 2-0-(i-C 3 7
)-C
6
H
4
CU
3 1734 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4
C
2
HS
1735 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 n-C 3
H
7 1736 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 i-C 3
H
7 1737 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 n-C 4
H
9 1738 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 t-C 4
H
9 1739 CU 3 2-0-(i-C 3
H
7
)-CGU
4 n-C 6
H
1 3 1740 CU 3 2-0- (i-C 3
H
7
)-C
6
H
4 Prop-1-en-3-yJ.
1741 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 (E)-1-Chloroprop-l-el-3-yJ.
1742 CU 3 2-0-(i-C 3
H
7
)-C
6
H
4 Propyn-3-yl 1743 CU 3 2-O-(i-C 3
H
7
)-C
6
H
4 3-Methyl-but-2-en-1-y1 1744 CU 3 3-0-(i-C 3
H
7
)-C
6
H
4
H
1745 CU 3 3-0-(i-C 3
H
7
)-C
6
U
4
CH
3 1746 CU 3 3-0-(i-C 3
H
7
)-C
6
H
4
C
2
H
1747 CU 3 3-0- (i-C 3
H
7
)-C
6
H
4 n-C 3
H
7 1748 CU 3 3-0- (i-C 3
H
7
)-C
6
H
4 i-C 3
H
7 1749 CU 3 3-0- (i-C 3
H
7
)-C
6
U
4 n-C 4
H
9 1750 CU 3 3-0- (i-C 3
H
7
)-C
6
H
4 t-C 4
H
9 1751 CU 3 3-0- (i-C 3
H
7
)-C
6
H
4 n-C 6 Hl 3 1752 CU 3 3-0-(i-C 3
U
7
)-CGH
4 Prop-1-eii-3-yl 1753 CU 3 3-0-(i-C 3
U
7
)-C
6
H
4 (E)-1-Chloroprop-1-efl-3-y1 1754 CU 3 3-0- (i-C 3
H
7
)-C
6
H
4 Propyn-3-yl.
1755 CH 3 3-0- (i-C 3
H
7
)-C
6
H
4 3-Methyl-but-2-efl-1-yl 1756 CU 3 4-0-(i-C 3
H
7
)-C
6
U
4
H
1757 CU 3 4-0-(i-C 3
U
7
)-C
6
H
4
CU
3 1758 CU 3 4-0-(i-C 3
H
7
)-C
6
H
4
C
2
HS
1759 CU 3 4-0-(i-C 3
H
7
)-C
6
U
4 n-C 3
H
7 1760 CU 3 4-0-(i-C 3
H
7
)-C
6
U
4 i-C 3
U
7 1761 CU 3 4-0- (i-C 3
U
7
)-C
6
U
4 n-C 4 Ug 1762 CU 3 4-0-(i-C 3
U
7
)-C
6
U
4 t-C 4
U
9 1763 CU, 3 4-0-(i-C 3
U
7
)-C
6
U
4 n-CGU 1 3 1764 CU 3 i-C 3
H
7
)-C
6
U
4 Prop-1-en-3-yl 1765 CU 3 4-0- (i-C 3
U
7
-C
6
H
4 (E Chloroprop---el-3-y- 1766 'CU 3 14-0- (i-C 3
U
7
)-C
6
U
4 Propyn-3-yl 006l0 /44670 No. i 1767 CH 3 4-0- i-C3F1; -C 6 1' 4 3-Metfhy1-but-2-onl--Yl 1768 CU 3 2-0-(t-C 4
HP)-C
6
H
4
H
1769 CHU 3 2-0- t-C 4 UO -CrH 4
CH
3 1770 Cl] 3 2-0- (t-C4fl9) -C61' 4
C
2 fl 1771 C H 3 1 2-0- (t-C 4 H9) -CON4 f-C 3
H
7 1772 CU 3 2-0- (t-C 4
H
9
)-CGH
4 i-C 3
H
7 1773 CU 3 2-0-(t-C 4
H
9
)-C
6
H
4 n-C 4 Ug 1774 CH 3 2-0- t-C 4 Hq) -C 6
H
4 t-C 4
H
9 1775 CH 3 2-0-(t-C 4 g)-CU4 n-C 6
H
1 3 1776 CH 3 2-0- (t-C 4 Hg -C 6 11 4 Prop-1-en-3-y) 1777 CH 3 2-0- (t-C 4
H
9
-CGH
4 (E)--Chloroprop-l-efl-3-yl 1778 CU 3 2-0- (t-C 4
H)-
6
H
4 Propyn-3-yl 1779 CU 3 2-0- (t-C 4 U -C6H 4 3-Methyl-but-2-en-1-y1 1780 CU 3 3-0-(t-C 4 H9)-C 6
H
4
H
1781 CU 3 3-0-(t-C 4 H9)-C 6
H
4
CR
3 1782 CU 3 3-0-(t-C 4
H
9
)-C
6
H
4
C
2
H
1783 CU 3 3-0- (t-C 4 H9) -C 6
U
4 n-C 3
H
7 1784 CU 3 3-0-(t-C 4
H
9
)-C
6
H
4 i-C 3
U
7 1785 CU 3 3-0-(t-C 4
H
9
)-C
6
H
4 n-C 4
H
9 1786 CU 3 3-0.-(t-C 4 Hg)-C 6
H
4 t-C 4 Ug 1787 CU 3 3-0-(t-C 4 H9)-C 6
H
4 n-C 6 1- 1 3 1788 CU 3 3-0-(t-C 4
U
9
)-C
6
H
4 Prop-1-en-3-yl 1789 CU 3 3-0-(t-C 4 Ug)-C 6
U
4 (E)-1-Chloroprop-1-efl-3-yl 1790 CU 3 3-0-(t-C 4
H
9
)-C
6
U
4 Propyn-3-yl 1791 CU 3 3-0- (t-C 4
H
9
)-C
6
H
4 3-Methyl-but-2-efl-1-yl 1792 CU 3 4-0-(t-C 4 H9)-C 6
H
4
H
1793 CH 3 4-0- (t-C 4
U
9
-C
6 4
CU
3 1794 CU 3 4-0-(t-C 4
H
9
)-C
6
U
4
C
2
U
1795 CU 3 4-0-(t-C 4
H
9
)-C
6
H
4 ri-C 3
U
7 1796 CU 3 4-0- (t-C 4 H -C 6
U
4 i-C 3
H
7 1797 CH 3 4-0-(t-C 4 H9)-C 6 H4 n-C 4
U
9 1798 CH 3 4-0-(t-C 4
H
9
)-C
6
H
4 t-C 4 H9 1799 CU 3 4-0-(t-C 4 H9)-C 6
H
4 n-C 6
H
1 3 1800 CU 3 4-0-(t-C 4
H
9
)-C
6
U
4 Prop-1-ei-3-y.
1801 CU1 3 4-0-(t-C 4 H9)-C 6
U
4 (E)-1-Chloroprop-1-el-3-yl 1802 CU 3 4-0- (t-C 4 H -C 6
U
4 Propyn-3-y.
1803 CU 3 4-0- (t-C 4
H
9
)-C
6
H
4 3-Methyl-but-2-el-1-yJ- 184CU 3 2-CF 3
-C
6
H
4
IH
0000/44376 1805 CU 3 2-CF3-C(,H 4 1806 CH 3 2-C] 5-CGH4 C 2
HS
1807 CI-13 2-CF3-C 6 Ili 4 n-C~f] 7 1808 CU 3 2"CF3-C0U 4 i-C3H 7 1809 CH3 2.-CF 3
-COH
4 n-C 4
H
9 1810 CU 3 2-CF 3
-C
6
H
4 t-C 4
H
9 1811 CU 3 2-CF 3
-C
6 Hi 4 n-C 6 HU3 1812 CU 3 2-CF 3
-C
6
H
4 Prop-1-en-3-yJ- 1813 CH 3 2-CF 3
-C
6
H
4 (E)-1-Chloroprop-1-erl-3-yl 1814 CU 3 2-CF' 3
-C
6 11 4 Propyn-3-yJ.
1815 CU 3 2-CF 3
-C
6
H
4 3-Methyl--but-2-el-1-yl 1816 CH 3 3-CF 3
-C
6
U
4
H
1817 CU 3 3-CF 3
-C
6
H
4
CU
3 1818 CH 3 3-CF 3
-C
6
U
4
C
2
HS
1819 CH 3 3-CF 3
-C
6
H
4 n-C 3
H
7 1820 CH 3 3-CF 3
-C
6
H
4 i-C 3
H
7 1821 CU 3 3-CF 3
-C
6
H
4 n-C 4 H9 1822 CU 3 3-CF 3
-CGH
4 t-C 4
H
9 1823 CU 3 3-.CF 3
-C
6
H
4 n-C 6
H
1 3 1824 CU 3 3-CF 3
-CGH
4 Prop-1-en-3-y2.
1825 CU 3 3-CF 3
-C
6
H
4 (E)-1-Chloroprop-1-el-3-yl 1826 CH 3 3-CF 3
-C
6
H
4 Propyn-3--yl 1827 CU 3 3-CF 3
-C
6
H
4 3-Methyl-but-2-enl-yl 1828 CH 3 4-CF 3
-C
6
H
4
H
1829 CU 3 4-CF 3
-C
6
H
4
CH
3 1830 CU 3 4-CF 3
-C
6
H
4
C
2
H
1831 CU 3 4-CF 3
-C
6
H
4 ri-C 3
U
7 1832 CU 3 4-CF 3
-C
6
H
4 i-C 3
H
7 1833 CU 3 4-CF 3
-C
6
H
4 n-C 4
U
9 1834 CU 3 4-CF 3
-C
6
U
4 t-C 4
U
9 .1835 CU 3 4-CF 3
-C
6
H
4 n-C 6 Hj 3 1836 CU 3 4-CF 3
-C
6
H
4 Prop-l-en-3-yl 1837 CU 3 4Z-CF 3
-C
6
H
4 -1-Chloroprop-l-en-3-yl 1838 CU 3 4-CF 3
-C
6
H
4 Propyn-3-yl 1839 CU 3 4-CF 3
-C
6
H
4 3-Methyl-but-2-el-1-y2.
1840 CU 3 2.-NH 2
-C
6
H
4
U
1841 1CU 3 2-NH 2
-C
6
H
4
ICU
3 1842 ICU 3 12-IH 2
-CGH
4
IC
2 Hs 000)/ 44079/ No. 1 J R 4
R
1843 C1{3 2-NH 2 -C6U4 n-C 3
H
7 1844 CH3 2-NH 2
C
6
FH
4 i.-C~lU 7 1845' CH 3 2-NH 2
-C
6
H
4 n-C 4
H
9 1846 CH 3 2-NU 2 -CrH 4 t-C 4
H
9 1847 CU 3 2-NH 2
-C
6
H
4 n-C 6
H
1 3 1848 CU 3 2-NH 2
-C
6
H
4 Prop-1-en--3-yl 1849 CU 3 2-NH 2
-C
6
H
4 (E)-l-Chloroprop-1-el-3-yJ- 1850 CU 3 2-NH 2
-C
6
H
4 Propyn.-3-yJ 1851 CU 3 2-NH 2 -C6H 4 3-Methy-but-2-efl-1 -yl 1852 CH 3 3-NH 2
-C
6
H
4
H
1853 CU 3 3-NU 2
-C
6
H
4
CH
3 1854 CU 3 3-NU 2
-C
6
H
4
C
2
-H-
1855 CU 3 3-NH2-C6U4 n-C 3
H
7 1856 CU 3 3-NH 2
-C
6
H
4 i-C 3
H-
1857 CH 3 3-NH 2
-C
6
U
4 n-C 4
H
9 1858 CU 3 3-NU 2
-C
6
H
4 t-C 4 Ui 9 1859 CU 3 3-NU 2
-C
6
H
4 n-C 6 Hl 3 1860 CU 3 3-NH 2
-C
6
H
4 Prop-1--en--3-yl 1861 CU 3 3-NH 2
-C
6
H
4 (E)-l-Chloroprop--el- 3 -yl 1862 CU 3 3-NH 2
-C
6
H
4 Propyn-3-yl 1863 CH 3 3-NH 2
-C
6
H
4 3-Methyl-but-2-el-1-yl 1864 CU 3 4-.NH 2
-C
6
H
4
H
1865 CU 3 4-NH 2
-C
6
U
4
CH
3 1866 CU 3 4-NU 2
-C
6
H
4
C
2
H
1867 CH 3 4-NH 2
-C
6
H
4 n-C 3
U
7 1868 CU 3 4-NH 2
,-C
6
H
4 iCH 1869 CU 3 4-NU 2
-C
6 H4 n-C 4
U
9 1870 CU 3 4-NH 2
-C
6
H
4 t-C 4
H
9 1871 CU 3 4-NU 2
-C
6
H
4 n-C 6 Hl 3 1872 CU 3 4-NU 2
-C
6
H
4 Prop-1-en-3-yl 1873 CU 3 4-NH 2
-C
6
U
4 (E)-l-Chloroprop--el- 3 -y) 1874 CU 3 4-NU 2
-C
6
H
4 Propyn-3-yI.
1875 CU 3 4-NH 2
-C
6
H
4 3-Methyl-but-2-efl-1-yl 1876 CU 3 2.-NMe 2
-C
6
U
4
U
1877 CU 3 2-NMe 2
-C
6
H
4
CU
3 1878 CU 3 2-NMe 2
-C
6
H
4
C
2
H
1879 CU 3 2-NMe 2 -C6U4 n-C 3
U
7 1880 CU 3 2-NMe 2
-C
6
U
4 i-C 3
H
7 005~0 /44575 No. R 3 -4 Rs 1881 CM 3 2-NMe 2
-CGH
4 -49 1882 CM 3 2-NMe 2
-C
6
H
4 t-C 4
H
9 1883 CM 3 2-NMe 2
-C
6
H
4 n-.C 6 Ii 1 3 1884 CH 3 2-NMe 2
-C
6
H
4 Prop-1-en-3-y- 1885 CH 3 2-NMe 2
-C
6
H
4 (E)-l-Chloroprop-l-Cfl-3-y 2 1886 CM 3 2-NMe 2
-C
6
H
4 Propyn-3-yl 1887 CM 3 2-NMe 2
-C
6
M.
4 3-Methyl-but-2-en-l-yl 1888 CM 3 3-NMe 2
-C
6
H
4
H
1889 CM 3 3-NMe 2
-C
6
M
4
CH
3 1890 CM 3 3-NMe 2
-C
6
H
4
C
2
HS
1891 CH 3 3-NMe 2
-C
6 1 4 n-C 3
H
7 1892 CH 3 3-NMe 2
-C
6
H
4 i-C 3
H
7 1893 CM 3 3-NMe 2
-C
6
H
4 n-C 4
H
9 1894 CH 3 3-NMe 2
-C
6
H
4 t-C 4
H
9 1895 CH 3 3-NMe 2
-C
6
H
4 n-C 6 Hl 3 1896 CM 3 3-NMe 2
-C
6
H
4 Prop-1-en-3-yJ.
1897 CH 3 3-NMe:!-C 6
H
4 (E)-l-Chloroprop-1-el-3-yJ- 1898 CH 3 3-NMe 2
-C
6
H
4 Propyn-3-yJ.
1899 CM 3 3-NMe 2
-C
6
H
4 3-Methyl-but-2--en-1-yl 1900 CH 3 4-NMe 2
-C
6
H
4
H
1901 CM 3 4-NMe 2
-C
6
H
4
CM
3 1902 CM 3 4-NI-fe 2
-C
6
H
4
C
2 1903 CM 3 4-NMe 2
-C
6
H
4 n-C 3
H
7 1904 CH 3 4-NMe 2
C
6
H
4 i-C 3
H
7 1905 CM 3 4-NMe 2
-C
6
H
4 n-C 4 H9 1906 CM 3 4-NMe 2
-C
6
H
4 -4, 1907 CM 3 4-NMe 2
-C
6
H
4 n-C 6
H
1 3 1908 CM 3 4-NMe 2
-C
6
H
4 Prop-l-en-3-yJ.
1909 CM 3 4-NMe 2
-C
6
H
4 (E)-l-Chloroprop-1-efl-3-yl 1910 CM 3 4-NMe 2
-C
6
H
4 Propyn-3-yJ.
1911 CH 3 4-NMe;!-CZH 4 3-Methyl-but- 2-en-1-yl 1912 CM 3 2-A~nothiocarbo- H nyl-C 6
H
4 1913 CM 3 2-Aminothiocarbo- CM 3 nyl-CGH 4 1914 CM 3 2-Axinothiocarbo- C 2
M
nyl-CGH 4 1915 CM 3 2-Aninothiocarbo- h-C 3
M
7 _nyl-C 6
H
4 I 0050/445 No. R 3 R4R 1916 CH 3 2-Aiinothiocarbo- i-C 3
H
7 nyl-C 6
H
4 1917 CU 3 2-Aminothiocarbo- n-C 4
H
9 6
H
4 1918 CU 3 2-Aminothiocarbo- t-C 4
U
9 ___nyl-C 6
H
4 1919 CU 3 2-Aiinothiocarbo- n-C 6
H
1 3 nyl-C 6
U
4 1920 CU 3 2-Aminothiocarbo- Prop-1-en-3-yl nyl-C 6
H
4 1921 CU 3 2-Arninothiocarbo- (E)-l-Chloroprop-1-en-3-yl ___nyl-C 6
H
4 1922 CU 3 2-Axninothiocarbo- Propyn-3-yl nyl-C 6
H
4 1923 CH 2-Aininothiocarbo- 3-Methyl-but--2-en-1-yl nyl-C 6
H
4 1924 CU 3 -Aminothiocarbonyl-C 6
H
4 1925 CU 3 3-Aiinothiocarbo- IC11 3 6
U
4 1926 CU9 3 3-Aminothiocarbo- C 2
U
6
U
4 1927 CU 3 3-Aminothiocarbo- n-C 3
H
7 6
U
4 1928 CU 3 3-Aninothiocarbo- i-C 3
H
7 6
U
4 1929 CH 3 3-Aininothiocarbo- n-C 4
U
9 6
U
4 1930 C2H 3 3-Aininothiocarbo- t-C 4 Ug 6
U
4 1931 CU 3 3-Aminothiocarbo- n-.C 6
U
13 6
U
4 1932 CU 3 3-Aminothiocarbo- Prop-1-en-3-yl nyl-C 6
U
4 19 3 CU 3 3-Aminothiocarbo- (E)-1-Chloroprop-1-en-3-y1 nyl-C 6
H
4 r1934 CU 3 3-Axninothiocarbo- Propyn-3-y.
nyl-C 6
U
4 1935 CU 3 3-AnUinothiocarbo- 3-Methyl-but-2-en-1-ynyl-C 6
U
4 1936 CU 3 4-Aininothiocarbo- U nyl-C 6
H
4 1937 CU 3 4-Amninothiocarbo- CU 3 nyl-C 6
U
4 1938 CU 3 4-Anminothiocarbo- C 2
U
~nyl-C 6
H
4 0050/44575 No. R 3 R4R 1939 CU 3 4-Arinothiocarbo- n-C 3 H7 nyl-C 6
U
4 1940 CU 3 4-Aminothiocarbo- i-C 3
U
7 n'yl-C 6
H
4 1941 CU 3 4-Aminothiocarbo- 4
H
9 nYl-C 6
H
4 1942 CU 3 4-Aminothiocarbo- t-C 4
U
9 nyl-C 6
H
4 1943 CB 3 4-Aiinothiocarbo- n-C 6
H
1 3 nyl-C 6
H
4 1944 CH 3 4-Aminothiocarbo- Prop-l-en-3-yl nyl-C 6
H
4 1945 CU 3 4-Axninothiocarbo- (E)-l-Chloroprop-1-en-3-ynyl-C 6
H
4 1946 CU 3 4-.Axinothiocarbo- Propyn-3-yJ.
nyl-C 6
H
4 1947 CU 3 4-Aminothiocarbo- 3-Methyl-but-2-el-1-y.
nyl-C 6
H
4 1948 CH 3 2.-OneF 3
-C
6
H
4
H
1949 CU 3 2-OCF 3
-C
6
H
4
CH
3 1950 CU 3 2-OCF 3
-C
6
U
4
C
2
HS
1951 CH 3 2-OCF 3
-C
6
H
4 n-C 3
H-
1952 CH 3 2-OCF 3
-C
6
H
4 i-C 3
H
7 1953 CU 3 2-OCF 3
-C
6
U
4 n-C 4 H9 1954 CU 3 2-OCF 3
-C
6
H
4 t-C 4
H
9 1955 CU 3 2-OCF 3
-C
6
U
4 n-C 6
U
1 3 1956 CU 3 2-OCF 3
-C
6
U
4 Prop-1-en-3-yl 1957 CU 3 2-OCF 3
-C
6
U
4 (E)-1-Chloroprop--el-3-y- 1958 CU 3 2-OCF 3
-CGH
4 Propyn-3-yl 1959 CU 3 2-OCF 3
-C
6
H
4 3-Methyl-but-2-el-1-yJ- 1960 CU 3 3-OCF 3
-C
6
U
4
U
1961 CU 3 3-OCF 3
-C
6
H
4
CU
3 1962 CU 3 3-oCF 3
-C
6
H
4
C
2
U
1963 CU 3 3-OCF 3
-C
6
U
4 n-C 3
U
7 1964 CU 3 3-QCF 3
-C
6
H
4 i-C 3
H
7 1965 CU 3 3-OCF 3
-CGU
4 n-C 4 Ug 1966 CU 3 3-OCF 3
-C
6
H
4 t-C 4 H9 1967 CU 3 3-OCF 3
-C
6
H
4 n-C 6
U
1 3 1968 CU 3 3-OCF 3
-C
6
H
4 Prop-l-en-3-yJ.
1969 CU 3 3-OCF 3
-C
6
H
4 (E)-1-Chloroprop-1-9fl-3-yl 1970 1CU 3 3-OCF 3
-C
6
H
4 Propyn-3-yl 0050/44575 No. RR4R 1971 CE 3 3-OCF 3
-CGH
4 3-Methyl-but-2-efl-1-yl 1972 CE 3 4-OCF 3
-C
6
H
4
H
1973 CE 3 4-OCF 3
-C
6
H
4
CE
3 1974 CE 3 4-OCF 3 -C6H 4
C
2
H
1975 CH 3 4-OCF 3
-C
6
H
4 n-C 3
H
7 1976 CE 3 4-OCF 3
-C
6
H
4 i-C 3
H
7 1977 CH 3 4-OCF 3
-C
6
H
4 n-C 4 H9 1978 CH 3 4-OCF 3
-C
6
H
4 t-C 4
H
9 1979 CE 3 4-OCF 3
-C
6
H
4 n-C 6
H
1 3 1980 CE 3 4-OC F 3
-C
6
H
4 Prop-l-en-3-yl 1981 CE 3 4-OCF 3
-C
6
H
4 (E)-1-Chloroprop-1-el-3-yl 1982 CH 3 4-OCF 3
-C
6
H
4 Propyn-3-yl 1983 CH 3 4-OCF 3
-C
6
H
4 3-Methyl-but-2-el-1-y2- 1984 CE 3 2-SCH 3
-C
6
H
4
H
1985 CE 3 2-SCH 3
-C
6
H
4
CH
3 1986 CE 3 2-SCH 3
-C
6
H
4
C
2
H
1987 CE 3 2-SCH 3
-C
6
H
4 n-C 3
H
7 1988 CE 3 2.-SCH 3
-C
6
H
4 i-C 3
H
7 1989 CE 3 2-SCH 3
-C
6
H
4 n-C 4 H9 1990 CE 3 2-SCH 3
-CGH
4 t-C 4 Eg 1991 CE 3 2-SCH 3
-C
6
H
4 n-C 6
H
1 3 1992 CE 3 2-SCH 3
-C
6
H
4 Prop-l-en-3-yl 1993 CE 3 2-SCH 3
-C
6
H
4 (E)-1-ChJloroprop-1-efl-3-yl 1994 CE 3 2-SCE 3
-C
6
H
4 Propyn-3-yl 1995 CE 3 2-SCH 3
-C
6
H
4 3-Methyl-but-2-el-1-yl 1996 CE 3 3.-SCH 3
-C
6
E
4
H
1997 CE 3 3-SCH 3
-C
6
H
4
CH
3 1998 CE 3 3-SCH 3
-C
6
H
4
C
2
H
1999 CE 3 3-SCH 3
-C
6
H
4 n-C 3
E
7 2000 CE 3 3-SCH 3
-C
6
H
4 iCH 2001 CE 3 3-SCH 3
-Q
6
E
4 n-C 4 H9 2002 CE 3 3-SCH 3
-C
6
H
4 t-C 4
H
9 2003 CE 3 3-SCH 3
-C
6
H
4 n-C 6
H
1 3 2004 CE 3 3-SCH 3
-C
6
H
4 Prop-1-en-3--yl 2005 CE 3 3-SCH 3
-C
6
H
4 (E)-1.-Chloroprop--el-3-yJ- 2006 CE 3 3-SCH 3
-C
6
H
4 Propyn-3-yl 2007 CE 3 3-SCH 3
C
6
H
4 3-Methyl-but-2-el-1-y.
208CH 3 147SCE 3
-C
6
H
4
H
0050/44575 No. R 3 R4R 2009 CH 3 4-SCH 3
-C
6
H
4
CH
3 2010 CH 3 -A -SCH 3
-C
6
H
4
C
2 2011 CH- 3 4-SCH 3
-C
6
H
4 n-C 3
H
7 2012 CU 3 4-SCH 3
-C
6
H
4 iCH 2013 CU 3 4-SCH 3
-C
6
H
4 n-C 4
H
9 2014 CU 3 4-SCH 3
C
6
H
4 t-C 4 H9 2015 CU 3 4-SCH 3
-C
6
U
4 n-C 6
H
1 3 2016 CU 3 4-SCH 3
-C
6 Hl Prop-l-en-3-yl 2017 CH 3 4-SCH 3
-C
6
H
4 (E)-1-Chloroprop-l-efl-3-y1 2018 CU 3 4-SCH 3
-C
6
H
4 Propyn-3-yl 2019 CU 3 4-SCH 3
-C
6
H
4 3-Methyl-but-2-efl-1-yl 2020 CU 3 2-Methyl- H sulfonyl-C 6
H
4 2021 CH 3 2-Methyl- CH 3 sulfonyl-C 6
H
4 2022 CU 3 2-Methyl- C 2
HS
sulfonyl-C 6
H
4 2023 CU 3 2-Methyl- n-C 3
H
7 sulfonyl-C 6
H
4 2024 CU 3 2-Methyl- i-C 3
H
7 sulforiyl-C 6
H
4 2025 CF4 3 2-Methyl- n-C 4
H
9 sulfonyl-C 6
H
4 2026 CH 3 2-Methyl- t-C 4
H
9 sulfonyl-C 6 H4 2027 CU 3 2-Methyl- n-C 6 Hj 3 sulfonyl-C 6 H4 2028 CU 3 2-Methyl- Prop-1-en-3-yl sulfonyl-C 6
H
4 2029 CH 3 2-Methyl- (E)-1-Chloroprop-1-el-3-yl SUlfOnYl-C 6 H4 2030 CU 3 2-Methyl- Propyn-3-yl sulfonyl-C 6 H4 2031 CU 3 2-Methyl- 3-Methyl-but-2-el-1-ysulfonyl-C 6 H4 2032 CU 3 3-Methyl- H sulfonyl-C 6 H4 2033 CU 3 3-Methyl- C14- 3 sulf onyl--C 6 2034 CU 3 3-Methyl- C 2
HU
sulfonyl-C 6 H4 2035 C 3 3-Methyl- n-C 3
H
7 sulfonyl-C 6 H4 0050/44575 No. RR4R 2036 CE 3 3-Methyl- i-C 3
H
7 sulfonyl-C 6
H
4 2037 CE 3 3-Methyl- n-C 4 H9 sulfonyl-C 6
H
4 2038 CE 3 3-.Methyl- t-C 4
H
9 SUlfOnYl-C 6
H
4 2039 CE 3 3-Methyl- n-C 6 Hl 3 sulf onyl-c 6
H
4 2040 CE 3 3-Methyl- Prop-l-en-3-y.
sulf onyl-C 6
H
4 2041 CE 3 3-Methyl- (E)-l-Chloroprop--el- 3 -yJsulfonyl-C6H4 152042 CE 3 3-Methyl- Propyn-3- il sulf onyl-C 6
H
4 2043 CH 3 3-Methyl- 3-Methyl-but-2-efl-1-yl sulfonyl-C6H 4 2044 CE 3 4-Methyl-
H
onyl-CEE 4 2045 CE 3 4-Methyl- CH 3 sulfonyl-C 6
H
4 2046 CE 3 4-Methyl- C 2
H
sulf onyl-C0E 4 2047 CE 3 4-Methyl- n-C 3
H
7 sulfonyl-C 6
H
4 2048 CE 3 4-Methyl- iCH sulf onyl-C 6
E
4 2049 CE 3 4-Methyl- n-C 4 H9 sulfonyl-C6
H
4 2050 CE 3 4-Methyl- t-C 4
H
9 sulfonyl-C6H 4 2051 CE 3 4-Methyl- n-C 6
H
1 3 sulfonyl-C6H 4 352052 CE 3 4-Methyl- Prop-l-en-3-yl sulfonyl-C 6
H
4 2053 CE 3 4-Methyl- (E)-l-Chloroprop-l-efl-3-yl sulfonyl-C 6
H
4 2054 CE 3 4-Methyl- Propyn-3-yl sulfonyl-C 6
H
4 2055 CE 3 4-Methyl- 3-Methyl-but-2-el-1-yl sulf onyl-C 6
H
4 2056 CE 3 2-Methoxycarbo-
H
nyl-C 6
H
4 2057 CE 3 2-Methoxycarbo- CE 3 nyl-CsE 4 2058 CE 3 2-Methoxycarbo-
C
2
E
6
H
4 zu 0050/44575 No. R 3 R4R 2059 CH 3 2-Methoxycarbo- n-C 3
H
7 nyl-C 6
H
4 2060 CE 3 2-Methoxycarbo- i-C 3
H
7 nyl-C 6
H
4 2061 CH 3 2-Methoxycarbo- n-C 4 H9 nyl-C 6
H
4 2062 CH 3 2-Methoxycarbo- t-C 4 H9 nyl-C 6
H
4 2063 CH 3 2-Methoxycarbo- n-C 6
H
13 nyl-C 6
H
4 2064 CE 3 2-Methoxycarbo- Prop-l-en-3-yl nyl-CGH 4 2065 CE 3 2-Methoxycarbo- (E)-1--Chloroprop-1-efl-3-yl nyl-CGH 4 2066 CE 3 2-Methoxycarbo- Propyn-3-y.
nyl-C 6
H
4 2067 CE 3 2-Methoxycarbo- 3-Methyl-but-2-efl-1-yl nyl-C 6
H
4 2068 CE 3 3-Methoxycarbo-
H
nyl-C 6
H
4 2069 CE 3 3-Methoxycarbo- CE 3 nyl-C 6
H
4 2070 CE 3 3-Methoxycarbo-
C
2 nyl-C 6
E
4 2072. CE 3 3-Methoxycarbo- n-C 3
E
7 nyl-C 6
E
4 2072 CE 3 3-Methoxycarbo- i-C 3
HE
7 nyl-C 6
H
4 2073 CE 3 3-Methoxycarbo- n-C 4 H9 nyl-C 6
H
4 2074 CE 3 3-Methoxycarbo- t-C 4
H
9 nyl-C 6
H
4 2075 CE 3 3-Methoxycarbo- n-C 6
E
1 3 nyl-C 6
H
4 2076 CE 3 3-Methoxycarbo- Prop-l-en-3-yl nyl-C 6
H
4 2077 CE 3 3-Methoxycarbo- (E)-l-Chloroprop-l-efl-3-yJ.
nyl-C 6
H
4 2078 CE 3 3-Methoxycarbo- Propyn-3-ynyl-C 6
E
4 2079 CE 3 3-Methoxycarbo- 3-Methyl-but-2-efl-1-yl nyl-C 6
H
4 2080 C11 3 4-Methoxycarbo-
E
nyl-C 6
H
4 201CE 3 4-Methoxycarbo- CE 3 nyl-C 6
H
4 I 0050/4579 No. R3 R4 2082 CH 3 4-Methoxycarbo-
C
2
H
nyl-CGH 4 2LI83 CH 3 4-Methoxycarbo- n-C 3
H
7 nyl-C 6
H
4 2084 CH 3 4-Methoxycarbo- i-C 3
H
7 nyl-C 6
H
4 2085 CE 3 4-Methoxycarbo- n-C 4 H9 nyl-C 6
H
4 2086 CE 3 4-Methoxycarbo- t-C 4
H
9 nyl-C 6
H
4 2087 CE 3 4-Methoxycarbo- n-C 6
H
1 3 nyl-C 6
H
4 2088 CE 3 4-Methoxycarbc- Prop-1--en-3-ynyl-C 6
H
4 2089 CE 3 4-Methoxycarbo- (E Chloroprop-l-el-3-yl nyl-C 6
H
4 2090 CE 3 4-Methoxycarbo- Propyn-3-yl nyl-C 6
H
4 2091 CH 3 4-Methoxycarbo- 3-Methyl-but-2-ef-l--y1 nyl-C 6 H4 2092 CE 3 2-Ethoxy-
H
carbonyl-C 6 H4 2093 CE 3 2-Ethoxy-
CH
3 :arbonyl-C6H4 2094 CE 3 2-Ethoxy-
C
2
HE
carbonyl-C6H4 2095 CE 3 2-Ethoxy- n-C 3
H
7 carbonyl-C6H4 2096 CE 3 2-Ethoxy- i-C 3
H
7 carbonyl-C 6
H
4 2097 CE 3 2-Ethoxy- n-C 4 H9 carbonyl-C6H4 2098 CE 3 2-Ethoxy- t-C 4 H9 carbonyl-C 6 2099 CE 3 2-Ethoxy- n-C 6
H
1 3 carbonyl-C6H4 2100 CH 3 2-Ethoxy- -Prop-1-en-3-yl carbonyl-C 6 H4 2101 CE 3 2-Ethoxy- (E)-l-Chloroprop--el-3-y 2 carbonyl-CGH4 2102 CE 3 2-Ethoxy- Propyn-3-yl carbonyl-C6H4 2103 CE 3 2-Ethoxy- 3-Methyl-but-2-efl-1-yl carbonyl-C 6 H4 1 04
C
3 3-Ethoxy-
H
0050/44575 No. R 4R 2105 CU 3 3--Ethoxy- CH 3 carbonyl-C 6
H
4 2106 CH 3 3-Ethoxy- C 2
H
carbonyl-C 6
H
4 2107 CU 3 3-Ethoxy- n-C 3
H
7 carbonyl-C6H4 2108 CH 3 3-Ethoxy- i-C 3
H
7 carbonyl-C 6 H4 2109 CU 3 3-Ethoxy- n-C 4
H
9 carbonyl-C 6
H
4 2110 CU 3 3-Ethoxy- t-C 4
H
9 carbonyl-C 6 H4 2111 CU 3 3-Ethoxy- n-C 6
H
1 3 carbonyl-C 6
H
4 2112 CU 3 3-Ethoxy- Prop-1-en-3-yJ.
carbony!L-C 6 H4 2113 CH 3 3-Ethoxy- (E)-1-Chloroprop--el- 3 -y 2 carbonyl-C 6
H
4 2114 CH 3 3-Ethoxy- Propyn-3-yl carbonyl-C 6
H
4 2115 CH 3 3-Ethoxy- 3-Methyl-but-2-el-1-yl carbonyl-C6H4 2116 CU 3 4-Ethoxy-
H
carbony-C6H4 2117 CU 3 4-Ethoxy- CU 3 carbonyl-C 6
H
4 2118 CH 3 4-Ethoxy- C 2
H
carbonyl-C 6 H4 2119 CU 3 4-Ethoxy- n-C 3
H
7 carbonyl-CsUH4 2120 CU 3 4-Ethoxy- i-C 3
H
7 carbonyl-C 6 H4 2121 CU 3 4-Ethoxy- n-C 4
H
9 carbonyl-C6H4 2122 CU 3 4-Ethoxy- t-C 4 H9 carbonyl-C 6 H4 2123 CU 3 4-Ethoxy- n-C 6 HI3 carbonyl-C 6 H4 2124 CU 3 4-Ethoxy- Prop-1-en-3-yJ.
carbonyl-C 6 H4 2125 CU 3 4-.Ethoxy- (E)-1-Chloroprop-1-efl-3-yl carbonyl-C6H4 2126 CU 3 4-Ethoxy- Propyn-3-yl carbonyl-C 6 H4 2127 CU 3 4-Ethoxy- 3-Methyl-but-2-efl-1-yl carbonyl-C 6 H4 0050/44575 No. R 3
R
4
R
SCH
3 2-Amino-
H
carbonyl-C 6
H
4 2129 CH 3 2-Amino- CH 3 carbonyl-C6H 4 2130 CU 3 2-Amino- C 2
H
carbonyl-C 6
H
4 2131 CU 3 2-Amino- n-C 3
H
7 carbonyl-C6H 4 2132 CU 3 2-Amino- i-C 3
H
7 c arbonyl-C 6
H
4 2133 CH 3 2-Amino- n-C 4
H
9 carbonyl-C 6
H
4 2134 CH 3 2-Amnino- t-C 4 H9 carbonyl-C 6
H
4 2135 CU 3 2-Amino- n-C 6
H
1 3 carbonyl-C 6
H
4 2136 CH 3 2-Amino- Prop-1-en-3-yl carbonyl-C 6
H
4 2137 CH 3 2-Amino- 1(E) -1-Chloroprop-1-en-3-yl carbonyl-C 6
H
4 2138 CU 3 2-Amino- Propyn-3-yl carbonyl-C 6 H4 2139 CU 3 2-Amino- 3-Methyl-but-2-en-1-yl carbonyl-C6H 4 2140 CH 3 3-Amino-
H
c arbonyl- C 6 11 4 2141 CF1 3 3-Amino- CH 3 c arbonyl-C 6
H
4 2142 CH 3 3-Amino-
C
2
H
carbonyl-C 6
H
4 2143 CU 3 3-Amino- n-C 3
H
7 carbonyl-C 6
H
4 2144 CU 3 3-Amino- i-C 3
H
7 carbonyl-C6H 4 2145 CU 3 3-Amino- n-C 4
H
9 carbonyl-C 6
H
4 2146 CH 3 3-Amino- t-C 4 Hg carbonyl-C6H 4 2147 CH 3 3-Amnino- n-C 6
H
1 3 carbonyl-C6H 4 2148 CU 3 3-JAmino- Prop-1-en-3-yl carbonyl-C 6
H
4 2149 CU 3 3-Amino- (E)-1-Chloroprop-1-en-3-yl carbony.-C 6
H
4 2150 CU 3 3-Amino- Propyn-3-y- Icarbonyl-C6U4
I
0050/44575 No. R 3 2151 CU 3 3-Amino- 3-Methyl-but-2-en-1-ycarbonyl-C 6
H
4 2152 CH 3 4-Amino- H carbonyl-CGH 4 2153 CU 3 4-Amino- CH 3 carbonyl-C6H4 2154 CU 3 4-Amino- C 2
H
carbonyl-C 6 H4 2155 CU 3 4-Amino- n-C 3
H
7 carbonyl-C 6
H
4 2156 CH 3 4-Amino- i-C 3
H
7 carbonyl-C6H4 2157 CU 3 4-Amino- n-C 4
H
9 carbonyl-C 6
H
4 2158 CH 3 4-Amino- t-C 4
H
9 carbony.-C 6
H
4 2159 CU 3 4-Amino- n-C 6 HI3 carbonyl-C 6
H
4 2160 CU 3 4-Aimino- Prop-l-en-3-yJ.
carbonyl-C 6
H
4 2161 CU 3 4-Amino- (E)-1-Chloroprop-l-en-3-yl carbonyl-C 6 ,4 2162 CU 3 4-Amino- Propyn-3-ycarbonyl-C6H 4 2163 CU 3 4-Amino- 3-Methyl-but-2-en-1-yl carbonyl-C 6
H
4 2164 CU 3 2-(N-Methylamino- H carbonyl.) -C 6
H
4 2165 CU 3 2-(N-Methylamino- CU 3 carbonyl)-C 6 H4 2166 CU 3 2-(N-Methylamino- C 2
H
carbonyl) -C 6
H
4 2167 CU 3 2-(N-Methylamino- n-C 3
U
7 carbonyl) -C 6
U
4 2168 CU 3 2-(N-Methylamino- i-C 3
H
7 carbonyl) -C 6
H
4 2169 CU 3 2-(N-Methylamino- n-C 4
H
9 carbonyJ.) -C 6
U
4 2170 CU 3 2-(N-Methylamino- t-C 4
U
9 carbonyl) -C 6
H
4 2171 CU 3 2-(N-Methylamino- n-C 6
U
1 3 carbonyl )-C 6
U
4 2172 CU 3 2-(N-Methylamino- Prop-1-en-3-yl carbonyl )-C 6
U
4 2173 CU 3 2-(N-Methylamino- (E)-1-Chloroprop-1-en-3-yl carbonyl)-C6H4 0050/44575 No. R 4R 2174 CH 3 2-(ZI-Methylamiflo- Propyri-3-yl carbonyl )-C 6
H
4 2175 CH 3 2-(N-Methylamiflo- 3-Methyl-but-2-el-1-yl carbonyl )-C 6
H
4 2176 CH 3 3-(N-Methylamiflo-
H
carbonyl)-C6H4 2177 CH 3 3-(N-Methylamilo- CH 3 carbonyl )-C 6
H
4 2178 CH 3 3-(N-Methylamnio-
C
2
H
carbonyl) -C 6
H
4 2179 CH 3 3-(N-Methylano- n-C 3
H
7 carbonyl )-C 6
H
4 2180 CH 3 3-(N-Methylanino- i-C 3
H
7 carbonyl )-C 6
H
4 2181 CH 3 3-(N-Methylanino- n-C 4 H9 carbonyl )-C 6
H
4 2182 3-(N-Methylaxnino- t-C 4
H
9 carbonyl.) -C 6
H
4 2183 CH 3 3 -(N-Methyl amino- n-C 6
H
1 3 carbonyl )-C 6
H
4 2184 CH 3 3- (N-Methylarnino- Prop-1-en-3-yl carbony.) -C 6
H
4 2185 CH 3 3-(N-Methylanin2- (E)-1-Chloroprop-l-efl-3-y1 carbonyl)-C 6
H
4 2186 CH 3 3-(N-Methylamino- Propyn-3-yl carbonyl) -C 6
H
4 2187 CH 3 3-(N-Methylamino- 3-Methyl-but-2-el-1-y1 carbonyl )-C 6
H
4 2188 CH 3 4-(N-Methylamilo- H carbony.) -C 6
H
4 2189 CH 3 4-(N-Methylamino- CH 3 carbonyl )-C 6
H
4 2190 CR 3 4-(N-Methylamino- C 2
HS
carbonyl )-C 6
H
4 2191 CH 3 4-(N-Methylamino- n-C 3
H
7 carbonyl)-C 6
H
4 2192 CH 3 4-(N-Methylamino- i-C 3
H
7 carbonyl) -C 6
H
4 2193 CH 3 4-(N-Methylamino- n-C 4
H
9 carbonyl) -C 6
H
4 2194 CH 3 4-(N-Methylamino- t-C 4
H
9 carbonyl )-C 6
H
4 2195 CH 3 4-(N-Methylalnino- n-C 6 Hl 3 carbonyl )-C 6
H
4 216CH 3 4(N-Methylamino- Prop-1-en-3-ycrbonyl )-C 6
H
4 0050/44575 No. R 4R 2197 CU 3 4-(N--Methylamino- (E)-l-Chloroprop-1-en-3-yl carbonyl )-C 6
H
4 2198 CH 3 4-(N-Methylamino- Propyn-3-yl carbonyl )-C 6
U
4 2199 CU 3 4- (N-Methylaznino- 3-Methyl-but-2-el-1-ycarbonyl)-C 6
H
4 2200 CU 3 2-Dimethylamino- H carbonyl-C 6 H4 2201 CU 3 2-Dimethyl amino- CH 3 carbonyl-C 6 U4 2202 CU 3 2-Dimethylamino- C 2
H
carbonyl-C 6
H
4 2203 CE 3 2-Dimethylantino- n-C 3
U
7 carbonyl-C 6 H4 2204 CE 3 2-Dimethylamino- i-C 3
H
7 carbonyl-C 6 H4 2205 CU 3 2-Dimethylamino- n-C 4
H
9 carbonyl-C 6 H4 2206 CU 3 2-Dimethylamino- t-C 4 H9 carbonyl-C 6 U4 2207 CU 3 2-Dimethylamino- n-C 6
HI
3 carbonyl-C 6 H4 2208 CU 3 2-Dimethylamino- Prop-1-en-3-yl carbonyl-C 6 U4 2209 CU 3 2-Dirnethylamino- (E)-1-Chloroprop-1-en-3-yl c arbonyl-C 6 H4 2210 CU 3 2-Dimethylamino- Propyn-3-yl carbonyl-C 6 H4 [2211 CU 3 2-Dimethylamino- 3-Methyl-but-2-efl-1-y1 carbonyl-C 6 2212 CU 3 3-Dimethylamino-
H
carbonyl-C 6 U4 2213 CU 3 3-Dimethylamino- CU 3 carbonyl-C 6 U4 2214 CU 3 3-Dimethylamino-
C
2
U
carbonyl-C 6 H4 2215 CU 3 3-Diniethylamino- n-C 3
U
7 carbony.-C 6
U
4 2216 CU 3 3--Dimethylanfo- i-C 3
U
7 carbonyl-C0U4 2217 CU 3 3-Dimethylamino- n-C 4 Ug carbonyl-C 6 H4 2218 CU 3 3-Dinethylamino- -t-C 4 Ug c arborzly!-C0U4 229CU 3 3-Dimethylamino- n-C 6
U
13 carbonyl-C 6 U4
I
0050/44575 No. R 3 R
R
2220 CH 3 3-Dimethylanino- Prop-l-en-3-yl carbony-CGH4 2221 CH 3 3-Dimethylamino- (E)-l-Chloroprop-1-efl-3-y1 carbonyl-CsR4 2222 CR 3 3-Dimethylamiio- Propyn-3-y.
carbonyl-C 6
H
4 2223 CR 3 3-Dimethylamino- 3-Methyl-but-2-el-1-yJcarbonyl-C6H4 2224 CR 3 4-Dimethylamino-
H
carbonyl-C 6
H
4 2225 CR 3 4-Dimethylamino- CR 3 carbonyl-C 6
H
4 2226 CH 3 4-Dimethylamino- C 2
H
carbonyl-C 6 H4 2227 CH 3 4-Dimethylamino- n-C 3
H
7 carbonyl-C 6 H4 2228 CR 3 4-Dimethylamino- i-C 3
H
7 carboyl-C6H 4 2229 CR 3 4-Dimethylamino- n-C 4 H9 carbonyl-C 6 2230 CR 3 4-Dimethylanino- t--C 4
H
9 carbonyl-C 6 H4 2231. CR 3 4-Dimethylarnino- n-C 6
H
1 3 carbonyl-C 6
H
4 2232 CH 3 4-Dimethylamino- Prop-l-en-3-yl carbonyl-C 6
H
4 2233 CR 3 4-Dimethylamino- (E)-l-Chloroprop-l-el- 3 -Yl carbonyl-C 6 H4 2234 CR 3 4-Dimethylamino- Propyn-3-yl carbonyl-C 6
H
4 2235 CR 3 4-Dimethylamino- 3-Methyl-but-2-el-1-yJl carbonyl-C 6 H4 0oo40/441 The compounds I are suitable as fungicides.
The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes and Basidiomycetes. They are systemically active in some cases 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, c.its, rice, corn, grass, cotton, soybean, coffee, sugar cane, grapes, fruit and decorative plants and vegetable plants such as cucumbers, beans and cucurbits, and on the seeds of these plants.
They are specifically 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 lawns, 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, vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Vertic3llium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.
The compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected from fungal attack with a fungicidally effective amount of the active compounds.
They are applied before or after the infection of the materials, plants or seeds by the fungi.
They can be converted into the.customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; it should in any case guarantee a fine and uniform dispersion the ortho-substituted benzyl ester of a cyclopropanecarboxylic acid [sic]. The formulations are prepared in a known manner, eg. 'y 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 auxiliary substances for this purpose are essentially: solvents such as F V L v
C'
K"
1 0050/44070 91 aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg. methanol, butanol), ketones 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.
The fungicidal compositions in general contain from 0.1 to preferably from 0.5 to 90, by weight of active compound.
Depending on the type of effect desired, the application rates are from 0.01 to 2.0 kg of active compound per ha.
In seed treatment, active compound amounts of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed are in general needed.
The compositions according to the invention can also be present in the application form as fungicides 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 fungicidal spectrum of action is obtained here.
The following list of fungicides with which the compounds according to the invention can be applied together is intended to illustrate the combination possibilities, but not restrict them: sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuram disulfides [sic], 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(l-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl IN2VT 005/4491t9 92 heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, 0,0-diethyl phthalimpidophosphonothioate, 5-amino-i- Ebis (dimethylamino) phosphinyl 3-3-phenyl-1, 2, 4-triazole, 2, 3-dicyano-1, 4-dithicanthraguinone, 2-thio-1, 3-dithiolo[(4,5-b] quinoxaline, methyl 1- (butylcarbamoyl.) -2-benzimidazole carbamate, 2-methoxycarbonylaminobenzimidazole, 2- (fur-2-yl )benzimidazole, 2- (thiazol-4-yl )benzimidazole, N- 2-tetrachloroethylthio) tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide; N-dichlorofluoromethylthio-N' -dimethyl-N-phenylsulf amide, 5-ethoxy-3-trichloromethyl-1, 2, 3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1, 4-dichloro-2, 4- (2-chiorophenyihydrazono )-3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide (sic], 8-hydroxyguinoline or its copper salt, 2, 3-dihydro-5-carboxanilido-6-methyl-1 ,4-oxathiin, 2, 3-dihydro- 5-carboxanilido-6-methyl-1 ,4-oxathiin-4, 4-dioxide, 2-methyl- 6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2, 5-dimethylfuran-3-carboxanilide, 2,4, 3-carboxanilide, N-cyclohexyl-2, 5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2, 5-dimethylf uran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-f ormyl-N1-morpholine-2 2-trichloroethyl acetal, piperazine-1 ,4-diylbis( 2,2, 2-trichloroethyl)formanide [sic], 4-dichloroanilino) -l-formylamino-2, 2, 2-trichloroethane, 2, 6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl] -cis-2, 6-dimethylmorpholine, N-rF3-( p-tert-butylph :iyl 2-methylpropyl Ipiperidine, 2, 4-dichlorophenl -4-ethyl-1, 3-dioxolan-2-ylethylI-ilH-i, 2, 4-triLazole, 1- 4-dichloropheryl )-4-n-propyl-1 ,3-dioxolan-2-ylethyl)-1H-1 ,2,4-triazole, N-(n-propyl)-N-(2, 4, 6-trichiorophenoxyethyl -imidazolylurea, 1- (4-chiorophenoxy) 3-dimethyl-l-( 1H-1, 2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophecx- (2-chlorophenyl (4-chlorophenyl 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyri.midine, bis (pchlorophenyl )-3-pyridinemethanol, 1, 2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1, 2-bis (3-methoxycarbonyl-2-thioureido) benzene, and also various fungicides, such as dodecylguanidine acetate, 3-[E3- 5-dimethyl-2-oxycyclohexyl )-2-hydroxyethyl 3glutarimide, hexachlorobenzene, DL-methyl-N- 6-dimethylphenyl )-N-2-furoyl alaninate, DL-N- 6-dimethylphenyl.) methoxyacetyl) alanine methyl ester, N- 6-dimethylphenyl )-N-chloroacetyl-D, L-2-amino- 0050/445~70 93 butyrolactone, DL-N- 6-dimethylpheiyl (phenylacetyl )alanine methyl ester, 5-methyl-5-vinyl-3- 5-dichiorophenyl 2, 4-dioxo-1 ,3-oxazolidine, 3, 5-dichlorophenyl(-5-methyl-5-methoxymethyl 3-oxazolidine-2, 4-dione (sic), 3- nyl )-l-isopropylcarbamoylhydantoin, N- nyl 2-dimethylcyclopropane-1, 2-dicarboximide, 2-cyano- ethylaminocarbonyl )-2-methoximino) acetarnide [sic), 1-1 2-(2,4-dichlorophenyl)pentyl]-lHi-1 4-triazole, 2,4-difluoro-z- (lH-i, 2, 4-triazolyl-l-methyl )benzhydryl alcohol, N- (3-chloro-2, 6-dinitro-4-trifluoromethylphenyl )-5-trifluoromethyl-3-chloro-2-atuinopyridine, 1- ((bis (4-f luorophenyl )methylsilyl )methyl 2, 4-triazole.
The compounds of the formula I are additionally suitable for controlling pests from the class of insects, arachnids and nematodes effectively. They can be employed as pesticides in plant protection and in the hygiene, stored products protection and veterinary sectors.
The harmful insects include from the order of the butterflies (Lepidoptera), for ezcample, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gernmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoonzia' murinana, Capua reticulana, Cheimatobia bruinata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocanpa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.
006~0 /4 46 t 94 From the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Ainphimallus soistitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorun, Atomaria. linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorun, Bruchus leritis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgif era, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera.
postica, Ip8 typographus, Lema. bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrur oryzophilus, Melanotus communis, Meligethes aeneus, Ilelolontha hippocastani, Melolontha melolontha, Onlema oryzae [sic], Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phylloperthai horticQ:la, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.
From the order of the dipterous insects (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitataj Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophagai Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura. brassicae, Fannia canicularis, Gasjte,,ophilus intestinalis, Glossina morsitans, Haematobia. irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifoii, Lucilia caprina [sic), Lucilia cuprina, Lucilia. sericata, Ijycoria pectoralis, Mayetiola.
destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia. coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.
From the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
From the order of the hymenopterous insects (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta. sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monornorium.
pharaonis, Solenopsis geminata, Solenopsis invicta.
000~0 /44570I From the order of the bed bugs (Heteroptera), for example, Acrosternun hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.
From the order of the plant-sucking insects (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sainbuci, Brachycaudus cardui, IBrevizoryne brassicae, Cerosipha gossypii, Dreyfusia nordinannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacor~huia~ pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolopihium. dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla pini, Rhopalomyz-us ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mnali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorun, Viteus vitifolii.
From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.
From the order of the orthopterous insects (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivsittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus marocc anus, Tachycines asynamorus.
From the class of the Arachnoidea, for example spiders (Acarina) such as Axnblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, 8ryobia praetiosa, Dermacentor silvarun, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.
o00/44570 96 From the class of the nematodes, for example, root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem and leaf eelworms, eg.
Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.
The active compounds can be applied as such or in the form of their formulations or the application forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering compositions or granules by spraying, atomiz- .iig, dusting, scattering or pouring. The application forms depend entirely on the purposes of use; they should in any case as far as possible guarantee the finest dispersion of the active compounds according to the invention.
The active compound concentrations in the ready-for-application preparations can be varied within quite substantial ranges.
In general, they are from 0.0001 to 10 preferably from 0.01 to 1 The active compounds can also be used with great success in ultra-low volume processes (ULV), where it is possible to apply formulations containing more than 95 by weight of active compound or even the active compound without additives.
The application rate of active compound for controlling pests under outdoor conditions is from 0.1 to 2.0, preferably from 0.2 to kg/ha.
For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, and also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, 0050/44S7$ 97 isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water are suitable.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which are suitable for dilution with water.
Suitable surface-active substances are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether. alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.
Powders, scattering compositions and dusts can be prepared by mixing or joint grinding of the active substances with a solid carrier.
The formulations in general contain from 0.01 to 95 by weight, preferably from 0.1 to 90 by weight, of the active compound.
The active compounds are employed here in a purity of from 90 to 100 preferably 95 to 100 (according to NMR spectrum).
Examples of formulations are: I. 5 parts by weight of an active compound are intimately mixed with 95 parts by weight of finely divided kaolin. A dust which contains 5 by weight of the active compound is obtained in this way.
000/44075 98 II. 30 parts by weight of an active compound are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed on the surface of this silica gel. A preparation of the active compound having good adhesion is obtained in this way (active compound content 23 by weight).
III. 10 parts by weight of an active compound are dissolved in a mixture which consists of 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 9 by weight).
IV. 20 parts by weight of an active compound are dissolved in a mixture which consists of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16 by weight).
V. 80 parts by weight of an active compound are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 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 and the mixture is ground in a hammer mill (active compound content 80 by weight).
VI. 90 parts by weight of an active compound are mixed with 10 parts by weight of N-methyl-a-pyrrolidone and a solution is obtained which is suitable for application in the form of very small drops (active compound content 90 by weight).
VII. 20 parts by weight of an active compound are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an 060/4457S 99 aqueous dispersion is obtained which contains 0.02 by weight of the active compound.
VIII. 20 parts by weight of an active compound are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1 by weight of the active compound.
Granules, eg. coated, impregnated and homogeneous granules, can be produced by binding the active compounds to solid carriers.
Solid carriers are eg. mineral earths, such as silica gel, silicic acids, silica gels [sic], silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nut shell meal, cellulose powder and other solid carriers.
Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if appropriate even only immediately before application (tank mix).
These agents can be admixed to the compositions according to the invention in the weight ratio 1:10 10:1.
Synthesis examples The procedures presented in the synthesis examples below were utilized with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are shown in the following tables with physical data.
Synthesis examples [sic] Example 1 Preparation of methyl (E,E)-2-methoxyimino-2-[2'-(l''-methyl, 1''-acetyl)iminooxymethyl]phenylacetate 21 g (0.21 mol) of diacetyl monoxime are added under protective gas and with slight cooling at room temperature to 6.4 g SREAL\7 (0.21 mol) of sodium hydride (80 in 150 ml of dry dimethyl- C:-o I RA4 7V^ O 0050/4457S 100 formamide and the mixture is stirred for 30 min at room temperature. A solution of 60 g (0.21 mol) of methyl 2-methoxyimino-2- (2'bromomiethyl)phenylacetate [sic] in 360 ml of dimethylformamide is then added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10 strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na 2
SO
4 and concentrated. The residue is suspended in a little cold methanol.
After filtering off with suction, 38 g (59 of the title compound are obtained as light brown crystals having a melting point of 69-71°C.
IH-NMR (CDC1 3 1.87(s,3H); 2.30(s,3H); 3.85(s,3H); 4.05(s,3H); 5.15(s,2H); 7.17-7.48(m,4H) ppm.
Example 2 Preparation of methyl (E,E,E)-2-methoxyimino-2-[2'-(l''-methyl, 1'"-(l''-ethoxyiminoethyl))iminooxymethyl]phenylacetate 0.96 g (9.8 mmol) of O-ethylhydroxylamine hydrochloride and 0.6 g of dry molecular sieve beads (3 A) are added to a solution of g (8.2 mmol) of methyl (E,E)-2-methoxyimino-2- [2'-(1''-methyl, 1'"-acetyl)iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is allowed to stand at room temperature for 5 days. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na 2
SO
4 and concentrated. After triturating the residue with n-hexane and filtering off with suction, 1.8 g (63 of the title compound are obtained as pale yellow crystals having a melting point of 69-72 C.
1 H-NMR (CDCl 3 1.27(t,3H); 1.96(s,3H); 1.99(s,3H); 3.84(s,3H); 4.04(s,3H); 4.17(q,2H); 5.06(s,2H); 7.17-7.49(m,4H) ppm Example 3 Preparation of S-methyl (E,E,E)-2-methoxyimino-2-[2'-(l''-methyl, 1"-(1'''-ethoxyiminoethyl))iminooxymethyl]phenylthioacetate g (20 mmol) of methyl (E,E,e)-2-nethoxyimino-2-[2'-(l"methyl, 1"-(1"'-ethoxyiminoethyl))iinooxymethyl]phenyl acetate [sic] are heated at 80°C for 4 hours in 60 ml of 1 M aqueous KOH solution. After cooling, the mixture is extracted with methyl tert-butyl ether, and the aqueous phase is acidified with halfo50/4457S 101 concentrated hydrochloric acid and extracted with methyl tertbutyl ether. After washing the organic phase with water, drying (Na 2
SO
4 and concentrating, 6.0 g of (E,E,E)-2-methoxyimino-2- [2'-(1"-methyl, 1"-(1"'-ethoxyiminoethyl))iminoxymethyl]phenylacetic acid are obtained as a colorless solid which is then dissolved in 100 ml of dry DMF. After addition of 2.9 g (18 mmol of carbonyldiimidazole, the mixture is stirred for 1 hour, and g (36 mmol) of sodium methanethiolate are then added and stirring is continued for 16 hours. The mixture is concentrated, the residue is taken up in methyl tert-butyl ether and water, and the organic phase is extracted with 1 M aqueous NaOH solution, washed with water, dried over ;a 2
SO
4 and concentrated. 4.1 g (57%) of the title compound are thus obtained as a pale yellow oil.
1H-NMR (CDC13); 5 1.27 3H); 1.95 3H); 1.98 3H); 2.33 3H); 4.05 3H); 4.17 2H); 5.03 2H); 7.12-7.48 (m, 4H) ppm.
Table:
R
3
(R
2 n
R
5 ON ON H2 1.1 25R4CH3C R
H
3 CS N CH3 R4
N
No. R 2
R
3
R
4
R
5 Data 1 H CH 3
CH
3
CH
3 Oil; IR (Film): 2935, 1667, 1145, 1057, 1030, 1014, 988, 888, 881, 844, 773 2 H CH 3
CH
3
C
2
H
5 Oil; IR (Film): 2936, 1679, 1386, 1366, 1091, 1047, 1027, 982, 890, 847 Examples of the action against harmful fungi It was possible to show the fungicidal action of the compounds of the general formula I by the following tests: The active compounds were prepared as a 20 strength emulsion in a mixture of 70 by weight of cyclohexanone, 20 by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10 by Sweight of Emulphor® OEL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and correspondingly diluted to the desired concentration with water.
000/44575 102 1. [sic] Erysiphe graminis var. tritici Leaves of wheat seedlings (Kanzler variety) were first treated with the aqueous preparation of the active compounds (containing 63 ppm). After about 24 h, the plants were dusted with spores of powdery mildew of wheat (Erysiphe graminis var. tritici). The plants treated in this way were then incubated for 7 days at 20-22'C and a relative atmospheric humidity of 75-80 The extent of fungal development was then determined.
In this text [sic], the plants treated with the compounds according to the invention showed no attack, the plants treated with a known active compound (compound No. 497, Table 2, EP-A 463 488) showed 40 attack and the untreated plants showed 70 attack.
Examples of the action against animal pests It was possible to show the insecticidal action of the compounds of the general formula I by the following tests: The active compounds were prepared a) as a 0.1 strength solution in acetone or b) as a 10 strength emulsion in a mixture of 70 by weight of cyclohexanol, 20 by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10 by weight of Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and correspondingly diluted to the desired concentration with acetone in the case of a) or with water in the case of b).
After termination of the tests, in each case the lowest concentration was determined at which the compounds still caused an to 100 inhibition or mortality in comparison to untreated control tests (action threshold or minimum concentration).
Claims (11)
1. A phenylacetic acid derivative of the formula I R 5 ON=C(R 4 )-C(R 3 )=NOCHi_ C=NOCH 3 O=C-SR' where the substituents and the index have the following mean- ings: RI is hydrogen or Cl-C 4 -alkyl; R 2 is cyano, nitro, trifluoromethyl, halogen, Cl-C 4 -alkyl or Cl-C 4 -alkoxy; m is 0, 1 or 2, it being possible for the R 2 radicals to be different if m is 2; R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, Cl-C 4 -alkyl, Cl-C 4 -haloalkyl, CI-C 4 -alkoxy, Cl-C 4 -haloalkoxy, Cl-C 4 Clkylthio, C 1 I-C 4 -alkyl amino or di-Cl-C 4 -alkylamino; R 4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, Cl-C 6 -alkyl, Cl-C 6 -alkoxy, Cl-C 6 -alkylthio, Cl-C 6 alkylamino, di-Cl-C 6 -alkylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylthio, C 2 -C 6 -alkenylamino, N-C 2 -C 6 -alkenyl-N-C 1 -C 6 -al kyl amino, C 2 -C 6 -alkynyl, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynylthio, C 2 -C 6 -alkynyl amino, N-C 2 -C 6 alkynyl-N-Cl-C 6 -alkyl amino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkylamninocarbonyl, di-C, -C 6 -alkyl amino- carbonyl, C-C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkyl- aminothiocarbonyl, Cl-C 6 -alkylsulf onyl, CI-C 6 -alkylsulf oxyl, Cl-C 6 -alkoxy, Cl,-C-haloalkoxy, Cl-CG--alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-Cl -C 6 -alkyl amino, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, arylcxy, aryl-Cl-C 4 -alkoxy, arylthio, aryl-Cl-C 4 -alkyl- 0050/44570h 104 thio, hetaryl, hetaryloizy, hetaryJ.-Cl-C 4 -alkoxy, hetarylthio, hetaryl-Cl-C 4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, CI-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkyl amino, d.-,-Cl-C 6 alkyl amino, C-C 6 -alkyl amino- carbonyl, di-Cl-C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothio- carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyioxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(=NOR 6 7 C 3 -C 6 -CYCloalkyl, C 3 -C 6 -cycJloalkoxy, C 3 -C 6 -CYCloalkylthio, C 3 -C 6 -cycloalkyl amino, N-C 3 -C 6 -cycloalkyl-N-C, -C 6 -alkyl amino, C3-C 6 -cycl.oalkernyl, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -CYCloalkenylthio, C 3 -C 6 -cycloalkenyl amino, N-C 3 C 6 -cycloalkenyl-N-C1-C6-' alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-Cl-C 6 -alkylamfino, aryl, aryloxy, arylthio, arylainino, N-aryl-N-Cl-C 6 -alkyl aminlo, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl- N-Cl-C 6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the fol~lowing groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl- 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, C-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylaiio, di-Cl-C 6 -alkyl amino, Cl-C 6 -alkylaminocarbonyl, di-Cl-C 6 -aiiL-'y'-hminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R 5 is hydrogen, Cl-C 1 0 -alkyl, C 3 -C 6 cycloalkyl, C 2 -C 1 0 -alkenyl, C 2 -C 1 0 -alkynyl, C. 1 -Cl-alkylcarbonyl, C 2 -Co-alkenylcarbonyl, C 3 -Clo-alkynylcarbonyl or Cl-C-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, 0000/4437L 105 hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,. aminothiocarbonyl, halogen, Cl-C 6 -alkyl, C 1 -C 6 -haloalkyl, CI-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, CI-CG-alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarboriyl, CI-C 6 -a~kylthio, Cl-C 6 -alkylamino, di-Cl-C 6 -alkylamino, Cl-C 6 -alkylaminocarbonyl, di-Cl-C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothio- carbonyl, C 2 -C-alkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -CYCloalkyl, C 3 -C 6 -c ,.,-loalkoxy, heterocyclyl, hetero- cyclyloxy, benzyl, benzy.Loxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 haloalkoxy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkyl amino, di-C 1 -C 6 -alkylamino, Cl-C 6 -alkylaminocarbonyl, di-C'k-C 6 -alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothio- carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -aikenyloxy, benzyl, benzy-loxy, aryl, aryloxy, ary~thio, hetaryl, hetaryloxy, hetarylthio or C(=NOR 6 )-An-R 7 aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl, Cl-C 6 haloalkyl, Cl-C 6 -alkylcarbonyl, Cl-C 6 -alkylsul fonyl, Cl-C 6 -alkyl sulfoxyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C. 1 -C 6 -alkoxycarbonyl, C-C 6 -alkylthio, Cl-C 6 -alkylamino, di-Cl-C 6 -alkyl amino, Cl-C 6 -alkylamino- carbonyl, di-Cl-C 6 -alkylaminocarbonyl, Cl-C 6 -alkyl amino- thiocarbonyl, di-Cl-C 6 -alkylaminothiocarboflyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NOR 6 7 where A is oxygen, sulfur or nitrogen and where the nitrogen car- ries hydrogen Or. Cl-C 6 -alkyl n is 0 or 1; 00000/ 440~70~ 106 R 6 is hydrogen or Cl-C 6 -alkyl and R 7 is hydrogen or Cl-C 6 -alkyl, and its salts.
2. A compound of the formula I as claimed in claim 1, in which R 3 R 4 and R 5 have the following meanings: R 3 is hydrogen, hydroxyl, cyclopropyl, halogen, Cl-C 4 -alkyl, Cl-C 4 -alkoxy or Cl-C 4 -alkylthio, R 4 is hydrogen, hydroxyl, halogen, cyclopropyl, cyclohexyl, CI-C 4 -alkyl, Cl-C 4 -alkoxy, Cl-C 4 -alkylthio, aryl or hetaryl it being possible for these groups to be partly or completely halogenated or to carry one. to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 alkyl, Cl-CG-haloalkyl, Cl-C 6 -alkylsulfonyl, CI-'C 6 -alkylsulfox:yl, C 3 -CZ 6 -CYCloalkyl, Cl-C 6 -alkoxy, Cl-C 6 haloalkoxy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylanino, di-C 1 -C 6 -alkyl amino, Cl-C 6 -alkylamino- carbonyl, di-Cj-C' -alk~ laminocarbonyl, CI-C 6 -alkylamino- thioca~rbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R 5 is hydrogen, Cl-Cl 0 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 1 0 -alkenyl, C2-C 1 0 -alkynyl C 1 -C 1 0 -alkylcarbonyl, C 2 -C 1 0 -alkenylcarbonyl, C 3 -C 1 0 -alkynylcarbonyl or Cl-Cl 0 -alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amincarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3 -C 6 -CYCloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, C-C 6 -alkylthio, Cl-C 6 -alkylamino, di-CI-C 6 -alkyl amino, Cl-C 6 -alkylaminocarbonyl, di-Cl-C 6 alkylaminocarbonyl Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to 00~0 44575, 107 carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cl-C 6 -alkyl, CI-C 6 -haloalkyl, Cl-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, CI-C 6 -alkoxy, Cl-C 6 -haloalkoxy, Cl-C 6 -alkoxycarbonyl, Cl-C 6 -alkylthio, cl-C-alkylamino, di-Cl-C 6 -alkylainino, Cl-C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaxninocarbonyl,Cl-C 6 -alkylazninothiocarbonyl, di-Cl--C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C =NR 6 7 aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfo- nyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocar- bonyl, halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, CI-C 6 -alkyl- carbonyl, CI-C 6 -alkylsulfonyl, Cl-C 6 -alkylsulfoxyl, C 3 -C 6 -C.'Cloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C 1 -C 6 alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-CG-alkylamino, di-Cl-C 6 -alkyl amino, Cl-C 6 -alkylaminocarbonyl, di-C 1 -C 6 alkylaminocarbonyl, Cl-C 6 -alkylaminothiocarbonyl, di-Cl-C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=N0R 6 )-An-R 7 where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or Cl-C 6 -alkyl; n is 0ori1; R 6 is hydrogen or C 1 -CG-alkyl and R 7 is hydrogen or Cl-C 6 -alkyl, and its salts.
3. A compound of the formula I as claimed in claim 1, in which m is 0.
4. A compound of the formula I as claimed in claim 1, in which R 1 i s anX[. 0050/44S75 108 A process for preparing the compounds of the formula I as claimed in claim 1, in which R 3 is not halogen, which com- prises reacting a benzyl derivative of the formula II 0 (R2)m Ll-CH 2 9 II C=NOCH3 O=C-SR 1 in which L 1 is a nucleophilically replaceable leaving group, in a manner known per se with a hydroxyimine of the formula III R 5 ON=C(R 4 )-C(R 3 )=NOH III
6. A process for preparing the compounds of the formula I as claimed in claim 1, in which R 3 and R 4 are not halogen, which comprises reacting a benzyl derivative of the formula II as in claim 5 in a manner known per se with a dihydroxyimine of the formula IV HON=C(R 4 )-C(R 3 )=NOH IV to give a compound of the formula V [(R 2 m HON=C(R4)-C(R3)=NOCH 2 C=NOCH 3 O=C-SR 1 and then reacting V with a compound of the formula VI R 5 -L 2 VI where L 2 is a nucleophilically replaceable leaving group, to give I.
7. A process for preparing the compounds of the formula I as claimed in claim 1, in which R 3 is not halogen, which com- prises reacting a benzyl derivative of the formula II as in 0050/44075 109 claim 5 in a manner known per se with a carbonylhydroxyimine of the formula VIIa O=C(R 4 )-C(R 3 )=NOH VIIa to give a compound of the formula VIII (R 2 )m O=C(R 4 )-C(R 3 VIII O=C-SR 1 then either reacting VIII a) first with hydroxylamine or its salt and then with a com- pound of the formula VI (RS-L 2 as in claim 6 or b) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb R 5 -ONH 2 IXa R5-ONH 3 0 D@ IX) where Q is the anion of an acid, to give I.
8. A composition against animal pests or harmful fungi, coyachknai customary additives and an effective amount of a compound of the formula I as claimed in claim 1.
9. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environ- ment or the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I as claimed in claim 1. ns* I l i- 1- z t~-ftt--on I--=~mpes*i; aQ- c arz.:i::t. Z
11. i inXa Prrfu aim1 ezt gl. rqzka-~ 12I~ests Cr~ 110 A method of production of compositions against animal pests or harmful fungi comprising forming a composition containing customary additives and an effective amount of a compound of the formula I as claimed in claim 1. 11. A compound of the formula VIII as in claim 7.
12. A method of production of compositions against animal pests or harmful fungi comprising a reaction sequence in which a compound of formula VIII is an intermediate. DATED this 6th day of October, 1997 BASF AKTIENGESELLSCAFT WATERMARK PATENT TRADEMARK ATTORNEYS 4TH FLOOR "DURACK CENTRE" 263 ADELAIDE TERRACE PERTH W.A. 6000 AUSTRALIA 0050/44575 Phenylacetic acid derivatives, preparation thereof and intermedi- ates theref or, and compositions containing them Abstract Phenylacetic acid derivatives of the formula I R5ON=C(R4)-C(R3)=NOCHi_(R) C=NOCH 3 O=C-SR 1 where the substituents and the index have the following meanings: R 1 is hydrogen or alkyl; R 2 is cyano, nitro, trifluoromethyl, halogen, alkyl or alkoxy;, m is 0, 1 or 2, it being possible for the R 2 radicals to be different if m is 2; R 3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino or dialkylamino; R 4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylauino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkynyl, alkynyloxy, alkynylthio, alkynylamino, N-alkynyl-N-alkylamino; unsubstituted or substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alky'lamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalken- ylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, hetero- cyclyloxy, heterocyclylthio, heterocyclylamino, N-hetero- cyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-alkylamino; R 5 is hydrogen, 0050/40S75 unsubstituted or subotituted alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl or alkylsulfonyl,; unsubstituted or substituted aryl, arylcarbonyl, aryl- sulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, and their salts, processes and intermediates for their prepara- tion, and their use are described. 'ZO A OJ INTEtNATIONAL SEARC REPORT t Apo No PCT/EP 95/00014 A. CLASSIFICATION OP SURJEC MATTER IPC 6 C07C327/04 C07C327/22 A01N37/00 According to Internaonal Patent Classification (IPC) or to both national cleasification and IPC B. FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) IPC 6 C07C A01N 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 practical, 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. Y EP,A,0 432 503 (BASF AG) 19 June 1991 1-13 cited in the application see claims 1-8 see page 144, line 31 page 147, line Y WO,A,90 07493 (F.HOFFMANN-LA ROCHE) 12 1-13 July 1990 Seite 23: Beispiel see claims 1-15 A EP,A,0 463 488 (BASF AG) 2 January 1992 1-13 cited in the application see page 137, line 39 page 142, line 56 see claims 1-10 Further documents are listed in td1 continuation of box C. El Patent family members are listed in annex. Special categories of cated documents later document published after the international filing date or priority date and not in conflict with the application but Sdocumentdefining the general state of the art which is not cid to understand the principle or theory undeying the considered to be of particular relevance invention earlier document but published on or after the international document of particular relevance; the claimed invention filing date cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or involve an inventive step when the document is taken alone which is cited to establish the pulblication date of another document of particular relevance the claimed invention citation or ther special reason (as specified) canot be considered to involve an inventive step when the document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled document published prior to the intemational filing date but in the art. later than the priority date claimed document member of the same patent family Date of the actual completion of the intenational search Date of mailing of the international search report 28 April 1995 18. 05. Name and mailing address of the ISA Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 NL 2280 HV Riiswijk Tel. 31-70) 340.2040, Tx. 31 G51 epo n, Goet, Fax: 31-70) 340-3016 t Il Form PCT/ISA/210 (iecsnd sheet) (July 1I92) WAtq~lP~ No JNITEILNATONAL SEA"Cf RMPORT PCT/AP 95/00014 Patent document Publication Patent family Publication cited in search report date member(s) due EP-A-0432503 19-06-9 1 DE-A- 3938054 23-05-91 DE-A- 4029092 19-03-92 AU-B- 634599 25-02-93 AU-A- 6662290 14-11-91 CA-A- 2030069 17-05-91 *DE-O- 59004331 03-03-94 ES-T- 2062268 16-12-94 JP-A- 3206075 09-09-91 *US-A- 5112860 12-05-92 US-A- 5187170 16-02-93 WO-A-9007493 12-07-90 AT-T- 117983 15-02-95 AU-A- 4639089 01-08-90 CA-A- 2005345 29-06-90 DE-D- 58908972 16-03-95 EP-A- 0403618 27-12-90 ES-T- 2067570 01-04-95 JP-T- 3503056 11-07-91 NO-C- 173543 29-12-9 EP-A-0463488 02-01-92 DE-A- 4020384 02-01-92 DE-A- 4020388 02-01-92 AU-B- 652159 18-08-94 AU-A- 7929691 28-01-93 CA-A- 2045725 28-12-91 HU-B- 209642 28-09-94 JP-A- 4261147 17-09-92 NZ-A- 238714 26-07-94 US-A- 5387607 07-02-95 US-A- 5194662 16-03-93 US-A- 5292759 08-03-94 Form PCT/ISA/210 (patent fLmilY annex) (JuIy 1992) INIVMNA'fl0NALMJ IMCUMECI IENIMI CWET PCT/EP 95/00014 A. KLASSIPIZIERUNG DES ANMELDUNOSG8IGHNSTANDIIS IPK 6 C07C327/04 C07C327/22 A01N37/00 Nach der Internationalen, PatcntkIassikation (IPK) oder nach der nabonalen Klassifikation und der IPK 0. RECHERCIERTE GEIIIETE Recherchicrter Mindestprftfstoff (K asiflkationssystemn und Klasfkatonsymbole) IPK 6 C07C AOIN Recherchierte aber niche zumn Mindestpriifstoff gchilrende Veroffentlichungen, soweit diese unter die recherchierten Gebiete fallen Wiihrend der internationalen Recherche konsultierte cecktronische Datenbank (Name der Datcnbanc und evi. verwendete Suchbegrsffe) C. ALS WESENTLICH- ANGESEHENE UNTERLAGEN__________ Kategorice Bezeichnung dcr Ver~fentlichung, sowett crforderlieb tinter Angabe der in Betracht kommendcn Teile Mrt. Anspruch Nr. Y EP,A,O 432 503 (BASF AG) 19. Juni 1991 1-13 in der Anmeldung erwahnt siehe AnsprUche 1-8 siehe Seite 144, Zeile 31 Seite 147, Zeile Y WO,A,90 07493 (FHOFFMANN-LA ROCHE) 12. 1-13 ~Juli 1990 Seite 23: Beispiel siehe Anspriiche 1-15 A EP)A,0 463 488 (BASF AG) 2. Januar 1992 1-13 in der Annieldung erwihnt siehe Seite 137, Zeile 39 Seite 142) Zeile 56 siehe AnsprUche 1-10 [J Weitere Verldffcntlichungen Sind der Fortaclzung Von Feld C zu MV Slale Anhang Patentfaillie entnehmen J *Besondere Kategorieni von angegebenen Verofentlichungen 'T Sptre Ver~fentlichung, dic nach dem internzlionalen Anmededatumn A' Verdffentiichung, die den all gemeinen Stand der Tcimik definiert, ode dem Priorititsdatum ver~ffentliht worden ist und mit der aber nlcht alsb bonders bcdeutsam anzuschen 1st Anineldung nicht kollidicit, sondem, ntis zumVcrstindnis des der 1lteres Dolimesst, das jedoch erst am oder nAch dem Intemnationalen TErfidngzgelige den Prnp de e hrzgudelgn Anmeldedatuxn vew~ffentlieht wordtn is *X Vcr~fentlichung von besonderer Bcdeutung; die beanspnschte Erfindug WL Ver~ffentlichung, dit geeignet ist. cinen Priorit~tsnspruch zweifclhaft er- kann allcin aul'lrnd dieser VerMendichung nieht ala neu Oder auf scheinen zu lassen, oder urch die das Vcr~ffenichungsdatum esner errindcrischer Tiligkelt benshlend betraciflet werden anderen im Recherchcnbcricht genannten Ver~ffentlichting belcgt werden Ver~fentlichung von besonderer Bedcuwung die beanspruchte Edindunj soil oder die aus cinemn anderen bevonderen Grund angegeben ist (Wi kann nicht als auf eriindcriseher Titilikeit beruhend betrachtet Ausgcfwlht) werden, wcnn die Vcrdlrentlichung mut einer oder mebrerent anderen 0' Verdffentfichung, die sich auf cine mdndliche Offcnbarting, Verdffentlichungen dieser Kategone in Verbindung gebraclfl wird und eine Berwtzung, cisie Atiastellung Oder andere Mallnahmen bezieht diese Vertuindung fOr ainen.Fachmarn nAheliegend tst 'P Vecr~fentlichung, die yor dem Internationalen Annieldedatum, aber nach Ver~el~ctfchung, die WOWlie derselben Patentfamilie ist demn beanspruehten Prionitlitdaturm ver~ffenllcht worden ist Datum des Absehlusses der intemationalc n Recherche Absendedatum, des internationalen Recherchenberiehts
28. April1 1995 18. 05. Name und Postnschrift der' Internationale ReeherchenbehOrde BevollrnIchtigter Bediensteter Puropilse Patentamnt, P.0, S8 18 Patentlaan 2 NL 2280 HV ijswijk Tel.(+ 3170) 340-2040, Tx 31651epo rd, G ez Faxc 31.70) 340-3016 Gez Fornblatt PCT/ISA12IB (Illatt 2) (lull 1992) INRNTINLAR*M ONRIU PCT/EP 95/00014 mRecherchenbericlfl Datum drMitglicdQr derDaudr angefites Patentdakcument V~~fnichung Pcnfmlie Vor8ffentlichung EP-A-0432503 19-06-91 DE-A- 3938054 23-05-91 DE-A- 4029092 19-03-92 AU-B- 634599 25-02-93 AU-A- 6662290 14-11-91 CA-A- 2030069 17-05-91 OE-D- 59004331 03-03-94 ES-T- 2062268 16-12-94 JP-A- 3206075 09-09-91 US-A- 5112860 12-05-92 US-A- 5187170 16-02-93 WO-A-9007493 12-07-90 AT-T- 117983 15-02-95 AU-A- 4639089 01-08-90 CA-A- 2005345 29-06-90 DE-D- 58908972 16-03-95 EP-A- 0403618 27-12-90 ES-T- 2067570 01-04-95 JP-T- 3503056 11-07-91 NO-C- 173543 29-12-93 EP-A-0463488 02-01-92 OE-A- 4020384 02-01-92 DE-A- 4020388 02-01-92 AU-B- 652159 18-08-94 AU-A- 7929691 28-01-93 CA-A- 2045725 28-12-91 HU-B- 209642 28-09-94 JP-A- 4261147 17-09-92 HZ-A- 238714 26-07-94 US-A- 5387607 07-02-95 US-A- 5194662 16-03-93 US-A- 5292759 08-03-94 Formblatt PCr/13N1210 (Anhang PAtantftIiUuII 1992) I
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4403446 | 1994-02-04 | ||
| DE4403446 | 1994-02-04 | ||
| DE4421181 | 1994-06-17 | ||
| DE4421181 | 1994-06-17 | ||
| PCT/EP1995/000014 WO1995021156A1 (en) | 1994-02-04 | 1995-01-03 | Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1454795A AU1454795A (en) | 1995-08-21 |
| AU686304B2 true AU686304B2 (en) | 1998-02-05 |
Family
ID=25933550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU14547/95A Expired - Fee Related AU686304B2 (en) | 1994-02-04 | 1995-01-03 | Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0741698A1 (en) |
| JP (1) | JPH09508396A (en) |
| CN (1) | CN1143361A (en) |
| AU (1) | AU686304B2 (en) |
| BR (1) | BR9506718A (en) |
| CA (1) | CA2182406A1 (en) |
| CZ (1) | CZ231796A3 (en) |
| HU (1) | HUT76523A (en) |
| IL (1) | IL112480A0 (en) |
| MX (1) | MX9603175A (en) |
| NZ (1) | NZ278588A (en) |
| SK (1) | SK102296A3 (en) |
| WO (1) | WO1995021156A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE201196T1 (en) * | 1995-04-08 | 2001-06-15 | Basf Ag | METHOD FOR PRODUCING LARGE ISOMERIC PURE ALPHA-BISOXIMES |
| AU6742196A (en) * | 1995-08-15 | 1997-03-12 | Novartis Ag | Pesticidal indazole derivatives |
| AR004012A1 (en) | 1995-10-10 | 1998-09-30 | Basf Ag | DERIVATIVES OF PHENYLACETIC ACID, PROCEDURES FOR ITS OBTAINING, ITS USE TO PREPARE COMPOUNDS TO FIGHT ANIMALS OR HARMFUL FUNGI, THE COMPOSITIONS SO OBTAINED AND THE PROCEDURES FOR THE APPLICATION OF SUCH COMPOSITIONS. |
| JPH11514632A (en) * | 1995-11-02 | 1999-12-14 | ビーエーエスエフ アクチェンゲゼルシャフト | Pyridylacetic acid derivative, method for producing the same, intermediate for the production, and use thereof |
| AU717468B2 (en) | 1995-12-07 | 2000-03-30 | Bayer Aktiengesellschaft | Process for the preparation of pesticides |
| PL185913B1 (en) | 1995-12-07 | 2003-08-29 | Bayer Ag | Pesticides |
| AU2178697A (en) * | 1996-04-11 | 1997-10-29 | Shionogi & Co., Ltd. | Alpha-alkoxyiminobenzyl derivatives and agricultural chemicals containing them as active ingredients |
| CO5050364A1 (en) | 1997-05-28 | 2001-06-27 | Basf Ag | METHOD TO CONTROL HARMFUL FUNGES |
| US6313344B1 (en) | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007493A1 (en) * | 1988-12-29 | 1990-07-12 | F. Hoffmann-La Roche Ag | Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them |
| US5112860A (en) * | 1989-11-16 | 1992-05-12 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
| US5187170A (en) * | 1989-11-16 | 1993-02-16 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59108900D1 (en) * | 1990-06-27 | 1998-01-22 | Basf Ag | O-benzyl oxime ether and crop protection agents containing these compounds |
-
1995
- 1995-01-03 AU AU14547/95A patent/AU686304B2/en not_active Expired - Fee Related
- 1995-01-03 HU HU9602154A patent/HUT76523A/en unknown
- 1995-01-03 CN CN95191959.8A patent/CN1143361A/en active Pending
- 1995-01-03 SK SK1022-96A patent/SK102296A3/en unknown
- 1995-01-03 CA CA002182406A patent/CA2182406A1/en not_active Abandoned
- 1995-01-03 MX MX9603175A patent/MX9603175A/en not_active Application Discontinuation
- 1995-01-03 JP JP7520336A patent/JPH09508396A/en active Pending
- 1995-01-03 NZ NZ278588A patent/NZ278588A/en unknown
- 1995-01-03 EP EP95906289A patent/EP0741698A1/en not_active Withdrawn
- 1995-01-03 WO PCT/EP1995/000014 patent/WO1995021156A1/en not_active Application Discontinuation
- 1995-01-03 CZ CZ962317A patent/CZ231796A3/en unknown
- 1995-01-03 BR BR9506718A patent/BR9506718A/en not_active Application Discontinuation
- 1995-01-30 IL IL11248095A patent/IL112480A0/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007493A1 (en) * | 1988-12-29 | 1990-07-12 | F. Hoffmann-La Roche Ag | Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them |
| US5112860A (en) * | 1989-11-16 | 1992-05-12 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
| US5187170A (en) * | 1989-11-16 | 1993-02-16 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| SK102296A3 (en) | 1997-04-09 |
| HUT76523A (en) | 1997-09-29 |
| EP0741698A1 (en) | 1996-11-13 |
| WO1995021156A1 (en) | 1995-08-10 |
| CN1143361A (en) | 1997-02-19 |
| CA2182406A1 (en) | 1995-08-10 |
| BR9506718A (en) | 1997-09-23 |
| IL112480A0 (en) | 1995-03-30 |
| MX9603175A (en) | 1997-04-30 |
| CZ231796A3 (en) | 1997-02-12 |
| AU1454795A (en) | 1995-08-21 |
| JPH09508396A (en) | 1997-08-26 |
| NZ278588A (en) | 1997-04-24 |
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