# Patent

## Title
Herbicidally active 4-(3-alkylsulfinylbenzoyl)pyrazoles

## Abstract

4-(3-Alkylsulfinylbenzoyl)pyrazoles of the formula (I) are described as herbicides.




In this formula (I), R1 to R4, X and Y are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.

## Background
CROSS REFERENCE TO RELATED APPLICATIONS
This application claims priority to European Application No. 08009758.7 filed May 29, 2008, the entire contents of which are incorporated by reference.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to the technical field of the herbicides, in particular to that of the herbicides for the selective control of broad-leafed leaves and grass weeds in crops of useful plants.
2. Description of Related Art
It has already been disclosed in various publications that certain 4-benzoylpyrazoles substituted by sulfur-containing radicals in the 3-position of the phenyl ring have herbicidal properties. Thus, EP 0 352 543 and WO 97/41106 mentions benzoylpyrazoles which may be substituted at the phenyl ring inter alia by an alkylsulfinyl radical. WO 00/03993 and WO 2008/151719 disclose inter alia 3-cyclopropyl-4-(3-alkylsulfinyl benzoyl)pyrazoles.
However, the compounds known from these publications frequently do not display a sufficient herbicidal activity. It is therefore an object of the present invention to provide alternative herbicidally active compounds.
SUMMARY OF THE INVENTION
It has now been found that certain 4-benzoylpyrazoles whose phenyl ring carries an alkylsulfinyl radical in the 3-position are especially suitable as herbicides.
The present invention relates to 4-(3-alkylsulfinylbenzoyl)pyrazoles of the formula (I) or their salts




in which

    R1 is (C1-C4)-alkyl,
    R2 is hydrogen or (C1-C4)-alkyl,
    R3 is (C1-C6)-alkyl,
    R4 is hydrogen, (C1-C6)-alkylsulfonyl, (C1-C4)-alkoxy-(C1-C6)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C1-C6)-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy,
    X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C6)-cycloalkyl, OR5, OCOR5, OSO2R5, S(O)nR5, SO2OR5, SO2N(R5)2, NR5SO2R5, NR5COR5, (C1-C6)-alkyl-S(O)nR5, (C1-C6)-alkyl-OR5, (C1-C6)-alkyl-OCOR5, (C1-C6)-alkyl-OSO2R5, (C1-C6)-alkyl-SO2OR5, (C1-C6)-alkyl-SO2N(R5)2 or (C1-C6)-alkyl-NR5COR5;
    Y is fluorine, chlorine, bromine, iodine, nitro or the group SO2R7,
    R5 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, phenyl or phenyl-(C1-C6)-alkyl, where the six last-mentioned radicals are substituted by s radicals from the group consisting of hydroxy, mercapto, amino, cyano, nitro, thiocyanato, OR6, SR6, N(R6)2, NOR6, OCOR6, SCOR6, NR6COR6, CO2R6, COSR6, CON(R6)2, (C1-C4)-alkyliminooxy, (C1-C4)-alkylcarbonyl, (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl and (C1-C4)-alkylsulfonyl;
    R6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl,
    R7 is (C1-C4)-alkyl,
    m is 0, 1, 2, 3, 4 or 5,
    n is 0, 1 or 2,
    s is 0, 1, 2 or 3.


In formula (I) and all formulae given below, alkyl radicals which have more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.
If a group is polysubstituted by radicals, this is to be understood as meaning that this group is substituted by one or more of the abovementioned radicals which are identical or different.
Owing to the center of chirality of the sulfinyl group, the compounds of the formula (I) are present as enantiomers. In addition, depending on the nature of the substituents and on how they are attached, there may be further stereoisomers, for example in the case of asymmetrically substituted carbon atoms. Stereoisomers, if not already obtained in pure form in the synthesis, can be obtained from the mixtures generated in the course of the preparation using customary separation methods, for example by chromatographic separation methods. Equally, stereoisomers can be prepared selectively using stereoselective reactions and employing optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and their mixtures which are embraced by the formula (I), but are not specifically defined.
Preference is given to compounds of the formula (I) in which

    R1 is methyl, ethyl, n-propyl or isopropyl,
    R2 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
    R3 is (C1-C4)-alkyl,
    R4 is hydrogen, (C1-C3)-alkylsulfonyl, (C1-C2)-alkoxy-(C1-C4)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C1-C6)-alkyl or benzyl, each of which is substituted by m methyl groups,
    X is nitro, halogen, (C1-C4)-alkyl, trifluoromethyl, (C1-C4)-alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonyl methyl, methylsulfonylethoxymethyl, methoxyethylsulfonyl methyl, methylsulfonylethylsulfonylmethyl,
    Y is fluorine, chlorine, bromine, iodine or the group SO2R7,
    R7 is methyl, ethyl, n-propyl or isopropyl,
    m is 0, 1, 2 or 3.


Particular preference is given to compounds of the formula (I) in which

    R1 is methyl or ethyl,
    R2 is hydrogen, methyl or ethyl,
    R3 is methyl, ethyl, n-propyl or isopropyl,
    R4 is hydrogen,
    X is nitro, halogen, (C1-C4)-alkyl, trifluoromethyl, (C1-C4)-alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonyl methyl, methylsulfonylethoxymethyl, methoxyethylsulfonyl methyl, methylsulfonylethylsulfonylmethyl,
    Y is fluorine, chlorine, bromine, iodine or the group SO2R7,
    R7 is methyl or ethyl.




DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
Unless otherwise defined, the substituents and symbols in all the formulae mentioned hereinbelow have the same meaning as described in formula (I).
Compounds according to the invention in which R4 is hydrogen can be prepared, for example, by the process shown in Scheme 1 and known from WO2005/122768 by reacting a benzoic acid of the formula (II) with a pyrazole of the formula (III) in the presence of a condensing agent such as N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, followed by cyanide-catalyzed rearrangement.




Compounds of the formula (I) can be prepared, for example, by the process shown in Scheme 2 and described in WO2005/122768 by reacting a compound of the formula (Ia) with compounds of the formula (IV) in which E is a nucleophilic leaving group.




Compounds according to the invention in which R4 is hydrogen can also be prepared, for example, by the process shown in Scheme 3 by nucleophilic aromatic substitution from compounds of the formula (V) in which L2 is, for example, a fluorine or chlorine atom using a thiolate (VI) in which M is a metal cation, followed by oxidation.




Compounds of the formula (II) can be prepared, for example, by the process shown in Scheme 4 from benzoic acids of the formula (VII) by introducing the substituent X, followed by nucleophilic aromatic substitution and then oxidation. Suitable reactions for introducing the substituent X are known, for example, from J. Chem. Soc. Perkin Trans. 1 1995, p. 1265 ff, J. Heterocyclic Chem. 1999, 36, p. 1453 ff., Angew. Chem. 2005, 117, 380-398, J. Org. Chem. 2003, 68, 2030-2033 and J. Org. Chem. 1994, 59, 4042-4044.




Compounds of the formula (II) are novel and also form part of the subject matter of the present invention.
Collections of compounds of the formula (I) and/or their salts which can be synthesized in accordance with the abovementioned reactions can also be prepared in a parallelized manner, which can be effected manually or in a partly or fully automated manner. Here, it is possible for example to automate the procedure of the reaction, the work-up or the purification of the products or intermediates. In total, this is understood as meaning a procedure as described for example by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Gunther Jung), Wiley 1999, on pages 1 to 34.
A series of commercially available apparatuses can be used for the parallelized reaction procedure and work-up, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Mass. 02451, USA. Chromatographic apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA, are available, inter alia, for the parallelized purification of compounds of the formula (I) and their salts or of intermediates generated in the course of the preparation.
The apparatuses listed lead to a modular procedure in which the individual passes are automated, but manual operations must be carried out between the passes. This can be circumvented by the use of partly or fully integrated automation systems, where the relevant automation modules are operated by, for example, robots. Such automation systems can be obtained for example from Caliper, Hopkinton, Mass. 01748, USA.
The performance of individual, or a plurality of, synthesis steps can be aided by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Besides the methods described herein, the preparation of compounds of the formula (I) and their salts can be effected fully or in part by solid-phase-supported methods. For this purpose, individual intermediates, or all intermediates, of the synthesis or of a synthesis adapted to the relevant procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described sufficiently in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Gunther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a series of protocols known from the literature, which, again, can be carried out manually or in an automated manner. For example, the reactions can be carried out by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.
Carrying out individual or a plurality of synthesis steps, both on a solid and in the liquid phase, can be aided by the use of microwave technology. A series of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (Editors C. O. Kappe and A. Stadler), Wiley, 2005.
The preparation in accordance with the processes described herein generates compounds of the formula (I) and their salts in the form of substance collections, which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I) and their salts.
The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow together referred to as “compounds according to the invention”, have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active substances also act efficiently on perennial harmful plants which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control.
The present invention therefore also relates to a method of controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-planting (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Examples of individual representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention shall be mentioned, without the mention being intended as a limitation to certain species.
Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. 
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. 
If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop their growth and, finally, die completely after three to four weeks have elapsed.
When the active substances are applied post-emergence to the green plant parts, growth stops after the treatment, and the harmful plants remain in the growth stage of the time of application or die fully after a certain period of time, so that competition by weeds, which is harmful to the crop plants, is thus eliminated at an early point in time and in a sustained manner.
Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of undesired plant growth in plant crops such as agriculturally useful plants or ornamentals.
Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plant metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting undesired vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.
Owing to their herbicidal and plant-growth-regulatory properties, the active substances can also be employed for controlling harmful plants in crops of genetically modified plants or plants which have been modified by conventional mutagenesis. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate for example to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants with an increased starch content or a modified starch quality or those with a different fatty acid composition of the harvested material are known.
It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum and millet, rice, cassaya and maize or else crops of sugar beet, cotton, soybean, oil seed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.
Conventional ways of generating novel plants which, in comparison with existing plants, have modified properties are, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

    
    
        recombinant modifications of crop plants for the purposes of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),
        transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf., for example, EP-A-0242236, EP-A-242246) or of the glyphosate type (WO 92/00377) or of the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),
        transgenic crop plants, for example cotton, which is capable of producing Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259),
        transgenic crop plants with a modified fatty acid composition (WO 91/13972),
        genetically modified crop plants with novel constituents or secondary metabolites, for example novel phytoalexins, which bring about an increased disease resistance (EPA 309862, EPA0464461),
        genetically modified plants with reduced photorespiration which feature higher yields and higher stress tolerance (EPA 0305398),
        transgenic crop plants which produce pharmaceutically or diagnostically important proteins (“molecular pharming”),
        transgenic crop plants which are distinguished by higher yields or better quality,
        transgenic crop plants which are distinguished by a combination, for example of the abovementioned novel properties (“gene stacking”).
    
    


A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431).
To carry out such recombinant manipulations, it is possible to introduce nucleic acid molecules into plasmids, which permit a mutagenesis or sequence modification by recombination of DNA sequences. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments with one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone”, VCH Weinheim 2nd ed., 1996
The generation of plant cells with a reduced activity for a gene product can be achieved for example by the expression of at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by the expression of at least one correspondingly constructed ribozyme, which specifically cleaves transcripts of the abovementioned gene product. To do this, it is possible firstly to use DNA molecules which comprise all of the coding sequence of a gene product, including any flanking sequences which may be present, or else DNA molecules which only comprise parts of the coding sequence, it being necessary for these parts to be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology with the coding sequences of a gene product, but which are not entirely identical.
When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any compartment of the plant cell. In order to achieve localization in a particular compartment, however, it is possible for example to link the coding region to DNA sequences which ensure the localization in a specific compartment. Such sequences are known to the skilled worker (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.
The transgenic plant cells can be regenerated by known techniques to give intact plants. In principle, the transgenic plants may be plants of any plant species, that is to say both monocotyledonous and dicotyledonous plants.
Thus, transgenic plants can be obtained which feature modified properties as the result of overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.
It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active substances.
When the active substances according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants.
The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
The compounds according to the invention can be employed in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to herbicidal and plant-growth-regulating compositions which comprise the compounds according to the invention.
The compounds according to the invention can be formulated in various ways, depending on the prevailing biological and/or physico-chemical parameters. Examples of possible formulations are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for application by broadcasting and on the soil, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.
Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.
Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetters, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance. To prepare the wettable powders, the herbicidally active substances are ground finely, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and mixed with the formulation auxiliaries, either simultaneously or subsequently.
Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters such as, for example, sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as, for example, polyoxyethylene sorbitan fatty acid esters.
Dusts are obtained by grinding the active substance with finely divided solid materials such as, for example, talcum, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be water- or oil-based. They can be prepared for example by wet-grinding by means of commercially available bead mills, if appropriate with addition of surfactants as already listed above for example in the case of the other formulation types.
Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, as have already been mentioned for example above for the other formulation types.
Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material, or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of stickers, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is customary for the production of fertilizer granules, if desired as a mixture with fertilizers.
Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed stirrers, and extrusion without solid inert material.
To prepare disk granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 et seq.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.
For further details of the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
As a rule, the agrochemical preparations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration can amount to approximately 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active substance, preferably in most cases from 5 to 20% by weight of active substance, and sprayable solutions comprise approximately from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers and the like which are being used. In the case of the water-dispersible granules, for example, the active substance content is between 1 and 95% by weight, preferably between 10 and 80% by weight.
In addition, the active substance formulations mentioned comprise, if appropriate, the auxiliaries which are conventional in each case, such as stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors, and pH and viscosity regulators.
Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.
Active substances which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by a chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. In this context, one and in some cases also several use forms are mentioned by way of example:
acetochlor, acibenzolar, acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, methazole, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogen sulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione, sulf-allate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, TH-547, thenylchlor, thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds




For use, the formulations, which are present in commercially available form, if appropriate, are diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for broadcasting, and sprayable solutions, are usually not diluted further with further inert substances prior to use.
The application rate required of the compounds of the formula (I) varies as a function of the external conditions such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha and more of active substance, but it is preferably between 0.005 and 750 g/ha.
The examples which follow are intended to illustrate the invention.
A. CHEMICAL EXAMPLES
1. Preparation of 4-(4-chloro-3-ethylsulfinyl-2-methyl benzoyl)-5-hydroxy-1,3-dimethylpyrazole (No. 3-238 of Table 3)
Step 1: Synthesis of methyl 4-chloro-3-(dimethylaminothiocarbonyloxy)-2-methylbenzoate
Under an atmosphere of nitrogen, 12.3 g (109.7 mmol) of 1,4-diazabicyclo[2.2.2]octane and then 13.6 g (109.7 mmol) of dimethylaminothiocarbonyl chloride were added to 11.0 g (54.8 mmol) of methyl 4-chloro-3-hydroxy-2-methylbenzoate in 200 ml of N,N-dimethylformamide. The mixture was stirred at room temperature (RT) for 16 h and, for work-up, poured on ice-water. The product precipitated out and was removed by filtration. The residue was washed with 1M HCl. This gave 14.7 g of clean product.
Step 2: Synthesis of methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate
Under an atmosphere of nitrogen, 12.1 g (42.0 mmol) of methyl 4-chloro-3-(dimethylaminothiocarbonyloxy)-2-methylbenzoate in 30 ml of 1,3-dimethoxybenzene were heated at 220° C. for 6 h. For work-up, the reaction mixture was cooled and concentrated under reduced pressure. After chromatographic purification of the residue, 5.2 g of clean product were isolated.
Step 3: Synthesis of 4-chloro-3-mercapto-2-methylbenzoic acid
6.61 g (85% by weight pure, 100.1 mmol) of potassium hydroxide were added to 4.80 g (16.7 mmol) of methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate in 150 ml of methanol, and the mixture was stirred under reflux for two days. The reaction mixture was freed from the solvent, water was added to the residue, the mixture was acidified with 1M HCl and the solid was removed by filtration. This gave 3.2 g of clean product.
Step 4: Synthesis of 4-chloro-3-ethylthio-2-methylbenzoic acid
3.71 g (11.3 mmol) of cesium carbonate were added to 1.10 g (5.42 mmol) of 4-chloro-3-mercapto-2-methylbenzoic acid in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 10 min, and 1.02 g (6.51 mmol) of iodoethane were then slowly added dropwise. The reaction mixture was then stirred at RT for 16 h. The solvent was then removed, and a mixture of 20 ml of methanol and 2 ml of 20% strength aqueous sodium hydroxide solution was then added to the reaction mixture. For the hydrolysis of the ethyl ester formed, the mixture was stirred at RT for 16 h and then freed from the solvents. The residue was taken up in water and acidified with diluted HCl, and the mixture was stirred at RT for 10 min and then filtered. The residue was washed with water and sucked dry. 1.15 g of clean product were isolated.
Step 5: Synthesis of 4-chloro-3-ethylsulfinyl-2-methylbenzoic acid (No. 4-238)
1.15 g (4.98 mmol) of 4-chloro-3-ethylthio-2-methylbenzoic acid in 10 ml of glacial acetic acid were heated to a temperature of 50° C.-60° C. At this temperature, 484 mg (35% strength, 4.98 mmol) of an aqueous hydrogen peroxide solution were added dropwise. The mixture was stirred at this temperature for 5 h. The reaction mixture was cooled, washed with an aqueous saturated sodium bisulfite solution and, after analytical proof of absence of peroxides, freed from the solvents. Water was added to the residue, and the mixture was acidified with 6M HCl. The mixture was extracted with ethyl acetate, and the combined organic phases were dried, filtered and, under reduced pressure, freed from the solvent. 1.24 g of the product (purify about 95% by weight) were isolated.
Step 6: Synthesis of 4-(4-chloro-3-ethylsulfinyl-2-methyl benzoyl)-5-hydroxy-1,3-dimethylpyrazole
128 mg (1.14 mmol) of 5-hydroxy-1,3-dimethylpyrazole were added to 270 mg (purity 95% by weight; 1.04 mmol) of 4-chloro-3-ethylsulfinyl-2-methylbenzoic acid in 20 ml of dichloromethane (CH2Cl2). 239 mg (1.24 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 16 h. For work-up, 3 ml of 1M HCl were added, and the organic phase was freed from the solvent. 210 mg (2.07 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. The residue was stirred at RT with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted with CH2Cl2. The organic phase was freed from the solvent and the residue was then purified chromatographically. This gave 100 mg of clean product.
2. Preparation of 5-hydroxy-1-methyl-4-(2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoyl)pyrazole (No. 1-9 of Table 1)
Step 1: Synthesis of 2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoic acid (No. 4-9)
900 mg (3.45 mmol) of 2-methyl-4-methylsulfonyl-3-methylthiobenzoic acid in 10 ml of glacial acetic acid were heated to a temperature of 50° C.-60° C. At this temperature, 336 mg (35% strength, 3.45 mmol) of an aqueous hydrogen peroxide solution were added dropwise. The mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled, washed with an aqueous 10% strength sodium bisulfite solution and, after analytical proof of absence of peroxides, freed from the solvents. Water was added to the residue, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried, filtered and, under reduced pressure, freed from the solvent. 950 mg of the clean product were isolated.
Step 2: Synthesis of 5-hydroxy-1-methyl-4-(2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoyl)pyrazole
90 mg (0.91 mmol) of 5-hydroxy-1-methylpyrazole and a spatula tip of 4-(dimethylamino)pyridine were added to 230 mg (0.83 mmol) of 2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoic acid in 20 ml of CH2Cl2. 191 mg (0.99 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 90 min. 3 ml of 1M HCl were then added, and the organic phase was freed from the solvent. 168 mg (1.66 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 15 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. 15 ml of CH2Cl2 were added to the residue, and 2 ml of 1M HCl were then added. After phase separation, the organic phase was freed from the solvent. The residue was stirred with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether at RT for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted three times with CH2Cl2. The combined organic phases were freed from the solvent. This gave 171 mg of clean product.
The examples listed in the tables hereinbelow were prepared analogously to abovementioned methods or are obtainable analogously to above-mentioned methods. These compounds are very particularly preferred.







TABLE 1







Compounds of the formula (I) according to the invention in which R1 is


methyl, R2 and R4 are each hydrogen.








 















Physical data:


No.
X
R3
Y
1H—NMR: δ [CDCl3]





1-1
Cl
Me
SO2Me



1-2
Cl
Et
SO2Me
8.23 (d, 1 H), 7.66 (d, 1 H), 7.32






(s, 1 H), 3.92 (m, 1 H), 3.73






(s, 3 H), 3.45 (s, 3 H), 3.28






(m, 1 H), 1.53 (t, 3 H)


1-3
Cl
n-Pr
SO2Me



1-4
Cl
i-Pr
SO2Me



1-5
Br
Me
SO2Me



1-6
Br
Et
SO2Me



1-7
Br
n-Pr
SO2Me



1-8
Br
i-Pr
SO2Me



1-9
Me
Me
SO2Me
8.08 (d, 1 H), 7.62 (d, 1 H), 7.27






(s, 1 H), 3.72 (s, 3 H), 3.38 (s,






3 H), 3.18 (s, 3 H), 2.87 (s, 3 H)


1-10
Me
Et
SO2Me
8.08 (d, 1 H), 7.61 (d, 1 H), 7.27






(s, 1 H), 3.72 (s, 3 H), 3.52 (m,






1 H), 3.38 (s, 3 H), 3.28 (m, 1 H),






2.82 (s, 3 H), 1.52 (t, 3 H)


1-11
Me
n-Pr
SO2Me



1-12
Me
i-Pr
SO2Me



1-13
Et
Me
SO2Me



1-14
Et
Et
SO2Me



1-15
Et
n-Pr
SO2Me



1-16
Et
i-Pr
SO2Me



1-17
CF3
Me
SO2Me



1-18
CF3
Et
SO2Me



1-19
CF3
n-Pr
SO2Me



1-20
CF3
i-Pr
SO2Me



1-21
OMe
Me
SO2Me



1-22
OMe
Et
SO2Me



1-23
OMe
n-Pr
SO2Me



1-24
OMe
i-Pr
SO2Me



1-25
OEt
Me
SO2Me



1-26
OEt
Et
SO2Me



1-27
OEt
n-Pr
SO2Me



1-28
OEt
i-Pr
SO2Me



1-29
NO2
Me
SO2Me



1-30
NO2
Et
SO2Me



1-31
NO2
n-Pr
SO2Me



1-32
NO2
i-Pr
SO2Me



1-33
SO2Me
Me
SO2Me



1-34
SO2Me
Et
SO2Me



1-35
SO2Me
n-Pr
SO2Me



1-36
SO2Me
i-Pr
SO2Me



1-37
CH2OMe
Me
SO2Me



1-38
CH2OMe
Et
SO2Me



1-39
CH2OMe
n-Pr
SO2Me



1-40
CH2OMe
i-Pr
SO2Me



1-41
CH2SO2Me
Me
SO2Me



1-42
CH2SO2Me
Et
SO2Me



1-43
CH2SO2Me
n-Pr
SO2Me



1-44
CH2SO2Me
i-Pr
SO2Me



1-45
CH2OCH2CH2OMe
Me
SO2Me
8.21 (d, 1 H), 7.67 (d, 1 H), 7.37






(s, 1 H), 5.57-5.32 (br. signal,






1 H), 5.00 (d, 1 H), 3.72 (s, 3 H),






3.63-3.58 (m, 1 H), 3.56-3.50






(m, 1 H), 3.42-3.25 (m, 2 H), 3.37






(s, 3 H), 3.32 (s, 3 H), 3.23 (s, 3 H)


1-46
CH2OCH2CH2OMe
Et
SO2Me



1-47
CH2OCH2CH2OMe
n-Pr
SO2Me



1-48
CH2OCH2CH2OMe
i-Pr
SO2Me



1-49
CH2OCH2CH2OEt
Me
SO2Me



1-50
CH2OCH2CH2OEt
Et
SO2Me



1-51
CH2OCH2CH2OEt
n-Pr
SO2Me



1-52
CH2OCH2CH2OEt
i-Pr
SO2Me



1-53
CH2OCH2CH2CH2OMe
Me
SO2Me



1-54
CH2OCH2CH2CH2OMe
Et
SO2Me



1-55
CH2OCH2CH2CH2OMe
n-Pr
SO2Me



1-56
CH2OCH2CH2CH2OMe
i-Pr
SO2Me



1-57
CH2OCH2OMe
Me
SO2Me



1-58
CH2OCH2OMe
Et
SO2Me



1-59
CH2OCH2OMe
n-Pr
SO2Me



1-60
CH2OCH2OMe
i-Pr
SO2Me



1-61
CH2OCH2OEt
Me
SO2Me



1-62
CH2OCH2OEt
Et
SO2Me



1-63
CH2OCH2OEt
n-Pr
SO2Me



1-64
CH2OCH2OEt
i-Pr
SO2Me



1-65
CH2OCH2CH2SO2Me
Me
SO2Me



1-66
CH2OCH2CH2SO2Me
Et
SO2Me



1-67
CH2OCH2CH2SO2Me
n-Pr
SO2Me



1-68
CH2OCH2CH2SO2Me
i-Pr
SO2Me



1-69
CH2SO2CH2CH2OMe
Me
SO2Me



1-70
CH2SO2CH2CH2OMe
Et
SO2Me



1-71
CH2SO2CH2CH2OMe
n-Pr
SO2Me



1-72
CH2SO2CH2CH2OMe
i-Pr
SO2Me



1-73
CH2SO2CH2CH2SO2Me
Me
SO2Me



1-74
CH2SO2CH2CH2SO2Me
Et
SO2Me



1-75
CH2SO2CH2CH2SO2Me
n-Pr
SO2Me



1-76
CH2SO2CH2CH2SO2Me
i-Pr
SO2Me



1-77
Cl
Me
SO2Et



1-78
Cl
Et
SO2Et



1-79
Cl
n-Pr
SO2Et



1-80
Cl
i-Pr
SO2Et



1-81
Br
Me
SO2Et



1-82
Br
Et
SO2Et



1-83
Br
n-Pr
SO2Et



1-84
Br
i-Pr
SO2Et



1-85
Me
Me
SO2Et



1-86
Me
Et
SO2Et



1-87
Me
n-Pr
SO2Et



1-88
Me
i-Pr
SO2Et



1-89
Et
Me
SO2Et



1-90
Et
Et
SO2Et



1-91
Et
n-Pr
SO2Et



1-92
Et
i-Pr
SO2Et



1-93
CF3
Me
SO2Et



1-94
CF3
Et
SO2Et



1-95
CF3
n-Pr
SO2Et



1-96
CF3
i-Pr
SO2Et



1-97
OMe
Me
SO2Et



1-98
OMe
Et
SO2Et



1-99
OMe
n-Pr
SO2Et



1-100
OMe
i-Pr
SO2Et



1-101
OEt
Me
SO2Et



1-102
OEt
Et
SO2Et



1-103
OEt
n-Pr
SO2Et



1-104
OEt
i-Pr
SO2Et



1-105
NO2
Me
SO2Et



1-106
NO2
Et
SO2Et



1-107
NO2
n-Pr
SO2Et



1-108
NO2
i-Pr
SO2Et



1-109
SO2Me
Me
SO2Et



1-110
SO2Me
Et
SO2Et



1-111
SO2Me
n-Pr
SO2Et



1-112
SO2Me
i-Pr
SO2Et



1-113
CH2OMe
Me
SO2Et



1-114
CH2OMe
Et
SO2Et



1-115
CH2OMe
n-Pr
SO2Et



1-116
CH2OMe
i-Pr
SO2Et



1-117
CH2SO2Me
Me
SO2Et



1-118
CH2SO2Me
Et
SO2Et



1-119
CH2SO2Me
n-Pr
SO2Et



1-120
CH2SO2Me
i-Pr
SO2Et



1-121
CH2OCH2CH2OMe
Me
SO2Et



1-122
CH2OCH2CH2OMe
Et
SO2Et



1-123
CH2OCH2CH2OMe
n-Pr
SO2Et



1-124
CH2OCH2CH2OMe
i-Pr
SO2Et



1-125
CH2OCH2CH2OEt
Me
SO2Et



1-126
CH2OCH2CH2OEt
Et
SO2Et



1-127
CH2OCH2CH2OEt
n-Pr
SO2Et



1-128
CH2OCH2CH2OEt
i-Pr
SO2Et



1-129
CH2OCH2CH2CH2OMe
Me
SO2Et



1-130
CH2OCH2CH2CH2OMe
Et
SO2Et



1-131
CH2OCH2CH2CH2OMe
n-Pr
SO2Et



1-132
CH2OCH2CH2CH2OMe
i-Pr
SO2Et



1-133
CH2OCH2OMe
Me
SO2Et



1-134
CH2OCH2OMe
Et
SO2Et



1-135
CH2OCH2OMe
n-Pr
SO2Et



1-136
CH2OCH2OMe
i-Pr
SO2Et



1-137
CH2OCH2OEt
Me
SO2Et



1-138
CH2OCH2OEt
Et
SO2Et



1-139
CH2OCH2OEt
n-Pr
SO2Et



1-140
CH2OCH2OEt
i-Pr
SO2Et



1-141
CH2OCH2CH2SO2Me
Me
SO2Et



1-142
CH2OCH2CH2SO2Me
Et
SO2Et



1-143
CH2OCH2CH2SO2Me
n-Pr
SO2Et



1-144
CH2OCH2CH2SO2Me
i-Pr
SO2Et



1-145
CH2SO2CH2CH2OMe
Me
SO2Et



1-146
CH2SO2CH2CH2OMe
Et
SO2Et



1-147
CH2SO2CH2CH2OMe
n-Pr
SO2Et



1-148
CH2SO2CH2CH2OMe
i-Pr
SO2Et



1-149
CH2SO2CH2CH2SO2Me
Me
SO2Et



1-150
CH2SO2CH2CH2SO2Me
Et
SO2Et



1-151
CH2SO2CH2CH2SO2Me
n-Pr
SO2Et



1-152
CH2SO2CH2CH2SO2Me
i-Pr
SO2Et



1-153
Cl
Me
F



1-154
Cl
Et
F



1-155
Cl
n-Pr
F



1-156
Cl
i-Pr
F



1-157
Br
Me
F



1-158
Br
Et
F



1-159
Br
n-Pr
F



1-160
Br
i-Pr
F



1-161
Me
Me
F



1-162
Me
Et
F



1-163
Me
n-Pr
F



1-164
Me
i-Pr
F



1-165
Et
Me
F



1-166
Et
Et
F



1-167
Et
n-Pr
F



1-168
Et
i-Pr
F



1-169
CF3
Me
F



1-170
CF3
Et
F



1-171
CF3
n-Pr
F



1-172
CF3
i-Pr
F



1-173
OMe
Me
F



1-174
OMe
Et
F



1-175
OMe
n-Pr
F



1-176
OMe
i-Pr
F



1-177
OEt
Me
F



1-178
OEt
Et
F



1-179
OEt
n-Pr
F



1-180
OEt
i-Pr
F



1-181
NO2
Me
F



1-182
NO2
Et
F



1-183
NO2
n-Pr
F



1-184
NO2
i-Pr
F



1-185
SO2Me
Me
F



1-186
SO2Me
Et
F



1-187
SO2Me
n-Pr
F



1-188
SO2Me
i-Pr
F



1-189
CH2OMe
Me
F



1-190
CH2OMe
Et
F



1-191
CH2OMe
n-Pr
F



1-192
CH2OMe
i-Pr
F



1-193
CH2SO2Me
Me
F



1-194
CH2SO2Me
Et
F



1-195
CH2SO2Me
n-Pr
F



1-196
CH2SO2Me
i-Pr
F



1-197
CH2OCH2CH2OMe
Me
F



1-198
CH2OCH2CH2OMe
Et
F



1-199
CH2OCH2CH2OMe
n-Pr
F



1-200
CH2OCH2CH2OMe
i-Pr
F



1-201
CH2OCH2CH2OEt
Me
F



1-202
CH2OCH2CH2OEt
Et
F



1-203
CH2OCH2CH2OEt
n-Pr
F



1-204
CH2OCH2CH2OEt
i-Pr
F



1-205
CH2OCH2CH2CH2OMe
Me
F



1-206
CH2OCH2CH2CH2OMe
Et
F



1-207
CH2OCH2CH2CH2OMe
n-Pr
F



1-208
CH2OCH2CH2CH2OMe
i-Pr
F



1-209
CH2OCH2OMe
Me
F



1-210
CH2OCH2OMe
Et
F



1-211
CH2OCH2OMe
n-Pr
F



1-212
CH2OCH2OMe
i-Pr
F



1-213
CH2OCH2OEt
Me
F



1-214
CH2OCH2OEt
Et
F



1-215
CH2OCH2OEt
n-Pr
F



1-216
CH2OCH2OEt
i-Pr
F



1-217
CH2OCH2CH2SO2Me
Me
F



1-218
CH2OCH2CH2SO2Me
Et
F



1-219
CH2OCH2CH2SO2Me
n-Pr
F



1-220
CH2OCH2CH2SO2Me
i-Pr
F



1-221
CH2SO2CH2CH2OMe
Me
F



1-222
CH2SO2CH2CH2OMe
Et
F



1-223
CH2SO2CH2CH2OMe
n-Pr
F



1-224
CH2SO2CH2CH2OMe
i-Pr
F



1-225
CH2SO2CH2CH2SO2Me
Me
F



1-226
CH2SO2CH2CH2SO2Me
Et
F



1-227
CH2SO2CH2CH2SO2Me
n-Pr
F



1-228
CH2SO2CH2CH2SO2Me
i-Pr
F



1-229
Cl
Me
Cl



1-230
Cl
Et
Cl



1-231
Cl
n-Pr
Cl



1-232
Cl
i-Pr
Cl



1-233
Br
Me
Cl



1-234
Br
Et
Cl



1-235
Br
n-Pr
Cl



1-236
Br
i-Pr
Cl



1-237
Me
Me
Cl
7.41 (d, 1 H), 7.36 (d, 1 H), 7.32






(s, 1 H), 3.71 (s, 3 H), 3.02 (s,






3 H), 2.74 (s, 3 H)


1-238
Me
Et
Cl
7.41 (d, 1 H), 7.36 (d, 1 H), 7.31






(s, 1 H), 3.71 (s, 3 H), 3.38 (m,






1 H), 3.16 (m, 1 H), 2.72 (s, 3 H),






1.41 (t, 3 H)


1-239
Me
n-Pr
Cl



1-240
Me
i-Pr
Cl



1-241
Et
Me
Cl



1-242
Et
Et
Cl



1-243
Et
n-Pr
Cl



1-244
Et
i-Pr
Cl



1-245
CF3
Me
Cl



1-246
CF3
Et
Cl



1-247
CF3
n-Pr
Cl



1-248
CF3
i-Pr
Cl



1-249
OMe
Me
Cl



1-250
OMe
Et
Cl



1-251
OMe
n-Pr
Cl



1-252
OMe
i-Pr
Cl



1-253
OEt
Me
Cl



1-254
OEt
Et
Cl



1-255
OEt
n-Pr
Cl



1-256
OEt
i-Pr
Cl



1-257
NO2
Me
Cl



1-258
NO2
Et
Cl



1-259
NO2
n-Pr
Cl



1-260
NO2
i-Pr
Cl



1-261
SO2Me
Me
Cl



1-262
SO2Me
Et
Cl



1-263
SO2Me
n-Pr
Cl



1-264
SO2Me
i-Pr
Cl



1-265
CH2OMe
Me
Cl



1-266
CH2OMe
Et
Cl



1-267
CH2OMe
n-Pr
Cl



1-268
CH2OMe
i-Pr
Cl



1-269
CH2SO2Me
Me
Cl



1-270
CH2SO2Me
Et
Cl



1-271
CH2SO2Me
n-Pr
Cl



1-272
CH2SO2Me
i-Pr
Cl



1-273
CH2OCH2CH2OMe
Me
Cl



1-274
CH2OCH2CH2OMe
Et
Cl



1-275
CH2OCH2CH2OMe
n-Pr
Cl



1-276
CH2OCH2CH2OMe
i-Pr
Cl



1-277
CH2OCH2CH2OEt
Me
Cl



1-278
CH2OCH2CH2OEt
Et
Cl



1-279
CH2OCH2CH2OEt
n-Pr
Cl



1-280
CH2OCH2CH2OEt
i-Pr
Cl



1-281
CH2OCH2CH2CH2OMe
Me
Cl



1-282
CH2OCH2CH2CH2OMe
Et
Cl



1-283
CH2OCH2CH2CH2OMe
n-Pr
Cl



1-284
CH2OCH2CH2CH2OMe
i-Pr
Cl



1-285
CH2OCH2OMe
Me
Cl



1-286
CH2OCH2OMe
Et
Cl



1-287
CH2OCH2OMe
n-Pr
Cl



1-288
CH2OCH2OMe
i-Pr
Cl



1-289
CH2OCH2OEt
Me
Cl



1-290
CH2OCH2OEt
Et
Cl



1-291
CH2OCH2OEt
n-Pr
Cl



1-292
CH2OCH2OEt
i-Pr
Cl



1-293
CH2OCH2CH2SO2Me
Me
Cl



1-294
CH2OCH2CH2SO2Me
Et
Cl



1-295
CH2OCH2CH2SO2Me
n-Pr
Cl



1-296
CH2OCH2CH2SO2Me
i-Pr
Cl



1-297
CH2SO2CH2CH2OMe
Me
Cl



1-298
CH2SO2CH2CH2OMe
Et
Cl



1-299
CH2SO2CH2CH2OMe
n-Pr
Cl



1-300
CH2SO2CH2CH2OMe
i-Pr
Cl



1-301
CH2SO2CH2CH2SO2Me
Me
Cl



1-302
CH2SO2CH2CH2SO2Me
Et
Cl



1-303
CH2SO2CH2CH2SO2Me
n-Pr
Cl



1-304
CH2SO2CH2CH2SO2Me
i-Pr
Cl



1-305
Cl
Me
Br



1-306
Cl
Et
Br



1-307
Cl
n-Pr
Br



1-308
Cl
i-Pr
Br



1-309
Br
Me
Br



1-310
Br
Et
Br



1-311
Br
n-Pr
Br



1-312
Br
i-Pr
Br



1-313
Me
Me
Br
7.55 (d, 1 H), 7.32 (s, 1 H), 7.30






(d, 1 H), 3.72 (s, 3 H), 3.01 (s,






3 H), 2.77 (s, 3 H)


1-314
Me
Et
Br



1-315
Me
n-Pr
Br



1-316
Me
i-Pr
Br



1-317
Et
Me
Br



1-318
Et
Et
Br



1-319
Et
n-Pr
Br



1-320
Et
i-Pr
Br



1-321
CF3
Me
Br



1-322
CF3
Et
Br



1-323
CF3
n-Pr
Br



1-324
CF3
i-Pr
Br



1-325
OMe
Me
Br



1-326
OMe
Et
Br



1-327
OMe
n-Pr
Br



1-328
OMe
i-Pr
Br



1-329
OEt
Me
Br



1-330
OEt
Et
Br



1-331
OEt
n-Pr
Br



1-332
OEt
i-Pr
Br



1-333
NO2
Me
Br



1-334
NO2
Et
Br



1-335
NO2
n-Pr
Br



1-336
NO2
i-Pr
Br



1-337
SO2Me
Me
Br



1-338
SO2Me
Et
Br



1-339
SO2Me
n-Pr
Br



1-340
SO2Me
i-Pr
Br



1-341
CH2OMe
Me
Br



1-342
CH2OMe
Et
Br



1-343
CH2OMe
n-Pr
Br



1-344
CH2OMe
i-Pr
Br



1-345
CH2SO2Me
Me
Br



1-346
CH2SO2Me
Et
Br



1-347
CH2SO2Me
n-Pr
Br



1-348
CH2SO2Me
i-Pr
Br



1-349
CH2OCH2CH2OMe
Me
Br



1-350
CH2OCH2CH2OMe
Et
Br



1-351
CH2OCH2CH2OMe
n-Pr
Br



1-352
CH2OCH2CH2OMe
i-Pr
Br



1-353
CH2OCH2CH2OEt
Me
Br



1-354
CH2OCH2CH2OEt
Et
Br



1-355
CH2OCH2CH2OEt
n-Pr
Br



1-356
CH2OCH2CH2OEt
i-Pr
Br



1-357
CH2OCH2CH2CH2OMe
Me
Br



1-358
CH2OCH2CH2CH2OMe
Et
Br



1-359
CH2OCH2CH2CH2OMe
n-Pr
Br



1-360
CH2OCH2CH2CH2OMe
i-Pr
Br



1-361
CH2OCH2OMe
Me
Br



1-362
CH2OCH2OMe
Et
Br



1-363
CH2OCH2OMe
n-Pr
Br



1-364
CH2OCH2OMe
i-Pr
Br



1-365
CH2OCH2OEt
Me
Br



1-366
CH2OCH2OEt
Et
Br



1-367
CH2OCH2OEt
n-Pr
Br



1-368
CH2OCH2OEt
i-Pr
Br



1-369
CH2OCH2CH2SO2Me
Me
Br



1-370
CH2OCH2CH2SO2Me
Et
Br



1-371
CH2OCH2CH2SO2Me
n-Pr
Br



1-372
CH2OCH2CH2SO2Me
i-Pr
Br



1-373
CH2SO2CH2CH2OMe
Me
Br



1-374
CH2SO2CH2CH2OMe
Et
Br



1-375
CH2SO2CH2CH2OMe
n-Pr
Br



1-376
CH2SO2CH2CH2OMe
i-Pr
Br



1-377
CH2SO2CH2CH2SO2Me
Me
Br



1-378
CH2SO2CH2CH2SO2Me
Et
Br



1-379
CH2SO2CH2CH2SO2Me
n-Pr
Br



1-380
CH2SO2CH2CH2SO2Me
i-Pr
Br



1-381
Cl
Me
I



1-382
Cl
Et
I



1-383
Cl
n-Pr
I



1-384
Cl
i-Pr
I



1-385
Br
Me
I



1-386
Br
Et
I



1-387
Br
n-Pr
I



1-388
Br
i-Pr
I



1-389
Me
Me
I
7.86 (d, 1 H), 7.31 (s, 1 H), 7.11






(d, 1 H), 3.71 (s, 3 H), 2.98 (s,






3 H), 2.76 (s, 3 H)


1-390
Me
Et
I



1-391
Me
n-Pr
I



1-392
Me
i-Pr
I



1-393
Et
Me
I



1-394
Et
Et
I



1-395
Et
n-Pr
I



1-396
Et
i-Pr
I



1-397
CF3
Me
I



1-398
CF3
Et
I



1-399
CF3
n-Pr
I



1-400
CF3
i-Pr
I



1-401
OMe
Me
I



1-402
OMe
Et
I



1-403
OMe
n-Pr
I



1-404
OMe
i-Pr
I



1-405
OEt
Me
I



1-406
OEt
Et
I



1-407
OEt
n-Pr
I



1-408
OEt
i-Pr
I



1-409
NO2
Me
I



1-410
NO2
Et
I



1-411
NO2
n-Pr
I



1-412
NO2
i-Pr
I



1-413
SO2Me
Me
I



1-414
SO2Me
Et
I



1-415
SO2Me
n-Pr
I



1-416
SO2Me
i-Pr
I



1-417
CH2OMe
Me
I



1-418
CH2OMe
Et
I



1-419
CH2OMe
n-Pr
I



1-420
CH2OMe
i-Pr
I



1-421
CH2SO2Me
Me
I



1-422
CH2SO2Me
Et
I



1-423
CH2SO2Me
n-Pr
I



1-424
CH2SO2Me
i-Pr
I



1-425
CH2OCH2CH2OMe
Me
I



1-426
CH2OCH2CH2OMe
Et
I



1-427
CH2OCH2CH2OMe
n-Pr
I



1-428
CH2OCH2CH2OMe
i-Pr
I



1-429
CH2OCH2CH2OEt
Me
I



1-430
CH2OCH2CH2OEt
Et
I



1-431
CH2OCH2CH2OEt
n-Pr
I



1-432
CH2OCH2CH2OEt
i-Pr
I



1-433
CH2OCH2CH2CH2OMe
Me
I



1-434
CH2OCH2CH2CH2OMe
Et
I



1-435
CH2OCH2CH2CH2OMe
n-Pr
I



1-436
CH2OCH2CH2CH2OMe
i-Pr
I



1-437
CH2OCH2OMe
Me
I



1-438
CH2OCH2OMe
Et
I



1-439
CH2OCH2OMe
n-Pr
I



1-440
CH2OCH2OMe
i-Pr
I



1-441
CH2OCH2OEt
Me
I



1-442
CH2OCH2OEt
Et
I



1-443
CH2OCH2OEt
n-Pr
I



1-444
CH2OCH2OEt
i-Pr
I



1-445
CH2OCH2CH2SO2Me
Me
I



1-446
CH2OCH2CH2SO2Me
Et
I



1-447
CH2OCH2CH2SO2Me
n-Pr
I



1-448
CH2OCH2CH2SO2Me
i-Pr
I



1-449
CH2SO2CH2CH2OMe
Me
I



1-450
CH2SO2CH2CH2OMe
Et
I



1-451
CH2SO2CH2CH2OMe
n-Pr
I



1-452
CH2SO2CH2CH2OMe
i-Pr
I



1-453
CH2SO2CH2CH2SO2Me
Me
I



1-454
CH2SO2CH2CH2SO2Me
Et
I



1-455
CH2SO2CH2CH2SO2Me
n-Pr
I



1-456
CH2SO2CH2CH2SO2Me
i-Pr
I



1-457
Cl
Me
NO2



1-458
Cl
Et
NO2



1-459
Cl
n-Pr
NO2



1-460
Cl
i-Pr
NO2



1-461
Br
Me
NO2



1-462
Br
Et
NO2



1-463
Br
n-Pr
NO2



1-464
Br
i-Pr
NO2



1-465
Me
Me
NO2



1-466
Me
Et
NO2



1-467
Me
n-Pr
NO2



1-468
Me
i-Pr
NO2



1-469
Et
Me
NO2



1-470
Et
Et
NO2



1-471
Et
n-Pr
NO2



1-472
Et
i-Pr
NO2



1-473
CF3
Me
NO2



1-474
CF3
Et
NO2



1-475
CF3
n-Pr
NO2



1-476
CF3
i-Pr
NO2



1-477
OMe
Me
NO2



1-478
OMe
Et
NO2



1-479
OMe
n-Pr
NO2



1-480
OMe
i-Pr
NO2



1-481
OEt
Me
NO2



1-482
OEt
Et
NO2



1-483
OEt
n-Pr
NO2



1-484
OEt
i-Pr
NO2



1-485
NO2
Me
NO2



1-486
NO2
Et
NO2



1-487
NO2
n-Pr
NO2



1-488
NO2
i-Pr
NO2



1-489
SO2Me
Me
NO2



1-490
SO2Me
Et
NO2



1-491
SO2Me
n-Pr
NO2



1-492
SO2Me
i-Pr
NO2



1-493
CH2OMe
Me
NO2



1-494
CH2OMe
Et
NO2



1-495
CH2OMe
n-Pr
NO2



1-496
CH2OMe
i-Pr
NO2



1-497
CH2SO2Me
Me
NO2



1-498
CH2SO2Me
Et
NO2



1-499
CH2SO2Me
n-Pr
NO2



1-500
CH2SO2Me
i-Pr
NO2



1-501
CH2OCH2CH2OMe
Me
NO2



1-502
CH2OCH2CH2OMe
Et
NO2



1-503
CH2OCH2CH2OMe
n-Pr
NO2



1-504
CH2OCH2CH2OMe
i-Pr
NO2



1-505
CH2OCH2CH2OEt
Me
NO2



1-506
CH2OCH2CH2OEt
Et
NO2



1-507
CH2OCH2CH2OEt
n-Pr
NO2



1-508
CH2OCH2CH2OEt
i-Pr
NO2



1-509
CH2OCH2CH2CH2OMe
Me
NO2



1-510
CH2OCH2CH2CH2OMe
Et
NO2



1-511
CH2OCH2CH2CH2OMe
n-Pr
NO2



1-512
CH2OCH2CH2CH2OMe
i-Pr
NO2



1-513
CH2OCH2OMe
Me
NO2



1-514
CH2OCH2OMe
Et
NO2



1-515
CH2OCH2OMe
n-Pr
NO2



1-516
CH2OCH2OMe
i-Pr
NO2



1-517
CH2OCH2OEt
Me
NO2



1-518
CH2OCH2OEt
Et
NO2



1-519
CH2OCH2OEt
n-Pr
NO2



1-520
CH2OCH2OEt
i-Pr
NO2



1-521
CH2OCH2CH2SO2Me
Me
NO2



1-522
CH2OCH2CH2SO2Me
Et
NO2



1-523
CH2OCH2CH2SO2Me
n-Pr
NO2



1-524
CH2OCH2CH2SO2Me
i-Pr
NO2



1-525
CH2SO2CH2CH2OMe
Me
NO2



1-526
CH2SO2CH2CH2OMe
Et
NO2



1-527
CH2SO2CH2CH2OMe
n-Pr
NO2



1-528
CH2SO2CH2CH2OMe
i-Pr
NO2



1-529
CH2SO2CH2CH2SO2Me
Me
NO2



1-530
CH2SO2CH2CH2SO2Me
Et
NO2



1-531
CH2SO2CH2CH2SO2Me
n-Pr
NO2



1-532
CH2SO2CH2CH2SO2Me
i-Pr
NO2





The abbreviations used are:


Et = ethyl


Me = methyl


Pr = propyl


Ph = phenyl













TABLE 2







Compounds of the formula (I) according to the invention in which R1 is


ethyl, R2 and R4 are each hydrogen.








 















Physical data:


No.
X
R3
Y
1H-NMR: δ [CDCl3]





2-1
Cl
Me
SO2Me



2-2
Cl
Et
SO2Me


2-3
Cl
n-Pr
SO2Me


2-4
Cl
i-Pr
SO2Me


2-5
Br
Me
SO2Me


2-6
Br
Et
SO2Me


2-7
Br
n-Pr
SO2Me


2-8
Br
i-Pr
SO2Me


2-9
Me
Me
SO2Me
8.08 (d, 1H), 7.62 (d,






1H), 7.28 (s, 1H), 4.09






(q, 2H), 3.38 (s, 3H),






3.18 (s, 3H), 2.88 (s,






3H), 1.46 (t, 3H)


2-10
Me
Et
SO2Me
8.10 (d, 1H), 7.62 (d,






1H), 7.28 (s, 1H), 4.08






(q, 2H), 3.52 (m, 1H),






3.38 (s, 3H), 3.28 (m,






1H), 2.82 (s, 3H), 1.52






(t, 3H), 1.47 (t, 3H)


2-11
Me
n-Pr
SO2Me
8.08 (d, 1H), 7.61 (d,






1H), 7.27 (s, 1H), 4.08






(q, 2H), 3.52 (m, 1H),






3.37 (s, 3H), 3.16 (m,






1H), 2.83 (s, 3H), 2.02






(m, 2H), 1.47 (t, 3H),






1.17 (t, 3H)


2-12
Me
i-Pr
SO2Me
8.17 (m, 1H), 7.62 (d,






1H), 7.26 (s, 1H), 4.08






(q, 2H), 3.74 (m, 1H),






3.37 (s, 3H), 2.87 (s,






3H), 1.55 (d, 3H),






1.47 (t, 3H), 1.27 (m,






3H)


2-13
Et
Me
SO2Me


2-14
Et
Et
SO2Me


2-15
Et
n-Pr
SO2Me


2-16
Et
i-Pr
SO2Me


2-17
CF3
Me
SO2Me


2-18
CF3
Et
SO2Me


2-19
CF3
n-Pr
SO2Me


2-20
CF3
i-Pr
SO2Me


2-21
OMe
Me
SO2Me


2-22
OMe
Et
SO2Me


2-23
OMe
n-Pr
SO2Me


2-24
OMe
i-Pr
SO2Me


2-25
OEt
Me
SO2Me


2-26
OEt
Et
SO2Me


2-27
OEt
n-Pr
SO2Me


2-28
OEt
i-Pr
SO2Me


2-29
NO2
Me
SO2Me


2-30
NO2
Et
SO2Me


2-31
NO2
n-Pr
SO2Me


2-32
NO2
i-Pr
SO2Me


2-33
SO2Me
Me
SO2Me


2-34
SO2Me
Et
SO2Me


2-35
SO2Me
n-Pr
SO2Me


2-36
SO2Me
i-Pr
SO2Me


2-37
CH2OMe
Me
SO2Me


2-38
CH2OMe
Et
SO2Me


2-39
CH2OMe
n-Pr
SO2Me


2-40
CH2OMe
i-Pr
SO2Me


2-41
CH2SO2Me
Me
SO2Me


2-42
CH2SO2Me
Et
SO2Me


2-43
CH2SO2Me
n-Pr
SO2Me


2-44
CH2SO2Me
i-Pr
SO2Me


2-45
CH2OCH2CH2OMe
Me
SO2Me


2-46
CH2OCH2CH2OMe
Et
SO2Me


2-47
CH2OCH2CH2OMe
n-Pr
SO2Me


2-48
CH2OCH2CH2OMe
i-Pr
SO2Me


2-49
CH2OCH2CH2OEt
Me
SO2Me
8.22 (d, 1H), 7.67 (d,






1H), 7.38 (s, 1H),






5.60-5.10 (br. signal,






1H), 4.97 (d, 1H),






4.09 (q, 2H), 3.62-






3.56 (m, 1H), 3.56-






3.49 (m, 1H), 3.47-






3.32 (m, 4H), 3.37 (s,






3H), 3.33 (s, 3H), 1.46






(t, 3H), 1.12 (t, 3H)


2-50
CH2OCH2CH2OEt
Et
SO2Me


2-51
CH2OCH2CH2OEt
n-Pr
SO2Me


2-52
CH2OCH2CH2OEt
i-Pr
SO2Me


2-53
CH2OCH2CH2CH2OMe
Me
SO2Me


2-54
CH2OCH2CH2CH2OMe
Et
SO2Me


2-55
CH2OCH2CH2CH2OMe
n-Pr
SO2Me


2-56
CH2OCH2CH2CH2OMe
i-Pr
SO2Me


2-57
CH2OCH2OMe
Me
SO2Me


2-58
CH2OCH2OMe
Et
SO2Me


2-59
CH2OCH2OMe
n-Pr
SO2Me


2-60
CH2OCH2OMe
i-Pr
SO2Me


2-61
CH2OCH2OEt
Me
SO2Me


2-62
CH2OCH2OEt
Et
SO2Me


2-63
CH2OCH2OEt
n-Pr
SO2Me


2-64
CH2OCH2OEt
i-Pr
SO2Me


2-65
CH2OCH2CH2SO2Me
Me
SO2Me


2-66
CH2OCH2CH2SO2Me
Et
SO2Me


2-67
CH2OCH2CH2SO2Me
n-Pr
SO2Me


2-68
CH2OCH2CH2SO2Me
i-Pr
SO2Me


2-69
CH2SO2CH2CH2OMe
Me
SO2Me


2-70
CH2SO2CH2CH2OMe
Et
SO2Me


2-71
CH2SO2CH2CH2OMe
n-Pr
SO2Me


2-72
CH2SO2CH2CH2OMe
i-Pr
SO2Me


2-73
CH2SO2CH2CH2SO2Me
Me
SO2Me


2-74
CH2SO2CH2CH2SO2Me
Et
SO2Me


2-75
CH2SO2CH2CH2SO2Me
n-Pr
SO2Me


2-76
CH2SO2CH2CH2SO2Me
i-Pr
SO2Me


2-77
Cl
Me
SO2Et


2-78
Cl
Et
SO2Et


2-79
Cl
n-Pr
SO2Et


2-80
Cl
i-Pr
SO2Et


2-81
Br
Me
SO2Et


2-82
Br
Et
SO2Et


2-83
Br
n-Pr
SO2Et


2-84
Br
i-Pr
SO2Et


2-85
Me
Me
SO2Et


2-86
Me
Et
SO2Et


2-87
Me
n-Pr
SO2Et


2-88
Me
i-Pr
SO2Et


2-89
Et
Me
SO2Et


2-90
Et
Et
SO2Et


2-91
Et
n-Pr
SO2Et


2-92
Et
i-Pr
SO2Et


2-93
CF3
Me
SO2Et


2-94
CF3
Et
SO2Et


2-95
CF3
n-Pr
SO2Et


2-96
CF3
i-Pr
SO2Et


2-97
OMe
Me
SO2Et


2-98
OMe
Et
SO2Et


2-99
OMe
n-Pr
SO2Et


2-100
OMe
i-Pr
SO2Et


2-101
OEt
Me
SO2Et


2-102
OEt
Et
SO2Et


2-103
OEt
n-Pr
SO2Et


2-104
OEt
i-Pr
SO2Et


2-105
NO2
Me
SO2Et


2-106
NO2
Et
SO2Et


2-107
NO2
n-Pr
SO2Et


2-108
NO2
i-Pr
SO2Et


2-109
SO2Me
Me
SO2Et


2-110
SO2Me
Et
SO2Et


2-111
SO2Me
n-Pr
SO2Et


2-112
SO2Me
i-Pr
SO2Et


2-113
CH2OMe
Me
SO2Et


2-114
CH2OMe
Et
SO2Et


2-115
CH2OMe
n-Pr
SO2Et


2-116
CH2OMe
i-Pr
SO2Et


2-117
CH2SO2Me
Me
SO2Et


2-118
CH2SO2Me
Et
SO2Et


2-119
CH2SO2Me
n-Pr
SO2Et


2-120
CH2SO2Me
i-Pr
SO2Et


2-121
CH2OCH2CH2OMe
Me
SO2Et


2-122
CH2OCH2CH2OMe
Et
SO2Et


2-123
CH2OCH2CH2OMe
n-Pr
SO2Et


2-124
CH2OCH2CH2OMe
i-Pr
SO2Et


2-125
CH2OCH2CH2OEt
Me
SO2Et


2-126
CH2OCH2CH2OEt
Et
SO2Et


2-127
CH2OCH2CH2OEt
n-Pr
SO2Et


2-128
CH2OCH2CH2OEt
i-Pr
SO2Et


2-129
CH2OCH2CH2CH2OMe
Me
SO2Et


2-130
CH2OCH2CH2CH2OMe
Et
SO2Et


2-131
CH2OCH2CH2CH2OMe
n-Pr
SO2Et


2-132
CH2OCH2CH2CH2OMe
i-Pr
SO2Et


2-133
CH2OCH2OMe
Me
SO2Et


2-134
CH2OCH2OMe
Et
SO2Et


2-135
CH2OCH2OMe
n-Pr
SO2Et


2-136
CH2OCH2OMe
i-Pr
SO2Et


2-137
CH2OCH2OEt
Me
SO2Et


2-138
CH2OCH2OEt
Et
SO2Et


2-139
CH2OCH2OEt
n-Pr
SO2Et


2-140
CH2OCH2OEt
i-Pr
SO2Et


2-141
CH2OCH2CH2SO2Me
Me
SO2Et


2-142
CH2OCH2CH2SO2Me
Et
SO2Et


2-143
CH2OCH2CH2SO2Me
n-Pr
SO2Et


2-144
CH2OCH2CH2SO2Me
i-Pr
SO2Et


2-145
CH2SO2CH2CH2OMe
Me
SO2Et


2-146
CH2SO2CH2CH2OMe
Et
SO2Et


2-147
CH2SO2CH2CH2OMe
n-Pr
SO2Et


2-148
CH2SO2CH2CH2OMe
i-Pr
SO2Et


2-149
CH2SO2CH2CH2SO2Me
Me
SO2Et


2-150
CH2SO2CH2CH2SO2Me
Et
SO2Et


2-151
CH2SO2CH2CH2SO2Me
n-Pr
SO2Et


2-152
CH2SO2CH2CH2SO2Me
i-Pr
SO2Et


2-153
Cl
Me
F


2-154
Cl
Et
F


2-155
Cl
n-Pr
F


2-156
Cl
i-Pr
F


2-157
Br
Me
F


2-158
Br
Et
F


2-159
Br
n-Pr
F


2-160
Br
i-Pr
F


2-161
Me
Me
F


2-162
Me
Et
F


2-163
Me
n-Pr
F


2-164
Me
i-Pr
F


2-165
Et
Me
F


2-166
Et
Et
F


2-167
Et
n-Pr
F


2-168
Et
i-Pr
F


2-169
CF3
Me
F


2-170
CF3
Et
F


2-171
CF3
n-Pr
F


2-172
CF3
i-Pr
F


2-173
OMe
Me
F


2-174
OMe
Et
F


2-175
OMe
n-Pr
F


2-176
OMe
i-Pr
F


2-177
OEt
Me
F


2-178
OEt
Et
F


2-179
OEt
n-Pr
F


2-180
OEt
i-Pr
F


2-181
NO2
Me
F


2-182
NO2
Et
F


2-183
NO2
n-Pr
F


2-184
NO2
i-Pr
F


2-185
SO2Me
Me
F


2-186
SO2Me
Et
F


2-187
SO2Me
n-Pr
F


2-188
SO2Me
i-Pr
F


2-189
CH2OMe
Me
F


2-190
CH2OMe
Et
F


2-191
CH2OMe
n-Pr
F


2-192
CH2OMe
i-Pr
F


2-193
CH2SO2Me
Me
F


2-194
CH2SO2Me
Et
F


2-195
CH2SO2Me
n-Pr
F


2-196
CH2SO2Me
i-Pr
F


2-197
CH2OCH2CH2OMe
Me
F


2-198
CH2OCH2CH2OMe
Et
F


2-199
CH2OCH2CH2OMe
n-Pr
F


2-200
CH2OCH2CH2OMe
i-Pr
F


2-201
CH2OCH2CH2OEt
Me
F


2-202
CH2OCH2CH2OEt
Et
F


2-203
CH2OCH2CH2OEt
n-Pr
F


2-204
CH2OCH2CH2OEt
i-Pr
F


2-205
CH2OCH2CH2CH2OMe
Me
F


2-206
CH2OCH2CH2CH2OMe
Et
F


2-207
CH2OCH2CH2CH2OMe
n-Pr
F


2-208
CH2OCH2CH2CH2OMe
i-Pr
F


2-209
CH2OCH2OMe
Me
F


2-210
CH2OCH2OMe
Et
F


2-211
CH2OCH2OMe
n-Pr
F


2-212
CH2OCH2OMe
i-Pr
F


2-213
CH2OCH2OEt
Me
F


2-214
CH2OCH2OEt
Et
F


2-215
CH2OCH2OEt
n-Pr
F


2-216
CH2OCH2OEt
i-Pr
F


2-217
CH2OCH2CH2SO2Me
Me
F


2-218
CH2OCH2CH2SO2Me
Et
F


2-219
CH2OCH2CH2SO2Me
n-Pr
F


2-220
CH2OCH2CH2SO2Me
i-Pr
F


2-221
CH2SO2CH2CH2OMe
Me
F


2-222
CH2SO2CH2CH2OMe
Et
F


2-223
CH2SO2CH2CH2OMe
n-Pr
F


2-224
CH2SO2CH2CH2OMe
i-Pr
F


2-225
CH2SO2CH2CH2SO2Me
Me
F


2-226
CH2SO2CH2CH2SO2Me
Et
F


2-227
CH2SO2CH2CH2SO2Me
n-Pr
F


2-228
CH2SO2CH2CH2SO2Me
i-Pr
F


2-229
Cl
Me
Cl


2-230
Cl
Et
Cl


2-231
Cl
n-Pr
Cl


2-232
Cl
i-Pr
Cl


2-233
Br
Me
Cl


2-234
Br
Et
Cl


2-235
Br
n-Pr
Cl


2-236
Br
i-Pr
Cl


2-237
Me
Me
Cl
7.43 (d, 1H), 7.37 (d,






1H), 7.33 (s, 1H), 4.08






(q, 2H), 3.03 (s, 3H),






2.73 (s, 3H), 1.45 (t,






3H)


2-238
Me
Et
Cl
7.41 (d, 1H), 7.36 (d,






1H), 7.32 (s, 1H), 4.07






(q, 2H), 3.38 (m, 1H),






3.17 (m, 1H), 2.72 (s,






3H), 1.46 (t, 3H), 1.41






(t, 3H)


2-239
Me
n-Pr
Cl


2-240
Me
i-Pr
Cl


2-241
Et
Me
Cl


2-242
Et
Et
Cl


2-243
Et
n-Pr
Cl


2-244
Et
i-Pr
Cl


2-245
CF3
Me
Cl


2-246
CF3
Et
Cl


2-247
CF3
n-Pr
Cl


2-248
CF3
i-Pr
Cl


2-249
OMe
Me
Cl


2-250
OMe
Et
Cl


2-251
OMe
n-Pr
Cl


2-252
OMe
i-Pr
Cl


2-253
OEt
Me
Cl


2-254
OEt
Et
Cl


2-255
OEt
n-Pr
Cl


2-256
OEt
i-Pr
Cl


2-257
NO2
Me
Cl


2-258
NO2
Et
Cl


2-259
NO2
n-Pr
Cl


2-260
NO2
i-Pr
Cl


2-261
SO2Me
Me
Cl


2-262
SO2Me
Et
Cl


2-263
SO2Me
n-Pr
Cl


2-264
SO2Me
i-Pr
Cl


2-265
CH2OMe
Me
Cl


2-266
CH2OMe
Et
Cl


2-267
CH2OMe
n-Pr
Cl


2-268
CH2OMe
i-Pr
Cl


2-269
CH2SO2Me
Me
Cl


2-270
CH2SO2Me
Et
Cl


2-271
CH2SO2Me
n-Pr
Cl


2-272
CH2SO2Me
i-Pr
Cl


2-273
CH2OCH2CH2OMe
Me
Cl


2-274
CH2OCH2CH2OMe
Et
Cl


2-275
CH2OCH2CH2OMe
n-Pr
Cl


2-276
CH2OCH2CH2OMe
i-Pr
Cl


2-277
CH2OCH2CH2OEt
Me
Cl


2-278
CH2OCH2CH2OEt
Et
Cl


2-279
CH2OCH2CH2OEt
n-Pr
Cl


2-280
CH2OCH2CH2OEt
i-Pr
Cl


2-281
CH2OCH2CH2CH2OMe
Me
Cl


2-282
CH2OCH2CH2CH2OMe
Et
Cl


2-283
CH2OCH2CH2CH2OMe
n-Pr
Cl


2-284
CH2OCH2CH2CH2OMe
i-Pr
Cl


2-285
CH2OCH2OMe
Me
Cl


2-286
CH2OCH2OMe
Et
Cl


2-287
CH2OCH2OMe
n-Pr
Cl


2-288
CH2OCH2OMe
i-Pr
Cl


2-289
CH2OCH2OEt
Me
Cl


2-290
CH2OCH2OEt
Et
Cl


2-291
CH2OCH2OEt
n-Pr
Cl


2-292
CH2OCH2OEt
i-Pr
Cl


2-293
CH2OCH2CH2SO2Me
Me
Cl


2-294
CH2OCH2CH2SO2Me
Et
Cl


2-295
CH2OCH2CH2SO2Me
n-Pr
Cl


2-296
CH2OCH2CH2SO2Me
i-Pr
Cl


2-297
CH2SO2CH2CH2OMe
Me
Cl


2-298
CH2SO2CH2CH2OMe
Et
Cl


2-299
CH2SO2CH2CH2OMe
n-Pr
Cl


2-300
CH2SO2CH2CH2OMe
i-Pr
Cl


2-301
CH2SO2CH2CH2SO2Me
Me
Cl


2-302
CH2SO2CH2CH2SO2Me
Et
Cl


2-303
CH2SO2CH2CH2SO2Me
n-Pr
Cl


2-304
CH2SO2CH2CH2SO2Me
i-Pr
Cl


2-305
Cl
Me
Br


2-306
Cl
Et
Br


2-307
Cl
n-Pr
Br


2-308
Cl
i-Pr
Br


2-309
Br
Me
Br


2-310
Br
Et
Br


2-311
Br
n-Pr
Br


2-312
Br
i-Pr
Br


2-313
Me
Me
Br
7.56 (d, 1H), 7.35 (s,






1H), 7.33 (d, 1H),






4.09 (q, 2H), 3.03 (s,






3H), 2.77 (s, 3H), 1.46






(t, 3H)


2-314
Me
Et
Br


2-315
Me
n-Pr
Br


2-316
Me
i-Pr
Br


2-317
Et
Me
Br


2-318
Et
Et
Br


2-319
Et
n-Pr
Br


2-320
Et
i-Pr
Br


2-321
CF3
Me
Br


2-322
CF3
Et
Br


2-323
CF3
n-Pr
Br


2-324
CF3
i-Pr
Br


2-325
OMe
Me
Br


2-326
OMe
Et
Br


2-327
OMe
n-Pr
Br


2-328
OMe
i-Pr
Br


2-329
OEt
Me
Br


2-330
OEt
Et
Br


2-331
OEt
n-Pr
Br


2-332
OEt
i-Pr
Br


2-333
NO2
Me
Br


2-334
NO2
Et
Br


2-335
NO2
n-Pr
Br


2-336
NO2
i-Pr
Br


2-337
SO2Me
Me
Br


2-338
SO2Me
Et
Br


2-339
SO2Me
n-Pr
Br


2-340
SO2Me
i-Pr
Br


2-341
CH2OMe
Me
Br


2-342
CH2OMe
Et
Br


2-343
CH2OMe
n-Pr
Br


2-344
CH2OMe
i-Pr
Br


2-345
CH2SO2Me
Me
Br


2-346
CH2SO2Me
Et
Br


2-347
CH2SO2Me
n-Pr
Br


2-348
CH2SO2Me
i-Pr
Br


2-349
CH2OCH2CH2OMe
Me
Br


2-350
CH2OCH2CH2OMe
Et
Br


2-351
CH2OCH2CH2OMe
n-Pr
Br


2-352
CH2OCH2CH2OMe
i-Pr
Br


2-353
CH2OCH2CH2OEt
Me
Br


2-354
CH2OCH2CH2OEt
Et
Br


2-355
CH2OCH2CH2OEt
n-Pr
Br


2-356
CH2OCH2CH2OEt
i-Pr
Br


2-357
CH2OCH2CH2CH2OMe
Me
Br


2-358
CH2OCH2CH2CH2OMe
Et
Br


2-359
CH2OCH2CH2CH2OMe
n-Pr
Br


2-360
CH2OCH2CH2CH2OMe
i-Pr
Br


2-361
CH2OCH2OMe
Me
Br


2-362
CH2OCH2OMe
Et
Br


2-363
CH2OCH2OMe
n-Pr
Br


2-364
CH2OCH2OMe
i-Pr
Br


2-365
CH2OCH2OEt
Me
Br


2-366
CH2OCH2OEt
Et
Br


2-367
CH2OCH2OEt
n-Pr
Br


2-368
CH2OCH2OEt
i-Pr
Br


2-369
CH2OCH2CH2SO2Me
Me
Br


2-370
CH2OCH2CH2SO2Me
Et
Br


2-371
CH2OCH2CH2SO2Me
n-Pr
Br


2-372
CH2OCH2CH2SO2Me
i-Pr
Br


2-373
CH2SO2CH2CH2OMe
Me
Br


2-374
CH2SO2CH2CH2OMe
Et
Br


2-375
CH2SO2CH2CH2OMe
n-Pr
Br


2-376
CH2SO2CH2CH2OMe
i-Pr
Br


2-377
CH2SO2CH2CH2SO2Me
Me
Br


2-378
CH2SO2CH2CH2SO2Me
Et
Br


2-379
CH2SO2CH2CH2SO2Me
n-Pr
Br


2-380
CH2SO2CH2CH2SO2Me
i-Pr
Br


2-381
Cl
Me
I


2-382
Cl
Et
I


2-383
Cl
n-Pr
I


2-384
Cl
i-Pr
I


2-385
Br
Me
I


2-386
Br
Et
I


2-387
Br
n-Pr
I


2-388
Br
i-Pr
I


2-389
Me
Me
I
7.87 (d, 1H), 7.31 (s,






1H), 7.12 (d, 1H),






4.08 (q, 2H), 2.97 (s,






3H), 2.77 (s, 3H), 1.45






(t, 3H)


2-390
Me
Et
I


2-391
Me
n-Pr
I


2-392
Me
i-Pr
I


2-393
Et
Me
I


2-394
Et
Et
I


2-395
Et
n-Pr
I


2-396
Et
i-Pr
I


2-397
CF3
Me
I


2-398
CF3
Et
I


2-399
CF3
n-Pr
I


2-400
CF3
i-Pr
I


2-401
OMe
Me
I


2-402
OMe
Et
I


2-403
OMe
n-Pr
I


2-404
OMe
i-Pr
I


2-405
OEt
Me
I


2-406
OEt
Et
I


2-407
OEt
n-Pr
I


2-408
OEt
i-Pr
I


2-409
NO2
Me
I


2-410
NO2
Et
I


2-411
NO2
n-Pr
I


2-412
NO2
i-Pr
I


2-413
SO2Me
Me
I


2-414
SO2Me
Et
I


2-415
SO2Me
n-Pr
I


2-416
SO2Me
i-Pr
I


2-417
CH2OMe
Me
I


2-418
CH2OMe
Et
I


2-419
CH2OMe
n-Pr
I


2-420
CH2OMe
i-Pr
I


2-421
CH2SO2Me
Me
I


2-422
CH2SO2Me
Et
I


2-423
CH2SO2Me
n-Pr
I


2-424
CH2SO2Me
i-Pr
I


2-425
CH2OCH2CH2OMe
Me
I


2-426
CH2OCH2CH2OMe
Et
I


2-427
CH2OCH2CH2OMe
n-Pr
I


2-428
CH2OCH2CH2OMe
i-Pr
I


2-429
CH2OCH2CH2OEt
Me
I


2-430
CH2OCH2CH2OEt
Et
I


2-431
CH2OCH2CH2OEt
n-Pr
I


2-432
CH2OCH2CH2OEt
i-Pr
I


2-433
CH2OCH2CH2CH2OMe
Me
I


2-434
CH2OCH2CH2CH2OMe
Et
I


2-435
CH2OCH2CH2CH2OMe
n-Pr
I


2-436
CH2OCH2CH2CH2OMe
i-Pr
I


2-437
CH2OCH2OMe
Me
I


2-438
CH2OCH2OMe
Et
I


2-439
CH2OCH2OMe
n-Pr
I


2-440
CH2OCH2OMe
i-Pr
I


2-441
CH2OCH2OEt
Me
I


2-442
CH2OCH2OEt
Et
I


2-443
CH2OCH2OEt
n-Pr
I


2-444
CH2OCH2OEt
i-Pr
I


2-445
CH2OCH2CH2SO2Me
Me
I


2-446
CH2OCH2CH2SO2Me
Et
I


2-447
CH2OCH2CH2SO2Me
n-Pr
I


2-448
CH2OCH2CH2SO2Me
i-Pr
I


2-449
CH2SO2CH2CH2OMe
Me
I


2-450
CH2SO2CH2CH2OMe
Et
I


2-451
CH2SO2CH2CH2OMe
n-Pr
I


2-452
CH2SO2CH2CH2OMe
i-Pr
I


2-453
CH2SO2CH2CH2SO2Me
Me
I


2-454
CH2SO2CH2CH2SO2Me
Et
I


2-455
CH2SO2CH2CH2SO2Me
n-Pr
I


2-456
CH2SO2CH2CH2SO2Me
i-Pr
I


2-457
Cl
Me
NO2


2-458
Cl
Et
NO2


2-459
Cl
n-Pr
NO2


2-460
Cl
i-Pr
NO2


2-461
Br
Me
NO2


2-462
Br
Et
NO2


2-463
Br
n-Pr
NO2


2-464
Br
i-Pr
NO2


2-465
Me
Me
NO2


2-466
Me
Et
NO2


2-467
Me
n-Pr
NO2


2-468
Me
i-Pr
NO2


2-469
Et
Me
NO2


2-470
Et
Et
NO2


2-471
Et
n-Pr
NO2


2-472
Et
i-Pr
NO2


2-473
CF3
Me
NO2


2-474
CF3
Et
NO2


2-475
CF3
n-Pr
NO2


2-476
CF3
i-Pr
NO2


2-477
OMe
Me
NO2


2-478
OMe
Et
NO2


2-479
OMe
n-Pr
NO2


2-480
OMe
i-Pr
NO2


2-481
OEt
Me
NO2


2-482
OEt
Et
NO2


2-483
OEt
n-Pr
NO2


2-484
OEt
i-Pr
NO2


2-485
NO2
Me
NO2


2-486
NO2
Et
NO2


2-487
NO2
n-Pr
NO2


2-488
NO2
i-Pr
NO2


2-489
SO2Me
Me
NO2


2-490
SO2Me
Et
NO2


2-491
SO2Me
n-Pr
NO2


2-492
SO2Me
i-Pr
NO2


2-493
CH2OMe
Me
NO2


2-494
CH2OMe
Et
NO2


2-495
CH2OMe
n-Pr
NO2


2-496
CH2OMe
i-Pr
NO2


2-497
CH2SO2Me
Me
NO2


2-498
CH2SO2Me
Et
NO2


2-499
CH2SO2Me
n-Pr
NO2


2-500
CH2SO2Me
i-Pr
NO2


2-501
CH2OCH2CH2OMe
Me
NO2


2-502
CH2OCH2CH2OMe
Et
NO2


2-503
CH2OCH2CH2OMe
n-Pr
NO2


2-504
CH2OCH2CH2OMe
i-Pr
NO2


2-505
CH2OCH2CH2OEt
Me
NO2


2-506
CH2OCH2CH2OEt
Et
NO2


2-507
CH2OCH2CH2OEt
n-Pr
NO2


2-508
CH2OCH2CH2OEt
i-Pr
NO2


2-509
CH2OCH2CH2CH2OMe
Me
NO2


2-510
CH2OCH2CH2CH2OMe
Et
NO2


2-511
CH2OCH2CH2CH2OMe
n-Pr
NO2


2-512
CH2OCH2CH2CH2OMe
i-Pr
NO2


2-513
CH2OCH2OMe
Me
NO2


2-514
CH2OCH2OMe
Et
NO2


2-515
CH2OCH2OMe
n-Pr
NO2


2-516
CH2OCH2OMe
i-Pr
NO2


2-517
CH2OCH2OEt
Me
NO2


2-518
CH2OCH2OEt
Et
NO2


2-519
CH2OCH2OEt
n-Pr
NO2


2-520
CH2OCH2OEt
i-Pr
NO2


2-521
CH2OCH2CH2SO2Me
Me
NO2


2-522
CH2OCH2CH2SO2Me
Et
NO2


2-523
CH2OCH2CH2SO2Me
n-Pr
NO2


2-524
CH2OCH2CH2SO2Me
i-Pr
NO2


2-525
CH2SO2CH2CH2OMe
Me
NO2


2-526
CH2SO2CH2CH2OMe
Et
NO2


2-527
CH2SO2CH2CH2OMe
n-Pr
NO2


2-528
CH2SO2CH2CH2OMe
i-Pr
NO2


2-529
CH2SO2CH2CH2SO2Me
Me
NO2


2-530
CH2SO2CH2CH2SO2Me
Et
NO2


2-531
CH2SO2CH2CH2SO2Me
n-Pr
NO2


2-532
CH2SO2CH2CH2SO2Me
i-Pr
NO2
















TABLE 3







Compounds of the formula (I) according to the invention in which R4 is


hydrogen and R1 and R2 are each methyl.








 















Physical data:


No.
X
R3
Y
1H-NMR: δ [CDCl3]














3-1
Cl
Me
SO2Me



3-2
Cl
Et
SO2Me


3-3
Cl
n-Pr
SO2Me


3-4
Cl
i-Pr
SO2Me


3-5
Br
Me
SO2Me


3-6
Br
Et
SO2Me


3-7
Br
n-Pr
SO2Me


3-8
Br
i-Pr
SO2Me


3-9
Me
Me
SO2Me
8.09 (d, 1H), 7.49 (d,






1H), 3.64 (s, 3H), 3.38






(s, 3H), 3.18 (s, 3H),






2.81 (s, 3H), 1.69 (s,






3H)


3-10
Me
Et
SO2Me


3-11
Me
n-Pr
SO2Me


3-12
Me
i-Pr
SO2Me


3-13
Et
Me
SO2Me


3-14
Et
Et
SO2Me


3-15
Et
n-Pr
SO2Me


3-16
Et
i-Pr
SO2Me


3-17
CF3
Me
SO2Me


3-18
CF3
Et
SO2Me


3-19
CF3
n-Pr
SO2Me


3-20
CF3
i-Pr
SO2Me


3-21
OMe
Me
SO2Me


3-22
OMe
Et
SO2Me


3-23
OMe
n-Pr
SO2Me


3-24
OMe
i-Pr
SO2Me


3-25
OEt
Me
SO2Me


3-26
OEt
Et
SO2Me


3-27
OEt
n-Pr
SO2Me


3-28
OEt
i-Pr
SO2Me


3-29
NO2
Me
SO2Me


3-30
NO2
Et
SO2Me


3-31
NO2
n-Pr
SO2Me


3-32
NO2
i-Pr
SO2Me


3-33
SO2Me
Me
SO2Me


3-34
SO2Me
Et
SO2Me


3-35
SO2Me
n-Pr
SO2Me


3-36
SO2Me
i-Pr
SO2Me


3-37
CH2OMe
Me
SO2Me


3-38
CH2OMe
Et
SO2Me


3-39
CH2OMe
n-Pr
SO2Me


3-40
CH2OMe
i-Pr
SO2Me


3-41
CH2SO2Me
Me
SO2Me


3-42
CH2SO2Me
Et
SO2Me


3-43
CH2SO2Me
n-Pr
SO2Me


3-44
CH2SO2Me
i-Pr
SO2Me


3-45
CH2OCH2CH2OMe
Me
SO2Me


3-46
CH2OCH2CH2OMe
Et
SO2Me


3-47
CH2OCH2CH2OMe
n-Pr
SO2Me


3-48
CH2OCH2CH2OMe
i-Pr
SO2Me


3-49
CH2OCH2CH2OEt
Me
SO2Me


3-50
CH2OCH2CH2OEt
Et
SO2Me


3-51
CH2OCH2CH2OEt
n-Pr
SO2Me


3-52
CH2OCH2CH2OEt
i-Pr
SO2Me


3-53
CH2OCH2CH2CH2OMe
Me
SO2Me


3-54
CH2OCH2CH2CH2OMe
Et
SO2Me


3-55
CH2OCH2CH2CH2OMe
n-Pr
SO2Me


3-56
CH2OCH2CH2CH2OMe
i-Pr
SO2Me


3-57
CH2OCH2OMe
Me
SO2Me


3-58
CH2OCH2OMe
Et
SO2Me


3-59
CH2OCH2OMe
n-Pr
SO2Me


3-60
CH2OCH2OMe
i-Pr
SO2Me


3-61
CH2OCH2OEt
Me
SO2Me


3-62
CH2OCH2OEt
Et
SO2Me


3-63
CH2OCH2OEt
n-Pr
SO2Me


3-64
CH2OCH2OEt
i-Pr
SO2Me


3-65
CH2OCH2CH2SO2Me
Me
SO2Me


3-66
CH2OCH2CH2SO2Me
Et
SO2Me


3-67
CH2OCH2CH2SO2Me
n-Pr
SO2Me


3-68
CH2OCH2CH2SO2Me
i-Pr
SO2Me


3-69
CH2SO2CH2CH2OMe
Me
SO2Me


3-70
CH2SO2CH2CH2OMe
Et
SO2Me


3-71
CH2SO2CH2CH2OMe
n-Pr
SO2Me


3-72
CH2SO2CH2CH2OMe
i-Pr
SO2Me


3-73
CH2SO2CH2CH2SO2Me
Me
SO2Me


3-74
CH2SO2CH2CH2SO2Me
Et
SO2Me


3-75
CH2SO2CH2CH2SO2Me
n-Pr
SO2Me


3-76
CH2SO2CH2CH2SO2Me
i-Pr
SO2Me


3-77
Cl
Me
SO2Et


3-78
Cl
Et
SO2Et


3-79
Cl
n-Pr
SO2Et


3-80
Cl
i-Pr
SO2Et


3-81
Br
Me
SO2Et


3-82
Br
Et
SO2Et


3-83
Br
n-Pr
SO2Et


3-84
Br
i-Pr
SO2Et


3-85
Me
Me
SO2Et


3-86
Me
Et
SO2Et


3-87
Me
n-Pr
SO2Et


3-88
Me
i-Pr
SO2Et


3-89
Et
Me
SO2Et


3-90
Et
Et
SO2Et


3-91
Et
n-Pr
SO2Et


3-92
Et
i-Pr
SO2Et


3-93
CF3
Me
SO2Et


3-94
CF3
Et
SO2Et


3-95
CF3
n-Pr
SO2Et


3-96
CF3
i-Pr
SO2Et


3-97
OMe
Me
SO2Et


3-98
OMe
Et
SO2Et


3-99
OMe
n-Pr
SO2Et


3-100
OMe
i-Pr
SO2Et


3-101
OEt
Me
SO2Et


3-102
OEt
Et
SO2Et


3-103
OEt
n-Pr
SO2Et


3-104
OEt
i-Pr
SO2Et


3-105
NO2
Me
SO2Et


3-106
NO2
Et
SO2Et


3-107
NO2
n-Pr
SO2Et


3-108
NO2
i-Pr
SO2Et


3-109
SO2Me
Me
SO2Et


3-110
SO2Me
Et
SO2Et


3-111
SO2Me
n-Pr
SO2Et


3-112
SO2Me
i-Pr
SO2Et


3-113
CH2OMe
Me
SO2Et


3-114
CH2OMe
Et
SO2Et


3-115
CH2OMe
n-Pr
SO2Et


3-116
CH2OMe
i-Pr
SO2Et


3-117
CH2SO2Me
Me
SO2Et


3-118
CH2SO2Me
Et
SO2Et


3-119
CH2SO2Me
n-Pr
SO2Et


3-120
CH2SO2Me
i-Pr
SO2Et


3-121
CH2OCH2CH2OMe
Me
SO2Et


3-122
CH2OCH2CH2OMe
Et
SO2Et


3-123
CH2OCH2CH2OMe
n-Pr
SO2Et


3-124
CH2OCH2CH2OMe
i-Pr
SO2Et


3-125
CH2OCH2CH2OEt
Me
SO2Et


3-126
CH2OCH2CH2OEt
Et
SO2Et


3-127
CH2OCH2CH2OEt
n-Pr
SO2Et


3-128
CH2OCH2CH2OEt
i-Pr
SO2Et


3-129
CH2OCH2CH2CH2OMe
Me
SO2Et


3-130
CH2OCH2CH2CH2OMe
Et
SO2Et


3-131
CH2OCH2CH2CH2OMe
n-Pr
SO2Et


3-132
CH2OCH2CH2CH2OMe
i-Pr
SO2Et


3-133
CH2OCH2OMe
Me
SO2Et


3-134
CH2OCH2OMe
Et
SO2Et


3-135
CH2OCH2OMe
n-Pr
SO2Et


3-136
CH2OCH2OMe
i-Pr
SO2Et


3-137
CH2OCH2OEt
Me
SO2Et


3-138
CH2OCH2OEt
Et
SO2Et


3-139
CH2OCH2OEt
n-Pr
SO2Et


3-140
CH2OCH2OEt
i-Pr
SO2Et


3-141
CH2OCH2CH2SO2Me
Me
SO2Et


3-142
CH2OCH2CH2SO2Me
Et
SO2Et


3-143
CH2OCH2CH2SO2Me
n-Pr
SO2Et


3-144
CH2OCH2CH2SO2Me
i-Pr
SO2Et


3-145
CH2SO2CH2CH2OMe
Me
SO2Et


3-146
CH2SO2CH2CH2OMe
Et
SO2Et


3-147
CH2SO2CH2CH2OMe
n-Pr
SO2Et


3-148
CH2SO2CH2CH2OMe
i-Pr
SO2Et


3-149
CH2SO2CH2CH2SO2Me
Me
SO2Et


3-150
CH2SO2CH2CH2SO2Me
Et
SO2Et


3-151
CH2SO2CH2CH2SO2Me
n-Pr
SO2Et


3-152
CH2SO2CH2CH2SO2Me
i-Pr
SO2Et


3-153
Cl
Me
F


3-154
Cl
Et
F


3-155
Cl
n-Pr
F


3-156
Cl
i-Pr
F


3-157
Br
Me
F


3-158
Br
Et
F


3-159
Br
n-Pr
F


3-160
Br
i-Pr
F


3-161
Me
Me
F


3-162
Me
Et
F


3-163
Me
n-Pr
F


3-164
Me
i-Pr
F


3-165
Et
Me
F


3-166
Et
Et
F


3-167
Et
n-Pr
F


3-168
Et
i-Pr
F


3-169
CF3
Me
F


3-170
CF3
Et
F


3-171
CF3
n-Pr
F


3-172
CF3
i-Pr
F


3-173
OMe
Me
F


3-174
OMe
Et
F


3-175
OMe
n-Pr
F


3-176
OMe
i-Pr
F


3-177
OEt
Me
F


3-178
OEt
Et
F


3-179
OEt
n-Pr
F


3-180
OEt
i-Pr
F


3-181
NO2
Me
F


3-182
NO2
Et
F


3-183
NO2
n-Pr
F


3-184
NO2
i-Pr
F


3-185
SO2Me
Me
F


3-186
SO2Me
Et
F


3-187
SO2Me
n-Pr
F


3-188
SO2Me
i-Pr
F


3-189
CH2OMe
Me
F


3-190
CH2OMe
Et
F


3-191
CH2OMe
n-Pr
F


3-192
CH2OMe
i-Pr
F


3-193
CH2SO2Me
Me
F


3-194
CH2SO2Me
Et
F


3-195
CH2SO2Me
n-Pr
F


3-196
CH2SO2Me
i-Pr
F


3-197
CH2OCH2CH2OMe
Me
F


3-198
CH2OCH2CH2OMe
Et
F


3-199
CH2OCH2CH2OMe
n-Pr
F


3-200
CH2OCH2CH2OMe
i-Pr
F


3-201
CH2OCH2CH2OEt
Me
F


3-202
CH2OCH2CH2OEt
Et
F


3-203
CH2OCH2CH2OEt
n-Pr
F


3-204
CH2OCH2CH2OEt
i-Pr
F


3-205
CH2OCH2CH2CH2OMe
Me
F


3-206
CH2OCH2CH2CH2OMe
Et
F


3-207
CH2OCH2CH2CH2OMe
n-Pr
F


3-208
CH2OCH2CH2CH2OMe
i-Pr
F


3-209
CH2OCH2OMe
Me
F


3-210
CH2OCH2OMe
Et
F


3-211
CH2OCH2OMe
n-Pr
F


3-212
CH2OCH2OMe
i-Pr
F


3-213
CH2OCH2OEt
Me
F


3-214
CH2OCH2OEt
Et
F


3-215
CH2OCH2OEt
n-Pr
F


3-216
CH2OCH2OEt
i-Pr
F


3-217
CH2OCH2CH2SO2Me
Me
F


3-218
CH2OCH2CH2SO2Me
Et
F


3-219
CH2OCH2CH2SO2Me
n-Pr
F


3-220
CH2OCH2CH2SO2Me
i-Pr
F


3-221
CH2SO2CH2CH2OMe
Me
F


3-222
CH2SO2CH2CH2OMe
Et
F


3-223
CH2SO2CH2CH2OMe
n-Pr
F


3-224
CH2SO2CH2CH2OMe
i-Pr
F


3-225
CH2SO2CH2CH2SO2Me
Me
F


3-226
CH2SO2CH2CH2SO2Me
Et
F


3-227
CH2SO2CH2CH2SO2Me
n-Pr
F


3-228
CH2SO2CH2CH2SO2Me
i-Pr
F


3-229
Cl
Me
Cl


3-230
Cl
Et
Cl


3-231
Cl
n-Pr
Cl


3-232
Cl
i-Pr
Cl


3-233
Br
Me
Cl


3-234
Br
Et
Cl


3-235
Br
n-Pr
Cl


3-236
Br
i-Pr
Cl


3-237
Me
Me
Cl
7.37 (d, 1H), 7.23 (d,






1H), 3.63 (s, 3H), 3.01






(s, 3H), 2.68 (s, 3H),






1.72 (s, 3H)


3-238
Me
Et
Cl
7.37 (d, 1H), 7.23 (d,






1H), 3.63 (s, 3H), 3.36






(m, 1H), 3.16 (m, 1H),






2.63 (s, 3H), 1.72 (s,






3H), 1.40 (t, 3H)


3-239
Me
n-Pr
Cl


3-240
Me
i-Pr
Cl


3-241
Et
Me
Cl


3-242
Et
Et
Cl


3-243
Et
n-Pr
Cl


3-244
Et
i-Pr
Cl


3-245
CF3
Me
Cl


3-246
CF3
Et
Cl


3-247
CF3
n-Pr
Cl


3-248
CF3
i-Pr
Cl


3-249
OMe
Me
Cl


3-250
OMe
Et
Cl


3-251
OMe
n-Pr
Cl


3-252
OMe
i-Pr
Cl


3-253
OEt
Me
Cl


3-254
OEt
Et
Cl


3-255
OEt
n-Pr
Cl


3-256
OEt
i-Pr
Cl


3-257
NO2
Me
Cl


3-258
NO2
Et
Cl


3-259
NO2
n-Pr
Cl


3-260
NO2
i-Pr
Cl


3-261
SO2Me
Me
Cl


3-262
SO2Me
Et
Cl


3-263
SO2Me
n-Pr
Cl


3-264
SO2Me
i-Pr
Cl


3-265
CH2OMe
Me
Cl


3-266
CH2OMe
Et
Cl


3-267
CH2OMe
n-Pr
Cl


3-268
CH2OMe
i-Pr
Cl


3-269
CH2SO2Me
Me
Cl


3-270
CH2SO2Me
Et
Cl


3-271
CH2SO2Me
n-Pr
Cl


3-272
CH2SO2Me
i-Pr
Cl


3-273
CH2OCH2CH2OMe
Me
Cl


3-274
CH2OCH2CH2OMe
Et
Cl


3-275
CH2OCH2CH2OMe
n-Pr
Cl


3-276
CH2OCH2CH2OMe
i-Pr
Cl


3-277
CH2OCH2CH2OEt
Me
Cl


3-278
CH2OCH2CH2OEt
Et
Cl


3-279
CH2OCH2CH2OEt
n-Pr
Cl


3-280
CH2OCH2CH2OEt
i-Pr
Cl


3-281
CH2OCH2CH2CH2OMe
Me
Cl


3-282
CH2OCH2CH2CH2OMe
Et
Cl


3-283
CH2OCH2CH2CH2OMe
n-Pr
Cl


3-284
CH2OCH2CH2CH2OMe
i-Pr
Cl


3-285
CH2OCH2OMe
Me
Cl


3-286
CH2OCH2OMe
Et
Cl


3-287
CH2OCH2OMe
n-Pr
Cl


3-288
CH2OCH2OMe
i-Pr
Cl


3-289
CH2OCH2OEt
Me
Cl


3-290
CH2OCH2OEt
Et
Cl


3-291
CH2OCH2OEt
n-Pr
Cl


3-292
CH2OCH2OEt
i-Pr
Cl


3-293
CH2OCH2CH2SO2Me
Me
Cl


3-294
CH2OCH2CH2SO2Me
Et
Cl


3-295
CH2OCH2CH2SO2Me
n-Pr
Cl


3-296
CH2OCH2CH2SO2Me
i-Pr
Cl


3-297
CH2SO2CH2CH2OMe
Me
Cl


3-298
CH2SO2CH2CH2OMe
Et
Cl


3-299
CH2SO2CH2CH2OMe
n-Pr
Cl


3-300
CH2SO2CH2CH2OMe
i-Pr
Cl


3-301
CH2SO2CH2CH2SO2Me
Me
Cl


3-302
CH2SO2CH2CH2SO2Me
Et
Cl


3-303
CH2SO2CH2CH2SO2Me
n-Pr
Cl


3-304
CH2SO2CH2CH2SO2Me
i-Pr
Cl


3-305
Cl
Me
Br


3-306
Cl
Et
Br


3-307
Cl
n-Pr
Br


3-308
Cl
i-Pr
Br


3-309
Br
Me
Br


3-310
Br
Et
Br


3-311
Br
n-Pr
Br


3-312
Br
i-Pr
Br


3-313
Me
Me
Br
7.57 (d, 1H), 7.16 (d,






1H), 3.67 (s, 3H), 3.02






(s, 3H), 2.69 (s, 3H),






1.75 (s, 3H)


3-314
Me
Et
Br


3-315
Me
n-Pr
Br


3-316
Me
i-Pr
Br


3-317
Et
Me
Br


3-318
Et
Et
Br


3-319
Et
n-Pr
Br


3-320
Et
i-Pr
Br


3-321
CF3
Me
Br


3-322
CF3
Et
Br


3-323
CF3
n-Pr
Br


3-324
CF3
i-Pr
Br


3-325
OMe
Me
Br


3-326
OMe
Et
Br


3-327
OMe
n-Pr
Br


3-328
OMe
i-Pr
Br


3-329
OEt
Me
Br


3-330
OEt
Et
Br


3-331
OEt
n-Pr
Br


3-332
OEt
i-Pr
Br


3-333
NO2
Me
Br


3-334
NO2
Et
Br


3-335
NO2
n-Pr
Br


3-336
NO2
i-Pr
Br


3-337
SO2Me
Me
Br


3-338
SO2Me
Et
Br


3-339
SO2Me
n-Pr
Br


3-340
SO2Me
i-Pr
Br


3-341
CH2OMe
Me
Br


3-342
CH2OMe
Et
Br


3-343
CH2OMe
n-Pr
Br


3-344
CH2OMe
i-Pr
Br


3-345
CH2SO2Me
Me
Br


3-346
CH2SO2Me
Et
Br


3-347
CH2SO2Me
n-Pr
Br


3-348
CH2SO2Me
i-Pr
Br


3-349
CH2OCH2CH2OMe
Me
Br


3-350
CH2OCH2CH2OMe
Et
Br


3-351
CH2OCH2CH2OMe
n-Pr
Br


3-352
CH2OCH2CH2OMe
i-Pr
Br


3-353
CH2OCH2CH2OEt
Me
Br


3-354
CH2OCH2CH2OEt
Et
Br


3-355
CH2OCH2CH2OEt
n-Pr
Br


3-356
CH2OCH2CH2OEt
i-Pr
Br


3-357
CH2OCH2CH2CH2OMe
Me
Br


3-358
CH2OCH2CH2CH2OMe
Et
Br


3-359
CH2OCH2CH2CH2OMe
n-Pr
Br


3-360
CH2OCH2CH2CH2OMe
i-Pr
Br


3-361
CH2OCH2OMe
Me
Br


3-362
CH2OCH2OMe
Et
Br


3-363
CH2OCH2OMe
n-Pr
Br


3-364
CH2OCH2OMe
i-Pr
Br


3-365
CH2OCH2OEt
Me
Br


3-366
CH2OCH2OEt
Et
Br


3-367
CH2OCH2OEt
n-Pr
Br


3-368
CH2OCH2OEt
i-Pr
Br


3-369
CH2OCH2CH2SO2Me
Me
Br


3-370
CH2OCH2CH2SO2Me
Et
Br


3-371
CH2OCH2CH2SO2Me
n-Pr
Br


3-372
CH2OCH2CH2SO2Me
i-Pr
Br


3-373
CH2SO2CH2CH2OMe
Me
Br


3-374
CH2SO2CH2CH2OMe
Et
Br


3-375
CH2SO2CH2CH2OMe
n-Pr
Br


3-376
CH2SO2CH2CH2OMe
i-Pr
Br


3-377
CH2SO2CH2CH2SO2Me
Me
Br


3-378
CH2SO2CH2CH2SO2Me
Et
Br


3-379
CH2SO2CH2CH2SO2Me
n-Pr
Br


3-380
CH2SO2CH2CH2SO2Me
i-Pr
Br


3-381
Cl
Me
I


3-382
Cl
Et
I


3-383
Cl
n-Pr
I


3-384
Cl
i-Pr
I


3-385
Br
Me
I


3-386
Br
Et
I


3-387
Br
n-Pr
I


3-388
Br
i-Pr
I


3-389
Me
Me
I
7.68 (d, 1H), 6.96 (d,






1H), 3.65 (s, 3H), 2.96






(s, 3H), 2.68 (s, 3H),






1.74 (s, 3H)


3-390
Me
Et
I


3-391
Me
n-Pr
I


3-392
Me
i-Pr
I


3-393
Et
Me
I


3-394
Et
Et
I


3-395
Et
n-Pr
I


3-396
Et
i-Pr
I


3-397
CF3
Me
I


3-398
CF3
Et
I


3-399
CF3
n-Pr
I


3-400
CF3
i-Pr
I


3-401
OMe
Me
I


3-402
OMe
Et
I


3-403
OMe
n-Pr
I


3-404
OMe
i-Pr
I


3-405
OEt
Me
I


3-406
OEt
Et
I


3-407
OEt
n-Pr
I


3-408
OEt
i-Pr
I


3-409
NO2
Me
I


3-410
NO2
Et
I


3-411
NO2
n-Pr
I


3-412
NO2
i-Pr
I


3-413
SO2Me
Me
I


3-414
SO2Me
Et
I


3-415
SO2Me
n-Pr
I


3-416
SO2Me
i-Pr
I


3-417
CH2OMe
Me
I


3-418
CH2OMe
Et
I


3-419
CH2OMe
n-Pr
I


3-420
CH2OMe
i-Pr
I


3-421
CH2SO2Me
Me
I


3-422
CH2SO2Me
Et
I


3-423
CH2SO2Me
n-Pr
I


3-424
CH2SO2Me
i-Pr
I


3-425
CH2OCH2CH2OMe
Me
I


3-426
CH2OCH2CH2OMe
Et
I


3-427
CH2OCH2CH2OMe
n-Pr
I


3-428
CH2OCH2CH2OMe
i-Pr
I


3-429
CH2OCH2CH2OEt
Me
I


3-430
CH2OCH2CH2OEt
Et
I


3-431
CH2OCH2CH2OEt
n-Pr
I


3-432
CH2OCH2CH2OEt
i-Pr
I


3-433
CH2OCH2CH2CH2OMe
Me
I


3-434
CH2OCH2CH2CH2OMe
Et
I


3-435
CH2OCH2CH2CH2OMe
n-Pr
I


3-436
CH2OCH2CH2CH2OMe
i-Pr
I


3-437
CH2OCH2OMe
Me
I


3-438
CH2OCH2OMe
Et
I


3-439
CH2OCH2OMe
n-Pr
I


3-440
CH2OCH2OMe
i-Pr
I


3-441
CH2OCH2OEt
Me
I


3-442
CH2OCH2OEt
Et
I


3-443
CH2OCH2OEt
n-Pr
I


3-444
CH2OCH2OEt
i-Pr
I


3-445
CH2OCH2CH2SO2Me
Me
I


3-446
CH2OCH2CH2SO2Me
Et
I


3-447
CH2OCH2CH2SO2Me
n-Pr
I


3-448
CH2OCH2CH2SO2Me
i-Pr
I


3-449
CH2SO2CH2CH2OMe
Me
I


3-450
CH2SO2CH2CH2OMe
Et
I


3-451
CH2SO2CH2CH2OMe
n-Pr
I


3-452
CH2SO2CH2CH2OMe
i-Pr
I


3-453
CH2SO2CH2CH2SO2Me
Me
I


3-454
CH2SO2CH2CH2SO2Me
Et
I


3-455
CH2SO2CH2CH2SO2Me
n-Pr
I


3-456
CH2SO2CH2CH2SO2Me
i-Pr
I


3-457
Cl
Me
NO2


3-458
Cl
Et
NO2


3-459
Cl
n-Pr
NO2


3-460
Cl
i-Pr
NO2


3-461
Br
Me
NO2


3-462
Br
Et
NO2


3-463
Br
n-Pr
NO2


3-464
Br
i-Pr
NO2


3-465
Me
Me
NO2


3-466
Me
Et
NO2


3-467
Me
n-Pr
NO2


3-468
Me
i-Pr
NO2


3-469
Et
Me
NO2


3-470
Et
Et
NO2


3-471
Et
n-Pr
NO2


3-472
Et
i-Pr
NO2


3-473
CF3
Me
NO2


3-474
CF3
Et
NO2


3-475
CF3
n-Pr
NO2


3-476
CF3
i-Pr
NO2


3-477
OMe
Me
NO2


3-478
OMe
Et
NO2


3-479
OMe
n-Pr
NO2


3-480
OMe
i-Pr
NO2


3-481
OEt
Me
NO2


3-482
OEt
Et
NO2


3-483
OEt
n-Pr
NO2


3-484
OEt
i-Pr
NO2


3-485
NO2
Me
NO2


3-486
NO2
Et
NO2


3-487
NO2
n-Pr
NO2


3-488
NO2
i-Pr
NO2


3-489
SO2Me
Me
NO2


3-490
SO2Me
Et
NO2


3-491
SO2Me
n-Pr
NO2


3-492
SO2Me
i-Pr
NO2


3-493
CH2OMe
Me
NO2


3-494
CH2OMe
Et
NO2


3-495
CH2OMe
n-Pr
NO2


3-496
CH2OMe
i-Pr
NO2


3-497
CH2SO2Me
Me
NO2


3-498
CH2SO2Me
Et
NO2


3-499
CH2SO2Me
n-Pr
NO2


3-500
CH2SO2Me
i-Pr
NO2


3-501
CH2OCH2CH2OMe
Me
NO2


3-502
CH2OCH2CH2OMe
Et
NO2


3-503
CH2OCH2CH2OMe
n-Pr
NO2


3-504
CH2OCH2CH2OMe
i-Pr
NO2


3-505
CH2OCH2CH2OEt
Me
NO2


3-506
CH2OCH2CH2OEt
Et
NO2


3-507
CH2OCH2CH2OEt
n-Pr
NO2


3-508
CH2OCH2CH2OEt
i-Pr
NO2


3-509
CH2OCH2CH2CH2OMe
Me
NO2


3-510
CH2OCH2CH2CH2OMe
Et
NO2


3-511
CH2OCH2CH2CH2OMe
n-Pr
NO2


3-512
CH2OCH2CH2CH2OMe
i-Pr
NO2


3-513
CH2OCH2OMe
Me
NO2


3-514
CH2OCH2OMe
Et
NO2


3-515
CH2OCH2OMe
n-Pr
NO2


3-516
CH2OCH2OMe
i-Pr
NO2


3-517
CH2OCH2OEt
Me
NO2


3-518
CH2OCH2OEt
Et
NO2


3-519
CH2OCH2OEt
n-Pr
NO2


3-520
CH2OCH2OEt
i-Pr
NO2


3-521
CH2OCH2CH2SO2Me
Me
NO2


3-522
CH2OCH2CH2SO2Me
Et
NO2


3-523
CH2OCH2CH2SO2Me
n-Pr
NO2


3-524
CH2OCH2CH2SO2Me
i-Pr
NO2


3-525
CH2SO2CH2CH2OMe
Me
NO2


3-526
CH2SO2CH2CH2OMe
Et
NO2


3-527
CH2SO2CH2CH2OMe
n-Pr
NO2


3-528
CH2SO2CH2CH2OMe
i-Pr
NO2


3-529
CH2SO2CH2CH2SO2Me
Me
NO2


3-530
CH2SO2CH2CH2SO2Me
Et
NO2


3-531
CH2SO2CH2CH2SO2Me
n-Pr
NO2


3-532
CH2SO2CH2CH2SO2Me
i-Pr
NO2
















TABLE 4







Compounds of the formula (II) according to the invention









(II)








 















Physical data:


No.
X
R3
Y
1H-NMR: δ [CDCl3]





4-1 
Cl
Me
SO2Me



4-2 
Cl
Et
SO2Me


4-3 
Cl
n-Pr
SO2Me


4-4 
Cl
i-Pr
SO2Me


4-5 
Br
Me
SO2Me


4-6 
Br
Et
SO2Me


4-7 
Br
n-Pr
SO2Me


4-8 
Br
i-Pr
SO2Me


4-9 
Me
Me
SO2Me
(DMSO-d6): 7.93 (s, 2H), 3.46 (s,






3H), 3.08 (s, 3H), 2.87 (s, 3H)


4-10 
Me
Et
SO2Me
(DMSO-d6): 7.93 (s, 2H), 3.47 (m,






1H), 3.46 (s, 3H), 3.08 (m, 1H),






2.82 (s, 3H), 1.33 (t, 3H)


4-11 
Me
n-Pr
SO2Me


4-12 
Me
i-Pr
SO2Me


4-13 
Et
Me
SO2Me


4-14 
Et
Et
SO2Me


4-15 
Et
n-Pr
SO2Me


4-16 
Et
i-Pr
SO2Me


4-17 
CF3
Me
SO2Me


4-18 
CF3
Et
SO2Me


4-19 
CF3
n-Pr
SO2Me


4-20 
CF3
i-Pr
SO2Me


4-21 
OMe
Me
SO2Me


4-22 
OMe
Et
SO2Me


4-23 
OMe
n-Pr
SO2Me


4-24 
OMe
i-Pr
SO2Me


4-25 
OEt
Me
SO2Me


4-26 
OEt
Et
SO2Me


4-27 
OEt
n-Pr
SO2Me


4-28 
OEt
i-Pr
SO2Me


4-29 
NO2
Me
SO2Me


4-30 
NO2
Et
SO2Me


4-31 
NO2
n-Pr
SO2Me


4-32 
NO2
i-Pr
SO2Me


4-33 
SO2Me
Me
SO2Me


4-34 
SO2Me
Et
SO2Me


4-35 
SO2Me
n-Pr
SO2Me


4-36 
SO2Me
i-Pr
SO2Me


4-37 
CH2OMe
Me
SO2Me


4-38 
CH2OMe
Et
SO2Me


4-39 
CH2OMe
n-Pr
SO2Me


4-40 
CH2OMe
i-Pr
SO2Me


4-41 
CH2SO2Me
Me
SO2Me


4-42 
CH2SO2Me
Et
SO2Me


4-43 
CH2SO2Me
n-Pr
SO2Me


4-44 
CH2SO2Me
i-Pr
SO2Me


4-45 
CH2OCH2CH2OMe
Me
SO2Me


4-46 
CH2OCH2CH2OMe
Et
SO2Me


4-47 
CH2OCH2CH2OMe
n-Pr
SO2Me


4-48 
CH2OCH2CH2OMe
i-Pr
SO2Me


4-49 
CH2OCH2CH2OEt
Me
SO2Me


4-50 
CH2OCH2CH2OEt
Et
SO2Me


4-51 
CH2OCH2CH2OEt
n-Pr
SO2Me


4-52 
CH2OCH2CH2OEt
i-Pr
SO2Me


4-53 
CH2OCH2CH2CH2OMe
Me
SO2Me


4-54 
CH2OCH2CH2CH2OMe
Et
SO2Me


4-55 
CH2OCH2CH2CH2OMe
n-Pr
SO2Me


4-56 
CH2OCH2CH2CH2OMe
i-Pr
SO2Me


4-57 
CH2OCH2OMe
Me
SO2Me


4-58 
CH2OCH2OMe
Et
SO2Me


4-59 
CH2OCH2OMe
n-Pr
SO2Me


4-60 
CH2OCH2OMe
i-Pr
SO2Me


4-61 
CH2OCH2OEt
Me
SO2Me


4-62 
CH2OCH2OEt
Et
SO2Me


4-63 
CH2OCH2OEt
n-Pr
SO2Me


4-64 
CH2OCH2OEt
i-Pr
SO2Me


4-65 
CH2OCH2CH2SO2Me
Me
SO2Me


4-66 
CH2OCH2CH2SO2Me
Et
SO2Me


4-67 
CH2OCH2CH2SO2Me
n-Pr
SO2Me


4-68 
CH2OCH2CH2SO2Me
i-Pr
SO2Me


4-69 
CH2SO2CH2CH2OMe
Me
SO2Me


4-70 
CH2SO2CH2CH2OMe
Et
SO2Me


4-71 
CH2SO2CH2CH2OMe
n-Pr
SO2Me


4-72 
CH2SO2CH2CH2OMe
i-Pr
SO2Me


4-73 
CH2SO2CH2CH2SO2Me
Me
SO2Me


4-74 
CH2SO2CH2CH2SO2Me
Et
SO2Me


4-75 
CH2SO2CH2CH2SO2Me
n-Pr
SO2Me


4-76 
CH2SO2CH2CH2SO2Me
i-Pr
SO2Me


4-77 
Cl
Me
SO2Et


4-78 
Cl
Et
SO2Et


4-79 
Cl
n-Pr
SO2Et


4-80 
Cl
i-Pr
SO2Et


4-81 
Br
Me
SO2Et


4-82 
Br
Et
SO2Et


4-83 
Br
n-Pr
SO2Et


4-84 
Br
i-Pr
SO2Et


4-85 
Me
Me
SO2Et


4-86 
Me
Et
SO2Et


4-87 
Me
n-Pr
SO2Et


4-88 
Me
i-Pr
SO2Et


4-89 
Et
Me
SO2Et


4-90 
Et
Et
SO2Et


4-91 
Et
n-Pr
SO2Et


4-92 
Et
i-Pr
SO2Et


4-93 
CF3
Me
SO2Et


4-94 
CF3
Et
SO2Et


4-95 
CF3
n-Pr
SO2Et


4-96 
CF3
i-Pr
SO2Et


4-97 
OMe
Me
SO2Et


4-98 
OMe
Et
SO2Et


4-99 
OMe
n-Pr
SO2Et


4-100
OMe
i-Pr
SO2Et


4-101
OEt
Me
SO2Et


4-102
OEt
Et
SO2Et


4-103
OEt
n-Pr
SO2Et


4-104
OEt
i-Pr
SO2Et


4-105
NO2
Me
SO2Et


4-106
NO2
Et
SO2Et


4-107
NO2
n-Pr
SO2Et


4-108
NO2
i-Pr
SO2Et


4-109
SO2Me
Me
SO2Et


4-110
SO2Me
Et
SO2Et


4-111
SO2Me
n-Pr
SO2Et


4-112
SO2Me
i-Pr
SO2Et


4-113
CH2OMe
Me
SO2Et


4-114
CH2OMe
Et
SO2Et


4-115
CH2OMe
n-Pr
SO2Et


4-116
CH2OMe
i-Pr
SO2Et


4-117
CH2SO2Me
Me
SO2Et


4-118
CH2SO2Me
Et
SO2Et


4-119
CH2SO2Me
n-Pr
SO2Et


4-120
CH2SO2Me
i-Pr
SO2Et


4-121
CH2OCH2CH2OMe
Me
SO2Et


4-122
CH2OCH2CH2OMe
Et
SO2Et


4-123
CH2OCH2CH2OMe
n-Pr
SO2Et


4-124
CH2OCH2CH2OMe
i-Pr
SO2Et


4-125
CH2OCH2CH2OEt
Me
SO2Et


4-126
CH2OCH2CH2OEt
Et
SO2Et


4-127
CH2OCH2CH2OEt
n-Pr
SO2Et


4-128
CH2OCH2CH2OEt
i-Pr
SO2Et


4-129
CH2OCH2CH2CH2OMe
Me
SO2Et


4-130
CH2OCH2CH2CH2OMe
Et
SO2Et


4-131
CH2OCH2CH2CH2OMe
n-Pr
SO2Et


4-132
CH2OCH2CH2CH2OMe
i-Pr
SO2Et


4-133
CH2OCH2OMe
Me
SO2Et


4-134
CH2OCH2OMe
Et
SO2Et


4-135
CH2OCH2OMe
n-Pr
SO2Et


4-136
CH2OCH2OMe
i-Pr
SO2Et


4-137
CH2OCH2OEt
Me
SO2Et


4-138
CH2OCH2OEt
Et
SO2Et


4-139
CH2OCH2OEt
n-Pr
SO2Et


4-140
CH2OCH2OEt
i-Pr
SO2Et


4-141
CH2OCH2CH2SO2Me
Me
SO2Et


4-142
CH2OCH2CH2SO2Me
Et
SO2Et


4-143
CH2OCH2CH2SO2Me
n-Pr
SO2Et


4-144
CH2OCH2CH2SO2Me
i-Pr
SO2Et


4-145
CH2SO2CH2CH2OMe
Me
SO2Et


4-146
CH2SO2CH2CH2OMe
Et
SO2Et


4-147
CH2SO2CH2CH2OMe
n-Pr
SO2Et


4-148
CH2SO2CH2CH2OMe
i-Pr
SO2Et


4-149
CH2SO2CH2CH2SO2Me
Me
SO2Et


4-150
CH2SO2CH2CH2SO2Me
Et
SO2Et


4-151
CH2SO2CH2CH2SO2Me
n-Pr
SO2Et


4-152
CH2SO2CH2CH2SO2Me
i-Pr
SO2Et


4-153
Cl
Me
F


4-154
Cl
Et
F


4-155
Cl
n-Pr
F


4-156
Cl
i-Pr
F


4-157
Br
Me
F


4-158
Br
Et
F


4-159
Br
n-Pr
F


4-160
Br
i-Pr
F


4-161
Me
Me
F


4-162
Me
Et
F


4-163
Me
n-Pr
F


4-164
Me
i-Pr
F


4-165
Et
Me
F


4-166
Et
Et
F


4-167
Et
n-Pr
F


4-168
Et
i-Pr
F


4-169
CF3
Me
F


4-170
CF3
Et
F


4-171
CF3
n-Pr
F


4-172
CF3
i-Pr
F


4-173
OMe
Me
F


4-174
OMe
Et
F


4-175
OMe
n-Pr
F


4-176
OMe
i-Pr
F


4-177
OEt
Me
F


4-178
OEt
Et
F


4-179
OEt
n-Pr
F


4-180
OEt
i-Pr
F


4-181
NO2
Me
F


4-182
NO2
Et
F


4-183
NO2
n-Pr
F


4-184
NO2
i-Pr
F


4-185
SO2Me
Me
F


4-186
SO2Me
Et
F


4-187
SO2Me
n-Pr
F


4-188
SO2Me
i-Pr
F


4-189
CH2OMe
Me
F


4-190
CH2OMe
Et
F


4-191
CH2OMe
n-Pr
F


4-192
CH2OMe
i-Pr
F


4-193
CH2SO2Me
Me
F


4-194
CH2SO2Me
Et
F


4-195
CH2SO2Me
n-Pr
F


4-196
CH2SO2Me
i-Pr
F


4-197
CH2OCH2CH2OMe
Me
F


4-198
CH2OCH2CH2OMe
Et
F


4-199
CH2OCH2CH2OMe
n-Pr
F


4-200
CH2OCH2CH2OMe
i-Pr
F


4-201
CH2OCH2CH2OEt
Me
F


4-202
CH2OCH2CH2OEt
Et
F


4-203
CH2OCH2CH2OEt
n-Pr
F


4-204
CH2OCH2CH2OEt
i-Pr
F


4-205
CH2OCH2CH2CH2OMe
Me
F


4-206
CH2OCH2CH2CH2OMe
Et
F


4-207
CH2OCH2CH2CH2OMe
n-Pr
F


4-208
CH2OCH2CH2CH2OMe
i-Pr
F


4-209
CH2OCH2OMe
Me
F


4-210
CH2OCH2OMe
Et
F


4-211
CH2OCH2OMe
n-Pr
F


4-212
CH2OCH2OMe
i-Pr
F


4-213
CH2OCH2OEt
Me
F


4-214
CH2OCH2OEt
Et
F


4-215
CH2OCH2OEt
n-Pr
F


4-216
CH2OCH2OEt
i-Pr
F


4-217
CH2OCH2CH2SO2Me
Me
F


4-218
CH2OCH2CH2SO2Me
Et
F


4-219
CH2OCH2CH2SO2Me
n-Pr
F


4-220
CH2OCH2CH2SO2Me
i-Pr
F


4-221
CH2SO2CH2CH2OMe
Me
F


4-222
CH2SO2CH2CH2OMe
Et
F


4-223
CH2SO2CH2CH2OMe
n-Pr
F


4-224
CH2SO2CH2CH2OMe
i-Pr
F


4-225
CH2SO2CH2CH2SO2Me
Me
F


4-226
CH2SO2CH2CH2SO2Me
Et
F


4-227
CH2SO2CH2CH2SO2Me
n-Pr
F


4-228
CH2SO2CH2CH2SO2Me
i-Pr
F


4-229
Cl
Me
Cl


4-230
Cl
Et
Cl


4-231
Cl
n-Pr
Cl


4-232
Cl
i-Pr
Cl


4-233
Br
Me
Cl


4-234
Br
Et
Cl


4-235
Br
n-Pr
Cl


4-236
Br
i-Pr
Cl


4-237
Me
Me
Cl
(DMSO-d6): 7.77 (d, 1H), 7.47 (d,






1H), 3.01 (s, 3H), 2.78 (s, 3H)


4-238
Me
Et
Cl
7.92 (d, 1H), 7.35 (d, 1H), 3.39 (m,






1H), 3.16 (m, 1H), 2.92 (s, 3H),






1.38 (t, 3H)


4-239
Me
n-Pr
Cl


4-240
Me
i-Pr
Cl


4-241
Et
Me
Cl


4-242
Et
Et
Cl


4-243
Et
n-Pr
Cl


4-244
Et
i-Pr
Cl


4-245
CF3
Me
Cl


4-246
CF3
Et
Cl


4-247
CF3
n-Pr
Cl


4-248
CF3
i-Pr
Cl


4-249
OMe
Me
Cl


4-250
OMe
Et
Cl


4-251
OMe
n-Pr
Cl


4-252
OMe
i-Pr
Cl


4-253
OEt
Me
Cl


4-254
OEt
Et
Cl


4-255
OEt
n-Pr
Cl


4-256
OEt
i-Pr
Cl


4-257
NO2
Me
Cl


4-258
NO2
Et
Cl


4-259
NO2
n-Pr
Cl


4-260
NO2
i-Pr
Cl


4-261
SO2Me
Me
Cl


4-262
SO2Me
Et
Cl


4-263
SO2Me
n-Pr
Cl


4-264
SO2Me
i-Pr
Cl


4-265
CH2OMe
Me
Cl


4-266
CH2OMe
Et
Cl


4-267
CH2OMe
n-Pr
Cl


4-268
CH2OMe
i-Pr
Cl


4-269
CH2SO2Me
Me
Cl


4-270
CH2SO2Me
Et
Cl


4-271
CH2SO2Me
n-Pr
Cl


4-272
CH2SO2Me
i-Pr
Cl


4-273
CH2OCH2CH2OMe
Me
Cl


4-274
CH2OCH2CH2OMe
Et
Cl


4-275
CH2OCH2CH2OMe
n-Pr
Cl


4-276
CH2OCH2CH2OMe
i-Pr
Cl


4-277
CH2OCH2CH2OEt
Me
Cl


4-278
CH2OCH2CH2OEt
Et
Cl


4-279
CH2OCH2CH2OEt
n-Pr
Cl


4-280
CH2OCH2CH2OEt
i-Pr
Cl


4-281
CH2OCH2CH2CH2OMe
Me
Cl


4-282
CH2OCH2CH2CH2OMe
Et
Cl


4-283
CH2OCH2CH2CH2OMe
n-Pr
Cl


4-284
CH2OCH2CH2CH2OMe
i-Pr
Cl


4-285
CH2OCH2OMe
Me
Cl


4-286
CH2OCH2OMe
Et
Cl


4-287
CH2OCH2OMe
n-Pr
Cl


4-288
CH2OCH2OMe
i-Pr
Cl


4-289
CH2OCH2OEt
Me
Cl


4-290
CH2OCH2OEt
Et
Cl


4-291
CH2OCH2OEt
n-Pr
Cl


4-292
CH2OCH2OEt
i-Pr
Cl


4-293
CH2OCH2CH2SO2Me
Me
Cl


4-294
CH2OCH2CH2SO2Me
Et
Cl


4-295
CH2OCH2CH2SO2Me
n-Pr
Cl


4-296
CH2OCH2CH2SO2Me
i-Pr
Cl


4-297
CH2SO2CH2CH2OMe
Me
Cl


4-298
CH2SO2CH2CH2OMe
Et
Cl


4-299
CH2SO2CH2CH2OMe
n-Pr
Cl


4-300
CH2SO2CH2CH2OMe
i-Pr
Cl


4-301
CH2SO2CH2CH2SO2Me
Me
Cl


4-302
CH2SO2CH2CH2SO2Me
Et
Cl


4-303
CH2SO2CH2CH2SO2Me
n-Pr
Cl


4-304
CH2SO2CH2CH2SO2Me
i-Pr
Cl


4-305
Cl
Me
Br


4-306
Cl
Et
Br


4-307
Cl
n-Pr
Br


4-308
Cl
i-Pr
Br


4-309
Br
Me
Br


4-310
Br
Et
Br


4-311
Br
n-Pr
Br


4-312
Br
i-Pr
Br


4-313
Me
Me
Br
(DMSO-d6): 7.66 (d, 1H), 7.64 (d,






1H), 2.99 (s, 3H), 2.80 (s, 3H)


4-314
Me
Et
Br


4-315
Me
n-Pr
Br


4-316
Me
i-Pr
Br


4-317
Et
Me
Br


4-318
Et
Et
Br


4-319
Et
n-Pr
Br


4-320
Et
i-Pr
Br


4-321
CF3
Me
Br


4-322
CF3
Et
Br


4-323
CF3
n-Pr
Br


4-324
CF3
i-Pr
Br


4-325
OMe
Me
Br


4-326
OMe
Et
Br


4-327
OMe
n-Pr
Br


4-328
OMe
i-Pr
Br


4-329
OEt
Me
Br


4-330
OEt
Et
Br


4-331
OEt
n-Pr
Br


4-332
OEt
i-Pr
Br


4-333
NO2
Me
Br


4-334
NO2
Et
Br


4-335
NO2
n-Pr
Br


4-336
NO2
i-Pr
Br


4-337
SO2Me
Me
Br


4-338
SO2Me
Et
Br


4-339
SO2Me
n-Pr
Br


4-340
SO2Me
i-Pr
Br


4-341
CH2OMe
Me
Br


4-342
CH2OMe
Et
Br


4-343
CH2OMe
n-Pr
Br


4-344
CH2OMe
i-Pr
Br


4-345
CH2SO2Me
Me
Br


4-346
CH2SO2Me
Et
Br


4-347
CH2SO2Me
n-Pr
Br


4-348
CH2SO2Me
i-Pr
Br


4-349
CH2OCH2CH2OMe
Me
Br


4-350
CH2OCH2CH2OMe
Et
Br


4-351
CH2OCH2CH2OMe
n-Pr
Br


4-352
CH2OCH2CH2OMe
i-Pr
Br


4-353
CH2OCH2CH2OEt
Me
Br


4-354
CH2OCH2CH2OEt
Et
Br


4-355
CH2OCH2CH2OEt
n-Pr
Br


4-356
CH2OCH2CH2OEt
i-Pr
Br


4-357
CH2OCH2CH2CH2OMe
Me
Br


4-358
CH2OCH2CH2CH2OMe
Et
Br


4-359
CH2OCH2CH2CH2OMe
n-Pr
Br


4-360
CH2OCH2CH2CH2OMe
i-Pr
Br


4-361
CH2OCH2OMe
Me
Br


4-362
CH2OCH2OMe
Et
Br


4-363
CH2OCH2OMe
n-Pr
Br


4-364
CH2OCH2OMe
i-Pr
Br


4-365
CH2OCH2OEt
Me
Br


4-366
CH2OCH2OEt
Et
Br


4-367
CH2OCH2OEt
n-Pr
Br


4-368
CH2OCH2OEt
i-Pr
Br


4-369
CH2OCH2CH2SO2Me
Me
Br


4-370
CH2OCH2CH2SO2Me
Et
Br


4-371
CH2OCH2CH2SO2Me
n-Pr
Br


4-372
CH2OCH2CH2SO2Me
i-Pr
Br


4-373
CH2SO2CH2CH2OMe
Me
Br


4-374
CH2SO2CH2CH2OMe
Et
Br


4-375
CH2SO2CH2CH2OMe
n-Pr
Br


4-376
CH2SO2CH2CH2OMe
i-Pr
Br


4-377
CH2SO2CH2CH2SO2Me
Me
Br


4-378
CH2SO2CH2CH2SO2Me
Et
Br


4-379
CH2SO2CH2CH2SO2Me
n-Pr
Br


4-380
CH2SO2CH2CH2SO2Me
i-Pr
Br


4-381
Cl
Me
I


4-382
Cl
Et
I


4-383
Cl
n-Pr
I


4-384
Cl
i-Pr
I


4-385
Br
Me
I


4-386
Br
Et
I


4-387
Br
n-Pr
I


4-388
Br
i-Pr
I


4-389
Me
Me
I
7.87 (d, 1H), 7.61 (d, 1H), 2.99 (s,






3H), 2.98 (s, 3H)


4-390
Me
Et
I


4-391
Me
n-Pr
I


4-392
Me
i-Pr
I


4-393
Et
Me
I


4-394
Et
Et
I


4-395
Et
n-Pr
I


4-396
Et
i-Pr
I


4-397
CF3
Me
I


4-398
CF3
Et
I


4-399
CF3
n-Pr
I


4-400
CF3
i-Pr
I


4-401
OMe
Me
I


4-402
OMe
Et
I


4-403
OMe
n-Pr
I


4-404
OMe
i-Pr
I


4-405
OEt
Me
I


4-406
OEt
Et
I


4-407
OEt
n-Pr
I


4-408
OEt
i-Pr
I


4-409
NO2
Me
I


4-410
NO2
Et
I


4-411
NO2
n-Pr
I


4-412
NO2
i-Pr
I


4-413
SO2Me
Me
I


4-414
SO2Me
Et
I


4-415
SO2Me
n-Pr
I


4-416
SO2Me
i-Pr
I


4-417
CH2OMe
Me
I


4-418
CH2OMe
Et
I


4-419
CH2OMe
n-Pr
I


4-420
CH2OMe
i-Pr
I


4-421
CH2SO2Me
Me
I


4-422
CH2SO2Me
Et
I


4-423
CH2SO2Me
n-Pr
I


4-424
CH2SO2Me
i-Pr
I


4-425
CH2OCH2CH2OMe
Me
I


4-426
CH2OCH2CH2OMe
Et
I


4-427
CH2OCH2CH2OMe
n-Pr
I


4-428
CH2OCH2CH2OMe
i-Pr
I


4-429
CH2OCH2CH2OEt
Me
I


4-430
CH2OCH2CH2OEt
Et
I


4-431
CH2OCH2CH2OEt
n-Pr
I


4-432
CH2OCH2CH2OEt
i-Pr
I


4-433
CH2OCH2CH2CH2OMe
Me
I


4-434
CH2OCH2CH2CH2OMe
Et
I


4-435
CH2OCH2CH2CH2OMe
n-Pr
I


4-436
CH2OCH2CH2CH2OMe
i-Pr
I


4-437
CH2OCH2OMe
Me
I


4-438
CH2OCH2OMe
Et
I


4-439
CH2OCH2OMe
n-Pr
I


4-440
CH2OCH2OMe
i-Pr
I


4-441
CH2OCH2OEt
Me
I


4-442
CH2OCH2OEt
Et
I


4-443
CH2OCH2OEt
n-Pr
I


4-444
CH2OCH2OEt
i-Pr
I


4-445
CH2OCH2CH2SO2Me
Me
I


4-446
CH2OCH2CH2SO2Me
Et
I


4-447
CH2OCH2CH2SO2Me
n-Pr
I


4-448
CH2OCH2CH2SO2Me
i-Pr
I


4-449
CH2SO2CH2CH2OMe
Me
I


4-450
CH2SO2CH2CH2OMe
Et
I


4-451
CH2SO2CH2CH2OMe
n-Pr
I


4-452
CH2SO2CH2CH2OMe
i-Pr
I


4-453
CH2SO2CH2CH2SO2Me
Me
I


4-454
CH2SO2CH2CH2SO2Me
Et
I


4-455
CH2SO2CH2CH2SO2Me
n-Pr
I


4-456
CH2SO2CH2CH2SO2Me
i-Pr
I


4-457
Cl
Me
NO2


4-458
Cl
Et
NO2


4-459
Cl
n-Pr
NO2


4-460
Cl
i-Pr
NO2


4-461
Br
Me
NO2


4-462
Br
Et
NO2


4-463
Br
n-Pr
NO2


4-464
Br
i-Pr
NO2


4-465
Me
Me
NO2


4-466
Me
Et
NO2


4-467
Me
n-Pr
NO2


4-468
Me
i-Pr
NO2


4-469
Et
Me
NO2


4-470
Et
Et
NO2


4-471
Et
n-Pr
NO2


4-472
Et
i-Pr
NO2


4-473
CF3
Me
NO2


4-474
CF3
Et
NO2


4-475
CF3
n-Pr
NO2


4-476
CF3
i-Pr
NO2


4-477
OMe
Me
NO2


4-478
OMe
Et
NO2


4-479
OMe
n-Pr
NO2


4-480
OMe
i-Pr
NO2


4-481
OEt
Me
NO2


4-482
OEt
Et
NO2


4-483
OEt
n-Pr
NO2


4-484
OEt
i-Pr
NO2


4-485
NO2
Me
NO2


4-486
NO2
Et
NO2


4-487
NO2
n-Pr
NO2


4-488
NO2
i-Pr
NO2


4-489
SO2Me
Me
NO2


4-490
SO2Me
Et
NO2


4-491
SO2Me
n-Pr
NO2


4-492
SO2Me
i-Pr
NO2


4-493
CH2OMe
Me
NO2


4-494
CH2OMe
Et
NO2


4-495
CH2OMe
n-Pr
NO2


4-496
CH2OMe
i-Pr
NO2


4-497
CH2SO2Me
Me
NO2


4-498
CH2SO2Me
Et
NO2


4-499
CH2SO2Me
n-Pr
NO2


4-500
CH2SO2Me
i-Pr
NO2


4-501
CH2OCH2CH2OMe
Me
NO2


4-502
CH2OCH2CH2OMe
Et
NO2


4-503
CH2OCH2CH2OMe
n-Pr
NO2


4-504
CH2OCH2CH2OMe
i-Pr
NO2


4-505
CH2OCH2CH2OEt
Me
NO2


4-506
CH2OCH2CH2OEt
Et
NO2


4-507
CH2OCH2CH2OEt
n-Pr
NO2


4-508
CH2OCH2CH2OEt
i-Pr
NO2


4-509
CH2OCH2CH2CH2OMe
Me
NO2


4-510
CH2OCH2CH2CH2OMe
Et
NO2


4-511
CH2OCH2CH2CH2OMe
n-Pr
NO2


4-512
CH2OCH2CH2CH2OMe
i-Pr
NO2


4-513
CH2OCH2OMe
Me
NO2


4-514
CH2OCH2OMe
Et
NO2


4-515
CH2OCH2OMe
n-Pr
NO2


4-516
CH2OCH2OMe
i-Pr
NO2


4-517
CH2OCH2OEt
Me
NO2


4-518
CH2OCH2OEt
Et
NO2


4-519
CH2OCH2OEt
n-Pr
NO2


4-520
CH2OCH2OEt
i-Pr
NO2


4-521
CH2OCH2CH2SO2Me
Me
NO2


4-522
CH2OCH2CH2SO2Me
Et
NO2


4-523
CH2OCH2CH2SO2Me
n-Pr
NO2


4-524
CH2OCH2CH2SO2Me
i-Pr
NO2


4-525
CH2SO2CH2CH2OMe
Me
NO2


4-526
CH2SO2CH2CH2OMe
Et
NO2


4-527
CH2SO2CH2CH2OMe
n-Pr
NO2


4-528
CH2SO2CH2CH2OMe
i-Pr
NO2


4-529
CH2SO2CH2CH2SO2Me
Me
NO2


4-530
CH2SO2CH2CH2SO2Me
Et
NO2


4-531
CH2SO2CH2CH2SO2Me
n-Pr
NO2


4-532
CH2SO2CH2CH2SO2Me
i-Pr
NO2
















TABLE 5







Compounds of the formula (I) according to the invention in which R1 is


methyl and R2 is hydrogen.








 

















Physical data:


No.
X
R3
Y
R4
1H-NMR: δ [CDCl3]





5-1 
Cl
Me
SO2Me
—SO2-n-Pr



5-2 
Cl
Et
SO2Me
—SO2-n-Pr


5-3 
Me
Me
SO2Me
—SO2-n-Pr


5-4 
Me
Et
SO2Me
—SO2-n-Pr


5-5 
CF3
Me
SO2Me
—SO2-n-Pr


5-6 
CF3
Et
SO2Me
—SO2-n-Pr


5-7 
OMe
Me
SO2Me
—SO2-n-Pr


5-8 
OMe
Et
SO2Me
—SO2-n-Pr


5-9 
NO2
Me
SO2Me
—SO2-n-Pr


5-10 
NO2
Et
SO2Me
—SO2-n-Pr


5-11 
SO2Me
Me
SO2Me
—SO2-n-Pr


5-12 
SO2Me
Et
SO2Me
—SO2-n-Pr


5-13 
CH2OMe
Me
SO2Me
—SO2-n-Pr


5-14 
CH2OMe
Et
SO2Me
—SO2-n-Pr


5-15 
CH2SO2Me
Me
SO2Me
—SO2-n-Pr


5-16 
CH2SO2Me
Et
SO2Me
—SO2-n-Pr


5-17 
CH2OCH2CH2OMe
Me
SO2Me
—SO2-n-Pr


5-18 
CH2OCH2CH2OMe
Et
SO2Me
—SO2-n-Pr


5-19 
Cl
Me
Cl
—SO2-n-Pr


5-20 
Cl
Et
Cl
—SO2-n-Pr


5-21 
Me
Me
Cl
—SO2-n-Pr


5-22 
Me
Et
Cl
—SO2-n-Pr


5-23 
CF3
Me
Cl
—SO2-n-Pr


5-24 
CF3
Et
Cl
—SO2-n-Pr


5-25 
OMe
Me
Cl
—SO2-n-Pr


5-26 
OMe
Et
Cl
—SO2-n-Pr


5-27 
NO2
Me
Cl
—SO2-n-Pr


5-28 
NO2
Et
Cl
—SO2-n-Pr


5-29 
SO2Me
Me
Cl
—SO2-n-Pr


5-30 
SO2Me
Et
Cl
—SO2-n-Pr


5-31 
CH2OMe
Me
Cl
—SO2-n-Pr


5-32 
CH2OMe
Et
Cl
—SO2-n-Pr


5-33 
CH2SO2Me
Me
Cl
—SO2-n-Pr


5-34 
CH2SO2Me
Et
Cl
—SO2-n-Pr


5-35 
CH2OCH2CH2OMe
Me
Cl
—SO2-n-Pr


5-36 
CH2OCH2CH2OMe
Et
Cl
—SO2-n-Pr


5-37 
Cl
Me
Br
—SO2-n-Pr


5-38 
Cl
Et
Br
—SO2-n-Pr


5-39 
Me
Me
Br
—SO2-n-Pr


5-40 
Me
Et
Br
—SO2-n-Pr


5-41 
CF3
Me
Br
—SO2-n-Pr


5-42 
CF3
Et
Br
—SO2-n-Pr


5-43 
OMe
Me
Br
—SO2-n-Pr


5-44 
OMe
Et
Br
—SO2-n-Pr


5-45 
NO2
Me
Br
—SO2-n-Pr


5-46 
NO2
Et
Br
—SO2-n-Pr


5-47 
SO2Me
Me
Br
—SO2-n-Pr


5-48 
SO2Me
Et
Br
—SO2-n-Pr


5-49 
CH2OMe
Me
Br
—SO2-n-Pr


5-50 
CH2OMe
Et
Br
—SO2-n-Pr


5-51 
CH2SO2Me
Me
Br
—SO2-n-Pr


5-52 
CH2SO2Me
Et
Br
—SO2-n-Pr


5-53 
CH2OCH2CH2OMe
Me
Br
—SO2-n-Pr


5-54 
CH2OCH2CH2OMe
Et
Br
—SO2-n-Pr


5-55 
Cl
Me
I
—SO2-n-Pr


5-56 
Cl
Et
I
—SO2-n-Pr


5-57 
Me
Me
I
—SO2-n-Pr


5-58 
Me
Et
I
—SO2-n-Pr


5-59 
CF3
Me
I
—SO2-n-Pr


5-60 
CF3
Et
I
—SO2-n-Pr


5-61 
OMe
Me
I
—SO2-n-Pr


5-62 
OMe
Et
I
—SO2-n-Pr


5-63 
NO2
Me
I
—SO2-n-Pr


5-64 
NO2
Et
I
—SO2-n-Pr


5-65 
SO2Me
Me
I
—SO2-n-Pr


5-66 
SO2Me
Et
I
—SO2-n-Pr


5-67 
CH2OMe
Me
I
—SO2-n-Pr


5-68 
CH2OMe
Et
I
—SO2-n-Pr


5-69 
CH2SO2Me
Me
I
—SO2-n-Pr


5-70 
CH2SO2Me
Et
I
—SO2-n-Pr


5-71 
CH2OCH2CH2OMe
Me
I
—SO2-n-Pr


5-72 
CH2OCH2CH2OMe
Et
I
—SO2-n-Pr


5-73 
Cl
Me
NO2
—SO2-n-Pr


5-74 
Cl
Et
NO2
—SO2-n-Pr


5-75 
Me
Me
NO2
—SO2-n-Pr


5-76 
Me
Et
NO2
—SO2-n-Pr


5-77 
CF3
Me
NO2
—SO2-n-Pr


5-78 
CF3
Et
NO2
—SO2-n-Pr


5-79 
OMe
Me
NO2
—SO2-n-Pr


5-80 
OMe
Et
NO2
—SO2-n-Pr


5-81 
NO2
Me
NO2
—SO2-n-Pr


5-82 
NO2
Et
NO2
—SO2-n-Pr


5-83 
SO2Me
Me
NO2
—SO2-n-Pr


5-84 
SO2Me
Et
NO2
—SO2-n-Pr


5-85 
CH2OMe
Me
NO2
—SO2-n-Pr


5-86 
CH2OMe
Et
NO2
—SO2-n-Pr


5-87 
CH2SO2Me
Me
NO2
—SO2-n-Pr


5-88 
CH2SO2Me
Et
NO2
—SO2-n-Pr


5-89 
CH2OCH2CH2OMe
Me
NO2
—SO2-n-Pr


5-90 
CH2OCH2CH2OMe
Et
NO2
—SO2-n-Pr


5-91 
Cl
Me
SO2Me
—CO-Ph


5-92 
Cl
Et
SO2Me
—CO-Ph


5-93 
Me
Me
SO2Me
—CO-Ph


5-94 
Me
Et
SO2Me
—CO-Ph


5-95 
CF3
Me
SO2Me
—CO-Ph


5-96 
CF3
Et
SO2Me
—CO-Ph


5-97 
OMe
Me
SO2Me
—CO-Ph


5-98 
OMe
Et
SO2Me
—CO-Ph


5-99 
NO2
Me
SO2Me
—CO-Ph


5-100
NO2
Et
SO2Me
—CO-Ph


5-101
SO2Me
Me
SO2Me
—CO-Ph


5-102
SO2Me
Et
SO2Me
—CO-Ph


5-103
CH2OMe
Me
SO2Me
—CO-Ph


5-104
CH2OMe
Et
SO2Me
—CO-Ph


5-105
CH2SO2Me
Me
SO2Me
—CO-Ph


5-106
CH2SO2Me
Et
SO2Me
—CO-Ph


5-107
CH2OCH2CH2OMe
Me
SO2Me
—CO-Ph


5-108
CH2OCH2CH2OMe
Et
SO2Me
—CO-Ph


5-109
Cl
Me
Cl
—CO-Ph


5-110
Cl
Et
Cl
—CO-Ph


5-111
Me
Me
Cl
—CO-Ph


5-112
Me
Et
Cl
—CO-Ph


5-113
CF3
Me
Cl
—CO-Ph


5-114
CF3
Et
Cl
—CO-Ph


5-115
OMe
Me
Cl
—CO-Ph


5-116
OMe
Et
Cl
—CO-Ph


5-117
NO2
Me
Cl
—CO-Ph


5-118
NO2
Et
Cl
—CO-Ph


5-119
SO2Me
Me
Cl
—CO-Ph


5-120
SO2Me
Et
Cl
—CO-Ph


5-121
CH2OMe
Me
Cl
—CO-Ph


5-122
CH2OMe
Et
Cl
—CO-Ph


5-123
CH2SO2Me
Me
Cl
—CO-Ph


5-124
CH2SO2Me
Et
Cl
—CO-Ph


5-125
CH2OCH2CH2OMe
Me
Cl
—CO-Ph


5-126
CH2OCH2CH2OMe
Et
Cl
—CO-Ph


5-127
Cl
Me
Br
—CO-Ph


5-128
Cl
Et
Br
—CO-Ph


5-129
Me
Me
Br
—CO-Ph


5-130
Me
Et
Br
—CO-Ph


5-131
CF3
Me
Br
—CO-Ph


5-132
CF3
Et
Br
—CO-Ph


5-133
OMe
Me
Br
—CO-Ph


5-134
OMe
Et
Br
—CO-Ph


5-135
NO2
Me
Br
—CO-Ph


5-136
NO2
Et
Br
—CO-Ph


5-137
SO2Me
Me
Br
—CO-Ph


5-138
SO2Me
Et
Br
—CO-Ph


5-139
CH2OMe
Me
Br
—CO-Ph


5-140
CH2OMe
Et
Br
—CO-Ph


5-141
CH2SO2Me
Me
Br
—CO-Ph


5-142
CH2SO2Me
Et
Br
—CO-Ph


5-143
CH2OCH2CH2OMe
Me
Br
—CO-Ph


5-144
CH2OCH2CH2OMe
Et
Br
—CO-Ph


5-145
Cl
Me
Cl
—CO-Ph


5-146
Cl
Et
Cl
—CO-Ph


5-147
Me
Me
Cl
—CO-Ph


5-148
Me
Et
Cl
—CO-Ph


5-149
CF3
Me
Cl
—CO-Ph


5-150
CF3
Et
Cl
—CO-Ph


5-151
OMe
Me
Cl
—CO-Ph


5-152
OMe
Et
Cl
—CO-Ph


5-153
NO2
Me
Cl
—CO-Ph


5-154
NO2
Et
Cl
—CO-Ph


5-155
SO2Me
Me
Cl
—CO-Ph


5-156
SO2Me
Et
Cl
—CO-Ph


5-157
CH2OMe
Me
Cl
—CO-Ph


5-158
CH2OMe
Et
Cl
—CO-Ph


5-159
CH2SO2Me
Me
Cl
—CO-Ph


5-160
CH2SO2Me
Et
Cl
—CO-Ph


5-161
CH2OCH2CH2OMe
Me
Cl
—CO-Ph


5-162
CH2OCH2CH2OMe
Et
Cl
—CO-Ph


5-163
Cl
Me
NO2
—CO-Ph


5-164
Cl
Et
NO2
—CO-Ph


5-165
Me
Me
NO2
—CO-Ph


5-166
Me
Et
NO2
—CO-Ph


5-167
CF3
Me
NO2
—CO-Ph


5-168
CF3
Et
NO2
—CO-Ph


5-169
OMe
Me
NO2
—CO-Ph


5-170
OMe
Et
NO2
—CO-Ph


5-171
NO2
Me
NO2
—CO-Ph


5-172
NO2
Et
NO2
—CO-Ph


5-173
SO2Me
Me
NO2
—CO-Ph


5-174
SO2Me
Et
NO2
—CO-Ph


5-175
CH2OMe
Me
NO2
—CO-Ph


5-176
CH2OMe
Et
NO2
—CO-Ph


5-177
CH2SO2Me
Me
NO2
—CO-Ph


5-178
CH2SO2Me
Et
NO2
—CO-Ph


5-179
CH2OCH2CH2OMe
Me
NO2
—CO-Ph


5-180
CH2OCH2CH2OMe
Et
NO2
—CO-Ph


5-181
Cl
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-182
Cl
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-183
Me
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-184
Me
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-185
CF3
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-186
CF3
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-187
OMe
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-188
OMe
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-189
NO2
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-190
NO2
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-191
SO2Me
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-192
SO2Me
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-193
CH2OMe
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-194
CH2OMe
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-195
CH2SO2Me
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-196
CH2SO2Me
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-197
CH2OCH2CH2OMe
Me
SO2Me
—CH2—CO—






(4-Me-Ph)


5-198
CH2OCH2CH2OMe
Et
SO2Me
—CH2—CO—






(4-Me-Ph)


5-199
Cl
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-200
Cl
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-201
Me
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-202
Me
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-203
CF3
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-204
CF3
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-205
OMe
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-206
OMe
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-207
NO2
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-208
NO2
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-209
SO2Me
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-210
SO2Me
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-211
CH2OMe
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-212
CH2OMe
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-213
CH2SO2Me
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-214
CH2SO2Me
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-215
CH2OCH2CH2OMe
Me
Cl
—CH2—CO—






(4-Me-Ph)


5-216
CH2OCH2CH2OMe
Et
Cl
—CH2—CO—






(4-Me-Ph)


5-217
Cl
Me
Br
—CH2—CO—






(4-Me-Ph)


5-218
Cl
Et
Br
—CH2—CO—






(4-Me-Ph)


5-219
Me
Me
Br
—CH2—CO—






(4-Me-Ph)


5-220
Me
Et
Br
—CH2—CO—






(4-Me-Ph)


5-221
CF3
Me
Br
—CH2—CO—






(4-Me-Ph)


5-222
CF3
Et
Br
—CH2—CO—






(4-Me-Ph)


5-223
OMe
Me
Br
—CH2—CO—






(4-Me-Ph)


5-224
OMe
Et
Br
—CH2—CO—






(4-Me-Ph)


5-225
NO2
Me
Br
—CH2—CO—






(4-Me-Ph)


5-226
NO2
Et
Br
—CH2—CO—






(4-Me-Ph)


5-227
SO2Me
Me
Br
—CH2—CO—






(4-Me-Ph)


5-228
SO2Me
Et
Br
—CH2—CO—






(4-Me-Ph)


5-229
CH2OMe
Me
Br
—CH2—CO—






(4-Me-Ph)


5-230
CH2OMe
Et
Br
—CH2—CO—






(4-Me-Ph)


5-231
CH2SO2Me
Me
Br
—CH2—CO—






(4-Me-Ph)


5-232
CH2SO2Me
Et
Br
—CH2—CO—






(4-Me-Ph)


5-233
CH2OCH2OMe
Me
Br
—CH2—CO—






(4-Me-Ph)


5-234
CH2OCH2OMe
Et
Br
—CH2—CO—






(4-Me-Ph)


5-235
Cl
Me
I
—CH2—CO—






(4-Me-Ph)


5-236
Cl
Et
I
—CH2—CO—






(4-Me-Ph)


5-237
Me
Me
I
—CH2—CO—






(4-Me-Ph)


5-238
Me
Et
I
—CH2—CO—






(4-Me-Ph)


5-239
CF3
Me
I
—CH2—CO—






(4-Me-Ph)


5-240
CF3
Et
I
—CH2—CO—






(4-Me-Ph)


5-241
OMe
Me
I
—CH2—CO—






(4-Me-Ph)


5-242
OMe
Et
I
—CH2—CO—






(4-Me-Ph)


5-243
NO2
Me
I
—CH2—CO—






(4-Me-Ph)


5-244
NO2
Et
I
—CH2—CO—






(4-Me-Ph)


5-245
SO2Me
Me
I
—CH2—CO—






(4-Me-Ph)


5-246
SO2Me
Et
I
—CH2—CO—






(4-Me-Ph)


5-247
CH2OMe
Me
I
—CH2—CO—






(4-Me-Ph)


5-248
CH2OMe
Et
I
—CH2—CO—






(4-Me-Ph)


5-249
CH2SO2Me
Me
I
—CH2—CO—






(4-Me-Ph)


5-250
CH2SO2Me
Et
I
—CH2—CO—






(4-Me-Ph)


5-251
CH2OCH2OMe
Me
I
—CH2—CO—






(4-Me-Ph)


5-252
CH2OCH2OMe
Et
I
—CH2—CO—






(4-Me-Ph)


5-253
Cl
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-254
Cl
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-255
Me
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-256
Me
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-257
CF3
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-258
CF3
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-259
OMe
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-260
OMe
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-261
NO2
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-262
NO2
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-263
SO2Me
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-264
SO2Me
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-265
CH2OMe
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-266
CH2OMe
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-267
CH2SO2Me
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-268
CH2SO2Me
Et
NO2
—CH2—CO—






(4-Me-Ph)


5-269
CH2OCH2CH2OMe
Me
NO2
—CH2—CO—






(4-Me-Ph)


5-270
CH2OCH2CH2OMe
Et
NO2
—CH2—CO—






(4-Me-Ph)
















TABLE 6







Compounds of the formula (I) according to the invention


in which R1 is ethyl and R2 is hydrogen.








 

















Physical







data:







1H-NMR:


No.
X
R3
Y
R4
δ [CDCl3]





6-1
Cl
Me
SO2Me
—SO2-n-Pr



6-2
Cl
Et
SO2Me
—SO2-n-Pr


6-3
Me
Me
SO2Me
—SO2-n-Pr


6-4
Me
Et
SO2Me
—SO2-n-Pr


6-5
CF3
Me
SO2Me
—SO2-n-Pr


6-6
CF3
Et
SO2Me
—SO2-n-Pr


6-7
OMe
Me
SO2Me
—SO2-n-Pr


6-8
OMe
Et
SO2Me
—SO2-n-Pr


6-9
NO2
Me
SO2Me
—SO2-n-Pr


6-10
NO2
Et
SO2Me
—SO2-n-Pr


6-11
SO2Me
Me
SO2Me
—SO2-n-Pr


6-12
SO2Me
Et
SO2Me
—SO2-n-Pr


6-13
CH2OMe
Me
SO2Me
—SO2-n-Pr


6-14
CH2OMe
Et
SO2Me
—SO2-n-Pr


6-15
CH2SO2Me
Me
SO2Me
—SO2-n-Pr


6-16
CH2SO2Me
Et
SO2Me
—SO2-n-Pr


6-17
CH2OCH2CH2OMe
Me
SO2Me
—SO2-n-Pr


6-18
CH2OCH2CH2OMe
Et
SO2Me
—SO2-n-Pr


6-19
Cl
Me
Cl
—SO2-n-Pr


6-20
Cl
Et
Cl
—SO2-n-Pr


6-21
Me
Me
Cl
—SO2-n-Pr


6-22
Me
Et
Cl
—SO2-n-Pr


6-23
CF3
Me
Cl
—SO2-n-Pr


6-24
CF3
Et
Cl
—SO2-n-Pr


6-25
OMe
Me
Cl
—SO2-n-Pr


6-26
OMe
Et
Cl
—SO2-n-Pr


6-27
NO2
Me
Cl
—SO2-n-Pr


6-28
NO2
Et
Cl
—SO2-n-Pr


6-29
SO2Me
Me
Cl
—SO2-n-Pr


6-30
SO2Me
Et
Cl
—SO2-n-Pr


6-31
CH2OMe
Me
Cl
—SO2-n-Pr


6-32
CH2OMe
Et
Cl
—SO2-n-Pr


6-33
CH2SO2Me
Me
Cl
—SO2-n-Pr


6-34
CH2SO2Me
Et
Cl
—SO2-n-Pr


6-35
CH2OCH2CH2OMe
Me
Cl
—SO2-n-Pr


6-36
CH2OCH2CH2OMe
Et
Cl
—SO2-n-Pr


6-37
Cl
Me
Br
—SO2-n-Pr


6-38
Cl
Et
Br
—SO2-n-Pr


6-39
Me
Me
Br
—SO2-n-Pr


6-40
Me
Et
Br
—SO2-n-Pr


6-41
CF3
Me
Br
—SO2-n-Pr


6-42
CF3
Et
Br
—SO2-n-Pr


6-43
OMe
Me
Br
—SO2-n-Pr


6-44
OMe
Et
Br
—SO2-n-Pr


6-45
NO2
Me
Br
—SO2-n-Pr


6-46
NO2
Et
Br
—SO2-n-Pr


6-47
SO2Me
Me
Br
—SO2-n-Pr


6-48
SO2Me
Et
Br
—SO2-n-Pr


6-49
CH2OMe
Me
Br
—SO2-n-Pr


6-50
CH2OMe
Et
Br
—SO2-n-Pr


6-51
CH2SO2Me
Me
Br
—SO2-n-Pr


6-52
CH2SO2Me
Et
Br
—SO2-n-Pr


6-53
CH2OCH2CH2OMe
Me
Br
—SO2-n-Pr


6-54
CH2OCH2CH2OMe
Et
Br
—SO2-n-Pr


6-55
Cl
Me
I
—SO2-n-Pr


6-56
Cl
Et
I
—SO2-n-Pr


6-57
Me
Me
I
—SO2-n-Pr


6-58
Me
Et
I
—SO2-n-Pr


6-59
CF3
Me
I
—SO2-n-Pr


6-60
CF3
Et
I
—SO2-n-Pr


6-61
OMe
Me
I
—SO2-n-Pr


6-62
OMe
Et
I
—SO2-n-Pr


6-63
NO2
Me
I
—SO2-n-Pr


6-64
NO2
Et
I
—SO2-n-Pr


6-65
SO2Me
Me
I
—SO2-n-Pr


6-66
SO2Me
Et
I
—SO2-n-Pr


6-67
CH2OMe
Me
I
—SO2-n-Pr


6-68
CH2OMe
Et
I
—SO2-n-Pr


6-69
CH2SO2Me
Me
I
—SO2-n-Pr


6-70
CH2SO2Me
Et
I
—SO2-n-Pr


6-71
CH2OCH2CH2OMe
Me
I
—SO2-n-Pr


6-72
CH2OCH2CH2OMe
Et
I
—SO2-n-Pr


6-73
Cl
Me
NO2
—SO2-n-Pr


6-74
Cl
Et
NO2
—SO2-n-Pr


6-75
Me
Me
NO2
—SO2-n-Pr


6-76
Me
Et
NO2
—SO2-n-Pr


6-77
CF3
Me
NO2
—SO2-n-Pr


6-78
CF3
Et
NO2
—SO2-n-Pr


6-79
OMe
Me
NO2
—SO2-n-Pr


6-80
OMe
Et
NO2
—SO2-n-Pr


6-81
NO2
Me
NO2
—SO2-n-Pr


6-82
NO2
Et
NO2
—SO2-n-Pr


6-83
SO2Me
Me
NO2
—SO2-n-Pr


6-84
SO2Me
Et
NO2
—SO2-n-Pr


6-85
CH2OMe
Me
NO2
—SO2-n-Pr


6-86
CH2OMe
Et
NO2
—SO2-n-Pr


6-87
CH2SO2Me
Me
NO2
—SO2-n-Pr


6-88
CH2SO2Me
Et
NO2
—SO2-n-Pr


6-89
CH2OCH2CH2OMe
Me
NO2
—SO2-n-Pr


6-90
CH2OCH2CH2OMe
Et
NO2
—SO2-n-Pr


6-91
Cl
Me
SO2Me
—CO-Ph


6-92
Cl
Et
SO2Me
—CO-Ph


6-93
Me
Me
SO2Me
—CO-Ph


6-94
Me
Et
SO2Me
—CO-Ph


6-95
CF3
Me
SO2Me
—CO-Ph


6-96
CF3
Et
SO2Me
—CO-Ph


6-97
OMe
Me
SO2Me
—CO-Ph


6-98
OMe
Et
SO2Me
—CO-Ph


6-99
NO2
Me
SO2Me
—CO-Ph


6-100
NO2
Et
SO2Me
—CO-Ph


6-101
SO2Me
Me
SO2Me
—CO-Ph


6-102
SO2Me
Et
SO2Me
—CO-Ph


6-103
CH2OMe
Me
SO2Me
—CO-Ph


6-104
CH2OMe
Et
SO2Me
—CO-Ph


6-105
CH2SO2Me
Me
SO2Me
—CO-Ph


6-106
CH2SO2Me
Et
SO2Me
—CO-Ph


6-107
CH2OCH2CH2OMe
Me
SO2Me
—CO-Ph


6-108
CH2OCH2CH2OMe
Et
SO2Me
—CO-Ph


6-109
Cl
Me
Cl
—CO-Ph


6-110
Cl
Et
Cl
—CO-Ph


6-111
Me
Me
Cl
—CO-Ph


6-112
Me
Et
Cl
—CO-Ph


6-113
CF3
Me
Cl
—CO-Ph


6-114
CF3
Et
Cl
—CO-Ph


6-115
OMe
Me
Cl
—CO-Ph


6-116
OMe
Et
Cl
—CO-Ph


6-117
NO2
Me
Cl
—CO-Ph


6-118
NO2
Et
Cl
—CO-Ph


6-119
SO2Me
Me
Cl
—CO-Ph


6-120
SO2Me
Et
Cl
—CO-Ph


6-121
CH2OMe
Me
Cl
—CO-Ph


6-122
CH2OMe
Et
Cl
—CO-Ph


6-123
CH2SO2Me
Me
Cl
—CO-Ph


6-124
CH2SO2Me
Et
Cl
—CO-Ph


6-125
CH2OCH2CH2OMe
Me
Cl
—CO-Ph


6-126
CH2OCH2CH2OMe
Et
Cl
—CO-Ph


6-127
Cl
Me
Br
—CO-Ph


6-128
Cl
Et
Br
—CO-Ph


6-129
Me
Me
Br
—CO-Ph


6-130
Me
Et
Br
—CO-Ph


6-131
CF3
Me
Br
—CO-Ph


6-132
CF3
Et
Br
—CO-Ph


6-133
OMe
Me
Br
—CO-Ph


6-134
OMe
Et
Br
—CO-Ph


6-135
NO2
Me
Br
—CO-Ph


6-136
NO2
Et
Br
—CO-Ph


6-137
SO2Me
Me
Br
—CO-Ph


6-138
SO2Me
Et
Br
—CO-Ph


6-139
CH2OMe
Me
Br
—CO-Ph


6-140
CH2OMe
Et
Br
—CO-Ph


6-141
CH2SO2Me
Me
Br
—CO-Ph


6-142
CH2SO2Me
Et
Br
—CO-Ph


6-143
CH2OCH2CH2OMe
Me
Br
—CO-Ph


6-144
CH2OCH2CH2OMe
Et
Br
—CO-Ph


6-145
Cl
Me
I
—CO-Ph


6-146
Cl
Et
I
—CO-Ph


6-147
Me
Me
I
—CO-Ph


6-148
Me
Et
I
—CO-Ph


6-149
CF3
Me
I
—CO-Ph


6-150
CF3
Et
I
—CO-Ph


6-151
OMe
Me
I
—CO-Ph


6-152
OMe
Et
I
—CO-Ph


6-153
NO2
Me
I
—CO-Ph


6-154
NO2
Et
I
—CO-Ph


6-155
SO2Me
Me
I
—CO-Ph


6-156
SO2Me
Et
I
—CO-Ph


6-157
CH2OMe
Me
I
—CO-Ph


6-158
CH2OMe
Et
I
—CO-Ph


6-159
CH2SO2Me
Me
I
—CO-Ph


6-160
CH2SO2Me
Et
I
—CO-Ph


6-161
CH2OCH2CH2OMe
Me
I
—CO-Ph


6-162
CH2OCH2CH2OMe
Et
I
—CO-Ph


6-163
Cl
Me
NO2
—CO-Ph


6-164
Cl
Et
NO2
—CO-Ph


6-165
Me
Me
NO2
—CO-Ph


6-166
Me
Et
NO2
—CO-Ph


6-167
CF3
Me
NO2
—CO-Ph


6-168
CF3
Et
NO2
—CO-Ph


6-169
OMe
Me
NO2
—CO-Ph


6-170
OMe
Et
NO2
—CO-Ph


6-171
NO2
Me
NO2
—CO-Ph


6-172
NO2
Et
NO2
—CO-Ph


6-173
SO2Me
Me
NO2
—CO-Ph


6-174
SO2Me
Et
NO2
—CO-Ph


6-175
CH2OMe
Me
NO2
—CO-Ph


6-176
CH2OMe
Et
NO2
—CO-Ph


6-177
CH2SO2Me
Me
NO2
—CO-Ph


6-178
CH2SO2Me
Et
NO2
—CO-Ph


6-179
CH2OCH2CH2OMe
Me
NO2
—CO-Ph


6-180
CH2OCH2CH2OMe
Et
NO2
—CO-Ph


6-181
Cl
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


6-182
Cl
Et
SO2Me
CH2—CO-






(4-Me-Ph)


6-183
Me
Me
SO2Me
CH2—CO-






(4-Me-Ph)


6-184
Me
Et
SO2Me
CH2—CO-






(4-Me-Ph)


6-185
CF3
Me
SO2Me
CH2—CO-






(4-Me-Ph)


6-186
CF3
Et
SO2Me
CH2—CO-






(4-Me-Ph)


6-187
OMe
Me
SO2Me
CH2—CO-






(4-Me-Ph)


6-188
OMe
Et
SO2Me
CH2—CO-






(4-Me-Ph)


6-189
NO2
Me
SO2Me
CH2—CO-






(4-Me-Ph)


6-190
NO2
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


6-191
SO2Me
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


6-192
SO2Me
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


6-193
CH2OMe
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


6-194
CH2OMe
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


6-195
CH2SO2Me
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


6-196
CH2SO2Me
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


6-197
CH2OCH2CH2OMe
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


6-198
CH2OCH2CH2OMe
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


6-199
Cl
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-200
Cl
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-201
Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-202
Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-203
CF3
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-204
CF3
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-205
OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-206
OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-207
NO2
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-208
NO2
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-209
SO2Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-210
SO2Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-211
CH2OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-212
CH2OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-213
CH2SO2Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-214
CH2SO2Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-215
CH2OCH2CH2OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


6-216
CH2OCH2CH2OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


6-217
Cl
Me
Br
—CH2—CO-






(4-Me-Ph)


6-218
Cl
Et
Br
—CH2—CO-






(4-Me-Ph)


6-219
Me
Me
Br
—CH2—CO-






(4-Me-Ph)


6-220
Me
Et
Br
—CH2—CO-






(4-Me-Ph)


6-221
CF3
Me
Br
—CH2—CO-






(4-Me-Ph)


6-222
CF3
Et
Br
—CH2—CO-






(4-Me-Ph)


6-223
OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


6-224
OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


6-225
NO2
Me
Br
—CH2—CO-






(4-Me-Ph)


6-226
NO2
Et
Br
—CH2—CO-






(4-Me-Ph)


6-227
SO2Me
Me
Br
—CH2—CO-






(4-Me-Ph)


6-228
SO2Me
Et
Br
—CH2—CO-






(4-Me-Ph)


6-229
CH2OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


6-230
CH2OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


6-231
CH2SO2Me
Me
Br
—CH2—CO-






(4-Me-Ph)


6-232
CH2SO2Me
Et
Br
—CH2—CO-






(4-Me-Ph)


6-233
CH2OCH2CH2OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


6-234
CH2OCH2CH2OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


6-235
Cl
Me
I
—CH2—CO-






(4-Me-Ph)


6-236
Cl
Et
I
—CH2—CO-






(4-Me-Ph)


6-237
Me
Me
I
—CH2—CO-






(4-Me-Ph)


6-238
Me
Et
I
—CH2—CO-






(4-Me-Ph)


6-239
CF3
Me
I
—CH2—CO-






(4-Me-Ph)


6-240
CF3
Et
I
—CH2—CO-






(4-Me-Ph)


6-241
OMe
Me
I
—CH2—CO-






(4-Me-Ph)


6-242
OMe
Et
I
—CH2—CO-






(4-Me-Ph)


6-243
NO2
Me
I
—CH2—CO-






(4-Me-Ph)


6-244
NO2
Et
I
—CH2—CO-






(4-Me-Ph)


6-245
SO2Me
Me
I
—CH2—CO-






(4-Me-Ph)


6-246
SO2Me
Et
I
—CH2—CO-






(4-Me-Ph)


6-247
CH2OMe
Me
I
—CH2—CO-






(4-Me-Ph)


6-248
CH2OMe
Et
I
—CH2—CO-






(4-Me-Ph)


6-249
CH2SO2Me
Me
I
—CH2—CO-






(4-Me-Ph)


6-250
CH2SO2Me
Et
I
—CH2—CO-






(4-Me-Ph)


6-251
CH2OCH2CH2OMe
Me
I
—CH2—CO-






(4-Me-Ph)


6-252
CH2OCH2CH2OMe
Et
I
—CH2—CO-






(4-Me-Ph)


6-253
Cl
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-254
Cl
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-255
Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-256
Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-257
CF3
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-258
CF3
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-259
OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-260
OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-261
NO2
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-262
NO2
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-263
SO2Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-264
SO2Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-265
CH2OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-266
CH2OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-267
CH2SO2Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-268
CH2SO2Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


6-269
CH2OCH2CH2OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


6-270
CH2OCH2CH2OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)
















TABLE 7







Compounds of the formula (I) according to the invention


in which R1 and R2 are each methyl.








 

















Physical







data:







1H-NMR:


No.
X
R3
Y
R4
δ [CDCl3]





7-1
Cl
Me
SO2Me
—SO2-n-Pr



7-2
Cl
Et
SO2Me
—SO2-n-Pr


7-3
Me
Me
SO2Me
—SO2-n-Pr


7-4
Me
Et
SO2Me
—SO2-n-Pr


7-5
CF3
Me
SO2Me
—SO2-n-Pr


7-6
CF3
Et
SO2Me
—SO2-n-Pr


7-7
OMe
Me
SO2Me
—SO2-n-Pr


7-8
OMe
Et
SO2Me
—SO2-n-Pr


7-9
NO2
Me
SO2Me
—SO2-n-Pr


7-10
NO2
Et
SO2Me
—SO2-n-Pr


7-11
SO2Me
Me
SO2Me
—SO2-n-Pr


7-12
SO2Me
Et
SO2Me
—SO2-n-Pr


7-13
CH2OMe
Me
SO2Me
—SO2-n-Pr


7-14
CH2OMe
Et
SO2Me
—SO2-n-Pr


7-15
CH2SO2Me
Me
SO2Me
—SO2-n-Pr


7-16
CH2SO2Me
Et
SO2Me
—SO2-n-Pr


7-17
CH2OCH2CH2OMe
Me
SO2Me
—SO2-n-Pr


7-18
CH2OCH2CH2OMe
Et
SO2Me
—SO2-n-Pr


7-19
Cl
Me
Cl
—SO2-n-Pr


7-20
Cl
Et
Cl
—SO2-n-Pr


7-21
Me
Me
Cl
—SO2-n-Pr


7-22
Me
Et
Cl
—SO2-n-Pr


7-23
CF3
Me
Cl
—SO2-n-Pr


7-24
CF3
Et
Cl
—SO2-n-Pr


7-25
OMe
Me
Cl
—SO2-n-Pr


7-26
OMe
Et
Cl
—SO2-n-Pr


7-27
NO2
Me
Cl
—SO2-n-Pr


7-28
NO2
Et
Cl
—SO2-n-Pr


7-29
SO2Me
Me
Cl
—SO2-n-Pr


7-30
SO2Me
Et
Cl
—SO2-n-Pr


7-31
CH2OMe
Me
Cl
—SO2-n-Pr


7-32
CH2OMe
Et
Cl
—SO2-n-Pr


7-33
CH2SO2Me
Me
Cl
—SO2-n-Pr


7-34
CH2SO2Me
Et
Cl
—SO2-n-Pr


7-35
CH2OCH2CH2OMe
Me
Cl
—SO2-n-Pr


7-36
CH2OCH2CH2OMe
Et
Cl
—SO2-n-Pr


7-37
Cl
Me
Br
—SO2-n-Pr


7-38
Cl
Et
Br
—SO2-n-Pr


7-39
Me
Me
Br
—SO2-n-Pr


7-40
Me
Et
Br
—SO2-n-Pr


7-41
CF3
Me
Br
—SO2-n-Pr


7-42
CF3
Et
Br
—SO2-n-Pr


7-43
OMe
Me
Br
—SO2-n-Pr


7-44
OMe
Et
Br
—SO2-n-Pr


7-45
NO2
Me
Br
—SO2-n-Pr


7-46
NO2
Et
Br
—SO2-n-Pr


7-47
SO2Me
Me
Br
—SO2-n-Pr


7-48
SO2Me
Et
Br
—SO2-n-Pr


7-49
CH2OMe
Me
Br
—SO2-n-Pr


7-50
CH2OMe
Et
Br
—SO2-n-Pr


7-51
CH2SO2Me
Me
Br
—SO2-n-Pr


7-52
CH2SO2Me
Et
Br
—SO2-n-Pr


7-53
CH2OCH2CH2OMe
Me
Br
—SO2-n-Pr


7-54
CH2OCH2CH2OMe
Et
Br
—SO2-n-Pr


7-55
Cl
Me
I
—SO2-n-Pr


7-56
Cl
Et
I
—SO2-n-Pr


7-57
Me
Me
I
—SO2-n-Pr


7-58
Me
Et
I
—SO2-n-Pr


7-59
CF3
Me
I
—SO2-n-Pr


7-60
CF3
Et
I
—SO2-n-Pr


7-61
OMe
Me
I
—SO2-n-Pr


7-62
OMe
Et
I
—SO2-n-Pr


7-63
NO2
Me
I
—SO2-n-Pr


7-64
NO2
Et
I
—SO2-n-Pr


7-65
SO2Me
Me
I
—SO2-n-Pr


7-66
SO2Me
Et
I
—SO2-n-Pr


7-67
CH2OMe
Me
I
—SO2-n-Pr


7-68
CH2OMe
Et
I
—SO2-n-Pr


7-69
CH2SO2Me
Me
I
—SO2-n-Pr


7-70
CH2SO2Me
Et
I
—SO2-n-Pr


7-71
CH2OCH2CH2OMe
Me
I
—SO2-n-Pr


7-72
CH2OCH2CH2OMe
Et
I
—SO2-n-Pr


7-73
Cl
Me
NO2
—SO2-n-Pr


7-74
Cl
Et
NO2
—SO2-n-Pr


7-75
Me
Me
NO2
—SO2-n-Pr


7-76
Me
Et
NO2
—SO2-n-Pr


7-77
CF3
Me
NO2
—SO2-n-Pr


7-78
CF3
Et
NO2
—SO2-n-Pr


7-79
OMe
Me
NO2
—SO2-n-Pr


7-80
OMe
Et
NO2
—SO2-n-Pr


7-81
NO2
Me
NO2
—SO2-n-Pr


7-82
NO2
Et
NO2
—SO2-n-Pr


7-83
SO2Me
Me
NO2
—SO2-n-Pr


7-84
SO2Me
Et
NO2
—SO2-n-Pr


7-85
CH2OMe
Me
NO2
—SO2-n-Pr


7-86
CH2OMe
Et
NO2
—SO2-n-Pr


7-87
CH2SO2Me
Me
NO2
—SO2-n-Pr


7-88
CH2SO2Me
Et
NO2
—SO2-n-Pr


7-89
CH2OCH2CH2OMe
Me
NO2
—SO2-n-Pr


7-90
CH2OCH2CH2OMe
Et
NO2
—SO2-n-Pr


7-91
Cl
Me
SO2Me
—CO-Ph


7-92
Cl
Et
SO2Me
—CO-Ph


7-93
Me
Me
SO2Me
—CO-Ph


7-94
Me
Et
SO2Me
—CO-Ph


7-95
CF3
Me
SO2Me
—CO-Ph


7-96
CF3
Et
SO2Me
—CO-Ph


7-97
OMe
Me
SO2Me
—CO-Ph


7-98
OMe
Et
SO2Me
—CO-Ph


7-99
NO2
Me
SO2Me
—CO-Ph


7-100
NO2
Et
SO2Me
—CO-Ph


7-101
SO2Me
Me
SO2Me
—CO-Ph


7-102
SO2Me
Et
SO2Me
—CO-Ph


7-103
CH2OMe
Me
SO2Me
—CO-Ph


7-104
CH2OMe
Et
SO2Me
—CO-Ph


7-105
CH2SO2Me
Me
SO2Me
—CO-Ph


7-106
CH2SO2Me
Et
SO2Me
—CO-Ph


7-107
CH2OCH2CH2OMe
Me
SO2Me
—CO-Ph


7-108
CH2OCH2CH2OMe
Et
SO2Me
—CO-Ph


7-109
Cl
Me
Cl
—CO-Ph


7-110
Cl
Et
Cl
—CO-Ph


7-111
Me
Me
Cl
—CO-Ph


7-112
Me
Et
Cl
—CO-Ph


7-113
CF3
Me
Cl
—CO-Ph


7-114
CF3
Et
Cl
—CO-Ph


7-115
OMe
Me
Cl
—CO-Ph


7-116
OMe
Et
Cl
—CO-Ph


7-117
NO2
Me
Cl
—CO-Ph


7-118
NO2
Et
Cl
—CO-Ph


7-119
SO2Me
Me
Cl
—CO-Ph


7-120
SO2Me
Et
Cl
—CO-Ph


7-121
CH2OMe
Me
Cl
—CO-Ph


7-122
CH2OMe
Et
Cl
—CO-Ph


7-123
CH2SO2Me
Me
Cl
—CO-Ph


7-124
CH2SO2Me
Et
Cl
—CO-Ph


7-125
CH2OCH2CH2OMe
Me
Cl
—CO-Ph


7-126
CH2OCH2CH2OMe
Et
Cl
—CO-Ph


7-127
Cl
Me
Br
—CO-Ph


7-128
Cl
Et
Br
—CO-Ph


7-129
Me
Me
Br
—CO-Ph


7-130
Me
Et
Br
—CO-Ph


7-131
CF3
Me
Br
—CO-Ph


7-132
CF3
Et
Br
—CO-Ph


7-133
OMe
Me
Br
—CO-Ph


7-134
OMe
Et
Br
—CO-Ph


7-135
NO2
Me
Br
—CO-Ph


7-136
NO2
Et
Br
—CO-Ph


7-137
SO2Me
Me
Br
—CO-Ph


7-138
SO2Me
Et
Br
—CO-Ph


7-139
CH2OMe
Me
Br
—CO-Ph


7-140
CH2OMe
Et
Br
—CO-Ph


7-141
CH2SO2Me
Me
Br
—CO-Ph


7-142
CH2SO2Me
Et
Br
—CO-Ph


7-143
CH2OCH2CH2OMe
Me
Br
—CO-Ph


7-144
CH2OCH2CH2OMe
Et
Br
—CO-Ph


7-145
Cl
Me
I
—CO-Ph


7-146
Cl
Et
I
—CO-Ph


7-147
Me
Me
I
—CO-Ph


7-148
Me
Et
I
—CO-Ph


7-149
CF3
Me
I
—CO-Ph


7-150
CF3
Et
I
—CO-Ph


7-151
OMe
Me
I
—CO-Ph


7-152
OMe
Et
I
—CO-Ph


7-153
NO2
Me
I
—CO-Ph


7-154
NO2
Et
I
—CO-Ph


7-155
SO2Me
Me
I
—CO-Ph


7-156
SO2Me
Et
I
—CO-Ph


7-157
CH2OMe
Me
I
—CO-Ph


7-158
CH2OMe
Et
I
—CO-Ph


7-159
CH2SO2Me
Me
I
—CO-Ph


7-160
CH2SO2Me
Et
I
—CO-Ph


7-161
CH2OCH2CH2OMe
Me
I
—CO-Ph


7-162
CH2OCH2CH2OMe
Et
I
—CO-Ph


7-163
Cl
Me
NO2
—CO-Ph


7-164
Cl
Et
NO2
—CO-Ph


7-165
Me
Me
NO2
—CO-Ph


7-166
Me
Et
NO2
—CO-Ph


7-167
CF3
Me
NO2
—CO-Ph


7-168
CF3
Et
NO2
—CO-Ph


7-169
OMe
Me
NO2
—CO-Ph


7-170
OMe
Et
NO2
—CO-Ph


7-171
NO2
Me
NO2
—CO-Ph


7-172
NO2
Et
NO2
—CO-Ph


7-173
SO2Me
Me
NO2
—CO-Ph


7-174
SO2Me
Et
NO2
—CO-Ph


7-175
CH2OMe
Me
NO2
—CO-Ph


7-176
CH2OMe
Et
NO2
—CO-Ph


7-177
CH2SO2Me
Me
NO2
—CO-Ph


7-178
CH2SO2Me
Et
NO2
—CO-Ph


7-179
CH2OCH2CH2OMe
Me
NO2
—CO-Ph


7-180
CH2OCH2CH2OMe
Et
NO2
—CO-Ph


7-181
Cl
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-182
Cl
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-183
Me
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-184
Me
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-185
CF3
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-186
CF3
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-187
OMe
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-188
OMe
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-189
NO2
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-190
NO2
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-191
SO2Me
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-192
SO2Me
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-193
CH2OMe
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-194
CH2OMe
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-195
CH2SO2Me
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-196
CH2SO2Me
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-197
CH2OCH2CH2OMe
Me
SO2Me
—CH2—CO-






(4-Me-Ph)


7-198
CH2OCH2CH2OMe
Et
SO2Me
—CH2—CO-






(4-Me-Ph)


7-199
Cl
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-200
Cl
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-201
Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-202
Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-203
CF3
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-204
CF3
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-205
OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-206
OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-207
NO2
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-208
NO2
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-209
SO2Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-210
SO2Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-211
CH2OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-212
CH2OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-213
CH2SO2Me
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-214
CH2SO2Me
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-215
CH2OCH2CH2OMe
Me
Cl
—CH2—CO-






(4-Me-Ph)


7-216
CH2OCH2CH2OMe
Et
Cl
—CH2—CO-






(4-Me-Ph)


7-217
Cl
Me
Br
—CH2—CO-






(4-Me-Ph)


7-218
Cl
Et
Br
—CH2—CO-






(4-Me-Ph)


7-219
Me
Me
Br
—CH2—CO-






(4-Me-Ph)


7-220
Me
Et
Br
—CH2—CO-






(4-Me-Ph)


7-221
CF3
Me
Br
—CH2—CO-






(4-Me-Ph)


7-222
CF3
Et
Br
—CH2—CO-






(4-Me-Ph)


7-223
OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


7-224
OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


7-225
NO2
Me
Br
—CH2—CO-






(4-Me-Ph)


7-226
NO2
Et
Br
—CH2—CO-






(4-Me-Ph)


7-227
SO2Me
Me
Br
—CH2—CO-






(4-Me-Ph)


7-228
SO2Me
Et
Br
—CH2—CO-






(4-Me-Ph)


7-229
CH2OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


7-230
CH2OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


7-231
CH2SO2Me
Me
Br
—CH2—CO-






(4-Me-Ph)


7-232
CH2SO2Me
Et
Br
—CH2—CO-






(4-Me-Ph)


7-233
CH2OCH2CH2OMe
Me
Br
—CH2—CO-






(4-Me-Ph)


7-234
CH2OCH2CH2OMe
Et
Br
—CH2—CO-






(4-Me-Ph)


7-235
Cl
Me
I
—CH2—CO-






(4-Me-Ph)


7-236
Cl
Et
I
—CH2—CO-






(4-Me-Ph)


7-237
Me
Me
I
—CH2—CO-






(4-Me-Ph)


7-238
Me
Et
I
—CH2—CO-






(4-Me-Ph)


7-239
CF3
Me
I
—CH2—CO-






(4-Me-Ph)


7-240
CF3
Et
I
—CH2—CO-






(4-Me-Ph)


7-241
OMe
Me
I
—CH2—CO-






(4-Me-Ph)


7-242
OMe
Et
I
—CH2—CO-






(4-Me-Ph)


7-243
NO2
Me
I
—CH2—CO-






(4-Me-Ph)


7-244
NO2
Et
I
—CH2—CO-






(4-Me-Ph)


7-245
SO2Me
Me
I
—CH2—CO-






(4-Me-Ph)


7-246
SO2Me
Et
I
—CH2—CO-






(4-Me-Ph)


7-247
CH2OMe
Me
I
—CH2—CO-






(4-Me-Ph)


7-248
CH2OMe
Et
I
—CH2—CO-






(4-Me-Ph)


7-249
CH2SO2Me
Me
I
—CH2—CO-






(4-Me-Ph)


7-250
CH2SO2Me
Et
I
—CH2—CO-






(4-Me-Ph)


7-251
CH2OCH2CH2OMe
Me
I
—CH2—CO-






(4-Me-Ph)


7-252
CH2OCH2CH2OMe
Et
I
—CH2—CO-






(4-Me-Ph)


7-253
Cl
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-254
Cl
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-255
Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-256
Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-257
CF3
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-258
CF3
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-259
OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-260
OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-261
NO2
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-262
NO2
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-263
SO2Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-264
SO2Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-265
CH2OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-266
CH2OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-267
CH2SO2Me
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-268
CH2SO2Me
Et
NO2
—CH2—CO-






(4-Me-Ph)


7-269
CH2OCH2CH2OMe
Me
NO2
—CH2—CO-






(4-Me-Ph)


7-270
CH2OCH2CH2OMe
Et
NO2
—CH2—CO-






(4-Me-Ph)









B. FORMULATION EXAMPLES


    a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or its salts and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
    b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or its salts, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter and dispersant, and grinding the mixture in a pinned-disk mill.
    c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or its salts with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approximately 255 up to over 277° C.) and grinding the mixture in a bowl mill to a fineness of below 5 microns.
    d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or its salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
    e) Water-dispersible granules are obtained by mixing
    
        75 parts by weight of a compound of the formula (I) and/or its salts,
        10 parts by weight of calcium lignosulfonate,
        5 parts by weight of sodium lauryl sulfate,
        3 parts by weight of polyvinyl alcohol and
        7 parts by weight of kaolin,
        grinding the mixture in a pinned-disk mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.
    
    
    f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
    
        25 parts by weight of a compound of the formula (I) and/or its salts,
        5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
        2 parts by weight of sodium oleoylmethyltaurinate,
        1 part by weight of polyvinyl alcohol,
        17 parts by weight of calcium carbonate and
        50 parts by weight of water,
        subsequently grinding the mixture in a bead mill, and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.
    
    


C. BIOLOGICAL EXAMPLES


    1. Herbicidal Pre-Emergence Effect Against Harmful Plants


Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is scored visually in comparison with untreated controls after an experimental time of 3 weeks has elapsed (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). Here, for example the compounds Nos. 1-2, 2-9, 2-10, 2-11 and 3-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Amaranthus retroflexus and Veronica Persica. 
The compounds Nos. 1-237, 1-238, 2-9, 2-10, 2-237 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus galli. The compounds Nos. 1-10, 2-9 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti and Matricaria inodora. 

    2. Herbicidal Post-Emergence Activity Against Harmful Plants


Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green plant parts in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the test plants have been left to stand under optimal growth conditions in the greenhouse for approximately 3 weeks, the activity of the preparations is scored visually in comparison with untreated controls (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants).
Here, for example the compounds Nos. 1-10, 1-237 and 2-9 show, at an application rate of 80 g/ha, each at least 90% strength activity against Stellaria media and Veronica Persica. The compounds Nos. 1-238, 2-10 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Setaria viridis and Viola tricolor. The compounds Nos. 1-2, 1-237, 1-238 and 2-11 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti and Echinochloa crus galli.

## Claims

1. A 4-(3-alkylsulfinylbenzoyl)pyrazole of the formula (I) or a salt thereof




in which
R1 is (C1-C4)-alkyl,
R2 is hydrogen or (C1-C4)-alkyl,
R3 is (C1-C6)-alkyl,
R4 is hydrogen, (C1-C6)-alkylsulfonyl, (C1-C4)-alkoxy -(C1-C6)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C1-C6)-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy,
X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C6)-cycloalkyl, OR5, OCOR5, OSO2R5, S(O)nR5, SO2OR5, SO2N(R5)2, NR5SO2R5, NR5COR5, (C1-C6)-alkyl-S(O)nR5, (C1-C6)-alkyl-OR5, (C1-C6)-alkyl-OCOR5, (C1-C6)-alkyl-OSO2R5, (C1-C6) -alkyl-SO2OR5, (C1-C6)-alkyl-SO2N(R5)2or (C1-C6)-alkyl-NR5COR5;
Y is fluorine, chlorine, bromine, iodine, nitro or the group SO2R7,
R5 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, phenyl or phenyl-(C1-C6)-alkyl, where the six last-mentioned radicals are substituted by s radicals from the group consisting of hydroxy, mercapto, amino, cyano, nitro, thiocyanato, OR6, SR6, N(R6)2, NOR6, OCOR6, SCOR6, NR6COR6, CO2R6, COSR6, CON(R6)2, (C1)-C4-alkyliminooxy, (C1-C4) -alkylcarbonyl, (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl and (C1-C4) -alkylsulfonyl;
R6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl,
R7 is (C1-C4)-alkyl,
m is 0, 1, 2, 3, 4 or 5,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.

2. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R1 is methyl, ethyl, n-propyl or isopropyl,
R2 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
R3 is (C1-C4)-alkyl,
R4 is hydrogen, (C1-C3)-alkylsulfonyl, (C1-C2)-alkoxy -(C1-C4)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C1-C6)-alkyl or benzyl, each of which is substituted by m methyl groups,
X is nitro, halogen, (C1-C4)-alkyl, trifluoromethyl, (C1-C4) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl,
Y is fluorine, chlorine, bromine, iodine or the group SO2R7,
R7 is methyl, ethyl, n-propyl or isopropyl,
m is 0, 1, 2 or 3.

3. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R1 is methyl or ethyl,
R2 is hydrogen, methyl or ethyl,
R3 is methyl, ethyl, n-propyl or isopropyl,
R4 is hydrogen,
X is nitro, halogen, (C1-C4)-alkyl, trifluoromethyl, (C1-C4) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl,
Y is fluorine, chlorine, bromine, iodine or the group SO2R7,
R7 is methyl or ethyl.

4. A herbicidal composition which comprises a herbicidally active amount of at least one compound of the formula (I) as claimed in claim 1.

5. The herbicidal composition as claimed in claim 4 in a mixture with formulation auxiliaries.

6. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 to plants and/or to a location of unwanted plant growth.

7. A compound of the formula (I) as claimed in claim 1 capable of controlling unwanted plants.

8. A method for using a compound as claimed in claim 7, wherein a compound of the formula (I) is employed for controlling unwanted plants in crops of useful plants.

9. A method as claimed in claim 8, wherein the useful plants are transgenic useful plants.

10. A method for making a herbicidically active 4-(3-alkylsulfinylbenzol) pyrazole as claimed in claim 1 comprising reacting a compound of formula (II),




with a pyrazole,
in which
R3 is (C1-C6)-alkyl
X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)alkynyl, (C3-C6)-haloalkynyl, (C3-C6) cycloalkyl, OR5, OCOR5, OSO2R5,S(O)nR5, SO2OR5,SO2 N(R5)2,NR5SO2R5, NR5COR5, (C1-C6)-alkyl-S(O)nR5, (C1-C6)-alkyl-OR5, (C1-C6)-alkyl-OCOR5, (C1-C6)-alkyl-OSO2R5, (C1-C6) -alkyl-SO2OR5, (C1-C6)-alkyl-SO2N(R5)2 or (C1-C6)-alkyl-NR5COR5;
Y is fluorine, chlorine, bromine, iodine, nitro or the group SO2R7.

11. A compound of formula (Ia) or a salt thereof

12. A herbicidal composition, comprising a herbicidally active amount of at least one compound of formula (Ia) or salt as claimed in claim 11.

13. The herbicidal composition as claimed in claim 12 in a mixture with formulation auxillaries.

14. A method of controlling undesired plants, comprising applying an effective amount of at least one compound of the formula (Ia) as claimed in claim 11 to plants and/or to a location of unwanted plant growth.

15. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
Rl is methyl or ethyl,
R2 is hydrogen,
R3 is methyl, ethyl, n-propyl or isopropyl,
R4 is hydrogen,
X is methyl, chlorine, or methoxymethyl,
Y is chlorine, bromine, or the group SO2R7,
R7 is methyl.

16. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R2 is (C1-C4)-alkyl.

17. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R4 is (C1-C6)-alkylsulfonyl, (C1-C4)-alkoxy-(C1-C6)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C1-C6)-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C1-C4) -alkyl and (C1-C4)-alkoxy.

18. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
X is hydrogen, mercapto, nitro, fluorine, bromine, iodine, cyano, thiocyanato, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C3-C6)-haloalkynyl, (C3-C6)-cycloalkyl, OR5, OCOR5, OSO2R5, S(O)nR5, SO2OR5, SO2N(R5)2, NR5SO2R5, NR5COR5, (C1-C6)-alkyl -S(O)nR5, (C1-C6)-alkyl-OR5, (C1-C6)-alkyl -OCOR5, (C1-C6)-alkyl-OSO2R5, (C1-C6)-alkyl -SO2OR5, (C1-C6)-alkyl-SO2N(R5)2 or (C1-C6)-alkyl-NR5COR5.

19. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
Y is fluorine, chlorine, bromine, iodine, or nitro.