WO2025114252A1 - Substituted isophthalic acid diamides and use thereof as herbicides - Google Patents

Abstract

The invention relates to isophthalic acid diamides of formula (I) as herbicides. In formula (I), X, Y, Z¹, Z² and R^x represent radicals such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

Substituted isophthalic acid diamides and their use as herbicides

The invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and grass weeds in crop plants.

WO2021204665, WO2021204669, WO2021204666 and WO2021204667 describe herbicidally active isophthalic acid diamides which differ essentially in the type of substituents on the two amide functions but also on the phenyl part.

The isophthalic acid diamides specifically disclosed therein do not always exhibit sufficient herbicidal activity and/or tolerance to crop plants. The object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the isophthalic acid diamides according to the invention described below, which carry a haloalkoxy radical in the 4-position.

worin die Symbole und Indizes folgende Bedeutungen haben: The present invention thus relates to isophthalic acid diamides of the formula (I) or salts thereof

where the symbols and indices have the following meanings:

R ^x means (C ₁ -C ₆ )-alkyl,

X represents halogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl,

Y means halogen-(C ₁ -C ₆ )-alkoxy,

Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C 6 )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C 1 -C ₆ )-alkyl, (C _{1 -C 6} )-alkyl-C(O)-(C ₁ -C ₆ )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C 8 -C ₆ )-cycloalkyl carries _m substituents R ¹ ,

R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

R ² and R ³ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, and m means 0, 1, 2 or 3.

In formula (I) and all subsequent formulas, alkyl radicals with more than two carbon atoms can be straight-chain or branched. Alkyl radicals include, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, and hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl. Analogously, alkenyl includes, for example, allyl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methylbut-3-en-l-yl, and l-methylbut-2-en-l-yl. Alkynyl means, for example, propargyl, but-2-yn-l-yl, but-3-yn-l-yl, and l-methyl-but-3-yn-l-yl. The multiple bond can be located in any position of the unsaturated radical. Cycloalkyl means a carbocyclic, saturated ring system with three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

Halogen stands for fluorine, chlorine, bromine or iodine.

The compounds of formula (I) or (II) may exist as stereoisomers depending on the nature and linkage of the substituents. If, for example, one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixtures obtained during preparation by conventional separation methods, for example by chromatographic separation processes. Stereoisomers can also be selectively prepared by using stereoselective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof encompassed by formula (I) or (II) but not specifically defined.

Preferred compounds of formula (I) are those in which the symbols and indices have the following meanings:

R ^x means (C ₁ -C ₆ )-alkyl,

X represents halogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl,

Y means OCF ₃ , OCHF ₂ , OCH ₂ CHF ₂ or OCF ₂ Me,

Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C 1 -C ₆ )-alkyl, (C _{1 -C 6} )-alkyl-C(O)-(C ₁ -C ₆ )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl carries m substituents R ¹ ,

R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

R ² and R ³ independently represent hydrogen, Me, Et or c-Pr, and m means 0, 1, 2 or 3.

Particularly preferred compounds of formula (I) are those in which the symbols and indices have the following meanings:

R ^x means Me or Et,

X is chlorine, bromine, methyl, ethyl or cyclopropyl,

Y means OCF ₃ , OCHF ₂ or OCH ₂ CHF ₂ , and

Z ¹ and Z ² independently each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH ₂ , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1-

Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH ₂ , EtC(O)CH ₂ , c-PrC(O) _CH2 , MeNHC(O) _CH2 , EtNHC(O) _CH2 or c-PrNHC(O) _CH2 .

In all formulas mentioned below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).

worin die Symbole und Indizes folgende Bedeutungen haben: Compounds of formula (II) are novel and are very suitable as intermediates for the preparation of the compounds of formula (I) according to the invention. The present invention thus further relates to compounds of formula (II),

where the symbols and indices have the following meanings:

L means halogen or R ⁴ O,

X represents halogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl,

Y means halogen-(C ₁ -C ₆ )-alkoxy, Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C 6 )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C 1 -C ₆ )-alkyl, (C _{1 -C 6} )-alkyl-C(O)-(C ₁ -C ₆ )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl carries _m substituents R ¹ ,

R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

R ² and R ³ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl,

R ⁴ represents hydrogen or (C ₁ -C ₆ )-alkyl, and m represents 0, 1, 2 or 3.

Preferred compounds (II) are those in which

L means chlorine, methoxy or hydroxy,

X is chlorine, bromine, methyl, ethyl or cyclopropyl,

Y means OCF ₃ , OCHF ₂ or OCH ₂ CHF ₂ and

Z ¹ and Z ² independently each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH ₂ , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1-

Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH ₂ , EtC(O)CH ₂ , c-PrC(O) _CH2 , MeNHC(O) _CH2 , EtNHC(O) _CH2 or c-PrNHC(O) _CH2 .

In all formulas mentioned below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).

Compounds of the general formula (I) according to the invention can be prepared, for example, as also described in WO2012/028579, by reacting the compounds of the general formula (IIb: compounds II, where L=hydroxy) according to the invention with substituted aminotetrazoles:

The synthesis of the compounds of general formula (IIb) can be carried out, for example, according to the following scheme and methods known to the person skilled in the art:

Collections of compounds of formula (I) and/or their salts, which can be synthesized by the above-mentioned reactions, can also be prepared in a parallelized manner. This can be done manually, partially automated, or fully automated. For example, it is possible to automate the reaction procedure, the workup, or the purification of the products or intermediates. Overall, this refers to a procedure such as that described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Günther Jung), Wiley Publishers 1999, pages 1 to 34.

A range of commercially available devices can be used for parallelized reaction execution and workup, for example Calpyso reaction blocks (Caylpso 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, Massachusetts 02451, USA. For the parallelized purification of compounds of formula (I) and their salts or of intermediates obtained during preparation, chromatography apparatus is available, for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The equipment listed results in a modular approach in which the individual work steps are automated, but manual operations must be performed between them. This can be circumvented by using partially or fully integrated automation systems, in which the respective automation modules are operated, for example, by robots. Such automation systems can be purchased, for example, from Caliper, Hopkinton, MA 01748, USA. The implementation of individual or multiple synthesis steps can be supported by the use of polymer-supported reagents/scavenger resins. Several experimental protocols are described in the literature, for example, in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

In addition to the methods described here, the preparation of compounds of formula (I) and their salts can be carried out completely or partially by solid-phase-assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis, or of a synthesis adapted for the corresponding procedure, are bound to a synthesis resin. Solid-phase-assisted synthesis methods are adequately described in the specialist literature, e.g., Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998, and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use of solid-phase-assisted synthesis methods allows for a number of well-known protocols, which can be carried out manually or automatically. The reactions can be carried out, for example, using IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA.

Both in the solid and liquid phases, the implementation of individual or multiple synthesis steps can be supported by the use of microwave technology. A number of experimental protocols are described in the literature, for example, in "Microwaves in Organic and Medicinal Chemistry" (editors: C. O. Kappe and A. Stadler), Wiley, 2005.

Preparation according to the processes described here yields compounds of formula (I) and their salts in the form of collections of substances called libraries. The present invention also relates to libraries containing at least two compounds of formula (I) and their salts.

The compounds of the invention exhibit excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds. Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other permanent organs are effectively controlled by the active ingredients.

The present invention therefore also relates to a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds according to the invention are applied to the plants (e.g. harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable crop plants), the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the area on which the plants grow (e.g. the cultivated area). The compounds according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence or post-emergence methods. Some representatives of the mono- and dicotyledonous weed flora which can be controlled by the compounds according to the invention are mentioned, without the mention being intended to imply a restriction to specific 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 and Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, C ₆ ntaurea, 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 and Xanthium.

If the compounds according to the invention are applied to the soil surface before germination, either the emergence of weed seedlings is completely prevented or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.

When the active ingredients are applied to the green parts of the plant using the post-emergence method, growth stops after treatment and the weeds remain in the growth stage present at the time of application or die completely after a certain time, so that in this way weed competition that is harmful to the crops is eliminated very early and sustainably.

Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, 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 only insignificantly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate thereof. For these reasons, the present compounds are very suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plantings.

In addition, the compounds according to the invention, depending on their respective chemical structure and the applied rate, have excellent growth regulatory properties in cultivated plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant components and facilitate harvesting, for example, by inducing desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as it can reduce or completely prevent lodging, for example.

Due to their herbicidal and plant growth-regulating properties, the active ingredients can also be used to control weeds in crops of plants modified genetically or through conventional mutagenesis. Transgenic plants are generally characterized by particularly advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria, or viruses. Other special properties affect, for example, the harvested crop in terms of quantity, quality, storability, composition, and specific ingredients. Transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known.

With regard to transgenic crops, the use of the compounds according to the invention is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybean, rapeseed, potato, cassava, tomato, pea and other vegetables.

Preferably, the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.

Conventional approaches to producing new plants with modified traits compared to existing plants include classical breeding methods and the creation of mutants. Alternatively, new plants with modified traits can be created using genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have described genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf. e.g. EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or sulfonylureas (EP-A-0257993, US-A-5013659), Transgenic crops, such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259). Transgenic crops with modified fatty acid composition (WO 91/13972). Genetically modified crops with new ingredients or secondary substances, e.g., new phytoalexins, which cause increased disease resistance (EPA 309862, EPA0464461). Genetically modified plants with reduced photorespiration that exhibit higher yields and greater stress tolerance (EPA 0305398).

Transgenic crops that produce pharmaceutically or diagnostically important proteins (“molecular pharming”), transgenic crops that are characterized by higher yields or better quality, transgenic crops that are characterized by a combination of, for example, the above-mentioned new properties (“gene stacking”).

Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced 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).

For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base substitutions can be performed, partial sequences removed, or natural or synthetic sequences added. Adapters or linkers can be attached to the DNA fragments to connect them together. See, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker, "Genes and Clones," VCH Weinheim, 2nd ed., 1996.

The production of plant cells with reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect, or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the aforementioned gene product. For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA Sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (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). Expression of nucleic acid molecules can also occur in the organelles of plant cells.

The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can, in principle, be plants of any plant species, i.e., both monocotyledonous and dicotyledonous.

Transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

Preferably, the compounds according to the invention can be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl lisoxazoles and analogous active ingredients.

When the active ingredients according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops.

The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crops.

The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating compositions containing the compounds according to the invention. The compounds according to the invention can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified. Possible formulation options include, for example, 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 dressings, granules for broadcast and soil application, granules (GR) in the form of microgranules, spray granules, emulsifiable granules, and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "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 necessary formulation aids such as inert materials, surfactants, solvents and other 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", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

Wettable powders are preparations that are evenly dispersible in water. In addition to the active ingredient, they contain a diluent or inert substance as well as ionic and/or non-ionic surfactants (wetting agents, dispersants), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyltaurine. To produce the wettable powders, the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers). can be used for example: Alkylarylsulfonic acid calcium salts such as

Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters,

Alkylaryl polyglycol ether, fatty alcohol polyglycol ether,

Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as

Sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, such as those listed above for the other formulation types.

Emulsions, e.g. 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, such as those already listed above for the other formulation types.

Granules can be produced either by spraying the active ingredient onto adsorbent, granulated inert material or by applying active ingredient concentrates to the surface of carrier materials such as sand, kaolinite, or granulated inert material using adhesives, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules—if desired, in a mixture with fertilizers.

Water-dispersible granules are usually produced by conventional processes such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the production of disc, fluidized bed, extruder and spray granules see e.g. procedures in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of pesticides, 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.

The agrochemical preparations generally contain 0.1 to 99 wt.%, in particular 0.1 to 95

% by weight, compounds according to the invention. In wettable powders, for example, the active ingredient concentration is approximately 10 to 90 wt.%, with the remainder (100 wt.%) consisting of conventional formulation ingredients. In emulsifiable concentrates, the active ingredient concentration can be approximately 1 to 90, preferably 5 to 80 wt.%. Dust-like formulations contain

1 to 30 wt.% active ingredient, preferably 5 to 20 wt.% active ingredient; sprayable solutions contain approximately 0.05 to 80, preferably 2 to 50 wt.% active ingredient. In water-dispersible granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In water-dispersible granules, for example, the active ingredient content is between 1 and 95 wt.%, preferably between 10 and 80 wt.%.

In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH value and viscosity.

On the basis of these formulations, combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and/or growth regulators, can also be produced, e.g. in the form of a ready-to-use formulation or as a tank mix.

For application, the commercially available formulations are diluted in the usual way, e.g., with water for wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances prior to application.

The required application rate of the compounds of formula (I) varies depending on external conditions such as temperature, humidity, the type of herbicide used, etc. It can vary within wide limits, e.g., between 0.001 and 1.0 kg/ha or more of active ingredient, but is preferably between 0.005 and 750 g/ha.

The compounds of formula (I) according to the invention can also be used as a mixture with other herbicides, if required. Examples of suitable combination partners for the compounds of formula (I) in mixture formulations or in tank mixes include known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, or which act as plant growth regulators, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual," 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and literature cited therein. Known herbicides or plant growth regulators that can be combined with compounds of formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name or code number). These always include all application forms, such as acids, salts, esters, and isomers, such as stereoisomers and optical isomers. One and, in some cases, several application forms are mentioned as examples:

Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor,

Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsulfuron, Beflubutamide, (S)-(-)- Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazone, Bentazone-Sodium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Sodium, Bipyrazone, Bispyribac, Bispyribac sodium, Bixlozone, Bromacil, Bromacil lithium, Bromacil sodium, Bromobutide, Bromofenoxime, Bromoxynil, Bromoxynil butyrate, Bromoxynil potassium, Bromoxynil heptanoate and Bromoxynil octanoate, Busoxinone, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazone, Carfentrazone ethyl, Chloramben, Chloramben ammonium, Chloramben diolamine, Chloramben methyl, Chloramben methylammonium, Chloramben sodium, Chlorbromuron, Chlorfenac, Chlorfenac ammonium, Chlorfenac sodium, Chlorfenprop, Chlorfenprop methyl, Chlorflurenol, Chlorflurenol methyl, Chloridazon, Chlorimuron, Chlorimuron ethyl, Chlorophthalim, Chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, ie (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)- Cinmethylin, ie ( 1 R,2S ,4S)-4-isopropyl- 1 -methyl-2- [(2-methylbenzyl)oxy] -7 -oxabicyclo[2.2.1]heptane, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop-propargyl, Clomazone, Clomeprop, Clopyralid, Clopyralid-methyl, Clopyralid-olamine, Clopyralid-potassium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloate, Cyclopyranil, Cyclopyrimorate, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazine, 2,4-D (as well as the ammonium, Butotyl, Butyl, Choline, Diethylammonium, dimethylammonium, diolamine, doboxyl, dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecyl ammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salts thereof). 2,4-DB, 2,4-DB-butyl, 2,4-DB -dimethylammonium, 2,4-DB -isooctyl, 2,4-DB potassium and 2,4-DB sodium, Daimuron (Dymron), Dalapon, Dalapon calcium, Dalapon magnesium, Dalapon sodium, Dazomet, Dazomet sodium, n- Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl pyrazolate (DTP), Dicamba and its salts (e.g. Dicamba biproamine, Dicamba N,N-bis(3-aminopropyl)methylamine, Dicamba butotyl, Dicamba- choline, dicamba diglycolamine, dicamba dimethylammonium, dicamba diethanolaminemmonium, dicamba diethylammonium, dicamba isopropylammonium, dicamba methyl, dicamba monoethanolamine, dicamba olamine, dicamba potassium, dicamba sodium, dicamba triethanolamine), dichlobenil, 2-(2,4-Dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-potassium, Dichlorprop-sodium, Dichlorprop-P, Dichlorprop-P-dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-potassium, Dichlorprop-sodium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr sodium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamide, Diquat, Diquat-Dibromide, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC sodium, endothal, endothal diammonium, Endothelial dipotassium,

Endothal Disodium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-Ethyl, Ethoxysulfuron, Etobenzanide, F- 5231, ie N-[2-Chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethanesulfonamide, F-7967, ie 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamide, Flamprop, Flamprop-Isoproyl, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Florasulam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop-Methyl, Fluazifop-P, Fluazifop-P-Butyl, Flucarbazone, Flucarbazone sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-Ethyl, Flumetsulam, Flumiclorac, Flumiclorac-Pentyl, Flumioxazin, Fluometuron, Flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, Fluroxypyr-Meptyl, Flurtamon, Fluthiacet, Fluthiacet-Methyl, Fomesafen, Fomesafen Sodium, Foramsulfuron, Foramsulfuron Sodium, Fosamine, Fosamine Ammonium, Glufosinate, Glufosinate Ammonium, Glufosinate Sodium, E-Glufosinate Ammonium, L-Glufosinate Sodium, Glufosinate-P-sodium, Glufosinate-P- Ammonium, glyphosate, glyphosate ammonium, glyphosate isopropyl ammonium, glyphosate diammonium, glyphosate dimethyl ammonium, glyphosate potassium, glyphosate sodium, glyphosate sesquinodium and glyphosate trimesium, H-9201, ie O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop-Methyl, Haloxyfop-P-Methyl, Haloxifop sodium, hexazinone, HNPC-A8169, ie prop-2-yn-l-yl (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoate, HW-02, i.e. l-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, hydantocidin, Imazamethabenz, Imazamethabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapic ammonium, Imazapyr, Imazapyr isopropyl ammonium, Imazaquin, imazaquin-ammonium, imazaquin-methyl, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, lodosulfuron, lodosulfuron-methyl, lodosulfuron-methyl-sodium, ioxynil, loxynil-lithium, -octanoate, -potassium and sodium, Ipfencarbazone, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Carbutilat, KUH-043, i.e. 3-({[5-(difluoromethyl)-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazole, Ketospiradox, Ketospiradox- Potassium, Lactofen, Lenacil, Linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, - 2-ethylhexyl, -ethyl, -isobutyl, isoctyl, -isopropyl, -isopropylammonium, -methyl, olamine, -potassium, - sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, Mecoprop-dimethylammonium, Mecoprop-diolamine, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop-Isoctyl, Mecoprop-Methyl, Mecoprop-potassium, Mecoprop-sodium, and Mecoprop-trolamine, Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl and -Potassium, Mefenacet, Mefluidide, Mefluidide Diolamin, Mefluidide Potassium, Mesosulfuron, Mesosulfuron-Methyl, Mesosulfuron Sodium, Mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozoline, Methyl isothiocyanate, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinate, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT-5950, ie N-[3-Chloro-4-(l-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, Napropamide, NC-310, ie 4-(2,4- Dichlorobenzoyl)-l-methyl-5-benzyloxypyrazole, NC-656, ie 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-l,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[l,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, neburone, nicosulfuron, nonanoic acid (pelargonic acid), norflurazone, oleic acid (fatty acids), orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat dichloride, Paraquat dimethyl sulfate, Pebulat, Pendimethalin, Penoxsulam, Pentachlorophenol, Pentoxazone, Pethoxamide, Petroleum oil, Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram-Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Potassium, Picloram-Triethylammonium, Picloram-Tripromine, Picloram-Trolamine, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Prop-isochlor, Propoxycarbazone, Propoxycarbazone-sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyrasulfotol, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz- Propyl, Pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop-P-Tefuryl, QYM201, ie l-{2-chloro-3-[(3-cyclopropyl- 5-hydroxy- 1-methyl- lH-pyrazol-4-yl)carbonyl] -6-(trifluoromethyl)phe-nyl }piperidin-2-one, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, i.e. l-ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, ie l-[7-fluoro-3-oxo-4-(prop-2-in-l- yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g. TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumetone, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazone-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralate, topramezone, tralkoxydim, triafamon, Tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifluralin, triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Urea Sulfate, Vernolate, 2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, ethyl-[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1 (2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1- yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-Methoxyethoxy)methyl]-6-methylpyridin-3-yl} carbonyl)cyclohexan-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1 -benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl] -1 H-pyrazol-5-yl propan-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1 H-pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl } - 1 -methyl- 1 H-pyrazole-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate; Cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridin-2-carboxylate, prop-2-yn-l-yl 3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylic acid, benzyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2- carboxylate, Ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, Methyl 4-amino-3-chloro-5-fluoro-6-(7 -fluoro- 1 -isobutyryl- 1H-indol-6-yl)pyridine-2-carboxylate, Methyl 6-( 1 -acetyl-7 - fluor-lH-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[l-(2,2-dimethylpropanoyl)-7-fluoro-lH-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5- fluoro-6-[7-fluoro-l-(methoxyacetyl)-lH-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, Butyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridin-2-carboxylate, 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl- l,2-oxazol-3-yl)-4-hydroxy-l-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin-2,4(lH,3H)-dione, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l-en- 1 -yl)carbonyl] - 1 -methylquinazolin-2,4( 1 H,3H)-dione, 2- [2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl] -3-hydroxycyclohex-2-en- 1 -one, 1 -(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin- 1 - ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4- (pyridazin-3-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(Pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(Pyridazin-3-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-Carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-Carboxyethyl)-4-(l,3,4-thiadiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), methyl (2R)-2-{ [(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2S)- 2- { [(E)-( { 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2R/S)-2-{ [(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)- 2-(trifluoromethyl)benzaldehyde-O- { 2,6-bis [(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl } oxime, 2-fluoro- N-(5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl- 1 - { 2-chloro-4-fluoro- 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy } cyclopropanecarboxylate, 2-methoxy-2-oxoethyl- 1 - { 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy {cyclopropane carboxylate, { [( 1 - { 2-chloro-4-fluoro- 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-Bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, methyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl } -3a,4,5,6-tetrahydro-6aH-cyclopenta[d] [ 1 ,2]oxazole-6a-carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazole-6a-carboxylate.

Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-Ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl] -3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-( 1 -hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-dienoic acid, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-l,3- dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (Isopropylidene)-aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)-aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)-aminooxyacetic acid 2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-ylcarboxylic acid N-methyl- 1-aminocyclopropyl-l-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-

Aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 5-aminoethyl uvulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canalin, catechin and catechins (e.g. (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [( _C8H13NO5 ) _n CAS No. 1398-61-4] and _chitosan molecules _[ ( _C5H11NO4 ) _n , CAS No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop- _l -enyl)propionic _acid , l-[2-(4-Cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-Cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-Cyclopropenylmethanol, Daminozide, Dazomet, Dazomet sodium, n-Decanol, Dikegulac, Dikegulac sodium, Endothal, Endothal di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), Ethephon, l-Ethylcyclopropene, Flumetralin, Flurenol, Flurenol butyl, Flurenol methyl, Flurprimidol, Forchlorfenuron, Gibberellic acid, Inabenfid, Indole-3-acetic acid (IAA), 4-Indol-3-ylbutyric acid, Isoprothiolane, Probenazole, Jasmonic acid, Jasmonic acid esters or other derivatives (e.g. Jasmonic acid methyl ester, jasmonic acid ethyl ester), lipochitooligosaccharides (LCO, sometimes also referred to as symbiotic nodulation signals (Nod or Nod factors) or Myc factors, consist of an oligosaccharide backbone of ß-l,4-linked IV-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end. As can be seen from the literature, LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain, as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-Methylabscisic acid, l-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[l,2-b]furan-2-one and related lactones as described in EP2248421, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, Paclobutrazol, 4-phenylbutyric acid and its salts (e.g. sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid and salicyclic acid methyl ester, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-l-yl)propanoate, sodium 3-(cycloprop-l-en-l-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, Tsitodef, Uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine.

Although the compounds of formula (I) according to the invention generally have good selectivity towards crop plants, it may be useful to combine them with known safeners.

Safeners which, in combination with the compounds of formula (I) according to the invention and optionally in Combinations with other active ingredients such as insecticides, acaricides, herbicides, fungicides as listed above can be used, are preferably selected from the group consisting of:

wobei die Symbole und Indizes folgende Bedeutungen haben: n_A ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; SI) Compounds of the formula (SI),

where the symbols and indices have the following meanings: n _A is a natural number from 0 to 5, preferably 0 to 3;

R _A ¹ is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, nitro or (C ₁ -C ₄ )haloalkyl;

W _A is an unsubstituted or substituted divalent heterocyclic radical from the group of the partially saturated or aromatic five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (WA ¹ ) to (WA ⁵ ), m _A is 0 or 1 ;

R _A ² is OR _A ³ , SR _A ³ or NR _A ³ R _A ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked to the carbonyl group in (S1) via the N atom and is unsubstituted or substituted by radicals from the group (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _A ³ , NHR _A ⁴ or N(CH ₃ ) ₂ , in particular of the formula OR _A ³ ;

R _A ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;

R _A ⁴ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₁ -C ₆ )alkoxy or substituted or unsubstituted phenyl;

R _A ⁵ is H, (C ₁ -C ₃ )alkyl, (C ₁ -C ₃ )haloalkyl, (C ₁ -C ₄ )alkoxy(C ₁ -C ₃ )alkyl, cyano or COOR _A ⁹ , wherein

R _A ⁹ hydrogen, (C ₁ -C ₃ )alkyl, (C ₁ -C ₃ )haloalkyl, (C ₁ -C ₄ )alkoxy-(C ₁ -C ₄ )alkyl, (C ₁ -C ₆ )hydroxyalkyl, (C ₃ -C ₁₂ )cycloalkyl or tri-(C ₁ -C ₄ )-alkyl-silyl; R _A ⁶ , R _A ⁷ , R _A ⁸ are identical or different and are hydrogen, (C ₁ -C ₃ )alkyl, (C ₁ -C ₃ )haloalkyl, (C ₃ - C ₁₂ )cycloalkyl or substituted or unsubstituted phenyl;

R _A ¹⁰ is H, (C ₃ -C ₁₂ )cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (Sl ^a ), preferably

Compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S 1 - 1)

("Mefenpyr-diethyl"), and related compounds as described in WO-A-91/07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (Sl ^b ), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (Sl-2), ethyl l-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (Sl-3), ethyl l-(2,4-dichlorophenyl)-5-(l,l-dimethylethyl)pyrazole-3-carboxylate (Sl-4) and related compounds as described in EP-A-333 131 and EP-A-269 806; c) derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl ^c ), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-5), methyl l-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-6) and related compounds as described, for example, in EP-A-268554; d) compounds of the triazolecarboxylic acid type (Sl ^d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. ethyl l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazole-3-carboxylate (Sl-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; e) Compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl ^-8 ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Sl-9) and related compounds as described in WO-A-91/08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-11) ("Isoxadifen-ethyl") or -n-propyl ester (Sl-12) or 5-(4-Fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-13), as described in patent application WO-A-95/07897. f) Compounds of the triazolyloxyacetic acid derivative type (Sl ^f ), preferably compounds such as methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (Sl-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Sl-15) or methyl {[5-(4-chloro-2- fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-16) or {[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-17) or methyl {[l-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-18) or {[l-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-19), as described in patent application WO2021105101

wobei die Symbole und Indizes folgende Bedeutungen haben: S2) quinoline derivatives of the formula (S2),

where the symbols and indices have the following meanings:

R _B ¹ is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, nitro or (C ₁ -C ₄ )haloalkyl; n _B is a natural number from 0 to 5, preferably 0 to 3;

R _B ² is OR _B ³ , SR _B ³ or NR _B ³ R _B ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked via the N atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _B ³ , NHR _B ⁴ or N(CH ₃ ) ₂ , in particular of the formula OR _B ³ ;

R _B ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;

R _B ⁴ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₁ -C ₆ )alkoxy or substituted or unsubstituted phenyl;

T _B is a (C ₁ or C ₂ )-alkanediyl chain which is unsubstituted or substituted by one or two (C ₁ -C ₄ ) alkyl radicals or by [(C ₁ -C ₃ )-alkoxy]-carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid type (S2 ^a ), preferably (5-chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (l,3-dimethyl-but-l-yl) ester (S2-2),

(5-Chloro-8-quinolinoxy)acetic acid-4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid-l- allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetic acid allyl ester (S2-7), (5-chloro-8-quinolinoxy)acetic acid 2-(2-propylidene-iminoxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, as well as (5-chloro-8-quinolinoxy)acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts as described in WO-A-2002/34048; b) compounds of the (5-chloro-8-quinolinoxy)malonic acid (S2 ^b ) type, preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester,

Diallyl (5-chloro-8-quinolinoxy)malonic acid, methyl ethyl (5-chloro-8-quinolinoxy)malonic acid and related compounds as described in EP-A-0 582 198.

wobei die Symbole und Indizes folgende Bedeutungen haben: S3) Compounds of formula (S3)

where the symbols and indices have the following meanings:

R _C ¹ is (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ )haloalkenyl, (C ₃ -C ₇ )cycloalkyl, preferably dichloromethyl;

R _C ² , R _C ³ are identical or different and are hydrogen, (C ₁ -C ₄ )alkyl, (C ₂ -C ₄ )alkenyl,

(C ₂ -C ₄ )alkynyl, (C ₁ -C ₄ )haloalkyl, (C ₂ -C ₄ )haloalkenyl, (C ₁ -C ₄ )alkylcarbamoyl-(C ₁ -C ₄ )alkyl, (C ₂ - C ₄ )alkenylcarbamoyl-(C ₁ -C ₄ )alkyl, (C 1 -C 4 )alkoxy-(C ₁ -C ₄ )alkyl, dioxolanyl-(C _{1 -C 4} )alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R _C ² and R _C ³ _together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-acting safeners), such as: B. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-l-dichloroacetyl-3,3,8a- trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R)-isomer (S3-11).

worin die Symbole und Indizes folgende Bedeutungen haben: S4) N-acylsulfonamides of formula (S4) and their salts,

where the symbols and indices have the following meanings:

X _D is CH or N;

R _D ¹ is CO-NR _D ⁵ R _D ⁶ or NHCO-R _D ⁷ ;

R _D ² is halogen, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl or (C ₁ -C ₄ )-alkylcarbonyl;

R _D ³ is hydrogen, (C ₁ -C ₄ )alkyl, (C ₂ -C ₄ )alkenyl or (C ₂ -C ₄ )alkynyl;

R _D ⁴ is halogen, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, (C ₃ -C ₆ )-cycloalkyl, phenyl, (C ₁ -C ₄ )-alkoxy, cyano, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )alkoxycarbonyl or (C ₁ -C ₄ )alkylcarbonyl;

R _D ⁵ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₅ -C ₆ )-cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group nitrogen, oxygen and sulfur, where the last seven radicals are substituted by VD substituents from the group halogen, (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₆ )haloalkoxy, (C ₁ -C ₂ )alkylsulfinyl, (C ₁ -C ₂ )alkylsulfonyl, (C ₃ - C ₆ )cycloalkyl, (C ₁ -C ₄ )alkoxycarbonyl, (C ₁ -C ₄ ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ )haloalkyl;

R _D ⁶ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₂ -C ₆ )alkenyl or (C ₂ -C ₆ )alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy and (C ₁ -C ₄ )alkylthio, or

R _D ⁵ and R _D ⁶ together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

worin R _D ⁷ is hydrogen, (C ₁ -C ₄ )alkylamino, di-(C ₁ -C ₄ )alkylamino, (C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, where the last two radicals are substituted by VD substituents from the group halogen, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₆ )haloalkoxy and (C ₁ -C ₄ )alkylthio and in the case of cyclic radicals also (C ₁ -C ₄ )alkyl and (C ₁ -C ₄ )haloalkyl are substituted; n _D is 0, 1 or 2; m _D is 1 or 2; v _D is 0, 1, 2 or 3; of these, preference is given to compounds of the N-acylsulfonamide type, e.g. of the following formula (S4 ^a ), which are known, for example, from WO-A-97/45016

wherein

R _D ⁷ (C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, where the last two radicals are substituted by VD substituents from the group halogen, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₆ )haloalkoxy and (C ₁ -C ₄ )alkylthio and in the case of cyclic radicals also (C ₁ -C ₄ )alkyl and (C ₁ -C ₄ )haloalkyl;

z.B. solche worin R _D ⁴ is halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, CF _3; m _D is 1 or 2; v _D is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4 ^b ), which are known, for example, from WO-A-99/16744,

e.g. those in which

R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 2-OMe ("Cyprosulfamide", S4-1),

R _D ⁵ = Cyclopropyl and (R _D ⁴ ) = 5-Cl-2-OMe is (S4-2),

R _D ⁵ = ethyl and (R _D ⁴ ) = 2-OMe is (S4-3),

R _D ⁵ = Isopropyl and (R _D ⁴ ) = 5-Cl-2-OMe is (S4-4) and

worin R _D ⁵ = isopropyl and (R _D ⁴ ) = 2-OMe is (S4-5). and compounds of the N-acylsulfamoylphenylurea type of formula (S4 ^C ), which are known, for example, from EP-A-365484,

wherein

R _D ⁸ and R _D ⁹ independently of one another are hydrogen, (C ₁ -C ₃ )alkyl, (C ₃ -C ₃ )cycloalkyl, (C ₃ -C ₆ )alkenyl,

(C ₃ -C ₆ )alkynyl,

R _D ⁴ represents halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF ₃ m _D 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.

S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. l-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, l-methyl-3-(2-thienyl)-l,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1 ,2-dihydro-quinoxalin-2-one hydrochloride, 1 -(2-

Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630.

worin die Symbole und Indizes folgende Bedeutungen haben: R_E ¹, R_E ² sind unabhängig voneinander Halogen, (C₁-C₄) Alkyl, (C₁-C₄) Alkoxy, (C₁-C₄)Haloalkyl, (C₁-C₄)Alkylamino, Di-(C₁-C₄)Alkylamino, Nitro; S7) Compounds of formula (S7) as described in WO-A-1998/38856

where the symbols and indices have the following meanings: R _E ¹ , R _E ² are independently halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ )haloalkyl, (C ₁ -C ₄ )alkylamino, di-(C ₁ -C ₄ )alkylamino, nitro;

A _E is COOR _E ³ or COSR _E ⁴

R _E ³ , R _E ⁴ are independently hydrogen, (C ₁ -C ₄ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₄ )alkynyl, cyanoalkyl, (C ₁ -C ₄ )haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n _E ¹ is 0 or 1 n _E ² , n _E ³ are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, diphenylmethoxyacetate ethyl ester, diphenylmethoxyacetate methyl ester (CAS Reg. No. 41858-19-9) (S7-1).

S8) Compounds of formula (S8) as described in WO-A-98/27049

Wherein

X _F CH or N, n _F in the case that X _F =N, an integer from 0 to 4 and in the case that X _F =CH, an integer from 0 to 5 ,

R _F ¹ halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₄ )haloalkoxy, nitro, (C ₁ -C ₄ )alkylthio, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ ) Alkoxycarbonyl, optionally substituted. phenyl, optionally substituted phenoxy,

R _F ² hydrogen or (C ₁ -C ₄ )alkyl

R _F ³ represents hydrogen, (C ₁ -C ₃ )alkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ )alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, preferably compounds wherein

X _F CH, n _F is an integer from 0 to 2 ,

R _F ¹ halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₄ )haloalkoxy,

R _F ² hydrogen or (C ₁ -C ₄ )alkyl,

R _F ³ represents hydrogen, (C ₁ -C ₃ )alkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ )alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or salts thereof.

S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.

worin S10) Compounds of the formulas (S10 ^a ) or (S10 ^b ) as described in WO-A-2007/023719 and WO-A-2007/023764

wherein

R _G ¹ halogen, (C ₁ -C ₄ )alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃

Y _G , Z _G independently of each other O or S, n _G an integer from 0 to 4,

R _G2 ( _{C1 -C16} )alkyl, ( _{C2 -C6} )alkenyl, ( _{C3 -C6} )cycloalkyl, aryl ^; benzyl, halobenzyl,

R _G ³ is hydrogen or (C ₁ -C ₆ )alkyl.

Si l) Active substances of the oxyimino compound type (Sil) known as seed dressing agents, such as "Oxabetrinil" ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sll-1), known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim" (l-(4-chlorophenyl)-2,2,2-trifluoro-l-ethanone-O-(l,3-dioxolan-2-ylmethyl)-oxime) (Sl l-2), known as a seed dressing safener for millet against damage from metolachlor, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.

12) Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.

513) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in sown rice, "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CF 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a corn safener against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-l,3-dioxolane) (S13-5) from Nitrokemia, which is known as a corn safener, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphodithioate) (S13-7), "Dietholate" (O,O-Diethyl O-phenylphosphorothioate) (S13-8), "Mephenate" (4-Chlorophenyl methyl carbamate) (S13-9).

514) Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crops such as rice, such as: B. "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-l-carbothioate), which is known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (l-(l-methyl-l-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage from the herbicide Imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage from some herbicides, "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.

worin R_H ¹ einen (C₁-C₆)Haloalkylrest bedeutet und S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008/131861 and WG-A-2008/131860

wherein R _H ¹ represents a (C ₁ -C ₆ )haloalkyl radical and

R _H ² is hydrogen or halogen and

R _H ³ , R _H ⁴ independently of one another are hydrogen, (C ₁ -C ₁₆ )alkyl, (C ₂ -C ₁₆ )alkenyl or (C ₂ -C ₁₆ )alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C ₁ -C ₄ )alkoxy, (C ₁ -C ₄ )haloalkoxy, (C ₁ -C ₄ )alkylthio, (C ₁ -C ₄ )alkylamino, di[(C ₁ -C ₄ )alkyl]amino, [(C ₁ -C ₄ )alkoxy]carbonyl, [(C ₁ -C ₄ )haloalkoxy]carbonyl, (C ₃ -C ₆ )cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, is substituted, or (C ₃ -C ₆ )cycloalkyl, (C ₄ -C ₆ )cycloalkenyl, (C ₃ -C ₆ )C cycloalkyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C ₄ -C ₆ )cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C ₁ -C ₄ )alkyl, (C 1 -C ₄ )haloalkyl, (C ₁ -C ₄ ) Alkoxy, (Cl-C ₄ )haloalkoxy, (Cl-C ₄ )alkylthio, (Cl-C ₄ )alkylamino, di[(Cl-C ₄ )alkyl]amino, [(C ₁ -C ₄ )alkoxy]carbonyl, [(Cl-C ₄ )haloalkoxy]carbonyl, (C ₃ -C ₆ )cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or

R _H ³ is (C ₁ -C ₄ )alkoxy, (C ₂ -C ₄ )alkenyloxy, (C ₂ -C ₆ )alkynyloxy or (C ₂ -C ₄ )haloalkoxy and

R _H ⁴ is hydrogen or (C ₁ -C ₄ )-alkyl or

R _H ³ and R _H ⁴ together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy and (C ₁ -C ₄ ) alkylthio.

S16) Active ingredients that are primarily used as herbicides but also have a safener effect on crops, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), l-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).

Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocetmexyl, benoxacor, dichlormid and metcamifen. The following examples illustrate the invention.

A. Chemical Examples

Synthesis of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1):

Step 1: Preparation of l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4): 20.35 ml (145.2 mmol) of diisopropylamine were placed in 250 ml of tetrahydrofuran under argon, and 79.4 ml (127.1 mmol) of n-butyllithium (1.6 M solution in hexane) were added dropwise at -60°C. The solution was stirred for 1 h. The mixture was then briefly warmed to -40°C, and a solution of 25 g (90.8 mmol) of l-bromo-2-chloro-4-(trifluoromethoxy)benzene (3) in 60 ml of tetrahydrofuran was added dropwise at -60°C. The solution was stirred for 1 h. Then, 11.5 ml (181.5 mmol) of iodomethane were added dropwise, and the mixture was stirred for another 1 h. The still-cold reaction solution was mixed with 800 ml of water and adjusted to pH 1 with concentrated hydrochloric acid. After extraction with ethyl acetate, the organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→80/20). This gave 25.00 g (95%) of l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4). ¹ H NMR (400 MHz, DMSO-d ₆ ): δ = 7.79 (d, 1H); 7.35 (d, 1H); 2.39 (s, 3H).

Step 2: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5):

18.91 g (65.33 mmol) of l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4) were dissolved in 150 mL of dimethylformamide, and 11.7 g (130.65 mmol) of copper(I) cyanide were added at room temperature. The resulting reaction mixture was heated to reflux for 12 h. It was then poured into 1 l of cold water and treated with ethyl acetate. After vigorous stirring for 10 min, the mixture was filtered and the phases were separated. The organic phase was dried and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→60/40). This gave 11.83 g (77%) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5). ¹ H NMR (400 MHz, DMSO-d ₆ ): δ = 8.01 (d, 1H); 7.60 (br d, 1H); 2.37 (s, 3H).

Step 3: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6):

10.92 g (46.35 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5) were dissolved in a solution of 17.73 g (443 mmol) of sodium hydroxide in 180 ml of water and heated to reflux for 6 h. The mixture was then left to stand overnight at room temperature. The mixture was then washed with dichloromethane and the aqueous phase was adjusted to pH 1 with 2 M hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic phase was separated, dried and evaporated. This gave 11.07 g (94%) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6). ¹ H NMR (400 MHz, DMSO-d ₆ ): δ = 13.59 (br s, 1H); 7.72 (d, 1H); 7.45 (br d, 1H); 2.35 (s, 3H).

Step 4: Preparation of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7): 22.08 g (86.73 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6) were placed in 400 ml of dichloromethane and 3 ml of dimethylformamide and treated at room temperature with 11.58 ml (13.09 mmol) of oxalyl chloride were slowly added. The mixture was then stirred at room temperature for 1 h. After 20 ml (1734.5 mmol) of methanol were added dropwise, the mixture was stirred at room temperature for 3 h and the solution was evaporated to dryness. The residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→60/40). This gave 21.26 g (91%) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7). ¹ H NMR (400 MHz, DMSO-d ₆ ): δ = 7.75 (d, 1H); 7.49 (br d, 1H); 3.88 (s, 3H); 2.36 (s, 3H).

Step 5: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8): 10.42 g (38.79 mmol) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7) was dissolved in 100 g of chlorobenzene, and 13.81 g (77.58 mmol) of N-bromosuccinimide and 0.64 g (3.88 mmol) of AIBN were added. The reaction mixture was stirred at 120°C for 8 h. It was then evaporated, and the residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→60/40). 13.25 g (98%) of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8) were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.92 (d, 1H); 7.57 (br d, 1H); 4.75 (s, 2H); 3.89 (s, 3H).

Step 6: Preparation of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1): 26.20 g (75 mmol) of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8) were initially charged in 300 ml of acetonitrile, and 26.50 g (226 mmol) of N-methylmorpholine N-oxide were added portionwise at 10°C. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 12 h. The mixture was then evaporated, the residue was taken up in water, and extracted several times with ethyl acetate. The organic phases were combined, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→80/20). 16.39 g (77%) of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1) were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 10.37 (s, 1H); 8.12 (d, 1H); 7.66 (br d, 1H); 3.91 (s, 3H).

Synthesis of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2):

Step 1: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10): 10 g (47.35 mmol) of commercially available methyl 2-chloro-4-hydroxy-3-methylbenzoate (9) were added portionwise to a solution of 19.93 g of potassium hydroxide in 75 ml of acetonitrile and 75 ml of water at 0°C. Then, 17.52 ml (94.71 mmol) of diethyl [bromo(difluoro)methyl]phosphonate were added, and the mixture was stirred at 0°C for 1 h. After addition of ethyl acetate, the organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→85/15). 9.80 g (82%) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.71 (d, 1H); 7.33 (t, 1H); 7.27 (d, 1H); 3.86 (s, 3H); 2.31 (s, 3H). Step 2: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11): 20.65 g (82.39 mmol) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) was dissolved in 200 g of chlorobenzene, and 29.33 g (164.79 mmol) of N-bromosuccinimide and 1.35 g (8.24 mmol) of AIBN were added. The reaction mixture was stirred at 120°C for 8 h. It was then evaporated, and the residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→60/40). 26.47 g (97%) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11) were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): 5 = 7.89 (d, 1H); 7.48 (t, 1H); 7.36 (d, 1H); 4.73 (s, 2H); 3.88 (s, 3H).

Step 3: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2): 5.96 g (18 mmol) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11) were initially charged in 200 ml of acetonitrile, and 6.36 g (54 mmol) of N-methylmorpholine N-oxide were added portionwise at 10°C. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 12 h. The mixture was then evaporated, the residue was taken up in water, and extracted several times with ethyl acetate. The organic phases were combined, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane/ethyl acetate 100/0→60/40). 4.33 g (90%) of methyl 2-chloro-4-(difluoromethoxy)-3-formyl benzoate (1) were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 10.34 (s, 1H); 8.06 (d, 1H); 7.44 (d, 1H); 7.39 (t, 1H); 3.89 (s, 3H).

Examples of the preparation of the compounds (II) and (I) according to the invention:

Preparation of 2-chloro-N ³ -cyclopropyl-N ¹ -(l-ethyl-lH-tetrazol-5-yl)-4-(trifluoromethoxy)isophthalamide (2-24):

Step 1: Preparation of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid: 6.70 g (23.71 mmol) of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1) were initially dissolved in 200 mL of acetone, and a 2.5M solution of chromium(VI) oxide (11.38 mL, 28.45 mmol) in a 3:1 mixture of water and sulfuric acid was slowly added dropwise at 0°C. The reaction mixture was then stirred at room temperature for 12 h. After adding isopropanol to remove excess oxidant, the reaction mixture was evaporated. The residue was taken up in water and extracted with ethyl acetate; the organic phase was separated, dried, and evaporated. 6.85 g (92%) of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid were obtained. ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 14.50 (br s, 1H); 8.01 (d, 1H); 7.63 (br d, 1H); 3.89 (s, 3H).

Step 2: Preparation of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24): 1.04 g (3.48 mmol) of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid were placed in 50 ml of dichloromethane and treated with one drop of dimethylformamide and then with 0.47 ml (5.22 mmol) Oxalyl chloride was added. The reaction solution was stirred at room temperature for 1 h, then evaporated, and the residue was taken up with toluene and evaporated again. This residue was dissolved in 10 ml of dry dichloromethane and added dropwise at 0°C to a solution of 0.36 ml (5.22 mmol) of cyclopropylamine and 1.2 ml (6.96 mmol) of Hünig's base in 40 ml of dry dichloromethane. The mixture was then stirred at room temperature for 4 h. After dilution with dichloromethane, the mixture was washed with 2M hydrochloric acid, the organic phase was separated, dried, and evaporated. This gave 1.13 g (96%) of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24).

Step 3: Preparation of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24): 1.25 g (3.70 mmol) of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24) were initially charged in 50 ml of methanol, and 2.8 ml (5.55 mmol) of 2M sodium hydroxide solution were added at room temperature. The reaction mixture was stirred at room temperature for 12 h and then evaporated. The residue was taken up with water, and the aqueous phase was adjusted to pH 1 with 2M hydrochloric acid. The organic phase was separated, dried, and evaporated. 1.12 g (89%) of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24) was obtained.

Step 4: Preparation of 2-chloro-N ³ -cyclopropyl-N ¹ -(l-ethyl-lH-tetrazol-5-yl)-4-

(trifluoromethoxy)isophthalamide (2-24): 200 mg (0.61 mmol) of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24) and 110.4 mg (0.92 mmol) of 5-amino-1-ethyl-1H-tetrazole were initially charged in 3 ml of pyridine, and 0.085 ml (0.92 mmol) of oxalyl chloride was added dropwise at room temperature. The reaction solution was stirred for 12 h at room temperature. After addition of 10 ml of water, the mixture was stirred for a further 10 min and then extracted with dichloromethane. The organic phase was separated, dried and evaporated. The residue was purified by chromatography (HPLC, CI 8, gradient: acetonitrile/water (+0.05% trifluoroacetic acid) 10/90→400/0). 85 mg (31%) of 2-chloro-N ³ -cyclopropyl-N ¹ -(l-ethyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)isophthalamide (2-24) were obtained.

The examples listed in the following tables were prepared analogously to the methods described above or are available analogously to the methods described above. These compounds are particularly preferred.

The abbreviations used mean:

Me = Methyl Et = Ethyl Pr = Propyl i-Pr = iso-Propyl c-Pr = cyclo-Propyl Bu = Butyl i-Bu = iso-Butyl Ph = Phenyl c-Bu = cyclo-Butyl

Table 1: Compounds of the formula (I) according to the invention, wherein R ^x represents a methyl group and the other substituents have the meanings given below.

Table 2: Compounds of the formula (I) according to the invention, wherein R ^x represents an ethyl group and the other substituents have the meanings given below.

Table 3: Compounds of the formula (II) according to the invention, wherein L is methoxy and the other substituents have the meanings given below,

Table 4: Compounds of the formula (II) according to the invention, wherein L is hydroxy and the other substituents have the meanings given below,

Table 5: Compounds of the formula (II) according to the invention, wherein L is chlorine and the other substituents have the meanings given below

Zu zahlreichen in obigen Tabellen genannten erfindungsgemäßen Verbindungen der Formel (I) und

For numerous compounds of the formula (I) and

(II) NMR data are disclosed below for further characterization:

Example no. 1-1: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.66 (br s, 1H); 8.51 (q, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 3.98 (s, 3H); 2.79 (d, 3H); 2.34 (s, 3H);

Example no. 1-2: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.65 (br s, 1H); 8.60 (t, 1H); 7.78 (d, 1H); 7.41 (br d, 1H); 3.98 (s, 3H); 3.28 (m, 2H); 2.35 (s, 3H); 1.11 (t, 3H);

Example no. 1-6: ¹ H-NMR (400 MHz, DMS Od ₆ ): δ = 11.66 (br s, 1H); 8.67 (d, 1H); 7.41 (br d, 1H); 3.98 (s, 3H); 2.82 (m, 1H);2.34 (s, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Example no. 1-10: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.71 (br s, 1H); 8.52 (br q, 1H); 7.79 (d, 1H); 7.43 (br d, 1H); 3.99 (s, 3H); 2.79 (d, 3H); 2.73 (q, 2H); 1.15 (t, 3H);

Example no. 1-11: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.71 (br s, 1H); 8.62 (br t, 1H); 7.79 (d, 1H); 7.43 (br d, 1H); 3.99 (s, 3H); 3.29 (m, 2H); 2.75 (q, 2H); 1.17 (t, 3H); 1.11 (t, 3H);

Example no. 1-15: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.68 (br s, 1H); 8.67 (br d, 1H); 7.79 (d, 1H); 7.40 (br d, 1H); 3.99 (s, 3H); 3.82 (m, 1H); 2.74 (q, 2H); 1.16 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H);

Example no. 1-19: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 8.70 (q, 1H); 7.91 (d, 1H); 7.62 (d, 1H); 4.00 (s, 3H); 2.80 (d, 3H);

Example no. 1-20: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.28 (m, 2H); 1.11 (t, 3H);

Example no. 1-21: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.23 (m, 2H); 1.52 (m, 2H); 0.92 (t, 3H);

Example no. 1-22: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.67 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.06 (m, 1H); 4.00 (s, 3H); 1.14 (d, 6H);

Example no. 1-23: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 8.85 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.17 (m, 2H); 0.99 (m, 1H); 0.44 (m, 2H); 0.24 (m, 2H);

Example no. 1-24: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.84 (d, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 2.82 (m, 1H); 0.73 (m, 2H); 0.49 (m, 2H);

Example no. 1-25: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.97 (s, 1H); 7.89 (d, 1H); 7.59 (d, 1H); 3.99 (s, 3H); 1.39 (s, 3H); 0.70 (m, 2H); 0.62 (m, 2H); Example no. 1-26: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.89 (br s, 1H); 8.93 (br s, 1H); 7.88 (d, 1H); 7.59 (br d, 1H); 3.99 (s, 3H); 1.62 (q, 2H); 0.97 (t, 3H); 0.68 (m, 2H); 0.64 (m, 2H);

Example no. 1-27: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.89 (br s, 1H); 8.93 (s, 1H); 7.88 (d, 1H); 7.59 (br d, 1H); 3.99 (s, 3H); 1.58 (m, 2H); 1.48 (m, 2H); 0.90 (t, 3H); 0.68 (m, 2H); 0.63 (m, 2H);

Example no. 1-29: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.89 (br s, 1H); 9.08 (s, 1H); 7.89 (d, 1H); 7.58 (br d, 1H); 3.99 (s, 3H); 3.53 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.78 (m, 2H); 0.72 (m, 2H);

Example no. 1-32: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 4.50 (d, 2H); 4.00 (s, 3H); 0.95 (m, 2H); 0.83 (m, 2H);

Example no. 1-35: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 9.41 (s, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.11 (q, 2H); 4.00 (s, 3H); 1.48 (m, 2H); 1.19 (t, 3H); 1.10 (m, 2H);

Example no. 1-37: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.93 (br s, 1H); 9.82 (s, 1H); 7.97 (d, 1H); 7.67 (br d, 1H); 4.00 (s, 3H); 1.65 (m, 2H); 1.20 (m, 2H);

Example no. 1-38: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 9.38 (s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 3.99 (s, 3H); 3.06 (s, 1H); 1.21 (m, 2H); 1.03 (m, 2H);

Example no. 1-42: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.92 (br s, 1H); 9.54 (s, 1H); 7.93 (d, 1H); 7.63 (br d, 1H); 7.49 (m, 1H); 6.40 (m, 1H); 4.00 (s, 1H); 1.33 (m, 2H); 1.16 (m, 2H);

Example no. 1-45: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.91 (br s, 1H); 9.16 (t, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.12 (d, 2H); 4.00 (s, 3H); 2.15 (s, 3H);

Example no. 1-46: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.92 (br s, 1H); 9.15 (t, 1H); 7.93 (d, 1H); 7.63 (d, 1H); 4.13 (d, 2H); 4.00 (s, 3H); 2.50 (q, 2H); 0.97 (t, 3H);

Example no. 1-48: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 9.04 (t, 1H); 7.91 (d, 1H); 7.76 (m, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.89 (d, 2H); 2.64 (d, 3H);

Example no. 1-49: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 9.02 (t, 1H); 7.91 (d, 1H); 7.79 (br t, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.88 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

Example no. 1-50: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.99 (t, 1H); 7.95 (br d, 1H); 7.90 (d, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.85 (d, 2H); 2.65 (m, 1H); 0.64 (m, 2H); 0.41 (m, 2H);

Example no. 1-51: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.93 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.01 (s, 3H); 3.05 (s, 3H); 2.82 (s, 3H);

Example no. 1-52: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.93 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.01 (s, 3H); 3.62 and 3.45 and 3.14 (3x m, 2H); 3.02 and 2.80 (2x s, 3H); 1.14 and 1.07 (2x t, 3H); Example no. 1-53: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.93 (br s, 1H); 7.94 (m, 1H); 7.66 (m, 1H); 4.01 (s, 3H); 3.01 (s, 3H); 2.90 (m, 1H); 0.90-0.50 (m, 4H);

Example no. 1-63: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.58 (br s, 1H); 8.40 (q, 1H); 7.74 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 3.97 (s, 3H); 2.77 (d. 3H); 2.31 (s, 3H);

Example no. 1-64: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.58 (br s, 1H); 8.47 (t, 1H); 7.74 (d, 1H); 7.23 (t, 1H); 7.21 (d, 1H); 3.97 (s, 3H); 3.26 (m, 2H); 2.33 (s, 3H); 1.11 (t, 3H);

Example no. 1-68: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.57 (br s, 1H); 8.54 (d, 1H); 7.73 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 3.97 (s, 3H); 2.81 (m, 1H); 2.31 (s, 3H); 0.70 (m, 2H); 0.49 (m, 2H);

Example no. 1-72: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.61 (br s, 1H); 8.39 (br q, 1H); 7.74 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 3.98 (s, 3H); 2.78 (d, 3H); 2.72 (q, 2H); 1.14 (t, 3H);

Example no. 1-73: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.60 (br s, 1H); 8.48 (br t, 1H); 7.74 (d, 1H); 7.23 (t, 1H); 7.20 (d, 1H); 3.98 (s, 3H); 3.27 (m, 1H); 2.74 (q, 2H); 1.16 (t, 3H); 1.11 (t, 3H);

Example no. 1-77: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.60 (br s, 1H); 8.55 (br d, 1H); 7.74 (d, 1H); 7.22 (t, 1H); 7.20 (d, 1H); 3.98 (s, 3H); 2.82 (m, 1H); 2.72 (q, 2H); 1.14 (t, 3H); 0.70 (m, 2H); 0.48 (m, 2H);

Example no. 1-81: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.57 (q, 1H); 7.84 (d, 1H); 7.39 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 2.78 (d, 3H);

Example no. 1-82: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.63 (t, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 3.99 (s, 3H); 3.27 (m, 2H); 1.11 (t, 3H);

Example no. 1-83: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.63 (t, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.21 (m, 2H); 1.52 (m, 2H); 0.92 (t, 3H);

Example no. 1-84: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.82 (br s, 1H); 8.52 (d, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.27 (t, 1H); 4.05 (m, 1H); 3.99 (s, 3H); 1.14 (d, 6H);

Example no. 1-86: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 8.69 (d, 1H); 7.37 (d, 1H); 7.30 (t, 1H); 3.99 (s, 3H); 2.80 (m, 1H); 0.71 (m, 2H); 0.49 (m, 2H);

Example no. 1-87: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.82 (br s, 1H); 8.82 (s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.25 (t, 1H); 3.98 (s, 3H); 1.39 (s, 3H); 0.71 (m, 2H); 0.61 (m, 2H);

Example no. 1-88: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 8.78 (s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 7.27 (t, 1H); 3.98 (s, 3H); 1.62 (q, 2H); 0.97 (t, 3H); 0.69 (m, 2H); 0.61 (m, 2H); Example no. 1-89: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 8.76 (br s, 1H); 7.78 (d, 1H); 7.31 (d, 1H); 7.24 (t, 1H); 3.94 (s, 3H); 1.58 (m, 2H); 1.49 (m, 2H); 0.90 (t, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

Example no. 1-90: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 8.78 (br s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 7.27 (t, 1H); 3.98 (s, 3H); 1.97 (m, 1H); 1.50 (d, 2H); 0.93 (d, 6H); 0.72 (m, 2H); 0.60 (m, 2H);

Example no. 1-91: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 8.94 (br s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 7.24 (t, 1H); 3.98 (s, 3H); 3.53 (s, 2H); 3.49 (q, 2H); 1.11 (t, 3H); 0.77 (m, 2H); 0.72 (m, 2H);

Example no. 1-92: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.82 (br s, 1H); 8.82 (s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.29 (t, 1H); 3.98 (s, 3H); 3.51 (t, 2H); 3.22 (s, 3H); 1.86 (t, 2H); 0.69 (m, 4H);

Example no. 1-94: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 9.09 (s, 1H); 7.84 (d, 1H); 7.37 (d, 1H); 7.26 (t, 1H); 4.49 (d, 2H); 3.99 (s, 3H); 0.93 (m, 2H); 0.84 (m, 2H);

Example no. 1-95: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.51 (s, 1H); 7.86 (d, 1H); 7.39 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.31 (s, 3H); 1.05 (m, 2H); 0.87 (m, 2H);

Example no. 1-96: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 9.50 (br s, 1H); 7.85 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.64 (q, 2H); 1.10 (t, 3H); 1.06 (m, 2H); 0.87 (m, 2H);

Example no. 1-97: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.28 (s, 1H); 7.86 (d, 1H); 7.39 (d, 1H); 7.29 (t, 1H); 4.11 (q, 2H); 3.99 (s, 3H); 1.46 (m, 2H); 1.20 (t, 3H); 1.11 (m, 2H);

Example no. 1-98: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.82 (br s, 1H); 8.99 (s, 1H); 7.82 (d, 1H); 7.33 (d, 1H); 7.19 (t, 1H); 4.06 (q, 2H); 3.98 (s, 3H); 2.73 (s, 2H); 1.18 (t, 3H); 0.80 (m, 2H); 0.76 (m, 2H);

Example no. 1-99: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 9.65 (s, 1H); 7.90 (d, 1H); 7.43 (d, 1H); 7.34 (t, 1H); 3.99 (s, 3H); 1.63 (m, 2H); 1.20 (m, 2H);

Example no. 1-100: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.88 (br s, 1H); 9.20 (br s, 1H); 7.80 (d, 1H); 7.33 (d, 1H); 7.24 (t, 1H); 3.93 (s, 3H); 3.03 (s, 1H); 1.19 (m, 2H); 1.04 (m, 2H);

Example no. 1-101: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.87 (br s, 1H); 9.37 (s, 1H); 7.87 (d, 1H); 7.42 (d, 1H); 7.40 (t, 1H); 7.30 (m, 3H); 7.19 (m, 2H); 4.00 (s, 3H); 1.29 (m, 4H);

Example no. 1-102: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 9.31 (s, 1H); 7.80 (d, 1H); 7.79 (m, 1H); 7.40 (m, 1H); 7.30 (m, 3H); 7.15 (t, 1H); 3.96 (s, 3H); 1.17 (m, 4H); Example no. 1-103: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 9.44 (s, 1H); 7.88 (d, 1H); 7.42 (m, 1H); 7.40 (t, 1H); 7.31 (d, 1H); 7.20 (m, 3H); 4.00 (s, 3H); 1.35 (m, 2H); 1.30 (m, 2H);

Example no. 1-104: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.41 (s, 1H); 7.86 (d, 1H); 7.48 (m, 1H); 7.40 (d, 1H); 7.36 (t, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 3.99 (s, 3H); 1.32 (m, 2H); 1.17 (m, 2H);

Example no. 1-105: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.30 (br s, 1H); 7.85 (d, 1H); 7.56 (m, 1H); 7.49 (s, 1H); 7.40 (d, 1H); 7.37 (t, 1H); 6.33 (m, 1H); 3.99 (s, 3H); 1.14 (m, 2H); 1.12 (m, 2H);

Example no. 1-107: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.09 (d, 2H); 3.99 (s, 3H); 2.16 (s, 3H);

Example no. 1-108: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.85 (br s, 1H); 9.06 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.10 (d, 2H); 3.99 (s, 3H); 2.55 (q, 2H); 0.96 (t, 3H);

Example no. 1-110: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.93 (t, 1H); 7.85 (d, 1H); 7.65 (m, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 3.88 (d, 2H); 2.64 (d, 3H);

Example no. 1-111: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.92 (t, 1H); 7.85 (d, 1H); 7.67 (bt, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 3.88 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

Example no. 1-113: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 7.87 (d, 1H); 7.46 (d, 1H); 7.42 (t, 1H); 4.00 (s, 3H); 3.04 (s, 3H); 2.81 (s, 3H);

Example no. 1-114: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 7.86 (d, 1H); 7.44 (m, 2H); 3.99 (s, 3H); 3.52 and 3.13 (2x m, 2H); 3.01 and 2.78 (2x s, 3H); 1.14 and 1.04 (2x t, 3H);

Example no. 1-115: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.86 (br s, 1H); 7.86 (d, 1H); 7.46 (t, 1H); 7.43 (d, 1H); 4.00 (s, 3H); 3.00 and 2.71 (2x s, 3H); 2.90 and 2.62 (2x m, 1H); 0.82-0.46 (m, 4H);

Example no. 1-125: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.90 (br s, 1H); 8.97 (br s, 1H); 7.89 (d, 1H); 7.60 (br d, 1H); 3.99 (s, 3H); 2.57 (m, 1H); 1.88-1.62 (m, 6H); 0.68 (m, 4H);

Example no. 1-126: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 8.83 (br s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.28 (t, 1H); 3.99 (s, 3H); 2.57 (m, 1H); 1.87-1.63 (m, 6H); 0.67 (m, 4H);

Example no. 1-127: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.61 (br s, 1H); 8.43 (q, 1H); 7.69 (d, 1H); 7.43 (d, 1H); 4.02 (s, 3H); 2.79 (d, 3H); 2.14 (m, 1H); 8.83 (m, 2H); 0.60 (m, 2H);

Example no. 1-128: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.61 (br s, 1H); 8.52 (t, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4-02 (s, 3H); 3.30 (m, 2H); 2.17 (m, 1H); 1.12 (t, 3H); 0.84 (m, 2H); 0.63 (m, 2H); Example no. 1-129: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.61 (br s, 1H); 8.59 (d, 1H); 7.68 (d, 1H); 7.42 (d, 1H); 4.02 (s, 3H); 2.80 (m, 1H); 2.15 (m, 1H); 0.84 (m, 2H); 0.71 (m, 2H); 0.61 (m, 2H); 0.51 (m, 2H);

Example no. 1-130: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.54 (br s, 1H); 8.33 (br q, 1H); 7.63 (d, 1H); 7.23 (d, 1H); 7.20 (t, 1H); 4.01 (s, 3H); 2.78 (d, 3H); 2.12 (m, 1H); 0.82 (m, 2H); 0.58 (m, 2H);

Example no. 1-131: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.54 (br s, 1H); 8.40 (br t, 1H); 7.62 (d, 1H); 7.23 (d, 1H); 7.18 (t, 1H); 4.01 (s, 3H); 3.28 (m, 2H); 2.15 (m, 1H); 1.13 (t, 3H); 0.82 (m, 2H); 0.61 (m, 2H);

Example no. 1-132: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.53 (br s, 1H); 8.47 (d, 1H); 7.62 (d, 1H); 7.22 (d, 1H); 7.18 (t, 1H); 4.01 (s, 3H); 2.79 (m, 1H); 2.13 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.59 (m, 2H); 0.51 (m, 2H);

Example no. 1-133: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.70 (br s, 1H); 8.35 (q, 1H); 7.75 (d, 1H); 7.29 (d, 1H); 6.34 (dd, 1H); 4.45 (td, 2H); 3.97 (s, 3H); 2.75 (d, 3H);

Example no. 1-134: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.69 (br s, 1H); 8.42 (t, 1H); 7.75 (d, 1H); 7.28 (d, 1H); 6.34 (dd, 1H); 4.44 (td, 2H); 3.97 (s, 3H); 3.24 (m, 2H); 1.10 (t, 3H);

Example no. 1-135: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.69 (br s, 1H); 8.49 (d, 1H); 7.75 (d, 1H); 7.26 (d, 1H); 6.34 (dd, 1H); 4.42 (td, 2H); 3.97 (s, 3H); 2.75 (m, 1H); 0.68 (m, 2H); 0.49 (m, 2H);

Example no. 2-1: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.55 (br s, 1H); 8.51 (q, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 4.33 (q, 2H); 2.79 (d, 3H); 2.33 (s, 3H); 1.46 (t, 3H);

Example no. 2-2: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.56 (br s, 1H); 8.59 (t, 1H); 7.77 (d, 1H); 7.40 (br d, 1H); 4.32 (q, 2H); 3.27 (m, 2H); 2.35 (s, 3H); 1.45 (t, 3H); 1.11 (t, 3H);

Example no. 2-6: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.54 (br s, 1H); 8.66 (d, 1H); 7.77 (d, 1H); 7.41 (br d, 1H); 4.33 (q, 2H); 2.82 (m, 1H); 2.34 (s, 3H); 1.46 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H);

Example no. 2-10: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.58 (br s, 1H); 8.51 (br q, 1H); 7.78 (d, 1H); 7.43 (br d, 1H); 4.34 (q, 2H); 2.79 (d, 3H); 2.73 (q, 2H); 1.47 (t, 3H); 1.16 (t, 3H);

Example no. 2-11: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.58 (br s, 1H); 8.60 (br t, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 4.34 (q, 2H); 2.29 (m, 2H); 2.75 (q, 2H); 1.47 (t, 3H); 1.17 (t, 3H); 1.11 (t, 3H);

Example no. 2-15: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.57 (br s, 1H); 8.67 (br d, 1H); 7.77 (d, 1H); 7.42 (br d, 1H); 4.34 (q, 2H); 2.83 (m, 1H); 2.74 (m, 2H); 1.46 (t, 3H); 1.16 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H); Example no. 2-19: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 8.70 (q, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 2.80 (d, 3H); 1.47 (t, 3H);

Example no. 2-20: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.29 (m, 2H); 1.46 (t, 3H); 1.11 (t, 3H);

Example no. 2-21: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 8.77 (t, 1H); 7.89 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.23 (m, 2H); 1.53 (m, 2H); 1.47 (t, 3H); 0.92 (t, 3H);

Example no. 2-22: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 8.67 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 4.06 (m, 1H); 1.47 (t, 3H); 1.15 (d, 6H);

Example no. 2-23: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 8.85 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.17 (m, 2H); 1.47 (t, 3H); 1.00 (m, 1H); 0.44 (m, 2H); 0.25 (m, 2H);

Example no. 2-24: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 8.84 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 2.82 (m, 1H); 1.46 (t, 3H); 0.74 (m, 2H); 0.49 (m, 2H);

Example no. 2-25: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 8.97 (s, 1H); 7.88 (d, 1H); 7.59 (d, 1H); 4.36 (q, 2H); 1.46 (t, 3H); 1.39 (s, 3H); 0.70 (m, 2H); 0.63 (m, 2H);

Example no. 2-27: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 8.93 (s, 1H); 7.87 (d, 1H); 7.59 (br d, 1H); 4.35 (q, 2H); 1.57 (m, 2H); 1.48 (m, 2H); 1.46 (t, 3H); 0.90 (t, 3H); 0.70 (m, 2H); 0.63 (m, 2H);

Example no. 2-27: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 9.38 (s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 4.36 (q, 2H); 3.06 (s, 1H); 1.46 (t, 3H); 1.21 (m, 2H); 1.03 (m, 2H);

Example no. 2-29: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 9.08 (s, 1H); 7.88 (d, 1H); 7.58 (d, 1H); 4.36 (q, 2H); 3.53 (s, 2H); 3.48 (q, 2H); 1.46 (t, 3H); 1.11 (t, 3H); 0.79 (m, 2H); 0.72 (m, 2H);

Example no. 2-32: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 9.23 (s, 1H); 7.90 (d, 1H); 7.61 (br d, 1H); 4.50 (d, 2H); 4.36 (q, 2H); 1.46 (t, 3H); 0.96 (m, 2H); 0.83 (m, 2H);

Example no. 2-35: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 9.41 (s, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.36 (q, 2H); 4.11 (q, 2H); 1.47 (m, 5H); 1.19 (t, 3H); 1.10 (m, 2H);

Example no. 2-37: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 9.82 (s, 1H); 7.97 (d, 1H); 7.67 (br d, 1H); 4.36 (q, 2H); 1.65 (m, 2H); 1.46 (t, 3H), 1.20 (m, 2H);

Example no. 2-42: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 9.54 (s, 1H); 7.92 (d, 1H); 7.63 (br d, 1H); 7.49 (m, 1H); 6.40 (m, 1H); 6.25 (m, 1H); 4.36 (q, 2H); 1.47 (t, 3H); 1.33 (m, 2H); 1.16 (m, 2H); Example no. 2-45: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 9.16 (t, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.36 (q, 2H); 4.13 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

Example no. 2-46: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.81 (br s, 1H); 9.15 (t, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.36 (q, 2H); 4.13 (d, 2H); 2.51 (q, 2H); 1.47 (t, 3H); 0.97 (t, 3H);

Example no. 2-48: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 9.04 (t, 1H); 7.90 (d, 1H); 7.77 (m, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.89 (d, 2H); 2.64 (d, 3H); 1.46 (t, 3H);

Example no. 2-49: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 9.02 (t, 1H); 7.90 (d, 1H); 7.79 (br t, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.88 (d, 2H); 3.13 (m, 2H); 1.46 (t, 3H); 1.04 (t, 3H);

Example no. 2-50: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.80 (br s, 1H); 9.00 (t, 1H); 7.96 (br d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.85 (d, 2H); 2.65 (m, 1H); 1.47 (t, 3H); 0.64 (m, 2H); 0.41 (m, 2H);

Example no. 2-51: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.37 (d, 2H); 3.05 (s, 3H); 2.83 (s, 3H); 1.47 (t, 3H);

Example no. 2-52: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 7.93 (d, 1H); 7.67 (d, 1H); 4.37 (q, 2H); 3.62 and 3.46 and 3.14 (3x m, 2H); 3.02 and 2.80 (2x s, 3H); 1.47 (t, 3H); 1.14 and 1.07 (2x t, 3H);

Example no. 2-53: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.83 (br s, 1H); 7.93 (m, 1H); 7.65 (m, 1H); 4.37 (q, 2H); 3.02 (s, 3H); 2.91 (m, 1H); 1.47 (t, 3H); 0.88-0.51 (m, 4H);

Example no. 2-63: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.47 (br s, 1H); 8.40 (q, 1H); 7.73 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 4.32 (q, 2H); 2.78 (d, 3H); 2.31 (s, 3H); 1.46 (t, 3H);

Example no. 2-64: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.46 (br s, 1H); 8.47 (t, 1H); 7.73 (d, 1H); 7.23 (t, 1H); 7.22 (d, 1H); 4.32 (q, 2H); 3.27 (m, 2H); 2.33 (s, 3H); 1.46 (t, 3H); 1.11 (t, 3H);

Example no. 2-68: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.46 (br s, 1H); 8.53 (d, 1H); 7.72 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 4.32 (q, 2H); 2.81 (m, 1H); 2.31 (s, 3H); 1.46 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

Example no. 2-72: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.49 (br s, 1H); 8.39 (br q, 1H); 7.73 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 4.33 (q, 2H); 2.78 (d, 3H); 2.71 (q, 2H); 1.46 (t, 3H); 1.14 (t, 3H);

Example no. 2-73: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.49 (br s, 1H); 8.48 (br t, 1H); 7.73 (d, 1H); 7.23 (t, 1H); 7.22 (d, 1H); 4.33 (q, 2H); 3.27 (m, 2H); 2.74 (q, 2H); 1.46 (t, 3H); 1.16 (t, 3H); 1.11 (t, 3H);

Example no. 2-77: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.48 (br s, 1H); 8.55 (br d, 1H); 7.73 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 4.32 (q, 2H); 2.82 (m, 1H); 2.72 (m, 2H); 1.46 (t, 3H); 1.14 (t, 3H); 0.71 (m, 2H); 0.48 (m, 2H); Example no. 2-81: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.84 (br s, 1H); 8.57 (q, 1H); 7.84 (d, 1H); 7.39 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 2.78 (d, 3H);

Example no. 2-82: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.73 (br s, 1H); 8.63 (t, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.35 (q, 2H); 3.27 (m, 2H); 1.46 (t, 3H); 1.11 (t, 3H);

Example no. 2-83: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.63 (t, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.21 (m, 2H); 1.52 (m, 2H); 1.46 (t, 3H); 0.92 (t, 3H);

Example no. 2-84: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.52 (d, 1H); 7.82 (d, 1H); 7.37 (d, 1H); 7.27 (t, 1H); 4.35 (q, 2H); 4.05 (m, 1H); 1.46 (t, 3H); 1.14 (d, 6H);

Example no. 2-86: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.69 (d, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.35 (q, 2H); 2.81 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.50 (m, 2H);

Example no. 2-87: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.71 (br s, 1H); 8.82 (s, 1H); 7.81 (d, 1H); 7.36 (d, 1H); 7.25 (t, 1H); 4.35 (q, 2H); 1.46 (t, 3H); 1.39 (s, 3H); 0.72 (m, 2H; 0.62 (m, 2H);

Example no. 2-88: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.78 (s, 1H); 7.81 (d, 1H); 7.36 (d, 1H); 7.27 (t, 1H); 4.35 (q, 2H); 1.62 (q, 2H); 1.46 (t, 3H); 0.97 (t, 3H); 0.69 (m, 2H); 0.61 (m, 2H);

Example No. 2-89: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.78 (br s, 1H); 7.80 (d, 1H);

7.35 (d, 1H); 7.26 (t, 1H); 4.34 (q, 2H); 3.32 (s, 3H); 1.58 (m, 2H); 1.50 (m, 2H); 1.46 (t, 3H); 0.90 (t,

3H); 0.70 (m, 2H); 0.61 (m, 2H);

Example No. 2-90: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.78 (br s, 1H); 7.80 (d, 1H);

7.34 (d, 1H); 7.27 (t, 1H); 4.34 (q, 2H); 1.96 (m, 1H); 1.49 (d, 2H); 1.46 (t, 3H); 0.93 (d, 6H); 0.73 (m,

2H); 0.60 (m, 2H);

Example no. 2-91: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.94 (s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 7.24 (t, 1H); 4.35 (q, 2H); 3.53 (s, 2H); 3.49 (q, 2H); 1.46 (t, 3H); 1.11 (t, 3H); 0.77 (m, 2H); 0.72 (m, 2H);

Example No. 2-92: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.82 (br s, 1H); 7.81 (d, 1H);

7.36 (d, 1H); 7.29 (t, 1H); 4.35 (q, 2H); 3.51 (t, 2H); 3.22 (s, 3H); 1.86 (t, 3H); 1.46 (t, 3H); 0.69 (m, 4H);

Example no. 2-94: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.73 (br s, 1H); 9.09 (s, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.26 (t, 1H); 4.49 (d, 2H); 4.35 (q, 2H); 1.46 (t, 3H); 0.94 (m, 2H); 0.83 (m, 2H);

Example no. 2-95: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.50 (br s, 1H); 7.85 (d, 1H); 7.39 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.31 (s, 3H); 1.46 (t, 3H); 1.05 (m, 2H); 0.87 (m, 2H); Example no. 2-96: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.73 (br s, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.65 (q, 2H); 1.46 (t, 3H); 1.10 (t, 3H); 1.04 (m, 2H); 0.87 (m, 2H);

Example no. 2-97: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.28 (s, 1H); 7.85 (d, 1H); 7.39 (d, 1H); 7.29 (t, 1H); 4.35 (q, 2H); 4.11 (q, 2H); 1.46 (m, 5H); 1.20 (t, 3H); 1.11 (m, 2H);

Example no. 2-98: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.71 (br s, 1H); 8.99 (s, 1H); 7.81 (d, 1H); 7.33 (d, 1H); 7.19 (t, 1H); 4.34 (q, 2H); 4.06 (q, 2H); 2.73 (s, 2H); 1.45 (t, 3H); 1.18 (t, 3H); 0.80 (m, 2H); 0.77 (m, 2H);

Example no. 2-99: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.76 (br s, 1H); 9.65 (s, 1H); 7.89 (d, 1H); 7.43 (d, 1H); 7.34 (t, 1H); 4.35 (q, 2H); 1.63 (m, 2H); 1.46 (t, 3H); 1.20 (m, 2H);

Example no. 2-100: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.73 (br s, 1H); 9.22 (br s, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.28 (t, 1H); 4.34 (q, 2H); 3.04 (s, 1H); 1.46 (t, 3H); 1.19 (m, 2H); 1.04 (m, 2H);

Example no. 2-101: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.75 (br s, 1H); 9.37 (s, 1H); 7.86 (d, 1H); 7.42 (d, 1H); 7.40 (t, 1H); 7.30 (m, 3H); 7.19 (m, 2H); 4.36 (q, 2H); 1.47 (t, 3H); 1.29 (m, 4H);

Example no. 2-102: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.68 (br s, 1H); 9.31 (br s, 1H); 7.79 (d, 1H); 7.70 (m, 1H); 7.41 (m, 1H); 7.31 (m, 3H); 7.15 (t, 1H); 4.32 (q, 2H); 1.44 (t, 3H); 1.19 (m, 2H); 1.16 (m, 2H);

Example no. 2-103: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.76 (br s, 1H); 9.44 (br s, 1H); 7.87 (d, 1H); 7.43 (d, 1H); 7.40 (m, 2H); 7.31 (d, 1H); 7.21 (m, 3H); 4.36 (q, 2H); 1.47 (t, 3H); 1.36 (m, 2H); 1.30 (m, 2H);

Example no. 2-104: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.41 (s, 1H); 7.85 (d, 1H); 7.48 (m, 1H); 7.40 (d, 1H); 7.36 (t, 1H); 6.39 (m, 1H); 6.31 (m, 1H); 4.35 (q, 2H); 1.47 (t, 3H); 1.32 (m, 2H); 1.17 (m, 2H);

Example no. 2-105: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.30 (br s, 1H); 7.84 (d, 1H); 7.56 (m, 1H); 7.49 (s, 1H); 7.40 (d, 1H); 7.37 (t, 1H); 6.33 (m, 1H); 4.35 (q, 2H); 1.47 (t, 3H); 1.14 (m, 2H); 1.12 (m, 2H);

Example no. 2-107: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.09 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

Example no. 2-108: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.09 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

Example no. 2-110: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 9.06 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.10 (d, 2H); 2.55 (q, 2H); 1.47 (t, 3H); 0.96 (t, 3H); Example no. 2-111: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.74 (br s, 1H); 8.92 (t, 1H); 7.84 (d, 1H); 7.68 (br t, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 4.35 (q, 2H); 3.88 (d, 2H); 3.14 (m, 2H); 1.46 (t, 3H); 1.04 (t, 3H);

Example no. 2-112: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.73 (br s, 1H); 8.88 (t, 1H); 7.87 (m, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.36 (q, 2H); 3.85 (d, 2H); 2.65 (m, 1H); 1.46 (t, 3H); 0.65 (m, 2H); 0.41 (m, 2H);

Example no. 2-113: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.76 (br s, 1H); 7.86 (d, 1H); 7.46 (d, 1H); 7.42 (t, 1H); 4.36 (q, 2H); 3.04 (s, 3H); 2.81 (s, 3H); 1.47 (t, 3H);

Example No. 2-114: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.76 (br s, 1H); 7.86 (d, 1H); 7.44 (m, 2H);

4.36 (q, 2H); 3.52 and 3.13 (2x m, 2H); 3-01 and 2.78 (2x, 3H); 1.47 (t, 3H); 1.14 and 1.06 (2x t, 3H);

Example no. 2-115: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.76 (br s, 1H); 7.85 (d, 1H); 7.46 (t, 1H); 7.43 (m, 1H); 7.36 (q, 2H); 3.00 and 2.71 (2s, 3H); 2.90 and 2.62 (2x m, 1H); 1.47 (t, 3H); 0.83-0.46 (m, 4H);

Example no. 2-125: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.79 (br s, 1H); 8.97 (br s, 1H); 7.88 (d, 1H); 7.60 (br d, 1H); 4.36 (q, 2H); 2.58 (m, 1H); 1.88-1.62 (m, 6H); 1.46 (t, 3H); 0.68 (m, 4H);

Example No. 2-126: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.72 (br s, 1H); 8.83 (br s, 1H); 7.81 (d, 1H);

7.36 (d, 1H); 7.28 (t, 1H); 4.35 (q, 2H); 2.57 (m, 1H); 1.87-1.63 (m, 6H); 1.46 (t, 3H); 0.67 (m, 4H);

Example no. 2-127: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.50 (br s, 1H); 8.44 (q, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.36 (q, 2H); 2.80 (d, 3H); 2.14 (m, 1H); 1.48 (t, 3H); 0.83 (m, 2H); 0.60 (m, 2H);

Example no. 2-128: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.50 (br s, 1H); 8.52 (t, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.37 (q, 2H); 3.29 (m, 2H); 2.17 (m, 1H); 1.48 (t, 3H); 1.13 (t, 3H); 0.83 (m, 2H); 0.63 (m, 2H);

Example no. 2-129: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.50 (br s, 1H); 8.59 (d, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.36 (q, 2H); 2.80 (m, 1H); 2.15 (m, 1H); 1.48 (t, 3H); 0.84 (m, 2H); 0.71 (m, 2H); 0.62 (m, 2H); 0.51 (m, 2H);

Example no. 2-130: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.42 (br s, 1H); 8.33 (br q, 1H); 7.62 (d, 1H); 7.24 (d, 1); 7.20 (t, 1H); 4.36 (q, 2H); 2.78 (d, 3H); 1.48 (t, 3H); 0.81 (2H); 0.58 (m, 2H);

Example no. 2-131: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.42 (br s, 1H); 8.40 (t, 1H); 7.61 (d, 1H); 7.23 (d, 1H); 7.18 (t, 1H); 4.36 (q, 2H); 3.28 (m, 2H); 2.14 (m, 2H); 1.48 (t, 3H); 1.12 (t, 3H); 0.82 (m, 2H); 0.60 (m, 2H);

Example no. 2-132: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.42 (br s, 1H); 8.47 (d, 1H); 7.61 (d, 1H); 7.22 (d, 1H); 7.18 (t, 1H); 4.35 (q, 2H); 2.80 (m, 1H); 2.13 (m, 1H); 1.47 (s, 3H); 0.82 (m, 2H); 0.70 (m, 2H); 0.59 (m, 2H); 0.51 (m, 2H); Example No. 2-133: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.59 (br s, 1H); 8.35 (br q, 1H); 7.74 (d, 1H);

7.29 (d, 1H); 6.34 (it, 1H); 4.45 (td, 2H); 4.34 (q, 2H); 2.75 (d, 3H); 1.46 (t, 3H);

Example no. 2-134: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.58 (br s, 1H); 8.42 (br t, 1H); 7.74 (d, 1H); 7.28 (d, 1H); 6.34 (dd, 1H); 4.44 (td, 2H); 4.34 (q, 2H); 3.25 (m, 2H); 1.46 (t, 3H); 1.10 (t, 3H);

Example no. 2-135: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 11.60 (br s, 1H); 8.49 (d, 1H); 7.74 (d, 1H); 7.27 (d, 1H); 6.34 (dd, 1H); 4.42 (td, 2H); 4.33 (q, 2H); 2.76 (m, 1H); 1.46 (t, 3H); 0.69 (m, 2H); 0.49 (m, 2H);

Example no. 3-1: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.49 (br q, 1H); 7.89 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 2.77 (d, 3H); 2.39 (s, 3H);

Example no. 3-2: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.57 (br t, 1H); 7.89 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 3.27 (m, 2H); 2.41 (s, 3H); 1.10 (t, 3H);

Example no. 3-6: ¹ H NMR (400 MHz, CDC ₁₃ ): δ = 7.91 (d, 1H); 7.16 (br d, 1H); 5.83 (br s, 1H); 3.90 (s, 3H); 2.92 (m, 1H); 2.57 (s, 3H); 0.90 (m, 2H); 0.64 (m, 2H);

Example no. 3-10: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.49 (m, 1H); 7.88 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 2.80 (q, 2H); 2.77 (d, 3H); 1.12 (t, 3H);

Example no. 3-11: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.58 (br t, 1H); 7.88 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 3.27 (m, 2H); 2.83 (q, 2H); 1.13 (t, 3H); 1.09 (t, 3H);

Example no. 3-15: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.62 (br d, 1H); 7.87 (d, 1H); 7.36 (br d, 1H); 3.85 (s, 3H); 2.81 (m, 3H); 1.12 (t, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

Example No. 3-19: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.66 (br q, 1H); 7.94 (d, 1H); 7.56 (d, 1H); 3.89 (s, 3H); 2.78 (d, 3H);

Example no. 3-20: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.73 (br t, 1H); 7.93 (d, 1H); 7.56 (d, 1H); 3.89 (s, 3H); 3.27 (m, 2H); 1.10 (t, 3H);

Example No. 3-22: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.61 (br d, 1H); 7.92 (d, 1H); 7.55 (br d, 1H); 4.05 (m, 1H); 3.89 (s, 3H); 1.13 (d, 6H);

Example no. 3-23: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.80 (br t, 1H); 7.93 (d, 1H); 7.56 (br d, 1H); 3.89 (s, 3H); 3.15 (m, 2H); 0.98 (m, 1H); 0.43 (m, 2H); 0.23 (m, 2H);

Example no. 3-24: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.78 (d, 1H); 7.93 (d, 1H); 7.56 (d, 1H); 3.88 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.48 (m, 2H);

Example no. 3-25: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.92 (s, 1H); 7.92 (d, 1H); 7.54 (d, 1H); 3.89 (s, 3H); 1.38 (s, 3H); 0.69 (m, 2H); 0.63 (m, 2H); Example no. 3-26: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.87 (br s, 1H); 7.92 (d, 1H); 7.54 (br d, 1H); 3.88 (s, 3H); 1.61 (q, 2H); 0.95 (t, 3H); 0.66 (m, 2H); 0.63 (m, 2H);

Example no. 3-27: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.87 (br s, 1H); 7.91 (d, 1H); 7.54 (br d, 1H); 3.88 (s, 3H); 1.47 (m, 2H); 1.48 (m, 2H); 0.89 (t, 3H); 0.67 (m, 2H); 0.62 (m, 2H);

Example no. 3-29: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.01 (br s, 1H); 7.92 (d, 1H); 7.53 (br s, 1H); 3.88 (s, 3H); 3.52 (s, 2H); 3.47 (q, 2H); 1.11 (t, 3H); 0.78 (m, 2H); 0.70 (m, 2H);

Example no. 3-31: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.72 (br t, 1H); 7.93 (d, 1H); 7.56 (m, 1H); 3.89 (s, 3H); 3.21 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

Example no. 3-32: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.17 (br s, 1H); 7.94 (d, 1H); 7.56 (br d, 1H); 4.48 (d, 2H); 3.89 (s, 3H); 0.94 (m, 2H); 0.82 (m, 2H);

Example no. 3-35: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.35 (br s, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.11 (q, 2H); 3.89 (s, 3H); 1.47 (m, 2H); 1.18 (t, 3H); 1.09 (m, 2H);

Example no. 3-37: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 14.84 (br s, 1H); 9.74 (s, 1H); 7.97 (d, 1H); 7.57 (br d, 1H); 3.08 (s, 1H); 1.63 (m, 2H); 1.18 (m, 2H);

Example no. 3-38: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.32 (br s, 1H); 7.94 (d, 1H); 7.56 (br d, 1H); 3.88 (s, 3H); 3.05 (s, 1H); 1.20 (m, 2H); 1.02 (m, 2H);

Example no. 3-42: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.48 (br s, 1H); 7.96 (d, 1H); 7.58 (br d, 1H); 7.48M, 1H); 6.39 (m, 1H); 6.24 (m, 1H); 3.89 (s, 3H); 1.31 (m, 2H); 1.15 (m, 2H);

Example no. 3-45: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.12 (br t, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.11 (d, 1H); 3.89 (s, 3H); 2.14 (s, 3H);

Example no. 3-46: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.11 (br t, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.12 (d, 2H); 3.89 (s, 3H); 2.52 (m, 2H); 0.96 (t, 3H);

Example no. 3-48: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.00 (br t, 1H); 7.94 (d, 1H); 7.75 (br m, 1H); 7.55 (br d, 1H); 3.89 (s, 3H); 3.87 (d, 2H); 2.63 (d, 3H);

Example no. 3-49: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.99 (br t, 1H); 7.94 (d, 1H); 7.78 (br r, 1H); 7.55 (br d, 1H); 3.89 (s, 3H); 3.87 (d, 2H); 3.12 (m, 2H); 1.03 (t, 3H);

Example no. 3-50: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.96 (br t, 1H); 7.94 (br s, 1H); 7.93 (d, 1H); 7.54 (br d, 1H); 3.89 (s, 3H); 3.84 (d, 2H); 2.64 (m, 1H); 0.64 (m, 2H); 0.40 (m, 2H);

Example No. 3-51: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.00 (d, 1H); 7.62 (d, 1H); 3.89 (s, 3H); 3.03 (s, 3H); 2.73 (s, 3H); Example no. 3-52: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.99 (d, 1H); 7.62 (br d, 1H); 3.89 (s, 3H); 3.60, 3.43 and 3.09 (3x m, 2H); 3.01 and 2.76 (2x s, 3H); 1.13 and 1.04 (2x t, 3H);

Example no. 3-53: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.00 (m, 1H); 7.61 (m, 1H); 3.89 (s, 3H); 3.00 and 2.69 (2x s, 3H); 2.48 and 2.59 (2x m, 1H); 0.83 and 0.70 and 0.60 and 0.48 (4x m, 4H);

Example no. 3-63: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.38 (br q, 1H); 7.86 (d, 1H); 7.25 (t, 1H); 7.17 (br d, 1H); 3.83 (s, 3H); 2.76 (d, 3H); 2.38 (s, 3H);

Example no. 3-64: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.45 (br, t, 1H); 7.86 (d, 1H); 7.23 (t, 1H); 7.17 (d, 1H); 3.83 (s, 3H); 3.26 (m, 2H); 2.40 (s, 3H); 1.10 (t, 3H);

Example no. 3-68: ¹ H NMR (400 MHz, CDC ₁₃ ): δ = 7.89 (d, 1H); 7.04 (br d, 1H); 6.55 (t, 1H); 5.85 (br s, 1H); 3.89 (s, 3H); 2.92 (m, 1H); 2.55 (s, 3H); 0.88 (m, 4H);

Example no. 3-72: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.38 (m, 1H); 7.85 (d, 1H); 7.26 (t, 1H); 7.17 (d, 1H); 3.84 (s, 3H); 2.80 (q, 2H); 2.76 (d, 3H); 1.11 (t, 3H);

Example no. 3-73: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.45 (br t, 1H); 7.85 (d, 1H); 7.23 (t, 1H); 7.17 (d, 1H); 3.84 (s, 3H); 3.27 (m, 2H); 2.82 (q, 2H); 1.12 (t, 3H); 1.09 (t, 3H);

Example no. 3-77: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.50 (br d, 1H); 7.85 (d, 1H); 7.23 (t, 1H); 7.16 (d, 1H); 3.83 (s, 3H); 2.80 (m, 3H); 1.11 (t, 3H); 0.70 (m, 2H); 0.47 (m, 2H);

Example no. 3-81: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.53 (br q, 1H); 7.90 (d, 1H); 7.34 (d, 1H); 7.33 (t, 1H); 3.87 (s, 3H); 2.77 (d, 3H);

Example no. 3-82: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.59 (br t, 1H); 7.89 (d, 1H); 7.34 (d, 1H); 7.31 (t, 1H); 3.87 (s, 3H); 3.26 (m, 2H); 1.10 (t, 3H);

Example no. 3-83: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.58 (br t, 1H); 7.89 (d, 1H); 7.34 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 3.19 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

Example no. 3-84: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.47 (d, 1H); 7.88 (d, 1H); 7.32 (d, 1H); 7.28 (t, 1H); 4.02 (m, 1H); 3.87 (s, 3H); 1.13 (d, 6H);

Example no. 3-86: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.64 (br d, 1H); 7.89 (d, 1H); 7.33 (d, 1H); 7.31 (t, 1H); 3.86 (s, 3H); 2.79 (m, 1H); 0.71 (m, 2H); 0.48 (m, 2H);

Example no. 3-87: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.77 (s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.26 (t, 1H); 3.86 (s, 3H); 1.38 (s, 3H); 0.70 (m, 2H); 0.60 (m, 2H);

Example no. 3-88: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.73 (br s, 1H); 7.88 (d, 1H); 7.31 (d, 1H); 7.28 (t, 1H); 3.86 (s, 3H); 1.61 (q, 2H); 0.96 (t, 3H); 0.67 (m, 2H); 0.60 (m, 2H); Example No. 3-89: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.73 (br s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.28

(t, 1H); 3.86 (s, 3H); 1.56 (m, 2H); 1.48 (m, 2H); 0.89 (t, 3H); 0.68 (m, 2H); 0.60 (m, 2H);

Example No. 3-90: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.73 (br s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.28

(t, 1H); 3.86 (s, 3H); 1.95 (m, 1H); 1.49 (d, 2H); 0.92 (d, 6H); 0.71 (m, 2H); 0.59 (m, 2H);

Example no. 3-91: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.88 (br s, 1H); 7.88 (d, 1H); 7.30 (br d, 1H); 7.25 (t, 1H); 3.86 (s, 3H); 3.52 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.76 (m, 2H); 0.71 (m, 2H);

Example no. 3-92: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.77 (br s, 1H); 7.88 (d, 1H); 7.31 (d, 1H); 7.30 (t, 1H); 3.86 (s, 3H); 3.50 (t, 2H); 3.22 (s, 3H); 1.85 (t, 3H); 0.67 (m, 4H);

Example no. 3-94: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.03 (br s, 1H); 7.90 (d, 1H); 7.33 (d, 1H); 7.27 (t, 1H); 4.48 (d, 2H); 3.86 (s, 3H); 0.93 (m, 2H); 0.83 (m, 2H);

Example no. 3-95: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.45 (br s, 1H); 7.91 (d, 1H); 7.35 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 3.30 (s, 3H); 1.04 (m, 2H); 0.86 (m, 2H);

Example no. 3-96: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.44 (br s, 1H); 7.91 (d, 1H); 7.34 (d, 1H); 7.32 (t, 1H); 3.86 (s, 3H); 3.63 (q, 2H); 1.09 (t, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

Example no. 3-97: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.22 (br s, 1H); 7.91 (d, 1H); 7.34 (d, 1H); 7.30 (t, 1H); 4.10 (q, 2H); 3.87 (s, 3H); 1.44 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

Example no. 3-98: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.93 (br s, 1H); 7.87 (d, 1H); 7.29 (d, 1H); 7.20 (t, 1H); 4.05 (q, 2H); 3.86 (s, 3H); 2.72 (s, 2H); 1.19 (t, 3H); 0.78 (m, 2H); 0.76 (m, 2H);

Example no. 3-99: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.59 (s, 1H); 7.96 (d, 1H); 7.38 (d, 1H); 7.34 (t, 1H); 3.87 (s, 3H); 1.61 (m, 2H); 1.19 (m, 2H);

Example no. 3-100: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.17 (br s, 1H); 7.90 (d, 1H); 7.33 (d, 1H); 7.29 (t, 1H); 3.86 (s, 3H); 3.03 (s, 1H); 1.18 (m, 2H); 1.03 (m, 2H);

Example no. 3-101: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.31 (br s, 1H); 7.93 (d, 1H); 7.41 (t, 1H); 7.37 (d, 1H); 7.31-7.12 (m, 5H); 3.87 (s, 3H); 0.95 (m, 2H); 0.89 (m, 2H);

Example no. 3-102: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.25 (br s, 1H); 7.86 (d, 1H); 7.69 (m, 1H); 7.40 (m, 1H); 7.27 (m, 2H); 7.26 (d, 1H); 7.16 (t, 1H); 3.84 (s, 3H); 1.16 (m, 4H);

Example no. 3-103: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.38 (br s, 1H); 7.94 (d, 1H); 7.39 (m, 2H); 7.37 (t, 1H); 7.30 (d, 1H); 7.25 (m, 1H); 7.22 (m, 1H); 3.88 (s, 3H); 1.32 (m, 4H);

Example no. 3-104: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.35 (br s, 1H); 7.92 (d, 1H); 7.48 (m, 1H); 7.37 (t, 1H); 7.36 (d, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 3.87 (s, 3H); 1.31 (m, 2H); 1.16 (m, 2H); Example no. 3-105: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.24 (br s, 1H); 7.91 (d, 1H); 7.56 (m, 1H); 7.48 (m, 1H); 7.38 (t, 1H); 7.35 (d, 1H); 6.32 (m, 1H); 3.87 (s, 3H); 1.13 (m, 2H); 1.11 (m, 2H);

Example no. 3-107: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.05 (br t, 1H); 7.92 (d, 1H); 7.35 (d, 1H); 7.34 (t, 1H); 4.07 (d, 2H); 3.88 (s, 3H); 2.15 (s, 3H);

Example no. 3-108: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.03 (br t, 1H); 7.92 (d, 1H); 7.35 (d, 1H); 7.34 (t, 1H); 4.09 (d, 2H); 3.87 (s, 3H); 2.54 (m, 2H); 0.95 (t, 3H);

Example No. 3-110: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.90 (br t, 1H); 7.91 (d, 1H); 7.62 (br q, 1H);

7.33 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 2.64 (d, 2H);

Example No. 3-111: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.90 (br t, 1H); 7.91 (d, 1H); 7.64 (br t, 1H);

7.34 (d, 1H); 7.33 (t, 1H); 3.87 (s, 3H); 3.87 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

Example no. 3-112: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.84 (br t, 1H); 7.90 (d, 1H); 7.84 (br d, 1H); 7.33 (d, 1H); 7.30 (t, 1H); 3.87 (s, 3H); 3.83 (d, 2H); 2.65 (m, 1H); 0.64 (m, 2H); 0.41 (m, 2H);

Example no. 3-113: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.95 (d, 1H); 7.42 (t, 1H); 7.41 (d, 1H); 3.78 (s, 3H); 3.02 (s, 3H); 2.77 (s, 3H);

Example no. 3-114: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.94 (d, 1H); 7.45 and 7.42 (2x d, 1H); 7.40 (d, 1H); 3.87 (s, 3H); 3.51 and 3.08 (2x m, 2H); 3.32 and 2.74 (2x s, 3H); 1.13 and 1.03 (2x t, 3H);

Example no. 3-115: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 7.95 (d, 1H); 7.47 (t, 1H); 7.39 (d, 1H); 3.87 (s, 3H); 2.98 and 2.67 (2x s, 3H); 2.89 and 2.58 (2x m, 1H); 0.81 and 0.72 and 0.57 and 0.45 (4x m, 4H);

Example no. 3-125: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.91 (br s, 1H); 7.92 (d, 1H); 7.55 (br d, 1H); 3.88 (s, 3H); 2.55 (m, 1H); 1.80 (m, 5H); 1.63 (m, 1H); 0.67 (m, 4H);

Example no. 3-126: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.77 (br s, 1H); 7.88 (d, 1H); 7.32 (d, 1H); 7.29 (t, 1H); 3.86 (s, 3H); 2.56 (m, 1H); 1.62-1.88 (m, 6H); 0.66 (m, 4H);

Example no. 3-127: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.44 (br q, 1H); 7.65 (d, 1H); 7.38 (br d, 1H); 3.87 (s, 3H); 2.78 (d, 3H); 2.09 (m, 1H); 0.82 (m, 2H); 0.45 (m, 2H);

Example no. 3-128: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.49 (br t, 1H); 7.64 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 3.28 (m, 2H); 2.10 (m, 1H); 1.11 (t, 3H); 0.82 (m, 2H); 0.47 (m, 2H);

Example no. 3-129: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.57 (br d, 1H); 7.64 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 2.79 (m, 1H); 2.08 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.48 (m, 4H);

Example no. 3-130: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.32 (br d, 1H); 7.60 (d, 1H); 7.19 (t, 1H); 7.18 (d, 1H); 3.84 (s, 3H); 2.77 (d, 3H); 2.09 (m, 1H); 0.79 (m, 2H); 0.42 (m, 2H); Example no. 3-131: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.39 (br t, 1H); 7.59 (d, 1H); 7.17 (t, 1H); 7.17 (d, 1H); 3.85 (s, 3H); 3.28 (m, 2H); 2.10 (m, 1H); 1.10 (t, 3H); 0.80 (m, 2H); 0.46 (m, 2H);

Example no. 3-132: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.44 (br d, 1H); 7.59 (d, 1H); 7.16 (t, 1H); 7.16 (d, 1H); 3.84 (s, 3H); 2.79 (m, 1H); 2.05 (m, 1H); 0.79 (m, 2H); 0.68 (m, 2H); 0.50 (m, 2H); 0.43 (m, 2H);

Example No. 3-133: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.32 (br s, 1H); 7.84 (br d, 1H); 7.25 (br d, 1H);

6.32 (br t, 1H); 4.43 (br t, 2H); 3.83 (s, 3H); 2.73 (br d, 3H);

Example no. 3-134: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.39 (br t, 1H); 7.84 (d, 1H); 7.23 (d, 1H); 6.32 (dd, 1H); 4.43 (td, 2H); 3.83 (s, 3H); 3.23 (m, 2H); 1.08 (t, 3H);

Example no. 3-135: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.45 (br d, 1H); 7.84 (d, 1H); 7.22 (d, 1H); 6.32 (dd, 1H); 4.42 (td, 2H); 3.83 (s, 3H); 2.74 (m, 1H); 0.66 (m, 2H); 0.48 (m, 2H);

Example no. 4-1: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.25 (br s, 1H); 8.47 (q, 1H); 7.89 (d, 1H); 7.33 (br d, 1H); 2.77 (d, 3H); 2.41 (s, 3H);

Example no. 4-2: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.23 (br s, 1H); 8.55 (t, 1H); 7.89 (d, 1H); 7.33 (br d, 1H); 3.27 (m, 2H); 2.43 (s, 3H); 1.10 (t, 3H);

Example no. 4-6: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.25 (br s, 1H); 8.61 (d, 1H); 7.89 (d, 1H); 7.32 (br d, 1H); 2.81 (m, 1H); 2.41 (s, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

Example no. 4-10: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.27 (br s, 1H); 8.47 (br q, 1H); 7.88 (d, 1H); 7.34 (br d, 1H); 2.85 (q, 2H); 2.77 (d, 3H); 1.13 (t, 3H);

Example no. 4-11: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.27 (br s, 1H); 8.56 (br t, 1H); 7.88 (br d, 1H); 7.34 (br d, 1H); 3.27 (m, 2H); 2.87 (q, 2H); 1.14 (t, 3H); 1.09 (t, 3H);

Example No. 4-15: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.26 (br s, 1H); 8.60 (br d, 1H); 7.88 (d, 1H);

7.32 (br d, 1H); 2.86 (q, 2H); 2.80 (m, 1H); 1.13 (t, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

Example no. 4-19: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.75 (br s, 1H); 8.63 (m, 1H); 7.91 (d, 1H); 7.51 (m, 2H); 2.78 (d, 3H);

Example no. 4-20: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.74 (br s, 1H); 8.71 (br t, 1H); 7.90 (d, 1H); 7.51 (d, 1H); 3.27 (m, 2H); 1.10 (t, 3H);

Example no. 4-21: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.73 (br s, 1H); 8.70 (t, 1H); 7.90 (d, 1H); 7.51 (m, 1H); 3.21 (m, 2H); 1.50 (m, 2H); 0.91 (t, 3H);

Example No. 4-22: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.71 (br s, 1H); 7.89 (d, 1H); 7.50 (m, 1H); 4.05 (m, 1H); 1.13 (d, 6H); Example no. 4-23: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.76 (br s, 1H); 8.78 (t, 1H); 7.90 (d, 1H); 7.51 (m, 1H); 3.15 (m, 2H); 0.98 (m, 1H); 0.43 (m, 2H); 0.23 (m, 2H);

Example no. 4-24: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.75 (br s, 1H); 8.75 (d, 1H); 7.90 (d, 1H); 7.50 (m, 1H); 2.80 (m, 1H); 0.72 (m, 2H); 0.47 (m, 2H);

Example no. 4-25: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.76 (br s, 1H); 8.90 (s, 1H); 7.88 (d, 1H); 7.48 (m, 1H); 1.38 (s, 3H); 0.68 (m, 2H); 0.62 (m, 2H);

Example no. 4-26: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.83 (br s, 1H); 7.77 (d, 1H); 7.43 (br d, 1H); 1.61 (q, 2H); 0.95 (t, 3H); 0.66 (m, 2H); 0.62 (m, 2H);

Example No. 4-27: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.73 (br s, 1H); 8.85 (br s, 1H); 7.88 (d, 1H);

7.49 (br, d, 1H); 1.56 (m, 2H); 1.47 (m, 2H); 0.89 (t, 3H); 0.67 (m, 2H); 0.62 (m, 2H);

Example no. 4-29: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.73 (br s, 1H); 8.99 (br s, 1H); 7.88 (d, 1H); 7.48 (br d, 1H); 3.52 (s, 2H); 3.47 (q, 2H); 1.11 (t, 3H); 0.77 (m, 2H); 0.70 (m, 2H);

Example No. 4-32: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.76 (br s, 1H); 9.15 (br s, 1H); 7.90 (d, 1H);

7.50 (br d, 1H); 4.48 (d, 2H); 0.94 (m, 2H); 0.81 (m, 2H);

Example no. 4-35: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.79 (br s, 1H); 7.92 (d, 1H); 7.53 (br d, 1H); 4.11 (q, 2H); 1.46 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

Example no. 4-37: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 9.76 (s, 1H); 8.00 (d, 1H); 7.61 (br d, 1H); 3.89 (s, 3H); 1.64 (m, 2H); 1.19 (m, 2H);

Example No. 4-38: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.77 (br s, 1H); 9.29 (br s, 1H); 7.91 (d, 1H);

7.51 (br s, 1H); 3.04 (s, 1H); 1.19 (m, 2H); 1.02 (m, 2H);

Example no. 4-42: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.78 (br s, 1H); 9.46 (br s, 1H); 7.92 (d, 1H); 7.54 (br d, 1H); 7.48 (m, 1H); 6.39 (m, 1H); 6.24 (m, 1H); 1.32 (m, 2H); 1.16 (m, 2H);

Example no. 4-45: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.79 (br s, 1H); 9.10 (t, 1H); 7.92 (d, 1H); 7.53 (m, 1H); 4.10 (d, 2H); 2.14 (s, 3H);

Example no. 4-46: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.78 (br s, 1H); 9.10 (t, 1H); 7.92 (d, 1H); 7.53 (m, 1H); 4.11 (d, 2H); 2.54 (q, 2H); 0.96 (t, 3H);

Example no. 4-48: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.80 (br s, 1H); 8.98 (t, 1H); 7.91 (d, 1H); 7.73 (br q, 1H); 7.50 (m, 1H); 3.87 (d, 2H); 2.63 (d, 3H);

Example no. 4-49: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.90 (br s, 1H); 8.97 (t, 1H); 7.91 (d, 1H); 7.75 (t, 1H); 7.50 (m, 1H); 3.86 (d, 2H); 3.12 (m, 2H); 1.03 (t, 3H); Example no. 4-50: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.94 (t, 1H); 7.91 (m, 1H); 7.90 (d, 1H); 7.50 (m, 1H); 3.83 (d, 2H); 2.64 (m, 1H); 0.64 (m, 2H); 0.40 (m, 2H);

Example No. 4-51: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.80 (br s, 1H); 7.96 (d, 1H); 7.58 (m, 1H); 3.03 (s, 3H); 2.78 (s, 3H);

Example no. 4-52: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.85 (br s, 1H); 7.96 (m, 1H); 7.57 (m, 1H); 3.61, 3.42, 3.09 (3x m, 2H); 3.00, 2.76 (2x s, 3H); 1.17, 1.15 (2x t, 3H);

Example no. 4-53: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.80 (br s, 1H); 7.96 (m, 1H); 7.57 (m, 1H); 3.00, 2.69 (2x s, 3H); 2.89, 2.59 (2x m, 1H); 0.82, 071, 0.61, 0.48 (4xm, 4H);

Example no. 4-63: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.04 (br s, 1H); 8.36 (q, 1H); 7.86 (d, 1H); 7.22 (t, 1H); 7.14 (d, 1H); 2.75 (d, 3H); 2.39 (s, 3H);

Example no. 4-64: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.04 (br s, 1H); 8.42 (t, 1H); 7.86 (d, 1H); 7.21 (t, 1H); 7.13 (d, 1H); 3.25 (m, 2H); 2.41 (s, 3H); 1.09 (t, 3H);

Example No. 4-68: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.04 (br s, 1H); 8.48 (br d, 1H); 7.86 (d, 1H);

7.20 (t, 1H); 7.13 (d, 1H); 2.80 (m, 1H); 2.40 (s, 3H); 0.69 (m, 2H); 0.47 (m, 2H);

Example no. 4-72: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.07 (br q, 1H); 8.36 (br q, 1H); 7.86 (d, 1H); 7.23 (t, 1H); 7.14 (d, 1H); 2.85 (q, 2H); 2.76 (d, 3H); 1.11 (t, 3H);

Example No. 4-73: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.02 (br s, 1H); 8.43 (br t, 1H); 7.86 (d, 1H);

7.21 (t, 1H); 7.13 (d, 1H); 3.26 (m, 2H); 2.88 (q, 2H); 1.13 (t, 3H); 1.09 (t, 3H);

Example no. 4-77: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.04 (br s, 1H); 8.48 (br d, 1H); 7.85 (d, 1H); 7.20 (t, 1H); 7.12 (d, 1H); 2.83 (q, 2H); 2.80 (m, 1H); 1.12 (t, 3H); 0.69 (m, 2H); 0.47 (m, 2H);

Example no. 4-81: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.50 (br s, 1H); 8.51 (q, 1H); 7.87 (d, 1H); 7.30 (d, 1H); 7.30 (t, 1H); 2.76 (d, 2H);

Example no. 4-82: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.55 (br s, 1H); 8.56 (t, 1H); 7.87 (d, 1H); 7.30 (d, 1H); 7.28 (t, 1H); 3.25 (m, 2H); 1.10 (t, 3H);

Example no. 4-83: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 12.80 (br s, 1H); 8.56 (t, 1H); 7.86 (d, 1H); 7.30 (d, 1H); 7.29 (t, 1H); 3.19 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

Example no. 4-84: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 12.50 (br s, 1H); 8.45 (d, 1H); 7.86 (d, 1H); 7.29 (d, 1H); 7.25 (t, 1H); 4.04 (m, 1H); 1.13 (d, 6H);

Example no. 4-86: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.51 (br s, 1H); 8.62 (d, 1H); 7.86 (d, 1H); 7.29 (d, 1H); 7.27 (t, 1H); 2.79 (m, 1H); 0.70 (m, 2H); 0.48 (m, 2H); Example no. 4-87: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.40 (br s, 1H); 8.75 (s, 1H); 7.85 (d, 1H); 7.27 (d, 1H); 7.23 (t, 1H); 1.38 (s, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

Example no. 4-88: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.40 (br s, 1H); 8.75 (s, 1H); 7.85 (d, 1H); 7.27 (d, 1H); 7.23 (t, 1H); 1.38 (s, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

Example No. 4-89: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.55 (br s, 1H); 8.71 (br s, 1H); 7.85 (d, 1H);

7.27 (d, 1); 7.25 (t, 1H); 1.61 (q, 2H); 0.96 (t, 3H); 0.68 (m, 2H); 0.60 (m, 2H);

Example No. 4-90: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.52 (br s, 1H); 8.71 (br s, 1H); 7.85 (d, 1H);

7.27 (d, 1H); 7.25 (t, 1H); 1.96 (m, 1H); 1.49 (d, 2H); 0.92 (d, 6H); 0.71 (m, 2H); 0.59 (m, 2H);

Example no. 4-91: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.52 (br s, 1H); 8.86 (s, 1H); 7.85 (d, 1H); 7.26 (d, 1H); 7.22 (t, 1H); 3.52 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.76 (m, 2H); 0.71 (m, 2H);

Example No. 4-92: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.54 (br s, 1H); 8.74 (br s, 1H); 7.85 (d, 1H);

7.27 (d, 1H); 7.26 (t, 1H); 3.50 (t, 2H); 3.22 (s, 3H); 1.85 (t, 2H); 0.66 (m, 4H);

Example No. 4-94: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.55 (br s, 1H); 9.01 (br s, 1H); 7.87 (d, 1H);

7.29 (d, 1H); 7.24 (t, 1H); 4.48 (d, 2H); 0.92 (m, 2H); 0.83 (m, 2H);

Example No. 4-95: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.65 (br s, 1H); 9.42 (br s, 1H); 7.86 (d, 1H);

7.30 (d, 1H); 7.28 (t, 1H); 3.30 (s, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

Example No. 4-96: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.58 (br s, 1H); 9.42 (br s, 1H); 7.88 (d, 1H);

7.30 (d, 1H); 7.29 (t, 1H); 3.63 (q, 2H); 1.09 (t, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

Example no. 4-97: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.55 (br s, 1H); 9.20 (s, 1H); 7.88 (d, 1H); 7.30 (d, 1H); 7.27 (t, 1H); 4.10 (q, 2H); 1.44 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

Example no. 4-98: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.52 (br s, 1H); 8.91 (s, 1H); 7.85 (d, 1H); 7.25 (d, 1H); 7.17 (t, 1H); 4.05 (q, 2H); 3.72 (s, 2H); 1.19 (t, 3H); 0.78 (m, 2H); 0.75 (m, 2H);

Example no. 4-99: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.61 (br s, 1H); 9.57 (s, 1H); 7.93 (d, 1H); 7.34 (d, 1H); 7.30 (t, 1H); 1.61 (m, 2H); 1.19 (m, 2H);

Example no. 4-100: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.57 (br s, 1H); 9.14 (br s, 1H); 7.88 (d, 1H); 7.29 (d, 1H); 7.26 (t, 1H); 3.02 (s, 1H); 1.18 (m, 2H); 1.03 (m, 2H);

Example no. 4-101: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.56 (br s, 1H); 9.29 (br s, 1H); 7.90 (d, 1H); 7.38 (t, 1H); 7.34 (d, 1H); 7.29 (m, 4H); 7.18 (m, 1H); 1.28 (br s, 4H);

Example No. 4-102: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.43 (br s, 1H); 9.23 (br s, 1H); 7.83 (d, 1H);

7.69 (m, 1H); 7.40 (m, 1H); 7.29 (m, 2H); 7.23 (d, 1H); 7.12 (t, 1H); 1.16 (m, 4H); Example No. 4-103: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.59 (br s, 1H); 9.36 (br s, 1H); 7.92 (d, 1H);

7.40-7.16 (m, 6H); 7.36-1.27 (m, 4H);

Example no. 4-104: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.56 (br s, 1H); 9.33 (br s, 1H); 7.89 (d, 1H); 7.48 (m, 1H); 7.34 (d, 1H); 7.31 (t, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 1.29 (m, 2H); 1.15 (m, 2H);

Example no. 4-105: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.55 (br s, 1H); 9.22 (br s, 1H); 7.88 (d, 1H); 7.56 (m, 1H); 7.47 (m, 1H); 7.35 (t, 1H); 7.33 (d, 1H); 6.32 (m, 1H); 1.13 (m, 2H); 1.09 (m, 2H);

Example No. 4-107: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.51 (br s, 1H); 9.03 (br t, 1H); 7.89 (d, 1H);

7.31 (d, 1H), 7.31 (t, 1H); 4.06 (d, 2H); 2.15 (s, 3H);

Example No. 4-108: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.50 (br s, 1H); 9.01 (br t, 1H); 7.89 (d, 1H);

7.32 (t, 1H); 7.31 (d, 1H); 4-07 (d, 2H); 2.55 (m, 2H); 0.95 (t, 3H);

Example no. 4-110: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.40 (br s, 1H); 8.89 (t, 1H); 7.88 (d, 1H); 7.60 (br q, 1H); 7.31 (d, 1H); 7.31 (t, 1H); 3.87 (d, 2H); 2.64 (d, 3H);

Example No. 4-111: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 8.88 (br t, 1H); 7.89 (d, 1H); 7.62 (br t, 1H);

7.31 (t, 1H); 7.30 (d, 1H); 3.86 (d, 2H); 3.12 (m, 2H); 1.04 (t, 3H);

Example no. 4-112: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.60 (br s, 1H); 8.83 (t, 1H); 7.88 (d, 1H); 7.82 (br d, 1H); 7.33 (d, 1H); 7.30 (t, 1H); 3.83 (d, 2H); 2.65 (m, 1H); 0.65 (m, 2H); 0.49 (m, 2H);

Example no. 4-113: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.50 (br s, 1H); 7.92 (d, 1H); 7.40 (t, 1H); 7.37 (d, 1H); 3.02 (s, 3H); 2.77 (s, 3H);

Example no. 4-114: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.40 (br s, 1H); 7.92 (d, 1H); 7.39, 7.37 (2x t, 1H); 7.35 (d, 1H); 3.50, 3.09 (2x m, 2H); 2.99, 2.74 (2x s, 3H); 117, 113 (2xt, 3H);

Example no. 4-115: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.59 (br s, 1H); 7.93 (d, 1H); 7.44 (t, 1H); 7.35 (d, 1H); 2.98 (s, 3H); 2.59 (m, 1H); 0.52-0.41 (m, 4H);

Example no. 4-125: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.74 (br s, 1H); 8.89 (br s, 1H); 7.88 (d, 1H); 7.50 (br d, 1H); 2.56 (m, 1H); 1.69-1.89 (m, 5H); 1.64 (m, 1H); 0.67 (m, 4H);

Example No. 4-126: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.52 (br s, 1H); 8.75 (br s, 1H); 7.85 (d, 1H);

7.28 (d, 1H); 7.25 (t, 1H); 2.56 (m, 1H); 1.62-1.88 (m, 6H); 0.66 (m, 4H);

Example No. 4-127: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.22 (br s, 1H); 8.42 (br q, 1H); 7.63 (d, 1H);

7.34 (br d, 1H); 2.78 (d, 3H); 2.10 (m, 1H); 0.82 (m, 2H); 0.50 (m, 2H);

Example No. 4-128: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.22 (br s, 1H); 7.62 (d, 1H); 7.34 (br d, 1H);

3.27 (m, 2H); 2.12 (m, 1H); 1.11 (t, 3H); 0.82 (m, 2H); 0.53 (m, 2H); Example No. 4-129: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.23 (br s, 1H); 8.55 (br d, 1H); 7.62 (d, 1H);

7.33 (br d, 1H); 2.78 (m, 1H); 2.10 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.51 (m, 4H);

Example No. 4-130: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.05 (br s, 1H); 8.31 (br q, 1H); 7.59 (d, 1H);

7.16 (t, 1H); 7.14 (d, 1H); 2.76 (d, 3H); 2.08 (m, 1H); 0.80 (m, 2H); 0.48 (m, 2H); Example no. 4-131: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.08 (br s, 1H); 8.38 (br t, 1H); 7.58 (d, 1H);

7.14 (t, 1H); 7.13 (d, 1H); 3.27 (m, 2H); 1.11 (t, 3H); 0.80 (m, 2H); 0.51 (m, 2H);

Example No. 4-132: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.04 (br s, 1H); 8.43 (br d, 1H); 7.58 (d, 1H);

7.14 (t, 1H); 7.13 (d, 1H); 2.78 (m, 1H); 2.07 (m, 1H); 0.80 (m, 2H); 0.68 (m, 2H); 0.50 (m, 4H);

Example no. 4-133: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.20 (br s, 1H); 8.30 (br q, 1H); 7.83 (d, 1H); 7.21 (d, 1H); 6.32 (dd, 1H); 4.42 (td, 2H); 2.73 (d, 3H);

Example No. 4-134: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.20 (br s, 1H); 8.36 (br t, 1H); 7.83 (d, 1H);

7.20 (d, 1H); 6.32 (dd, 1H); 4.45 (td, 2H); 3.22 (m, 2H); 1.08 (t, 3H);

Example No. 4-135: ¹ H-NMR (400 MHz, DMSO-d ₆ ): δ = 13.20 (br s, 1H); 8.43 (br d, 1H); 7.83 (d, 1H);

7.19 (d, 1H); 6.32 (dd, 1H); 4.40 (td, 2H); 2.74 (m, 1H); 0.67 (m, 2H); 0.46 (m, 2H);

B. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and/or its salts and 90 parts by weight of talc as an inert substance and grinding the mixture in a hammer mill. b) A wettable powder that is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of formula (I) and/or its salts, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate, and 1 part by weight of sodium oleoylmethyltaurine as wetting and dispersing agents, and grinding the mixture in a pin-type mill. c) A dispersion concentrate readily dispersible in water is obtained by mixing 20 parts by weight of a compound of 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 to over 277°C) and grinding in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and/or its salts, 75 parts by weight of cyclohexanone as solvent, and 10 parts by weight of ethoxylated nonylphenol as emulsifier. e) A water-dispersible granulate is obtained by

75 parts by weight of a compound of formula (I) and/or its salts,

10 parts by weight of calcium ligninsulfonate,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight of kaolin, grinding it on a pin mill and granulating the powder in a fluidized bed by spraying water as a granulating liquid. f) Water-dispersible granules are also obtained by

25 parts by weight of a compound of formula (I) and/or salts thereof,

5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium

2 parts by weight of oleoylmethyltaurine sodium,

1 part by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and

50 parts by weight of water homogenized and pre-crushed on a colloid mill, then ground on a bead mill and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle.

C. Biological examples

The abbreviations used here mean:

ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides

AVEFA Avena fatua AMARE Amaranthus retroflexus

CYPES Cyperus esculentus DIGSA Digitaria sanguinalis

ECHCG Echinochloa crus-galli HORMU Hordeum murinum

KCHSC Kochia scoparia LOLMU Lolium multiflorum

LOLRI Lolium rigidum MATIN Matricaria inodora

PHBPU Pharbitis purpurea POLCO Polygonum convolvulus

SETVI Setaria viridis STEME Stellaria media

VERPE Veronica persica V IOTR Viola tricolor

1. Herbicidal action against weeds in pre-emergence

Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown in wood fiber pots in sandy loam soil and covered with soil. The compounds of the invention, formulated as wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l/ha with the addition of 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and maintained under favorable growth conditions for the test plants. Visual assessment of damage to the test plants is carried out after a trial period of 3 weeks in comparison to untreated controls (herbicidal activity in percent (%): 100% activity = plants died, 0% activity = same as control plants). Numerous compounds of the invention demonstrated very good activity against a wide range of important weeds. The following tables show, by way of example, the post-emergence herbicidal activity of the compounds according to the invention, with the herbicidal activity being given in percent.

Table Cl: Pre-emergence effect at 20g/ha against ZEAMX in %

Table C-2: Pre-emergence effect at 80g/ha against ZEAMX in %

Table C-3: Pre-emergence effect at 20g/ha against TRZAS in %

Table C-4: Pre-emergence effect at 80g/ha against TRZAS in %

Table C-5: Pre-emergence effect at 20g/ha against GLXMA in %

Table C-6: Pre-emergence effect at 80g/ha against GLXMA in %

Table C-7: Pre-emergence effect at 20g/ha against BRSNW in %

Table C-8: Pre-emergence effect at 80g/ha against BRSNW in %

Table C-9: Pre-emergence effect at 20g/ha against ABUTH in %

Table C-10: Pre-emergence effect at 80g/ha against ABUTH in %

Table Cl l: Pre-emergence effect at 20g/ha against ALOMY in %

Table C-12: Pre-emergence effect at 80g/ha against ALOMY in %

Table C-13: Pre-emergence effect at 20g/ha against AM ARE in %

Table C-14: Pre-emergence effect at 80g/ha against AMARE in %

Table C-15: Pre-emergence effect at 20g/ha against AVEFA in %

Table C-16: Pre-emergence efficacy at 80g/ha against AVEFA in %

Table C-17: Pre-emergence effect at 20g/ha against DIGS A in %

Tabelle C-19: Vorauflaufwirkung bei 20g/ha gegen ECHCG in %

Table C-18: Pre-emergence effect at 80g/ha against DIGSA in %

Table C-19: Pre-emergence efficacy at 20g/ha against ECHCG in %

Table C-20: Pre-emergence efficacy at 80g/ha against ECHCG in %

Table C-21: Pre-emergence efficacy at 80g/ha against LOLRI in %

Table C-22: Pre-emergence effect at 20g/ha against MATIN in %

Tabelle C-24: Vorauflaufwirkung bei 20g/ha gegen PHBPU in %

Table C-23: Pre-emergence effect at 80g/ha against MATIN in %

Table C-24: Pre-emergence effect at 20g/ha against PHBPU in %

Tabelle C-26: Vorauflaufwirkung bei 20g/ha gegen POLCO in %

Table C-25: Pre-emergence effect at 80g/ha against PHBPU in %

Table C-26: Pre-emergence effect at 20g/ha against POLCO in %

Table C-27: Pre-emergence effect at 80g/ha against POLCO in %

Table C-28: Pre-emergence efficacy at 20g/ha against SETVI in %

Table C-29: Pre-emergence efficacy at 80g/ha against SETVI in %

Tabelle C-31: Vorauflaufwirkung bei 80g/ha gegen VERPE in %

Table C-30: Pre-emergence effect at 20g/ha against VERPE in %

Table C-31: Pre-emergence effect at 80g/ha against VERPE in %

Table C-32: Pre-emergence effect at 20g/ha against VIOTR in %

Table C-33: Pre-emergence effect at 80g/ha against VIOTR in %

Tabelle C-35: Vorauflaufwirkung bei 80g/ha gegen KCHSC in %

Table C-34: Pre-emergence effect at 20g/ha against KCHSC in %

Table C-35: Pre-emergence effect at 80g/ha against KCHSC in %

2. Herbicidal effect against post-emergence weeds

Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown in wood fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under favorable growth conditions. Two to three weeks after sowing, the test plants are treated at the single-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 parts of the plants as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l/ha with the addition of 0.2% wetting agent. After approximately 3 weeks of the test plants being kept in the greenhouse under optimal growth conditions, the effect of the preparations is visually compared to untreated

Controls were evaluated (herbicidal activity in percent (%): 100% activity = plants died, 0% activity = same as control plants). Numerous compounds of the invention demonstrated very good activity against a variety of important weeds. The following tables show examples of the postemergence herbicidal activity of the compounds of the invention, with the herbicidal activity expressed as a percentage.

Table C-36: Post-emergence effect at 20g/ha against ZEAMX in %

Table C-37: Post-emergence effect at 80g/ha against ZEAMX in %

Table C-38: Post-emergence effect at 20g/ha against TRZAS in %

Table C-39: Post-emergence effect at 80g/ha against TRZAS in %

Table C-40: Post-emergence effect at 20g/ha against GLXMA in %

Table C-41: Post-emergence effect at 80g/ha against GLXMA in %

Table C-42: Post-emergence effect at 20g/ha against BRSNW in %

Table C-43: Post-emergence effect at 80g/ha against BRSNW in %

Table C-44: Post-emergence effect at 20g/ha against ABUTH in %

Table C-45: Post-emergence effect at 80g/ha against ABUTH in %

Table C-46: Post-emergence effect at 20g/ha against ALOMY in %

Tabelle C-48: Nachauflaufwirkung bei 20g/ha gegen AMARE in %

Table C-47: Post-emergence effect at 80g/ha against ALOMY in %

Table C-48: Post-emergence effect at 20g/ha against AMARE in %

Table C-49: Post-emergence effect at 80g/ha against AMARE in %

Table C-50: Post-emergence effect at 20g/ha against AVEFA in %

Table C-51: Post-emergence effect at 80g/ha against AVEFA in %

Table C-52: Post-emergence effect at 20g/ha against DIGSA in %

Table C-53: Post-emergence effect at 80g/ha against DIGS A in %

Table C-54: Post-emergence effect at 20g/ha against ECHCG in %

Table C-55: Post-emergence effect at 80g/ha against ECHCG in %

Table C-56: Post-emergence effect at 20g/ha against LOLRI in %

Table C-57: Post-emergence effect at 80g/ha against LOLRI in %

Table C-58: Post-emergence effect at 20g/ha against MATIN in %

Table C-59: Post-emergence effect at 80g/ha against MATIN in %

Table C-60: Post-emergence effect at 20g/ha against PHBPU in %

Table C-61: Post-emergence effect at 80g/ha against PHBPU in %

Tabelle C-63: Nachauflaufwirkung bei 20g/ha gegen SETVI in %

Table C-62: Post-emergence effect at 80g/ha against POLCO in %

Table C-63: Post-emergence effect at 20g/ha against SETVI in %

Tabelle C-65: Nachauflaufwirkung bei 20g/ha gegen VERPE in %

Table C-64: Post-emergence effect at 80g/ha against SETVI in %

Table C-65: Post-emergence effect at 20g/ha against VERPE in %

Tabelle C-67: Nachauflaufwirkung bei 20g/ha gegen VIOTR in %

Table C-66: Post-emergence effect at 80g/ha against VERPE in %

Table C-67: Post-emergence effect at 20g/ha against VIOTR in %

Table C-68: Post-emergence effect at 80g/ha against VIOTR in %

Tabelle C-70: Nachauflaufwirkung bei 80g/ha gegen KCHSC in %

Table C-69: Post-emergence effect at 20g/ha against KCHSC in %

Table C-70: Post-emergence effect at 80g/ha against KCHSC in %

V er comparison attempts

In the following experiments, the herbicidal activity of numerous compounds according to the invention and the structurally closest compounds known from WO2021/204665 (DI) was compared under the above-mentioned pre-emergence and post-emergence conditions. The example numbers listed in the tables refer to the compounds according to the invention of the present application or to those of the respective comparative compounds from DI.

Herbicidal activity in pre-emergence: efg. = according to invention

Post-emergence herbicidal activity: efg. = according to the invention

Claims

Patent claims: 1. Isophthalic acid diamides of formula (I) or their salts

where the symbols and indices have the following meanings: R ^x means (C ₁ -C ₆ )-alkyl, X represents halogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, Y means halogen-(C ₁ -C ₆ )-alkoxy, Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C 6 )-alkyl, ( _{C 1} -C ₆ )-alkyl-C(O)-(C ₁ -C ₆ )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl carries m substituents R ¹ , R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C 6 )-alkyl-O-(C 1 -C ₆ )-alkyl, ( _{C 1 -C 6} )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R ² and R ³ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, and m represents 0, 1, 2 or 3. 2. Isophthalic acid diamides according to claim 1, wherein the symbols have the following meanings: R ^x means (C ₁ -C ₆ )-alkyl, X represents halogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, Y means OCF ₃ , OCHF ₂ , OCH ₂ CHF ₂ or OCF ₂ Me, Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-C(O)- (C ₁ -C ₆ )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl in each case m substituent R ¹ , R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C 6 )-alkyl-O-(C 1 -C ₆ )-alkyl, ( _{C 1 -C 6} )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R ² and R ³ independently represent hydrogen, Me, Et or c-Pr, and m represents 0, 1, 2 or 3. 3. Isophthalic acid diamides according to claim 1 or, where the symbols have the following meanings: R ^x means Me or Et, X is chlorine, bromine, methyl, ethyl or cyclopropyl, Y means OCF ₃ , OCHF ₂ or OCH ₂ CHF ₂ , Z ¹ and Z ² independently each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH ₂ , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1- Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH ₂ , EtC(O)CH ₂ , c-PrC(O) _CH2 , MeNHC(O) _CH2 , EtNHC(O) _CH2 or c-PrNHC(O) _CH2 . 4. Herbicidal compositions comprising at least one isophthalic acid diamide according to one of claims 1 to 3 in a mixture with formulation auxiliaries. 5. Herbicidal compositions according to claim 4 containing at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. 6. A method for controlling undesirable plants, characterized in that an effective amount of at least one isophthalic acid diamide according to one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 is applied to the plants or to the site of undesirable plant growth. 7. Use of isophthalic acid diamides of the formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 for controlling undesirable plants. 8. Use according to claim 7, characterized in that the isophthalic acid diamides of the formula (I) are used to combat undesirable plants in crops of useful plants. 9. Use according to claim 8, characterized in that the crop plants are transgenic crop plants. 10. Compounds of formula (II),

where the symbols and indices have the following meanings: L means halogen or R ⁴ O, X represents halogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, Y means halogen-(C ₁ -C ₆ )-alkoxy, Z ¹ and Z ² each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, halogen-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C 1 -C 6 )-alkyl, ( _{C 1} -C ₆ )-alkyl-C(O)-(C _{1 -C 6} )-alkyl or R ² R ³ NC(O)-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl carries m substituents R ¹ , R ¹ represents halogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkyl-O-(C 1 -C ₆ )-alkyl, (C _{1 -C 6} )-alkoxy, halogen-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyloxy-C(O), (C ₁ -C ₆ )-alkyloxy-C(O)-(C ₁ -C ₆ )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R ² and R ³ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, R ⁴ represents hydrogen or (C ₁ -C ₆ )alkyl, and m represents 0, 1, 2 or 3. 11. Compounds of formula (II) according to claim 10, wherein L means chlorine, methoxy or hydroxy, X is chlorine, bromine, methyl, ethyl or cyclopropyl, Y means OCF ₃ , OCHF ₂ or OCH ₂ CHF ₂ and Z ¹ and Z ² independently each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH ₂ , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2- Difluoro-l-methylcyclopropyl, 1-Methoxycyclopropyl, 1-Ethoxycyclopropyl, 1- Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH ₂ , EtC(O)CH ₂ , c-PrC(O) _CH2 , MeNHC(O) _CH2 , EtNHC(O) _CH2 or c-PrNHC(O) _CH2 .