Patent Publication Number: US-2011053778-A1

Title: 2-(3-aminobenzoyl)-3-cyclopropyl-3-oxopropanenitriles and their use as herbicides

Description:
CROSS REFERENCE TO RELATED APPLICATIONS 
     This application claims priority from EP 09009776.7 filed Jul. 29, 2009 and U.S. Provisional Application Ser. No. 61/229,337 filed Jul. 29, 2009, the contents of which are both incorporated herein by reference in their entireties. 
    
    
     BACKGROUND 
     1. Field of the Invention 
     The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants. 
     2. Description of Related Art 
     It is already known from various publications that certain 2-benzoyl-3-oxopropanenitriles have herbicidal properties. Thus, EP 213 892, WO 97/28136 and EP 625 505 describe 2-benzoyl-3-oxopropanenitriles which are substituted at the phenyl ring by various radicals. 
     The herbicidal activity of the compounds known from these publications, however, is frequently inadequate. Accordingly, it is an object of the present invention to provide herbicidally active compounds having—compared to the compounds known from the prior art—improved herbicidal properties. 
     SUMMARY 
     It has now been found that 2-(3-aminobenzoyl)-3-cyclopropyl-3-oxopropanenitriles are particularly suitable for use as herbicides. 
     The present invention provides 2-(3-aminobenzoyl)-3-cyclopropyl-3-oxopropanenitriles of the formula (I) or salts thereof 
     
       
         
         
             
             
         
       
     
     in which
 
X and Y independently of one another are nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-COOR 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1  or (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 ,
 
R 1  is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven lastmentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR S , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2  and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
 
R 2  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven lastmentioned radicals are substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR S , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2  and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
 
R 3  is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
 
R 4  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
 
n is 0, 1 or 2,
 
s is 0, 1, 2 or 3.
 
    
    
     DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT 
     In formula (I) and all the formulae below, alkyl radicals having more than two carbon atoms can be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen represents fluorine, chlorine, bromine or iodine. 
     Where a group is substituted by a plurality of radicals, this means that this group is substituted by one or more identical or different representatives of the radicals mentioned. 
     Depending on the nature and the attachment of the substituents, the compounds of the formula (I) may be present as stereoisomers. If, for example, one or more asymmetrically substituted carbon atoms are present, there may be enantiomers and diastereomers. There may also be stereoisomers if n is 1 (sulfoxides). Stereoisomers may be obtained from the mixtures resulting from the preparation using customary separation methods, for example by chromatographic separation techniques. It is also possible to prepare stereoisomers selectively by using stereoselective reactions employing optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof embraced by the formula (I) but not specifically defined. 
     The compounds of the formula (I), depending on external conditions, such as pressure, temperature, pH and solvent, may occur in different tautomeric structures, which are meant to be embraced by formula (I) mentioned above: 
     
       
         
         
             
             
         
       
     
     Preferred are compounds of the formula (I) in which 
     X and Y independently of one another are nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-COOR 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2  or (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 ,
 
R 1  is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven lastmentioned radicals are substituted by s radicals from the group consisting of halogen and OR 3 ,
 
R 2  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where these radicals mentioned above are substituted by s radicals from the group consisting of cyano, halogen and OR 3 ,
 
R 3  is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
 
R 4  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
 
n is 0, 1 or 2,
 
s is 0, 1, 2 or 3.
 
     Particular preference is given to compounds of the formula (I) in which 
     X is nitro, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, methylsulfonyl, ethylsulfonyl, methylsulfenylmethyl, methylsulfinylmethyl, methylsulfonylmethyl,
 
Y is nitro, fluorine, chlorine, bromine, iodine, cyano, methoxy, ethoxy, trifluoromethyl, methylsulfonyl, ethylsulfonyl.
 
     In all of the formulae below, the substituents and symbols have the same definition as described under formula (I), unless otherwise defined. 
     Compounds according to the invention can be prepared, for example, by the process shown in Scheme 1, which is known in principle from EP 0 625 505 A1, by reacting an acid chloride of the formula (III) with a beta-ketonitrile of the formula (II) in a suitable solvent, such as acetonitrile, under catalysis of a base, such as triethylamine, and in a second step under cyanide catalysis. 
     
       
         
         
             
             
         
       
     
     Compounds according to the invention can also be prepared, for example, by the process shown in Scheme 2 by base-catalyzed ring opening from isoxazoles (IV). The isoxazoles (II) can be synthesized from the corresponding benzoic acids (IIIa). Such syntheses are described in EP 0 625 505 A1. The preparation of the benzoic acids (IIIa) and the corresponding acid chlorides (III) is described, for example, in WO 94/14782, WO 95/16678 and WO95/31446. 
     
       
         
         
             
             
         
       
     
     Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the aforementioned reactions can also be prepared in a parallel manner, it being possible for this to take place in a manual, partly automated or completely automated manner. In this connection, it is, for example, possible to automate the reaction procedure, the work-up or the purification of the products and/or intermediates. 
     Overall, this is understood as meaning a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor Gunther Jung), Verlag Wiley 1999, on pages 1 to 34. 
     For the parallel reaction procedure and work-up, it is possible to use a series of commercially available instruments, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451, USA. For the parallel purification of compounds of the formula (I) and salts thereof or of intermediates produced during the preparation, there are available, inter alia, chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. 
     The apparatuses listed lead to a modular procedure in which the individual process steps are automated, but between the process steps manual operations have to be carried out. This can be circumvented by using partly or completely integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be acquired, for example, from Caliper, Hopkinton, Mass. 01748, USA. 
     The implementation of single or several synthesis steps can be supported through the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich). 
     Besides the methods described here, the preparation of compounds of the formula (I) and salts thereof can take place completely or partially by solid-phase supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bonded to a synthesis resin. Solid-phase supported synthesis methods are sufficiently described in the specialist literature, e.g. Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (editor Gunther Jung), Verlag Wiley, 1999. The use of solid-phase supported synthesis methods permits a series of protocols known in the literature, which again can be carried out manually or in an automated manner. The reactions can be carried out, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA. 
     Both on a solid phase and in liquid phase can the procedure of individual or several synthesis steps be supported through the use of microwave technology. The specialist literature describes a series of experimental protocols, for example in Microwaves in Organic and Medicinal Chemistry (editor C. O. Kappe and A. Stadler), Verlag Wiley, 2005. 
     The preparation according to the process described here produces compounds of the formula (I) and their salts in the form of substance collections which are called libraries. The present invention also provides libraries which comprise at least two compounds of the formula (I) and their salts. 
     The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow also referred to together as “compounds according to the invention”, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active compounds act efficiently even on perennial weeds which produce shoots from rhizomes, root stocks and other perennial organs and which are difficult to control. 
     The present invention therefore also relates to a method for controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-sowing (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Specific examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being restricted to certain species. 
     Monocotyledonous harmful plants of the genera:  Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Erio - chloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.    
     Dicotyledonous weeds of the genera:  Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.    
     If the compounds according to the invention are applied to the soil surface before germination, the weed seedlings are either prevented completely from emerging or else the weeds grow until they have reached the cotyledon stage, but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely. 
     If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage of the point of time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner. 
     Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera  Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia , or monocotyledonous crops of the genera  Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea , in particular  Zea  and  Triticum , are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamentals. 
     Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plant&#39;s metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting unwanted vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby. 
     By virtue of their herbicidal and plant-growth-regulatory properties, the active compounds can also be employed for controlling harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased, or whose starch quality is altered, or those where the harvested material has a different fatty acid composition. 
     With regard to transgenic crops, it is preferred to use the compounds according to the invention in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides. 
     It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides. 
     Conventional methods of generating novel plants which have modified properties in comparison to plants occurring to date consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:
         the modification, by recombinant technology, of crop plants with the aim of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),   transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf., for example, EP-A-0242236, EP-A-242246) or of the glyphosate type (WO 92/00377) or of the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),   transgenic crop plants, for example cotton, with the capability of producing  Bacillus thuringiensis  toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259),   transgenic crop plants with a modified fatty acid composition (WO 91/13972),   genetically modified crop plants with novel constituents or secondary metabolites, for example novel phytoalexins, which bring about an increased disease resistance (EPA 309862, EPA0464461),   genetically modified plants with reduced photorespiration which feature higher yields and higher stress tolerance (EPA 0305398), transgenic crop plants which produce pharmaceutically or diagnostically important proteins (“molecular pharming”),   transgenic crop plants which are distinguished by higher yields or better quality,   transgenic crop plants which are distinguished by a combination, for example of the abovementioned novel properties (“gene stacking”).       

     A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431). 
     To carry out such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence changes by recombination of DNA sequences can be introduced into plasmids. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments with one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone [Genes and clones]”, VCH Weinheim 2nd ed., 1996. 
     For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. To this end, it is possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, it being necessary for these portions to be long enough to have an antisense effect in the cells. The use of DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them, is also possible. 
     When expressing nucleic acid molecules in plants, the protein synthesized can be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to link the coding region with DNA sequences which ensure localization in a particular compartment. Such sequences are known to those 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). The nucleic acid molecules can also be expressed in the organelles of the plant cells. 
     The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledonous, but also dicotyledonous, plants. 
     Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or the expression of heterologous (=foreign) genes or gene sequences. 
     It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active substances. 
     When the active compounds according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants. 
     The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants. 
     The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise the compounds according to the invention. 
     The compounds according to the invention can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations 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), dusting products (DP), seed-dressing products, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. 
     These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. 
     The necessary formulation assistants, such as inert materials, surfactants, solvents and further additives, are likewise 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 &amp; Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon&#39;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 Athylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, “Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986. 
     Based on these formulations, it is also possible to produce combinations with other pesticidally active compounds, such as, for example, insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix. 
     Wettable powders are preparations which can be dispersed uniformly in water and, as well as the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation assistants. 
     Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more surfactants of the ionic and/or nonionic type (emulsifiers). The emulsifiers used may, for example, be: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters. 
     Dusts are obtained by grinding the active compound with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. 
     Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types. 
     Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as have, for example, already been listed above for the other formulation types. 
     Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers. 
     Water-dispersible granules are prepared generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material. 
     For the preparation of pan, fluidized bed, extruder and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 if; “Perry&#39;s Chemical Engineer&#39;s Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57. 
     For further details regarding the formulation of crop protection compositions, 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 formulations contain generally from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active compound concentration is, for example, from about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation components. In the case of emulsifiable concentrates, the active compound concentration can be from about 1 to 90, preferably from 5 to 80, % by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active compound, preferably usually from 5 to 20% by weight of active compound; sprayable solutions contain from about 0.05 to 80% by weight, preferably from 2 to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight. 
     In addition, the active compound formulations mentioned optionally comprise the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. 
     Based on these formulations, it is also possible to produce combinations with other pesticidally active compounds, such as, for example, insecticides, acaricides, herbicides, fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix. 
     Active compounds which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here, by way of example, one and in some cases a plurality of use forms are mentioned: 
     acetochlor, acibenzolar, acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryn, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, IDH-100, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methazole, methiozolin, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium (isomer mixture), nitrofluorfen, nonanoic acid, nofflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, TH-547, thenylchlor, thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds 
     
       
         
         
             
             
         
       
     
     For application, the formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Preparations in the form of dusts, granules for soil application or granules for broadcasting and sprayable solutions are usually not diluted with other inert substances prior to application. 
     The required application rate of the compounds of the formula (I) varies according to the external conditions such as, inter alia, temperature, humidity and the type of herbicide used. It may vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance; however, preferably it is between 0.005 and 750 g/ha. 
     The examples below illustrate the invention: 
     A. Chemical Examples 
     Preparation of 2-(3-amino-2-methyl-4-(trifluoromethyl)benzoyl)-3-cyclopropyl-3-oxopropanenitrile (Table example No. 3) 
     Step 1: Synthesis of 3-fluoro-N-(1-hydroxy-2-methylpropan-2-yl)-4-(trifluoromethyl)benz-amide 
     10.0 g (48.0 mmol) of 3-fluoro-4-(trifluoromethyl)benzoic acid were initially charged in 40 ml of CH 2 Cl 2 , and five drops of DMF were added. 7.93 g (62.4 mmol) of oxalyl chloride were added slowly at room temperature (RT), and the mixture was, after the evolution of gas had ceased, heated under reflux until the reaction had gone to completion. The mixture was concentrated and then distilled once more with toluene. In a temperature range of 5-25° C., a solution of this crude acid chloride in 40 ml of CH 2 Cl 2  was added dropwise to a solution of 8.57 g (96.1 mmol) of 2-amino-2-methylpropanol in 20 ml of CH 2 Cl 2 . The mixture was then stirred in an ice bath for 1.5 h and subsequently thawed to RT over a period of 16 h. The precipitated hydrochloride was separated off, the residue was washed with a large quantity of CH 2 Cl 2  and the filtrate was evaporated to dryness. This gave 8.40 g of product of a purity of about 80%. Furthermore, the residue separated off at the beginning of the work-up was triturated with water and filtered again. The residue obtained was another 4.60 g of clean product. 
     Step 2: Synthesis of 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
     9.60 g (purity 85% by weight; 29.2 mmol) of 3-fluoro-N-(1-hydroxy-2-methylpropan-2-yl)-4-(trifluoromethyl)benzamide were initially charged in 80 ml of CH 2 Cl 2 , and 4.17 g (35.0 mmol) of thionyl chloride were added. The mixture was stirred at RT for 5 h and then poured into ice-water for work-up. The content was made alkaline with 1 M aqueous sodium hydroxide solution, and the aqueous phase was extracted twice with CH 2 Cl 2 . The combined organic phases were dried and concentrated. Finally, the crude product was purified chromatographically, which gave 5.05 g of clean product. 
     Step 3: Synthesis of 2-(3-fluoro-2-methyl-4-(trifluoromethyl)phenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
     Under protective gas, 30.3 g (116 mmol) of 2-[3-fluoro-4-(trifluoromethyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole were initially charged in 350 ml of dry THF and cooled to −70° C. At a temperature of from −62° C. to −66° C., 7.80 g (122 mmol) of n-butyllithium as a 2.50 M solution in heptane were slowly added dropwise. The content was stirred at about −70° C. for another 1.75 h. A solution of 20.6 g (145 mmol) of iodomethane in 50 ml of dry THF was then added dropwise. The mixture was stirred at about −70° C. for 30 min and then allowed to stand for 16 h, during which time it thawed to RT. For work-up, 300 ml of 1 M hydrochloric acid were added to the content at 10° C.-15° C., and water was then added. The mixture was extracted twice with diethyl ether, and the combined organic phases were washed with aqueous 10% strength sodium bisulfite solution, dried and freed from the solvent. Finally, the crude product was purified chromatographically, which gave 9.20 g of clean product. 
     Step 4: Synthesis of N-(3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-methyl-6-(trifluoromethyl)phenyl)formamide 
     8.51 g (189 mmol) of formamide and 10.6 g (94.5 mmol) of potassium tert-butoxide were initially charged in 90 ml of N,N-dimethylacetamide and stirred, and after 5 min 5.20 g (18.9 mmol) of 2-[3-fluoro-2-methyl-4-(trifluoromethyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole were added. The mixture was heated to 140° C. for 45 minutes and then concentrated under a high vacuum. 400 ml of a 1 M solution of HCl in ethanol were then added to the residue, and the mixture was then concentrated. The residue was taken up in CH 2 Cl 2  and filtered. The residue was washed with CH 2 Cl 2 , and the filtrate was then freed from the solvent. Finally, the crude product was purified chromatographically, which gave 4.30 g of clean product. 
     Step 5: Synthesis of 3-amino-2-methyl-4-(trifluoromethyl)benzoic acid 
     80 ml of concentrated hydrochloric acid were added to 3.90 g (13.0 mmol) of N-[3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]formamide, and the mixture was heated under reflux. After 4 h, the mixture was cooled and filtered, and the residue was washed with water and then dried by suction. The residue obtained was 1.40 g of clean product. The filtrate was extracted three times with ethyl acetate (EA), and the combined organic phases were dried and then freed from the solvent. The residue was triturated with a lithe 1 M hydrochloric acid and filtered, which isolated another 800 mg of clean product as residue. 
     Step 6: Synthesis of tert-butyl 2-(3-amino-2-methyl-4-(trifluoromethyl)benzoyl)-3-cyclopropyl-3-oxopropanoate 
     500 mg (2.28 mmol) of 3-amino-2-methyl-4-(trifluoromethyl)benzoic acid were initially charged in 10 ml of dry tetrahydrofuran and cooled in an ice bath to from 0° C. to 5° C. After addition of 481 mg (2.51 mmol) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide and 339 mg (2.51 mmol) of 1-hydroxybenzotriazole, the mixture was stirred in an ice bath at from 0° C. to 5° C. for 6 h and then thawed to RT. The mixture was allowed to stand at RT for 16 h. For work-up, the content was filtered and the filtrate was reacted further in a subsequent step. 630 mg (3.42 mmol) of tert-butyl 3-cyclopropyl-3-oxopropanoate were dissolved in 10 ml of dry THF, and 137 mg (60%; 3.42 mmol) of sodium hydride were added carefully. The mixture was stirred at RT for 2 h. At RT, the solution, prepared above, of the activated 3-amino-2-methyl-4-(trifluoromethyl)benzoic acid in tetrahydrofuran was then added dropwise to this mixture. The resulting suspension was stirred at RT for 2 h. For work-up, the solvent was removed, the residue was taken up in water, the content was acidified with 1 M hydrochloric acid and the mixture was extracted twice with CH 2 Cl 2 . The combined organic phases were freed from the solvent and the residue (1.40 g) was, as crude product without any further purification, used directly for the next synthesis step. 
     Step 7: Synthesis of 1-(3-amino-2-methyl-4-(trifluoromethyl)phenyl)-3-cyclopropyl-propane-1,3-dione 
     5.0 ml of trifluoroacetic acid were added to 1.40 g of the crude product tert-butyl 2-(3-amino-2-methyl-4-(trifluoromethyl)benzoyl)-3-cyclopropyl-3-oxopropanoate prepared in step 6, and the mixture was then heated under reflux. When HPLC analysis showed complete conversion, the mixture was concentrated and the residue was purified chromatographically. This gave 300 mg of the product in a purity of about 83% by weight. 
     Step 8: Synthesis of 1-(3-amino-2-methyl-4-(trifluoromethyl)phenyl)-3-cyclopropyl-2-[(dimethylamino)methylene]propane-1,3-dione 
     3.0 ml of N,N-dimethylformamide dimethyl acetal were added to 340 mg (purity 80% by weight; 0.95 mmol) of 1-[3-amino-2-methyl-4-(trifluoromethyl)phenyl]-3-cyclopropylpropane-1,3-dione, and the mixture was stirred at RT for 16 h. For work-up, twice n-heptane was added and then decanted off. The residue was dried. This gave 268 mg of clean product. 
     Step 9: Synthesis of 4-(3-amino-2-methyl-4-(trifluoromethyl)benzoyl)-5-cyclopropylisoxazole 
     268 mg (0.79 mmol) of 1-[3-amino-2-methyl-4-(trifluoromethyl)phenyl]-3-cyclopropyl-2-[(dimethylamino)methylene]propane-1,3-dione were dissolved in 25 ml of ethanol. 66 mg (0.95 mmol) of hydroxylammonium chloride were added, followed after 5 min by 77.5 mg (0.95 mmol) of sodium acetate. The reaction mixture was stirred at RT until HPLC showed complete conversion. The content was freed from the solvent, and the residue was taken up in EA and water. The aqueous phase was extracted once with EA, and the combined organic phases were washed once with 1 M hydrochloric acid, dried and freed from the solvent. Finally, the crude product was purified chromatographically, which gave 80 mg of the product in a purity of about 90% by weight. 
     Step 10: Synthesis of 2-(3-amino-2-methyl-4-(trifluoromethyl)benzoyl)-3-cyclopropyl-3-oxopropanenitrile (No. 3) 
     40.0 mg (0.13 mmol) of 4-[3-amino-2-methyl-4-(trifluoromethyl)benzoyl]-5-cyclopropylisoxazole were initially charged in 5 ml of dichloromethane and, after addition of 26 mg (0.26 mmol) of triethylamine, stirred at RT for 16 h. For work-up, 3 ml of 1 M hydrochloric acid were added, and the organic phase was freed from the solvent. This gave 37.8 mg of the product in a purity of about 90% by weight. 
     The examples listed in the tables below were prepared analogously to the methods mentioned above or can be obtained analogously to the methods mentioned above. These compounds are very particularly preferred. 
     The abbreviations used denote: 
     Et=ethyl Me=methyl 
     
       
         
           
               
             
               
                 TABLE 
               
             
            
               
                   
               
               
                 Compounds of the formula (I) according to the invention 
               
               
                 (I) 
               
               
                 
                   
                     
                     
                         
                         
                     
                   
                 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                   
                   
                   
                 Physical data: 
               
               
                 No. 
                 X 
                 Y 
                   1 H-NMR: δ [CDCl 3 ] 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 1 
                 Me 
                 SO 2 Me 
                 17.45 (br. s, 1H), 7.77 (d, 1H), 6.90 (d, 1H), 5.29  
               
               
                   
                   
                   
                 (br. s, 2H), 3.08 (s, 3H), 2.40 (m. 1H), 2.23 (s, 3H),  
               
               
                   
                   
                   
                 1.44 (m, 2H), 1.31 (m, 2H) 
               
               
                 2 
                 Me 
                 SO 2 Et 
                   
               
               
                 3 
                 Me 
                 CF 3   
                 17.48 (br. s, 1H), 7.42 (d, 1H), 6.86 (d, 1H), 2.41 m. 1H), 2.21 (s, 3H), 1.42 (m, 2H), 1.28 (m, 2H) 
               
               
                 4 
                 Me 
                 F 
                   
               
               
                 5 
                 Me 
                 Cl 
                   
               
               
                 6 
                 Me 
                 Br 
                   
               
               
                 7 
                 Me 
                 I 
                   
               
               
                 8 
                 Me 
                 CN 
                   
               
               
                 9 
                 Me 
                 OMe 
                   
               
               
                 10 
                 Me 
                 OEt 
                   
               
               
                 11 
                 Me 
                 NO 2   
                   
               
               
                 12 
                 Et 
                 SO 2 Me 
                   
               
               
                 13 
                 Et 
                 SO 2 Et 
                   
               
               
                 14 
                 Et 
                 CF 3   
                   
               
               
                 15 
                 Et 
                 F 
                   
               
               
                 16 
                 Et 
                 Cl 
                   
               
               
                 17 
                 Et 
                 Br 
                   
               
               
                 18 
                 El 
                 I 
                   
               
               
                 19 
                 El 
                 CN 
                   
               
               
                 20 
                 El 
                 OMe 
                   
               
               
                 21 
                 El 
                 OEt 
                   
               
               
                 22 
                 El 
                 NO 2   
                   
               
               
                 23 
                 SO 2 Me 
                 SO 2 Me 
                   
               
               
                 24 
                 SO 2 Me 
                 SO 2 Et 
                   
               
               
                 25 
                 SO 2 Me 
                 CF 3   
                 16.48 (br. s, 1H), 7.76 (d, 1H), 6.78 (d, 1H), 3.24 (s, 3H), 2.26 (m. 1H), 1.50-1.37 (m, 2H). 1.32 (m, 2H) 
               
               
                 26 
                 SO 2 Me 
                 F 
                   
               
               
                 27 
                 SO 2 Me 
                 Cl 
                   
               
               
                 28 
                 SO 2 Me 
                 Br 
                   
               
               
                 29 
                 SO 2 Me 
                 I 
                   
               
               
                 30 
                 SO 2 Me 
                 CN 
                   
               
               
                 31 
                 SO 2 Me 
                 OMe 
                   
               
               
                 32 
                 SO 2 Me 
                 OEt 
                   
               
               
                 33 
                 SO 2 Me 
                 NO 2   
                   
               
               
                 34 
                 SO 2 Me  
                 SO 2 Me 
                   
               
               
                 35 
                 SO 2 Et 
                 SO 2 Et 
                   
               
               
                 36 
                 SO 2 Et 
                 CF 3   
                   
               
               
                 37 
                 SO 2 Et 
                 F 
                   
               
               
                 38 
                 SO 2 Et 
                 Cl 
                   
               
               
                 39 
                 SO 2 Et. 
                 Br 
                   
               
               
                 40 
                 SO 2 Et 
                 I 
                   
               
               
                 41 
                 SO 2 Et 
                 CN 
                   
               
               
                 42 
                 SO 2 Et 
                 OMe 
                   
               
               
                 43 
                 SO 2 Et 
                 OEt 
                   
               
               
                 44 
                 SO 2 Et 
                 NO 2   
                   
               
               
                 45 
                 CF 3   
                 SO 2 Me 
                   
               
               
                 46 
                 CF 3   
                 SO,Et 
                   
               
               
                 47 
                 CF 3   
                 CF 3   
                   
               
               
                 48 
                 CF 3   
                 F 
                   
               
               
                 49 
                 CF 3   
                 Cl 
                   
               
               
                 50 
                 CF 3   
                 Br 
                   
               
               
                 51 
                 CF 3   
                 I 
                   
               
               
                 52 
                 CF 3   
                 CN 
                   
               
               
                 53 
                 CF 3   
                 OMe 
                   
               
               
                 54 
                 CF 3   
                 OEt 
                   
               
               
                 55 
                 CF 3   
                 NO 2   
                   
               
               
                 56 
                 F 
                 SO 2 Me 
                   
               
               
                 57 
                 F 
                 SO 2 Et 
                   
               
               
                 58 
                 F 
                 CF 3   
                   
               
               
                 59 
                 r 
                 F 
                   
               
               
                 60 
                 F 
                 Cl 
                   
               
               
                 61 
                 F 
                 Br 
                   
               
               
                 62 
                 F 
                 I 
                   
               
               
                 63 
                 F 
                 CN 
                   
               
               
                 64 
                 F 
                 OMe 
                   
               
               
                 65 
                 F 
                 OEt 
                   
               
               
                 66 
                 F 
                 NO 2   
                   
               
               
                 67 
                 Cl 
                 SO 2 Me 
                   
               
               
                 68 
                 Cl 
                 SO 2 Et 
                   
               
               
                 68 
                 Cl 
                 CF 3   
                   
               
               
                 70 
                 Cl 
                 F 
                   
               
               
                 71 
                 Cl 
                 Cl 
                   
               
               
                 72 
                 Cl 
                 Br 
                   
               
               
                 73 
                 Cl 
                 I 
                   
               
               
                 74 
                 Cl 
                 CN 
                   
               
               
                 75 
                 Cl 
                 OMe 
                   
               
               
                 76 
                 Cl 
                 OEt 
                   
               
               
                 77 
                 Cl 
                 NO 2   
                   
               
               
                 78 
                 Br 
                 SO 2 Me 
                   
               
               
                 79 
                 Br 
                 SO 2 Et 
                   
               
               
                 80 
                 Br 
                 CF 3   
                   
               
               
                 81 
                 Br 
                 F 
                   
               
               
                 82 
                 Br 
                 Cl 
                   
               
               
                 83 
                 Br 
                 Br 
                   
               
               
                 84 
                 Br 
                 I 
                   
               
               
                 85 
                 Br 
                 CN 
                   
               
               
                 86 
                 Br 
                 OMe 
                   
               
               
                 87 
                 Br 
                 OEt 
                   
               
               
                 88 
                 Br 
                 NO 2   
                   
               
               
                 89 
                 I 
                 SO 2 Me 
                   
               
               
                 90 
                 I 
                 SO 2 Et 
                   
               
               
                 91 
                 I 
                 CF 3   
                   
               
               
                 92 
                 I 
                 F 
                   
               
               
                 93 
                 I 
                 Cl 
                   
               
               
                 94 
                 I 
                 Br 
                   
               
               
                 95 
                 I 
                 I 
                   
               
               
                 96 
                 I 
                 CN 
                   
               
               
                 97 
                 I 
                 OMe 
                   
               
               
                 98 
                 I 
                 OEt 
                   
               
               
                 99 
                 I 
                 NO 2   
                   
               
               
                 100 
                 CN 
                 SO 2 Me 
                   
               
               
                 101 
                 CN 
                 SO 2 Et 
                   
               
               
                 102 
                 CN 
                 CF 3   
                   
               
               
                 103 
                 CN 
                 F 
                   
               
               
                 104 
                 CN 
                 Cl 
                   
               
               
                 105 
                 CN 
                 Br 
                   
               
               
                 106 
                 CN 
                 I 
                   
               
               
                 107 
                 CN 
                 CN 
                   
               
               
                 108 
                 CN 
                 OMe 
                   
               
               
                 109 
                 CN 
                 OEt 
                   
               
               
                 110 
                 CN 
                 NO 2   
                   
               
               
                 111 
                 OMe 
                 SO 2 Me 
                   
               
               
                 112 
                 OMe 
                 SO 2 Et 
                   
               
               
                 113 
                 OMe 
                 CF 3   
                   
               
               
                 114 
                 OMe 
                 F 
                   
               
               
                 115 
                 OMe 
                 Cl 
                 17.5 (s, br, 1H), ), 7.15 (d, 1H), 6.8 (d. 1H). 3.9- 4.5 (s, br, 2H), 3.8(s, 3H), 2.42 (m, 1H), 1.4 (m, 2H). 1.25 (m, 2H) 
               
               
                 116 
                 OMe 
                 Br 
                   
               
               
                 117 
                 OMe 
                 I 
                   
               
               
                 118 
                 OMe 
                 CN 
                   
               
               
                 119 
                 OMe 
                 OMe 
                   
               
               
                 120 
                 OMe 
                 OEt 
                   
               
               
                 121 
                 OMe 
                 NO 2   
                   
               
               
                 122 
                 OEt 
                 SO 2 Me 
                   
               
               
                 123 
                 OEt 
                 SO 2 Et 
                   
               
               
                 124 
                 OEt 
                 CF 3   
                   
               
               
                 125 
                 OEt 
                 F 
                   
               
               
                 126 
                 OEt 
                 Cl 
                   
               
               
                 127 
                 OEt 
                 Br 
                   
               
               
                 128 
                 OEt 
                 I 
                   
               
               
                 129 
                 OEt 
                 CN 
                   
               
               
                 130 
                 OEt 
                 OMe 
                   
               
               
                 131 
                 OEt 
                 OEt 
                   
               
               
                 132 
                 OEt 
                 NO 2   
                   
               
               
                 133 
                 CH 2 SMe 
                 SO 2 Me 
                   
               
               
                 134 
                 CH 2 SMe 
                 SO 2 Et 
                   
               
               
                 135 
                 CH 2 SMe 
                 CF 3   
                   
               
               
                 136 
                 CH 2 SMe 
                 F 
                   
               
               
                 137 
                 CH 2 SMe 
                 Cl 
                   
               
               
                 138 
                 CH 2 SMe 
                 Br 
                   
               
               
                 139 
                 CH 2 SMe 
                 I 
                   
               
               
                 140 
                 CH 2 SMe 
                 CN 
                   
               
               
                 141  
                 CH 2 SMe 
                 OMe 
                   
               
               
                 142  
                 CH 2 SMe 
                 OEt 
                   
               
               
                 143 
                 CH 2 SMe 
                 NO 2   
                   
               
               
                 144 
                 CH 2 SOMe 
                 SO 2 Me 
                   
               
               
                 145 
                 CH 2 SOMe 
                 SO 2 Et 
                   
               
               
                 146 
                 CH 2 SOMe 
                 CF 3   
                   
               
               
                 147 
                 CH 2 SOMe 
                 F 
                   
               
               
                 148 
                 CH 2 SOMe 
                 Cl 
                   
               
               
                 149  
                 CH 2 SOMe 
                 Br 
                   
               
               
                 150 
                 CH 2 SOMe 
                 I 
                   
               
               
                 151 
                 CH 2 SOMe 
                 CN 
                   
               
               
                 152 
                 CH 2 SOMe 
                 OMe 
                   
               
               
                 153 
                 CH 2 SOMe 
                 OEt 
                   
               
               
                 154 
                 CH 2 SOMe 
                 NO 2   
                   
               
               
                 155 
                 CH 2 SOMe 
                 SO 2 Me 
                   
               
               
                 156 
                 CH 2 SOMe 
                 SO 2 Et 
                   
               
               
                 157 
                 CH 2 SOMe 
                 CF 3   
                   
               
               
                 158 
                 CH 2 SOMe 
                 F 
                   
               
               
                 159 
                 CH 2 SOMe 
                 Cl 
                   
               
               
                 160 
                 CH 2 SOMe 
                 Br 
                   
               
               
                 161 
                 CH 2 SOMe 
                 I 
                   
               
               
                 162 
                 CH 2 SOMe 
                 CN 
                   
               
               
                 163 
                 CH 2 SOMe 
                 OMe 
                   
               
               
                 164 
                 CH 2 SOMe 
                 OEt 
                   
               
               
                 165 
                 CH 2 SOMe 
                 NO 2   
                   
               
               
                 166 
                 NO 2   
                 SO 2 Me 
                   
               
               
                 167 
                 NO 2   
                 SO 2 Et 
                   
               
               
                 168 
                 NO 2   
                 CF 3   
                   
               
               
                 169 
                 NO 2   
                 F 
                   
               
               
                 170 
                 NO 2   
                 Cl 
                   
               
               
                 171 
                 NO 2   
                 Br 
                   
               
               
                 172 
                 NO 2   
                 I 
                   
               
               
                 173 
                 NO 2   
                 CN 
                   
               
               
                 174 
                 NO 2   
                 OMe 
                   
               
               
                 175 
                 NO 2   
                 OEt 
               
               
                   
               
            
           
         
       
     
     B. Formulation Examples 
     
         
         a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or a salt thereof and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill. 
         b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or a salt thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. 
         c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or a salt thereof 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 about 255 to above 277° C.) and grinding the mixture in a ball mill to a fineness of below 5 microns. 
         d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or a salt thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier. 
         e) Water-dispersible granules are obtained by mixing
       75 parts by weight of a compound of the formula (I) and/or a salt thereof,   10 parts by weight of calcium lignosulfonate,   5 parts by weight of sodium lauryl sulfate,   3 parts by weight of polyvinyl alcohol and   7 parts by weight of kaolin,   grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spraying on water as granulating liquid.   
     
         f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
       25 parts by weight of a compound of the formula (I) and/or a salt thereof,   5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,   2 parts by weight of sodium oleoylmethyltaurinate,   1 part by weight of polyvinyl alcohol,   17 parts by weight of calcium carbonate and   50 parts by weight of water,   subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.   
     
       
    
     C. Biological Examples 
     1. Pre-Emergence Herbicidal Action Against Harmful Plants 
     Seeds of monocotyledonous or dicotyledonous weed plants or crop plants are placed in wood-fiber pots in sandy loam and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% of wetting agent to the surface of the covering soil. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a trial period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example, the compounds Nos. 1, 3 and 25 each show, at an application rate of 80 g/ha, an activity of at least 90% against  Amaranthus retroflexus, Echinochloa crus galli  and  Veronica persica.    
     2. Post-Emergence Herbicidal Action Against Harmful Plants 
     Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% of wetting agent onto the green parts of the plants. After the test plants have been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations is rated visually in comparison to untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, for example, the compounds Nos. 1, 3 and 25 each show, at an application rate of 80 g/ha, an activity of at least 80% against  Echinochloa crus galli, Matricaria inodora, Stellaria media  and  Veronica persica.