Herbicidal malonamides

Abstract

The present invention relates to compounds of formula (I) and their use as herbicides. In said formula, R 1 - R 9 represents a group such as hydrogen, halogen or an organic group such as alkyl, alkenyl, alkynyl or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxy or a linear or cyclic organic group. The invention also relates to compositions comprising such compounds and their use for controlling unwanted plants.

Description

[0001] The present invention relates to malonamide compounds and compositions comprising these. The present invention also relates to the use of malonamide compounds or corresponding compositions for controlling undesirable vegetation. In addition, the present invention relates to methods for applying malonamide compounds or corresponding compositions.

[0002] For controlling undesirable vegetation, especially in crop plants, there is a continuous need for new herbicides which have a high degree of activity and selectivity and which are not significantly toxic to humans and animals.

[0003] WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 and WO19145245 describe 3-phenylisoxazoline-5-carboxamides and their use as herbicides.

[0004] WO 87 / 05898 describes the use of malonic acid derivatives for retarding the growth of plants.

[0005] US 3,072,473 describes malonic acid derivatives as plant growth regulators.

[0006] The compounds of the prior art often have insufficient herbicidal activity, especially at low application rates, and / or unsatisfactory selectivity, resulting in low compatibility with crop plants.

[0007] The object of the present invention was therefore to provide further malonamide compounds which have strong herbicidal activity, particularly even at low application rates, sufficiently low toxicity to humans and animals and / or high compatibility with crop plants. The malonamide compounds should also exhibit a broad spectrum of activity against a large number of different undesirable plants.

[0008] These and other objects are achieved by the compounds of formula (I) as defined below, including their agriculturally acceptable salts, amides, esters or thioesters.

[0009] Therefore, the present invention provides compounds of formula (I):

[0010]

[0011] The substituents have the following meanings:

[0012] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0013] R 2hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy;

[0014] R 3 hydrogen, halogen, nitro, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, hydroxy-Ci-C3-alkyl, C3-C5-cycloalkyl, C3-C5-halocycloalkyl, hydroxy-C3-C5-cycloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxycarbonyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C2-C3-haloalkynyl, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl;

[0015] R 4 hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C4-halocycloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, C2-C3-haloalkenyl, C2-C3-haloalkynyl, Ci-C3-alkylthio;

[0016] R 5 hydrogen, halogen, nitro, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, hydroxy-Ci-C3-alkyl, C3-C5-cycloalkyl, C3-C5-halocycloalkyl, hydroxy-C3-C5-cycloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxycarbonyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C2-C3-haloalkynyl, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl;

[0017] R 6 hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy;

[0018] R 7 Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, Ci-C3-alkoxy-Ci-C3-alkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;

[0019] R 8hydrogen, halogen, cyano, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-cyanoalkyl, Ci-C3-hydroxyalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, Ci-C3-haloalkoxy-Ci-C3-alkyl, C3-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-haloalkoxy, Ci-C3-cyanoalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, C3-C5-cycloalkyl-Ci-C3-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C3-alkylthio;

[0020] R 9 hydrogen, halogen, cyano, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy;

[0021] X bond (X 0 ) or a bivalent unit selected from the group consisting of (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0022]

[0023] R 10 -R 15 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e , CONR b R d , NR b CO2R e , R a , or Ci-C6-alkyl, C3-C5-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, imidazolyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and Ci-C2-alkoxy;

[0024] Y hydrogen, cyano, hydroxyl, Z, or Ci-C 12 alkyl, C3-C8-cycloalkyl, C2-C12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e , CONR b R h , COR b , CONR e SO2R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO2R e , NR b SO2R e NR b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e ;

[0025] Z 3, 4, 5 or 6 membered saturated, partially unsaturated, completely unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , COR b , CONR e SO2R a , NR b R e , NR b CORe NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f C(R b )=NOR e R b R c R e R f and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0026] R a C1-C6alkyl, C2-C4alkynyl or C3-C6cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3alkoxy;

[0027] R b hydrogen or R a ;

[0028] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0029] R d hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C3-C6cycloalkyl-C1-C3alkyl, phenyl-C1-C3alkyl, furanyl-C1-C3alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2R a , CONR b R h , C1-C2alkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;

[0030] R e R d ;

[0031] R f C1-C3alkyl or C1-C3alkoxy;

[0032] R h hydrogen or C1-C6alkyl, C1-C2alkoxy, C3-C6cycloalkyl, C2-C4alkenyl, C1-C6alkoxycarbonyl-C1-C6alkyl or C2-C4alkinyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2R a and C1-C2alkoxy;

[0033] m 0, 1, 2, 3, 4 or 5;

[0034] n 0, 1 or 2;

[0035] r 1, 2, 3, 4, 5 or 6;

[0036] including their agriculturally acceptable salts, amides, esters or thioesters, with the proviso that the compounds of formula (I) have a carboxyl group.

[0037] The present application also provides formulations comprising at least one compound of formula (I) and at least one adjuvant which is customary for formulating crop protection agents.

[0038] The present application also provides combinations comprising at least one compound of formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C).

[0039] The present application also provides the use of the compounds of formula (I) as herbicides, i.e. for controlling undesirable plants.

[0040] Furthermore, the present application provides a method for controlling undesirable plants, wherein a herbicidally effective amount of at least one compound of formula (I) is allowed to act on the plants, their seed and / or their habitat.

[0041] If the compounds of formula (I), the herbicidal compounds B and / or the safeners C described herein are capable of forming geometric isomers, for example E / Z isomers, both the pure isomers and mixtures thereof can be used according to the application.

[0042] If the compounds of formula (I), the herbicidal compounds B and / or the safeners C described herein have one or more centers of chirality and thus exist as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof can be used according to the application.

[0043] If the compounds of the formula (I), the herbicidal compounds B and / or the safeners C described herein have ionizable functional groups, they can also be used in the form of their agriculturally suitable salts. Suitable are, in general, those salts of cations and those acid addition salts of acids whose cations and anions, respectively, have no adverse effect on the action of the active compounds.

[0044] Preferred cations are the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, triisopropylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetra- butylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1 -oxy)eth-1 - ylammonium (diglycolamine salt), di(2-hydroxyeth-1 -yl)ammonium (dialcoholamine salt), tri(2-hydroxyethyl)ammonium (trialcoholamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally salts of polyamines, such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0045] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, methylsulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0046] The compounds of the formula (I), the herbicidal compounds B and / or the safeners C described herein having a carboxyl group can be in the form of the acid, in the form of an agriculturally suitable salt as described above or in the form of an agriculturally suitable derivative, for example as an amide, such as mono- and di-Ci-C6-alkylamides or arylamides, as an ester, for example as an allyl ester, propargyl ester, Ci-C4-alkyl ester, alkoxyalkyl ester, tetrahydrofurfuryl ((tetrahydrofuran-2-yl)methyl) ester and also as a thioester, for example as a Ci-C4-alkyl thioester. 10 The compounds of the formula (I), the herbicidal compounds B and / or the safeners C described herein having a carboxyl group can be in the form of the acid, in the form of an agriculturally suitable salt as described above or in the form of an agriculturally suitable derivative, for example as an amide, such as mono- and di-Ci-C6-alkylamides or arylamides, as an ester, for example as an allyl ester, propargyl ester, Ci-C4-alkyl ester, alkoxyalkyl ester, tetrahydrofurfuryl ((tetrahydrofuran-2-yl)methyl) ester and also as a thioester, for example as a Ci-C4-alkyl thioester. 10Alkylthio esters are used. Preferred mono- and di-C1-C6 alkylamides are methyl and dimethylamides. Preferred arylamide is for example benzamide and 2-chlorobenzeneamide. Preferred alkyl esters are for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C1-C4 alkoxy-C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl esters. Straight-chain or branched C1-C 10 An example of an alkylthioester is ethylthioester.

[0047] The terms of organic radicals used in the definitions of the variables, such as the expression "halogen", are collective terms representing the individual members of these groups of organic units.

[0048] Prefix C x -C y Indicates the possible number of carbon atoms in a particular case. All hydrocarbon chains may be straight or branched.

[0049] Halogen: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine;

[0050] Alkyl and alkyl moieties of composite groups such as alkoxy, alkylamino, alkylthio, and alkoxycarbonyl: saturated straight-chain or branched hydrocarbon groups with 1 to 10 carbon atoms, such as C1-C 10 Alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethyl Butyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl, 2-ethylhexyl and positional isomers thereof; nonyl, decyl and positional isomers thereof;

[0051] haloalkyl: straight-chain or branched alkyl groups (as mentioned above) having 1 to 10 carbon atoms, in which some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above. In one embodiment, the alkyl groups are substituted at least once or completely by specific halogen atoms, preferably fluorine, chlorine or bromine. In another embodiment, the alkyl groups are partially or completely halogenated by different halogen atoms; in the case of mixed halogen substitution, a combination of chlorine and fluorine is preferred. Particular preference is given to Ci-C3haloalkyl, more preferably Ci-C2haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;

[0052] Alkynyl and also alkynyl moieties in complex groups such as alkynyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one triple bond in any position. According to the application, it can be preferred to use small alkynyl groups, such as C2-C4-alkynyl; on the other hand, it can also be preferred to use larger alkynyl groups, such as C5-C8-alkynyl. Examples of alkynyl groups are, for example, C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-methyl-ethynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-1-propynyl, 2-methyl-1-propynyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-1-butynyl, 2-methyl-1-butynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 2-methyl-2-butynyl, 3-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1,2-dimethyl-1-propynyl, 1,2-dimethyl-2-propynyl, 1-ethyl-1-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-1-pentynyl, 2-methyl-1-pentynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2-pentynyl, 3-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 3-methyl-3-pentynyl, 4-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-1-butynyl, 1,2-dimethyl-2-butynyl, 1,2-dimethyl-3-butynyl, 1,3-dimethyl-1-butynyl, 1,3-dimethyl-2-butynyl, 1,3-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 2,3-dimethyl-1-butynyl, 2,3-dimethyl-2-butynyl, 2,3-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 3,3-dimethyl-2-butynyl, 1-ethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-1-butynyl, 2-ethyl-2-butynyl, 2-ethyl-3-butynyl, 1,1,2-trimethyl-2-propynyl, 1-ethyl-1-methyl-2-propynyl, 1-ethyl-2-methyl-1-propynyl and 1-ethyl-2-methyl-2-propynyl;

[0053] Haloalkynyl: alkynyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bromoprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1,1 -difluorobut-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-1 -yl or 6-iodohex-5-yn-1 -yl;

[0054] Alkynyl and alkynyl moieties in complex groups such as alkyonyloxy: straight-chain or branched hydrocarbon groups having 2 to 10 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

[0055] Haloalkynyl: alkynyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bromoprop-2-yn-1 -yl, 3-iodoprop-2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1 -yl, 1,1 -difluorobut-2-yn-1 -yl, 4-iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-1 -yl or 6-iodohex-5-yn-1 -yl;

[0056] Cycloalkyl and also the cycloalkyl moiety in complex radicals: a monocyclic or bicyclic saturated hydrocarbon radical having 3 to 10, in particular 3 to 6 carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Examples of bicyclic radicals include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. In this connection, optionally substituted C3-C8-cycloalkyl means a cycloalkyl radical having 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1, 2, 3, 4 or 5 hydrogen atoms, is / are replaced by a substituent which is inert under the reaction conditions. Examples of inert substituents are CN, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl and Ci-C4-alkoxy-Ci-C6-alkyl;

[0057] Halo-heterocycloalkyl and also the halo-cycloalkyl moiety in halo-cycloalkoxy, halo-cycloalkylcarbonyl and the like: a monocyclic saturated hydrocarbon radical having 3 to 10 carbon ring members (as mentioned above), in which some or all of the hydrogen atoms can be replaced by halogen atoms mentioned above, in particular fluorine, chlorine and bromine;

[0058] Cycloalkoxy: cycloalkyl (as mentioned above) which is attached via an oxygen;

[0059] Alkoxy and also the alkoxy moiety in complex radicals, such as alkoxyalkyl: an alkyl radical (as defined above) which is attached via an oxygen, preferably having 1 to 10, more preferably 2 to 6 carbon atoms. Examples are methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1,1 -dimethylethoxy, and also, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1 -dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexyloxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1 -dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy;

[0060] haloalkoxy: alkoxy as defined above, wherein some or all of the hydrogen atoms in these groups are replaced by the mentioned halogen atoms, in particular fluorine, chlorine or bromine. Examples are OCH2F, OCHF2, OCF3, OCH2C1, OCHC12, OCC13, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2C1)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy or dodecafluorohexyloxy;

[0061] hydroxyl: an OH group which is attached via an O atom;

[0062] cyano: a CN group which is attached via a C atom;

[0063] nitro: an NO2 group which is attached via an N atom.

[0064] The preferred embodiments according to the application described hereinafter are to be understood as being preferred independently of one another or in combination.

[0065] According to a particular embodiment of the application, those compounds of the formula (I) are also preferred, wherein the variables, independently of one another or in combination, have the following meanings:

[0066] According to preferred compounds of the application are compounds of the formula (I), wherein R 1 selected from hydrogen, Ci-C3-alkyl, C3-C4-cycloalkyl, Ci-C3-haloalkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy-Ci-C3-alkyl, Ci-C3-alkoxy. According to preferred compounds of the application are also compounds of the formula (I), wherein R 1 selected from hydrogen, Ci-C3-alkyl, C3-C4-cycloalkyl and Ci-C3-haloalkyl, in particular hydrogen, methyl, cyclopropyl and 2,2-difluoroethyl.

[0067] More preferred compounds according to the application are compounds of formula (I), wherein R 1 is selected from hydrogen, C1-C3alkyl, C3-C4cycloalkyl and C1-C3alkoxy-C1-C3alkyl.

[0068] Further preferred compounds according to the application are compounds of formula (I), wherein R 1 is selected from hydrogen, methyl and methoxymethyl.

[0069] In particular, R 1 is hydrogen.

[0070] Further preferred compounds according to the application are compounds of formula (I), wherein R 2 is selected from hydrogen, halogen and C1-C3alkyl.

[0071] Preferred compounds according to the application are also compounds of formula (I), wherein R 2 is selected from hydrogen, halogen and C1-C3alkoxy, in particular hydrogen, fluorine and methoxy.

[0072] Further preferred compounds according to the application are compounds of formula (I), wherein R 2 is selected from hydrogen, fluorine, chlorine and methyl.

[0073] In particular, R 2 is hydrogen.

[0074] Further preferred compounds according to the application are compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, hydroxy, cyano and C1-C3alkyl.

[0075] Preferred compounds according to the application are also compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, hydroxy, cyano and C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy.

[0076] More preferred compounds according to the application are compounds of formula (I), wherein R 3 is selected from halogen, cyano and C1-C3alkyl.

[0077] Preferred compounds according to the application are also compounds of formula (I), wherein R 3 is selected from halogen, cyano and C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy.

[0078] Further preferred compounds according to the application are compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, cyano and methyl.

[0079] Preferred compounds according to the application are compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, cyano and methyl, C1-C3haloalkoxy, in particular hydrogen, halogen, trifluoromethoxy.

[0080] Preferred compounds according to the application are compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, hydroxy, cyano and methyl.

[0081] In particular, R 3 is hydrogen or halogen, very particularly chlorine or fluorine.

[0082] Further preferred compounds according to the application are compounds of formula (I), wherein R 4 is selected from hydrogen, halogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio and C1-C3haloalkylthio.

[0083] Further preferred compounds according to the application are compounds of formula (I), wherein R 4 is selected from hydrogen and halogen.

[0084] Preferred compounds according to the application are compounds of formula (I), wherein R 4 is selected from hydrogen, fluorine, chlorine and bromine.

[0085] In particular, R 4 is hydrogen or hydrogen, fluorine or chlorine, very particularly hydrogen.

[0086] Further preferred compounds according to the application are compounds of formula (I), wherein R 5 is selected from hydrogen, halogen, hydroxy, cyano and C1-C3alkyl.

[0087] Preferred compounds according to the application are compounds of formula (I), wherein R 5 is selected from hydrogen, halogen, hydroxy, cyano and C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy.

[0088] More preferred compounds according to the application are compounds of formula (I), wherein R 5 is selected from halogen, cyano and C1-C3alkyl.

[0089] Preferred compounds according to the application are compounds of formula (I), wherein R 5 is selected from halogen, cyano and C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy.

[0090] Preferred compounds according to the application are compounds of formula (I), wherein R 5selected from hydrogen, halogen, cyano and methyl.

[0091] Further preferred compounds according to the application are compounds of formula (I), wherein R 5 selected from hydrogen, halogen, cyano and methyl, Ci-C3haloalkoxy, in particular hydrogen, halogen, trifluoromethoxy.

[0092] Further preferred compounds according to the application are compounds of formula (I), wherein R 5 selected from hydrogen, halogen, hydroxy, cyano and methyl.

[0093] In particular, R 5 is hydrogen or halogen, very particularly chlorine or fluorine.

[0094] Further preferred compounds according to the application are compounds of formula (I), wherein R 6 selected from hydrogen, halogen and Ci-C3alkyl.

[0095] Preferred compounds according to the application are also compounds of formula (I), wherein R 6 selected from hydrogen, halogen and Ci-C3alkoxy, in particular hydrogen, fluorine and methoxy.

[0096] Further preferred compounds according to the application are compounds of formula (I), wherein R 6 selected from hydrogen, fluorine, chlorine and methyl.

[0097] In particular, R 6 is hydrogen.

[0098] Further preferred compounds according to the application are compounds of formula (I), wherein R 7 selected from Ci-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl and Ci-C3alkoxy-Ci-C3alkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano.

[0099] Further preferred compounds according to the application are compounds of formula (I), wherein R 7 selected from Ci-C6alkyl, Ci-C6haloalkyl, C3-C6cycloalkyl and C3-C6alkynyl.

[0100] Further preferred compounds according to the application are compounds of formula (I), wherein R 7 selected from Ci-C6alkyl, C3-C6cycloalkyl and C3-C6alkenyl.

[0101] Further preferred compounds according to the application are compounds of formula (I), wherein R 7 selected from Ci-C6alkyl.

[0102] In particular, R 7is methyl or ethyl, very particularly methyl.

[0103] Further preferred compounds according to the application are compounds of formula (I), wherein R 8 is selected from hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy and C3-C6-alkynyloxy.

[0104] Further preferred compounds according to the application are compounds of formula (I), wherein R 8 is selected from hydrogen, halogen, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy and C3-C6-alkynyloxy.

[0105] Further preferred compounds according to the application are compounds of formula (I), wherein R 8 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, C3-C6-cycloalkyl and Ci-C6-alkoxy.

[0106] More preferred compounds according to the application are compounds of formula (I), wherein R 8 is selected from hydrogen and halogen.

[0107] In particular, R 8 is hydrogen, fluorine, methyl, ethyl, methoxy or ethoxy, very particularly hydrogen or fluorine, most particularly hydrogen.

[0108] Further preferred compounds according to the application are compounds of formula (I), wherein R 9 is selected from hydrogen, Ci-C6-alkyl and C3-C6-cycloalkyl.

[0109] Further preferred compounds according to the application are compounds of formula (I), wherein R 9 is selected from hydrogen and Ci-C3-alkyl.

[0110] In particular, R 9 is hydrogen, methyl or ethyl, very particularly hydrogen.

[0111] In the compounds of formula (I), X is selected from a bond (X 0 ) or from a bivalent unit selected from (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ), wherein (X 1 ), (X 2 ), (X 3 ), (X4 ), (X 5 ), and (X 6 ) are oriented as shown, with the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y.

[0112]

[0113] In a preferred embodiment (compound of formula (I.X 0 ) is a bond (X 0 ):

[0114]

[0115] In another preferred embodiment (compound of formula (I.X 1 ) is (X 1 ), wherein (X 1 ) is oriented as shown, with the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0116]

[0117] In another preferred embodiment (compound of formula (I.X 2 ) is (X 2 ), wherein (X 2 ) is oriented as shown, with the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0118]

[0119] In another preferred embodiment (compound of formula (I.X 3 ) is (X 3 ), wherein (X 3 ) is oriented as shown, with the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0120]

[0121] In another preferred embodiment (compound of formula (I.X 4 ) is (X 4 ), wherein (X 4 ) is oriented as shown, with the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0122]

[0123] In another preferred embodiment (compound of formula (I.X 5 ) is (X5 ), wherein the orientation of (X 5 ) within the molecule is as shown, the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0124]

[0125] In another preferred embodiment (compounds of formula (I.X 6 ) wherein X is (X 6 ), wherein the orientation of (X 6 ) within the molecule is as shown, the left arrow indicating the bond to the adjacent nitrogen and the right arrow indicating the bond to the adjacent group Y:

[0126]

[0127] Further preferred compounds according to the application are compounds of formula (I), wherein X is selected from a bond (X 0 ) or from the group consisting of CH2, CH2CH2, CHCH3, CH2CH2CH2, CH(CH2CH3), CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C(iPr)CH3, CH(CH2iPr)CH2, CH2CH=CH, C(CH3)2C≡C, CH(CF3)CH2, CH(CH3)CH2O, CH2CH2O, CH(cPr)CH2O, CH(CH2OCH3), CH(CH2CH2SCH3), CH(COOH), CH(COOCH3), CH(COOH)CH2, CH(COOCH3)CH2, CH2COH(CF3), CH(CONHCH3), CH(CONHCH3)CH2and CH2CH2CONHCH2.

[0128] Further preferred compounds according to the application are compounds of formula (I), wherein R 10 -R 15 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e , CONR b R d or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, each substituted by m radicals selected from the group consisting of fluorine or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio, each substituted by m radicals selected from fluorine.

[0129] Further preferred compounds according to the application are compounds of formula (I), wherein R 10 -R 15each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e , CONR b R d or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, each substituted by m radicals selected from the group consisting of fluorine or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each substituted by m radicals selected from the group consisting of fluorine.

[0130] Further preferred compounds according to the application are compounds of formula (I), wherein Y is selected from the group consisting of hydrogen, cyano, hydroxyl, Z, or C1-C 10 -R 15 each independently selected from the group consisting of hydrogen, fluorine, chlorine, CO2R e , CONR b R d or C1-C6 alkyl, substituted by m radicals selected from the group consisting of fluorine or C1-C6 alkoxy, substituted by m radicals selected from the group consisting of fluorine or C1-C6 alkoxy.

[0131] In particular, R 10 -R 15 each independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C3 alkoxy and CO2R e .

[0132] Further preferred compounds according to the application are compounds of formula (I), wherein Y is selected from the group consisting of hydrogen, cyano, hydroxyl, Z, or C1-C 12 alkyl, C3-C8 cycloalkyl, C2-C 12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO2R e and CONR b R h .

[0133] Further preferred compounds according to the application are compounds of formula (I), wherein Y is selected from the group consisting of hydrogen, cyano, hydroxyl, Z, or C1-C 12 alkyl and C3-C8 cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, CO2R e and CONR b R h .

[0134] Further preferred compounds according to the application are compounds of formula (I), wherein Y is selected from the group consisting of C1-C 12 alkyl, C3-C8 cycloalkyl, C2-C 12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, ORd Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R b )=NOR e .

[0135] Preferred compounds according to the application are compounds of formula (I), wherein Y is selected from the group consisting of C1-C 12 alkyl, C3-C8cycloalkyl, C2-C 12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals selected from the group consisting of fluorine and CO2R e .

[0136] In particular, Y is selected from the group consisting of Z, or C1-C 12 alkyl and C3-C8cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, C1-C2alkoxy, CO2R e and CONR b R h .

[0137] According to a preferred embodiment, Y is Z.

[0138] Preferred compounds according to the application are compounds of formula (I), wherein Z is selected from a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms and n oxygen atoms, each of which is substituted by m groups selected from the group consisting of CO2R e , CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , COR b , CONR e SO2R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO2R e , NR b SO2R e , NR b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e , R b , R c , R e and R f , and wherein the carbon atoms carry n oxo groups.

[0139] Preferred compounds according to the application are compounds of formula (I), wherein Z is selected from a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms and n oxygen atoms, each of which is substituted by m groups selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f , and wherein the carbon atoms carry n oxo groups.

[0140] Further preferred compounds according to the present invention are compounds of formula (I), wherein Z is selected from a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e 、CONR b R h 、CONR e SO2R a 、R b 、R c 、R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups.

[0141] Further preferred compounds according to the present invention are compounds of formula (I), wherein Z is selected from a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e 、CONR b R h 、R b 、R c 、R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups.

[0142] Representative examples of the above-mentioned 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0143]

[0144] Representative examples of the above-mentioned 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0145]

[0146] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 4- or 5-membered saturated or partially unsaturated ring formed by r carbon atoms and n oxygen atoms, each substituted by m groups selected from the group consisting of: CO2R e 、CONR b R h 、CONR e SO2R a 、R b 、R c 、R e and R f .

[0147] Preferred compounds according to the application are compounds of formula (I), wherein Z is selected from a 4- or 5-membered saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, each of which is substituted by m groups selected from the group consisting of CO2R e , CONR b R h , CONR b SO2R c , R e , R f .

[0148] Preferred compounds according to the application are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the group consisting of CO2R e , CONR b R h , CONR e SO2R a , R b , R c , R e and R f .

[0149] Preferred compounds according to the application are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f .

[0150] Representative examples of 5-membered saturated or partially unsaturated rings, formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the group consisting of the above-mentioned CO2R e , CONR b R h , CONR e SO2R a , R b , R c , R e and R f , are of the following structure, the arrow indicating the bond to any of the above-mentioned substituents:

[0151]

[0152] Preferred examples of 5-membered saturated or partially unsaturated rings, formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the group consisting of the above-mentioned CO2R e , CONRb R h , CONR e SO2R a , R b , R c , R e and R f are of the following structure, the arrow indicating the bond to any of the above substituents, preferably to CO2R e :

[0153]

[0154] Preferred examples of 5-membered saturated or partially unsaturated rings are formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m radicals selected from the above-mentioned CO2R e , CONR b R h , R b , R c , R e and R f are of the following structure, the arrow indicating the bond to any of the above substituents, preferably to CO2R e :

[0155]

[0156] Preferred compounds according to the application are compounds of the formula (I), in which Z is selected from 5-membered saturated or partially unsaturated rings, formed by 5 carbon atoms, each of which is substituted by m radicals selected from CO2R e , CONR b R h , CONR e SO2R a , R b , R c , R e and R f .

[0157] Preferred compounds according to the application are compounds of the formula (I), in which Z is selected from 5-membered saturated or partially unsaturated rings, formed by 5 carbon atoms, each of which is substituted by m radicals selected from CO2R e , CONR b R h , R b , R c , R e and R f .

[0158] 5-membered saturated or partially unsaturated rings, formed by 5 carbon atoms, each of which is substituted by m radicals selected from the above-mentioned CO2R e , CONR bR h 、CONR e SO2R a 、R b 、R c 、R e and R f , is the following structure, with arrows indicating bonds to any of the above substituents:

[0159]

[0160] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 5 carbon atoms, each of which is substituted by m groups selected from the following groups: e 、CONR b R h 、CONR e SO2R a 、R b 、R c 、R e and R f , is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0161]

[0162] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 5 carbon atoms, each of which is substituted by m groups selected from the following groups: e 、CONR b R h 、R b 、R c 、R e and R f , is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0163]

[0164] In particular, Z is selected from cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each substituted by m groups selected from: CO2R e 、CONR b R h 、CONR e SO2R a 、R b 、R c 、R e and R f .

[0165] Very particularly, Z is selected from the group consisting of cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f .

[0166] Preferred examples of Z.1 to Z.5, each substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , CONR e SO2R a , R b , R c , R e and R f are of the following structure, the arrow (1) indicating the position of the bond to X, the arrows (2) and (3) pointing to the bonds to any of the mentioned substituents, in particular to CO2R e , CONR b R h , R b , R c , R e and R f :

[0167]

[0168] Preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning: R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3halogenalkyl, C2-C3alkenyl, C2-C3halogenalkenyl, C2-C3alkynyl, C2-C3halogenalkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0169] R 2 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0170] R 3hydrogen, halogen, nitro, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, hydroxy-Ci-C3-alkyl, C3-C5-cycloalkyl, C3-C5-halocycloalkyl, hydroxy-C3-C5-cycloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxycarbonyl, C2-C3-haloalkenyl, C2-C3-haloalkynyl, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl;

[0171] R 4 hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C4-halocycloalkyl, Ci-C3-haloalkoxy, C2-C3-haloalkenyl, C2-C3-haloalkynyl;

[0172] R 5 hydrogen, halogen, nitro, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, hydroxy-Ci-C3-alkyl, C3-C5-cycloalkyl, C3-C5-halocycloalkyl, hydroxy-C3-C5-cycloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxycarbonyl, C2-C3-haloalkenyl, C2-C3-haloalkynyl, Ci-C3-alkylthio, Ci-C3-alkylsulfinyl, Ci-C3-alkylsulfonyl;

[0173] R 6 hydrogen, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy;

[0174] R 7 Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, Ci-C3-alkoxy-Ci-C3-alkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;

[0175] R 8 hydrogen, halogen, cyano, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-cyanoalkyl, Ci-C3-hydroxyalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, Ci-C3-haloalkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-haloalkoxy, Ci-C3-cyanoalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, C3-C5-cycloalkyl-Ci-C3-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C3-alkylthio;

[0176] R 9hydrogen, Ci-C6-alkyl, C3-C4-cycloalkyl, Ci-C6-haloalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy;

[0177] X is a bond (X 0 ) or a bivalent unit selected from the group consisting of (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0178]

[0179] R 10 -R 15 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e , CONR b R d , R a , or Ci-C6-alkyl, C3-C5-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenoxy or C3-C6-alkynoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and Ci-C2-alkoxy;

[0180] Y is hydrogen, cyano, hydroxyl, Z, or Ci-C 12 alkyl, C3-C8-cycloalkyl, C2-C 12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e , CONR b R h , COR b , CONR e SO2R a , NR b R e , NRb COR e , NR b CONR e R e , NR b CO2R e , NR b SO2R e NR b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e ;

[0181] Z 3, 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f , and wherein the sulfur atoms and carbon atoms carry n oxo groups;

[0182] R a C1-C6alkyl or C3-C6cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0183] R b hydrogen or R a ;

[0184] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0185] R d hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, phenyl-C1-C3alkyl or C2-C4alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0186] Re R d ;

[0187] R f C1-C3alkyl or C1-C3alkoxy;

[0188] R h hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C1-C6alkoxycarbonyl-C1-C6alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0189] m 0, 1, 2, 3, 4 or 5;

[0190] n 0, 1 or 2;

[0191] r 1, 2, 3, 4, 5 or 6.

[0192] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0193] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, preferably hydrogen, C1-C3alkyl or C3-C4cycloalkyl, more preferably hydrogen;

[0194] R 2 hydrogen;

[0195] R 3 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0196] R 4 hydrogen or fluorine, preferably hydrogen;

[0197] R 5 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0198] R 6 hydrogen;

[0199] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0200] R 8 hydrogen or halogen, preferably hydrogen;

[0201] R 9 hydrogen;

[0202] X is a bond;

[0203] Y Z;

[0204] Z 3, 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and substituted by m groups selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f and wherein the sulfur atoms and the carbon atoms carry n oxo groups;

[0205] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0206] R b hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0207] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0208] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0209] R f C1-C3 alkyl or C1-C3 alkoxy;

[0210] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0211] r 1, 2, 3, 4, 5 or 6;

[0212] n 0, 1 or 2;

[0213] m 0, 1, 2, 3, 4 or 5.

[0214] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0215] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, preferably hydrogen, C1-C3alkyl or C3-C4cycloalkyl, more preferably hydrogen;

[0216] R 2 hydrogen;

[0217] R 3 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0218] R 4 hydrogen or fluorine, preferably hydrogen;

[0219] R 5 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0220] R 6 hydrogen;

[0221] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0222] R 8 hydrogen or halogen, preferably hydrogen;

[0223] R 9 hydrogen;

[0224] X is a bond;

[0225] Y Z;

[0226] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, completely unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and is substituted by m radicals selected from the group consisting of CO2R e and wherein the sulfur atoms and carbon atoms carry n oxo groups;

[0227] R e hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C3-C4alkenyl, phenyl-C1-C3alkyl or C3-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0228] r is 1, 2, 3, 4, 5 or 6;

[0229] n is 0, 1 or 2;

[0230] m 0, 1, 2, 3, 4 or 5.

[0231] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0232] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, preferably hydrogen, C1-C3alkyl or C3-C4cycloalkyl, more preferably hydrogen;

[0233] R 2 hydrogen;

[0234] R 3 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0235] R 4 hydrogen or fluorine, preferably hydrogen;

[0236] R 5 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0237] R 6 hydrogen;

[0238] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0239] R 8 hydrogen or halogen, preferably hydrogen;

[0240] R 9 hydrogen;

[0241] X is a bond;

[0242] Y Z;

[0243] Z 5-membered saturated, partially unsaturated or fully unsaturated carbocyclic ring, which is substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f ;

[0244] R a C1-C6alkyl or C3-C6cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0245] Rb hydrogen, Ci-C6-alkyl or C3-C6-cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0246] R c fluorine, chlorine, bromine, iodine, cyano, hydroxy, S(O) n R a or Ci-C6-alkoxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and Ci-C2-alkoxy;

[0247] R e hydrogen or Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl-Ci-C3-alkyl or C2-C4-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and Ci-C2-alkoxy;

[0248] R f Ci-C3-alkyl or Ci-C3-alkoxy;

[0249] R h hydrogen or Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, Ci-C6-alkyloxycarbonyl-Ci-C6-alkyl or C2-C4-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and Ci-C2-alkoxy;

[0250] m 0, 1, 2 or 3.

[0251] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0252] R 1 hydrogen, Ci-C3-alkyl, C3-C4-cycloalkyl, Ci-C3-haloalkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy-Ci-C3-alkyl, Ci-C3-alkoxy, preferably hydrogen, Ci-C3-alkyl or C3-C4-cycloalkyl, more preferably hydrogen;

[0253] R 2 hydrogen;

[0254] R 3 halogen, cyano, Ci-C3-alkyl, preferably fluorine or chlorine;

[0255] R 4 hydrogen or fluorine, preferably hydrogen;

[0256] R 5 halogen, cyano, Ci-C3-alkyl, preferably fluorine or chlorine;

[0257] R 6hydrogen;

[0258] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0259] R 8 hydrogen or halogen, preferably hydrogen;

[0260] R 9 hydrogen;

[0261] X is a bond;

[0262] Y is Z;

[0263] Z is a 5-membered saturated, partially unsaturated or fully unsaturated carbocyclic ring, which is substituted by m radicals selected from the group consisting of CO2R e and R b ;

[0264] R b hydrogen or C1-C6alkyl or C3-C6cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0265] R e hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C3-C4alkenyl, phenyl-C1-C3alkyl or C3-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0266] m is 0, 1 or 2.

[0267] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0268] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, preferably hydrogen, C1-C3alkyl or C3-C4cycloalkyl, more preferably hydrogen;

[0269] R 2 hydrogen;

[0270] R 3 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0271] R 4 hydrogen or fluorine, preferably hydrogen;

[0272] R 5 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0273] R6 hydrogen;

[0274] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0275] R 8 hydrogen or halogen, preferably hydrogen;

[0276] R 9 hydrogen;

[0277] X bond;

[0278] Y C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl or C2-C8alkynyl, each substituted by m radicals selected from the group consisting of fluorine and CO2R e ;

[0279] R e hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, phenyl-C1-C3alkyl or C2-C4alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0280] m 0, 1 or 2.

[0281] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0282] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, preferably hydrogen, C1-C3alkyl or C3-C4cycloalkyl, more preferably hydrogen;

[0283] R 2 hydrogen;

[0284] R 3 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0285] R 4 hydrogen or fluorine, preferably hydrogen;

[0286] R 5 halogen, cyano, C1-C3alkyl, preferably fluorine or chlorine;

[0287] R 6 hydrogen;

[0288] R 7 C1-C6alkyl, C3-C6cycloalkyl, preferably C1-C6alkyl, more preferably methyl;

[0289] R 8 hydrogen or halogen, preferably hydrogen;

[0290] R 9 hydrogen;

[0291] X bond;

[0292] Y C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl or C2-C8alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e , CONR b R h , COR b , CONR e SO2R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO2R e , NR b SO2R e NR b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e ;

[0293] Z 3-, 4-, 5- or 6-membered saturated, partially unsaturated, completely unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R fand wherein the sulfur atom and the carbon atom carry n oxo groups;

[0294] R a C1-C6alkyl or C3-C6cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0295] R b hydrogen, C1-C6alkyl or C3-C6cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0296] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6alkoxy, C3-C6alkenyloxy or C3-C6alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0297] R d hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, phenyl-C1-C3alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0298] R e hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, phenyl-C1-C3alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0299] R f C1-C3alkyl or C1-C3alkoxy;

[0300] R h hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C1-C6alkoxycarbonyl-C1-C6alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0301] r 1, 2, 3, 4, 5 or 6;

[0302] m 0, 1 or 2;

[0303] n 0, 1 or 2.

[0304] Further preferred compounds according to the application are compounds of formula (I), wherein the substituents have the following meanings:

[0305] R 1hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy;

[0306] R 2 hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy;

[0307] R 3 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3haloalkyl, C3-C5halocycloalkyl, C1-C3haloalkoxy, C2-C3haloalkenyl, C2-C3haloalkynyl;

[0308] R 4 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3haloalkyl, C3-C4halocycloalkyl, C1-C3haloalkoxy, C2-C3haloalkenyl, C2-C3haloalkynyl;

[0309] R 5 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3haloalkyl, C3-C5halocycloalkyl, C1-C3haloalkoxy, C2-C3haloalkenyl, C2-C3haloalkynyl;

[0310] R 6 hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy;

[0311] R 7 methyl;

[0312] R 8 hydrogen or fluorine;

[0313] R 9 hydrogen, C1-C6alkyl, C3-C4cycloalkyl, C1-C6haloalkyl, C1-C3alkoxy-C1-C3alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C3alkoxy-C1-C3alkoxy;

[0314] X is a bond (X 0 ) or a divalent unit selected from the group consisting of (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ), and (X6 ):

[0315]

[0316] R 10 -R 15 Each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e 、CONR b R d 、R a , or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano, or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0317] Y hydrogen, cyano, hydroxyl, Z, or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e 、CONR b R h 、COR b 、CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e 、OCONR b R e 、OCSNR b R e 、POR f Rf and C(R b ) = NOR e ;

[0318] Z 3, 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f and wherein the sulfur atoms and carbon atoms carry n oxo groups;

[0319] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0320] R b hydrogen or R a ;

[0321] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0322] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0323] R e R d ;

[0324] R f C1-C3 alkyl or C1-C3 alkoxy;

[0325] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0326] m 0, 1, 2, 3, 4 or 5;

[0327] n 0, 1 or 2;

[0328] r 1, 2, 3, 4, 5 or 6;

[0329] Further preferred compounds according to the application are compounds of formula (I), wherein each substituent has the following meaning:

[0330] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3halogenalkyl, C2-C3alkenyl, C2-C3halogenalkenyl, C2-C3alkynyl, C2-C3halogenalkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0331] R 2 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0332] R 3 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0333] R 4 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C4halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0334] R 5 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0335] R 6 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0336] R 7 methyl;

[0337] R 8 hydrogen or fluorine;

[0338] R 9hydrogen, C1-C6-alkyl, C3-C4-cycloalkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C3-alkoxy-C1-C3-alkoxy;

[0339] X is a bond;

[0340] Y is Z, or C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl or C2-C8-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and C1-C2-alkoxy; e and CONR e SO2R a ;

[0341] Z is a 4- to 5-membered saturated or partially unsaturated ring formed by r carbon atoms, n oxygen atoms and substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , CONR e SO2R a , R b , R c , R e and R f ;

[0342] R a C1-C6-alkyl or C3-C6-cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0343] R b hydrogen, or C1-C6-alkyl or C3-C6-cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0344] R c fluorine, chlorine, bromine, iodine, cyano, hydroxy, S(O) n R a or C1-C6-alkoxy, C3-C6-alkenoxy or C3-C6-alkynyloxy, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0345] R e hydrogen or C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl-C1-C3-alkyl or C2-C4-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0346] R fC1-C3alkyl or C1-C3alkoxy;

[0347] R h hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C1-C6alkoxycarbonyl-C1-C6alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0348] m 0, 1, 2, 3, 4 or 5;

[0349] n 0, 1 or 2;

[0350] r 1, 2, 3, 4 or 5.

[0351] Further preferred compounds according to the application are compounds of formula (I), wherein the substituents have the following meanings:

[0352] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3halogenalkyl, C2-C3alkenyl, C2-C3halogenalkenyl, C2-C3alkynyl, C2-C3halogenalkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0353] R 2 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0354] R 3 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogencycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0355] R 4 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C4halogencycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0356] R 5 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogencycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0357] R 6 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0358] R7 methyl;

[0359] R 8 hydrogen or fluorine;

[0360] R 9 hydrogen, Ci-C6-alkyl, C3-C4-cycloalkyl, Ci-C6-haloalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy;

[0361] X bond;

[0362] Y Z, or Ci-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl or C2-C8-alkynyl, each substituted by m radicals selected from the group consisting of fluorine and CO2R e ;

[0363] Z 4- to 5-membered saturated or partially unsaturated ring, which is formed from r carbon atoms and n oxygen atoms and is substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f ;

[0364] R a Ci-C6-alkyl or C3-C6-cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0365] R b hydrogen or Ci-C6-alkyl or C3-C6-cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0366] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or Ci-C6-alkoxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and Ci-C2-alkoxy;

[0367] R e hydrogen or Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl-Ci-C3-alkyl or C2-C4-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and Ci-C2-alkoxy;

[0368] R f C1-C3alkyl or C1-C3alkoxy;

[0369] R h hydrogen or C1-C6alkyl, C3-C6cycloalkyl, C2-C4alkenyl, C1-C6alkoxycarbonyl-C1-C6alkyl or C2-C4alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2alkoxy;

[0370] m 0, 1, 2, 3, 4 or 5;

[0371] n 0, 1 or 2;

[0372] r 1, 2, 3, 4 or 5.

[0373] Further preferred compounds according to the application are compounds of formula (I), wherein the substituents have the following meanings:

[0374] R 1 hydrogen, C1-C3alkyl, C3-C4cycloalkyl, C1-C3halogenalkyl, C2-C3alkenyl, C2-C3halogenalkenyl, C2-C3alkynyl, C2-C3halogenalkynyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0375] R 2 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0376] R 3 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0377] R 4 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C4halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0378] R 5 hydrogen, halogen, hydroxyl, cyano, C1-C3alkyl, C1-C3halogenalkyl, C3-C5halogen cycloalkyl, C1-C3halogenalkoxy, C2-C3halogenalkenyl, C2-C3halogenalkynyl;

[0379] R 6 hydrogen, halogen, C1-C3alkyl, C1-C3halogenalkyl, C1-C3alkoxy, C1-C3halogenalkoxy;

[0380] R 7 C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C3alkoxy-C1-C3alkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;

[0381] R 8 hydrogen, halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6cyanoalkyl, C1-C3hydroxyalkyl, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, C3-C6cycloalkoxy, C1-C6haloalkoxy, C1-C3cyanoalkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C5cycloalkyl-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C3alkylthio;

[0382] R 9 hydrogen, C1-C6alkyl, C3-C4cycloalkyl, C1-C6haloalkyl, C1-C3alkoxy-C1-C3alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C3alkoxy-C1-C3alkoxy;

[0383] X a bond;

[0384] Y Z;

[0385] Z a 4- to 5-membered saturated or partially unsaturated ring, which is formed by r carbon atoms, n oxygen atoms and is substituted by m radicals selected from the group consisting of CO2R e , CONR b R h , R b , R c , R e and R f ;

[0386] R a C1-C6alkyl or C3-C6cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0387] R b hydrogen or C1-C6alkyl or C3-C6cycloalkyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0388] R cfluorine, chlorine, bromine, iodine, cyano, hydroxy, S(O) n R a or C1-C6-alkoxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0389] R e hydrogen or C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl-C1-C3-alkyl or C2-C4-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0390] R f C1-C3-alkyl or C1-C3-alkoxy;

[0391] R h hydrogen or C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl or C2-C4-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0392] m 0, 1, 2, 3, 4 or 5;

[0393] n 0, 1 or 2;

[0394] r 1, 2, 3, 4 or 5.

[0395] Further preferred compounds according to the application are compounds of formula (I), wherein the substituents have the following meanings:

[0396] R 1 hydrogen, C1-C3-alkyl, C3-C4-cycloalkyl, C1-C3-haloalkyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C2-C3-haloalkynyl, C1-C3-alkoxy-C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkoxy;

[0397] R 2 hydrogen, halogen, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy;

[0398] R 3 hydrogen, halogen, hydroxy, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C3-C5-halocycloalkyl, C1-C3-haloalkoxy, C2-C3-haloalkenyl, C2-C3-haloalkynyl;

[0399] R 4hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C4-halocycloalkyl, Ci-C3-haloalkoxy, C2-C3-haloalkenyl, C2-C3-haloalkynyl;

[0400] R 5 hydrogen, halogen, hydroxyl, cyano, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C4-halocycloalkyl, Ci-C3-haloalkoxy, C2-C3-haloalkenyl, C2-C3-haloalkynyl;

[0401] R 6 hydrogen, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy;

[0402] R 7 Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, Ci-C3-alkoxy-Ci-C3-alkyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;

[0403] R 8 hydrogen, halogen, cyano, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-cyanoalkyl, Ci-C3-hydroxyalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, Ci-C3-haloalkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-haloalkoxy, Ci-C3-cyanoalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy, C3-C5-cycloalkyl-Ci-C3-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C3-alkylthio;

[0404] R 9 hydrogen, Ci-C6-alkyl, C3-C4-cycloalkyl, Ci-C6-haloalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkoxy;

[0405] X is a bond;

[0406] Y is Ci-C 12 alkyl, C3-C8-cycloalkyl, C2-C 12 alkenyl or C2-C 12 alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) nR a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R b )=NOR e ;

[0407] Z 3, 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of CO2R e CONR b R h R b R c R e and R f and wherein the sulfur atoms and carbon atoms carry n oxo groups;

[0408] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0409] R b hydrogen or R a ;

[0410] R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R aor C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0411] R d hydrogen or C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0412] R e R d ;

[0413] R f C1-C3-alkyl or C1-C3-alkoxy;

[0414] R h hydrogen or C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl or C2-C4-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2-alkoxy;

[0415] m 0, 1, 2, 3, 4 or 5;

[0416] n 0, 1 or 2;

[0417] r 1, 2, 3, 4, 5 or 6.

[0418] Further preferred embodiments (I.I - I.IV) of the compounds of formula (I) are the following compounds, wherein (I.I): 1 , R 9 is hydrogen:

[0419]

[0420] (I.II): R 1 is hydrogen, R 9 is methyl:

[0421]

[0422] (I.III): R 1 is methyl, R 9 is methyl:

[0423]

[0424] (I.IV): R 1 is methyl, R 9 is hydrogen:

[0425]

[0426] Particularly preferred are compounds of formula (I.I.a.) wherein R 1 , R 2 , R 6 and R 9 are hydrogen:

[0427]

[0428] Also particularly preferred are compounds of formula (I.I.b.) wherein R 1 , R 2 , R 4 , R 6 and R 9 are hydrogen:

[0429]

[0430] Particularly preferred are compounds of formula (I.I.c.) wherein R 1 , R 2 , R 6 and R 9 are hydrogen, X is a bond (X 0 ) and Y is Z:

[0431]

[0432] Also particularly preferred are compounds of formula (I.I.d.) wherein R 1 , R 2 , R 4 , R 6 and R 9 are hydrogen, X is a bond (X 0 ) and Y is Z:

[0433]

[0434] Also particularly preferred are compounds of formula (I.II.a.) wherein R 1 , R 2 , R 6 are hydrogen and R 9 is methyl:

[0435]

[0436] Also particularly preferred are compounds of formula (I.II.b.) wherein R 1 , R 2 , R 4 , R 6 are hydrogen and R 9 is methyl:

[0437]

[0438] Also particularly preferred are compounds of formula (I.III.a.) wherein R 2 , R 6 is hydrogen and R 1 , R 9 is methyl:

[0439]

[0440] Also particularly preferred are compounds of formula (I.III.b.) wherein R 2 , R 4 , R 6 is hydrogen and R 1 , R 9 is methyl:

[0441]

[0442] Also particularly preferred are compounds of formula (I.IV.a.) wherein R 1 is methyl and R 2 , R 6 and R 9 is hydrogen:

[0443]

[0444] Also particularly preferred are compounds of formula (I.IV.b.) wherein R 1 is methyl and R 2 , R 4 , R 6 and R 9 is hydrogen:

[0445]

[0446] In the context of the present application, particularly preferred are compounds wherein R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 below: Table 1:

[0447] In Table 1, means cyclopropyl.

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465] Particularly preferred are compounds of formula I.1., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.1.1 to I.1.1152:

[0466]

[0467] Particularly preferred are compounds of formula I.2., in which R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.2.1 - I.2.1152:

[0468]

[0469] Particularly preferred are compounds of formula I.3., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.3.1 - I.3.1152:

[0470]

[0471] Particularly preferred are compounds of formula I.4., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.4.1 - I.4.1152:

[0472]

[0473] Particularly preferred are compounds of formula I.5., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.5.1 - I.5.1152:

[0474]

[0475] Particularly preferred are compounds of formula I.6., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R7 R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.6.1 - I.6.1152:

[0476]

[0477] Particular preference is given to compounds of the formula I.7., wherein R 1 R 2 R 6 and R 9 are hydrogen and R 3 R 4 R 5 and R 7 R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.7.1 - I.7.1152:

[0478]

[0479] Particular preference is given to compounds of the formula I.8., wherein R 1 R 2 R 6 and R 9 are hydrogen and R 3 R 4 R 5 and R 7 R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.8.1 - I.8.1152:

[0480]

[0481] Particular preference is given to compounds of the formula I.9., wherein R 1 R 2 R 6 and R 9 are hydrogen and R 3 R 4 R 5 and R 7 R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.9.1 - I.9.1152:

[0482]

[0483] Particular preference is given to compounds of the formula I.10., wherein R 1 R 2 R 6 and R 9 are hydrogen and R 3 R4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.10.1 to I.10.1152:

[0484]

[0485] Particularly preferred are compounds of formula I.11., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.11.1 to I.11.1152:

[0486]

[0487] Particularly preferred are compounds of formula I.12., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.12.1 to I.12.1152:

[0488]

[0489] Particularly preferred are compounds of formula I.13., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.13.1 to I.13.1152:

[0490]

[0491] Particularly preferred are compounds of formula I.14., wherein R 1 、R 2 、R6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.14.1 - I.14.1152:

[0492]

[0493] Particularly preferred are compounds of formula I.15. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.15.1 - I.15.1152:

[0494]

[0495] Particularly preferred are compounds of formula I.16. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.16.1 - I.16.1152:

[0496]

[0497] Particularly preferred are compounds of formula I.17. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.17.1 - I.17.1152:

[0498]

[0499] Particularly preferred are compounds of formula I.18. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.18.1 - I.18.1152:

[0500]

[0501] Particularly preferred are compounds of formula I.19. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.19.1 - I.19.1152:

[0502]

[0503] Particularly preferred are compounds of formula I.20. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.20.1 - I.20.1152:

[0504]

[0505] Particularly preferred are compounds of formula I.21. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.21.1 - I.21.1152:

[0506]

[0507] Particular preference is given to compounds of the formula I.22. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.22.1 - I.22.1152:

[0508]

[0509] Particular preference is given to compounds of the formula I.23. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.23.1 - I.23.1152:

[0510]

[0511] Particular preference is given to compounds of the formula I.24. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.24.1 - I.24.1152:

[0512]

[0513] Particular preference is given to compounds of the formula I.25. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.25.1 - I.25.1152:

[0514]

[0515] Particular preference is given to compounds of the formula I.26. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.26.1 - I.26.1152:

[0516]

[0517] Particular preference is given to compounds of the formula I.27. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.27.1 - I.27.1152:

[0518]

[0519] Particular preference is given to compounds of the formula I.28. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.28.1 - I.28.1152:

[0520]

[0521] Particular preference is given to compounds of the formula I.29. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.29.1 - I.29.1152:

[0522]

[0523] Particularly preferred are compounds of formula I.30. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.30.1 - I.30.1152:

[0524]

[0525] Particularly preferred are compounds of formula I.31. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.31.1 - I.31.1152:

[0526]

[0527] Particularly preferred are compounds of formula I.32. wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.32.1 - I.32.1152:

[0528]

[0529] Particularly preferred are compounds of formula I.33. wherein R 1 , R 2 , R 6 and R9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.33.1 to I.33.1152:

[0530]

[0531] Particularly preferred are compounds of formula I.34., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.34.1 to I.34.1152:

[0532]

[0533] Particularly preferred are compounds of formula I.35., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.35.1 to I.35.1152:

[0534]

[0535] Particularly preferred are compounds of formula I.36., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.36.1 to I.36.1152:

[0536]

[0537] Particularly preferred are compounds of formula I.37., wherein R1 2 6 9 3 4 5 7 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.37.1 - I.37.1152:

[0538]

[0539] Particular preference is given to compounds of the formula I.38. in which R 1 2 6 9 3 4 5 7 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.38.1 - I.38.1152:

[0540]

[0541] Particular preference is given to compounds of the formula I.39. in which R 1 2 6 9 3 4 5 7 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.39.1 - I.39.1152:

[0542]

[0543] Particular preference is given to compounds of the formula I.40. in which R 1 2 6 9 3 4 5 7 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.40.1 - I.40.1152:

[0544] ​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​

[0545] Particularly preferred are compounds of the formula I.41.1 - I.41.1152 in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.41.1 - I.41.1152:

[0546]

[0547] Particularly preferred are compounds of the formula I.42.1 - I.42.1152 in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.42.1 - I.42.1152:

[0548]

[0549] Particularly preferred are compounds of the formula I.43.1 - I.43.1152 in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.43.1 - I.43.1152:

[0550]

[0551] Particularly preferred are compounds of the formula I.44.1 - I.44.1152 in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.44.1 - I.44.1152:

[0552]

[0553] Particularly preferred are compounds of formula I.45., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.45.1 to I.45.1152:

[0554]

[0555] Particularly preferred are compounds of formula I.46., wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.46.1 to I.46.1152:

[0556]

[0557] Particularly preferred are compounds of formula I.47, wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8 have the meanings defined in rows 1 to 1152 of Table 1 above, i.e., respective compounds I.47.1 to I.47.1152:

[0558]

[0559] Particularly preferred are compounds of formula I.48, wherein R 1 、R 2 、R 6 and R 9 is hydrogen and R 3 、R 4 、R 5 and R 7 、R 8have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.48.1 - I.48.1152:

[0560]

[0561] Particular preference is given to compounds of the formula I.49. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.49.1 - I.49.1152:

[0562]

[0563] Particular preference is given to compounds of the formula I.50. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.50.1 - I.50.1152:

[0564]

[0565] Particular preference is given to compounds of the formula I.51. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.51.1 - I.51.1152:

[0566]

[0567] Particular preference is given to compounds of the formula I.52. in which R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.52.1 - I.52.1152:

[0568]

[0569] Particularly preferred are compounds of formula I.53., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.53.1 - I.53.1152:

[0570]

[0571] Particularly preferred are compounds of formula I.54., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.54.1 - I.54.1152:

[0572]

[0573] Particularly preferred are compounds of formula I.55., wherein R 1 , R 2 , R 6 and R 9 are hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings as defined in lines 1 to 1152 of Table 1 above, i.e. each compound I.55.1 - I.55.1152:

[0574]

[0575] Particularly preferred are compounds of formula I.56., wherein R 1 , R 2 , R 6 and R9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 have the meanings defined in lines 1 to 1152 of Table 1 above, i.e. each of the compounds I.56.1 - I.56.1152:

[0576]

[0577] The compounds of formula (I) according to the application can be prepared by standard methods of organic chemistry, for example by the following methods:

[0578]

[0579] The compounds of formula (I) can be prepared according to methods described in the prior art or analogously thereto. The synthesis makes use of starting materials which are either commercially available or can be prepared according to conventional procedures starting from readily available compounds.

[0580] The compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling agent. Thus, the compounds of formula (I) can be synthesized from the corresponding carboxylic acids (1 eq.) using a coupling agent (1-2 eq.) such as T3P (propane phosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), an organic base (1-3 eq.) and the amine (II) (1-3 eq.). The reaction is usually carried out in an organic solvent. It is preferred to use an aprotic organic solvent. It is most preferred to use tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN). The reaction is carried out at a temperature between 0 °C and reflux. It is preferred that the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[0581]

[0582] The carboxylic acids (III) can be commercially available or can be prepared from the corresponding esters (IV) (wherein R P is alkyl or benzyl). If R P is alkyl, the esters (IV) can be cleaved using aqueous alkali hydroxide. It is preferred to use lithium hydroxide, sodium hydroxide or potassium hydroxide (1-2 eq.). The reaction is usually carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol or acetonitrile. The reaction is carried out at a temperature between 0 °C and 100 °C. It is preferred that the reaction is carried out at room temperature. If R pis benzyl, the ester can be cleaved using palladium on charcoal (0.001 - 1 eq.) as catalyst and hydrogen gas at temperatures between 0 °C and reflux. Preferably the reaction is carried out at room temperature. Usually an organic solvent is used. Preferably THF, methanol or ethanol is used.

[0583]

[0584] The compound of formula (IV) can be prepared from the carboxylic acid (VI) and the commercially available amine (V) using a base and a coupling agent. Thus, the compound of formula (IV) can be synthesized from the corresponding carboxylic acid (1 eq.) using a coupling agent (1 - 2 eq.) such as T3P (propane phosphonic anhydride) or HATU (0-(7-azabenzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), an organic base (1 - 3 eq.) and the amine (V) (1 - 3 eq.). The reaction is usually carried out in an organic solvent. Preferably an aprotic organic solvent is used. Most preferably tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN) is used. The reaction is carried out at temperatures between 0 °C and reflux temperature. Preferably the reaction is carried out at room temperature. Preferably the organic base is triethylamine or N,N-diisopropylethylamine.

[0585]

[0586] The carboxylic acid (VI) can be prepared from the corresponding diester by selective cleavage of one ester group. If R q is an alkyl ester, the selective ester cleavage can be achieved using an aqueous base. Preferably an alkali hydroxide is used. Most preferably lithium hydroxide, sodium hydroxide or potassium hydroxide is used. The reaction is usually carried out in a mixture of water and an organic solvent. Preferably THF, methanol or acetonitrile is used. The reaction is carried out at temperatures between 0 °C and 100 °C, preferably at room temperature.

[0587] Alternatively, trimethyltin hydroxide (e.g. 1 eq.) in 1,2-dichloroethane at room temperature to reflux can be used (as described in Angew. Chem. Int. Ed, 2005, 44: 1378-1382), preferably at reflux. If R q is benzyl, the ester can be cleaved using palladium on charcoal (0.001 - 1 eq.) as catalyst and hydrogen gas at temperatures between 0 °C and reflux. Preferably the reaction is carried out at room temperature. Usually an organic solvent is used. Preferably THF, methanol or ethanol is used.

[0588]

[0589] The diester (VII) can be commercially available or can be prepared using dirhodium tetraacetate ([Rh(OAc)2]2) (0.001 - 0.1 eq.) and an alcohol HO-R 7from the corresponding diazo compound (VIII) to yield the alkoxy malonate (VII) (R 8 = H). The reaction is typically carried out in an organic solvent, preferably in toluene at temperatures between 0 and 100 °C. Preferably, the reaction is carried out at 60 °C as described in Angew. Chem. Int. Ed. 2014, 53, 14230-14234. The diazo compound (VIII) can be prepared as described in Angew. Chem. Int. Ed. 2014, 53, 14230-14234 if not commercially available.

[0590]

[0591] Alternatively, the diester (VII) can be synthesized from a commercially available monoester (XI), a base and a chloroformate (XII) (1-3 eq.) as described in Bioorganic & Medicinal Chemistry Letters, 12(11), 1501-1505; 2002. The reaction is typically carried out in an organic solvent, preferably in tetrahydrofuran. Suitable temperatures are between -78 °C and 25 °C. Preferably, the reaction is allowed to warm from -78 °C to 25 °C within 16 hours. Diisopropylaminolithium (1 eq.) is preferably used as base.

[0592] Alternatively, the diester (VII) wherein R 8 is fluorine can be prepared from the corresponding non-fluorinated malonate using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane di(tetrafluoroborate) (Selectfluor) as described in WO 12 / 129384. Water and / or an organic solvent is used. Preferably, the reaction is carried out in acetonitrile. The reaction is carried out at temperatures between 0 °C and reflux, preferably at 60 °C using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane di(tetrafluoroborate) (Selectfluor). Alternatively, N-fluorobenzenesulfonimide (CAS 133745-75-2) can be used (see e.g. Differding, E., & Ofner, H. (1991). N-Fluorobenzenesulfonimide: A practical reagent for electrophilic fluorinations. Synlett, 1991(03) 187-189).

[0593]

[0594] The amines of formula (XIII) can be prepared from lactam (XIV) (which is commercially available or can be prepared by an alkylation reaction as described in Org. Process Res. Dev. 2018, 22, 337-343) and commercially available alcohol (XV) using thionyl chloride (2 eq.) as described in Tetrahedron Lett. 2001, 42, 1347-1350. The reaction is usually carried out in the coupling alcohol (XV) as solvent. The reaction is carried out at a temperature between 0 °C and reflux temperature. Preferably the reaction is carried out at room temperature.

[0595] In order to broaden the spectrum of action, the compounds of the formula (I) can be mixed with many other groups of herbicidally or growth-regulatory active ingredients and then applied simultaneously. Suitable components for combinations are, for example, herbicides from the following groups: acetamides, amides, aryloxy- phenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridines carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isoxazoles isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxadiazoles, oxazolidinediones, oxoacetamides, phenoxy carboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, phthalamidic acids, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoic acids, quinolinecarboxylic acids, sulfilimines, sulfonamidocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, ureas.

[0596] Furthermore, it can be beneficial to apply the compounds of the formula (I) alone or in combination with other herbicides or in the form of mixtures with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. The miscibility with inorganic salt solutions for the treatment of deficiencies of nutrients and trace elements is also of interest. Further additives such as non-phytotoxic oils and oil concentrates can also be added.

[0597] In one embodiment of the present application, the combination according to the present application comprises at least one compound of the formula (I) (compound A or component A) and at least one further active compound selected from the group consisting of herbicides B (compound B), preferably herbicides B of groups b1 ) to b15), and safeners C (compound C).

[0598] In another embodiment of the present application, the combinations according to the present application comprise at least one compound of formula (I) and at least one further active compound B (herbicide B).

[0599] Examples of herbicides B which can be used in combination with the compounds of formula (I) according to the present application are:

[0600] b1 ) an inhibitor of the lipid biosynthesis selected from the group consisting of ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenthiaprop, fenthiaprop-Ethyl, fenoxaprop, fenoxaprop-Ethyl, fenthiaprop, fenthiaprop-Ethyl, fenoxaprop, fenoxaprop-Ethyl, fenthiaprop, fenthiaprop-Ethyl, fenoxaprop, fenoxaprop-Ethyl, fenthiaprop, fenthiaprop-Ethyl, fenoxaprop, fenoxaprop-Ethyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop- tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6- tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6), 4-(2',4'-dichloro-4- cyclopropyl[1,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3), 4-(4'-chloro-4-ethyl-2'-fluoro[1,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6- tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5), 4-(2',4'-dichloro-4-ethyl[1,1 '- biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5- acetyloxy-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (CAS 1312337-48-6), 5-acetyloxy-4-(2',4'-dichloro-4- cyclopropyl-[1,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5- acetyloxy-4-(4'-chloro-4-ethyl-2'-fluoro[1,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl- 2H-pyran-3-one (CAS 1312340-82-1 ), 5-acetyloxy-4-(2',4'-dichloro-4-ethyl[1,1 '-biphenyl]- 3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), 4-(4'-chloro-4-6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS 1312337-51-1), 4-(2',4'-dichloro-4-cyclopropyl-[1,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate, 4-(4'-chloro-4-ethyl-2'-fluoro[1,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS 1312340-83-2), 4-(2',4'-dichloro-4-ethyl[1,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

[0601] b2) an ALS inhibitor selected from the group consisting of sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, triflusulfuron, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triflusulfuron-methyl, triftrifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumets ulam), florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinyl benzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 1-methylethyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-41-6), propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8), sulfonylaminocarbonyltriazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone; among which preferred embodiments according to the present invention relate to those compositions comprising at least one imidazolinone herbicide;

[0602] b3) photosynthesis inhibitors selected from the group consisting of amicarbazone, inhibitors of photosystem II, for example 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisothiazolinone), oxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisothiazolinone 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisothiazolinone) oxazol-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including chlorotriazines, triazinones, triazinediones, methylthiotriazines and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, uzin), prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin; aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thidiazuron, phenylaminocarbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacil and terbacil, and also bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and photosystem I inhibitors such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Preferred embodiments according to the application are those compositions which comprise at least one arylurea herbicide. Preferred embodiments according to the application are likewise those compositions which comprise at least one triazine herbicide. Preferred embodiments according to the application are likewise those compositions which comprise at least one nitrile herbicide;

[0603] b4) a protoporphyrinogen-IX oxidase inhibitor selected from the group consisting of acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone, fluoroquinolone Flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, propargyl Oxadiargyl, oxadiazon, oxyfluorfen, ammonium Pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] oxazine-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] methyl 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4- fluorophenoxy] -2-methoxyacetate (CAS 1970221-16-9), methyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate (CAS 2158274-96-3), ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate (CAS 158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4- fluorophenoxy]-2-pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4- fluorophenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), methyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridyl]oxy]-2-pyridyl]oxy]acetate (CAS 2158275-73-9), ethyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridyl]oxy]-2-pyridyl]oxy]acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridyl]oxy]phenoxy]-N-(methylsulfonyl)acetamide (CAS 2158274-53-2), 2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);

[0604] b5) bleaching agent herbicides selected from the group consisting of PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoflurane, chlorpyrifos ... Isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleaching agents, unknown targets: aclonifen, amitrole, flumeturon, 2-chloro-3-methylthio-N-(1-methyltetrazol-5-yl)-4-trifluoromethylbenzamide (CAS 1361139-71-0), dichloroisothiazolinone Bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isothiazolinone Oxazolidinone (CAS 81778-66-7);

[0605] b6) EPSP synthase inhibitors selected from the group consisting of glyphosate, glyphosate-isopropylammonium, glyphosate potassium, and glyphosate-trimesium (sulfosate);

[0606] b7) an inhibitor of glutamine synthetase selected from the group consisting of bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium;

[0607] b8) an inhibitor of DHP synthetase selected from the group consisting of asulam;

[0608] b9) an inhibitor of mitosis selected from the group consisting of K1 compounds: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam, K2 compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; wherein K1 compounds are preferred, especially dinitroanilines;

[0609] b10) a VLCFA inhibitor selected from the group consisting of chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetamides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and further herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 isoxazoline compounds:

[0610]

[0611]

[0612] isoxazoline compounds of the formula (II) isoxazoline compounds are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0613] Among the VLCFA inhibitors, chloroacetamides and oxyacetamides are preferred;

[0614] b11 ) a cellulose biosynthesis inhibitor selected from the group consisting of chlorthiamid, dichlobenil, flupoxam, isoxaben, triaziflam and 1 -cyclohexyl-5- pentafluoro-phenoxy-1 H-1,2,4-triazole (CAS 175899-01 -1 ); 4 - [1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );

[0615] b12) an uncoupler herbicide selected from the group consisting of dinoseb, dinoterb and dinofenate (DNOC) and salts thereof;

[0616] b13) a plant growth regulator herbicide selected from the group consisting of 2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxy-propyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinoclamine, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)picolinic acid (CAS 1629965-65-6);

[0617] b14) a plant hormone transport inhibitor selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

[0618] b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, potassium cyanate, (pro)phenazine, quinoclamine, tetrafluron and tridiphane. oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetrafluron and tridiphane.

[0619] Furthermore, it can be useful to apply the compounds of formula (I) in combination with a safener. Safeners are compounds which prevent or reduce damage to useful plants but do not significantly influence the herbicidal action of the compounds of formula (I) on undesirable plants. They can be applied before sowing (for example at the time of seed treatment, on the seedling or on the seedling) or in the pre- or post-emergence manner of the useful plants. The safener and the compound of formula (I) and optionally the herbicide B can be applied simultaneously or sequentially.

[0620] In another embodiment of the present application, the combination of the present application comprises at least one compound of formula (I) and at least one safener C (component C).

[0621] Examples of safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isothiazolinone, Azolecarboxylic acid, dichloroacetamides, α-oximinophenylacetonitrile, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalene dicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acids, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and agriculturally acceptable derivatives thereof, such as amides, esters and thioesters, provided that they have an acid group.

[0622] Examples of safener compounds C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, diphenyl Isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3- Oxazolidine (R-29148, CAS 52836-31-4), metcamifen, and BPCMS (CAS 54091-06-4).

[0623] The active compounds B and C of groups b1 ) to b15) are known herbicides and safeners, for example see The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, 86th Edition, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995; W. H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994 and K. K. Hatzios, Herbicide Handbook, 7th Edition Supplement, Weed Science Society of America, 1998. 2,2,5-trimethyl-3-dichloroacetyl-1,3-oxazolidine [CAS No. 52836-31 -4] is also known as R-29148. 4-dichloroacetyl-1 -oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660. Azolidine [CAS No. 52836-31 -4] is also known as R-29148. 4-dichloroacetyl-1 -oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660.

[0624] The assignment of the respective mode of action of the active compounds is based on the current knowledge. If several modes of action apply to one active compound, the substance is assigned to only one mode of action.

[0625] The present application also relates to formulations comprising at least one auxiliary and at least one compound of the formula (I) of the present application.

[0626] The formulations comprise a pesticidally effective amount of the compound of the formula (I). The term "effective amount" denotes the quantity of the combination or of the compound of the formula (I) which is sufficient to control undesired plants, in particular in crops, i.e. in cultivated plants, and which does not result in significant damage to the treated crop plants. This quantity can vary within wide limits and depends on various factors, such as the undesired plants to be controlled, the crop plants or materials being treated, the climatic conditions and the specific compound of the formula (I) used.

[0627] The compounds of formula (I), salts, amides, esters or thioesters thereof can be converted into the types of formulations customary for such purposes, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules and mixtures thereof. Examples of formulation types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN) and gel formulations for the treatment of plant propagation materials, such as seeds (e.g. GF). These and other formulation types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph, 2nd Edition, May 2008, CropLife International.

[0628] Formulations are prepared in known manner, as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, AgrowReports DS243, T&F Informa, London, 2005.

[0629] Suitable adjuvants are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration promoters, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoams, colorants, tackifiers and binders.

[0630] Suitable solvents and liquid carriers are water and organic solvents such as mineral oil fractions of medium to high volatility, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

[0631] Suitable solid carriers or fillers are mineral earths, such as silicates, silica, talc, kaolin, limestone, lime, chalk, bole, dolomite, diatomite, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, such as corn, rice, soybean, tea and coffee grounds, tree bark, wood, nutshell meal, and mixtures thereof.

[0632] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifiers, dispersants, solubilizers, wetters, penetration promoters, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0633] Suitable anionic surfactants are alkali metal, alkaline earth metal or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, carboxylic acids, and mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkyl phenol sulfonates, alkoxylated aryl phenol sulfonates, condensed naphthalene sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are fatty acid and oil sulfates, ethoxylated alkyl phenol sulfates, alcohol sulfates, ethoxylated alcohol sulfates or fatty acid ester sulfates. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates as well as carboxylated alcohol or alkyl phenol ethoxylates.

[0634] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkyl phenols, amines, amides, aryl phenols, fatty acids or fatty esters which have been alkoxylated with 1 to 50 equivalents of alkylene oxide, preferably ethylene oxide. Ethylene oxide and / or propylene oxide can be used for the alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0635] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having 1 or 2 hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers comprising blocks of polyoxyethylene and polyoxypropylene, or A-B-C type block polymers comprising alkanol, polyoxyethylene and polyoxypropylene. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyvinyl amine.

[0636] Suitable adjuvants are compounds which have negligible or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and further adjuvants. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0637] Suitable thickeners are polysaccharides (such as xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0638] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzoisothiazolinones.

[0639] Suitable antifreezes are ethylene glycol, propylene glycol, urea and glycerol.

[0640] Suitable antifoams are polysiloxanes, long-chain alcohols and fatty acid salts.

[0641] Suitable colorants (for example in red, blue or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (for example iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (for example alizarin, azo and phthalocyanine colorants).

[0642] Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.

[0643] Examples of formulation types and their preparation are:

[0644] i) water-soluble concentrates (SL, LS)

[0645] 10 to 60% by weight of a compound of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) and 5 to 15% by weight of a wetter (e.g. alcohol alkoxylate) are dissolved in water and / or water-soluble solvents (e.g. alcohols) ad 100% by weight. The active substances are dissolved on dilution with water.

[0646] ii) dispersible concentrates (DC)

[0647] 5 to 25% by weight of a compound of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) and 1 to 10% by weight of a dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvents (e.g. cyclohexanone) ad 100% by weight. Dilution with water gives dispersions.

[0648] iii) emulsifiable concentrates (EC)

[0649] 15 to 70% by weight of a compound of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) and 5 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzenesulphonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvents (e.g. aromatic hydrocarbons) ad 100% by weight. Dilution with water gives emulsions.

[0650] iv) emulsions (EW, EO, ES)

[0651] 5 to 40% by weight of a compound of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) and 1 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzenesulphonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon). The mixture is introduced with the aid of an emulsifying machine into water ad 100% by weight and made into a homogeneous emulsion. Dilution with water gives emulsions.

[0652] v) suspensions (SC, OD, FS)

[0653] In a stirred ball mill 20 to 60% by weight of the compounds of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) are comminuted with the addition of 2 to 10% by weight of dispersants and wetting agents, for example sodium lignosulphonate and alcohol ethoxylate, 0.1 to 2% by weight of thickeners, for example xanthan gum, and water ad 100%. Dilution with water gives a stable active substance suspension. For FS-type formulations up to 40% by weight of binders, for example polyvinyl alcohol, are added.

[0654] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0655] In a finely ground state 50 to 80% by weight of the compounds of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) are ground with the addition of dispersants and wetting agents, for example sodium lignosulphonate and alcohol ethoxylate, ad 100%, and are converted into water-dispersible or water-soluble granules by means of industrial apparatus, for example extruders, spray towers, fluidised beds. Dilution with water gives a stable active substance dispersion or solution.

[0656] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0657] In a finely ground state 50 to 80% by weight of the compounds of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) are ground with the addition of dispersants and wetting agents, for example sodium lignosulphonate and alcohol ethoxylate, ad 100%, and are converted into water-dispersible or water-soluble granules by means of industrial apparatus, for example extruders, spray towers, fluidised beds. Dilution with water gives a stable active substance dispersion or solution.

[0658] viii) Gels (GW, GF)

[0659] In a finely ground state 50 to 80% by weight of the compounds of the formula (I) according to the application or of a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) are ground with the addition of dispersants and wetting agents, for example sodium lignosulphonate and alcohol ethoxylate, ad 100%, and are converted into water-dispersible or water-soluble granules by means of industrial apparatus, for example extruders, spray towers, fluidised beds. Dilution with water gives a stable active substance dispersion or solution.

[0660] iv) Microemulsions (ME)

[0661] A combination comprising 5 to 20 % by weight of a compound of the formula (I) according to the application or at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) is added to 5 to 30 % by weight of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10 to 25 % by weight of a surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate) and water ad 100 % by weight. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0662] iv) Microcapsules (CS)

[0663] An oil phase comprising 5 to 50 % by weight of a compound of the formula (I) according to the application or a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C), 0 to 40 % by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbon) and 2 to 15 % by weight of an acrylic monomer (e.g. methyl methacrylate, methacrylic acid and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Free-radical polymerization initiated by a free-radical initiator leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5 to 50 % by weight of a compound of the formula (I) according to the application, 0 to 40 % by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Addition of a polyamine (e.g. hexamethylenediamine) leads to the formation of polyurea microcapsules. The monomer amount is 1 to 10 % by weight. The % by weight relates to the entire CS formulation.

[0664] ix) Dustable powders (DP, DS)

[0665] A combination comprising 1 to 10 % by weight of a compound of the formula (I) according to the application or at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) is finely ground and thoroughly mixed with a solid carrier (e.g. finely ground kaolin) ad 100 % by weight.

[0666] x) Granules (GR, FG)

[0667] A combination comprising 0.5 to 30 % by weight of a compound of the formula (I) according to the application or at least one compound of the formula (I) (component A) and at least one further compound selected from the group of herbicidal compounds B (component B) and safeners C (component C) is finely ground and combined with a solid carrier (e.g. silicates) ad 100 % by weight. Granulation is achieved by extrusion, spray-drying or fluidized bed.

[0668] xi) Ultra-low-volume liquids (UL)

[0669] 1 to 50 % by weight of a compound of the formula (I) according to the application or a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from herbicidal compounds B (component B) and safeners C (component C) is dissolved in organic solvents (for example aromatic hydrocarbons) up to 100 % by weight.

[0670] The formulation types i) to xi) can optionally comprise further auxiliaries, such as 0.1 to 1 % by weight of a bactericide, 5 to 15 % by weight of an antifreeze, 0.1 to 1 % by weight of a de-foamer and 0.1 to 1 % by weight of a colorant.

[0671] The formulations and / or combinations usually comprise 0.01 to 95 % by weight, preferably 0.1 to 90 % by weight, in particular 0.5 to 75 % by weight, of a compound of the formula (I). The compounds of the formula (I) are used in a purity of from 90 % to 100 %, preferably from 95 % to 100 % (according to NMR spectrum).

[0672] For the treatment of plant propagation material, in particular seeds, it is possible to use seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), slurry treatment water-dispersible powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF). The formulations give, after dilution 2- to 10-fold, in ready-to-use preparations, an active substance concentration of from 0.01 to 60 % by weight, preferably from 0.1 to 40 % by weight. (down)

[0673] The method of application of the compounds of the formula (I), their formulations and / or combinations on plant propagation material, in particular seeds, comprises the seed dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, the compounds of the formula (I), their formulations and / or combinations are applied to the plant propagation material, respectively, by methods which do not induce germination, for example by seed dressing, pelleting, coating and dusting.

[0674] Various types of oils, wetters, adjuvants, fertilizers or micronutrients and further pesticides (for example herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the compounds of the formula (I), to the formulations comprising them and / or to the combinations which are suitable for use as tank mixes and, if appropriate not until immediately prior to use (tank mixes). These agents can be admixed with the formulations according to the application in a weight ratio of 1 :100 to 100:1, preferably 1 :10 to 10:1.

[0675] The user will generally use the compounds of the formula (I), the formulations comprising them and / or combinations for the treatment of weeds in the context of a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane or an irrigation system. The formulations are generally prepared with water, buffers and / or other auxiliaries to the desired application concentration, giving ready-to-use spray liquors or formulations of the present application. From 20 to 2000, preferably from 50 to 400, litres of ready-to-use spray liquor per hectare of agricultural area utilized are generally applied.

[0676] According to one embodiment, the user can mix the individual components or partially premixed components of the formulations of the present application, for example components comprising the compounds of the formula (I) and, optionally, active substances from group B and / or C), in a spray tank and, if appropriate, add further auxiliaries and additives.

[0677] In another embodiment, the user can mix the individual components of the formulations of the present application, for example the individual parts of a kit or the individual parts of a binary or ternary mixture, in a spray tank and, if appropriate, add further auxiliaries.

[0678] In another embodiment, the individual components or partially premixed components of the formulations of the present application, for example components comprising the compounds of the formula (I) and, optionally, active substances from group B and / or C), can be applied jointly, for example after tank mixing, or sequentially.

[0679] The compounds of the formula (I) are suitable as herbicides. They are suitable for use directly as suitable formulations or in combination with at least one further compound selected from herbicidally active compounds B (component B) and safeners C (component C).

[0680] The compounds of the formula (I) or the formulations and / or combinations comprising them control undesired plants very effectively, especially at high application rates, in non-crop areas. They act on broad-leaved weeds and grasses in crops such as wheat, rice, corn, soybean and cotton without causing any significant damage to the crop plants. The effect is observed mainly at low application rates.

[0681] The compounds of the formula (I) or the formulations and / or combinations comprising them are applied to the plants, mainly by spraying the leaves. Here, application can be carried out using, for example, water as carrier by conventional spray techniques using a spray volume of about 100 to 1000 1 / ha, for example 300 to 400 1 / ha. The compounds of the formula (I) or the formulations and / or combinations comprising them can also be applied by low-volume or ultra-low-volume methods or in the form of microgranules.

[0682] Application of the compounds of the formula (I) or the formulations and / or combinations comprising them can be carried out before, during and / or after emergence of the undesired plants, preferably during and / or after.

[0683] The application of the compounds of formula (I) or formulations and / or combinations comprising them can be carried out before or during sowing.

[0684] The compounds of formula (I) or formulations and / or combinations comprising them can be applied pre-emergently, post-emergently or before planting, or with the seed of the crop plant. It is also possible to apply the compounds of formula (I) or formulations and / or combinations comprising them by treating the seed of the crop plant with the compounds of formula (I) or formulations and / or combinations comprising them. If the active ingredients are not well tolerated by certain crop plants, it is possible to use application techniques in which the combination is sprayed on by means of a spraying apparatus in such a way that the leaves of sensitive crop plants are not touched as much as possible, while the active ingredients reach the leaves of the undesired plants growing underneath or the surface of the bare soil (post-directed, lay-by procedure).

[0685] In another embodiment, the compounds of formula (I) or formulations and / or combinations comprising them can be applied by treating the seed. The treatment of seed essentially comprises all procedures known to the person skilled in the art which are based on the compounds of formula (I) or formulations and / or combinations prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, seed multilayer coating, seed encrusting, seed drenching and seed granulation). The combination can be applied here diluted or undiluted.

[0686] The term "seed" includes all types of seeds, such as corn, seed, fruit, tuber, seedling and similar forms. The term seed is preferred here to describe corn and seed. The seed used can be seed of the crop plants mentioned above, but also seed of transgenic plants or plants obtained by conventional breeding methods.

[0687] When used in plant protection, the application rates of the active substances, i.e. the compounds of formula (I), component B and, if appropriate, component C, depend on the kind of effect desired and are, for example, from 0.001 to 2 kg / ha, preferably from 0.005 to 2 kg / ha, more preferably from 0.05 to 0.9 kg / ha, in particular from 0.1 to 0.75 kg / ha.

[0688] In another embodiment of the present application, the application rates of the compounds of formula (I), component B and, if appropriate, component C, are from 0.001 to 3 kg / ha, preferably from 0.005 to 2.5 kg / ha, in particular from 0.01 to 2 kg / ha of active substance (a.s.).

[0689] In another preferred embodiment of the present application, the application rates of the compounds of formula (I) of the present application (total amount of compounds of formula (I)) are from 0.1 to 3000 g / ha, preferably from 10 to 1000 g / ha, depending on the target of control, the season, the target plant and the growth stage.

[0690] In another preferred embodiment of the present application, the application rate of the compound of formula (I) is 0.1 to 5000 g / ha, preferably 1 to 2500 g / ha or 5 to 2000 g / ha.

[0691] In another preferred embodiment of the present application, the application rate of the compound of formula (I) is 0.1 to 1000 g / ha, preferably 1 to 750 g / ha, more preferably 5 to 500 g / ha.

[0692] The application rates of the required herbicidal compound B are generally 0.0005 to 2.5 kg / ha, preferably 0.005 to 2 kg / ha or 0.01 to 1.5 kg / ha a.s.

[0693] The application rates of the required safener C are generally 0.0005 to 2.5 kg / ha, preferably 0.005 to 2 kg / ha or 0.01 to 1.5 kg / ha a.s.

[0694] In the treatment of plant propagation materials, such as seeds, for example by dusting, coating or impregnating the seeds, the active amounts generally required are 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, most preferably 5 to 100 g per 100 kg of plant propagation material, preferably seeds.

[0695] In another embodiment of the present application, for the treatment of seeds, the application rates of the active substances, i.e. of the compound of formula (I), of component B and, if appropriate, of component C, are generally 0.001 to 10 kg per 100 kg of seeds.

[0696] When used for the protection of materials or stored products, the application rates of the active substances depend on the kind of the application area and on the desired effect. In the protection of materials, the amounts generally applied are 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of the material to be treated.

[0697] In the case of the combinations according to the present application, it is not important whether the compound of formula (I) and the other components B and / or C are formulated and applied jointly or separately.

[0698] In the case of separate application, it is less important in which order the applications are carried out. It is only essential that the compound of formula (I) and the other components B and / or C are applied within the time range which allows these active ingredients to act simultaneously on the plants, preferably within a time range of at most 14 days, in particular at most 7 days.

[0699] Depending on the method of application, the compounds of formula (I) or formulations and / or combinations comprising them can additionally be used for the elimination of unwanted plants in a number of other crops. Suitable crop plants are, for example, Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Mentha x piperita, Musa spec., Oenothera biennis, Oryza sativa, Panicum miliaceum, Persea americana, Petroselinum crispum, Phaseolus lunatus, Phaseolus vulgaris, Pisum sativum, Prunus armeniaca, Prunus avium, Prunus dulcis, Prunus persica, Punica granatum, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Theobroma cacao, Trifolium repen, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera.), Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

[0700] Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

[0701] Especially preferred crops are cereals, maize, soybean, rice, oilseed rape, cotton, potato, peanuts or perennial crops.

[0702] The compounds of formula (I) of the present application or formulations and / or combinations comprising them can also be used in crops which have been modified by mutagenesis or genetic engineering to provide new traits to plants or to modify already existing traits.

[0703] The term "crops" as used herein also includes plants (agricultural crops) which have been modified by mutagenesis or genetic engineering to provide new traits to plants or to modify already existing traits.

[0704] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques to create mutations at specific locations in the plant genome. Targeted mutagenesis techniques usually use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases to achieve the targeting effect.

[0705] Genetic engineering usually uses recombinant DNA techniques which are not readily available in nature by crossing, mutagenesis or natural recombination to create modifications in the plant genome. Usually one or more genes are integrated into the genome of a plant to add a trait or to improve a trait. These integrated genes are also referred to as transgenes in the art, while plants comprising such transgenes are referred to as transgenic plants. This plant transformation process usually results in several transformation events which differ in the genomic location where the transgene has been integrated. Plants comprising a specific transgene at a specific genomic location are usually described as comprising a specific "event", the latter being referred to by a specific event name. Traits which have been introduced into plants or which have been modified include herbicide tolerance, insect resistance, improved yield as well as tolerance to abiotic conditions such as drought.

[0706] Herbicide tolerance has been created both by the use of mutagenesis as well as by the use of genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding programs include maize varieties with the following names: commercially available plant varieties. However, most herbicide tolerance traits have been created via the use of transgenes.

[0707] Glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides as well as 4-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors such as isoxaflutole and mesotrione.

[0708] Transgenes that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, gox v247; for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1 and aad-12; for dicamba tolerance: dmo; for oxynil herbicide tolerance: bxn; for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; for ALS inhibitor herbicide tolerance: csr1-2; for HPPD inhibitor herbicide tolerance: hppd PF, W336 and avhppd-03.

[0709] Transgenic maize events comprising herbicide tolerance genes are, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but others are not excluded.

[0710] Transgenic soybean events comprising herbicide tolerance genes are, for example, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, W62, W98, FG72 and CV127, but others are not excluded.

[0711] Transgenic cotton events comprising herbicide tolerance genes are, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40, but others are not excluded.

[0712] Transgenic canola events comprising herbicide tolerance genes are for example MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3, but others are not excluded.

[0713] Insect resistance is mainly generated by transferring bacterial genes for pesticidal proteins into plants. The most commonly used transgenes are toxin genes of Bacillus spp. and synthetic variants thereof, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also plant-derived genes, especially genes coding for protease inhibitors, such as CpTI and pinII, were transferred into other plants. Another approach uses transgenes to generate double-stranded RNA in the plant to target and down-regulate insect genes. An example for such a transgene is dvsnf7.

[0714] Transgenic maize events comprising insecticidal protein genes or double-stranded RNA are for example Bt10, Bt1 1, Bt176, MON801, MON802, MON809, MON810, MON863, MON8741 1, MON88017, MON89034, 33121, 41 14, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098, but others are not excluded.

[0715] Transgenic soybean events comprising insecticidal protein genes are for example MON87701, MON87751 and DAS-81419, but others are not excluded.

[0716] Transgenic cotton events comprising insecticidal protein genes are for example SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event 1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281 -24-236, 3006-210-23, GHB1 19 and SGK321, but others are not excluded.

[0717] Increased yield is generated by increasing ear biomass using for example the transgene athb17 present in corn event MON 87403 or by increasing photosynthesis using for example the transgene bbx32 present in soybean event MON87712.

[0718] Crops comprising modified oil content have been generated by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

[0719] Tolerance to abiotic conditions, in particular to drought, is generated by using the transgene cspB comprised by corn event MON 87460 and by using the transgene Hahb-4 comprised by soybean event MON87751.

[0720] Traits are usually combined by combining genes in a transformation event or by combining different events during a breeding process. Preferred combinations of traits are combinations of herbicide tolerance to different classes of herbicides, combinations of insect tolerance to different species of insects, in particular combinations of lepidopteran and coleopteran insect tolerance, combinations of herbicide tolerance and resistance to one or several types of insects, combinations of herbicide tolerance and increased yield and combinations of herbicide tolerance and tolerance to abiotic conditions.

[0721] Plants comprising single or stacked traits as well as genes and events providing these traits are well known in the art. Detailed information on mutagenized or integrated genes and corresponding events can be obtained from the websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http: / / www.isaaa.org / gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http: / / cera-gmc.org / GMCropDatabase) as well as from patent applications like EP 3028573 and WO 2017 / 011288.

[0722] The use of the compounds of formula (I) of the present application or of the formulations and / or combinations comprising them on crops can lead to effects which are specific to crops comprising certain genes or events. These effects can involve changes in the growth behavior or changes in the tolerance to biotic or abiotic stress factors. Such effects can include, inter alia, increased yield, increased resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed maturity, cold or heat tolerance and changes in the amino acid or fatty acid profile or content.

[0723] Furthermore, plants containing altered contents of certain ingredients or new contents of ingredients by the use of recombinant DNA techniques are also included, for example potatoes which produce increased amounts of amylopectin (e.g. Amflora® Potatoes, BASF SE, Germany).

[0724] Furthermore, it has been found that the compounds of formula (I) of the present application or of the formulations and / or combinations comprising them are also suitable for defoliation and / or desiccation of plant parts of crops such as cotton, potatoes, rapeseed rape, sunflower, soybean or broad bean, in particular cotton. In this connection, formulations and / or combinations for the desiccation and / or defoliation of crops, processes for the preparation of these formulations and / or combinations and methods for the desiccation and / or defoliation of plants using the compounds of formula (I) have been found.

[0725] As desiccants, the compounds of formula (I) are particularly suitable for the desiccation of the aboveground parts of agricultural crops such as potatoes, rapeseed rape, sunflower and soybean and also cereals. This makes fully mechanized harvesting of these important agricultural crops possible.

[0726] It is also of economic interest to facilitate the harvesting of citrus fruits, olives and other drupes, pomes and nuts of various species and varieties by concentrating the splitting or the reduction of the adhesion to the tree over a certain period of time. The same mechanism, i.e. the facilitation of the detachment of the fruit parts or leaf parts from the branch parts of the plant, is also necessary for the controlled defoliation of useful plants, in particular cotton.

[0727] Furthermore, the shortening of the time interval for the maturation of individual cotton plants leads to an increase in the fiber quality after harvesting.

[0728] A chemical example

[0729] Chemical bonds drawn as bars in chemical formulae (see, for example, Cpds I40, I60 below) represent the relative stereochemistry on the ring system.

[0730] Example 1:

[0731] Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propionic acid (Inter A)

[0732]

[0733] Triethylamine (24.24 g, 240 mmol) was added dropwise to a solution of O1-benzyl O3-tert-butyl malonic acid ester (1) (30 g, 120 mmol) and tosyl azide (26 g, 132 mmol) in acetonitrile (300 mL) at 10 °C. The mixture was stirred at 20 °C for 48 h. The mixture was concentrated and purified with silica gel chromatography (petroleum ether: ethyl acetate = 5:1) to give O1-benzyl O3-tert-butyl-2-diazo malonic acid ester (2) (25 g, 75% yield) as a yellow oil.1H NMR: (400 MHz, CDCl3) δ 7.40-7.34 (m, 5H), 5.27 (s, 2H), 1.52 (s, 9H).

[0734]

[0735] Tetracetic acid dirhodium ([Rh(OAc)2]2) (143 mg) was added to a solution of O1-benzyl O3-tert-butyl-2-diazo malonic acid ester (2) (20 g, 72.46 mmol), methanol (14 mL) in toluene (300 mL) at 15 °C. The mixture was stirred at 60 °C for 16 h. The mixture was filtered and the filtrate was concentrated, purified by silica gel chromatography eluted with (petroleum ether: methyl tert-butyl ether = 5:1) to give O1-benzyl O3-tert-butyl 2-methoxy malonic acid ester (3) (19 g, 93% yield) as a yellow oil.1H NMR: (400 MHz, CDCl3) δ = 7.43-7.30 (m, 5H), 5.32-5.20 (m, 2H), 4.33 (s, 1H), 3.55-3.46 (m, 3H), 1.39 (s, 9H).

[0736]

[0737] To a solution of O1-benzyl O3-tert-butyl 2-methoxy malonic acid ester (3) (19 g, 67.85 mmol) in dichloromethane (150 mL) was added trifluoroacetic acid (TFA) (30 mL). The mixture was stirred at 20 °C for 6 h. The mixture was added to water and extracted with dichloromethane, the organic layer was washed with water, brine, dried, concentrated to give compound 3-benzyloxy-2-methoxy-3-oxo-propanoic acid (4) (11.5 g, 75% yield) as a yellow oil.1H NMR: (400 MHz, CDCl3) δ = 10.40 (br s, 1H), 7.43-7.30 (m, 5H), 5.28 (s, 2H), 4.51 (s, 1H), 3.53 (s, 3H).

[0738]

[0739] A solution of 1-propanephosphonic anhydride (T3P) (22.7 g, 35.71 mmol, 50% in ethyl acetate) was added to a solution of 3-benzyloxy-2-methoxy-3-oxo- propanoic acid (4) (4 g, 17.86 mmol) and 3,5-dichloroaniline (5) (3.45 g, 21.4 mmol) in acetonitrile (100 mL). The mixture was stirred at 70 °C for 16 h. The mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried, concentrated and purified by column chromatography on silica gel eluting with (petroleum ether: methyl tert-butyl ether = 5: 1) to give benzyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propanoate 6 (5.5 g, 81% yield) as a yellow oil.1H NMR: (400 MHz, CDCI3) δ 8.33 (br s, 1 H), 7.53 (d, J = 1.8 Hz, 2 H), 7.42 - 7.34 (m, 5 H), 7.14 (t, J = 1.8 Hz, 1 H), 5.29 (s, 2 H), 4.47 (s, 1 H), 3.54 (s, 3 H).

[0740]

[0741] Palladium on carbon (Pd / C) (1 g, 10%) was added to a solution of benzyl 3-(3,5- dichloroanilino)-2-methoxy-3-oxo-propanoate (6) (5.5 g, 14.98 mmol) in tetrahydrofuran (100 mL). The mixture was stirred under hydrogen gas H2(15 psi) at 10 °C for 2 h. The mixture was filtered through a pad of celite; the filtrate was concentrated to give 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter A) (3.5 g, 84% yield) as a yellow solid.1H NMR: (400 MHz, CD3OD) δ 7.69 (d, J = 1.9 Hz, 2 H), 7.18 (t, J = 1.8 Hz, 1 H), 4.48 (s, 1 H), 3.53 (s, 3 H).

[0742] Example 2:

[0743] Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter B)

[0744] The synthesis was carried out similarly to Walker, Daniel P. et al. Synthesis, (7), 1113-1119, 2011.

[0745]

[0746] To a solution of methyl 4-bromofuran-2-carboxylate (1) CAS 58235-80-6 (6 g, 29.27 mmol) in toluene (60 mL) was added tert-butyl carbamate (BocNH2) (4.1 g, 35.12 mmol), potassium carbonate (10.1 g, 73.14 mmol), CuI (1.67 g, 8.78 mmol) and (CH3NHCH2)2 (1.54 g, 17.56 mmol) at 15 °C. Then, the mixture was stirred at 130 °C for 16 hours under N2. The mixture was diluted with water (150 mL), filtered and extracted with ethyl acetate (100 mL), the organic layer was washed with brine, dried, concentrated and purified by silica gel chromatography (petroleum ether: ethyl acetate = 10:1) to give methyl 4-(tert-butoxycarbonylamino)furan-2-carboxylate (1.75 g) as a white solid.

[0747]

[0748] To a solution of dry rhodium on carbon (Rh / C) (2.5 g, cat.) in methanol (500 mL) was added methyl 4-(tert-butoxycarbonylamino)furan-2-carboxylate (2) (5 g, 20.66 mmol) at 15 °C. Then, the mixture was stirred at 30 °C for 16 hours under hydrogen (H2) (50 psi). The mixture was filtered and concentrated to give cis-4-(tert-butoxycarbonylamino)tetrahydrofuran-2-carboxylate (3) (3 g, 60% yield) as a white solid which was used in the next step without further purification.

[0749]

[0750] To a mixture of cis-4-(tert-butoxycarbonylamino)tetrahydrofuran-2-carboxylate (3) (4.2 g, 17.15 mmol) in dichloromethane (140 mL) was added HCl in ethyl acetate (140 ml, 1 M) at 15 °C and stirred at 25 °C for 4 hours. The mixture was concentrated to give cis-methyl 4- aminotetrahydrofuran-2-carboxylate Inter B (3 g, crude) as a white solid (HCl-salt).1H NMR: (400 MHz, D2O) δ 4.62 (dd, J = 8.9, 6.9 Hz, 1H), 4.15 - 4.00 (m, 3H), 3.79 (s, 3H), 2.88 - 2.78 (m, 1H), 2.19 - 2.11 (m, 1H).

[0751] Example 3:

[0752] Synthesis of cis-N-(3,5-dichlorophenyl)-2-methoxy-N'-[5-(methylcarbamoyl)- tetrahydrofuran-3-yl]malonamide (Cpd. I. 60)

[0753]

[0754] To a mixture of Inter A (718 mg, 2.09 mmol) in acetonitrile (15 mL) at 25 °C was added Inter B (467 mg, 2.59 mmol), a solution of 1-propane phosphonic anhydride in ethyl acetate (T 3 P) (2.47 g, 3.885 mmol) and diisopropylethylamine (1.85 mL, 17.36 mmol) and stirred at 75 °C under N2for 2 hours. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated and purified by preparative HPLC (acetonitrile / water with trifluoroacetic acid) to give the desired cis- methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propionyl]amino]tetrahydrofuran-2- carboxylate (Cpd. I. 40) (170 mg, 16. % yield) as a white solid.1H NMR: (400 MHz, CDCl3) δ 8.86-8.95 (m, 1H) 7.49-7.60 (m, 3H) 7.13 (d, J = 1.76 Hz, 1H), 4.52-4.73 (m, 2H), 4.26 (d, J = 3.51 Hz, 1H), 3.94-4.08 (m, 2H) 3.80 (d, J = 17.82 Hz, 3H), 3.67 (d, J = 3.01 Hz, 3H), 2.50-2.61 (m, 1H), 2.09 (dt, J = 7.09, 3.73 Hz, 1H).

[0755]

[0756] To a mixture of cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]tetrahydrofuran-2-carboxylic acid methyl ester (2.7 g, 6.9 mmol) in tetrahydrofuran (32.4 mL) at 25 °C was added LiOH (1.16 g, 27.7 mmol) in water (10.8 mL) and stirred at 25 °C for 2 hours. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated and purified by preparative HPLC (trifluoroacetic acid 0.1%, acetonitrile-water) to give cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propionyl]amino]tetrahydrofuran-2-carboxylic acid ester (Cpd. I.60) (1.3 g, 48.3% yield) as a white solid.1H NMR: (400 MHz, DMSO-d6) δ 10.34 (d, J = 5.26 Hz, 1H), 8.30 (dd, J = 16.22, 7.02 Hz, 1H), 7.78 (t, J = 1.75 Hz, 2H), 7.32 (t, J = 1.75 Hz, 1H), 4.27 - 4.41 (m, 3H) 3.90 (ddd, J = 8.55, 6.36, 1.75 Hz, 1H), 3.64 (dt, J = 8.66, 5.54 Hz, 1H), 3.37 (s, 3H), 1.93 (dtd, J = 12.77, 6.22, 6.22, 2.85 Hz, 1H).

[0757] Example 4

[0758] Synthesis of Cpd I.144

[0759]

[0760] To a solution of dimethyl methoxypropanedioate (CAS 5018-30-4) (1) (7.6 g, 47 mmol) in dimethylformamide (50 mL) was added sodium hydride (60%, 2.2 g) under argon at 50 °C. The resulting mixture was stirred at 50 °C for further 30 minutes until no more hydrogen was evolved. After cooling to room temperature, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane di(tetrafluoroborate) (selectfluor, CAS 140681-55-6) (25 g) was added. The resulting mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3 x 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude 2-fluoro-2-methoxy-propanedioic acid dimethyl ester (2) (7.9 g, 93% yield).1H NMR: (400 MHz, CDCl3) δ 3.89 (s, 6H), 3.58 (s, 3H).

[0761]

[0762] To dimethyl 2-fluoro-2-methoxy-malonate (2) (7.9 g, 44 mmol) in tetrahydrofuran / water (1 :1) was added lithium hydroxide (LiOH) (1.05 g, 44 mmol). The reaction mixture was stirred at room temperature overnight. Tetrahydrofuran was removed under reduced pressure. The resulting aqueous solution was extracted with methyl tert-butyl ether (2 x 100 mL) and the organic phase was discarded. The aqueous layer was adjusted to pH 1 using concentrated hydrochloric acid and extracted with ethyl acetate (3 x 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude 2-fluoro-2,3-dimethoxy-3-oxo-propanoic acid (3) (5.3 g, 73% yield).1H NMR: (400 MHz, CDCI3) δ 3.92 (s, 3H), 3.61 (s, 3H).

[0763]

[0764] Amide bond formation was carried out as described above (Example 1, compound 6). Methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (4) was obtained in 56% yield.1H NMR: (400 MHz, CDCI3) δ 8.26 (s, 1H), 7.57 (s, 2H), 7.18 (s, 1H), 3.92 (s, 3H), 3.63 (s, 3H).

[0765]

[0766] To methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (4) (3.8 g, 12 mmol) in 1,2-dichloroethane (100 mL) at room temperature was added trimethyltin hydroxide (Me3SnOH) (4.4 g, 25 mmol). The reaction mixture was stirred at room temperature for 16 hours, then the reaction mixture was extracted with saturated aqueous sodium bicarbonate solution (3 x 100 mL). The combined organic phase was adjusted to pH 1 using aqueous concentrated hydrochloric acid. The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (5) (1.2 g, 33% yield). LC-MS (M+H) + : 295.8.

[0767]

[0768] To a solution of carboxylic acid (0.3 g) in dimethylformamide (DMF, 10 mL) was added amine 6 (CAS 229613-83-6). To the resulting solution was added HATU (0.42 g) followed by diisopropylethylamine (0.53 mL). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and saturated aqueous bicarbonate solution (10 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo- propionyl]amino]cyclopent-2-ene-1 -carboxylate (0.2 g, 47%, I.144) as a mixture of diastereoisomers (1 :1).1H NMR (500 MHz, Chloroform-d) δ 8.65 (s, 1H), 7.57 (d, J = 1.8 Hz, 2H), 7.43 - 7.33 (m, 1H), 7.19 - 7.13 (m, 1H), 6.03 - 5.98 (m, 1H), 5.95 - 5.89 (m, 1H), 5.11 - 5.04 (m, 1H), 3.81 - 3.73 (m, 3H), 3.65 - 3.53 (m, 4H), 2.54 - 2.45 (m, 1H), 2.06 - 1.98 (m, 1H).

[0769] Example 5:

[0770] Synthesis of (1S,4R)-4-(methylamino)cyclopent-2-ene-1 -carboxylate (Inter C)

[0771]

[0772] To a solution of (1R,4S)-2-azabicyclo[2.2.1]heptan-5-one (CAS 79200-56-9) (20.0 g, 183 mmol) in tetrahydrofuran (50 mL) at 0 °C was added sodium hydride (8.8 g, 0.22 mol). After stirring for 30 minutes, iodomethane (52 g, 0.37 mmol) was added at 0 °C and the mixture was stirred overnight. After quenching with saturated ammonium chloride solution (50 mL), the aqueous phase was separated and extracted with ethyl acetate (3 x 50 mL). The combined extracts were washed with brine, dried over sodium sulfate and concentrated to give (1R,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-one (5.6 g, 25%) as a colourless oil.

[0773]

[0774] To a solution of (1R,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-one (3.0 g, 24 mmol) in methanol (30 mL) was added thionyl chloride (3.5 mL, 49 mmol) at 0 °C. After stirring at room temperature for 3 h, the mixture was concentrated to give Inter C (2.6 g, 56%) as a colorless salt.1H NMR (400 MHz, D2O) δ 6.29 (ddd, J = 5.7, 2.5, 1.6 Hz, 1H), 6.03 (dt, J = 5.7, 2.3 Hz, 1H), 4.37 (m, 1H), 3.81 (m, 1H), 3.75 (s, 3H), 2.70 (m, 4H), 2.16 (dt, J = 14.7, 5.0 Hz, 1H).

[0775] Example 6:

[0776] Synthesis of Cpd 1155

[0777]

[0778] To a solution of the carboxylic acid (1.0 g, 3.6 mmol) in dimethylformamide (DMF, 10 mL) was added the amine Inter C (0.79 g, 4.1 mmol). To the resulting solution was added HATU (1.57 g, 4.13 mmol) followed by diisopropylethylamine (1.8 mL, 11 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (30 mL) and saturated aqueous bicarbonate (30 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as the solvent to give (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]-methyl-amino]cyclopent-2-ene-1-carboxylic acid methyl ester (700 mg, 47%, I.155) as a mixture of diastereoisomers (1 : 1).1H NMR (400 MHz, Chloroform-d) δ 8.45 (m, 2H), 7.54 (m, 4H), 7.12 (m, 2H), 6.01 (m, 2H), 5.81 (m, 2H), 5.70 (m, 2H), 5.01 (m, 2H), 4.82 (d, J = 7.6 Hz, 1H), 4.75 (d, J = 5.7 Hz, 1H), 3.51 (m, 8H), 3.03 (d, J = 4.8 Hz, 3H), 2.83 (d, J = 3.4 Hz, 3H), 2.55 (m, 2H), 2.36 (m, 4H), 2.07 (m, 4H), 1.87 (m, 4H), 1.60 (m, 4H).

[0779] Example 7:

[0780] Synthesis of Cpd 1.123

[0781]

[0782] To a solution of the carboxylic acid (120 g) in dimethylformamide (DMF, 500 mL) was added (1S,4R)-4-aminocyclopent-2-en-1 -carboxylic acid methyl ester hydrochloride (88.1 g, 496 mmol) (CAS 229613-83-6). To the resulting solution was added HATU (189 g, 496 mmol) followed by diisopropylethylamine (220 mL). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (50 mL) and saturated aqueous bicarbonate (50 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]cyclopent-2-en-1 -carboxylic acid methyl ester (105 g, 60%, I.123) as a mixture of diastereoisomers (1 :1).1H NMR (500 MHz, Chloroform-d) δ 9.14 (s, 1H), 9.08 (s, 1H), 7.53 (dd, J = 5.8, 1.8 Hz, 4H), 7.27 (m, 2H), 7.09 (m, 2H), 5.92 (m, 4H), 5.06 (q, J = 9.0 Hz, 2H), 4.27 (d, J = 5.1 Hz, 2H), 3.73 (s, 6H), 3.66 (s, 3H), 3.64 (s, 3H), 3.54 (m, 2H), 2.49 (tt, J = 13.8, 8.4 Hz, 2H), 1.95 (ddt, J = 14.1, 10.6, 3.5 Hz, 2H).

[0783] Example 8:

[0784] Synthesis of Cpd 1.136

[0785]

[0786] To (1S,4R)-methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propionyl]amino] cyclopent-2-ene-1-carboxylate (Cpd. I.123) (6.0 g, 15 mmol) in 1,2-dichloroethane (100 mL) was added trimethyltin hydroxide (Me3SnOH) (5.4 g, 30 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours, then the reaction mixture was extracted with saturated aqueous sodium bicarbonate solution (3 x 100 mL). The combined organic phase was adjusted to pH 1 using concentrated aqueous hydrochloric acid. The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propionyl]amino]cyclopent-2-ene-1-carboxylic acid (5.0 g, 86% yield, I.136) as a mixture of diastereoisomers (1 :1).1H NMR (500 MHz, chloroform-d) δ 9.18 (s, 1H), 9.13 (s, 1H), 7.53 (m, 4H), 7.38 (m, 2H), 7.10 (m, 2H), 5.97 (m, 4H), 5.07 (s, 2H), 4.29 (m, 2H), 3.61 (m, 8H), 2.53 (m, 2H), 1.99 (m, 2H).

[0787] Example 9:

[0788] Synthesis of Cpd I.142

[0789]

[0790] To a solution of carboxylic acid (Cpd. I. 136) (500 mg, 1.29 mmol) in dimethylformamide (DMF, 10 mL) was added 2-chloroethanol (0.26 mL, 3.9 mmol). To the resulting solution was added HATU (540 mg, 1.42 mmol) followed by triethylamine (0.68 mL, 3.9 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and saturated aqueous bicarbonate solution (10 mL). The resulting mixture was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as the solvent to give (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]cyclopent-2-ene-1-carboxylic acid 2-chloroethyl ester (260 mg, 45%, I. 142) as a mixture of diastereoisomers (2:1).1H NMR (500 MHz, chloroform-d) δ 9.08 (m, 2H), 7.52 (m, 4H), 7.20 (s, 1H), 7.10 (m, 2H), 5.94 (m, 4H), 5.11 (m, 2H), 4.37 (m, 4H), 4.27 (m, 2H), 3.69 (m, 13H), 2.57 (m, 2H), 1.96 (m, 2H).

[0791] Example 10:

[0792] Synthesis of Cpd I.175

[0793]

[0794] To a solution of carboxylic acid (Cpd. I. 136) (200 mg, 0.517 mmol) in tetrahydrofuran (5 mL) was added dimethylformamide (DMF, 0.1 mL, 0.5 mmol) and oxalyl chloride (0.09 mL, 1.0 mmol). After stirring for 1 h, sodium benzoate (CAS 20194-18-7) (60 mg, 0.45 mmol) was added to the mixture and stirring was continued for 3 h. After quenching the reaction with water (5 mL), the aqueous layer was separated and extracted with ethyl acetate (3 x 5 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as the solvent to give (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]cyclopentyl-2-ene-1-carboxylic acid benzyl ester (24 mg, 10%, I. 175) as a mixture of diastereoisomers (1 :1). LC-MS (M+H) + : 477.1.

[0795] Example 11:

[0796] Synthesis of Cpd I.201

[0797]

[0798] To a solution of carboxylic acid (Cpd. I. 136) (300 mg, 0.775 mmol) in dimethylformamide (DMF, 5 mL) was added propargylamine (CAS 2450-71-7) (51 mg, 0.93 mmol). To the resulting solution was added HATU (95%, 372 mg, 0.93 mmol) followed by diisopropylethylamine (0.40 mL, 2.3 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (5 mL) and saturated aqueous bicarbonate solution (5 mL). The resulting mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as the solvent to give N-(3,5-dichlorophenyl)-2-methoxy-N'-[(1R,4S)-4-(prop-2-ynylcarbamoyl)cyclopent-2-en-1- yl]propanediamine (47 mg, 14%, I.201) as a mixture of diastereoisomers (1 :1).1H NMR (500 MHz, Chloroform-d) δ 8.98 (m, 2H), 7.66 (s, 2H), 7.55 (m, 4H), 7.10 (s, 2H), 5.92 (m, 6H), 5.05 (d, J = 7.9 Hz, 2H), 4.25 (s, 2H), 4.08 (m, 4H), 3.66 (s, 3H), 3.64 (s, 3H), 3.33 (s, 2H), 2.42 (m, 2H), 2.27 (m, 2H), 1.93 (t, J = 14.7 Hz, 2H).

[0799] Example 12:

[0800] Synthesis of Cpd I.26

[0801]

[0802] To a solution of carboxylic acid (Inter A) (10 g, 36 mmol) in dimethylformamide (DMF, 100 mL) was added 4-aminobutanoic acid methyl ester hydrochloride (CAS 13031-60-2) (5.5 g, 36 mmol). To the resulting solution was added HATU (15 g, 40 mol) followed by triethylamine (15 mL, 108 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (50 mL) and saturated aqueous bicarbonate (50 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]butyric acid methyl ester (10.6 g, 78%, Cpd. I.26).1H NMR (500 MHz, chloroform-d) δ 9.29 (s, 1H), 7.51 (d, J = 1.9 Hz, 2H), 7.08 (m, 2H), 4.31 (s, 1H), 3.68 (s, 3H), 3.64 (s, 3H), 3.37 (q, J = 6.7 Hz, 2H), 2.38 (t, J = 7.2 Hz, 2H), 1.89 (p, J = 7.1 Hz, 2H).

[0803] Example 13:

[0804] Synthesis of Cpd I.116

[0805]

[0806] To a solution of methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]butanoate (Cpd. I.26) (700 mg, 1.86 mmol) in a 1 :1 mixture of water (20 mL) and THF (20 mL) was added lithium hydroxide (102 mg, 4.24 mmol). After stirring overnight, the reaction was quenched with aqueous hydrochloric acid (1 M, 10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure to give 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo- propionyl]amino]butanoic acid as a colourless oil (550 mg, 82%).1H NMR (500 MHz, Chloroform-d) δ 8.22 (s, 1H), 7.53 (d, J = 1.8 Hz, 2H), 7.11 (s, 1H), 3.75 (d, J = 5.9 Hz, 1H), 3.67 (s, 3H), 3.29 (td, J = 7.0, 2.7 Hz, 2H), 3.22 (d, J = 5.9 Hz, 1H), 2.37 (t, J = 7.2 Hz, 2H), 1.90 (p, J = 7.1 Hz, 2H).

[0807] Example 14:

[0808] Synthesis of Cpd I.202-A

[0809]

[0810] To a solution of carboxylic acid (Cpd. I.116) (200 mg, 0.551 mmol) in dichloromethane (30 mL) was added methanesulfonamide (157 mg, 1.65 mmol), 4-dimethylaminopyridine (DMAP, 20 mg, 0.17 mmol) and N,N'-dicyclohexylmethane diimine (DCC, 114 mg, 0.551 mmol). After stirring overnight, the reaction was quenched with water (20 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give N-(3,5-dichlorophenyl)-N'-[4-(methanesulfonamido)-4-oxo-butyl]-2-methoxy- malonamide (25 mg, 10%, Cpd. I.202-A). LC-MS (M+H) + : 439.9.

[0811] Example 15:

[0812] Synthesis of Cpd I.203

[0813]

[0814] To a solution of carboxylic acid Cpd.I.116 (200 mg, 0.551 mmol) in dimethylformamide (DMF, 10 mL) was added methoxy(methyl)ammonium chloride (80.6 mg, 0.826 mmol). HATU (314 mg, 0.826 mol) was added to the resulting solution, followed by triethylamine (0.23 mL, 1.62 mmol). The resulting reaction mixture was stirred at room temperature overnight. Water (10 mL) and saturated aqueous bicarbonate solution (10 mL) were added to the reaction mixture. The resulting mixture was extracted with ethyl acetate (3×10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as a solvent to give N-(3,5-dichlorophenyl)-2-methoxy-N'-[4-[methoxy(methyl)amino]-4-oxo-butyl]propanediamine (180 mg, 81%, Cpd.I.203). 1H NMR (500MHz, chloroform-d) δ9.12(s,1H),7.53(d,J=1.8Hz,2H),7.21(s,1H),7.10(t,J=1.8Hz,1H),4.26(s ,1H),3.66(s,3H),3.65(s,3H),3.37(qd,J=6.6,3.9Hz,2H),3.17(s,3H),2.50(m,2H),1.90(m,2H).

[0815] High performance liquid chromatography: HPLC column Kinetex XB C18 1.7μ (50x2.1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 at 60°C in 1.5 minutes, flow rate gradient from 0.8 to 1.0 ml / min in 1.5 minutes).

[0816] Analogously to the above examples, starting from commercial diesters and using commercial amines, the following compounds of formula (I) were prepared, wherein R 1 and R 9 It is hydrogen:

[0817]

[0818] Table 2A

[0819] HPLC / MS = mass to charge ratio

[0820]

[0821]

[0822]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828]

[0829]

[0830]

[0831]

[0832]

[0833] The following compounds of formula (I) were prepared in analogy to the examples described above, starting from commercially available diesters and using commercially available amines, wherein R 2 , R 6 , R 8 and R 9 are hydrogen:

[0834]

[0835] Table 2B

[0836] In Table 2B, means cyclopropyl.

[0837] HPLC / MS = mass to charge ratio

[0838]

[0839]

[0840] The following compounds of formula (I) were prepared in analogy to the examples described above, starting from commercially available diesters and using commercially available amines, wherein R 6 and R 8 are hydrogen:

[0841]

[0842] Table 2C

[0843] HPLC / MS = mass to charge ratio

[0844]

[0845] In analogy to the above examples, the following compounds of formula (I) wherein R 2 , R 6 , R 8 and R 9 are hydrogen are prepared starting from commercially available diesters and using commercially available amines:

[0846]

[0847] Table 2D

[0848] In Table 2D, R means cyclopropyl.

[0849] HPLC / MS = mass to charge ratio

[0850]

[0851]

[0852]

[0853]

[0854] B Examples of use

[0855] The herbicidal activity of the compounds of formula (I) is demonstrated by the following greenhouse tests:

[0856] The culture vessels used are plastic flower pots containing loamy sand with about 3.0% humus as substrate. The seeds of the test plants are sown individually for each variety.

[0857] For pre-emergence treatment, the active ingredient is applied as a suspension or emulsion in water directly after sowing by means of a fine distribution nozzle. The vessels are watered gently to promote germination and growth, then covered with a transparent plastic hood until the test plants have rooted. This covering leads to uniform germination of the test plants, unless this is impaired by the active ingredient.

[0858] For post-emergence treatment, the test plants are first grown to a height of 3-15 cm, depending on the habit of the plant, and treated with the active ingredient as a suspension or emulsion in water only at this time. To this end, the test plants are either sown directly and grown in the same vessels, or they are first grown individually as seedlings and transplanted into the test vessels a few days before treatment.

[0859] The test plants are kept at 10-25°C or 20-35°C, respectively, depending on the variety.

[0860] The test period is 2-4 weeks. During this time the test plants are looked after and their response to the respective treatment is evaluated.

[0861] The evaluation was performed using a rating from 0 to 100. 100 means that no test plants emerged or at least the ground part was completely damaged, while 0 means no damage or normal growth process. A score of 70 to 90 was given for good herbicidal activity, while 90 to 100 for very good herbicidal activity.

[0862] The test plants used in the greenhouse tests belong to the following species:

[0863] Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Avena fatua ECHCG Echinocloa crus-galli LOLMU Lolium multiflorum POLCO Polygonum convolvulus SETFA Setaria faberi SETVI Setaria viridis

[0864] At an application rate of 0.125 kg / ha by pre-emergence method:

[0865] • Compound I.159, I.185, I.191 show very good herbicidal activity against AMARE.

[0866] • Compound I.159 shows very good herbicidal activity against ALOMY.

[0867] • Compound I.159 shows very good herbicidal activity against SETFA.

[0868] • Compound I.169, I.185 show very good herbicidal activity against APESV.

[0869] • Compound I.169, I.191 show good herbicidal activity against ECHCG.

[0870] • Compound I.185 shows very good herbicidal activity against ABUTH.

[0871] At an application rate of 0.250 kg / ha by pre-emergence method:

[0872] • Compound I.161, I.162, I.164, I.167, I.168, I.172, I.186, I.192, I.195, I.210 show very good herbicidal activity against APESV.

[0873] • Compound I.155, I.156, I.157, I.173 show good herbicidal activity against APESV.

[0874] • Compound I.163, I.192, I.198, I.210 show very good herbicidal activity against ABUTH.

[0875] • Compound I.157, I.162, I.165, I.166, I.174, I.176, I.179, I.180, I.181, I.184, I.186 show good herbicidal activity against ABUTH.

[0876] • Compounds I.161, I.162, I.163, I.165, I.166, I.167, I.172, I.174, I.175, I.176, I.179, I.180, I.181, I.183, I.184, I.186, I.189, 198, I.210 show very good herbicidal activity on AMARE.

[0877] • Compounds I.164, I.188, I.190 show good herbicidal activity on AMARE.

[0878] • Compounds I.161, I.163, I.164, I.166, I.175, I.176, I.177, I.184, I.195, I.211 show very good herbicidal activity on SETFA.

[0879] • Compound I.173 shows good herbicidal activity on SETFA.

[0880] • Compounds I.165, I.167, I.175, I.177, I.181, I.183, I.188, I.189, I.190, I.195, I.198 show very good herbicidal activity on ECHCG.

[0881] • Compound I.168 shows good herbicidal activity on ECHCG.

[0882] • Compounds I.174, I.177, I.178, I.180, I.183, I.188, I.189, I.211 show very good herbicidal activity on ALOMY.

[0883] At an application rate of 0.500 kg / ha, by pre-emergence method:

[0884] • Compounds I.13, I.36 show very good herbicidal activity on ALOMY.

[0885] • Compounds I.13, I.64 show very good herbicidal activity on AMARE.

[0886] • Compounds I.9, I.28, I.33, I.39, I.51, I.55, I.57, I.58, I.62, I.104, I.108, I.109, I.113, I.122, I.123, I.124, I.158, I.205, I.207 show very good herbicidal activity on APESV.

[0887] • Compounds I.38, I.45, I.52, I.61, I.64, I.77, I.110, I.115, I.118, I.119, I.121, I.145, I.208 show good herbicidal activity on APESV.

[0888] • Compounds I.9, I.28, I.33, I.36, I.39, I.51, I.55, I.123, I.124, I.145 show very good herbicidal activity on ECHCG.

[0889] • Compounds I.34, I.45, I.108, I.205, I.207 show good herbicidal activity on ECHCG.

[0890] • Compounds I.57, I.104, I.158, I.208 show very good herbicidal activity on SETFA.

[0891] • Compounds I.58, I.109, I.145 show good herbicidal activity on SETFA. At an application rate of 1.000 kg / ha, by pre-emergence method:

[0892] • Compound I.100 shows very good herbicidal activity on AMARE.

[0893] • Compounds I.40, I.59, I.60, I.84, I.100, I.101 show very good herbicidal activity on APESV.

[0894] • Compounds I.63, I.68, I.95 show good herbicidal activity on APESV.

[0895] • Compound I.40 shows very good herbicidal activity on ECHCG.

[0896] • Compound I.60 shows good herbicidal activity on ECHCG.

[0897] • Compounds I.59, I.101 show very good herbicidal activity on SETFA. At an application rate of 0.125 kg / ha, by post-emergence method:

[0898] • Compounds I.159, I.169, I.185, I.191, I.192 show very good herbicidal activity on ALOMY.

[0899] • Compounds I.17, I.170, I.171 show good herbicidal activity on ALOMY.

[0900] • Compounds I.159, I.185 show very good herbicidal activity against AMARE.

[0901] • Compound I.192 shows good herbicidal activity against AMARE.

[0902] • Compounds I.159, I.185 show very good herbicidal activity against ABUTH.

[0903] • Compounds I.169, I.170, I.171, I.191, I.192 show good herbicidal activity against ABUTH.

[0904] • Compounds I.17, I.170, I.191 show good herbicidal activity against AVEFA. At an application rate of 0.250 kg / ha, by post-emergence method:

[0905] • Compounds I.160, I.161, I.162, I.164, I.165, I.166, I.168, I.172, I.173, I.174, I.175, I.177, I.181, I.186, I.188, I.189, I.190, I.192, I.198, I.210, I.211 show very good herbicidal activity against ALOMY.

[0906] • Compounds I.155, I.156, I.197 show good herbicidal activity against ALOMY.

[0907] • Compounds I.160, I.161, I.162, I.163, I.164, I.165, I.166, I.167, I.168, I.172, I.173, I.174, I.175, I.176, I.177, I.180, I.181, I.183, I.184, I.186, I.189, I.195, I.198 show very good herbicidal activity against ABUTH.

[0908] • Compounds I.157, I.179, I.188, I.190, I.192, I.197, I.210 show good herbicidal activity against ABUTH.

[0909] • Compounds I.161, I.162, I.163, I.165, I.174, I.175, I.179, I.181, I.183, I.184, I.185, I.189, I.190, I.198 show very good herbicidal activity against AMARE.

[0910] • Compounds I.155, I.156, I.157, I.160, I.164, I.167, I.168, I.176, I.177, I.178, I.180, I.188, I.192 show good herbicidal activity against AMARE.

[0911] • Compounds I.163, I.172, I.173, I.178, I.211 show very good herbicidal activity against AVEFA.

[0912] • Compounds I.166, I.167, I.176, I.179, I.180, I.184, I.198 show very good herbicidal activity against ECHCG.

[0913] • Compound I.195 shows good herbicidal activity against ECHCG.

[0914] • Compounds I.183, I.195, I.210, I.211 show very good herbicidal activity against SETVI.

[0915] • Compound I.197 shows good herbicidal activity against SETVI. At an application rate of 0.500 kg / ha, by post-emergence method:

[0916] • Compounds I.47, I.51, I.104, I.108, I.109, I.158, I.205 show very good herbicidal activity against ABUTH.

[0917] • Compounds I.52, I.55, I.145, I.204 show good herbicidal activity against ABUTH.

[0918] • Compounds I.2, I.3, I.4, I.13, I.33, I.34, I.35, I.36, I.38, I.39, I.46, I.64, I.104, I.113, I.205 show very good herbicidal activity against ALOMY.

[0919] • Compounds I.5, I.6, I.18, I.23, I.26, I.27, I.41, I.45, I.54, I.70, I.74, I.80, I.83, I.105, I.110, I.208 show good herbicidal activity against ALOMY.

[0920] • Compounds I.5, I.13, I.57, I.58, I.108, I.109, I.122, I.123, I.124 show very good herbicidal activity against AMARE.

[0921] • Compounds I.26, I.47, I.41, I.54, I.56, I.80, I.117, I.118, I.119, I.120, I.121, I.145, I.158, I.204, I.205 show good herbicidal activity against AMARE.

[0922] • Compound I.42 shows good herbicidal activity against APESV.

[0923] • Compounds I.2, I.3, I.4, I.9, I.33, I.38, I.39, I.64, I.110, I.145, I.208 show very good herbicidal activity against AVEFA.

[0924] • Compounds I.5, I.18, I.27, I.35, I.52, I.70, I.74, I.77, I.83, I.105, I.129, I.113, I.117, I.207 show good herbicidal activity against AVEFA.

[0925] • Compounds I.9, I.28, I.62, I.158 show very good herbicidal activity against ECHCG.

[0926] • Compounds I.3, I.4 show very good herbicidal activity against LOLMU.

[0927] • Compound I.2 shows very good herbicidal activity against POLCO.

[0928] • Compounds I.27, I.28, I.34, I.36, I.39, I.45, I.51, I.55, I.56, I.57, I.58, I.61, I.62, I.122, I.123, I.124, I.204, I.207, I.208 show very good herbicidal activity against SETVI.

[0929] • Compounds I.23, I.26, I.35, I.38, I.46, I.118, I.119, I.120, I.121 show good herbicidal activity against SETVI. At an application rate of 1.000 kg / ha, by post-emergence method:

[0930] • Compounds I.100, I.101 show very good herbicidal activity against ABUTH.

[0931] • Compound I.96 shows good herbicidal activity against ABUTH.

[0932] • Compounds I.1, I.40, I.100 show very good herbicidal activity against ALOMY.

[0933] • Compounds I.66, I.68, I.84, I.94, I.95 show good herbicidal activity against ALOMY.

[0934] • Compounds I.59, I.60, I.63 show very good herbicidal activity against AMARE.

[0935] • Compounds I.40, I.94 show good herbicidal activity against AMARE.

[0936] • Compounds I.66, I.68, I.94, I.95, I.96 show good herbicidal activity against AVEFA.

[0937] • Compound I.40 shows good herbicidal activity against ECHCG.

[0938] • Compound I.1 shows very good herbicidal activity against POLCO.

[0939] • Compounds I.59, I.101 show very good herbicidal activity against SETVI.

[0940] • Compounds I.1, I.60, I.84 show good herbicidal activity against SETVI.

Claims

1. Herbicidal compounds of formula (I): The substituents have the following meanings: R 1 Hydrogen, C1-C3 alkyl; R 2 Hydrogen, halogen, C1-C3 alkoxy; R 3 Hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy; R 4 Hydrogen, halogen, C1-C3 alkyl; R 5 Hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy; R 6 Hydrogen, halogens; R 7 C1-C6 alkyl, C3-C6 cycloalkyl, each substituted by m groups selected from the group consisting of fluorine; R 8 Hydrogen, halogen, C1-C6 alkyl; R 9 Hydrogen, C1-C6 alkyl; X key; Y hydrogen, Z, or C1-C 12 Alkyl, C2-C 12 alkenyl, each substituted with m groups selected from: S(O) n R a and CO2R e ; Z cyclobutane, cyclopentane, cyclopentene, tetrahydrofuran or tetrazole ring, which is substituted by m groups selected from the following groups: CO2R e ; R a C1-C6 alkyl; R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, CO2R a and C1-C2 alkoxy; m 0, 1, 2, or 3; n 0, 1, or 2; or an agriculturally acceptable salt thereof, provided that the compound of formula (I) has a carboxyl group.

2. The compound according to claim 1, wherein the substituents have the following meanings: R 1 hydrogen; R 9 hydrogen.

3. The compound according to claim 1, wherein the substituents have the following meanings: R 2 Hydrogen, halogens.

4. The compound according to claim 2, wherein the substituents have the following meanings: R 2 Hydrogen, halogens.

5. The compound according to any one of claims 1 to 4, wherein the substituents have the following meanings: R 3 Hydrogen, halogen, cyano, C1-C3 alkyl; R 5 Hydrogen, halogen, cyano, C1-C3 alkyl.

6. The compound according to any one of claims 1 to 4, wherein the substituents have the following meanings: R 4 Hydrogen, halogens.

7. The compound according to claim 5, wherein the substituents have the following meanings: R 4 Hydrogen, halogens.

8. The compound according to any one of claims 1 to 4, wherein the substituents have the following meanings: R 8 Hydrogen, halogens.

9. The compound according to claim 7, wherein the substituents have the following meanings: R 8 Hydrogen, halogens.

10. The compound according to any one of claims 1 to 4, wherein the substituents have the following meanings: Y C1-C8 alkyl, C2-C8 alkenyl, each substituted by m groups selected from the group consisting of: S(O) n R a and CO2R e .

11. The compound according to claim 9, wherein the substituents have the following meanings: Y C1-C8 alkyl, C2-C8 alkenyl, each substituted by m groups selected from the following: S(O) n R a and CO2R e .

12. The compound according to any one of claims 1 to 4, wherein the substituents have the following meanings: YZ; Z cyclobutane, cyclopentane, cyclopentene or tetrahydrofuran ring, each substituted by m groups selected from the following: CO2R e .

13. The compound according to claim 1, wherein the substituents have the following meanings: R 1 hydrogen; R 2 Hydrogen, halogens; R 3 Hydrogen, halogen, cyano, C1-C3 alkyl; R 4 Hydrogen, halogens; R 5 Hydrogen, halogen, cyano, C1-C3 alkyl; R 6 Hydrogen, halogens; R 7 C1-C6 alkyl, C3-C6 cycloalkyl, each substituted by m groups selected from the group consisting of fluorine; R 8 Hydrogen, halogens; R 9 hydrogen; X key; YZ, or C1-C 12 Alkyl, C2-C 12 alkenyl, each substituted with m groups selected from: CO2R e ; Z cyclobutane, cyclopentane, cyclopentene or tetrahydrofuran ring, each substituted by m groups selected from the following: CO2R e ; R a C1-C6 alkyl; R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, CO2R a and C1-C2 alkoxy; m 0, 1, 2, or 3.

14. The compound according to claim 1, wherein the substituents have the following meanings: R 1 hydrogen; R 2 hydrogen; R 3 Halogen, cyano, C1-C3 alkyl; R 4 hydrogen or fluorine; R 5 Halogen, cyano, C1-C3 alkyl; R 6 hydrogen; R 7 C1-C6 alkyl, C3-C6 cycloalkyl; R 8 Hydrogen, halogens; R 9 hydrogen; X key; YZ; Z cyclobutane, cyclopentane, cyclopentene or tetrahydrofuran ring, which is substituted by m groups selected from the following groups: CO2R e ; R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine and C1-C2 alkoxy; m 0, 1 or 2.

15. The compound according to claim 1, wherein the substituents have the following meanings: R 1 hydrogen; R 2 hydrogen; R 3 chlorine or fluorine; R 4 hydrogen; R 5 chlorine or fluorine; R 6 hydrogen; R 7 methyl; R 8 hydrogen; R 9 hydrogen; X key; YZ; Z cyclobutane, cyclopentane, cyclopentene or tetrahydrofuran ring, which is substituted by m groups selected from the following groups: CO2R e ; R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine and C1-C2 alkoxy; m 0, 1 or 2.

16. The compound according to claim 1, wherein the substituents have the following meanings: R 1 hydrogen; R 2 hydrogen; R 3 Halogen, cyano, C1-C3 alkyl; R 4 hydrogen or fluorine; R 5 Halogen, cyano, C1-C3 alkyl; R 6 hydrogen; R 7 C1-C6 alkyl, C3-C6 cycloalkyl; R 8 Hydrogen, halogens; R 9 hydrogen; X key; Y C1-C 12 Alkyl, C2-C 12 alkenyl, each substituted with m groups selected from: CO2R e ; R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine and C1-C2 alkoxy; m 0, 1 or 2.

17. The compound according to claim 15, which is selected from the group consisting of:

18. A herbicidal composition comprising at least one compound according to any one of claims 1 to 17 and an adjuvant commonly used in the formulation of crop protection agents.

19. The composition according to claim 18, which comprises a further herbicide.

20. Use of a compound according to any one of claims 1 to 17 or a composition according to claim 18 or 19 for controlling broadleaf weeds and grass weeds.

21. A method for controlling broadleaf weeds and grass weeds, which comprises allowing at least one compound according to any one of claims 1 to 17 or a composition according to claim 18 or 19 to act on a plant, its seeds or its habitat.

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