Malonamide Herbicides

Abstract

The present invention relates to compounds of formula (I) and their use as herbicides, wherein 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, and Y is hydrogen, cyano, hydroxyl, or a linear or cyclic organic group. The present invention further relates to compositions comprising such compounds and their use for controlling unwanted vegetation. TIFF2023514787000184.tif27147

Description

[Technical Field]

[0001] The present invention relates to malonamide compounds and compositions containing same. The present invention also relates to the use of malonamide compounds or corresponding compositions for controlling unwanted vegetation. Furthermore, the present invention relates to methods of applying malonamide compounds or corresponding compositions. [Background technology]

[0002] There is a need for new herbicides that are highly active and selective, with virtually no toxicity to humans and animals, for controlling unwanted vegetation, particularly in crops.

[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 to retard plant growth.

[0005] Malonic acid derivatives are also described in US Pat. No. 3,072,473 as plant growth regulators.

[0006] Prior art compounds often have poor herbicidal activity, especially at low application rates, and / or poor selectivity resulting in poor compatibility with crop plants. Summary of the Invention [Problem to be solved by the invention]

[0007] It is therefore an object of the present invention to provide further malonamide compounds which have strong herbicidal activity, especially 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 unwanted plants. [Means for solving the problem]

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

[0009] Thus, the present invention provides a compound of formula (I)

[0010] [ka] wherein the substituents have the following meanings: R 1 is 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; R 2 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-alkoxy (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio; R 5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl; R 6 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R 8 is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C3-C6)-alkenyl, (C2-C6)-alkynyl , (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio; R 9 is hydrogen, (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; X is a bond (X 0 ), or (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0011] [ka] is a divalent unit from the group consisting of: R 10 ~R 15 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d , N.R. b CO2R e , R a or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, imidazolyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy; Y is hydrogen, cyano, hydroxyl, Z, or (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C2-C 12 )-alkynyl, each of which is 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 , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e Re , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e substituted with m groups from the group consisting of: Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. 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 fa 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C1-C3)-alkoxy; R b is hydrogen or R a and; R c are 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; R d is hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl, furanyl-(C1-C3)-alkyl or (C2-C4)-alkynyl (each of which is fluorine, chlorine, bromine, cyano, COR a ,CONR b R h , (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl); R e is R d and; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R his hydrogen or (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl or (C2-C4)-alkynyl (each of which is fluorine, chlorine, bromine, cyano, COR a and (C1-C2)-alkoxy); m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4, 5, or 6. Compound ( When the compound of formula (I) has a carboxyl group, including agriculturally acceptable salts, amides, esters or thioesters thereof )of provide.

[0012] The invention also relates to formulations comprising at least one compound of formula (I) and auxiliaries customary for formulating crop protection agents.

[0013] The present invention also provides combinations comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C).

[0014] The present invention also provides the use of a compound of formula (I) as a herbicide, ie for controlling undesirable vegetation.

[0015] The present invention further provides a method for controlling undesirable vegetation comprising applying a herbicidally effective amount of at least one compound of formula (I) to plants, their seeds and / or their habitat. DETAILED DESCRIPTION OF THE INVENTION

[0016] Where the compounds of formula (I), herbicidal compounds B and / or safeners C described herein can form geometric isomers (e.g. E / Z isomers), it is possible according to the invention to use both the pure isomers and mixtures thereof.

[0017] Where the compounds of formula (I), herbicidal compounds B and / or safeners C described herein have one or more chiral centers and therefore exist as enantiomers or diastereomers, it is possible according to the present invention to use both the pure enantiomers and diastereomers and mixtures thereof.

[0018] When the compounds of formula (I), herbicidal compound B and / or safener C described herein have an ionizable functional group, they can also be used in the form of their agriculturally acceptable salts. Preferred are generally salts of cations and acid addition salts of acids whose cations and anions, respectively, do not adversely affect the activity of the active compound.

[0019] Preferred cations are ions of alkali metals (preferably lithium, sodium and potassium ions), ions of alkaline earth metals (preferably calcium and magnesium ions) and ions of transition metals (preferably manganese, copper, zinc and iron ions), as well as ammonium and substituted ammonium ions in which one to four hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl (preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethyl ... butylammonium, 2-hydroxyethylammonium (olamine salts), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salts), di(2-hydroxyeth-1-yl)-ammonium (diolamine salts), tris(2-hydroxyethyl)ammonium (trolamine salts), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salts), also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium (for example trimethylsulfonium), and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally salts of polybasic amines, such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0020] Useful anions of acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0021] The compounds of formula (I), herbicidal compounds B and / or safeners C having a carboxyl group as described herein may be used in the form of the acid, in the form of an agriculturally suitable salt as described above, or else in the form of an agriculturally acceptable derivative, for example as an amide (e.g., mono- and di-C1-C6-alkylamides or arylamides), as an ester (e.g., allyl esters, propargyl esters, C1-C6 alkyl ... 10 as alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters, and also as thioesters (e.g. C1-C 10 -alkylthioesters). Preferred mono- and di-C1-C6-alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C1-C4-alkoxy-C1-C4-alkyl esters are linear or branched C1-C4-alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl esters. Linear or branched C1-C 10 An example of an -alkyl thioester is the ethyl thioester.

[0022] The terms used for organic groups in the definitions of the variables, such as the expression "halogen", are generic terms that represent the individual members of these groups of the organic unit.

[0023] prefix C x -C y indicates the number of carbon atoms possible in a particular case. All hydrocarbon chains may be straight or branched. Halogen: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine; Alkyl and the alkyl portion of composite groups, e.g., alkoxy, alkylamino, alkoxycarbonyl: saturated, linear or branched hydrocarbon groups having 1 to 10 carbon atoms, e.g., C1-C 10 - alkyl, for example, 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-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl, 2-ethylhexyl and their positional isomers; nonyl, decyl and their positional isomers; Haloalkyl: A straight or branched alkyl group (as defined above) having 1 to 10 carbon atoms, in which some or all of the hydrogen atoms are replaced by the halogen atoms defined above. In one embodiment, the alkyl group is at least once or fully substituted by a specific halogen atom, preferably fluorine, chlorine, or bromine. In a further embodiment, the alkyl group is partially or fully halogenated by different halogen atoms, and in the case of mixed halogen substitution, a combination of chlorine and fluorine is preferred. Particularly preferred are (C1-C3)-haloalkyl, more preferably (C1-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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; Alkenyl, and also the alkenyl moiety in composite groups, such as alkenyloxy: an unsaturated, linear or branched hydrocarbon group having 2 to 10 carbon atoms and one double bond in any position. According to the invention, it may be preferable to use small alkenyl groups, such as (C2-C4)-alkenyl, whereas it may be preferable to use larger alkenyl groups, such as (C5-C8)-alkenyl. Examples of alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl- 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl 4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; haloalkenyl: an alkenyl group as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, such as 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribrom-2-en-1-yl or 2,3-dibromobut-2-en-1-yl; Alkynyl and alkynyl moieties in composite groups, such as alkynyloxy: straight or branched hydrocarbon groups having 2 to 10 carbon atoms and one or two triple bonds in any position, such as C2-C6-alkynyl, for example, 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; haloalkynyl: alkynyl groups as mentioned above which are partially or fully substituted by fluorine, chlorine, bromine and / or iodine, such as 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; Cycloalkyl, and also the cycloalkyl moiety in composite groups: monocyclic or bicyclic saturated hydrocarbon groups having 3 to 10, especially 3 to 6, carbon ring members, such as C3-C6-cycloalkyl, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Examples of bicyclic groups include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl, and bicyclo[3.2.1]octyl. In this context, optionally substituted C3-C8-cycloalkyl means a cycloalkyl group having 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1, 2, 3, 4, or 5 hydrogen atoms, is replaced by a substituent that is inert under the reaction conditions. Examples of inert substituents are CN, C1-C6-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyl and C1-C4-alkoxy-C1-C6-alkyl; Halocycloalkyl, and the halocycloalkyl moiety in halocycloalkoxy, halocycloalkylcarbonyl, etc.: monocyclic saturated hydrocarbon groups (as defined above) having 3 to 10 carbon ring members in which some or all of the hydrogen atoms may be replaced by halogen atoms as defined above, particularly fluorine, chlorine and bromine; Cycloalkoxy: a cycloalkyl group as above attached via an oxygen; Alkoxy, and also the alkoxy moiety in composite groups, such as alkoxyalkyl: an alkyl group as defined above, bonded via oxygen and 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, hexoxy, 1-methylpentoxy, 2-methylprop ... propylpentoxy, 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; Haloalkoxy: Alkoxy as defined above in which some or all of the hydrogen atoms in these groups have been replaced by halogen atoms, in particular by fluorine, chlorine or bromine, as defined above under haloalkyl. Examples are OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, 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-dichloro bromopropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH—C—F, OCF—C—F, 1-(CH—F)-2-fluoroethoxy, 1-(CH—Cl)-2-chloroethoxy, 1-(CH—Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy; Hydroxyl: an OH group attached via an O atom; Cyano: A CN group attached via a C atom; Nitro: NO2 group attached through the N atom.

[0024] The preferred embodiments of the present invention mentioned hereinafter must be understood as being preferred independently of one another or in combination with one another.

[0025] According to a particular embodiment of the invention, preference is given to compounds of formula (I) in which the variables have the following meanings, independently of one another or in combination with one another:

[0026] Preferred compounds according to the present invention are those 1 is selected from the group consisting of hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy.

[0027] Preferred compounds according to the invention also include R 1 is selected from the group consisting of hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, and (C1-C3)-haloalkyl, in particular hydrogen, methyl, cyclopropyl and 2,2-difluoroethyl.

[0028] More preferred compounds according to the present invention are those 1 is selected from the group consisting of hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl and (C1-C3)-alkoxy-(C1-C3)-alkyl.

[0029] Similarly, preferred compounds according to the invention are those in which R 1 is selected from the group consisting of hydrogen, methyl and methoxymethyl.

[0030] In particular, R 1 is hydrogen.

[0031] Further preferred compounds according to the present invention are those 2 is selected from the group consisting of hydrogen, halogen and (C1-C3)-alkyl.

[0032] Preferred compounds according to the invention also include R 2is selected from the group consisting of hydrogen, halogen and (C1-C3)-alkoxy, in particular hydrogen, fluorine and methoxy.

[0033] Similarly, preferred compounds according to the invention are those in which R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

[0034] In particular, R 2 is hydrogen.

[0035] Further preferred compounds according to the present invention are those 3 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and (C1-C3)-alkyl.

[0036] Preferred compounds according to the invention also include R 3 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy.

[0037] More preferred compounds according to the present invention are those 3 is selected from the group consisting of halogen, cyano and (C1-C3)-alkyl.

[0038] Preferred compounds according to the invention also include R 3 is selected from the group consisting of halogen, cyano, and (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy.

[0039] Similarly, preferred compounds according to the invention are those in which R 3 is selected from the group consisting of hydrogen, halogen, cyano and methyl.

[0040] Similarly, preferred compounds according to the invention are those in which R 3 is selected from the group consisting of hydrogen, halogen, cyano and methyl, (C1-C3)-haloalkoxy, in particular hydrogen, halogen, trifluoromethoxy.

[0041] Similarly, preferred compounds according to the invention are those in which R 3 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and methyl.

[0042] In particular, R 3 is hydrogen or halogen, very particularly chlorine or fluorine.

[0043] Further preferred compounds according to the present invention are those 4 is selected from the group consisting of hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkylthio and (C1-C3)-haloalkylthio.

[0044] Further preferred compounds according to the present invention are those 4 is selected from the group consisting of hydrogen and halogen.

[0045] Similarly, preferred compounds according to the invention are those in which R 4 is a compound of formula (I) wherein is selected from the group consisting of hydrogen, fluorine, chlorine and bromine.

[0046] In particular, R 4 is hydrogen or hydrogen, fluorine or chlorine, very particularly hydrogen.

[0047] Further preferred compounds according to the present invention are those 5 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and (C1-C3)-alkyl.

[0048] Preferred compounds according to the invention also include R 5is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy.

[0049] More preferred compounds according to the present invention are those 5 is selected from the group consisting of halogen, cyano and (C1-C3)-alkyl.

[0050] Preferred compounds according to the invention also include R 5 is selected from the group consisting of halogen, cyano, and (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy.

[0051] Similarly, preferred compounds according to the invention are those in which R 5 is selected from the group consisting of hydrogen, halogen, cyano and methyl.

[0052] Similarly, preferred compounds according to the invention are those in which R 5 is selected from the group consisting of hydrogen, halogen, cyano and methyl, (C1-C3)-haloalkoxy, in particular hydrogen, halogen, trifluoromethoxy.

[0053] Similarly, preferred compounds according to the invention are those in which R 5 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and methyl.

[0054] In particular, R 5 is hydrogen or halogen, very particularly chlorine or fluorine.

[0055] Further preferred compounds according to the present invention are those 6 is selected from the group consisting of hydrogen, halogen and (C1-C3)-alkyl.

[0056] Preferred compounds according to the invention also include R 6 is selected from the group consisting of hydrogen, halogen and (C1-C3)-alkoxy, in particular hydrogen, fluorine and methoxy.

[0057] Similarly, preferred compounds according to the invention are those in which R 6 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

[0058] In particular, R 6 is hydrogen.

[0059] Further preferred compounds according to the present invention are those 7 are selected from the group consisting of (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl and (C1-C3)-alkoxy-(C1-C3)-alkyl, each of which is substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano.

[0060] Similarly, preferred compounds according to the invention are those in which R 7 is selected from the group consisting of (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl and (C3-C6)-alkynyl.

[0061] Similarly, preferred compounds according to the invention are those in which R 7 is selected from the group consisting of (C1-C6)-alkyl, (C3-C6)-cycloalkyl and (C3-C6)-alkenyl.

[0062] Similarly, preferred compounds according to the invention are those in which R 7 is selected from the group consisting of (C1-C6)-alkyl.

[0063] In particular, R 7is methyl or ethyl, very especially methyl.

[0064] Further preferred compounds according to the present invention are those 8 is selected from the group consisting of hydrogen, halogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-cycloalkyl, (C-C)-alkoxy, (C-C)-cycloalkoxy, (C-C)-haloalkoxy, (C-C)-alkenyloxy and (C-C)-alkynyloxy.

[0065] Similarly, preferred compounds according to the invention are those in which R 8 is selected from the group consisting of hydrogen, halogen, (C-C)-alkyl, (C-C)-cycloalkyl, (C-C)-alkoxy, (C-C)-cycloalkoxy, (C-C)-haloalkoxy, (C-C)-alkenyloxy and (C-C)-alkynyloxy.

[0066] Similarly, preferred compounds according to the invention are those in which R 8 is selected from the group consisting of hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and (C1-C6)-alkoxy.

[0067] More preferred compounds according to the present invention are those 8 is selected from the group consisting of hydrogen and halogen.

[0068] In particular, R 8 is hydrogen, fluorine, methyl, ethyl, methoxy or ethoxy, very especially hydrogen or fluorine, most especially hydrogen.

[0069] Further preferred compounds according to the present invention are those 9 is selected from the group consisting of hydrogen, (C1-C6)-alkyl and (C3-C6)-cycloalkyl.

[0070] Similarly, preferred compounds according to the invention are those in which R 9 is selected from the group consisting of hydrogen and (C1-C3)-alkyl.

[0071] In particular, R 9 is hydrogen, methyl or ethyl, very particularly hydrogen.

[0072] In the compounds of formula (I), X is a bond (X 0 ), or (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ) and the divalent units (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ) Orientation is as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y.

[0073] [ka]

[0074] Preferred embodiment (formula (IX) 0 ) in which X is a bond (X 0 ) is:

[0075] [ka]

[0076] Another preferred embodiment (formula (IX) 1 ) compound), X is (X 1 ) and (X 1 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0077] [ka]

[0078] Another preferred embodiment (formula (IX) 2 ) compound), X is (X 2 ) and (X 2 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0079] [ka]

[0080] Another preferred embodiment (formula (IX) 3 ) compound), X is (X 3 ) and (X 3 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0081] [ka]

[0082] Another preferred embodiment (formula (IX) 4 ) compound), X is (X 4 ) and (X 4 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0083] [ka]

[0084] Another preferred embodiment (formula (IX) 5 ) compound), X is (X5 ) and (X 5 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0085] [ka]

[0086] Another preferred embodiment (formula (IX) 6 ) compound), X is (X 6 ) and (X 6 ) is oriented as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

[0087] [ka]

[0088] Further preferred compounds according to the present invention are those in which X is a bond (X 0 ), or a divalent unit 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)CHO, CH2CHO, CH(cPr)CHO, CH(CHOCH3), CH(CH2CH2SCH3), CH(COOH), CH(COOCH3), CH(COOH)CH2, CH(COOCH3)CH2, CH2COH(CF3), CH(CONHCH3), CH(CONHCH3)CH2 and CH2CH2CONHCH2.

[0089] Further preferred compounds according to the present invention are those 10 ~R 15 are independently 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 groups 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 groups from the group consisting of fluorine).

[0090] Similarly, preferred compounds according to the invention are those in which R 10 ~R 15 are independently 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 groups from the group consisting of fluorine), or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy (each substituted by m groups from the group consisting of fluorine).

[0091] Similarly, preferred compounds according to the invention are those in which R 10 ~R 15 However, each independently represents hydrogen, fluorine, chlorine, and CO2R e ,CONR b R d or (C1-C6)-alkyl (substituted by m groups from the group consisting of fluorine), or (C1-C6)-alkoxy (substituted by m groups from the group consisting of fluorine).

[0092] In particular, R 10 ~R15 are each independently halogen, (C-C)-alkyl, (C-C)-alkoxy and COR e is selected from the group consisting of:

[0093] Further preferred compounds according to the invention are those in which Y is hydrogen, cyano, hydroxyl, Z, or (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C2-C 12 )-alkynyl (respectively fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO2R e and CONR b R h and m groups selected from the group consisting of:

[0094] Likewise, preferred compounds according to the invention are those in which Y is hydrogen, cyano, hydroxyl, Z, or (C1-C 12 )-alkyl and (C3-C8)-cycloalkyl (respectively fluorine, CO2R e and CONR b R h and m groups selected from the group consisting of:

[0095] Likewise, preferred compounds according to the invention are those in which Y is (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C-C 12 )-alkynyl, each of which is 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 , C.O.R.b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. 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 is a compound of formula (I) substituted with m groups from the group consisting of:

[0096] Likewise, preferred compounds according to the invention are those in which Y is (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C-C 12 )-alkynyl, each of which is selected from the group consisting of fluorine and COR e is a compound of formula (I) substituted with m groups from the group consisting of:

[0097] In particular, Y is Z or (C1-C 12 )-alkyl and (C3-C8)-cycloalkyl (respectively fluorine, (C1-C2)-alkoxy, CO2R e and CONR b R h and m groups selected from the group consisting of:

[0098] According to one preferred embodiment, Y is Z.

[0099] Preferred compounds according to the invention are those in which Z is selected from the group consisting of 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings (excluding phenyl) formed from r carbon atoms and n oxygen atoms, each of which is COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. 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 a carbon atom bearing n oxo groups.

[0100] Likewise, preferred compounds according to the invention are those in which Z is selected from the group consisting of 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings (excluding phenyl) formed from r carbon atoms and n oxygen atoms, each of which is COR e ,CONR b R h , R b , R c , Re and R f and a carbon atom bearing n oxo groups.

[0101] Further preferred compounds according to the invention are those in which Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and COR e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f and wherein the sulfur and carbon atoms bear n oxo groups.

[0102] Further preferred compounds according to the invention are those in which Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and COR e ,CONR b R h , R b , R c , R e and R f and wherein the sulfur and carbon atoms bear n oxo groups.

[0103] Representative examples of the above 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0104] [ka]

[0105] Representative examples of the above 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0106] [ka]

[0107] Likewise, preferred compounds according to the invention are those in which Z is selected from the group consisting of 4- or 5-membered saturated or partially unsaturated rings formed from r carbon atoms and n oxygen atoms, each of which is COR e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f is a compound of formula (I) substituted with m groups from the group consisting of:

[0108] Likewise, preferred compounds according to the invention are those in which Z is selected from the group consisting of 4- or 5-membered saturated or partially unsaturated rings formed from r carbon atoms and n oxygen atoms, each of which is COR e ,CONR b R h , R b , R c , R e and R f is a compound of formula (I) substituted with m groups from the group consisting of:

[0109] Likewise, preferred compounds according to the invention are those in which Z is selected from the group consisting of five-membered saturated or partially unsaturated rings formed from four carbon atoms and one oxygen atom, each of which is COR e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R fis a compound of formula (I) substituted with m groups from the group consisting of:

[0110] Likewise, preferred compounds according to the invention are those in which Z is selected from the group consisting of five-membered saturated or partially unsaturated rings formed from four carbon atoms and one oxygen atom, each of which is COR e ,CONR b R h , R b , R c , R e and R f is a compound of formula (I) substituted with m groups from the group consisting of:

[0111] Each of these is the CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f Representative examples of five-membered saturated or partially unsaturated rings formed from four carbon atoms and one oxygen atom, substituted with m groups from the group consisting of are the following structures, in which the arrows indicate the bond to any of the depicted substituents:

[0112] [ka]

[0113] Each of these is the CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f A preferred example of a five-membered saturated or partially unsaturated ring formed from four carbon atoms and one oxygen atom, substituted by m groups from the group consisting of:e Show the bond to:

[0114] [ka]

[0115] Each of these is the CO2R e ,CONR b R h , R b , R c , R e and R f A preferred example of a five-membered saturated or partially unsaturated ring formed from four carbon atoms and one oxygen atom, substituted by m groups from the group consisting of: e Show the bond to:

[0116] [ka]

[0117] Likewise, preferred compounds according to the invention are those in which Z is It is made up of five carbon atoms 5-membered saturated or partially unsaturated rings, each of which is selected from the group consisting of COR e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f is substituted with m groups from the group consisting of ,formula (I)

[0118] Similarly, preferred compounds according to the invention are those in which Z is selected from the group consisting of five-membered saturated or partially unsaturated rings formed from five carbon atoms, each of which is COR e ,CONR b R h , R b , R c , R e and Rf is a compound of formula (I) substituted with m groups from the group consisting of:

[0119] Each of these is the CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f Representative examples of 5-membered saturated or partially unsaturated rings formed from 5 carbon atoms substituted with m groups from the group consisting of are the following structures, in which the arrows indicate the bond to any of the depicted substituents:

[0120] [ka]

[0121] Each of these is the CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f A preferred example of a 5-membered saturated or partially unsaturated ring formed from 5 carbon atoms substituted by m groups from the group consisting of: e Show the bond to:

[0122] [ka]

[0123] Each of these is the CO2R e ,CONR b R h , R b , R c , R e and R fA preferred example of a 5-membered saturated or partially unsaturated ring formed from 5 carbon atoms substituted by m groups from the group consisting of: e Show the bond to:

[0124] [ka]

[0125] In particular, Z is selected from the group consisting of cyclobutyl, cyclopentyl, cyclopentenyl, and tetrahydrofuranyl, each of which is COR e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f is substituted with m groups from the group consisting of:

[0126] Very particularly, Z is selected from the group consisting of cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each of which is COR e ,CONR b R h , R b , R c , R e and R f is substituted with m groups from the group consisting of:

[0127] Each of these is the CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R fPreferred examples Z.1 to Z.5 are the following structures, where arrow (1) represents the point of attachment to X, and arrows (2) and (3) represent the points of attachment to any of the described substituents, in particular COR: e ,CONR b R h , R b , R c , R e and R f Show the bond to:

[0128] [ka]

[0129] Preferred compounds of the invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is 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; R 2 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl; R 4is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R 8is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl , (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio; R 9 is hydrogen, (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; X is a bond (X 0 ), or (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0130] [ka] is a divalent unit from the group consisting of: R 10 ~R 15 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d , R aor (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, each of which is substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, each of which is substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy; Y is hydrogen, cyano, hydroxyl, Z, or (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C2-C 12 )-alkynyl, each of which is 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 , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e NR b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(Rb )=NOR e substituted with m groups from the group consisting of: Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , R b , R c , R e and R f a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (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 hydroxy; R b is hydrogen or R a and; R c are 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; R d is 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; R e is R d and; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; Rh is 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4, 5 or 6.

[0131] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R 3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is Z; Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , R b , R c , R e and R f a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (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 hydroxy; R b is 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 hydroxy; R c are 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; R e is 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R his 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; r is 1, 2, 3, 4, 5 or 6; n is 0, 1 or 2; m is 0, 1, 2, 3, 4 or 5.

[0132] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R 3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is Z; Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R e is 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, bromine, cyano and (C1-C2)-alkoxy; r is 1, 2, 3, 4, 5 or 6; n is 0, 1 or 2; m is 0, 1, 2, 3, 4 or 5.

[0133] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R 3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is Z; Z is CO2R e ,CONR b R h , R b , R c , R e and R f a 5-membered saturated, partially unsaturated or fully unsaturated carbocyclic ring substituted with m groups from the group consisting of: R a is (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 hydroxy; R b is 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 hydroxy; R c are 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; R eis 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; m is 0, 1, 2 or 3.

[0134] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R 3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is Z; Z is CO2R e and R b a 5-membered saturated, partially unsaturated or fully unsaturated carbocyclic ring substituted with m groups from the group consisting of: R b is hydrogen or (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 hydroxy; R e is 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, bromine, cyano and (C1-C2)-alkoxy; m is 0, 1 or 2.

[0135] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R 3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl, each of which is selected from the group consisting of fluorine and COR e substituted with m groups from the group consisting of: R e is 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; m is 0, 1 or 2.

[0136] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, preferably hydrogen, (C1-C3)-alkyl or (C3-C4)-cycloalkyl, more preferably hydrogen; R 2 is hydrogen; R3 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 4 is hydrogen or fluorine, preferably hydrogen; R 5 is halogen, cyano, (C1-C3)-alkyl, preferably fluorine or chlorine; R 6 is hydrogen; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, preferably (C1-C6)-alkyl, more preferably methyl; R 8 is hydrogen or halogen, preferably hydrogen; R 9 is hydrogen; X is a bond; Y is (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl, each of which is 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 , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e NR b SO2NR b R e , OCONR b R e , OCSNRb R e , POR f R f and C(R b )=NOR e substituted with m groups from the group consisting of: Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , R b , R c , R e and R f a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (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 hydroxy; R b is 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 hydroxy; R c are 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; R dis 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; R e is 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; r is 1, 2, 3, 4, 5 or 6; m is 0, 1 or 2; n is 0, 1 or 2.

[0137] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is 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; R 2is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is methyl; R 8 is hydrogen or fluorine; R 9 is hydrogen, (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; X is a bond (X 0 ) or (X 1 ), (X 2 ), (X 3 ), (X4 ), (X 5 ) and (X 6 ):

[0138] [ka] is a divalent unit from the group consisting of: R 10 ~R 15 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d , R a or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, each of which is substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, each of which is substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy; Y is hydrogen, cyano, hydroxyl, Z, or (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C2-C 12 )-alkynyl, each of which is 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 , C.O.R. b ,CONR e SO2R a , N.R. b R e, N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. 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 substituted with m groups from the group consisting of: Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , R b , R c , R e and R f a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (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 hydroxy; R b is hydrogen or R a and; R c are 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; R d is 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; R e is R d and; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4, 5 or 6.

[0139] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is 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; R 2 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is methyl; R 8 is hydrogen or fluorine; R 9 is hydrogen, (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; X is a bond; Y is Z or (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl, each of which is fluorine, CO2R e and CONR e SO2R a substituted with m groups from the group consisting of: Z is formed from r carbon atoms and n oxygen atoms, and CO2R e ,CONR b R h ,CONR e SO2R a , R b , R c , R e and R f a 4- to 5-membered saturated or partially unsaturated ring substituted with m groups selected from the group consisting of: R a is (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 hydroxy; R b is hydrogen or (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 hydroxy; R c are 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; R e is 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R his 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4 or 5.

[0140] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1 is 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; R 2 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is methyl; R 8 is hydrogen or fluorine; R 9 is hydrogen, (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; X is a bond; Y is Z or (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl, each of which is selected from fluorine and COR e substituted with m groups from the group consisting of: Z is formed from r carbon atoms and n oxygen atoms, and CO2R e ,CONR b R h , R b , R c , R e and R f a 4- to 5-membered saturated or partially unsaturated ring substituted with m groups selected from the group consisting of: R a is (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 hydroxy; R b is hydrogen or (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 hydroxy; R c are 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; R e is 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4 or 5.

[0141] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1is 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; R 2 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R 8is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl , (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio; R 9 is hydrogen, (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; X is a bond; Y is Z; Z is formed from r carbon atoms and n oxygen atoms, and CO2R e ,CONR b R h , R b , R c , R e and R f a 4- to 5-membered saturated or partially unsaturated ring substituted with m groups selected from the group consisting of: R a is (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 hydroxy; R bis hydrogen or (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 hydroxy; R c are 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; R e is 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; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4 or 5.

[0142] Further preferred compounds of the present invention are compounds of formula (I) in which the substituents have the following meanings: R 1is 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; R 2 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 5 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R 6 is hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R 8is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl , (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio; R 9 is hydrogen, (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; X is a bond; Y is (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C-C 12 )-alkynyl, each of which is 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 , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R.b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. 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 substituted with m groups from the group consisting of: Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , R b , R c , R e and R f a 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring (excluding phenyl) substituted by m groups from the group consisting of: R a is (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 hydroxy; R b is hydrogen or R a and; R c are 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; R d is 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; R e is R d and; R f is (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is 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; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4, 5 or 6.

[0143] Further preferred embodiments (II to I.IV) of the compounds of formula (I) are (II): R 1 , R 9 is hydrogen:

[0144] [ka] (I.II): R 1 is hydrogen and R 9 is methyl:

[0145] [ka] (I.III): R 1 is methyl and R 9 is methyl:

[0146] [ka] (I.IV): R 1 is methyl and R 9 is hydrogen:

[0147] [ka] It is a compound.

[0148] R 1 , R 2 , R 6 and R 9 Particularly preferred are compounds of formula (IIa) in which:

[0149] [ka]

[0150] R 1 , R 2 , R 4 , R 6 and R 9 Also particularly preferred are compounds of formula (IIb) in which:

[0151] [ka]

[0152] R 1 , R 2 , R 6 and R 9 is hydrogen and X is a bond (X 0 ) and Y is Z. Particularly preferred are compounds of formula (IIc):

[0153] [ka]

[0154] R 1 , R 2, R 4 , R 6 and R 9 is hydrogen and X is a bond (X 0 ) and Y is Z. Compounds of formula (IId) are also particularly preferred:

[0155] [ka]

[0156] R 1 , R 2 , R 6 is hydrogen and R 9 Also particularly preferred are compounds of formula (I.II.a) in which is methyl:

[0157] [ka]

[0158] R 1 , R 2 , R 4 , R 6 is hydrogen and R 9 Also particularly preferred are compounds of formula (I.II.b) in which R is methyl: and R 9

[0159] [ka]

[0160] R 2 , R 6 is hydrogen and R 1 , R 9 Also particularly preferred are compounds of formula (I.III.a) in which is methyl:

[0161] [ka]

[0162] R 2 , R 4 , R 6is hydrogen and R 1 , R 9 Also particularly preferred are compounds of formula (I.III.b) in which is methyl:

[0163] [ka]

[0164] R 1 is methyl and R 2 , R 6 and R 9 Also particularly preferred are compounds of formula (I.IV.a) in which:

[0165] [ka]

[0166] R 1 is methyl and R 2 , R 4 , R 6 and R 9 Also particularly preferred are compounds of formula (I.IV.b) in which:

[0167] [ka]

[0168] In the context of the present invention, R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 below.

[0169] [Table 1] TIFF0007757297000037.tif255169TIFF0007757297000038.tif255170TIFF000 7757297000039.tif255170TIFF0007757297000040.tif255170TIFF00077572970 00041.tif255170TIFF0007757297000042.tif255170TIFF0007757297000043.t if255170TIFF0007757297000044.tif255170TIFF0007757297000045.tif255170 TIFF0007757297000046.tif252170TIFF0007757297000047.tif252170TIFF000 7757297000048.tif252170TIFF0007757297000049.tif252170TIFF00077572970 00050.tif252170TIFF0007757297000051.tif252170TIFF0007757297000052.t if252170TIFF0007757297000053.tif252170TIFF0007757297000054.tif160170

[0170] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.1.1 to I.1.1152:

[0171] [ka]

[0172] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3, R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.2.1 to I.2.1152:

[0173] [ka]

[0174] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.3.1 to I.3.1152:

[0175] [ka]

[0176] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.4.1 to I.4.1152:

[0177] [ka]

[0178] R 1 , R 2 , R 6 and R9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.5.1 to I.5.1152:

[0179] [ka]

[0180] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.6.1 to I.6.1152:

[0181] [ka]

[0182] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.7.1 to I.7.1152:

[0183] [ka]

[0184] R 1 , R2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.8.1 to I.8.1152:

[0185] [ka]

[0186] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.9.1 to I.9.1152:

[0187] [ka]

[0188] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.10.1 to I.10.1152:

[0189] [ka]

[0190] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.11.1 to I.11.1152:

[0191] [ka]

[0192] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.12.1 to I.12.1152:

[0193] [ka]

[0194] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.13.1 to I.13.1152:

[0195] [ka]

[0196] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.14.1 to I.14.1152:

[0197] [ka]

[0198] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.15.1 to I.15.1152:

[0199] [ka]

[0200] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.16.1 to I.16.1152:

[0201] [ka]

[0202] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.17.1 to I.17.1152:

[0203] [ka]

[0204] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.18.1 to I.18.1152:

[0205] [ka]

[0206] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.19.1 to I.19.1152:

[0207] [ka]

[0208] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.20.1 to I.20.1152:

[0209] [ka]

[0210] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.21.1 to I.21.1152:

[0211] [ka]

[0212] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.22.1 to I.22.1152:

[0213] [ka]

[0214] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.23.1 to I.23.1152:

[0215] [ka]

[0216] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.24.1 to I.24.1152:

[0217] [ka]

[0218] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.25.1 to I.25.1152:

[0219] [ka]

[0220] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.26.1 to I.26.1152:

[0221] [ka]

[0222] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.27.1 to I.27.1152:

[0223] [ka]

[0224] R 1 , R 2 , R 6 and R 9is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.28.1 to I.28.1152:

[0225] [ka]

[0226] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.29.1 to I.29.1152:

[0227] [ka]

[0228] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.30.1 to I.30.1152:

[0229] [ka]

[0230] R 1 , R2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.31.1 to I.31.1152:

[0231] [ka]

[0232] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.32.1 to I.32.1152:

[0233] [ka]

[0234] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.33.1 to I.33.1152:

[0235] [ka]

[0236] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.34.1 to I.34.1152:

[0237] [ka]

[0238] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.35.1 to I.35.1152:

[0239] [ka]

[0240] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.36.1 to I.36.1152:

[0241] [ka]

[0242] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.37.1 to I.37.1152:

[0243] [ka]

[0244] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.38.1 to I.38.1152:

[0245] [ka]

[0246] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.39.1 to I.39.1152:

[0247] [ka]

[0248] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.40.1 to I.40.1152:

[0249] [ka]

[0250] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.41.1 to I.41.1152:

[0251] [ka]

[0252] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.42.1 to I.42.1152:

[0253] [ka]

[0254] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.43.1 to I.43.1152:

[0255] [ka]

[0256] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.44.1 to I.44.1152:

[0257] [ka]

[0258] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.45.1 to I.45.1152:

[0259] [ka]

[0260] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.46.1 to I.46.1152:

[0261] [ka]

[0262] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.47.1 to I.47.1152:

[0263] [ka]

[0264] R 1 , R 2 , R 6 and R 9is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.48.1 to I.48.1152:

[0265] [ka]

[0266] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.49.1 to I.49.1152:

[0267] [ka]

[0268] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.50.1 to I.50.1152:

[0269] [ka]

[0270] R 1 , R2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.51.1 to I.51.1152:

[0271] [ka]

[0272] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.52.1 to I.52.1152:

[0273] [ka]

[0274] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.53.1 to I.53.1152:

[0275] [ka]

[0276] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.54.1 to I.54.1152:

[0277] [ka]

[0278] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.55.1 to I.55.1152:

[0279] [ka]

[0280] R 1 , R 2 , R 6 and R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 has the meaning defined in rows 1 to 1152 of Table 1 above, i.e. the individual compounds I.56.1 to I.56.1152:

[0281] [ka]

[0282] The compounds of formula (I) according to the invention can be prepared by standard methods of organic chemistry, for example by the following process:

[0283] [ka]

[0284] The compounds of formula (I) can be prepared according to or in analogy with methods described in the prior art, and the synthesis utilizes starting materials that are commercially available or can be prepared according to conventional procedures starting from readily available compounds.

[0285] Compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling reagent. Thus, compounds of formula (I) can be synthesized from the corresponding carboxylic acid (1 equivalent) using a coupling reagent (1-2 equivalents), such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), an organic base (1-3 equivalents), and an amine (II) (1-3 equivalents). The reaction is typically 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 a temperature between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[0286] [ka]

[0287] Carboxylic acids (III) are commercially available or can be prepared by the corresponding esters (IV) (R P R is alkyl or benzyl. P When R is alkyl, the ester (IV) can be cleaved using aqueous alkali metal hydroxide. Preferably, lithium hydroxide, sodium hydroxide, or potassium hydroxide (1-2 equivalents) is used. The reaction is typically 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. Preferably, the reaction is carried out at room temperature. p When (IV) is benzyl, the ester can be cleaved using palladium on charcoal (0.001 to 1 equivalent) as a catalyst and hydrogen gas at temperatures between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol, or ethanol is used.

[0288] [ka]

[0289] Compounds of formula (IV) can be prepared from carboxylic acids (VI) and commercially available amines (V) using a base and a coupling reagent. Thus, compounds of formula (IV) can be synthesized from the corresponding carboxylic acid (1 equivalent) using a coupling reagent (1-2 equivalents), such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), an organic base (1-3 equivalents), and an amine (V) (1-3 equivalents). The reaction is typically 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 a temperature 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.

[0290] [ka]

[0291] Carboxylic acids (VI) can be prepared from the corresponding diesters by selective cleavage of one ester group. q When is an alkyl ester, selective ester cleavage can be achieved using an aqueous base. Preferably, an alkali metal hydroxide is used. Most preferably, lithium hydroxide, sodium hydroxide, or potassium hydroxide is used. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, THF, methanol, or acetonitrile is used. The reaction is carried out at a temperature between 0°C and 100°C, preferably at room temperature.

[0292] Alternatively, trimethyltin hydroxide (e.g., 1 equivalent) in 1,2-dichloroethane can be used at room temperature to reflux, preferably at reflux (as described in Angew. Chem. Int., ed., 2005, 44: 1378-1382). qWhen (VII) is benzyl, the ester can be cleaved using palladium on charcoal (0.001 to 1 equivalent) as a catalyst and hydrogen gas at temperatures between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol, or ethanol is used.

[0293] [ka]

[0294] The diester (VII) is commercially available or can be prepared by the reaction of dirhodium tetraacetate ([Rh(OAc)2]2) (0.001-0.1 equivalents) and the alcohol HO-R 7 alkoxymalonates (VII) (R 8 =H) can be obtained. The reaction is typically carried out in an organic solvent, preferably toluene, at temperatures between 0°C and 100°C. Preferably, the reaction is carried out at 60°C as described in Angew. Chem. Int., ed., 2014, 53, 14230-14234. If the diazo compound (VIII) is not commercially available, it can be prepared as described in Angew. Chem. Int., ed., 2014, 53, 14230-14234.

[0295] [ka]

[0296] Alternatively, diester (VII) can be synthesized from commercially available monoester (XI), a base, and chloroformate (XII) (1-3 equivalents) as described in Bioorganic & Medicinal Chemistry Letters, 12(11), 1501-1505; 2002. The reaction is typically carried out in an organic solvent, preferably tetrahydrofuran. Suitable temperatures range from -78°C to 25°C. Preferably, the reaction is allowed to warm from -78°C to 25°C over a period of 16 hours. Preferably, lithium diisopropylamide (1 equivalent) is used as the base.

[0297] Alternatively, R 8 The diester (VII) in which is fluorine can be prepared from the corresponding non-fluorinated malonate using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)(Selectfluor) as described in WO 12 / 129384. Water and / or an organic solvent can be used. Preferably, the reaction is carried out in acetonitrile. The reaction is carried out using 1 to 4 equivalents of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)(Selectfluor) at temperatures between 0°C and reflux, preferably 60°C. 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).

[0298] [ka]

[0299] The amine of formula (XIII) can be prepared from lactam (XIV), which is commercially available or can be prepared by alkylation as described in Org. Process Res. Dev. 2018, 22, 337-343, and commercially available alcohol (XV), using thionyl chloride (2 equivalents) as described in Tetrahedron Lett. 2001, 42, 1347-1350. The reaction is typically carried out in the coupling alcohol (XV) as a solvent. The reaction is carried out at a temperature between 0°C and reflux. Preferably, the reaction is carried out at room temperature.

[0300] To broaden the spectrum of action, the compounds of formula (I) may be mixed with many representatives of other herbicidal or growth-regulating active ingredients and then applied simultaneously. Suitable ingredients for combination include, for example, acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridyliums, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyridinone ... Herbicides belong to the following classes: pyrazolins, phenylpyridazines, phosphinates, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, and ureas.

[0301] It may be more advantageous to apply the compound of formula (I) alone or in combination with other herbicides, or otherwise in the form of a mixture with other crop protection agents, for example, together with the agent for controlling pests or plant pathogenic fungi or bacteria.Also, the compatibility with the inorganic salt solution used to treat nutrient deficiency and trace element deficiency is also interesting.Other additives, such as non-phytotoxic oils and oil concentrates, can also be added.

[0302] In one embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) (compound A or component A) and at least one further active compound selected from herbicides B, preferably herbicides B of classes b1) to b15) (compound B), and safeners C (compound C).

[0303] In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one further active compound B (herbicide B).

[0304] Examples of herbicides B that can be used in combination with compounds A of formula (I) according to the invention are:

[0305] b1) From the group of the lipid biosynthesis inhibitors: ACC-herbicides, such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl ), haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, 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 (CAS1033757-93-5);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS1312340-84-3);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 (CAS1312337-48-6); 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-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl(carboxylic acid methyl ester (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(carboxylic acid methyl ester); 4-(4'-chloro-4-ethyl-2'-fluoro[1,4-(2',4'-dichloro-4-ethyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl(carboxylic acid methyl ester (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(carboxylic acid methyl ester (CAS 1033760-58-5); and non-ACC herbicides, such as benfuresate, butyrate, cycloate ), dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazil, triallate, and vernolate;

[0306] b2) From the group of ALS inhibitors: Sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron hametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron n), halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron (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, trifloxysulfuron, 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, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, Pyrimidinyl benzoates, for example, bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4 -[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid 1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), Sulfonylaminocarbonyl-triazolinone herbicides, such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, and thiencarbazone-methyl; and triafamone. Among these, preferred embodiments of the present invention relate to compositions comprising at least one imidazolinone herbicide;

[0307] b3) From the group of photosynthesis inhibitors: Amicarbazone, inhibitors of photosystem II, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-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-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), chlorotriazines, triazinones, triazindiones,Triazine herbicides such as methylthiotriazine and pyridazinone herbicides, for example, ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometham prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron ron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron hiadiazuron, phenylcarbamates 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, as well as bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil, and inhibitors of photosystem I, such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Among these, preferred embodiments of the present invention relate to compositions comprising at least one aryl urea herbicide. Among these, preferred embodiments of the present invention relate to compositions comprising at least one triazine herbicide. Among these, preferred embodiments of the present invention relate to compositions comprising at least one nitrile herbicide;

[0308] b4) From the group of the protoporphyrinogen-IX oxidase inhibitors: Acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen fen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen ), fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole ol), pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiafenacil, 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]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-diol 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-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]oxazin-6-yl)-1H- pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3 ,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetic acid ethyl ester (CAS 158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl- 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-( trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (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-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[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);

[0309] b5) From the group of bleaching herbicides: 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, fenquinotrione, and isoxaflutole e), mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, whitening agents, unknown targets: aclonifen, amitrole, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);

[0310] b6) From the group of the EPSP synthase inhibitors: Glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimesium (sulfosate);

[0311] b7) From the group of the glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium;

[0312] b8) From the group of the DHP synthase inhibitors: Aslam;

[0313] b9) From the group of the mitotic inhibitors: Compounds of group K1: 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; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham, among which compounds of group K1, in particular dinitroanilines, are preferred;

[0314] b10) From the group of the VLCFA inhibitors: Chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor; oxyacetanilides such as flufenacet ) and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and naproamide-M, tetrazolinones such as fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, and compounds of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9:

[0315] [ka] an isoxazoline compound of the formula (Isoxazoline compounds of formula (II) are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576); Among the VLCFA inhibitors, chloroacetamides and oxyacetamides are preferred;

[0316] b11) From the group of the cellulose biosynthesis inhibitors: Chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, and 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS175899-01-1);

[0317] b12) From the group of the decoupler herbicides: Dinoseb, dinoterb and DNOC and its salts;

[0318] b13) From the group of the auxin herbicides: 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-hydroxypropyl)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 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, quinclorac, 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-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);

[0319] b14) From the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

[0320] b15) From the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-methylsulfate (d ifenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine tetofurpyrolimet, and tridiphane.

[0321] Furthermore, it may be useful to apply the compound of formula (I) in combination with a safener. A safener is a chemical compound that prevents or reduces damage to useful plants without significantly affecting the herbicidal action of the compound of formula (I) on undesirable vegetation. They can be applied before sowing (for example, as a seed treatment, to shoots or seedlings), or as a pre-emergence or post-emergence application of useful plants. The safener and the compound of formula (I), and optionally herbicide B, can be applied simultaneously or sequentially.

[0322] In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one safener C (component C).

[0323] Examples of safeners are (quinolin-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide, alpha-oximinophenylacetonitrile, acetophenone oxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic acid amide, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, phosphorthiolate and N-alkyl-O-phenylcarbamates, and agriculturally acceptable salts thereof and agriculturally acceptable derivatives thereof, such as amides, esters and thioesters, which contain an acid group.

[0324] Examples of safener compounds C include benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, furilazole, 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).

[0325] The active compounds B and C of groups b1) to b15) are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Vol. 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R.R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W.H. Ahrens, Herbicide Handbook, 7th ed., Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement to the 7th ed., 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 MON4660.

[0326] The assignment of active compounds to each mode of action is based on current knowledge. If several modes of action apply to one active compound, the substance was assigned to only one mode of action.

[0327] The present invention also relates to a formulation comprising at least an auxiliary agent and at least one compound of formula (I) according to the invention.

[0328] The formulations contain a pesticidally effective amount of a compound of formula (I). The term "effective amount" refers to an amount of a combination or compound of formula (I) that is sufficient to control undesirable vegetation, especially in crops (i.e., cultivated plants), but does not cause substantial damage to the treated crop plants. This amount can vary widely and is determined by various factors, such as the undesirable vegetation to be controlled, the crop plants or materials to be treated, the climatic conditions, and the particular compound of formula (I) used.

[0329] The compounds of formula (I), their salts, amides, esters, or thioesters can be converted into conventional formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compacts, capsules, and mixtures thereof. Examples of formulation types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, fragrances, wettable powders or wettable dusts (e.g., WP, SP, WS, DP, DS), compacts (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticide products (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials, such as seeds. These and other formulation types are defined in "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, 6th Edition, May 2008, CropLife International.

[0330] The formulations are prepared in a known manner, such as the method described by Mollet and Grubemann in Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles in New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0331] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizing agents, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0332] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions (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., lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone); fatty acids; phosphonates; amines; amides (e.g., N-methylpyrrolidone, fatty acid dimethylamides); and mixtures thereof.

[0333] Suitable solid carriers or fillers are mineral earths (e.g. silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide); polysaccharides (e.g. cellulose, starch); fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea); products of plant origin (e.g. grain flour, bark flour, wood flour, nut shell flour), and mixtures thereof.

[0334] Suitable surfactants are surface-active compounds, such as anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, (2008) (International Edition or North American Edition).

[0335] Suitable anionic surfactants are alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates, and mixtures thereof. Examples of sulfonates include alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates include phosphoric acid esters. Examples of carboxylates include alkyl carboxylates, as well as carboxylated alcohol or alkylphenol ethoxylates.

[0336] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that are alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide (preferably ethylene oxide) can be used for alkoxylation. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants include homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0337] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0338] Suitable adjuvants are compounds that have negligible or no pesticidal activity themselves, but enhance the biological performance of the compound of formula (I) against the target. Examples include surfactants, mineral or vegetable oils, and other adjuvants. Further examples are listed by Knowles in "Adjuvants and additives," Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0339] Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified clays), polycarboxylates and silicates.

[0340] Preferred bactericides are bronopol and isothiazolinone derivatives (such as alkylisothiazolinones and benzisothiazolinones).

[0341] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[0342] Suitable antifoaming agents are silicones, long chain alcohols and salts of fatty acids.

[0343] Suitable colorants (e.g., red, blue, or green colorants) are low-water-soluble pigments and water-soluble dyes, including inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[0344] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0345] Examples of formulation types and their preparation are as follows:

[0346] i) Water-soluble concentrates (SL, LS) 10 to 60% by weight of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), and 5 to 15% by weight of a wetting agent (e.g., alcohol alkoxylate) are dissolved in up to 100% by weight of water and / or a water-soluble solvent (e.g., alcohol). The active substance dissolves upon dilution with water.

[0347] ii) Dispersible concentrates (DC) 5 to 25% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), and 1 to 10% by weight of a dispersant (e.g. polyvinylpyrrolidone) are dissolved in up to 100% by weight of an organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.

[0348] iii) Emulsifiable concentrates (EC) 15 to 70% by weight of a compound of formula (I) according to the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), and 5 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). Dilution with water gives an emulsion.

[0349] iv) Emulsions (EW, EO, ES) 5 to 40% by weight of a compound of formula (I) according to the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), and 1 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). This mixture is introduced into up to 100% by weight of water using an emulsifier to form a uniform emulsion. Dilution with water results in an emulsion.

[0350] v) Suspensions (SC, OD, FS) In a ball mill under stirring, 20 to 60% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is milled with 2 to 10% by weight of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1 to 2% by weight of a thickener (e.g., xanthan gum), and up to 100% by weight of water, to obtain a fine suspension of the active substance. Dilution with water results in a stable suspension of the active substance. FS-type formulations may contain up to 40% by weight of a binder (e.g., polyvinyl alcohol).

[0351] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50 to 80% by weight of a compound of formula (I) according to the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is milled with up to 100% by weight of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules using specialized equipment (e.g., extruders, spray towers, fluidized beds). Dilution with water gives a stable dispersion or solution of the active substance.

[0352] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) In a rotor-stator mill, 50 to 80% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is milled with the addition of 1 to 5% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 3% by weight of a wetting agent (e.g., alcohol ethoxylate), and up to 100% by weight of a solid carrier (e.g., silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

[0353] viii) Gels (GW, GF) In a ball mill under stirring, 5 to 25% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is ground with 3 to 10% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 5% by weight of a thickener (e.g., carboxymethylcellulose) and up to 100% by weight of water, to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0354] iv) Microemulsions (MEs) 5-20% by weight of a compound of formula (I) according to the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is added to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and up to 100% water. The mixture is stirred for 1 hour, allowing a thermodynamically stable microemulsion to spontaneously form.

[0355] iv) Microcapsules (CS) An oil phase containing 5 to 50% by weight of a compound of formula (I) according to the present invention, or a combination containing at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener 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 diacrylate or triacrylate), is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5 to 50% by weight of a compound of formula (I) according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of polyamines (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to a total of 1-10 wt. %. The wt. % is relative to the total CS formulation.

[0356] ix) Dustable powders (DP, DS) 1 to 10% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is finely ground and intimately mixed with up to 100% by weight of a solid carrier (for example finely ground kaolin).

[0357] x) Granules (GR, FG) 0.5 to 30% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is pulverized and combined with up to 100% by weight of a solid carrier (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0358] xi) Ultra-low volume liquids (UL) 1 to 50% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C), is dissolved in up to 100% by weight of an organic solvent, for example an aromatic hydrocarbon.

[0359] Formulation types i) to xi) may optionally contain further auxiliaries (for example 0.1 to 1% by weight of bactericides, 5 to 15% by weight of antifreeze agents, 0.1 to 1% by weight of antifoaming agents, and 0.1 to 1% by weight of colorants).

[0360] The formulations and / or combinations generally contain 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 formula (I).

[0361] The compound of formula (I) is used at a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

[0362] Seed treatment solutions (LS), suspoemulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible slurry powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used for the treatment of plant propagation material, especially seeds. After 2-10-fold dilution, the formulations give active substance concentrations of 0.01-60% by weight, preferably 0.1-40% by weight, in the ready-to-use preparations. (Scroll down)

[0363] Methods for applying the compounds of formula (I), formulations and / or combinations thereof to plant propagation material (especially seeds) include dressing, coating, pelleting, dusting, soaking and in-furrow application of the propagation material. Preferably, the compounds of formula (I), formulations and / or combinations thereof are applied to the plant propagation material in a manner that does not induce germination (e.g., by seed dressing, seed pelleting, seed coating and seed dusting), respectively.

[0364] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the compounds of formula (I), formulations and / or combinations containing them as premixes or, if appropriate, immediately before use (tank mix). These agents can be mixed with the formulations according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0365] The user typically applies the compounds of formula (I) according to the present invention, formulations and combinations containing them from a pre-dosage device, backpack sprayer, spray tank, spray aircraft, or irrigation system. Typically, the formulation is adjusted to the desired application concentration with water, buffers, and / or further auxiliaries, thus providing a ready-to-use spray solution or formulation according to the present invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray solution are applied per hectare of agriculturally useful area.

[0366] According to one embodiment, either the individual components of the formulation according to the invention or the partially premixed components, for example the components comprising the compound of formula (I) and optionally the active substance from group B and / or C), may be mixed by the user in a spray tank, with the addition of further auxiliaries and additives, if appropriate.

[0367] In a further embodiment, the individual components of the formulation according to the invention (e.g. part of a kit or part of a two- or three-component mixture) may be mixed by the user himself in a spray tank, with further auxiliaries added if appropriate.

[0368] In a further embodiment, either the individual components of the formulation according to the invention or the partially premixed components, e.g. the components comprising a compound of formula (I) and optionally an active substance from group B and / or C), can be applied together (e.g. after tank mixing) or sequentially.

[0369] The compounds of formula (I) are suitable as herbicides, either on their own, in suitable formulations or in combination with at least one further compound selected from herbicidally active compounds B (component B) and safeners C (component C).

[0370] The compounds of formula (I) or formulations and / or combinations containing the compounds of formula (I) very effectively control undesirable vegetation in non-crop areas, especially at high application rates. They act against broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybean and cotton without causing significant damage to the crop plants. This effect is mainly observed at low application rates.

[0371] The compounds of formula (I), or formulations and / or combinations containing them, are applied to plants primarily by spraying on the leaves. Application can be carried out by conventional spraying techniques, for example using water as a carrier and spray volumes of about 100 to 1000 l / ha (e.g., 300 to 400 l / ha). The compounds of formula (I), or formulations and / or combinations containing them, can also be applied by the low- or ultra-low-volume method or in the form of fine granules.

[0372] Application of the compounds of formula (I), or formulations and / or combinations containing same, may be carried out before, during and / or after emergence of the undesired vegetation, preferably during and / or after emergence.

[0373] The application of the compounds of formula (I) or the formulations and / or combinations can be carried out before or during sowing.

[0374] The compound of formula (I) or a formulation and / or combination comprising it can be applied before emergence, after emergence, or before planting, or together with the seeds of crop plants. It is also possible to apply the compound of formula (I) or a formulation and / or combination comprising it by applying the seeds of crop plants that have been pretreated with the compound of formula (I) or a formulation and / or combination comprising it. If the active ingredient is not well tolerated by a particular crop plant, an application technique can be used in which the combination is sprayed using a spraying device in such a way that the active ingredient reaches the leaves of undesirable vegetation growing under the crop plant or the soil surface in the open field, but does not come into contact with the leaves of sensitive crop plants as much as possible (post-directed, lay-by).

[0375] In a further embodiment, the compound of formula (I) or the formulation and / or combination comprising it can be applied by treating seeds. Seed treatment includes essentially all methods well known to those skilled in the art that are based on the compound of formula (I) or the formulation and / or combination prepared therefrom (seed dressing method, seed coating method, seed dusting method, seed soaking method, seed film coating method, seed multi-coating method, seed husk coating method, seed dripping method, and seed pelleting method). Here, the combination can be applied diluted or undiluted.

[0376] The term "seed" includes all types of seeds, such as grains, seeds, fruits, tubers, seedlings and similar forms. Preferably, the term "seed" here refers to grains and seeds. The seeds used may be seeds of the above-mentioned crop plants, but may also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0377] When used in plant protection, the amount of active substance (i.e. the compound of formula (I), component B and, if appropriate, component C) applied, without formulation auxiliaries, is, depending on the type of effect desired, between 0.001 and 2 kg per hectare, preferably between 0.005 and 2 kg per hectare, more preferably between 0.05 and 0.9 kg per hectare and in particular between 0.1 and 0.75 kg per hectare.

[0378] In another embodiment of the invention, the application rates of the compound 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 and in particular from 0.01 to 2 kg / ha of active substance (as).

[0379] In another preferred embodiment of the present invention, the application amount of the compounds of formula (I) according to the present invention (total amount of the compounds of formula (I)) is 0.1 g / ha to 3000 g / ha, preferably 10 g / ha to 1000 g / ha, depending on the control target, season, target plant and growth stage.

[0380] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is in the range of 0.1 g / ha to 5000 g / ha, also preferably in the range of 1 g / ha to 2500 g / ha, or 5 g / ha to 2000 g / ha.

[0381] In another preferred embodiment of the present invention, the application amount 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.

[0382] The required application rates of herbicidal compound B are generally in the range of from 0.0005 kg / ha to 2.5 kg / ha of active substance (as), preferably in the range of from 0.005 kg / ha to 2 kg / ha or from 0.01 kg / ha to 1.5 kg / ha.

[0383] The required application rates of safener C are generally in the range of 0.0005 kg / ha to 2.5 kg / ha of active substance (as), and preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / ha.

[0384] For the treatment of plant propagation material (e.g. seeds), for example by dusting, coating or drenching, amounts of active substance of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g per 100 kilograms of plant propagation material (preferably seeds) are generally required.

[0385] In another embodiment of the invention, for treating seeds, the amount of active substance (i.e., the compound of formula (I), component B and, if appropriate, component C) applied is generally employed in an amount of 0.001 to 10 kg per 100 kg of seeds.

[0386] When used in the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. Amounts customarily applied in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0387] In the case of the combinations according to the invention, it is immaterial whether the compound of formula (I) and the further component B and / or component C are formulated and applied together or separately.

[0388] In the case of separate applications, the order in which the applications are carried out is not particularly important: it is only necessary that the compound of formula (I) and the further component B and / or component C are applied in a time frame that allows the active ingredients to act simultaneously on the plant (preferably within a time frame of up to 14 days, in particular up to 7 days).

[0389] Depending on the application method, the compounds of formula (I) or formulations and / or combinations containing them can additionally be used to eliminate unwanted vegetation in a number of crop plants. Examples of suitable crops are: Onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), sugar beet (Beta vulgaris spec. altissima), sugar beet (Beta vulgaris spec. rapa), rapeseed (Brassica napus var. napus), rutabaga (Brassica napus var. napobrassica), Brassica rapa var.silvestris), Brassica oleracea, black mustard (Brassica nigra), tea plant (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Carya illinoinensis), lemon (Citrus limon), orange (Citrus sinensis), coffee plant (Coffea arabica), coffee plant (Coffea canephora, Coffea liberica), cucumber (Cucumis sativus), horsegrass (Cynodon dactylon), carrot (Daucus carota), oil palm (Elaeis guineensis), strawberry (Fragaria vesca), soybean (Glycine max), cotton (Gossypium hirsutum), (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), rubber tree (Hevea brasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple species (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), musa species (Musa spec.), tobacco (Nicotiana tabacum (Nicotiana rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), Norway spruce (Picea abies), pine species (Pinus spec.), Pistacia vera, peas (Pisum sativum), sweet cherry (Prunus avium), peach (Prunus persica), pears (Pyrus communis), apricots (Prunus armeniaca), sour cherry (Prunus cerasus), almonds (Prunus dulcis) and plums (Prunus domestica), gooseberry (Ribes sylvestre), castor beans (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis alba), potatoes (Solanum tuberosum), sorghum (Sorghum bicolor) (Sorghum vulgare), cocoa (Theobroma cacao) cacao), red clover (Trifolium pratense), wheat (Triticum aestivum), triticale (. Tri ticale), durum wheat (Triticum durum), broad beans (Vicia faba), grapes (Vitis vinifera), and corn (Zea mays).

[0390] Preferred crops include peanut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), Brassica oleracea, lemon (Citrus limon), orange (Citrus sinensis), coffee (Coffea arabica) (Coffea canephora, Coffea liberica), horsegrass (Cynodon dactylon), soybean (Glycine max), cotton (Gossypium hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium serrata), and safflower cotton (Gossypium serrata). vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple species (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), pistacia vera, pea (Pisum sativum), almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor) (sorghum (s.vulgare), triticale (Triticale), wheat (Triticum aestivum), durum wheat (Triticum durum), broad beans (Vicia faba), grapes (Vitis vinifera), and corn (Zea mays).

[0391] Particularly preferred crops are cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or orchard crops.

[0392] The compounds of formula (I) according to the present invention or formulations and / or combinations comprising same may also be used in crops that have been modified by mutagenesis or genetic engineering to provide new traits to the plant or to modify traits that are already present.

[0393] The term "crop plant" as used herein also includes (crop) plants that have been modified by mutagenesis or genetic engineering to provide the plant with new traits or to modify traits that are already present.

[0394] Mutagenesis includes not only random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques to create mutations at specific loci in the plant genome. Targeted mutagenesis techniques often use oligonucleotides or proteins, such as CRISPR / Cas, zinc finger nucleases, TALENs, or meganucleases, to achieve the targeted effect.

[0395] Genetic engineering typically uses recombinant DNA technology to create modifications in plant genomes that are not readily obtainable through cross-breeding, mutagenesis, or natural recombination in natural environments. Typically, one or more genes are integrated into a plant's genome to add or improve traits. These integrated genes are also referred to in the art as transgenes, and plants containing such transgenes are referred to as transgenic plants. The plant transformation process typically produces several transformation events that differ in the genomic locus at which the transgene is integrated. Plants containing a specific transgene at a specific genomic locus are typically described as containing a specific "event," referred to by the name of the specific event. Traits introduced or modified in plants include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought, among others.

[0396] Herbicide resistance has been created by using mutagenesis and genetic engineering. Plants that have been made tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding include plant varieties that are commercially available under the name Clearfield®. However, the majority of herbicide tolerance traits have been created through the use of transgenes.

[0397] Herbicide resistance has been developed to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isoxaflutole and mesotrione.

[0398] Transgenes used to provide herbicide tolerance traits include: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, and goxv247; for tolerance to glufosinate: pat and bar; for tolerance to 2,4-D: aad-1 and aad-12; for tolerance to dicamba: dmo; for tolerance to oxynil herbicides: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitor herbicides: csr1-2; for tolerance to HPPD inhibitor herbicides: hppdPF, W336, and avhppd-03.

[0399] Transgenic corn events containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-01981-5 (where the 0 is written as a stroked O in the original), 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275.

[0400] Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, GTS40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2 (where 0 is represented by a stroked O in the original), W62, W98, FG72, and CV127.

[0401] Transgenic cotton events containing herbicide resistance genes include, but are not limited to, 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.

[0402] Transgenic canola events containing herbicide tolerance genes include, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0403] Insect resistance has primarily been created by transferring bacterial genes for insecticidal proteins into plants. The most frequently used transgenes are Bacillus species toxin genes and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, genes of plant origin have also been transferred to other plants, particularly genes encoding protease inhibitors, such as CpTI and pinII. Another approach uses transgenes to generate double-stranded RNA that targets and downregulates insect genes in plants. An example for such a transgene is dvsnf7.

[0404] Transgenic corn events containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098.

[0405] Transgenic soybean events containing genes for insecticidal proteins are, for example, but not exclusive of, MON87701, MON87751 and DAS-81419.

[0406] Transgenic cotton events containing genes for insecticidal proteins are, for example, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS9124, 281-24-236, 3006-210-23, GHB119 and SGK321, but not excluding others.

[0407] Increased yield has been produced by increasing panicle biomass using the transgene athb17 present in corn event MON87403 or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0408] Crops containing modified oil content have been produced by using the transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[0409] Tolerance to abiotic conditions, particularly drought, has been created by using the transgene cspB contained in the corn event MON87460 and by using the transgene Hahb-4 contained in the soybean event IND-00410-5 (where the three Os are represented by stroked Os in the original text).

[0410] Traits are often combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combinations of traits are herbicide resistance to different groups of herbicides, insect resistance to different types of insects, especially resistance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield, and herbicide tolerance with tolerance to abiotic conditions.

[0411] Plants containing single or stacked traits, as well as the genes and events that provide these traits, are well known in the art. For example, detailed information about mutagenized or integrated genes and the respective events is available on 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 in patent applications such as EP3028573 and WO2017 / 011288.

[0412] The use of compounds of formula (I) according to the present invention or formulations or combinations containing them in crops can result in specific effects in crops containing certain genes or events. These effects can involve changes in growth behavior or changes in resistance to biotic or abiotic stress factors. Such effects can include, inter alia, yield promotion, promotion of resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasmal, viral or viroid pathogens, as well as early vigor, early or delayed ripening, cold or heat tolerance, and changes in the spectrum or content of amino acids or fatty acids.

[0413] Also included are plants that contain altered or new amounts of ingredients through the use of recombinant DNA technology, particularly to improve feedstock production, such as potatoes with increased amylopectin production (e.g., Amflora® potatoes, BASF SE, Germany).

[0414] Furthermore, it has been found that the compounds of formula (I) according to the invention or formulations and / or combinations comprising them are also suitable for defoliating and / or desiccating plant parts of crops, such as cotton, potato, rapeseed, sunflower, soybean or broad bean, in particular cotton. In this regard, formulations and / or combinations for desiccating and / or deficient in crops, processes for preparing these formulations and / or combinations, and methods for desiccating and / or deficient in plants using the compounds of formula (I) have been found.

[0415] As desiccants, the compounds of formula (I) are particularly suitable for drying the above-ground parts of crop plants such as potato, rapeseed, sunflower and soybean, but also the above-ground parts of cereals, which allows for the complete mechanical harvesting of these important crop plants.

[0416] Also of economic interest is the simplification of harvesting, which is made possible by concentrating dehiscence or reduction of plant attachment within a specific period in citrus fruits, olives, and other species, as well as various pernicious fruits, drupes, and nuts. The same mechanism, i.e., promoting the development of abscission tissue between the fruit or leaf and shoot parts of the plant, is also essential for controlling defoliation of useful plants, especially cotton.

[0417] Furthermore, shortening the time interval between maturation of individual cotton plants leads to improved fiber quality after harvest. [Example]

[0418] A. Chemical Examples Chemical bonds drawn as bars in chemical formulas (see, for example, CpdsI40, I60 below) indicate the relative stereochemistry on the ring system.

[0419] [Example 1] Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter A)

[0420] [ka]

[0421] Triethylamine (24.24 g, 240 mmol) was added dropwise to a solution of O1-benzyl O3-tert-butylpropanedioate (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 by silica gel chromatography (petroleum ether:ethyl acetate = 5:1) to give O1-benzyl O3-tert-butyl-2-diazopropanedioate (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).

[0422] [ka]

[0423] Dirhodium tetraacetate ([Rh(OAc)]) (143 mg) was added to a solution of O1-benzyl O3-tert-butyl-2-diazopropanedioate (2) (20 g, 72.46 mmol), methanol (14 mL) in toluene (300 mL) at 15 °C. The mixture was stirred for 16 hours at 60 °C. The mixture was filtered, and the filtrate was concentrated and purified by silica gel chromatography eluting with (petroleum ether:tert-butyl methyl ether=5:1) to give O1-benzyl O3-tert-butyl 2-methoxypropanedioate (3) (19 g, 93% yield) as a yellow oil. 1H NMR: (400MHz, 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).

[0424] [ka]

[0425] To a solution of O1-benzyl O3-tert-butyl 2-methoxypropanedioate (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 hours. The mixture was added to water and extracted with dichloromethane. The organic layer was washed with water and brine, dried, and 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).

[0426] [ka]

[0427] 1-Propanephosphonic anhydride solution (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: tert-butyl methyl 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. 1 H NMR: (400 MHz, CDCl3)δ 8.33 (br s, 1H), 7.53 (d, J=1.8 Hz, 2H), 7.42 - 7.34 (m, 5H), 7.14 (t, J=1.8 Hz, 1H), 5.29 (s, 2H), 4.47 (s, 1H), 3.54 (s, 3H).

[0428] [ka]

[0429] Palladium on carbon (Pd / C) (1 g, 10%) was added to a solution of benzyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoate (6) (5.5 g, 14.98 mmol) in tetrahydrofuran (100 mL). The mixture was stirred under hydrogen gas H (15 psi) at 10 °C for 2 h. The mixture was filtered through a Celite pad, and the filtrate was concentrated to give 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoic 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, 2H), 7.18 (t, J=1.8 Hz, 1H), 4.48 (s, 1H), 3.53 (s, 3H).

[0430] [Example 2] Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter B) Synthesis was carried out similarly to Walker, Daniel P. et al., Synthesis, (7), 1113-1119, 2011.

[0431] [ka]

[0432] 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 (BocNH) (4.1 g, 35.12 mmol), potassium carbonate (10.1 g, 73.14 mmol), CuI (1.67 g, 8.78 mmol), and (CHNHCH) (1.54 g, 17.56 mmol) at 15 °C. The mixture was then stirred at 130 °C under N for 16 h. The mixture was diluted with water (150 mL), filtered, extracted with ethyl acetate (100 mL), and 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.

[0433] [ka]

[0434] To a solution of dried 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. The mixture was then stirred under hydrogen gas (H) (50 psi) at 30 °C for 16 h. 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.

[0435] [ka]

[0436] 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 h. The mixture was concentrated to give methyl cis-4-aminotetrahydrofuran-2-carboxylate Inter B (3 g, crude) as a white solid (HCl salt). H NMR: (400 MHz, DO) 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).

[0437] [Example 3] Synthesis of methylamide cis-N-(3,5-dichlorophenyl)-2-methoxy-N'-[-5-(methylcarbamoyl)-tetrahydrofuran-3-yl]propanediamide (Cpd.I.60)

[0438] [ka]

[0439] To a mixture of Inter A (718 mg, 2.09 mmol) in acetonitrile (15 mL) was added Inter B (467 mg, 2.59 mmol), a solution of 1-propanephosphonic anhydride in ethyl acetate (T3P) (2.47 g, 3.885 mmol), and diisopropylethylamine (1.85 mL, 17.36 mmol) at 25 °C and stirred at 75 °C under N for 2 h. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated, and purified by prep-HPLC (acetonitrile / water containing trifluoroacetic acid) to give the desired methyl cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoyl]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, 1 H) 7.49 - 7.60 (m, 3 H) 7.13 (d, J=1.76 Hz, 1 H), 4.52 - 4.73 (m, 2 H), 4.26 (d, J=3.51 Hz, 1 H), 3.94 - 4.08 (m, 2 H) 3.80 (d, J=17.82 Hz, 3 H), 3.67 (d, J=3.01 Hz, 3 H), 2.50 - 2.61 (m, 1 H), 2.09 (dt, J=7.09, 3.73 Hz, 1 H).

[0440] [ka]

[0441] To a mixture of methyl cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]tetrahydrofuran-2-carboxylate (2.7 g, 6.9 mmol) in tetrahydrofuran (32.4 mL) was added LiOH (1.16 g, 27.7 mmol) in water (10.8 mL) at 25° C. and stirred for 2 hours at 25° C. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated, and purified by prep-HPLC (0.1% trifluoroacetic acid, acetonitrile-water) to give cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]tetrahydrofuran-2-carboxylate (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, 1 H), 8.30 (dd, J=16.22, 7.02 Hz, 1 H), 7.78 (t, J=1.75 Hz, 2 H), 7.32 (t,J=1.75 Hz, 1 H), 4.27 - 4.41 (m, 3 H) 3.90 (ddd, J=8.55, 6.36, 1.75 Hz, 1 H), 3.64 (dt, J=8.66,5.54 Hz, 1 H), 3.37 (s, 3 H), 1.93 (dtd, J=12.77, 6.22, 6.22, 2.85 Hz, 1 H).

[0442] [Example 4] Synthesis of Cpd.I.144

[0443] [ka]

[0444] To a solution of dimethyl methoxymalonate (CAS 5018-30-4) (1) (7.6 g, 47 mmol) in dimethylformamide (50 mL) was added sodium hydride (60%, 2.2 g) at 50 °C under argon. The resulting mixture was stirred at 50 °C for an additional 30 minutes until no further hydrogen gas evolution occurred. After cooling to room temperature, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, CAS 140681-55-6) (25 g) was added. The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3 × 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude product dimethyl 2-fluoro-2-methoxy-propanedioate (2) (7.9 g, 93% yield). 1H NMR: (400 MHz, CDCl3) δ 3.89 (s, 6H), 3.58 (s, 3H).

[0445] [ka]

[0446] To dimethyl 2-fluoro-2-methoxypropanedioate (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 tert-butyl methyl ether (2 × 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 × 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give the crude product 2-fluoro-2,3-dimethoxy-3-oxopropanoic acid (3) (5.3 g, 73% yield). 1H NMR: (400 MHz, CDCl3) δ 3.92 (s, 3H), 3.61 (s, 3H).

[0447] [ka]

[0448] Amide bond formation was carried out as described above (Example 1, compound 6). 56% yield for methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (4). 1H NMR: (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.57 (s, 2H), 7.18 (s, 1H), 3.92 (s, 3H), 3.63 (s, 3H).

[0449] [ka]

[0450] To methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxopropanoate (4) (3.8 g, 12 mmol) in 1,2-dichloroethane (100 mL) was added trimethyltin hydroxide (MeSnOH) (4.4 g, 25 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours, and then the reaction mixture was extracted with saturated sodium bicarbonate solution in water (3 × 100 mL). The combined organic phase was adjusted to pH 1 using concentrated hydrogen chloride solution in water. The resulting mixture was extracted with ethyl acetate (3 × 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-oxopropanoate (5) (1.2 g, 33% yield). LC-MS (M+H) + :295.8.

[0451] [ka]

[0452] To a solution of the carboxylic acid (0.3 g) in dimethylformamide (DMF, 10 mL) was added amine 6 (CAS 229613-83-6). To the resulting solution, HATU (0.42 g) and then diisopropylethylamine (0.53 mL) were added. 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 × 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 methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxopropanoyl]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).

[0453] [Example 5] Synthesis of methyl (1S,4R)-4-(methylamino)cyclopent-2-ene-1-carboxylate (Inter C)

[0454] [ka]

[0455] To a solution of (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (CAS 79200-56-9) (20.0 g, 183 mmol) in tetrahydrofuran (50 mL) was added sodium hydride (8.8 g, 0.22 mol) at 0 °C. 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 × 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]hept-5-en-3-one (5.6 g, 25%) as a colorless oil.

[0456] [ka]

[0457] To a solution of (1R,4S)-2-methyl-2-azabicyclo[2.2.1]hept-5-en-3-one (3.0 g, 24 mmol) in methanol (30 mL) was added thionyl chloride (3.5 mL, 49 mmol) at 0° C. After stirring for 3 h at room temperature, 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).

[0458] [Example 6] Synthesis of Cpd.I155

[0459] [ka]

[0460] 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 overnight at room temperature. To the reaction mixture was added water (30 mL) and saturated aqueous bicarbonate solution (30 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic phase was 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 methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]-methyl-amino]cyclopent-2-ene-1-carboxylate (700 mg, 47%, 1.155) 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).

[0461] [Example 7] Synthesis of Cpd.I123

[0462] [ka]

[0463] To a solution of carboxylic acid (120 g) in dimethylformamide (DMF, 500 mL) was added methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate 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 overnight at room temperature. To the reaction mixture was added water (50 mL) and saturated aqueous bicarbonate solution (50 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phase was 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 methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (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).

[0464] [Example 8] Synthesis of Cpd.I.136

[0465] [ka]

[0466] To methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd.I.123) (6.0 g, 15 mmol) in 1,2-dichloroethane (100 mL) was added trimethyltin hydroxide (MeSnOH) (5.4 g, 30 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours, and then the reaction mixture was extracted with saturated sodium bicarbonate solution in water (3 × 100 mL). The combined organic phase was adjusted to pH 1 using concentrated hydrogen chloride solution in water. The resulting mixture was extracted with ethyl acetate (3 × 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-propanoyl]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).

[0467] [Example 9] Synthesis of Cpd.I.142

[0468] [ka]

[0469] 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 overnight at room temperature. 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 × 20 mL). The combined organic phase was 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 2-chloroethyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (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).

[0470] [Example 10] Synthesis of Cpd.I.175

[0471] [ka]

[0472] 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 hour, sodium benzilate (CAS20194-18-7) (60 mg, 0.45 mmol) was added to the mixture, and stirring was continued for 3 hours. The reaction was quenched with water (5 mL), and the aqueous layer was separated and extracted with ethyl acetate (3 × 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 a solvent to give benzyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (24 mg, 10%, 1.175) as a mixture of diastereoisomers (1:1). LC-MS (M+H) + :477.1.

[0473] [Example 11] Synthesis of Cpd.I.201

[0474] [ka]

[0475] 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 overnight at room temperature. 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 × 10 mL). The combined organic phase was 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'-[(1R,4S)-4-(prop-2-ynylcarbamoyl)cyclopent-2-en-1-yl]propanediamide (47 mg, 14%, 1.201) 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).

[0476] [Example 12] Synthesis of Cpd.I.26

[0477] [ka]

[0478] To a solution of carboxylic acid (Inter A) (10 g, 36 mmol) in dimethylformamide (DMF, 100 mL) was added methyl 4-aminobutyrate hydrochloride (CAS13031-60-2) (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 overnight at room temperature. To the reaction mixture was added water (50 mL) and saturated aqueous bicarbonate solution (50 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phase was 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 methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoyl]amino]butanoate (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).

[0479] [Example 13] Synthesis of Cpd.I.116

[0480] [ka]

[0481] To a solution of methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoyl]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 hydrochloride solution (1 M, 10 mL) and extracted with ethyl acetate (3 × 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-oxopropanoyl]amino]butanoic acid (550 mg, 82%) as a colorless oil. 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).

[0482] [Example 14] Synthesis of Cpd.I.202-A

[0483] [ka]

[0484] To a solution of the 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'-dicyclohexylmethanediimine (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 a solvent to give N-(3,5-dichlorophenyl)-N'-[4-(methanesulfonamido)-4-oxo-butyl]-2-methoxy-propanediamide (25 mg, 10%, Cpd. I.202-A). LC-MS (M+H) + :439.9.

[0485] [Example 15] Synthesis of Cpd.I.203

[0486] [ka]

[0487] To a solution of the 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). To the resulting solution was added HATU (314 mg, 0.826 mol), followed by triethylamine (0.23 mL, 1.62 mmol). The resulting reaction mixture was stirred overnight at room temperature. To the reaction mixture were added water (10 mL) and saturated aqueous bicarbonate solution (10 mL). The resulting mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic phase was 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]propanediamide (180 mg, 81%, Cpd. I.203). 1H NMR (500 MHz, chloroform-d) δ 9.12 (s, 1H), 7.53 (d, J = 1.8 Hz, 2H), 7.21 (s, 1H), 7.10 (t, J = 1.8 Hz, 1H), 4.26 (s, 1H), 3.66 (s, 3H), 3.65 (s, 3H), 3.37 (qd, J = 6.6, 3.9 Hz, 2H), 3.17 (s, 3H), 2.50 (m, 2H), 1.90 (m, 2H).

[0488] High-performance liquid chromatography: HPLC-column Kinetex XB C18 1.7μ (50×2.1 mm); eluent: acetonitrile / water+0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60° C., flow gradient from 0.8 ml / min to 1.0 ml / min in 1.5 min).

[0489] Similar to the example described above, R 1 and R 9 The following compounds of formula (I) where is hydrogen were prepared starting from commercially available diesters and using commercially available amines:

[0490] [ka]

[0491] [Table 2] TIFF0007757297000148.tif245150TIFF0007757297000149.tif246156TIFF000 7757297000150.tif246156TIFF0007757297000151.tif248168TIFF00077572970 00152.tif248168TIFF0007757297000153.tif245159TIFF0007757297000154.t if245159TIFF0007757297000155.tif246169TIFF0007757297000156.tif248153 TIFF0007757297000157.tif248166TIFF0007757297000158.tif247169TIFF000 7757297000159.tif248163TIFF0007757297000160.tif247170TIFF00077572970 00161.tif247164TIFF0007757297000162.tif247164TIFF0007757297000163.t if246160TIFF0007757297000164.tif245162TIFF0007757297000165.tif245144

[0492] As in the above example, R 2 , R 6 , R 8 and R 9 The following compounds of formula (I) where is hydrogen were prepared starting from commercially available diesters and using commercially available amines:

[0493] [ka]

[0494] [Table 3] TIFF0007757297000168.tif38166

[0495] As in the above example, R 6 and R 8 The following compounds of formula (I) where is hydrogen were prepared starting from commercially available diesters and using commercially available amines:

[0496] [ka]

[0497] [Table 4]

[0498] As in the above example, R 1 , R 6 and R 9 The following compounds of formula (I) where is hydrogen were prepared starting from commercially available diesters and using commercially available amines:

[0499] [ka]

[0500] [Table 5] TIFF0007757297000173.tif252169TIFF0007757297000174.tif252155TIFF0007757297000175.tif252165TIFF00077572970 00176.tif252170TIFF0007757297000177.tif252169TIFF0007757297000178.tif250162TIFF0007757297000179.tif252148

[0501] B. Example of use The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0502] The culture containers used were plastic flowerpots filled with loam sand containing approximately 3.0% humus as the culture medium. Seeds of the test plants were sown separately for each species.

[0503] For pre-emergence treatment, the active ingredient suspended or emulsified in water was applied directly after sowing using a fine-dispensing nozzle. The containers were gently irrigated to promote germination and growth, and then covered with a transparent plastic hood until the test plants were established. This cover provided uniform germination of the test plants, unless this was impaired by the active ingredient.

[0504] For post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm depending on their habitat and only then treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same container, or they were first grown separately as seedlings and transplanted into the test containers a few days before treatment.

[0505] Test plants were kept at 10-25°C or 20-35°C depending on the species, respectively.

[0506] The test period lasted from 2 to 4 weeks, during which time the test plants were cared for and evaluated for their response to the individual treatments.

[0507] The ratings were made using a scale of 0 to 100, with 100 indicating no emergence or complete destruction of at least the aerial parts of the test plants, and 0 indicating no damage or normal growth. Excellent herbicidal activity was indicated by a value of 70 to 90, and very excellent herbicidal activity by a value of 90 to 100.

[0508] The test plants used in the greenhouse experiments were the following species:

[0509] [Table 6]

[0510] It was applied by the pre-emergence method at a rate of 0.125 kg / ha: Compounds I.159, I.185 and I.191 showed very good herbicidal activity against AMARE. Compound I.159 showed very good herbicidal activity against ALOMY. Compound I.159 showed very good herbicidal activity against SETFA. Compounds I.169 and I.185 showed very good herbicidal activity against APESV. Compounds I.169 and I.191 showed good herbicidal activity against ECHCG. Compound I.185 showed very good herbicidal activity against ABUTH.

[0511] It was applied by the pre-emergence method at a rate of 0.250 kg / ha: Compounds I.161, I.162, I.164, I.167, I.168, I.172, I.186, I.192, I.195, and I.210 showed very good herbicidal activity against APESV. Compounds I.155, I.156, I.157, and I.173 showed good herbicidal activity against APESV. Compounds I.163, I.192, I.198, and I.210 showed very good herbicidal activity against ABUTH. Compounds I.157, I.162, I.165, I.166, I.174, I.176, I.179, I.180, I.181, I.184, and I.186 showed good herbicidal activity against ABUTH. 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, I.198, and I.210 showed very good herbicidal activity against AMARE. Compounds I.164, I.188 and I.190 showed good herbicidal activity against AMARE. Compounds I.161, I.163, I.164, I.166, I.175, I.176, I.177, I.184, I.195, and I.211 showed very good herbicidal activity against SETFA. Compound I.173 showed good herbicidal activity against SETFA. Compounds I.165, I.167, I.175, I.177, I.181, I.183, I.188, I.189, I.190, I.195, and I.198 showed very good herbicidal activity against ECHCG. Compound I.168 showed good herbicidal activity against ECHCG. Compounds I.174, I.177, I.178, I.180, I.183, I.188, I.189 and I.211 showed very good herbicidal activity against ALOMY.

[0512] It was applied by the pre-emergence method at a rate of 0.500 kg / ha: Compounds I.13 and I.36 showed very good herbicidal activity against ALOMY. Compounds I.13 and I.64 showed very good herbicidal activity against AMARE. 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, and I.207 showed very good herbicidal activity against APESV. 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, and I.208 showed good herbicidal activity against APESV. Compounds I.9, I.28, I.33, I.36, I.39, I.51, I.55, I.123, I.124, and I.145 showed very good herbicidal activity against ECHCG. Compounds I.34, I.45, I.108, I.205, and I.207 showed good herbicidal activity against ECHCG. Compounds I.57, I.104, I.158 and I.208 showed very good herbicidal activity against SETFA. Compounds I.58, I.109, and I.145 showed good herbicidal activity against SETFA.

[0513] It was applied by the pre-emergence method at a rate of 1.000 kg / ha: Compound I.100 showed very good herbicidal activity against AMARE. Compounds I.40, I.59, I.60, I.84, I.100 and I.101 showed very good herbicidal activity against APESV. Compounds I.63, I.68, and I.95 showed good herbicidal activity against APESV. Compound I.40 showed very good herbicidal activity against ECHCG. Compound I.60 showed good herbicidal activity against ECHCG. Compounds I.59 and I.101 showed very good herbicidal activity against SETFA.

[0514] It was applied by post-emergence method at a rate of 0.125 kg / ha: Compounds I.159, I.169, I.185, I.191 and I.192 showed very good herbicidal activity against ALOMY. Compounds I.17, I.170 and I.171 showed good herbicidal activity against ALOMY. Compounds I.159 and I.185 showed very good herbicidal activity against AMARE. Compound I.192 showed good herbicidal activity against AMARE. Compounds I.159 and I.185 showed very good herbicidal activity against ABUTH. Compounds I.169, I.170, I.171, I.191 and I.192 showed good herbicidal activity against ABUTH. Compounds I.17, I.170, and I.191 showed good herbicidal activity against AVEFA.

[0515] It was applied by post-emergence method at a rate of 0.250 kg / ha: 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 and I.211 showed very good herbicidal activity against ALOMY. Compounds I.155, I.156 and I.197 showed good herbicidal activity against ALOMY. 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 showed very good herbicidal activity against ABUTH. Compounds I.157, I.179, I.188, I.190, I.192, I.197, and I.210 showed good herbicidal activity against ABUTH. 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, and I.198 showed very good herbicidal activity against AMARE. 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, and I.192 showed good herbicidal activity against AMARE. Compounds I.163, I.172, I.173, I.178 and I.211 showed very good herbicidal activity against AVEFA. Compounds I.166, I.167, I.176, I.179, I.180, I.184, and I.198 showed very good herbicidal activity against ECHCG. Compound I.195 showed good herbicidal activity against ECHCG. Compounds I.183, I.195, I.210 and I.211 showed very good herbicidal activity against SETVI. Compound I.197 showed good herbicidal activity against SETVI.

[0516] It was applied by post-emergence method at a rate of 0.500 kg / ha: Compounds I.47, I.51, I.104, I.108, I.109, I.158, and I.205 showed very good herbicidal activity against ABUTH. Compounds I.52, I.55, I.145, and I.204 showed good herbicidal activity against ABUTH. 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, and I.205 showed very good herbicidal activity against ALOMY. 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, and I.208 showed good herbicidal activity against ALOMY. Compounds I.5, I.13, I.57, I.58, I.108, I.109, I.122, I.123 and I.124 showed very good herbicidal activity against AMARE. 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, and I.205 showed good herbicidal activity against AMARE. Compound I.42 showed good herbicidal activity against APESV. Compounds I.2, I.3, I.4, I.9, I.33, I.38, I.39, I.64, I.110, I.145, and I.208 showed very good herbicidal activity against AVEFA. 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, and I.207 showed good herbicidal activity against AVEFA. Compounds I.9, I.28, I.62, and I.158 showed very good herbicidal activity against ECHCG. Compounds I.3 and I.4 showed very good herbicidal activity against LOLMU. Compound I.2 showed very good herbicidal activity against POLCO. 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, and I.208 showed very good herbicidal activity against SETVI. Compounds I.23, I.26, I.35, I.38, I.46, I.118, I.119, I.120, and I.121 showed good herbicidal activity against SETVI.

[0517] It was applied by post-emergence method at a rate of 1.000 kg / ha: Compounds I.100 and I.101 showed very good herbicidal activity against ABUTH. Compound I.96 showed good herbicidal activity against ABUTH. Compounds I.1, I.40 and I.100 showed very good herbicidal activity against ALOMY. Compounds I.66, I.68, I.84, I.94 and I.95 showed good herbicidal activity against ALOMY. Compounds I.59, I.60 and I.63 showed very good herbicidal activity against AMARE. Compounds I.40 and I.94 showed good herbicidal activity against AMARE. Compounds I.66, I.68, I.94, I.95, and I.96 showed good herbicidal activity against AVEFA. Compound I.40 showed good herbicidal activity against ECHCG. Compound I.1 showed very good herbicidal activity against POLCO. Compounds I.59 and I.101 showed very good herbicidal activity against SETVI. Compounds I.1, I.60, and I.84 showed good herbicidal activity against SETVI. Aspects of the present disclosure include the following. [1] Formula (I) [ka] wherein the substituents have the following meanings: R 1 is hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 2 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 3 is hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3-C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 4 )-halocycloalkyl, (C 1 -C 3 )-alkoxy (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio; R 5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2-C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl; R 6 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 7 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; R 8 is hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 3 )-hydroxyalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkoxy-(C 1 -C 3 )-alkyl, (C 3 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 3 )-cyanoalkoxy, (C 1 -C 3 )-alkoxy-(C 1-C 3 )-alkoxy, (C 3 -C 5 )-cycloalkyl-(C 1 -C 3 )-alkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 1 -C 3 )-alkylthio; R 9 is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy; X is a bond (X 0 ), or (X 1 )、(X 2 )、(X 3 )、(X 4 )、(X 5 ) and (X 6 ):

change

[10] The substituents have the following meanings: X is a bond; Y is Z; Z is a 4- or 5-membered saturated or partially unsaturated ring formed from r carbon atoms and n oxygen atoms, each of which is CO 2 R e ,CONR b R h ,CONR e SO 2 R a 、R b 、R c 、R e and R f is substituted with m groups from the group consisting of A compound according to any one of aspects 1 to 8.

[11] The substituents have the following meanings: R 1 is hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 2 is hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 3 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 5 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl; R 4 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 4 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl; R 5 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 5 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl; R 6 is hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 7 is methyl; R8 is hydrogen or fluorine; R 9 is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy; X is a bond; Y is Z or (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl or (C 2 -C 8 )-alkynyl, each of which is fluorine, CO 2 R e and CONR e SO 2 R a substituted with m groups from the group consisting of: Z is composed of r carbon atoms, n oxygen atoms, and CO 2 R e ,CONR b R h ,CONR e SO 2 R a 、R b 、R c 、R e and R f a 4-5 membered saturated or partially unsaturated ring substituted with m groups selected from the group consisting of: R a is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R b is hydrogen or (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy; R c are fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a , or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy or (C 3 -C 6 )-alkynyloxy, each of which is selected from fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is selected from fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy; R f is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy; R h is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is selected from fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy; m is 0, 1, 2, 3, 4 or 5; n is 0, 1 or 2; r is 1, 2, 3, 4 or 5 2. The compound of embodiment 1.

[12] A composition comprising at least one compound according to any one of aspects 1 to 11 and at least one adjuvant customary for formulating crop protection compounds.

[13] 13. The composition of embodiment 12, comprising an additional herbicide.

[14] 14. Use of a compound according to any one of aspects 1 to 11 or a composition according to aspect 12 or 13 for controlling unwanted vegetation.

[15] 16. A method for controlling unwanted vegetation, comprising applying a herbicidally effective amount of at least one compound of any one of embodiments 1 to 11, or a composition of embodiment 12 or 13, to plants, their seeds, and / or their habitat.

Claims

1. Formula (I) 【Chemical 1】 wherein the substituents have the following meanings: R 1 is hydrogen, (C 1 -C 3 )-alkyl; R 2 is hydrogen, halogen, (C 1 -C 3 )-alkoxy; R 3 is hydrogen, halogen, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy; R 4 is hydrogen, halogen, (C 1 -C 3 )-alkyl; R 5 is hydrogen, halogen, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy; R 6 is hydrogen, halogen; R 7 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, each of which is substituted with m groups from the group consisting of fluorine; R 8 is hydrogen, halogen, (C 1 -C 6 )-alkyl; R 9 is hydrogen, (C 1 -C 6 )-alkyl; X is a bond (X 0 ), or (X 1 ), (X 2 ), (X 3 ) and (X 6 ): 【Chemistry 2】 (wherein the left arrow represents the bond to the adjacent nitrogen and the right arrow represents the bond to the adjacent group Y). is a divalent unit from the group consisting of: R 10 ~R 15 are independently hydrogen, CO 2 R e , or (C 1 -C 6 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 6 )-alkenyl (each substituted by m groups from the group consisting of fluorine), or (C 1 -C 6 )-alkoxy; Y is hydrogen, Z, or (C 1 -C 12 )-alkyl, (C 2 -C 12 )-alkenyl, each of which is S(O) n R a and CO 2 R e substituted with m groups from the group consisting of: Z is CO 2 R e ,CONR b R h , and R b a cyclobutane, cyclopentane, cyclopentene, tetrahydrofuran, or tetrazole ring substituted with m groups from the group consisting of: R a is (C 1 -C 6 )-alkyl; R b is hydrogen or R a and; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl, phenyl-(C 1 -C 3 )-alkyl, furanyl-(C 1 -C 3 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is fluorine, chlorine, CO 2 R a and (C 1 -C 2 )-alkoxy; R h is (C 1 -C 6 )-alkyl; m is 0, 1, 2 or 3; n is 0 or 1. (When the compound of formula (I) has a carboxyl group, an agriculturally acceptable salt thereof, mono- or di-C 1 -C 6 -Alkylamide or arylamide, allyl ester, propargyl ester, C 1 -C 10 -alkyl ester, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl ester, (tetrahydrofuran-2-yl)methyl ester, or C 1 -C 10 -including alkyl thioesters).

2. The substituents have the following meanings: R 1 is hydrogen; R 9 is hydrogen 2. The compound of claim 1.

3. The substituents have the following meanings: R 2 is hydrogen, halogen 3. The compound of claim 1 or 2.

4. The substituents have the following meanings: R 3 is hydrogen, halogen, cyano, (C 1 -C 3 )-alkyl; R 5 is hydrogen, halogen, cyano, (C 1 -C 3 )-alkyl 4. A compound according to any one of claims 1 to 3.

5. The substituents have the following meanings: R 4 is hydrogen, halogen 5. A compound according to any one of claims 1 to 4.

6. The substituents have the following meanings: R 7 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, each of which is substituted by m groups from the group consisting of fluorine 6. A compound according to any one of claims 1 to 5.

7. The substituents have the following meanings: R 8 is hydrogen, halogen 7. A compound according to any one of claims 1 to 6.

8. The substituents have the following meanings: X is a bond 8. A compound according to any one of claims 1 to 7.

9. The substituents have the following meanings: X is a bond; Y is (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, each of which is S(O) n R a and CO 2 R e is substituted with m groups from the group consisting of 9. A compound according to any one of claims 1 to 8.

10. The substituents have the following meanings: X is a bond; Y is Z; Z is a cyclobutane, cyclopentane, cyclopentene, or tetrahydrofuran ring, each of which is CO 2 R e is substituted with m groups from the group consisting of 9. A compound according to any one of claims 1 to 8.

11. The substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen; R 3 is a halogen, cyano, (C 1 -C 3 )-alkyl; R 4 is hydrogen or fluorine; R 5 is a halogen, cyano, (C 1 -C 3 )-alkyl; R 6 is hydrogen; R 7 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl; R 8 is hydrogen, halogen; R 9 is hydrogen; X is a bond; Y is Z; Z is CO 2 R e a cyclobutane, cyclopentane, cyclopentene, or tetrahydrofuran ring substituted with m groups from the group consisting of: R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl or (C 3 -C 4 )-alkynyl, each of which is fluorine, chlorine, and (C 1 -C 2 )-alkoxy; m is 0, 1, or 2; 2. The compound of claim 1.

12. 12. A herbicidal composition comprising at least one compound according to any one of claims 1 to 11 and at least one adjuvant customary for formulating crop protection compounds.

13. 13. The composition of claim 12, further comprising an herbicide.

14. 14. Use of a compound according to any one of claims 1 to 11 or a composition according to claim 12 or 13 for controlling unwanted vegetation.

15. 14. A method for controlling unwanted vegetation, comprising applying a herbicidally effective amount of at least one compound according to any one of claims 1 to 11 or a composition according to claim 12 or 13 to plants, their seeds and / or their habitat.

16. The substituents have the following meanings: R 1 is hydrogen; R2 is hydrogen; R 3 is chlorine or fluorine; R4 is hydrogen; R 5 is chlorine or fluorine; R 6 is hydrogen; R 7 is methyl; R 8 is hydrogen; R 9 is hydrogen; X is a bond; Y is Z; Z is a cyclobutane, cyclopentane, cyclopentene, or tetrahydrofuran ring substituted with m groups from the group consisting of CO2Re; R e is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl or (C 3 -C 4 )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine and (C 1 -C 2 )-alkoxy; m is 0, 1 or 2 2. The compound of claim 1.

17. The following: 【Table 1】 17. The compound of claim 16, selected from:

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