Bisoxazolines and their use as herbicides

Abstract

The present invention relates to a compound of formula (I) and its use as a herbicide. 1 ‑R 7 represents a radical such as hydrogen, halogen or an organic radical such as alkyl, alkenyl, alkynyl or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic radical. The invention also relates to compositions comprising such compounds and their use for controlling unwanted vegetation.

Description

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

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

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

[0004] The compounds of the prior art often have insufficient herbicidal activity, especially at low application rates, and / or unsatisfactory selectivity, resulting in low compatibility with crop plants.

[0005] It was therefore an object of the present invention to provide compounds which have strong herbicidal activity, particularly even at low application rates, sufficiently low toxicity to humans and animals and / or high compatibility with crop plants. The bisoxazoline compounds should also exhibit a broad spectrum of activity against a large number of different undesirable plants.

[0006] These and other objects are achieved by the compounds of formula (I) as defined below, including the agriculturally acceptable salts, amides, esters or thioesters thereof.

[0007] Therefore, the present invention provides compounds of formula (I):

[0008]

[0009] The substituents have the following meanings:

[0010] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy;

[0011] R 2 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0012] R 3Hydrogen, halogen, nitro, hydroxy, 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;

[0013] R 4 Hydrogen, halogen, hydroxy, 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;

[0014] R 5 Hydrogen, halogen, nitro, hydroxy, 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;

[0015] R 6 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0016] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0017] X key (X 0 ) or a divalent unit selected from the following: (X 1 )、(X 2 )、(X 3 )、(X 4 )、(X 5 ) and (X 6 ):

[0018]

[0019] R 8 -R 13each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e ,CONR b R d NR b CO2R e , R a , or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano, or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0020] Y hydrogen, cyano, hydroxyl, Z,

[0021] or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R e NR b SO2NR b R e 、OCONR b R e 、OCSNR b R e 、POR f R fand C(R b )=NOR e ;

[0022] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h 、S(O) n R a 、SO2NR b R d 、SO2NR b COR e , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R e NR b SO2NR b R e 、OCONR b R e 、OCSNR b R e 、POR f R f and C(R b )=NOR e , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0023] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3 alkoxy;

[0024] R b Hydrogen, C1-C3 alkoxy or R a ;

[0025] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0026] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2R a ,CONR b R h , C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;

[0027] R e R d ;

[0028] R f C1-C3 alkyl or C1-C3 alkoxy;

[0029] R h 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 substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy;

[0030] m 0, 1, 2, 3, 4, or 5;

[0031] n 0, 1, or 2;

[0032] r 1, 2, 3, 4, 5, or 6;

[0033] Agriculturally acceptable salts, amides, esters or thioesters thereof are included, provided that the compound of formula (I) has a carboxyl group; 5-methyl-3-phenyl-1,4,2-dioxazole-5-carboxamide is excluded.

[0034] The present invention also provides formulations comprising at least one compound of the formula (I) and adjuvants conventionally used in formulating crop protection agents.

[0035] The invention also provides a combination comprising at least one compound of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C).

[0036] The invention also provides for the use of the compounds of the formula (I) as herbicides, ie for controlling undesirable vegetation.

[0037] The invention furthermore provides a method for controlling unwanted vegetation, wherein a herbicidally effective amount of at least one compound of the formula (I) is allowed to act on the plants, their seeds and / or their habitat.

[0038] If the compounds of the formula (I), the herbicidal compounds B and / or the safeners C described herein are capable of forming geometrical isomers, for example E / Z isomers, both the pure isomers and their mixtures can be used according to the invention.

[0039] If the compounds of the formula (I), the herbicidal compounds B and / or the safeners C described herein have one or more chiral centers and therefore exist as enantiomers or diastereomers, it is possible according to the invention to use both the pure enantiomers and diastereomers and also mixtures thereof.

[0040] If the compounds of formula (I), herbicidal compounds B and / or safeners C described herein have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Suitable are generally salts of those cations and acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

[0041] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium in which 1 to 4 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, diiso ... ammonium, trimethylammonium, triethylammonium, triisopropylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alcoholamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tri(2-hydroxyethyl)ammonium (triolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), in addition ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxide ions, preferably tri(C1-C4-alkyl)sulfoxide, and finally salts of polyamines, such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0042] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0043] The compounds of formula (I) having a carboxyl group, the herbicidal compounds B and / or the safeners C described herein may be in the form of an acid, in the form of an agriculturally acceptable salt as described above or in the form of an agriculturally acceptable derivative, for example as an amide, such as mono- and di-C1-C6-alkylamide or arylamide, as an ester, for example as an allyl ester, propargyl ester, C1-C6-alkylamide or C1-C6-alkylamide. 10 Alkyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as C1-C 10 Alkylthio esters are used. Preferred mono- and di-C1-C6 alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, benzamide and 2-chlorobenzamide. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C1-C4 alkoxy-C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl esters. Straight-chain or branched C1-C 10 An example of an alkylthio ester is ethylthio ester.

[0044] The terms of organic radicals used in the definitions of the variables, such as the expression "halogen", are collective terms representing the individual members of these groups of organic units.

[0045] Prefix C x -C y Indicates the possible number of carbon atoms in a particular case. All hydrocarbon chains may be straight or branched.

[0046] Halogen: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine;

[0047] Alkyl and the alkyl structure of composite groups such as alkoxy, alkylamino, alkylthio, alkoxycarbonyl: a saturated straight-chain or branched hydrocarbon group having 1 to 10 carbon atoms, such as C1-C 10Alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethyl Butyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl, 2-ethylhexyl and positional isomers thereof; nonyl, decyl and positional isomers thereof;

[0048] Haloalkyl: straight-chain or branched alkyl radicals having 1 to 10 carbon atoms (as described above), wherein some or all of the hydrogen atoms in these radicals are replaced by the above-mentioned halogen atoms. In one embodiment, the alkyl radicals are substituted at least once or completely by specific halogen atoms, preferably fluorine, chlorine or bromine. In another embodiment, the alkyl radicals are partially or completely halogenated by different halogen atoms; in the case of mixed halogen substitution, a combination of chlorine and fluorine is preferred. Particularly preferred is C1-C3 haloalkyl, more preferably C1-C2 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, 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-trifluoropropan-2-yl;

[0049] Alkenyl and also the alkenyl moiety in composite groups such as alkenyloxy: an unsaturated straight-chain or branched hydrocarbon radical having 2 to 10 carbon atoms and one double bond at any position. According to the invention, it may be preferred to use small alkenyl groups, such as C2-C4 alkenyl; on the other hand, it may also be preferred to use larger alkenyl groups, such as C5-C8 alkenyl. Examples of alkenyl 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 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;

[0050] Haloalkenyl: alkenyl as described above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 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-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;

[0051] Alkynyl and alkynyl structural parts in complex groups such as alkynyloxy: straight-chain or branched hydrocarbon groups having 2 to 10 carbon atoms and one or two triple bonds at any position, for example C2-C6 alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl 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;

[0052] Haloalkynyl: alkynyl as described above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

[0053] Cycloalkyl and also cycloalkyl moieties in composite groups: monocyclic or bicyclic saturated hydrocarbon radicals having 3 to 10, in particular 3 to 6 carbon ring members, for example C3-C6 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Examples of bicyclic radicals include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. In this context, optionally substituted C3-C8 cycloalkyl refers to cycloalkyl radicals having 3 to 8 carbon atoms, in which at least one hydrogen atom, such as 1, 2, 3, 4 or 5 hydrogen atoms, is substituted by a substituent which 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;

[0054] Halogenated heterocycloalkyl and the halocycloalkyl moiety in halocycloalkyloxy, halocycloalkylcarbonyl, etc.: a monocyclic saturated hydrocarbon group having 3 to 10 carbon ring members (as described above), in which some or all of the hydrogen atoms may be replaced by the above-mentioned halogen atoms, especially fluorine, chlorine and bromine;

[0055] Cycloalkoxy: a cycloalkyl group as described above attached via an oxygen group;

[0056] Alkoxy as well as alkoxy moieties in composite groups, such as alkoxyalkyl:alkyl as defined above attached via oxygen, preferably have 1 to 10, more preferably 2 to 6 carbon atoms. Examples are methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

[0057] Haloalkoxy: Alkoxy as defined above, wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms, in particular fluorine, chlorine or bromine, as above under haloalkyl. Examples are OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichloromonofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2 , 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5-fluoropentyloxy, 5-chloropentyloxy, 5-bromopentyloxy, 5-iodopentyloxy, undecafluoropentyloxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy or dodecafluorohexyloxy;

[0058] Alkylthio: an alkyl group as defined above attached via a sulfur atom, preferably having 1 to 6, more preferably 1 to 3 carbon atoms.

[0059] Alkylsulfinyl: an alkyl group as defined above attached via S(O), preferably having 1 to 6, more preferably 1 to 3 carbon atoms.

[0060] Alkylsulfonyl: an alkyl group as defined above attached via S(O)2, preferably having 1-6, more preferably 1-3 carbon atoms.

[0061] Hydroxyl: OH group attached via an O atom;

[0062] Cyano: CN group attached via a C atom;

[0063] Nitro: A NO2 group attached via a N atom.

[0064] The preferred embodiments according to the invention described below are to be understood as being preferred either independently of one another or in combination with one another.

[0065] According to a particular embodiment of the invention, preference is also given to those compounds of the formula (I) in which the variables, independently of one another or in combination with one another, have the following meanings:

[0066] Preferred compounds according to the present invention are compounds of formula (I), wherein R 1 Selected from 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.

[0067] More preferred compounds according to the present invention are compounds of formula (I), wherein R 1 Selected from hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl and C1-C3 alkoxy-C1-C3 alkyl.

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

[0069] In particular, R 1 For hydrogen.

[0070] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 2 Selected from hydrogen, halogen and C1-C3 alkyl.

[0071] Also preferred according to the invention are compounds of formula (I), wherein R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

[0072] In particular, R 2 For hydrogen.

[0073] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 3 is selected from hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy.

[0074] More preferred compounds according to the present invention are compounds of formula (I), wherein R 3 Selected from halogen, cyano and C1-C3 alkyl.

[0075] Also preferred according to the invention are compounds of formula (I), wherein R 3 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, methyl, trifluoromethyl and trifluoromethoxy.

[0076] In particular, R 3 is hydrogen or halogen, very particularly chlorine or fluorine.

[0077] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 4 is selected from hydrogen and halogen.

[0078] Also preferred according to the invention are compounds of formula (I), wherein R4 is selected from the group consisting of hydrogen, fluorine, chlorine and bromine.

[0079] In particular, R 4 is hydrogen or hydrogen, fluorine or chlorine, very particularly hydrogen.

[0080] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 5 is selected from hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy.

[0081] More preferred compounds according to the present invention are compounds of formula (I), wherein R 5 Selected from halogen, cyano and C1-C3 alkyl.

[0082] Also preferred according to the invention are compounds of formula (I), wherein R 5 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, methyl, trifluoromethyl and trifluoromethoxy.

[0083] In particular, R 5 is hydrogen or halogen, very particularly chlorine or fluorine.

[0084] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 3 and R 5 is selected from hydrogen, halogen, hydroxy, cyano and C1-C3 alkyl, and wherein R 3 and R 5 At least one of them is not hydrogen.

[0085] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 6 Selected from hydrogen, halogen and C1-C3 alkyl.

[0086] Also preferred according to the invention are compounds of formula (I), wherein R 6 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

[0087] In particular, R 6 For hydrogen.

[0088] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 7 is selected from C1-C3 alkyl, C3-C4 cycloalkyl, C2-C3 alkenyl and C1-C3 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine and C1-C2 alkoxy. In this context, m is preferably 0, 1, 2 or 3.

[0089] Also preferred according to the invention are compounds of formula (I), wherein R 7Selected from C1-C2 alkyl, cyclopropyl, C1-C2 haloalkyl, C2-C3 alkenyl and C1-C2 alkoxy.

[0090] In particular, R 7 are methyl, chloromethyl, trifluoromethyl, cyclopropyl, vinyl and methoxy, very particularly methyl.

[0091] In the compounds of formula (I), X is selected from a bond (X 0 ) or a divalent unit selected from the following: (X 1 )、(X 2 )、(X 3 )、(X 4 )、(X 5 ) and (X 6 ), where the molecule (X 1 )、(X 2 )、(X 3 )、(X 4 )、(X 5 ) and (X 6 ) are 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.

[0092]

[0093] In the preferred embodiment (Formula (IX 0 ) compound), X is a bond (X 0 ):

[0094]

[0095] In another preferred embodiment (Formula (IX 1 ) compound), X is (X 1 ), where the molecule (X 1 ) are 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:

[0096]

[0097] In another preferred embodiment (Formula (IX 2 ) compound), X is (X 2 ), where the molecule (X 2 ) are 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:

[0098]

[0099] In another preferred embodiment (Formula (IX 3 ) compound), X is (X3 ), where the molecule (X 3 ) are 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:

[0100]

[0101] In another preferred embodiment (Formula (IX 4 ) compound), X is (X 4 ), where the molecule (X 4 ) are 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:

[0102]

[0103] In another preferred embodiment (Formula (IX 5 ) compound), X is (X 5 ), where the molecule (X 5 ) are 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:

[0104]

[0105] In another preferred embodiment (Formula (IX 6 ) compound), X is (X 6 ), where the molecule (X 6 ) are 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:

[0106]

[0107] Further preferred compounds according to the present invention are compounds of formula (I), wherein X is selected from a bond (X 0 ) or a divalent unit selected from the following: CH2, CH2CH2, CHCH3, CH2CH2CH2, CH(CH2CH3), CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C(iPr)CH3, CH(CH2iPr)CH2, CH2CH=CH, C(CH3)2C≡C, CH(CF3)CH2, CH(CH3)CH2O, CH2CH2O, CH(cPr)CH2O, CH(CH2OCH3), CH(CH2CH2SCH3), CH(COOH), CH(COOCH3), CH(COOH)CH2, CH(COOCH3)CH2, CH2COH(CF3), CH(CONHCH3), CH(CONHCH3)CH2 and CH2CH2CONHCH2.

[0108] Further preferred compounds according to the present invention are compounds of formula (I), wherein R 8 -R 13 Each independently selected from 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 selected from the following groups: fluorine; or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, each substituted by m groups selected from the following groups: fluorine.

[0109] Also preferred according to the invention are compounds of formula (I), wherein R 8 -R 13 Each independently selected from 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 selected from the following: fluorine; or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, each substituted by m groups selected from the following: fluorine.

[0110] Also preferred according to the invention are compounds of formula (I), wherein R 8 -R 13 Each independently selected from hydrogen, fluorine, chlorine, CO2R e ,CONR b R d or C1-C6 alkyl, substituted by m groups selected from the group consisting of fluorine or C1-C6 alkoxy, substituted by m groups selected from the group consisting of fluorine or C1-C6 alkoxy.

[0111] In particular, R 8 -R 13 Each independently selected from halogen, C1-C6 alkyl, C1-C3 alkoxy and CO2R e .

[0112] Further preferred compounds according to the present invention are compounds of formula (I), wherein Y is selected from hydrogen, cyano, hydroxyl, Z, or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO2R eand CONR b R h .

[0113] Also preferred according to the present invention are compounds of formula (I), wherein Y is selected from hydrogen, cyano, hydroxy, Z, or C1-C 12 Alkyl and C3-C8 cycloalkyl, each substituted by m groups selected from the group consisting of fluorine, CO2R e and CONR b R h .

[0114] Also preferred according to the present invention are compounds of formula (I), wherein Y is selected from C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R 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 .

[0115] Also preferred according to the present invention are compounds of formula (I), wherein Y is selected from C1-C 12Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine and CO2R e .

[0116] In particular, Y is selected from Z, or C1-C 12 Alkyl and C3-C8 cycloalkyl, each substituted by m groups selected from the group consisting of fluorine, C1-C2 alkoxy, CO2R e and CONR b R h .

[0117] According to a preferred embodiment, Y is Z.

[0118] Preferred compounds according to the invention are compounds of formula (I), wherein Z is selected from a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms and n oxygen atoms, each substituted by m groups selected from: CO2R e ,CONR b R h 、S(O) n R a 、SO2NR b R d 、SO2NR b COR e , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R e NR b SO2NR b R e 、OCONR b R e 、OCSNR b R e 、POR f R f and C(R b )=NOR e , R b , R c , R e and R f, and wherein the carbon atom carries n oxo groups.

[0119] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms and n oxygen atoms, each substituted by m groups selected from: CO2R e ,CONR b R h , R b , R c , R e and R f , and wherein the carbon atom carries n oxo groups.

[0120] Further preferred compounds according to the invention are compounds of formula (I), wherein Z is selected from a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups.

[0121] Representative examples of the above 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0122]

[0123] Representative examples of the above 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

[0124]

[0125] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 4- or 5-membered saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, each substituted by m groups selected from: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f .

[0126] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 4- or 5-membered saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, each substituted by m groups selected from: CO2R e ,CONR b R h , R b , R c , R e and R f .

[0127] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f .

[0128] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , R e and R f .

[0129] Representative examples of 5-membered saturated or partially unsaturated rings, formed by 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the group consisting of: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, with arrows indicating bonds to any of the above substituents:

[0130]

[0131] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the following: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0132]

[0133] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 4 carbon atoms and 1 oxygen atom, each of which is substituted by m groups selected from the following: e ,CONR b R h , R b , R c , R e and R f , is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0134]

[0135] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 5 carbon atoms, each substituted by m groups selected from: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f .

[0136] Also preferred according to the invention are compounds of formula (I), wherein Z is selected from a 5-membered saturated or partially unsaturated ring, formed by 5 carbon atoms, each substituted by m groups selected from: CO2R e ,CONR b R h , R b , R c , R e and R f .

[0137] A 5-membered saturated or partially unsaturated ring, formed by 5 carbon atoms, each of which is substituted by m groups selected from the following: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, with arrows indicating bonds to any of the above substituents:

[0138]

[0139] Other representative examples of 5-membered saturated or partially unsaturated rings are formed by 5 carbon atoms, each of which is substituted by m groups selected from the following: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, with arrows indicating bonds to any of the above substituents:

[0140]

[0141] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 5 carbon atoms, each of which is substituted by m groups selected from the following: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0142]

[0143] A preferred example of a 5-membered saturated or partially unsaturated ring is formed by 5 carbon atoms, each of which is substituted by m groups selected from the following: e ,CONR b R h , R b , R c , R e and R f, is the following structure, the arrow indicates the bond to any of the above substituents, preferably to CO2R e Keys:

[0144]

[0145] In particular, Z is selected from cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each substituted by m groups selected from: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f .

[0146] Very particularly, Z is selected from cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each substituted by m groups selected from: CO2R e ,CONR b R h , R b , R c , R e and R f .

[0147] Preferred examples of Z.1-Z.5 are each substituted by m groups selected from the following groups: e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f , is the following structure, arrow (1) indicates the bonding position to X, arrows (2) and (3) indicate the bonds to any of the substituents, in particular to CO2R e ,CONR b R h , R b , R c , R e and R f Keys:

[0148]

[0149] Preferred compounds according to the invention are compounds of formula (I) in which the substituents have the following meanings:

[0150] R 1Hydrogen, 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;

[0151] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0152] R 3 Hydrogen, halogen, nitro, hydroxy, 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;

[0153] R 4 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0154] R 5 Hydrogen, halogen, nitro, hydroxy, 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;

[0155] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0156] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0157] X key (X 0 ) or a divalent unit selected from the following: (X 1 )、(X 2 )、(X3 )、(X 4 )、(X 5 ) and (X 6 ):

[0158]

[0159] R 8 -R 13 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e ,CONR b R d , R a , or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano, or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0160] Y hydrogen, cyano, hydroxyl, Z, or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R 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 ;

[0161] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0162] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0163] R b Hydrogen or R a ;

[0164] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0165] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0166] R e R d ;

[0167] R f C1-C3 alkyl or C1-C3 alkoxy;

[0168] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0169] m 0, 1, 2, 3, 4, or 5;

[0170] n 0, 1, or 2;

[0171] r 1, 2, 3, 4, 5, or 6;

[0172] Agriculturally acceptable salts, amides, esters or thioesters thereof are included, provided that the compound of formula (I) has a carboxyl group; 5-methyl-3-phenyl-1,4,2-dioxazole-5-carboxamide is excluded.

[0173] Preferred compounds according to the invention are compounds of formula (I) in which the substituents have the following meanings:

[0174] R 1 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;

[0175] R 2 hydrogen;

[0176] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0177] R 4 Hydrogen or fluorine, preferably hydrogen;

[0178] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0179] R 6 hydrogen;

[0180] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0181] X key;

[0182] YZ;

[0183] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , Re and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0184] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0185] R b Hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0186] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0187] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0188] R f C1-C3 alkyl or C1-C3 alkoxy;

[0189] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0190] r 1, 2, 3, 4, 5, or 6;

[0191] n 0, 1, or 2;

[0192] m 0, 1, 2, 3, 4, or 5.

[0193] Further preferred compounds of the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0194] R 1 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;

[0195] R 2 hydrogen;

[0196] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0197] R 4 Hydrogen or fluorine, preferably hydrogen;

[0198] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0199] R 6 hydrogen;

[0200] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0201] X key;

[0202] YZ;

[0203] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0204] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0205] r 1, 2, 3, 4, 5, or 6;

[0206] n 0, 1, or 2;

[0207] m 0, 1, 2, 3, 4, or 5.

[0208] Further preferred compounds of the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0209] R 1Hydrogen, 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;

[0210] R 2 hydrogen;

[0211] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0212] R 4 Hydrogen or fluorine, preferably hydrogen;

[0213] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0214] R 6 hydrogen;

[0215] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0216] X key;

[0217] YZ;

[0218] Z is a 5-membered saturated, partially unsaturated or fully unsaturated carbon ring, which is substituted by m groups selected from the following groups: CO2R e ,CONR b R h , R b , R c , R e and R f ;

[0219] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0220] R b Hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0221] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R aor 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;

[0222] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0223] R f C1-C3 alkyl or C1-C3 alkoxy;

[0224] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0225] m 0, 1, 2, or 3.

[0226] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0227] R 1 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;

[0228] R 2 hydrogen;

[0229] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0230] R 4 Hydrogen or fluorine, preferably hydrogen;

[0231] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0232] R 6 hydrogen;

[0233] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0234] X key;

[0235] YZ;

[0236] Z is a 5-membered saturated, partially unsaturated or fully unsaturated carbon ring, which is substituted by m groups selected from the following groups: CO2R e and R b ;

[0237] R b 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;

[0238] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0239] m 0, 1, 2, or 3.

[0240] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0241] R 1 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;

[0242] R 2 hydrogen;

[0243] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0244] R 4 Hydrogen or fluorine, preferably hydrogen;

[0245] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0246] R 6 hydrogen;

[0247] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0248] X key;

[0249] Y C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine and CO2R e ;

[0250] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0251] m 0, 1, 2, or 3.

[0252] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0253] R 1 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;

[0254] R 2 hydrogen;

[0255] R 3 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0256] R 4 Hydrogen or fluorine, preferably hydrogen;

[0257] R 5 Halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0258] R 6 hydrogen;

[0259] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0260] X key;

[0261] Y C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n Ra 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R 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 ;

[0262] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0263] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0264] R b Hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0265] R cFluorine, 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;

[0266] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0267] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0268] R f C1-C3 alkyl or C1-C3 alkoxy;

[0269] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0270] r 1, 2, 3, 4, 5, or 6;

[0271] m 0, 1, 2, or 3;

[0272] n 0, 1, or 2.

[0273] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0274] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0275] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0276] R 3Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0277] R 4 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0278] R 5 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0279] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0280] R 7 C1-C2 alkyl, cyclopropyl, C1-C2 haloalkyl, C2-C3 alkenyl, C1-C2 alkoxy;

[0281] X key (X 0 ) or a divalent unit selected from the following: (X 1 )、(X 2 )、(X 3 )、(X 4 )、(X 5 ) and (X 6 ):

[0282]

[0283] R 8 -R 13 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R e ,CONR b R d , R a , or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano, or C1-C6 alkoxy, C3-C6 cycloalkyloxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0284] Y cyano, hydroxyl, Z, or C1-C 12Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R 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 ;

[0285] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0286] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0287] R b Hydrogen or R a ;

[0288] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0289] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0290] R e R d ;

[0291] R f C1-C3 alkyl or C1-C3 alkoxy;

[0292] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0293] m 0, 1, 2, 3, 4, or 5;

[0294] n 0, 1, or 2;

[0295] r 1, 2, 3, 4, 5, or 6;

[0296] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0297] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0298] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0299] R 3Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0300] R 4 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0301] R 5 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0302] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0303] R 7 C1-C2 alkyl, cyclopropyl, C1-C2 haloalkyl, C2-C3 alkenyl, C1-C2 alkoxy;

[0304] X key;

[0305] YZ, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine, CO2R e and CONR e S02R a ;

[0306] Z is a 4-5 membered saturated or partially unsaturated ring formed by r carbon atoms, n oxygen atoms, and substituted by m groups selected from the following: CO2R e ,CONR b R h ,CONR e S02R a , R b , R c , R e and R f ;

[0307] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0308] R bHydrogen, 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;

[0309] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0310] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0311] R f C1-C3 alkyl or C1-C3 alkoxy;

[0312] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0313] m 0, 1, 2, 3, 4, or 5;

[0314] n 0, 1, or 2;

[0315] r 1, 2, 3, 4, or 5.

[0316] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0317] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0318] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0319] R 3Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0320] R 4 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0321] R 5 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0322] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0323] R 7 C1-C2 alkyl, cyclopropyl, C1-C2 haloalkyl, C2-C3 alkenyl, C1-C2 alkoxy;

[0324] X key;

[0325] YZ, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine and CO2R e ;

[0326] Z is a 4-5 membered saturated or partially unsaturated ring formed by r carbon atoms, n oxygen atoms, and

[0327] m groups selected from the following substitutions: CO2R e ,CONR b R h , R b , R c , R e and R f ;

[0328] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0329] R b 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;

[0330] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0331] R e hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0332] R f C1-C3 alkyl or C1-C3 alkoxy;

[0333] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0334] m 0, 1, 2, 3, 4, or 5;

[0335] n 0, 1, or 2;

[0336] r 1, 2, 3, 4, or 5.

[0337] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0338] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0339] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0340] R 3 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0341] R 4Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0342] R 5 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0343] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0344] R 7 Fluorine, cyano, or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0345] X key;

[0346] YZ;

[0347] Z is a 4-5 membered saturated or partially unsaturated ring formed by r carbon atoms, n oxygen atoms, and substituted by m groups selected from the following: CO2R e ,CONR b R h , R b , R c , R e and R f ;

[0348] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0349] R b 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;

[0350] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0351] R ehydrogen 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;

[0352] R f C1-C3 alkyl or C1-C3 alkoxy;

[0353] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0354] m 0, 1, 2, 3, 4, or 5;

[0355] n 0, 1, or 2;

[0356] r 1, 2, 3, 4, or 5.

[0357] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0358] R 1 Hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0359] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0360] R 3 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0361] R 4 Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0362] R 5Hydrogen, halogen, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0363] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0364] R 7 Fluorine, cyano or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and C1-C6 alkoxy;

[0365] X key;

[0366] Y C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkynyl, each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d 、Z、OZ、NHZ、S(O) n R a 、SO2NR b R d 、SO2NR b COR e 、CO2R e ,CONR b R h , COR b ,CONR e S02R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b S02R 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 ;

[0367] Z is a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring, excluding phenyl, formed by r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and substituted by m groups selected from the group consisting of: CO2R e ,CONR b R h , R b , R c , R e and R f , and wherein the sulfur atom and the carbon atom carry n oxo groups;

[0368] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy;

[0369] R b Hydrogen or R a ;

[0370] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or C1-C6 alkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0371] R d hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0372] R e R d ;

[0373] R f C1-C3 alkyl or C1-C3 alkoxy;

[0374] R h hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0375] r 1, 2, 3, 4, 5, or 6;

[0376] m 0, 1, 2, 3, 4, or 5;

[0377] n 0, 1, or 2.

[0378] Further preferred compounds according to the invention are compounds of formula (I), in which the substituents have the following meanings:

[0379] R 1 hydrogen;

[0380] R 2 hydrogen;

[0381] R 3 halogen;

[0382] R 4 hydrogen;

[0383] R 5 halogen;

[0384] R 6 hydrogen;

[0385] R 7 C1-C2 alkyl, cyclopropyl, C1-C2 haloalkyl, C2-C3 alkenyl, C1-C2 alkoxy;

[0386] X key;

[0387] YZ, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine and CO2R e ;

[0388] Z is a 4-5 membered saturated or partially unsaturated ring formed by r carbon atoms, n oxygen atoms, and substituted by m groups selected from the following: CO2R e ;

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

[0390] r 4 or 5;

[0391] m 0, 1, 2, 3, 4, or 5;

[0392] n 0 or 1.

[0393] Further preferred embodiments (II and I.II) of the compounds of formula (I) are the following compounds, wherein

[0394] (II):R 1 For hydrogen:

[0395]

[0396] (I.II): R 1 For methyl:

[0397]

[0398] Particularly preferred are compounds of formula (IIa) wherein R 1 , R 2 and R 6 For hydrogen:

[0399]

[0400] Particularly preferred are compounds of formula (IIb) in which R 1 , R 2 , R 4 and R 6 For hydrogen:

[0401]

[0402] Particularly preferred are compounds of formula (IIc) wherein R 1 , R 2 and R 6 is hydrogen, X is a bond (X 0 ) and Y is Z:

[0403]

[0404] Particularly preferred are compounds of formula (IId) in which R 1 , R 2 , R 4 and R 6 is hydrogen, X is a bond (X 0 ) and Y is Z:

[0405]

[0406] Particularly preferred are compounds of formula (I.II.a.) in which R 2 and R 6 is hydrogen and R 1 For methyl:

[0407]

[0408] Particularly preferred are compounds of formula (I.II.b.) in which R 2 , R 4 and R 6 is hydrogen and R 1 For methyl:

[0409]

[0410] In the context of the present invention, particular preference is given to compounds in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1-768 of Table 1 below:

[0411] Table 1: In Table 1, It refers to cyclopropyl.

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422] Particularly preferred are compounds of the formula I.1. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.1.1 - I.1.768:

[0423]

[0424] Particularly preferred are compounds of the formula I.2. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.2.1 - I.2.768:

[0425]

[0426] Particularly preferred are compounds of the formula I.3., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.3.1 - I.3.768:

[0427]

[0428] Particularly preferred are compounds of the formula I.4., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.4.1 - I.4.768:

[0429]

[0430] Particularly preferred are compounds of the formula I.5., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.5.1 to I.5.768:

[0431]

[0432] Particularly preferred are compounds of the formula I.6., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.6.1 - I.6.768:

[0433]

[0434] Particularly preferred are compounds of the formula I.7. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.7.1 - I.7.768:

[0435]

[0436] Particularly preferred are compounds of the formula I.8., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.8.1 - I.8.768:

[0437]

[0438] Particularly preferred are compounds of the formula I.9. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.9.1 - I.9.768:

[0439]

[0440] Particularly preferred are compounds of the formula I.10. wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.10.1 - I.10.768:

[0441]

[0442] Particularly preferred are compounds of the formula I.11. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.11.1 - I.11.768:

[0443]

[0444] Particularly preferred are compounds of the formula I.12. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.12.1 - I.12.768:

[0445]

[0446] Particularly preferred are compounds of the formula I.13., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.13.1 - I.13.768:

[0447]

[0448] Particularly preferred are compounds of the formula I.14. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.14.1 - I.14.768:

[0449]

[0450] Particularly preferred are compounds of the formula I.15., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.15.1 - I.15.768:

[0451]

[0452] Particularly preferred are compounds of formula I.16. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.16.1 - I.16.768:

[0453]

[0454] Particularly preferred are compounds of the formula I.17. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.17.1 - I.17.768:

[0455]

[0456] Particularly preferred are compounds of formula I.18., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.18.1 - I.18.768:

[0457]

[0458] Particularly preferred are compounds of formula I.19. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.19.1 - I.19.768:

[0459]

[0460] Particularly preferred are compounds of formula I.20, wherein R1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.20.1 - I.20.768:

[0461]

[0462] Particularly preferred are compounds of the formula I.21. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.21.1 - I.21.768:

[0463]

[0464] Particularly preferred are compounds of the formula I.22. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.22.1 - I.22.768:

[0465]

[0466] Particularly preferred are compounds of the formula I.23. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.23.1 - I.23.768:

[0467]

[0468] Particularly preferred are compounds of the formula I.24. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.24.1 - I.24.768:

[0469]

[0470] Particularly preferred are compounds of the formula I.25., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.25.1 - I.25.768:

[0471]

[0472] Particularly preferred are compounds of formula I.26., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.26.1 - I.26.768:

[0473]

[0474] Particularly preferred are compounds of formula I.27. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.27.1 - I.27.768:

[0475]

[0476] Particularly preferred are compounds of formula I.28., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.28.1 - I.28.768:

[0477]

[0478] Particularly preferred are compounds of formula I.29. in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.29.1 - I.29.768:

[0479]

[0480] Particularly preferred are compounds of formula I.30. wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.30.1 - I.30.768:

[0481]

[0482] Particularly preferred are compounds of the formula I.31., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.31.1 - I.31.768:

[0483]

[0484] Particularly preferred are compounds of formula I.32., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.32.1 - I.32.768:

[0485]

[0486] Particularly preferred are compounds of formula I.33., in which R 1 , R 2 and R6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.33.1 - I.33.768:

[0487]

[0488] Particularly preferred are compounds of formula I.34., in which R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.34.1 - I.34.768:

[0489]

[0490] Particularly preferred are compounds of formula I.35., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.35.1 - I.35.768:

[0491]

[0492] Particularly preferred are compounds of formula I.36., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.36.1 - I.36.768:

[0493]

[0494] Particularly preferred are compounds of formula I.37., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.37.1 - I.37.768:

[0495]

[0496] Particularly preferred are compounds of formula I.38., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.38.1 - I.38.768:

[0497]

[0498] Particularly preferred are compounds of formula I.39., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.39.1 - I.39.768:

[0499]

[0500] Particularly preferred are compounds of formula I.40. wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.40.1 - I.40.768:

[0501]

[0502] Particularly preferred are compounds of formula I.41., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.41.1 - I.41.768:

[0503]

[0504] Particularly preferred are compounds of formula I.42., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.42.1 - I.42.768:

[0505]

[0506] Particularly preferred are compounds of formula I.43., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.43.1 - I.43.768:

[0507]

[0508] Particularly preferred are compounds of formula I.44., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.44.1 - I.44.768:

[0509]

[0510] Particularly preferred are compounds of formula I.45., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.45.1 - I.45.768:

[0511]

[0512] Particularly preferred are compounds of formula I.46., wherein R 1 , R 2 and R 6 is hydrogen and R3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.46.1 - I.46.768:

[0513]

[0514] Particularly preferred are compounds of formula I.47., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.47.1 - I.47.768:

[0515]

[0516] Particularly preferred are compounds of formula I.48., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.48.1 - I.48.768:

[0517]

[0518] Particularly preferred are compounds of formula I.49., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.49.1 - I.49.768:

[0519]

[0520] Particularly preferred are compounds of formula I.50, wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.50.1 - I.50.768:

[0521]

[0522] Particularly preferred are compounds of formula I.51., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.51.1 - I.51.768:

[0523]

[0524] Particularly preferred are compounds of formula I.52., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.52.1 - I.52.768:

[0525]

[0526] Particularly preferred are compounds of formula I.53., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.53.1 - I.53.768:

[0527]

[0528] Particularly preferred are compounds of formula I.54., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.54.1 - I.54.768:

[0529]

[0530] Particularly preferred are compounds of formula I.55., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e., each compound I.55.1 - I.55.768:

[0531]

[0532] Particularly preferred are compounds of formula I.56., wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and R 7 has the meaning defined in rows 1 to 768 of Table 1 above, i.e. each compound I.56.1 - I.56.768:

[0533]

[0534] The compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry, for example by the following method:

[0535]

[0536] The compounds of formula (I) can be prepared according to methods described in the prior art or analogously thereto. The syntheses make use of starting materials which are either commercially available or can be prepared according to conventional procedures starting from readily available compounds.

[0537] The compound of formula (I) can be prepared from carboxylic acid (III) and commercially available amine (II) using an organic base and a coupling agent. Therefore, the compound of formula (I) can be synthesized from the corresponding carboxylic acid (1 eq.) using a coupling agent (1-2 eq.) such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazole 1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate), an organic base (1-3 eq.) and an amine (II) (1-3 eq.). The reaction is usually carried out in an organic solvent. An aprotic organic solvent is preferably used. Tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN) is most preferably 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.

[0538]

[0539] Carboxylic acids (III) are commercially available or can be prepared from the corresponding esters (IV) (wherein R P is an alkyl or benzyl group). If R P is an alkyl group, the ester (IV) can be cleaved using an aqueous alkali metal hydroxide solution. Lithium hydroxide, sodium hydroxide or potassium hydroxide (1-2 eq.) is preferably used. The reaction is usually carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol or acetonitrile. The reaction is carried out at a temperature of 0-100°C. Preferably, the reaction is carried out at room temperature. If R in (IV) is p If it is benzyl, palladium on carbon (0.001-1 eq.) can be used as a catalyst and hydrogen at a temperature between 0°C and reflux to cleave the ester. Preferably the reaction is carried out at room temperature. An organic solvent is usually used. THF, methanol or ethanol is preferably used.

[0540]

[0541] Ester (IV) can be prepared by mixing N-hydroxybenzene-1-carboximidoyl chloride (V) and 2-oxo-carboxylic acid ester (VI) in the presence of a base, similar to the procedure described in Chem. Ber. 105, 2805-2814 (1972). Preferably, a nitrogen-containing base is used, such as a C1-C6 alkylamine, preferably a tri-C1-C6 alkylamine, such as triethylamine, trimethylamine, N-ethyldiisopropylamine, in an amount of 1-2 equivalents relative to N-hydroxybenzene-1-carboximidoyl chloride (V). 2-oxo-carboxylic acid ester (VI) is used in an amount of 1-10 eq., preferably 2-5 eq.

[0542] The reaction is usually carried out in an organic solvent. Preferably, the organic solvent is an aromatic hydrocarbon, such as benzene, chlorobenzene, toluene, cresol or o-, m- and p-xylene. The reaction is carried out at a temperature of 0-100° C. Preferably, the reaction is carried out at room temperature.

[0543] N-Hydroxybenzene-1-carboimidoyl chloride (V) is commercially available or can be prepared by known methods (eg WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 or WO19145245 and references described therein).

[0544] R on compound (I), (III) or (IV) 7 Further variations on the synthesis may be made by known methods.

[0545] In order to broaden the spectrum of action, the compounds of formula (I) can be mixed with representatives of many other herbicidal or growth regulating active ingredient groups and subsequently applied simultaneously. Suitable components for combination are, for example, herbicides selected from the following classes: acetamides, amides, aryloxyphenoxypropionic esters, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridyls Carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isocyanate Azoles, isocyanates Oxazolidinones, nitriles, N-phenylphthalimides, Oxadiazoles, Oxazolidinediones, glycolamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, o-carbamoylbenzoates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylates, pyridinecarboxamides, pyrimidinediones, pyrimidyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, ureas.

[0546] Furthermore, it may be useful to apply the compounds of formula (I) alone or in combination with other herbicides or in the form of a mixture with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with inorganic salt solutions for treating nutrient and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

[0547] In one embodiment of the present invention, the combination of the present 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 (compound B), preferably herbicides B of groups b1) to b15) and safeners C (compound C).

[0548] In a further embodiment of the invention, the inventive combinations comprise at least one compound of the formula (I) and at least one further active compound B (herbicide B).

[0549] Examples of herbicides B that can be used in combination with the compound A of formula (I) of the present invention are:

[0550] b1) lipid biosynthesis inhibitors selected from the following: ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, Fenoxaprop-ethyl, high Fenoxaprop-P, high 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 (CAS 1033757-93-5), 4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5-acetoxy-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6), 5-acetoxy-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-acetoxy-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-acetoxy-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-2H-pyran-3-one (CAS 1033760-55-2),6-Tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic 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-ylcarboxylic acid methyl ester, 4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS1312340-83-2), 4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

[0551] b2) ALS inhibitors selected from the group consisting of sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, hyl), ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium thyl-sodium), iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, fluoropropyl 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, flumets ulam), florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinyl benzoates such as 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), propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8), sulfonylaminocarbonyltriazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone; wherein the compositions according to the present invention are preferably those comprising at least one imidazolinone herbicide;

[0552] b3) photosynthesis inhibitors selected from the group consisting of amicarbazone, inhibitors of photosystem II, for example 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisothiazolin- oxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisothiazolin-3-yl)- 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidin-2-one (CAS2023785-80-8), 1-(5-tert-butylisothiazolin-1-yl)-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidin-2-one (CAS2023785-80-8), 1-(5-tert-butylisothiazolin-1-yl)-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one oxazolidin-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including chlorotriazines, triazinones, triazinediones, methylthiotriazines and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin uzin), prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin; aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thidiazuron, phenyl carbamates 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. Preferred embodiments of the invention relate to compositions which comprise at least one arylurea herbicide. Preferred embodiments of the invention also relate to compositions which comprise at least one triazine herbicide. Among these, preferred embodiments according to the invention also relate to those compositions which comprise at least one nitrile herbicide;

[0553] b4) a protoporphyrinogen-IX oxidase inhibitor selected from the group consisting of acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flu flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, propargyl Oxadiargyl, oxadiazon, oxyfluorfen, ammonium pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] oxazine-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), (E)-4-[2-chloro-5-(4-chloro-5-difluoromethoxy-1H-methylpyrazol-3-yl)-4-fluorophenoxy]-3-methoxybut-2-enoic acid methyl ester (CAS948893-00-3) 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-methoxyacetic 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 methyl ester (CAS 158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridinyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridinyl]oxy]acetate (CAS 2230679-62-4), 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), ethyl 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]acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);

[0554] b5) from the group consisting of the following bleaching agent 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, fenquintrione, isoquinone isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleaching agent, unknown target: aclonifen, amitrole, flumeturon, 2-chloro-3-methylthio-N-(1-methyltetrazol-5-yl)-4-trifluoromethylbenzamide (CAS1361139-71-0), dichloroisothiazolin Bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isothiazolin Oxazolidinone (CAS 81778-66-7);

[0555] b6) EPSP synthase inhibitors selected from the group consisting of glyphosate, glyphosate-isopropylammonium, glyphosate potassium and glyphosate-trimesium (sulfosate);

[0556] b7) glutamine synthetase inhibitors selected from the group consisting of bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium;

[0557] b8) DHP synthase inhibitors selected from the group consisting of asulam;

[0558] b9) is selected from the group consisting of the following mitotic inhibitors: K1 group compounds: dinitroanilines such as benfluralin, butralin, diinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, aminophosphorus esters such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chl orthal-dimethyl), pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam, K2 group compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; among them, K1 group compounds are preferred, and dinitroanilines are particularly preferred;

[0559] b10) is selected from the group consisting of the following VLCFA inhibitors: chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, and naphthamide-M, tetrazolinones such as fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isopropanols of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9. Oxazoline compounds:

[0560]

[0561] The isocyanate of formula (II) Oxazoline compounds are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0562] Among VLCFA inhibitors, chloroacetamides and hydroxyacetamides are preferred;

[0563] b11) a cellulose biosynthesis inhibitor selected from the group consisting of chlorthiamid, dichlobenil, flupoxam, indazine fluaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenoxy-1- 4-[1,2,4,6]thiatriazine-3-ylamine (CAS 175899-01-1);

[0564] b12) a decoupler herbicide selected from the group consisting of dinoseb, dinoterb and DNOC and its salts;

[0565] b13) is selected from the following 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-hydroxy-propyl)ammonium and its esters, benazolin, benazolin-ethyl ), chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, 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);

[0566] b14) an auxin transport inhibitor selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

[0567] b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleichydrazide, mefluidide, metam, methiozolin, methylazide, methyl bromide, methyl-dymron, methyl iodide iodide), monosodium arsenic (MSMA), oleic acid, chlorine Oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine tetflupyrolimet and tridiphane.

[0568] In addition, it may be useful to apply the compounds of formula (I) in combination with safeners. Safeners are compounds that prevent or reduce damage to useful plants but do not have a significant effect on the herbicidal action of the compounds of formula (I) on undesirable plants. They can be applied before sowing (e.g., during seed treatment, on shoots or rice seedlings) or in a pre-emergence or post-emergence application of useful plants. Safeners and compounds of formula (I) and optionally, herbicide B can be applied simultaneously or sequentially.

[0569] In a further embodiment of the invention, the combinations according to the invention comprise at least one compound of the formula (I) and at least one safener C (component C).

[0570] Examples of safeners are, for example, (quinolin-8-oxy)acetic acids, 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-isothiazolyl-1H- azolecarboxylic acid, dichloroacetamides, α-oximinophenylacetonitrile, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalene dicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acids, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such as amides, esters and thioesters, provided that they have an acid group.

[0571] Examples of safener compounds C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, diphenyl isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3- Oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).

[0572] The active compounds B and active compounds 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, Volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, RR Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995; WH Hanens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994 and KK Hatzios, Herbicide Handbook, 7th edition supplement, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-dichloroacetyl-1,3- Oxazolidine [CAS No. 52836-31-4] is also known as R-29148. 4-Dichloroacetyl-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660.

[0573] The assignment of the respective mechanism of action of the active compounds is based on current knowledge. If several mechanisms of action apply to an active compound, the substance is only assigned to one mechanism of action.

[0574] The invention furthermore relates to formulations comprising at least one auxiliary and at least one compound of the formula (I) according to the invention.

[0575] The formulation comprises a pesticide effective amount of a compound of formula (I). The term "effective amount" means an amount of a combination or compound of formula (I) sufficient to control undesirable plants, especially in crops (i.e. cultivated plants) to control undesirable plants and not produce significant damage to the processed crop plants. This amount can vary over a wide range and depends on various factors such as undesirable plants to be controlled, processed crop plants or materials, climatic conditions and the specific compound of formula (I) used.

[0576] The compounds of formula (I), their salts, amides, esters or thioesters can be converted into the types commonly used in formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, molded products, capsules and mixtures thereof. Examples of formulation types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), molded products (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticide preparations (e.g. LN) and gel formulations for treating plant propagation materials such as seeds (e.g. GF). 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.

[0577] The formulations are prepared in a known manner as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0578] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[0579] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, for example kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactic acid esters, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0580] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of plant origin, for example cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0581] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0582] Suitable anionic surfactants are alkali metals, alkaline earth metals or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acids and mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, sulfonates of dodecyl- and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalene, sulfosuccinates or sulfosuccinamates. Examples of sulfates are 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 are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0583] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0584] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with 1 or 2 hydrophobic groups, or salts of long chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising blocks of polyoxyethylene and polyoxypropylene, or ABC type block polymers comprising alkanol, polyoxyethylene and polyoxypropylene. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[0585] Suitable adjuvants are compounds which have negligible pesticide activity or even no pesticide activity and which improve the biological performance of the compound of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other adjuvants. Other examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0586] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0587] Suitable fungicides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0588] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0589] Suitable defoamers are silicones, long-chain alcohols and fatty acid salts.

[0590] Suitable colorants (for example red, blue or green) are low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (for example iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (for example alizarin colorants, azo colorants and phthalocyanine colorants).

[0591] Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, bio- or synthetic waxes and cellulose ethers.

[0592] Examples of formulation types and their preparation are:

[0593] i) Water-soluble concentrates (SL, LS)

[0594] 10-60% by weight of the 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 other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-15% 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 when diluted with water.

[0595] ii) Dispersible Concentrate (DC)

[0596] 5-25 wt % of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 1-10 wt % of a dispersant (e.g. polyvinyl pyrrolidone) are dissolved in an organic solvent (e.g. cyclohexanone) added to 100 wt %. The mixture is diluted with water to obtain a dispersion.

[0597] iii) Emulsifiable concentrates (EC)

[0598] 15-70 wt % of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-10 wt % of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g. aromatic hydrocarbon) added to 100 wt %. The mixture is diluted with water to obtain an emulsion.

[0599] iv) Emulsion (EW, EO, ES)

[0600] 5-40 wt % of the compound of formula (I) of the present invention or a combination of at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 1-10 wt % of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % of a water-insoluble organic solvent (e.g. aromatic hydrocarbon). The mixture is introduced into 100 wt % of water by means of an emulsifier and made into a homogeneous emulsion. The emulsion is diluted with water to obtain an emulsion.

[0601] v) Suspension (SC, OD, FS)

[0602] In a stirred ball mill, 20-60% by weight of a compound of formula (I) according to the invention or a combination of at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) is ground under the addition of 2-10% by weight of dispersants and wetting agents (e.g. sodium lignin sulfonate and alcohol ethoxylate), 0.1-2% by weight of thickener (e.g. xanthan gum) and up to 100% by weight of water to obtain a finely divided active substance suspension. Dilution with water gives a stable active substance suspension. For FS type formulations, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0603] vi) Water dispersible granules and water soluble granules (WG, SG)

[0604] 50-80% by weight of the 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 other compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground under the addition of up to 100% by weight of dispersants and wetting agents (e.g. sodium lignin sulfonate and alcohol ethoxylate) and is made into water-dispersible or water-soluble granules by means of industrial equipment (e.g. extruder, spray tower, fluidized bed). Dilution with water gives a stable active substance dispersion or solution.

[0605] vii) Water dispersible powders and water soluble powders (WP, SP, WS)

[0606] 50-80% by weight of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) is ground in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g. sodium lignin sulfonate), 1-3% 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 active substance dispersion or solution.

[0607] viii) Gel (GW, GF)

[0608] In a stirred ball mill, 5-25% 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 other compound selected from herbicidal compound B (component B) and safener C (component C) is ground under water with addition of 3-10% by weight of a dispersant (e.g. sodium lignin sulfonate), 1-5% by weight of a thickener (e.g. carboxymethyl cellulose) and up to 100% by weight of water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0609] iv) Microemulsion (ME)

[0610] 5-20 wt% 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 other compound selected from herbicidal compound B (component B) and safener C (component C) is added to 5-30 wt% of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate) and 100 wt% of water. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0611] iv) Microcapsules (CS)

[0612] An oil phase containing 5-50% by weight of a compound of formula (I) of the present invention or a combination of at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50% by weight of a compound of formula (I) of the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbons) and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is 1-10% by weight. The weight % relates to the entire CS formulation.

[0613] ix) Dustable powder (DP, DS)

[0614] 1-10% 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 (e.g. finely divided kaolin).

[0615] x) Particles (GR, FG)

[0616] 0.5-30% 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 other compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground and combined with a solid carrier (e.g. silicate) added to 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.

[0617] xi) Ultra Low Volume Liquid (UL)

[0618] 1-50% 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 other 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 (e.g. an aromatic hydrocarbon).

[0619] Formulation types i) to xi) may optionally comprise further auxiliaries, such as 0.1 to 1% by weight of bactericides, 5 to 15% by weight of antifreeze agents, 0.1 to 1% by weight of antifoams and 0.1 to 1% by weight of colorants.

[0620] The formulations and / or combinations generally comprise 0.01-95% by weight, preferably 0.1-90% by weight and in particular 0.5-75% by weight of the compound of the formula (I).The compound of the formula (I) is used in a purity of 90-100%, preferably 95-100% (according to NMR spectrum).

[0621] For the treatment of plant propagation materials, especially seeds, solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used. The formulations give active substance concentrations of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in the ready-to-use preparations after dilution 2-10 times. (Move down)

[0622] Formula (I) compound, its preparaton and / or combination are in plant propagation material, especially the method for application on seed comprises seed dressing, coating, granulation, dusting, soaking and in-furrow application method of propagation material.Preferably by the method that does not induce germination, for example, by seed dressing, granulation, coating and dusting, formula (I) compound, its preparaton and / or combination are applied respectively on plant propagation material.

[0623] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the compounds of formula (I), formulations and / or combinations containing them as premixes or, if appropriate, added immediately before use (tank mix). These agents may be mixed with the formulations of the invention in a weight ratio of 1:100-100:1, preferably 1:10-10:1.

[0624] The user usually uses the compound of formula (I) of the present invention, the formulation comprising them and / or the combination for a pre-dosage device, a small backpack sprayer, a spray can, a spray aircraft or an irrigation system. Usually the formulation is formulated with water, a buffer and / or other adjuvants to the required application concentration, thereby obtaining a ready-to-use spray liquid or a formulation of the present invention. 20-2000 liters, preferably 50-400 liters of ready-to-use spray liquid are usually used per hectare of agricultural utilization area.

[0625] According to one embodiment, the user can mix the individual components or partially premixed components of the formulation according to the invention, for example the component comprising the compound of formula (I) and optionally, the active substance selected from groups B and / or C), in a spray tank and, if appropriate, add further auxiliaries and additives.

[0626] In a further embodiment, the user can mix the components of the formulations according to the invention, for example the parts of a kit or the parts of a binary or ternary mixture, himself in a spray tank and, if appropriate, add further auxiliaries.

[0627] In another embodiment, the individual components or partially premixed components of the formulations according to the invention, for example the components comprising the compound of formula (I) and, optionally, active substances from groups B and / or C), can be applied jointly (for example after tank mixing) or sequentially.

[0628] The compounds of the formula (I) are suitable as herbicides. They are suitable either directly as a suitable formulation or in combination with at least one further compound selected from the group consisting of the herbicidally active compounds B (component B) and the safeners C (component C).

[0629] The compounds of formula (I) or formulations and / or combinations comprising the compounds of formula (I) are very effective in controlling undesirable plants in non-crop areas, especially at high application rates. They act on broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crops. This effect is mainly observed at low application rates.

[0630] The compounds of formula (I) or formulations and / or combinations comprising them are applied to plants primarily by spraying leaves. Water, for example, can be used here as a carrier by conventional spraying techniques using a spray volume of about 100-1000 l / ha (e.g. 300-400 l / ha). The compounds of formula (I) or formulations and / or combinations comprising them can also be applied by low-volume or ultra-low-volume methods or in microparticle form.

[0631] The application of the compounds of formula (I) or formulations and / or combinations comprising them can be carried out before, during and / or after, preferably during and / or after, the emergence of the undesired plants.

[0632] Application of the compounds of formula (I) or the formulations and / or combinations can be carried out before or during sowing.

[0633] Formula (I) compound or the formulation and / or combination comprising them can be used before emergence, after emergence or before planting, or applied together with the seed of crops. Formula (I) compound or the formulation and / or combination comprising them can also be applied by applying the seed of crops pretreated with formula (I) compound or the formulation and / or combination comprising them. If active component can not be well tolerated by some crops, then it is possible to use wherein by means of spray equipment spray combination so that they do not contact the leaves of sensitive crops as far as possible, and make active component arrive the application technology (afterwards guiding, last tillage program) of the leaf or exposed soil surface of the undesirable plant growing below.

[0634] In another embodiment, the compounds of formula (I) or formulations and / or combinations comprising them can be applied by treating seeds. The treatment of seeds essentially includes all procedures well known to those skilled in the art based on the compounds of formula (I) or formulations and / or combinations prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed coating, seed multilayer coating, seed shelling, seed dripping and seed pelleting). The combination can be applied diluted or undiluted.

[0635] The term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, rice seedlings and similar forms. The preferred term seed here describes corn and seeds. The seeds used can be seeds of the above-mentioned crop plants, but can also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0636] When used in plant protection, the application rates of active substances without formulation auxiliaries, i.e. compounds of the formula (I), component B and, if appropriate, component C, are, depending on the desired effect, 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha and in particular 0.1 to 0.75 kg / ha.

[0637] In a further embodiment of the invention, the application rates of the compounds of the formula (I), component B and, if appropriate, component C are 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha and in particular 0.01 to 2 kg / ha of active substance (as).

[0638] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) of the present invention (total amount of the compound of formula (I)) is 0.1-3000 g / ha, preferably 10-1000 g / ha, depending on the control target, season, target plant and growth stage.

[0639] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is 0.1-5000 g / ha, preferably 1-2500 g / ha or 5-2000 g / ha.

[0640] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is 0.1-1000 g / ha, preferably 1-750 g / ha, more preferably 5-500 g / ha.

[0641] The desired application rate of the herbicidal compound B is usually 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[0642] The required application rates of safener C are generally 0.0005 to 2.5 kg / ha, preferably 0.005 to 2 kg / ha or 0.01 to 1.5 kg / ha as.

[0643] In the treatment of plant propagation material such as seeds, for example by dusting, coating or impregnating seeds, the amount of active substance required is usually 0.1-1000 g, preferably 1-1000 g, more preferably 1-100 g, most preferably 5-100 g per 100 kg of plant propagation material (preferably seeds).

[0644] In a further embodiment of the invention, for the treatment of seed, the active substances, ie the compounds of the formula (I), component B and, if appropriate, component C, are generally applied in amounts of from 0.001 to 10 kg per 100 kg of seed.

[0645] When used to protect materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. In material protection, the amount usually applied is 0.001g-2kg, preferably 0.005g-1kg active substance per cubic meter of treated material.

[0646] In the case of the combinations according to the invention, it is immaterial whether the compound of the formula (I) and the further components B and / or components C are formulated and applied jointly or separately.

[0647] In the case of separate application, the order in which the application is carried out is not very important. It is only necessary that the compound of formula (I) and the other components B and / or components C are applied within a time frame that allows these active ingredients to act on the plants simultaneously, preferably within a time frame of up to 14 days, especially up to 7 days.

[0648] Depending on the method of application, the compounds of the formula (I) or formulations and / or combinations comprising them can additionally be used in a number of other crops for combating undesirable vegetation. Examples of suitable crops are as follows: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oats (Avena sativa), sugar beet (Beta vulgaris spec. altissima), sugar beet (Beta vulgaris spec. rapa), rapeseed (Brassica napus var. napus), turnip (Brassica napus var. napobrassica), turnip (Brassica rapa var. silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), tea (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Carya illinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), small fruit coffee (Coffea arabica) (Coffea canephora) (Coffea canephora, coffee (Coffealiberica), cucumber (Cucumis sativus), dogtooth grass (Cynodon dactylon), carrot (Daucuscarota), oil palm (Elaeis guineensis), European strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum) (tree cotton (Gossypium arboreum), grass cotton (Gossypium herbaceum), Gossypium vitifolium), sunflower (Helianthus annuus), Hevea brasiliensis, barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglansregia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersiconlycopersicum), apple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicagosativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pistachio (Pistacia vera), Pisum sativum, European sweet cherry (Prunus avium), Prunus persica, pear (Pyrus communis), apricot (Prunus armeniaca), European sour cherry (Prunus cerasus), almond (Prunus dulcis) and European plum (Prunus domestica), Ribes sylvestre, castor (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis alba), potato (Solanumtuberosum), Sorghum bicolor (Sorghum vulgare), cocoa (Theobromacacao), red clover (Trifolium pratense), common wheat (Triticum aestivum), triticale (Triticale), durum wheat (Triticum durum), bean (Vicia faba), grape (Vitis vinifera), and maize (Zea mays).

[0649] Preferred crops are groundnut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), kale (Brassica oleracea), lemon (Citrus limon), sweet orange (Citrus sinensis), Coffea arabica (Coffea canephora, Coffea liberica), bermudagrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), bean (Phaseolus vulgaris), pistachio (Pistacia vera), Pisum sativum, almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), bicolor sorghum (Sorghum bicolor) (S. vulgare), triticale (Triticale), common wheat (Triticum aestivum), durum wheat (Triticum durum), bean (Vicia faba), grape (Vitis vinifera) and maize (Zea mays).

[0650] Particularly preferred crops are cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or perennial crops.

[0651] The compounds of formula (I) or formulations and / or combinations comprising them according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering to provide the plants with new traits or to modify already existing traits.

[0652] The term "crops" as used herein also includes plants which have been modified by mutagenesis or genetic engineering to provide the plants with new traits or to modify already existing traits (crop plants).

[0653] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques to generate mutations at specific locations in the plant genome. Targeted mutagenesis techniques typically use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases to achieve targeted effects.

[0654] Genetic engineering usually uses recombinant DNA technology that is not easy to obtain by hybridization, mutagenesis or natural recombination under natural conditions to produce modifications in the plant genome. Usually one or more genes are integrated into the genome of the plant to add traits or improve traits. These integrated genes are also referred to as transgenics in the art, and plants comprising such transgenics are called transgenic plants. The plant conversion method usually produces several conversion events, which are different in the genomic position where the transgenic has been integrated. Plants comprising specific transgenics on a specific genomic position are usually described as comprising specific "events", which are mentioned by specific event names. The traits introduced into plants or modified include herbicide tolerance, insect resistance, increased yield and to abiotic conditions, such as tolerance to drought.

[0655] Herbicide tolerance has been generated by the use of mutagenesis as well as by genetic engineering. Plants that have been rendered tolerant to the acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those grown under the names Commercially available plant varieties. However, most herbicide tolerance traits have been generated through the use of transgenics.

[0656] 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 isocyanate have been tested. Herbicide tolerance develops in isoxaflutole and mesotrione.

[0657] Transgenics that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1 and aad-12; for dicamba tolerance: dmo; for oxynil herbicide tolerance: bxn; for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; for ALS inhibitor herbicide tolerance: csr1-2; for HPPD inhibitor herbicide tolerance: hppdPF, W336 and avhppd-03.

[0658] Examples of transgenic maize events comprising herbicide tolerance genes are DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO- -5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but others are not excluded.

[0659] Transgenic soybean events containing herbicide tolerance genes are exemplified by GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT W62, W98, FG72 and CV127, but not excluding others.

[0660] Transgenic cotton events comprising herbicide tolerance genes are exemplified, but not exclusively, 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.

[0661] Examples of transgenic corolla events comprising a herbicide tolerance gene are MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3, but not exclusive of others.

[0662] Insect resistance is mainly produced by transferring the bacterial gene of insecticidal protein into plants. The most commonly used transgenic is the toxin gene of Bacillus spp. and its synthetic variant, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A (a), vip3Aa20. However, genes of plant origin, especially genes encoding protease inhibitors, such as CpTI and pinII are also transferred to other plants. Another method uses transgenic to produce double-stranded RNA in plants and target and lower insect genes. The example of this transgenic is dvsnf7.

[0663] Transgenic corn events comprising insecticidal protein genes or double-stranded RNA are, for example, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098, but others are not excluded.

[0664] Examples of transgenic soybean events comprising an insecticidal protein gene are MON87701, MON87751 and DAS-81419, but not exclusive of others.

[0665] Transgenic cotton events comprising insecticidal protein genes 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, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321, but others are not excluded.

[0666] Increased yield is produced by increasing ear biomass using the transgene athb17, for example, present in maize event MON87403, or increasing photosynthesis using the transgene bbx32, for example, present in soybean event MON87712.

[0667] 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.

[0668] Tolerance to abiotic conditions, especially drought tolerance, was achieved by using the transgene cspB contained by maize event MON87460 and by using the transgene cspB contained by soybean event IND- -5 contains the transgenic Hahb-4 produced.

[0669] Traits are usually combined by combining genes in a conversion event or by combining different events during the breeding process. Preferred combinations of traits are combinations of herbicide tolerance to different classes of herbicides, combinations of insect tolerance to different species of insects, especially combinations of tolerance to Lepidoptera and Coleoptera, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield and combinations of herbicide tolerance and tolerance to abiotic conditions.

[0670] Plants comprising individual or stacked traits and genes and events providing these traits are well known in the art. For example, detailed information about induced or integrated genes and corresponding events can be obtained by the website of the organization "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) and patent applications such as EP3028573 and WO2017 / 011288.

[0671] The use of the compounds of formula (I) of the present invention or formulations and / or combinations comprising them on crops may result in specific effects on crops comprising certain genes or events. These effects may involve changes in growth behavior or changes in tolerance to biotic or abiotic stress factors. Such effects may particularly include increased yield, increased resistance or tolerance to insect, nematode, fungus, bacteria, mycoplasma, virus or viroid pathogens and early vigor, precocious or delayed maturity, cold or heat tolerance and amino acid or fatty acid profile or content changes.

[0672] Furthermore, plants are also included which contain altered or novel components by the use of recombinant DNA technology, in particular to improve raw material production, such as potatoes which produce increased amounts of amylopectin (e.g. potatoes, BASF SE, Germany).

[0673] In addition, it has been found that the compounds of formula (I) of the present invention or formulations and / or combinations comprising them are also suitable for defoliation and / or drying of plant parts of crops such as cotton, potatoes, rapeseed rape, sunflower, soybean or broad bean, especially cotton. In this regard, formulations and / or combinations for crop drying and / or defoliation, methods for preparing these formulations and / or combinations, and methods for drying and / or defoliating plants using compounds of formula (I) have been found.

[0674] As desiccants, the compounds of formula (I) are particularly suitable for drying the aerial parts of crops such as potatoes, rapeseed, sunflower and soybeans and also cereals. This makes fully mechanized harvesting of these important crops possible.

[0675] Also of economic interest is the promotion of the harvest of citrus fruits, olives and other species and varieties of pome, drupes and nuts, which is made possible by concentrated cracking or reduced adhesion to the tree over a certain period of time. The same mechanism, i.e. the promotion of the production of abscission tissue between the fruit part or leaf part and the branch part of the plant, is also necessary for the controlled defoliation of useful plants, especially cotton.

[0676] Additionally, the shortened time interval between the maturation of individual cotton plants results in improved fiber quality after harvest.

[0677] A Chemical Examples

[0678] Chemical bonds drawn as bars in chemical formulas represent relative stereochemistry on the ring system. Example

[0679] Example 1: (3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl Synthesis of 5-oxazole-5-carbonyl]amino]butyric acid methyl ester (Cpd.I3)

[0680] Step 1:

[0681]

[0682] To a mixture of (1Z)-3,5-dichloro-N-hydroxy-benzimidoyl chloride (CAS 677727-73-0; 3 g, 13.33 mmol) and 3,3,3-trifluoro-2-oxopropanoic acid methyl ester (10.4 g, 66.66 mmol) in toluene (50 ml) at 25°C was added triethylamine (1.36 g, 13.33 mmol) in toluene (20 ml) and the mixture was stirred at 25°C for 5 hours. The mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The crude material was purified by column chromatography (petroleum ether: ethyl acetate = 100: 1-10: 1) to give 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl as a yellow oil. Methyl oxadiazole-5-carboxylate (3.6 g, 82%).

[0683] 1 H NMR (400MHz, CDCl3): δ7.73 (d, J = 1.88Hz, 2H) 7.57 (t, J = 1.82Hz, 1H) 3.99 (s, 3H)

[0684] Step 2:

[0685]

[0686] 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl was added at 25°C. To a mixture of oxadiazole-5-carboxylic acid methyl ester (1 g, 3.31 mmol) in THF / H2O (12 ml / 4 ml) was added lithium hydroxide (278 mg, 6.62 mmol) and the mixture was stirred at 25°C for 2 hours. The mixture was poured into water, the pH was adjusted to pH = 3, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) gave 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl as a white solid. Oleoxazole-5-carboxylic acid (700 mg, 64%). 1 H NMR (400MHz, CDCl3): δ7.94 (t, J=1.82Hz, 1H) 7.73 (d, J=1.88Hz, 2H)

[0687] Step 3:

[0688]

[0689] 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl was added at 25°C. To a mixture of oxadiazole-5-carboxylic acid (1.1 g, 3.37 mmol) in dichloromethane (20 ml) were added dimethylformamide (1 drop) and (COCl)2 (641.35 mg, 5.05 mmol). The mixture was stirred at 25 ° C for 1 hour. The mixture was concentrated, dissolved in dichloromethane (5 mL) and added dropwise to (3S)-3-aminobutyric acid methyl ester hydrochloride (834 mg, 5.05 mmol) in pyridine (22 ml) at 0 ° C. The resulting mixture was stirred at 25 ° C for 2 hours. The mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with brine, dried and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) gave (3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dichlorophenyl] ... [0130 mg, 9%) of methyl [(1-oxazole-5-carbonyl]amino]butyrate. 1 H NMR (400MHz, CDCl3): δ7.75 (t, J = 1.7Hz, 2H), 7.57 (s, 1H), 7.52-7.40 (m, 1H) ,4.49-4.34(m,1H),3.75–3.69(m,3H),2.69-2.53(m,2H),1.35–1.30(m,3H)

[0690] High performance liquid chromatography: HPLC column Kinetex XB C18 1.7μ (50x2.1 mm); eluent: acetonitrile / water+0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 at 60°C in 1.5 minutes, flow rate gradient from 0.8 to 1.0 ml / min in 1.5 minutes).

[0691] Analogously to the above examples, starting from commercially available diesters and using commercially available amines, the following compounds of formula (I) were prepared, wherein R 1 It is hydrogen:

[0692]

[0693] Table 2

[0694] HPLC / MS = mass to charge ratio

[0695]

[0696]

[0697] B. Application Examples

[0698] The herbicidal activity of the compounds of formula (I) was confirmed by the following greenhouse test:

[0699] The culture containers used were plastic pots containing loamy sand containing about 3.0% humus as a substrate. The seeds of the test plants were sown individually for each variety.

[0700] For the pre-emergence treatment, the active ingredient suspended or emulsified in water is applied directly after sowing with the aid of a fine distribution nozzle. The containers are gently irrigated to promote germination and growth and then covered with a transparent plastic cover until the test plants have taken root. This covering leads to uniform germination of the test plants, unless this is damaged by the active ingredient.

[0701] For the post-emergence treatment, the test plants are first grown to a height of 3-15 cm, depending on the plant habit, and only then treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants are sown directly and grown in the same container, or they are first grown individually as seedlings and transplanted into the test containers a few days before the treatment.

[0702] The test plants were kept at 10-25°C or 20-35°C, depending on the variety, respectively.

[0703] The test period was 2-4 weeks. During this period the test plants were cared for and their response to the various treatments was evaluated.

[0704] Evaluation was performed using a scale of 0 to 100. 100 means that no test plants emerged or at least the above-ground part was completely damaged, while 0 means no damage or normal growth. Good herbicidal activity was given a score of 80 to 90, while very good herbicidal activity was given a score of 90 to 100.

[0705] The test plants used in the greenhouse experiments were of the following species:

[0706] Bayer Code scientific name ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Wild Oats (Avena fatua) ECHCG Echinocloa crus-galli SETFA Setaria faberi SETVI Setaria viridis

[0707] At an application rate of 1.000 kg / ha, applied by the pre-emergence method:

[0708] Compounds I7, I8 and I10 showed very good herbicidal activity against APESV.

[0709] Compound I8 showed very good herbicidal activity against AMARE.

[0710] Compound I10 showed good herbicidal activity against AMARE.

[0711] Compounds I8 and I10 showed very good herbicidal activity against ECHCG.

[0712] Compound I7 showed good herbicidal activity against ECHCG.

[0713] Compound I7 showed very good herbicidal activity against SETFA.

[0714] At an application rate of 0.500 kg / ha, applied by pre-emergence method:

[0715] Compound I3 showed very good herbicidal activity against AMARE.

[0716] Compound I2 showed good herbicidal activity against APESV.

[0717] Compounds I1, I3, I4, I5 and I6 showed very good herbicidal activity against APESV.

[0718] Compounds I1, I4, I5 and I6 showed very good herbicidal activity against ECHCG.

[0719] At an application rate of 0.250 kg / ha, applied by pre-emergence method:

[0720] Compounds I9 and I11 showed very good herbicidal activity against APESV.

[0721] Compounds I9 and I11 showed good herbicidal activity against AMARE.

[0722] Compound I11 showed very good herbicidal activity against ECHCG.

[0723] At an application rate of 1.000 kg / ha, applied by post-emergence method:

[0724] Compounds I7, I8 and I10 showed very good herbicidal activity against ECHCG.

[0725] Compounds I7 and I8 showed very good herbicidal activity against AMARE.

[0726] Compound I10 showed good herbicidal activity against AMARE.

[0727] Compounds I7, I8 and I10 showed very good herbicidal activity against SETVI.

[0728] At an application rate of 0.500 kg / ha, applied by post-emergence method:

[0729] Compounds I1, I2, I4, I5 and I6 showed very good herbicidal activity against ALOMY.

[0730] Compound I3 showed good herbicidal activity against ALOMY.

[0731] Compounds I3, I4, I5 and I6 showed very good herbicidal activity against AVEFA.

[0732] Compound I2 showed good herbicidal activity against AVEFA.

[0733] Compound I1 showed very good herbicidal activity against ECHCG.

[0734] Compound I6 showed very good herbicidal activity against SETVI.

[0735] Compounds I1, I2, I3, I4 and I5 showed good herbicidal activity against SETVI.

[0736] At an application rate of 0.250 kg / ha, applied by post-emergence method:

[0737] Compounds I9 and I11 showed very good herbicidal activity against ALOMY.

[0738] Compound I9 showed very good herbicidal activity against AVEFA.

[0739] Compound I11 showed very good herbicidal activity against ECHCG.

[0740] Compounds I9 and I11 showed very good herbicidal activity against SETVI.

Claims

1. Compound of formula (I): The substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen; R 3 is a halogen; R 4 is hydrogen; R 5 is a halogen; R 6 is hydrogen; R 7 is C1-C6 alkyl, C2-C6 alkenyl or C1-C6 alkoxy, substituted by m groups selected from fluorine; X is a bond; Y is Z, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from the group consisting of fluorine and CO2R e ; Z is a 4-5 membered saturated or partially unsaturated ring formed by r carbon atoms and n oxygen atoms, and Selected by m CO2R e The group substitution; 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, 2, 3, 4 or 5; n is 0 or 1; r is 4 or 5; Including its agriculturally acceptable salts.

2. The compound according to claim 1, wherein the substituents have the following meanings: R 7 is methyl, chloromethyl, trifluoromethyl, cyclopropyl, vinyl or methoxy.

3. A compound according to claim 1, wherein the substituents have the following meanings: R 7 It is methyl.

4. A compound according to any one of claims 1 to 3, wherein the substituents have the following meanings: Y is C1-C8 alkyl, with m selected from CO2R e The group is substituted.

5. The compound according to any one of claims 1 to 3, wherein the substituents have the following meanings: Y is Z; Z is a cyclobutane, cyclopentane or cyclopentene ring, which is selected from CO2R e The group is substituted.

6. A composition comprising at least one compound according to any one of claims 1 to 5 and an adjuvant commonly used in the formulation of crop protection agents.

7. A composition according to claim 6, comprising a further herbicide.

8. Use of a compound according to any one of claims 1 to 5 or a composition according to claim 6 or 7 for controlling undesirable vegetation.

9. A method for controlling undesirable vegetation, which comprises allowing a herbicidally active amount of at least one compound according to any one of claims 1 to 5 or a composition according to claim 6 or 7 to act on the plants, their seeds or their habitat.

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