Malonamides and their use as herbicides

Abstract

The present invention relates to compounds of formula (I) and their use as herbicides. In said formula, R 1 - R 8 represents a group such as hydrogen, halogen or an organic group such as alkyl, alkenyl, alkynyl or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxy or a linear or cyclic organic group. The invention also relates to compositions comprising such compounds and their use for controlling unwanted plants.

Description

[0001] The present application relates to malonamide compounds and compositions comprising these. The present application also relates to the use of malonamide compounds or corresponding compositions for controlling undesired plants. Furthermore, the present application relates to a method of applying malonamide compounds or corresponding compositions.

[0002] For controlling undesired plants, especially in crops, there is a continuous need for new herbicides having high activity and selectivity and no significant toxicity to humans and animals.

[0003] WO12130798, W014048827, W01404882, WO18228985, WO18228986, WO19034602 and WO19145245 describe 3-phenylisoxazoline-5-carboxamides and their use as herbicides.

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

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

[0006] WO2004 / 098512 describes the use of fluorinated malonamides and malonamide derivatives as modulators of chemokine receptor activity.

[0007] WO2006 / 061136 describes the use of fluorinated malonamide derivatives as gamma-secretase inhibitors for the treatment of Alzheimer’s disease.

[0008] WO2007 / 002248 describes the use of modified malonamides including fluorinated substances for the treatment of cancer.

[0009] WO2007 / 135466 describes the use of fluorinated malonamides containing a fatty chain and a lactone on the other side as immunosuppressants.

[0010] CN104529802 describes the synthesis of fluorinated malonamide compounds.

[0011] The compounds of the prior art are generally insufficiently herbicidally active and / or not satisfactorily selective, especially at low application rates, resulting in a low compatibility with crop plants.

[0012] It was therefore an object of the present application to provide further malonamide compounds having strong herbicidal activity, especially even at low application rates, a sufficiently low toxicity to humans and animals and / or a high compatibility with crop plants. The malonamide compounds should also exhibit a broad spectrum of activity against a large number of different undesired plants.

[0013] These and other purposes are achieved by compounds of formula (I) as defined below, including their agricultural salts, amides, esters or thioesters.

[0014] Therefore, the present invention provides a compound of formula (I):

[0015]

[0016] The substituents have the following meanings:

[0017] 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;

[0018] R 2 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy

[0019] alkyl, C1-C3 haloalkoxy;

[0020] R 3 Hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0021] R 4 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocyclic

[0022] Alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkoxy

[0023] Alkynyl, C1-C3 alkylthio;

[0024] R 5Hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthioyl, C1-C3 alkylsulfinyl

[0025] Acyl group, C1-C3 alkyl sulfonyl group;

[0026] R 6 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0027] R 7 Hydrogen, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C3 hydroxyalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkylthioyl;

[0028] R 8 Hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy;

[0029] X key (X) 0 () or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0030]

[0031] R 10 -R 15 Each independently contains hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyanide, and CO2R. e CONR b R d NR b CO2R e R aOr C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0032] Y: hydrogen, cyano, hydroxyl, Z, or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0033] Z is a 3, 4, 5, or 6-member saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl, formed of r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and substituted by m groups selected from the following: CO2Re CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e ,

[0034] 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

[0035] R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0036] R a C1-C6 alkyl, C2-C4 alkynyl, C3-C6 cycloalkyl or phenyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3 alkoxy;

[0037] R b Hydrogen, C1-C3 alkoxy or R a ;

[0038] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0039] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0040] R d Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furanyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a CONR b R h C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, benzene

[0041] Thioyl, phenylsulfinyl, and phenylsulfonyl;

[0042] R e R d ;

[0043] R f C1-C3 alkyl or C1-C3 alkoxy;

[0044] 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 being determinated by m groups selected from the following groups.

[0045] Substitutes: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0046] m 0, 1, 2, 3, 4 or 5;

[0047] n = 0, 1, or 2;

[0048] o 0, 1, 2, 3 or 4;

[0049] r 1, 2, 3, 4, 5 or 6;

[0050] This includes its agricultural salts, amides, esters, or thioesters, provided that the compound of formula (I) has a carboxyl group.

[0051] The present invention also provides formulations comprising at least one compound of formula (I) and an adjuvant commonly used in the formulation of product protectants.

[0052] The present invention also provides 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).

[0053] The present invention also provides the use of the compound of formula (I) as a herbicide, i.e., for controlling unwanted plants.

[0054] Furthermore, the present invention provides a method for controlling unwanted plants, wherein an effective amount of at least one compound of formula (I) is applied to the plant, its seeds, and / or its growing area.

[0055] If the compound of formula (I) described herein, herbicide compound B, and / or safer agent C can form geometric isomers, such as E / Z isomers, then pure isomers and mixtures thereof can be used according to the present invention.

[0056] If the compound of formula (I) described herein, herbicide compound B, and / or safer agent C have one or more chiral centers and thus exist as an enantiomer or diastereomer, then both pure enantiomers and diastereomers and mixtures thereof may be used according to the present invention.

[0057] If the compounds of formula (I) described herein, herbicidal compound B, and / or safener C have ionizable functional groups, they may also be used in their agronomical salt form. Suitable salts are typically salts of cations whose cations and anions do not adversely affect the activity of the active compound, and acid addition salts of acids.

[0058] Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium and magnesium ions; and transition metal ions, preferably manganese, copper, zinc, and iron ions. Additionally, ammonium and substituted ammonium compounds in which 1-4 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 groups are preferred, including ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, and diisopropylammonium. Ammonium, trimethylammonium, triethylammonium, triisopropylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alcoholamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diethanolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), and others. The ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide, and finally, salts of polyamines such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0059] The main anions of useful acid addition salts are chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanic acids, with formate, acetate, propionate, and butyrate being preferred.

[0060] The carboxyl-containing compounds of formula (I), herbicidal compound B, and / or safener C described herein may be in the form of an acid, in the form of an agriculturally usable salt as described above, or in the form of an agriculturally usable derivative, for example as an amide, such as mono- and di-C1-C6 alkylamides or arylamides, or as an ester, such as an allyl ester, propargyl ester, or C1-C6 alkyl ester. 10 Alkyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl ((tetrahydrofuran-2-yl)methyl) esters, and also as thioesters, for example as C1-C 10 Alkyl thioesters are used. Preferred mono- and di-C1-C6 alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, benzoylamide and 2-chlorobenzoylamide. 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, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl, or 3-butoxypropyl esters. Straight-chain or branched C1-C 10 An example of an alkylthioester is an ethylthioester.

[0061] The terms used in the definition of organic groups in the variables, such as the expression "halogen", are collective terms representing the members of these groups of organic units.

[0062] prefix C x -C y This indicates the possible number of carbon atoms under a specific condition. All hydrocarbon chains can be straight or branched.

[0063] Halogens: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine;

[0064] Alkyl groups and complex groups such as alkoxy, alkylamino, alkathio, and alkoxycarbonyl: alkyl moieties consisting of saturated straight-chain or branched hydrocarbon groups having 1-10 carbon atoms, such as C1-C2. 10Alkyl groups, 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 their positional isomers; nonyl, decyl and their positional isomers;

[0065] Halogenated alkyl groups: straight-chain or branched alkyl groups having 1-10 carbon atoms (as described above), wherein some or all of the hydrogen atoms in these groups are replaced by the aforementioned halogen atoms. In one embodiment, the alkyl group is substituted at least once or completely with a specific halogen atom, preferably fluorine, chlorine, or bromine. In another embodiment, the alkyl group is partially or completely halogenated with different halogen atoms; in the case of mixed halogen substitution, a combination of chlorine and fluorine is preferred. C1-C3 haloalkyl groups are particularly preferred, and C1-C2 haloalkyl groups are more preferred, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, or 1,1,1-trifluoropropyl-2-yl;

[0066] Alkenyl groups, as well as the alkenyl structural portion in complex groups such as alkenyloxy groups, are unsaturated straight-chain or branched hydrocarbon groups having 2-10 carbon atoms and a double bond at any position. According to the invention, small alkenyl groups, such as C2-C4 alkenyl groups, may be preferred; on the other hand, larger alkenyl groups, such as C5-C8 alkenyl groups, may also be preferred. Examples of alkenyl groups include C2-C6 alkenyl groups, such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 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, and 1-methyl-3-butenyl. 2-Methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl -3-Butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

[0067] Halogenated alkenyl groups: alkenyl groups as described above that are partially or completely substituted with fluorine, chlorine, bromine and / or iodine, such as 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;

[0068] Alkynyl groups and complex groups such as the alkynyl group in alkynoxy groups: straight-chain or branched hydrocarbon groups having 2-10 carbon atoms and one or two triple bonds at any position, such as C2-C6 alkynyl groups, including ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

[0069] Halogenated alkynyl: Alynyl groups as described above that are partially or completely substituted with fluorine, chlorine, bromine and / or iodine, such as 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

[0070] Cycloalkyl groups and cycloalkyl moieties in complex groups: monocyclic or bicyclic saturated hydrocarbon groups having 3-10, especially 3-6, carbon ring members, such as C3-C6 cycloalkyl groups, like cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Examples of bicyclic groups include bicyclic [2.2.1]heptyl, bicyclic [3.1.1]heptyl, bicyclic [2.2.2]octyl, and bicyclic [3.2.1]octyl. In this regard, optionally substituted C3-C8 cycloalkyl refers to a cycloalkyl group having 3-8 carbon atoms, wherein at least one hydrogen atom, such as 1, 2, 3, 4, or 5 hydrogen atoms, is substituted by a substituent that is inert under the reaction conditions. Examples of inert substituents are CN, C1-C6 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, and C1-C4 alkoxy-C1-C6 alkyl;

[0071] The halogenated cycloalkyl structural moiety in halogenated heterocyclic alkyl groups and halogenated cycloalkoxy groups, halogenated cycloalkane carbonyl groups, etc.: a monocyclic saturated hydrocarbon group having 3-10 carbon ring members (as described above), wherein some or all of the hydrogen atoms can be replaced by the halogen atoms mentioned above, especially fluorine, chlorine and bromine;

[0072] Cycloalkoxy: a cycloalkyl group as described above that is linked via oxygen;

[0073] Alkoxy groups and alkoxy structural portions in complex groups, such as alkoxyalkyl groups: alkyl groups as defined above connected via oxygen, preferably having 1-10, more preferably 2-6 carbon atoms. Examples include methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-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;

[0074] Haloalkoxy groups: Alkoxy groups as defined above, wherein some or all of the hydrogen atoms in these groups are replaced by the halogen atom, especially fluorine, chlorine, or bromine, as described above under the haloalkyl group. Examples are OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2 3-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-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecylfluoropentoxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy or dodecafluorohexyloxy;

[0075] Hydroxyl group: an OH group linked via an O atom;

[0076] Cyano group: A CN group linked via a C atom;

[0077] Nitro group: A NO2 group linked via an N atom.

[0078] The preferred embodiments of the present invention described below should be understood as being preferred either independently or in combination with each other.

[0079] According to a particular embodiment of the invention, compounds of formula (I) are also preferred, wherein the variables have the following meanings, either independently or in combination:

[0080] The preferred compound according to the present invention is the compound of formula (I), wherein R 1 It is selected from hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, and C1-C3 alkoxy.

[0081] The preferred compound according to the present invention is the compound of formula (I), wherein R 1 It is selected from hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl and C1-C3 alkoxy-C1-C3 alkyl.

[0082] According to the present invention, a preferred compound is a compound of formula (I), wherein R 1 Selected from hydrogen, methyl, and methoxymethyl.

[0083] In particular, R 1 It is hydrogen.

[0084] A further preferred compound according to the present invention is a compound of formula (I), wherein R 2 It is selected from hydrogen, halogens and C1-C3 alkyl groups.

[0085] According to the present invention, a preferred compound is a compound of formula (I), wherein R 2 Selected from hydrogen, fluorine, chlorine and methyl.

[0086] In particular, R 2 It is hydrogen.

[0087] A further preferred compound according to the present invention is a compound of formula (I), wherein R 3 It is selected from hydrogen, halogen, hydroxyl, cyano and C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 haloalkoxy.

[0088] According to the present invention, a preferred compound is a compound of formula (I), wherein R 3 Selected from hydrogen, halogen, methyl, trifluoromethyl, and trifluoromethoxy.

[0089] In particular, R 3 It is hydrogen or halogen, and very specifically chlorine or fluorine.

[0090] A further preferred compound according to the present invention is a compound of formula (I), wherein R 4 Selected from hydrogen and halogens.

[0091] According to the present invention, a preferred compound is a compound of formula (I), wherein R 4 It is selected from hydrogen, fluorine, chlorine and bromine.

[0092] In particular, R 4 It is hydrogen or hydrogen, fluorine or chlorine, and very specifically hydrogen.

[0093] A further preferred compound according to the present invention is a compound of formula (I), wherein R 5 It is selected from hydrogen, halogen, hydroxyl, cyano and C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 haloalkoxy.

[0094] According to the present invention, a preferred compound is a compound of formula (I), wherein R 3 Selected from hydrogen, halogen, methyl, trifluoromethyl, and trifluoromethoxy.

[0095] In particular, R5 It is hydrogen or halogen, and very specifically chlorine or fluorine.

[0096] A further preferred compound according to the present invention is a compound of formula (I), wherein R 6 It is selected from hydrogen, halogens and C1-C3 alkyl groups.

[0097] According to the present invention, a preferred compound is a compound of formula (I), wherein R 6 Selected from hydrogen, fluorine, chlorine and methyl.

[0098] In particular, R 6 It is hydrogen.

[0099] A further preferred compound according to the present invention is a compound of formula (I), wherein R 7 It is selected from hydrogen, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, and C1-C3 hydroxyalkyl.

[0100] According to the present invention, a preferred compound is a compound of formula (I), wherein R 7 Selected from hydrogen, halogen, cyano, and trifluoromethyl.

[0101] In particular, R 7 It is either hydrogen or halogen, most notably fluorine.

[0102] A further preferred compound according to the present invention is a compound of formula (I), wherein R 8 It is selected from hydrogen, C1-C6 alkyl and C3-C6 cycloalkyl.

[0103] According to the present invention, a preferred compound is a compound of formula (I), wherein R 8 Selected from hydrogen and C1-C3 alkyl groups.

[0104] In particular, R 8 It is hydrogen.

[0105] In the compound of formula (I), X is selected from the bond (X). 0 () or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ), of which intramolecular (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 The orientation of ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y.

[0106]

[0107] In the preferred embodiment (Form (IX) 0 In the compound, X is a bond (X 0 ):

[0108]

[0109] In another preferred embodiment (Form (IX) 1 In the compound, X is (X 1 ), of which intramolecular (X) 1 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0110]

[0111] In another preferred embodiment (Form (IX) 2 In the compound, X is (X 2 ), of which intramolecular (X) 2 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0112]

[0113] In another preferred embodiment (Form (IX) 3 In the compound, X is (X 3 ), of which intramolecular (X) 3 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0114]

[0115] In another preferred embodiment (Form (IX) 4 In the compound, X is (X 4 ), of which intramolecular (X) 4 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0116]

[0117] In another preferred embodiment (Form (IX) 5 In the compound, X is (X 5 ), of which intramolecular (X) 5 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0118]

[0119] In another preferred embodiment (Form (IX) 6 In the compound, X is (X 6 ), of which intramolecular (X) 6 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0120]

[0121] A further preferred compound according to the present invention is a compound of formula (I), wherein X is selected from bond (X). 0 Or selected from the following divalent units: 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.

[0122] A further preferred compound according to the present invention is a compound of formula (I), wherein R 10 -R 15 Each is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and 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 cycloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio, each substituted by m groups selected from the following: fluorine.

[0123] According to the present invention, a preferred compound is a compound of formula (I), wherein R 10 -R 15 Each is independently selected from hydrogen, fluorine, chlorine, and CO2R. e CONR b R dOr C1-C6 alkyl, substituted with m groups selected from the following: fluorine or C1-C6 alkoxy, substituted with m groups selected from the following: fluorine.

[0124] In particular, R 10 -R 15 Each is independently selected from halogens, C1-C6 alkyl groups, C1-C3 alkoxy groups, and CO2R. e .

[0125] A further preferred compound according to the present invention is a compound 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 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO2R. e and CONR b R h .

[0126] According to the present invention, a preferred compound is a compound of formula (I), wherein Y is selected from hydrogen, cyano, hydroxyl, Z, or C1-C. 12 Alkyl groups and C3-C8 cycloalkyl groups, each substituted with m groups selected from the following: fluorine, CO2R e and CONR b R h .

[0127] According to the present invention, a preferred compound is a compound of formula (I), wherein Y is selected from C1-C2. 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e Re NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e .

[0128] According to the present invention, a preferred compound is a compound of formula (I), wherein Y is selected from C1-C2. 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine and CO2R. e .

[0129] Specifically, Y is selected from Z, or C1-C. 12 Alkyl groups and C3-C8 cycloalkyl groups, each substituted with m groups selected from the following: fluorine, C1-C2 alkoxy, CO2R e CONR b R h and CONR e SO2R a .

[0130] Very specifically, Y is selected from Z, or C1-C. 12 Alkyl groups and C3-C8 cycloalkyl groups, each substituted with m groups selected from the following: fluorine, C1-C2 alkoxy, CO2R e and CONR b R h .

[0131] According to a preferred embodiment, Y is Z.

[0132] The preferred compound according to the present invention is a compound of formula (I), wherein Z is selected from 4, 5, or 6 saturated, partially unsaturated, fully unsaturated, or aromatic rings, excluding phenyl, and is formed of r carbon atoms and n oxygen atoms, each of which is substituted by m groups selected from the following: CO2R e CONR b R h S(O) n R a SO2NR b R dSO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e R b R c R e and R f Furthermore, the carbon atoms in this molecule have n oxo groups.

[0133] According to the present invention, a preferred compound is a compound of formula (I), wherein Z is selected from 4, 5, or 6 saturated, partially unsaturated, fully unsaturated, or aromatic rings, excluding phenyl rings, and is formed of r carbon atoms and n oxygen atoms, each of which is substituted by m groups selected from the following: CO2R e CONR b R h R b R c R e and R f Furthermore, the carbon atoms in this molecule have n oxo groups.

[0134] A further preferred compound according to the invention is a compound of formula (I), wherein Z is selected from 3, 4, 5, or 6 saturated, partially unsaturated, fully unsaturated, or aromatic rings, excluding phenyl, and is formed of r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c Re and R f Furthermore, the sulfur and carbon atoms in this ion have n oxo groups.

[0135] Representative examples of the above-mentioned 3, 4, 5, or 6-membered saturated, partially unsaturated, completely unsaturated, or aromatic ring structures are as follows:

[0136]

[0137] According to the invention, a preferred compound is a compound of formula (I), wherein Z is selected from a 4- or 5-member 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 SO2R a R b R c R e and R f .

[0138] According to the present invention, a preferred compound is a compound of formula (I), wherein Z is selected from a 5-member saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f .

[0139] A representative example of a 5-member saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the following: [The text abruptly ends here, likely due to an incomplete translation or a missing section.] e CONR b R h CONR e SO2R a R b R c R e and R f The structure is as follows, with arrows indicating bonds to any of the substituents mentioned above:

[0140]

[0141] A preferred example of a 5-member saturated or partially unsaturated ring is formed of 4 carbon atoms and 1 oxygen atom, each substituted by m groups selected from the following: [The text abruptly ends here, so the translation stops.]e CONR b R h CONR e SO2R a R b R c R e and R f The structure is as follows, with arrows indicating bonds with any of the above substituents, preferably with CO2R. e The key:

[0142]

[0143] According to the present invention, a preferred compound is a compound of formula (I), wherein Z is selected from a 5-member saturated or partially unsaturated ring formed of 5 carbon atoms, each substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f .

[0144] A representative example of a 5-member saturated or partially unsaturated ring is formed by 5 carbon atoms, each substituted by m groups selected from the following: [The text abruptly ends here, likely due to an incomplete translation or a missing section.] e CONR b R h CONR e SO2R a R b R c R e and R f The structure is as follows, with arrows indicating bonds to any of the substituents mentioned above:

[0145]

[0146] A preferred example of a 5-member saturated or partially unsaturated ring is formed of 5 carbon atoms, each substituted by m groups selected from the following: [The text abruptly ends here, so the translation stops.] e CONR b R h CONR e SO2R a R b R c R e and R f The structure is as follows, with arrows indicating any of the above substituents, preferably CO2R. e The key:

[0147]

[0148] Specifically, Z is selected from cyclobutyl, cyclopentyl, cyclopentenyl, and tetrahydrofuranyl, each substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f .

[0149] Preferred examples of Z.1-Z.5 are each substituted with m groups selected from the following: the above CO2R e CONR b R h CONR e SO2R a R b R c R e and R f The structure is as follows, where arrow (1) indicates the bonding position with X, and arrows (2) and (3) indicate the bonds with any of the said substituents, particularly with CO2R. e CONR b R h R b R c R e and R f The key:

[0150]

[0151] The preferred compound according to the present invention is the compound of formula (I), wherein each substituent has the following meaning:

[0152] R 1 Hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0153] R 2 hydrogen;

[0154] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0155] R 4 Hydrogen or halogen, preferably hydrogen;

[0156] R 5Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0157] R 6 hydrogen;

[0158] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0159] R 8 hydrogen;

[0160] X key;

[0161] YZ;

[0162] Z 3, 4, 5 or 6 saturated, partially unsaturated, completely unsaturated or aromatic rings, excluding phenyl.

[0163] It is formed by r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0164] R a C1-C6 alkyl, C3-C6 cycloalkyl, or phenyl groups, each substituted by m groups selected from the following:

[0165] Fluorine, chlorine, bromine, iodine, cyanide, and hydroxyl groups;

[0166] R b Hydrogen, C1-C6 alkoxy or R a ;

[0167] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0168] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0169] R eHydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0170] R f C1-C3 alkyl or C1-C3 alkoxy;

[0171] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0172] r 1, 2, 3, 4, 5 or 6;

[0173] n = 0, 1, or 2;

[0174] m 0, 1, 2, 3, 4 or 5;

[0175] o 0, 1, 2, 3, 4.

[0176] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0177] R 1 Hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0178] R 2 hydrogen;

[0179] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably

[0180] Fluorine or chlorine;

[0181] R 4 Hydrogen or halogen, preferably hydrogen;

[0182] R 5 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably

[0183] Fluorine or chlorine;

[0184] R 6 hydrogen;

[0185] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0186] R 8 hydrogen;

[0187] X key;

[0188] YZ;

[0189] Z is a 3, 4, 5, or 6-member saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl, formed of r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and substituted by m groups selected from the following: CO2R e Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0190] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0191] R e Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a And C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0192] r 1, 2, 3, 4, 5 or 6;

[0193] n = 0, 1, or 2;

[0194] m 0, 1, 2, 3, 4 or 5;

[0195] o 0, 1, 2, 3, 4.

[0196] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0197] R 1 hydrogen;

[0198] R 2 hydrogen;

[0199] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0200] R 4 Hydrogen or halogen, preferably hydrogen;

[0201] R5 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0202] R 6 hydrogen;

[0203] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0204] R 8 hydrogen;

[0205] X key;

[0206] YZ;

[0207] Z is a 5-member saturated or partially unsaturated carbon ring, substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0208] R a C1-C6 alkyl, C3-C6 cycloalkyl or phenyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0209] R b Hydrogen, C1-C6 alkoxy or R a ;

[0210] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkenoxy or C3-C6 alkynoxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0211] R e Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, phenyl-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkyl or C3-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;

[0212] R fC1-C3 alkyl or C1-C3 alkoxy;

[0213] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0214] m 0, 1, 2 or 3.

[0215] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0216] R 1 hydrogen;

[0217] R 2 hydrogen;

[0218] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0219] R 4 Hydrogen or fluorine, preferably hydrogen;

[0220] R 5 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0221] R 6 hydrogen;

[0222] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0223] R 8 hydrogen;

[0224] X key;

[0225] YZ;

[0226] Z is a 4- or 5-membered saturated or partially unsaturated carbon ring, substituted by m groups selected from the following: CO2R e CONR e SO2R a and R b ;

[0227] R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0228] R b Hydrogen, C1-C6 alkoxy or R a ;

[0229] R e Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furanyl-C1-C3 alkyl or C2-C4 ynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;

[0230] m = 0, 1, or 2.

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

[0232] R 1 hydrogen;

[0233] R 2 hydrogen;

[0234] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

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

[0236] R 5 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0237] R 6 hydrogen;

[0238] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0239] R 8 hydrogen;

[0240] X key;

[0241] Y is a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 ynyl group, each selected from m groups.

[0242] The following groups are substituted: fluorine and CO2R e ;

[0243] R aC1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3 alkoxy;

[0244] R e Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, furanyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, benzene

[0245] Benzyl sulfinyl and phenyl sulfonyl;

[0246] m = 0, 1, or 2.

[0247] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0248] R 1 hydrogen;

[0249] R 2 hydrogen;

[0250] R 3 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably

[0251] Fluorine or chlorine;

[0252] R 4 Hydrogen or fluorine, preferably hydrogen;

[0253] R 5 Halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably

[0254] Fluorine or chlorine;

[0255] R 6 hydrogen;

[0256] R 7 Hydrogen, cyano, C1-C3 haloalkyl or halogen, preferably fluorine or chlorine;

[0257] R 8 hydrogen;

[0258] X key;

[0259] Y is a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 ynyl group, each selected from m groups.

[0260] The following groups are substituted: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e ,

[0261] POR f R f and C(R) b ) = NOR e ;

[0262] Z 3, 4, 5 or 6 saturated, partially unsaturated, completely unsaturated or aromatic rings, excluding phenyl.

[0263] It is formed by r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0264] R aC1-C6 alkyl, C3-C6 cycloalkyl, or phenyl groups, each substituted by m groups selected from the following:

[0265] Fluorine, chlorine, bromine, iodine, cyanide, and hydroxyl groups;

[0266] R b Hydrogen, C1-C6 alkoxy or R a ;

[0267] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0268] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0269] R d Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, benzene

[0270] Thioyl, phenylsulfinyl, and phenylsulfonyl;

[0271] 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 following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0272] R f C1-C3 alkyl or C1-C3 alkoxy;

[0273] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0274] m = 0, 1, or 2;

[0275] n = 0, 1, or 2;

[0276] o 0, 1, 2, 3 or 4;

[0277] r 1, 2, 3, 4, 5 or 6.

[0278] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0279] 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;

[0280] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0281] Oxygen group;

[0282] R 3 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0283] R 4 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0284] R 5 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkanes

[0285] alkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0286] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0287] Oxygen group;

[0288] R 7 Hydrogen or fluorine;

[0289] R 8 Hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy; X bond (X 0() or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0290]

[0291] R 10 -R 15 Each independently contains hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyanide, and 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 following: fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy or C3-C6 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, CO2R a and C1-C2 alkoxy groups; Y (hydrogen), cyano, hydroxyl, Z (…

[0292] Or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NRb SO2NR b R e ,

[0293] OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0294] Z 3, 4, 5 or 6 saturated, partially unsaturated, completely unsaturated or aromatic rings, excluding phenyl.

[0295] It is formed by r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0296] R a C1-C6 alkyl, C3-C6 cycloalkyl, or phenyl groups, each substituted by m groups selected from the following:

[0297] Fluorine, chlorine, bromine, iodine, cyanide, and hydroxyl groups;

[0298] R b Hydrogen, C1-C6 alkoxy or R a ;

[0299] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0300] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0301] R d Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R aand C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl

[0302] alkyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0303] R e R d ;

[0304] R f C1-C3 alkyl or C1-C3 alkoxy;

[0305] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0306] m 0, 1, 2, 3, 4 or 5;

[0307] n = 0, 1, or 2;

[0308] o 0, 1, 2, 3 or 4;

[0309] r 1, 2, 3, 4, 5 or 6.

[0310] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0311] 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;

[0312] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0313] Oxygen group;

[0314] R 3 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0315] R 4Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0316] R 5 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkanes

[0317] alkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0318] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0319] Oxygen group;

[0320] R 7 Hydrogen, fluorine;

[0321] R 8 Hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy;

[0322] X key;

[0323] YZ, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 ynyl, each substituted by m groups selected from the following: fluorine and CO2R a ;

[0324] Z is a 4 or 5-member saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, and is...

[0325] m groups are selected from the following groups for substitution: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0326] R a C1-C6 alkyl, C3-C6 cycloalkyl, or phenyl groups, each substituted by m groups selected from the following:

[0327] Fluorine, chlorine, bromine, iodine, cyanide, and hydroxyl groups;

[0328] R b Hydrogen, C1-C6 alkoxy or R a ;

[0329] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0330] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: 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 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl

[0332] alkyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0333] R f C1-C3 alkyl or C1-C3 alkoxy;

[0334] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0335] m 0, 1, 2, 3, 4 or 5;

[0336] n = 0, 1, or 2;

[0337] r 1, 2, 3, 4 or 5.

[0338] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0339] 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;

[0340] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0341] Oxygen group;

[0342] R 3 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0343] R 4 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0344] R 5 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkanes

[0345] alkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0346] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0347] Oxygen group;

[0348] R 7 Hydrogen, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C3 hydroxyalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkylthioyl;

[0349] R 8 Hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy;

[0350] X key;

[0351] YZ;

[0352] Z is a 4- or 5-membered saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, and substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0353] R a C1-C6 alkyl, C3-C6 cycloalkyl or phenyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0354] R b Hydrogen, C1-C6 alkoxy or R a ;

[0355] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkenoxy or C3-C6 alkynoxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0356] R e Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a And C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0357] R f C1-C3 alkyl or C1-C3 alkoxy;

[0358] R h Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

[0359] m 0, 1, 2, 3, 4 or 5;

[0360] n = 0, 1, or 2;

[0361] r 1, 2, 3, 4 or 5.

[0362] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0363] 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;

[0364] R 2 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0365] Oxygen group;

[0366] R 3 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0367] R 4 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0368] R 5 Hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 halocycloalkanes

[0369] alkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, C2-C3 haloalkynyl;

[0370] R 6 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkane

[0371] Oxygen group;

[0372] R 7 Hydrogen, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C3 hydroxyalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy

[0373] C1-C3 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkylthioyl;

[0374] R 8 Hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy;

[0375] X key;

[0376] Y C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 Alkyne groups, each divided by m

[0377] Substitution with groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e ,

[0378] OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0379] Z 3, 4, 5 or 6 saturated, partially unsaturated, completely unsaturated or aromatic rings, excluding phenyl.

[0380] It is formed by r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0381] R a C1-C6 alkyl, C3-C6 cycloalkyl, or phenyl groups, each substituted by m groups selected from the following:

[0382] Fluorine, chlorine, bromine, iodine, cyanide, and hydroxyl groups;

[0383] R b Hydrogen, C1-C6 alkoxy or R a ;

[0384] R c Fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a Or C1-C6 alkoxy, C3-C6 alkene

[0385] Oxygen or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0386] R d Hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl

[0387] alkyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0388] R e R d ;

[0389] R f C1-C3 alkyl or C1-C3 alkoxy;

[0390] R hHydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy groups;

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

[0392] n = 0, 1, or 2;

[0393] o 0, 1, 2, 3 or 4;

[0394] r 1, 2, 3, 4, 5 or 6.

[0395] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0396] R 1 hydrogen;

[0397] R 2 hydrogen;

[0398] R 3 halogen;

[0399] R 4 hydrogen;

[0400] R 5 halogen;

[0401] R 6 hydrogen;

[0402] R 7 Hydrogen, halogen, cyano, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 hydroxyalkyl;

[0403] R 8 hydrogen;

[0404] X key;

[0405] YZ, or C1-C8 alkyl, which is substituted by m groups selected from the following: CO2R e ;

[0406] Z is a 5-member saturated or partially unsaturated carbon ring, substituted by m groups selected from the following: CO2R e ;R a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0407] R eHydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, CO2R a and C1-C2 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl

[0408] alkyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

[0409] m 0, 1, 2, 3, 4 or 5.

[0410] Other preferred compounds according to the present invention are compounds of formula (I), wherein each substituent has the following meaning:

[0411] R 1 hydrogen;

[0412] R 2 hydrogen;

[0413] R 3 Halogens, C1-C3 haloalkyl groups, C1-C3 haloalkoxy groups;

[0414] R 4 Hydrogen or halogen;

[0415] R 5 Hydrogen or halogen;

[0416] R 6 hydrogen;

[0417] R 7 Hydrogen, halogen, cyano, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 hydroxyalkyl;

[0418] R 8 hydrogen;

[0419] X key;

[0420] YZ, or C1-C8 alkyl, which is substituted by m groups selected from the following: CO2R e ;

[0421] Z is a 5-member saturated or partially unsaturated carbon ring, substituted by m groups selected from the following: CO2R e ;

[0422] R e Hydrogen or C1-C6 alkyl;

[0423] m 1 or 2.

[0424] Further preferred embodiments (II-I.IV) of the compound of formula (I) are the following compounds, wherein (II): R 1 R 8 For hydrogen:

[0425]

[0426] (I.II): R 1 For hydrogen, R 8 Methyl:

[0427]

[0428] (I.III): R 1 Methyl, R 8 Methyl:

[0429]

[0430] (I.IV): R 1 Methyl, R 8 For hydrogen:

[0431]

[0432] Particularly preferred compound (IIa), wherein R 1 R 2 R 6 and R 8 For hydrogen:

[0433]

[0434] Compound of formula (IIb) is also particularly preferred, wherein R 1 R 2 R 4 R 6 and R 8 For hydrogen:

[0435]

[0436] Particularly preferred compounds (IIc), wherein R 1 R 2 R 6 and R 8 Hydrogen, X is a bond (X 0 And Y is Z:

[0437]

[0438] Also particularly preferred are compounds of formula (IId), wherein R 1 R 2 R4 R 6 and R 8 Hydrogen, X is a bond (X 0 And Y is Z:

[0439]

[0440] Compounds of formula (I.II.a.) are particularly preferred, wherein R 1 R 2 R 6 It is hydrogen and R 8 Methyl:

[0441]

[0442] Compounds of formula (I.II.b.) are particularly preferred, wherein R 1 R 2 R 4 R 6 It is hydrogen and R 8 Methyl:

[0443]

[0444] Compounds of formula (I.III.a.) are particularly preferred, wherein R 2 R 6 It is hydrogen and R 1 R 8 Methyl:

[0445]

[0446] Compounds of formula (I.III.b.) are particularly preferred, wherein R 2 R 4 R 6 It is hydrogen and R 1 R 8 Methyl:

[0447]

[0448] Compounds of formula (I.IV.a.) are particularly preferred, wherein R 1 It is methyl and R 2 R 6 and R 8 For hydrogen:

[0449]

[0450] Also particularly preferred are compounds of formula (I.IV.b.), wherein R 1 It is methyl and R 2 R 4 R 6and R 8 For hydrogen:

[0451]

[0452] In the context of this invention, the following compounds are particularly preferred, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 It has the meanings defined in rows 1-1152 of Table 1 below:

[0453] Table 1:

[0454] In Table 1, It refers to cyclopropyl.

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470] Particularly preferred compound I.1, wherein R 1 R 2 R 6 and R8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.1.1-I.1.1152:

[0471]

[0472] Particularly preferred compound I.2, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.2.1-I.2.1152:

[0473]

[0474] Particularly preferred compound I.3, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.3.1-I.3.1152:

[0475]

[0476] Particularly preferred compound I.4, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.4.1-I.4.1152:

[0477]

[0478] Particularly preferred compound I.5, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.5.1-I.5.1152:

[0479]

[0480] Particularly preferred compound I.6, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.6.1-I.6.1152:

[0481]

[0482] Particularly preferred compound I.7, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.7.1-I.7.1152:

[0483]

[0484] Particularly preferred compound I.8, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.8.1-I.8.1152:

[0485]

[0486] Particularly preferred compound I.9, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.9.1-I.9.1152:

[0487]

[0488] Particularly preferred compound I.10, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.10.1-I.10.1152:

[0489]

[0490] Particularly preferred compound I.11, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.11.1-I.11.1152:

[0491]

[0492] Particularly preferred compound I.12, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.12.1-I.12.1152:

[0493]

[0494] Particularly preferred compound I.13, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.13.1-I.13.1152:

[0495]

[0496] Particularly preferred compound I.14, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.14.1-I.14.1152:

[0497]

[0498] Particularly preferred compound I.15, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.15.1-I.15.1152:

[0499]

[0500] Particularly preferred compound I.16, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.16.1-I.16.1152:

[0501]

[0502] Particularly preferred compound I.17, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.17.1-I.17.1152:

[0503]

[0504] Particularly preferred compound I.18, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.18.1-I.18.1152:

[0505]

[0506] Particularly preferred compound I.19, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.19.1-I.19.1152:

[0507]

[0508] Particularly preferred compound I.20, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.20.1-I.20.1152:

[0509]

[0510] Particularly preferred compound I.21, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.21.1-I.21.1152:

[0511]

[0512] Particularly preferred compound I.22, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.22.1-I.22.1152:

[0513]

[0514] Particularly preferred compound I.23, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.23.1-I.23.1152:

[0515]

[0516] Particularly preferred compound I.24, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.24.1-I.24.1152:

[0517]

[0518] Particularly preferred compound I.25, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.25.1-I.25.1152:

[0519]

[0520] Particularly preferred compound I.26, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.26.1-I.26.1152:

[0521]

[0522] Particularly preferred compound I.27, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.27.1-I.27.1152:

[0523]

[0524] Particularly preferred compound I.28, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.28.1-I.28.1152:

[0525]

[0526] Particularly preferred compound I.29, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.29.1-I.29.1152:

[0527]

[0528] Particularly preferred compound I.30, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.30.1-I.30.1152:

[0529]

[0530] Particularly preferred compound I.31, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.31.1-I.31.1152:

[0531]

[0532] Particularly preferred compound I.32, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.32.1-I.32.1152:

[0533]

[0534] Particularly preferred compound I.33, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.33.1-I.33.1152:

[0535]

[0536] Particularly preferred compound I.34, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.34.1-I.34.1152:

[0537]

[0538] Particularly preferred compound I.35, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.35.1-I.35.1152:

[0539]

[0540] Particularly preferred compound I.36, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.36.1-I.36.1152:

[0541]

[0542] Particularly preferred compound I.37, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.37.1-I.37.1152:

[0543]

[0544] Particularly preferred compound I.38, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.38.1-I.38.1152:

[0545]

[0546] Particularly preferred compound I.39, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.39.1-I.39.1152:

[0547]

[0548] Particularly preferred compound I.40, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.40.1-I.40.1152:

[0549]

[0550] Particularly preferred compound I.41, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.41.1-I.41.1152:

[0551]

[0552] Particularly preferred compound I.42, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.42.1-I.42.1152:

[0553]

[0554] Particularly preferred compound I.43, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.43.1-I.43.1152:

[0555]

[0556] Particularly preferred compound I.44, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.44.1-I.44.1152:

[0557]

[0558] Particularly preferred compound I.45, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.45.1-I.45.1152:

[0559]

[0560] Particularly preferred compound I.46, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.46.1-I.46.1152:

[0561]

[0562] Particularly preferred compound I.47, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.47.1-I.47.1152:

[0563]

[0564] Particularly preferred compound I.48, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.48.1-I.48.1152:

[0565]

[0566] Particularly preferred compound I.49, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.49.1-I.49.1152:

[0567]

[0568] Particularly preferred compound I.50, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.50.1-I.50.1152:

[0569]

[0570] Particularly preferred compound I.51, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.51.1-I.51.1152:

[0571]

[0572] Particularly preferred compound I.52, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.52.1-I.52.1152:

[0573]

[0574] Particularly preferred compound I.53, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.53.1-I.53.1152:

[0575]

[0576] Particularly preferred compound I.54, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.54.1-I.54.1152:

[0577]

[0578] Particularly preferred compound I.55, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, namely, each compound I.55.1-I.55.1152:

[0579]

[0580] Particularly preferred compound I.56, wherein R 1 R 2 R 6 and R 8 It is hydrogen and R 3 R 4 R 5 and R 7 These have the meanings defined in rows 1-1152 of Table 1 above, i.e., each compound I.56.1-I.56.1152:

[0581]

[0582] Compounds of formula (I) according to the present invention can be prepared by standard organic chemistry methods, for example by the following methods:

[0583]

[0584] Compounds of formula (I) can be prepared according to methods described in the prior art or similar methods. Synthesis utilizes starting materials that are commercially available or can be prepared from readily available compounds according to conventional procedures.

[0585] Compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling agent. Therefore, compounds 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-azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate), an organic base (1-3 eq.), and an amine (II) (1-3 eq.). The reaction is generally carried out in an organic solvent. Aprotic organic solvents are preferred. Tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) are most preferred. The reaction is carried out at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[0586]

[0587] Carboxylic acid (III) can be commercially available or can be derived from the corresponding ester (IV) (wherein R) P It is prepared by (either alkyl or benzyl). If R P If it is an alkyl group, the ester (IV) can be cleaved using an aqueous solution of an alkali metal hydroxide. Lithium hydroxide, sodium hydroxide, or potassium hydroxide (1-2 eq.) is preferred. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol, or acetonitrile. The reaction is carried out at a temperature of 0-100°C. Preferably, the reaction is carried out at room temperature. If R in (IV) p If the ester is benzyl, it can be cleaved using carbon-supported palladium (0.001-1 eq.) as a catalyst and hydrogen at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature. Organic solvents are typically used. THF, methanol, or ethanol are preferred.

[0588]

[0589] Compounds of formula (IV) can be prepared from carboxylic acids (VI) and commercially available amines (V) using a base and a coupling agent. Therefore, compounds of formula (IV) 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-azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate), an organic base (1-3 eq.), and an amine (V) (1-3 eq.). The reaction is generally carried out in an organic solvent. Aprotic organic solvents are preferred. Tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) are most preferred. The reaction is carried out at a temperature between 0°C and reflux temperature. Preferably, the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[0590]

[0591] Carboxylic acids (VI) can be prepared from the corresponding diesters by selectively cleaving an ester group. If R q If the ester is an alkyl ester, selective ester cracking can be achieved using an aqueous alkali. Alkali metal hydroxides are preferred. Lithium hydroxide, sodium hydroxide, or potassium hydroxide are most preferred. The reaction is typically carried out in a mixture of water and an organic solvent. THF, methanol, or acetonitrile are preferred. The reaction is carried out at a temperature of 0-100°C, preferably at room temperature.

[0592] Alternatively, trimethyltin hydroxide (e.g., 1 eq.) in 1,2-dichloroethane at room temperature to reflux (as described in Angew. Chem. Int. Ed., 2005, 44: 1378-1382) can be used, preferably under reflux. If R in (VII) q If the ester is benzyl, it can be cleaved using carbon-supported palladium (0.001-1 eq.) as a catalyst and hydrogen at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature. Organic solvents are typically used. THF, methanol, or ethanol are preferred.

[0593]

[0594] Fluorinated diesters (VII) can be commercially available or prepared from the corresponding diesters (VIII) using an electrophilic fluorinating agent and a suitable base. Preferred agents include selectfluor (N-chloromethyl-N'-fluorotriethylenediammonium (tetrafluoroborate)), NFSI (N-fluorobenzenesulfonylimide), NFOBS (N-fluoroophthalic acid disulfonylimide), and 1-fluoropyridine. Tetrafluoroborate, 1-fluoropyridine Trifluoromethanesulfonate, 1-fluoro-2,4,6-trimethylpyridine Tetrafluoroborate, 1-fluoro-2,4,6-trimethylpyridine Trifluoromethanesulfonate and 2-fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide are used as electrophilic fluorinating agents. Selectfluor, NFSI, and NFOBS are most preferred. Alkali metal hydrides, alkali metal amines, and inorganic bases are preferred. Sodium hydride, bis(trimethylsilyl)aminolithium, diisopropylaminolithium, and potassium carbonate are most preferred. The reaction is generally carried out in aprotic organic solvent at a temperature between -78°C and room temperature. Dimethylformamide (DMF), dimethylacetamide (DMA), THF, diethyl ether, and acetonitrile are preferred.

[0595] To broaden the spectrum of action, the compound of formula (I) can be mixed with representatives of many other herbicidal or plant growth-regulating active ingredients and then applied simultaneously. Suitable components for combination include, for example, herbicides selected from the following categories: acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, and bipyridines. Carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isocyanates azoles, isotonic Alzolidine ketones, nitriles, N-phenylbenzodicarboximides, diazoles, Alzolidinediones, hydroxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, hypophosphino acids, aminophosphates, dithiophosphates, o-carbamoylbenzoates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridine carboxamides, pyrimidinediones, pyrimidine (thio)benzoates, quinolinecarboxylic acids, amine ureas, sulfonamide carbonyl triazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triones, uracils, and ureas.

[0596] Furthermore, it may be beneficial to apply Formula (I) compounds alone or in combination with other herbicides or in mixtures with other crop protectants, such as with agents for controlling pests or plant pathogenic fungi or bacteria. Also of interest is the miscibility with solutions of inorganic salts used to treat nutrient and trace element deficiencies. Other additives, such as non-vegetarian toxic oils and oil concentrates, may also be added.

[0597] In one embodiment of the invention, the present invention comprises at least one compound of formula (I) (compound A or component A) and at least one other active compound selected from herbicide B (compound B), preferably herbicide B of group b1)-b15) and safener C (compound C).

[0598] In another embodiment of the invention, the present invention comprises at least one compound of formula (I) and at least one other active compound B (herbicide B).

[0599] Examples of herbicides B that can be used in combination with compound A of formula (I) of the present invention include:

[0600] b1) Selected from the following lipid biosynthesis inhibitors: ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, and diclofop-methyl. fenoxaprop fenoxaprop-ethyl, high Fenoxaprop-P, high Fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl Metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-teefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefury l), 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 (CAS1312337-72-6), 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-45-3) ), 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1033757-93-5), 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS1312340-84-3), 5-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 (CAS1312337-48-6), 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 (CAS1312340-82-1), 5-acetoxy-4-(2',4'-dichloro-4-ethyl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312340-82-1), 5-acetoxy-4-(2',4'-dichloro-4-ethyl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one

[0601] [1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), methyl 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylate (CAS1312337-51-1), methyl 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2, Methyl 2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylate, methyl 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-ylcarboxylate (CAS1312340-83-2), 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl) Methyl 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylate (CAS1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, and butane.

[0602] Tiocarbazil, triallate, and vernolate;

[0603] b2) Selected ALS inhibitors from the following: sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-met hyl), ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-me thyl-sodium), iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, fluoropropiosulfuron Prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfurosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methylTrifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron; imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, and imazethapyr; triazolopyrimidine herbicides; and sulfonylanilines such as cloransulam, cloransulam-methyl, diclosulam, and flumets. ulam), florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxsulam; pyrimidinyl benzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, and 1-methylethyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 1-methylethyl ester) 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl],

[0604] [Methyl]amino]propyl benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8), sulfonylaminocarbonyl triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone; wherein preferred embodiments of the invention relate to those groups comprising at least one imidazolinone herbicide.

[0605] Compounds;

[0606] b3) Selected from the following photosynthesis inhibitors: amicabazone, photosynthetic system II inhibitors

[0607] Formulations, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS1654744-66-7), 1-(5-tert-butylisothiazolinone) (-3-yl)-2-hydroxy-4-methoxy

[0608] 3-Methyl-2H-pyrrolo-5-one (CAS1637455-12-9), 1-(5-tert-butylisothiazolinone) 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrolo-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrolo-5-one (CAS 1637453-94-1) 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrolo-5-one (CAS1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidine-2-one (CAS2023785-80-8), 1-(5-tert-butylisocyanate) (3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidine-2-one (CAS 1844836-64-1), a triazine herbicide, including chlorotriazines, triazinones, triazindiones, methylthiotriazines, and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, and metribuzin. Herbicides such as uzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin; arylureas such as chlorobromuron, chlorotoluron, chloroxuron, and butyl... Dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and thidiazuron; phenylcarbamates such as desmedipham, karbutilat, phenmedipham, and phenmedipham-ethyl The herbicides include nitrile herbicides such as bromofenoxim, bromoxynil and their salts and esters, ioxynil and their salts and esters; uracil herbicides such as bromacil, lenacil and terbacil; bentazon and bentazon-sodium; pyridate, pyridafol, pentanochlor and propanil; and photosynthetic system I inhibitors such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Preferred embodiments of the invention relate to compositions comprising at least one arylurea herbicide. Preferred embodiments of the invention also relate to compositions comprising at least one triazine herbicide. The preferred embodiments of the present invention also relate to those groups comprising at least one nitrile herbicide.

[0609] Compounds;

[0610] b4) Selected from the following protoporphyrinogen-IX oxidase inhibitors: acifluorfen, flufenoxuron, etc.

[0611] Acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, fluorine Flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactoferrin, propargite Oxadiargyl, oxadiazon, oxyfluorfen, and pendimethalin Pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridinoxy]ethyl acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 353292-31-6; S-3100) 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] [1,3,5]triazinan-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]) (azinindol-6-yl)-4,5,6,7-tetrahydroisoindol-1,3-dione (CAS1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]) Methyl methoxy-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-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-trifluoromethyl-1H-benzimidazol-4-yl]-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (CAS 212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]- 4-Fluorophyl]-2-methoxyacetic acid methyl ester (CAS1970221-16-9), 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 (CAS2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]

[0612] Ethyl acetate [[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy]methyl acetate (CAS 2271389-22-9), ethyl acetate [[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy] 2230679-62-4), methyl acetate of 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 (CAS2158275-73-9), methyl acetate of 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid Ethyl ester (CAS2158274-56-5), 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-(methanesulfonyl)-acetamide (CAS2158274-53-2), 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

[0613] [N-(methylsulfonyl)-acetamide (CAS2158276-22-1);]

[0614] b5) Selected from the following bleaching herbicides: PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7); HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clonazol, fenquintrione, and isoxaflutole. Fluoride (isoxaflutole), mesotrione, oxotrione (CAS1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleaching agents, unknown targets: aclonifen, amitrol, flumeturon, 2-chloro-3-methylthio-N-(1-methyltetrazole-5-yl)-4-trifluoromethylbenzamide (CAS1361139-71-0), dichloroisocyanurate Bixlozone and 2-(2,5-dichlorophenyl)

[0615] Methyl-4,4-dimethyl-3-isomethyl Azoxystrobin (CAS 81778-66-7);

[0616] b7) Selected from the following glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, and glufosinate-ammonium.

[0617] b8) Selected from the following DHP synthase inhibitors: asulam;

[0618] b9) Selected from the following mitotic inhibitors: K1 group compounds: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin; aminophosphates such as amiprophos, amiprophos-methyl, and butamiphos; benzoic acid herbicides such as chlorthal and chlorpyrifos. 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 which K1 group compounds are preferred, especially dinitroanilines;

[0619] b10) is selected from the following VLCFA inhibitors: chloroacetamides such as acetochlor, etc.

[0620] Alachlor, Midochlor, Butachlor, Dimethachlor, Dimethanamid, Dimethenamid-P, Mettachlor, Mettachlor, Mettachlor-S, Pethoxamid, Pretilachlor, Propachlor, Proisochlor, and Thenylchlor, as well as oxyacetanilides such as Flufenoxuron. Nacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide, and other herbicides such as ailofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isocyanates of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 Azoline compounds:

[0621]

[0622] Equation (II) Azoline compounds are known in the art, for example by WO 2006 / 024820, WO2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0623] Among VLCFA inhibitors, chloroacetamides and hydroxyacetamides are preferred;

[0624] b11) is selected from the following cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indazon, isoxaben, triaziflam, and 1-cyclohexyl-5-pentafluorophenoxy-1 4 -[1,2,4,6]thiatriazine-3-ylamine (CAS175899-01-1);

[0625] b12) is selected from the following decoupling herbicides: dinoseb, dinoterb, and dinitrocresol (DNOC) and their salts;

[0626] b13) Selected from the following plant growth regulator 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, benzolin, benzolin-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, floppyrauxifen, 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, triclipyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS1390661-72-9), and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridinecarboxylic acid (CAS1629965-65-6);

[0627] b14) is selected from the following plant auxin transport inhibitors: diflufenzopyr, diflufenozide ...

[0628] Diflufenzopyr-sodium, naptalam, and naptalam-sodium;

[0629] b15) Selected from the following herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 15) 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, sodium 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 iodomethyl iodide), sodium methylarsine (MSMA), oleic acid, chloride Oxaziclomefone, pelargonicacid, pyributicarb, quinoclamine

[0630] tetflupyrolimet and tridiphane.

[0631] Furthermore, it may be useful to apply the compound of formula (I) in combination with a safener. A safener is a compound that prevents or reduces damage to the beneficial plant but does not significantly affect the herbicidal effect of the compound of formula (I) on the unwanted plant. They can be applied before sowing (e.g., at seed treatment, on shoots or seedlings) or pre- or post-emergence of the beneficial plant. The safener and the compound of formula (I), and optionally, herbicide B, can be applied simultaneously or sequentially.

[0632] In another embodiment of the invention, the present invention combination comprises at least one compound of formula (I) and at least one safer agent C (component C).

[0633] Examples of safeners include (quinoline-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, and 4,5-dihydro-5,5-diaryl-3-isocyanate. Azoxycarboxylic acids, dichloroacetamides, α-oxime-phenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalenedicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolium carboxylic acids, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally usable salts and their agriculturally usable derivatives such as amides, esters and thioesters, provided that they have an acid group.

[0634] Examples of safener compound C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, and bisbenzyl. 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- Zolpidem (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).

[0635] Active compounds B and C of groups b1)-b15) are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Vol. 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R.R. Schmidt, Herbizide, Georg Thieme Verlag, Stuttgart, 1995; W.H. Ahrens, Herbicide Handbook, 7th ed., Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, 7th ed., Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-dichloroacetyl-1,3- Azoxyl [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.

[0636] The attribution of an active compound to its corresponding mechanism of action is based on existing knowledge. If several mechanisms of action apply to an active compound, then the substance is attributed to only one mechanism of action.

[0637] The present invention also relates to formulations comprising at least one adjuvant and at least one compound of formula (I) of the present invention.

[0638] The formulation contains an effective amount of a compound of formula (I). The term "effective amount" refers to the amount of a combination or compound of formula (I) sufficient to control unwanted plants, especially in crops (i.e., cultivated plants), without causing significant damage to the treated crop. This amount can vary over a wide range and depends on various factors such as the unwanted plant to be controlled, the crop or material being treated, climatic conditions, and the specific compound of formula (I) used.

[0639] Compounds of formula (I), their salts, amides, esters, or thioesters can be converted into formulations commonly used in pharmaceutical preparations, such as solutions, emulsions, suspensions, powders, pastes, granules, molded products, capsules, and mixtures thereof. Examples of formulation types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or granules (e.g., WP, SP, WS, DP, DS), molded products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (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, Vol. 2, 6th edition, May 2008, CropLife International.

[0640] Formulations such as Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, AgrowReports DS243, T&F Informa, London, 2005, are prepared in a known manner.

[0641] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solvents, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and binders.

[0642] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, and cyclohexanol; diols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.

[0643] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as grain flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0644] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solvents, wetting agents, penetration enhancers, protective colloids, or auxiliaries. 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.).

[0645] Suitable anionic surfactants are alkali metal, alkaline earth metal, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, as well as 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 naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamides. 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.

[0646] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated by 1-50 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 glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitol, ethoxylated sorbitol, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0647] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two 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 containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polyalkalis. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polyalkalis are polyvinylamine or polyvinylamine.

[0648] Suitable adjuvants are compounds that possess negligible pesticide activity or even no pesticide activity themselves, but which improve the biological properties of the target analyte. 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.

[0649] Suitable thickeners are polysaccharides (such as xanthan gum and carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0650] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0651] Suitable antifreeze agents include ethylene glycol, propylene glycol, urea, and glycerin.

[0652] Suitable defoamers are polysiloxanes, long-chain alcohols, and fatty acid salts.

[0653] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[0654] Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.

[0655] Examples of formulation types and their preparation are as follows:

[0656] i) Water-soluble concentrates (SL, LS)

[0657] Dissolve 10-60% 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) and 5-15% by weight of a wetting agent (e.g., an alcohol alkoxylate) in water and / or a water-soluble solvent (e.g., an alcohol) added to 100% by weight. The active substance dissolves upon dilution with water.

[0658] ii) Dispersible concentrate (DC)

[0659] Dissolve 5-25% 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) and 1-10% by weight of a dispersant (e.g., polyvinylpyrrolidone) in an organic solvent (e.g., cyclohexanone) added to 100% by weight. Dilute with water to obtain a dispersion.

[0660] iii) Emulsifiable concentrate (EC)

[0661] 15-70% by weight of a 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% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) is dissolved in a water-insoluble organic solvent (e.g., an aromatic hydrocarbon) added to 100% by weight. The emulsion is then diluted with water.

[0662] iv) Emulsions (EW, EO, ES)

[0663] 5-40% by weight of a 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% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbons). This mixture is introduced into 100% by weight of water using an emulsifier to form a homogeneous emulsion. The emulsion is diluted with water to obtain a suspension (SC, OD, FS).

[0664] In a stirred ball mill, 20-60 wt% of a 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 subjected to underwater milling with the addition of 2-10 wt% dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e.g., xanthan gum), and up to 100 wt% water to obtain a finely ground active substance suspension. The suspension is diluted with water to obtain a stable active substance suspension. For FS type formulations, up to 40 wt% binder (e.g., polyvinyl alcohol) is added. vi) Water-dispersible particles and water-soluble particles (WG, SG)

[0665] 50-80% by weight of a 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 finely milled with the addition of up to 100% by weight of a dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble granules using industrial equipment (e.g., extruder, spray tower, fluidized bed). Diluting with water yields a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0666] 50-80% by weight of a 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 milled 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). The mixture is diluted with water to obtain a stable dispersion or solution of the active substance.

[0667] viii) Gel (GW, GF)

[0668] In a stirred ball mill, 3-10 wt% of a dispersant (e.g., sodium lignin sulfonate), 1-5 wt% of a thickener (e.g., carboxymethyl cellulose), and up to 100 wt% of 5-25 wt% of a 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), are added to obtain a fine suspension of the active substance. Diluting with water yields a stable suspension of the active substance.

[0669] iv) Microemulsions (ME)

[0670] Add 5-20% 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 herbicide compound B (component B) and safener C (component C) to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and 100% by weight of water. Stir the mixture for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0671] iv) Microcapsules (CS)

[0672] An oil phase comprising 5-50 wt% of a 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), 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15 wt% 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 comprising 5-50 wt% of a compound of formula (I) of the present invention, 0-40 wt% 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). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. wt% refers to the entire CS formulation.

[0673] ix) Sprinkleable powder (DP, DS)

[0674] 1-10% by weight 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 safer agent C (component C) is finely ground and thoroughly mixed with up to 100% by weight of a solid carrier (e.g., finely ground kaolin).

[0675] x) particles (GR, FG)

[0676] 0.5-30% 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 finely ground and combined with up to 100% by weight of a solid carrier (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0677] xi) Ultra-low volume liquids (UL)

[0678] Dissolve 1-50% 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) in an organic solvent (e.g., an aromatic hydrocarbon) added to 100% by weight.

[0679] Formulation types i)-xi) may optionally contain other adjuvants, such as 0.1-1% by weight of bactericide, 5-15% by weight of antifreeze, 0.1-1% by weight of defoamer and 0.1-1% by weight of colorant.

[0680] Formulations and / or combinations typically contain 0.01-95% by weight, preferably 0.1-90% by weight, and especially 0.5-75% by weight of compound (I). Compound (I) is used with a purity of 90-100%, preferably 95-100% (based on NMR spectroscopy).

[0681] For treating plant propagation material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. These formulations, after dilution 2-10 times, provide an active ingredient concentration of 0.01-60% by weight, preferably 0.1-40% by weight, in ready-to-use formulations. (Down)

[0682] Methods of applying compounds of formula (I), their formulations, and / or combinations to plant propagation material, especially seeds, include seed dressing, coating, granulation, powdering, soaking, and furrow application. Preferably, compounds of formula (I), their formulations, and / or combinations are applied to the plant propagation material by methods that do not induce germination, such as seed dressing, granulation, coating, and powdering.

[0683] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g., herbicides, insecticides, fungicides, growth regulators, safeners) can be added as premixes or, if appropriate, immediately before use (in a barrel mix) to compounds of formula (I), formulations containing them, and / or combinations thereof. These agents can be mixed with the formulations of the present invention at a weight ratio of 1:100-100:1, preferably 1:10-10:1.

[0684] Users typically use compounds of formula (I) of the present invention, formulations comprising them, and / or combinations thereof in pre-dosing devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. The formulation is typically prepared to the desired application concentration with water, buffers, and / or other adjuvants to obtain a ready-to-use spray or a formulation of the present invention. 20-2000 liters, preferably 50-400 liters, of ready-to-use spray are typically applied per hectare of agricultural use area.

[0685] According to one embodiment, the user can mix the components of the formulation of the present invention or a portion of the premixed components, such as the components comprising the compound of formula (I) and optionally, the active substances selected from groups B and / or C), in a spray can, and other adjuvants and additives may be added if appropriate.

[0686] In another embodiment, the user can mix the components of the formulation of the present invention, such as the parts of a packaged kit or the parts of a binary or ternary mixture, in a spray can and, if appropriate, add other adjuvants.

[0687] In another embodiment, the components or partially premixed components of the formulation of the present invention may be applied in combination (e.g., after barrel mixing) or sequentially, such as components comprising the compound of formula (I) and optionally, active substances selected from groups B and / or C).

[0688] Compounds of formula (I) are suitable as herbicides. They are suitable either directly as suitable formulations or in combination with at least one other compound selected from herbicidal active compound B (component B) and safener C (component C).

[0689] Compounds of formula (I), or formulations and / or combinations thereof containing formula (I), are highly effective at controlling unwanted plants in non-crop areas, especially at high application rates. They act on broadleaf and grass weeds in crops such as wheat, rice, maize, soybean, and cotton without causing any significant damage to the crops. This effect is primarily observed at low application rates.

[0690] Compounds of formula (I) or formulations and / or combinations thereof are applied to plants primarily by foliar spraying. Application can be made using conventional spraying techniques with a volume of approximately 100-1000 l / ha (e.g., 300-400 l / ha) using, for example, water as a carrier. Compounds of formula (I) or formulations and / or combinations thereof may also be applied by low-volume or ultra-low-volume methods or in microparticle form.

[0691] The application of compounds of formula (I) or formulations and / or combinations thereof may be carried out before, during and / or after unwanted plant emergence, preferably during and / or after.

[0692] The application of the compound or formulation and / or combination of formula (I) can be carried out before or during sowing.

[0693] Compounds of Formula (I) or formulations and / or combinations thereof may be applied pre-emergence, post-emergence, or before planting, or together with crop seeds. Compounds of Formula (I) or formulations and / or combinations thereof may also be applied by pre-treating crop seeds with compounds of Formula (I) or formulations and / or combinations thereof. If the active ingredient is not well tolerated by certain crops, an application technique (post-guided, final tillage procedure) may be used in which the combination is sprayed with a spraying device to minimize contact with the leaves of sensitive crops, allowing the active ingredient to reach the leaves of unwanted plants growing underneath or the bare soil surface.

[0694] In another embodiment, the compound of formula (I) or formulations and / or combinations thereof may be applied by treating the seeds. Seed treatment generally comprises all procedures well known to those skilled in the art based on the compound of formula (I) or formulations and / or combinations thereof (seed dressing, seed coating, seed dusting, seed soaking, seed coating, multi-layer seed coating, seed hulling, seed dripping, and seed granulation). The combination may be applied diluted or undiluted.

[0695] The term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, seedlings, and similar forms. The preferred term used here describes corn and its seeds. The seeds used can be from the aforementioned crop plants, but can also be from genetically modified plants or plants obtained through conventional breeding methods.

[0696] When used in plant protection, the amount of active substance without formulation adjuvants, i.e., compound of formula (I), component B and suitable component C, is 0.001-2 kg / ha, preferably 0.005-2 kg / ha, more preferably 0.05-0.9 kg / ha, especially 0.1-0.75 kg / ha, depending on the desired effect.

[0697] In another embodiment of the invention, the application rate of the compound of formula (I), component B and suitable component C is 0.001-3 kg / ha, preferably 0.005-2.5 kg / ha, especially 0.01-2 kg / ha of active substance (as).

[0698] In another preferred embodiment of the invention, the application rate (total amount of compound (I)) of the compound of the present invention depends on the target of control, season, target plant and growth stage and is 0.1-3000 g / ha, preferably 10-1000 g / ha.

[0699] In another preferred embodiment of the 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.

[0700] In another preferred embodiment of the 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.

[0701] The required application rate of herbicide compound B is typically 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[0702] The required application rate of safety agent C is typically 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[0703] In the treatment of plant propagation materials such as seeds, for example by powdering, coating or soaking the seeds, the required amount of active material is usually 0.1-1000g, preferably 1-1000g, more preferably 1-100g, and most preferably 5-100g / 100kg of plant propagation material (preferably seeds).

[0704] In another embodiment of the invention, in order to treat the seeds, the amount of the active substance, namely the compound of formula (I), component B and suitable component C, applied is typically 0.001-10 kg / 100 kg of seeds.

[0705] When used to protect materials or store products, the amount of active substance applied depends on the type of area to be treated and the desired effect. In material protection, the typical application amount is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[0706] In the case of the combination of the present invention, it is not important whether the compound of formula (I) and other components B and / or components C are formulated and applied together or separately.

[0707] When applied separately, the order in which they are applied is less important. The only requirement is that the compound of formula (I) and other components B and / or C are applied within a timeframe that allows these active ingredients to act on the plant simultaneously, preferably within a timeframe of up to 14 days, and especially up to 7 days.

[0708] Depending on the method of application, compounds of formula (I) or formulations and / or combinations thereof may be used additionally on many other crops to eliminate unwanted plants. Suitable crop examples include: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), beet (Beta vulgaris spec.altissima), beet (Beta vulgaris spec.rapa), European rapeseed (Brassica napus var.napus), rutabaga (Brassica napus var.napobrassica), rutabaga (Brassica rapa var.silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), large-leaf tea (Camellia sinensis), safflower (Carthamus tinctorius), American pecan (Carya illinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruit coffee (Coffea arabica) (medium-fruit coffee (Coffea arabica)) The following are genera of plants: canephora, coffee (Coffealiberica), cucumber (Cucumis sativus), bermudagrass (Cynodon dactylon), carrot (Daucus carota), 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), and apple (Malus spec.).), cassava (Manihot esculenta), alfalfa (Medicagosativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (yellow-flowered tobacco (N. rustica)), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pistachio (Pistacia vera), Pisumsativum, 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 bean (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis) The following crops are listed: *Solanum tuberosum*, *Sorghum bicolor* (sorghum vulgare), *Theobromacacao*, *Trifolium pratense*, *Triticum aestivum*, *Triticale*, *Triticum durum*, broad bean (*Vicia faba*), grape (*Vitis vinifera*), and maize (*Zea mays*).

[0709] Preferred crops include peanut (Arachis hypogaea), sugar beet (Beta vulgarisspec.altissima), European rapeseed (Brassica napus var.napus), kale (Brassica oleracea), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruited coffee (Coffea arabica) (medium-fruited coffee (Coffea canephora), large-fruited coffee (Coffea liberica)), bermudagrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum) (tree cotton (Gossypium arcoreum), herb cotton (Gossypium herbaceum), Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), and tomato (Lycopersicon). lycopersicum), Malus spec., Alfalfa (Medicago sativa), Tobacco (Nicotiana tabacum) (Yellow-flowered Tobacco (N. rustica)), Olive (Olea europaea), Rice (Oryza sativa), Golden Bean (Phaseolus lunatus), Common Bean (Phaseolus vulgaris), Pistachio (Pistacia vera), Pisum sativum, Almond (Prunus dulcis), Sugarcane (Saccharum officinarum), Rye (Secale cereale), Potato (Solanum tuberosum), Bicolor Sorghum (Sorghum vulgare) (Triticale), Common Wheat (Triticumaestivum), Durum Wheat (Triticum durum), Broad Bean (Vicia faba), Grape (Vitis vinifera), and Maize (Zea mays).

[0710] The preferred crops are cereal crops, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or perennial crops.

[0711] The compounds of formula (I) of the present invention, or formulations and / or combinations thereof, can also be used in crops that have been modified by mutagenesis or genetic engineering to provide new traits to plants or to modify existing traits.

[0712] The term “crop” as used in this article also includes plants (agricultural crops) that have been modified by mutagenesis or genetic engineering to provide new traits or modify existing traits.

[0713] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but there are also targeted mutagenesis techniques to induce 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 a wide range of nucleases to achieve a targeted effect.

[0714] Genetic engineering typically uses recombinant DNA techniques, which are not easily obtained naturally through hybridization, mutagenesis, or natural recombination, to produce modifications in the plant genome. One or more genes are usually integrated into the plant genome to add or improve traits. These integrated genes are also known in the field as transgenes, and plants containing such transgenes are called transgenic plants. This plant conversion method usually produces several conversion events, which differ in the genomic location where the transgene has been integrated. Plants containing a specific transgene at a specific genomic location are often described as containing a specific "event," which is referred to by the event name. Traits that have been introduced into plants or modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[0715] Herbicide tolerance has been developed through mutagenesis and genetic engineering. Plants conferred tolerance to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those named after herbicides such as... Commercially available plant varieties. However, most herbicide tolerance traits have been developed through the use of genetic modification.

[0716] 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 isopropionate have been tested. Isoxaflutole and mesotrione develop herbicide tolerance.

[0717] Transgenic herbicides already used to provide herbicide tolerance traits include: 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, and S4-HrA; for ALS inhibitor herbicide tolerance: csr1-2; and for HPPD inhibitor herbicide tolerance: hppdPF, W336, and avhppd-03.

[0718] Transgenic maize varieties containing herbicide tolerance genes include, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, and HCEM485. 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but others are not excluded.

[0719] Transgenic soybeans containing herbicide tolerance genes include, for example, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, and GU262. W62, W98, FG72, and CV127, but others are not excluded.

[0720] Transgenic cotton events containing herbicide tolerance genes include, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40, but others are not excluded.

[0721] Transgenic Carola events containing herbicide tolerance genes include, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3, but others are not excluded.

[0722] Insect resistance is primarily developed by transferring bacterial genes encoding insecticidal proteins into plants. The most commonly used transgenes are toxin genes from the genus *Bacillus* spp. and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, cry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes, particularly those encoding protease inhibitors such as CpTI and pinII, are also transferred into other plants. Another approach uses transgenes to target and downregulate insect genes by producing double-stranded RNA in plants. An example of such a transgene is dvsnf7.

[0723] Transgenic maize events containing insecticidal protein genes or double-stranded RNA include, 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.

[0724] Genetically modified soybeans containing insecticidal protein genes include, for example, MON87701, MON87751 and DAS-81419, but others cannot be ruled out.

[0725] Transgenic cotton events containing insecticidal protein genes include, 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.

[0726] Increased yields are achieved by using, for example, the transgenic athb17 present in maize event MON87403 to increase ear biomass or by using, for example, the transgenic bbx32 present in soybean event MON87712 to increase photosynthesis.

[0727] Crops containing modified oil content have been produced using transgenic genes: 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.

[0728] Tolerance to abiotic conditions, especially drought tolerance, was improved through the use of transgenic cspB contained in the maize event MON87460 and through the use of the soybean event. The included transgenic Hahb-4 is produced.

[0729] Traits are typically combined by combining genes during conversion events or by combining different events during the breeding process. Preferred combinations of traits include herbicide tolerance to different classes of herbicides, insect tolerance to different insect species, especially tolerance to Lepidoptera and Coleoptera, herbicide tolerance combined with resistance to one or more insect species, herbicide tolerance combined with increased yield, and herbicide tolerance combined with tolerance to abiotic conditions.

[0730] Plants containing individual or stacked traits, as well as the genes and events that provide these traits, are well known in the art. For example, detailed information about mutagenic or integrated genes and corresponding events can be obtained from the websites of organizations such as the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase), as well as patent applications such as EP 3028573 and WO2017 / 011288.

[0731] The use of compounds of formula (I) of the present invention, or formulations and / or combinations thereof, on crops may result in effects specific to crops containing certain genes or events. These effects may involve changes in growth behavior or tolerance to biotic or abiotic stressors. Such effects may in particular include increased yield, increased resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral, or viroid pathogens, as well as changes in early vigor, early or delayed maturity, cold or heat tolerance, and amino acid or fatty acid profiles or contents.

[0732] In addition, this includes plants that contain altered or new amounts of components through the use of recombinant DNA technology to particularly improve the production of raw materials, such as potatoes that produce increased amounts of amylopectin (e.g., potatoes). Potatoes (BASF SE, Germany).

[0733] Furthermore, compounds of formula (I) of the present invention, or formulations and / or combinations thereof, have been found to be suitable for defoliation and / or drying of plant parts of crops such as cotton, potatoes, rapeseed, sunflower, soybean, or broad beans, 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 discovered.

[0734] As a desiccant, the compound of formula (I) is particularly suitable for drying crops such as potatoes, rapeseed, sunflowers, and soybeans, as well as the above-ground parts of cereals. This makes fully mechanized harvesting of these important crops possible.

[0735] Also of economic significance is the promotion of harvesting citrus fruits, olives, and other pome, drupe, and nut fruits of various species and varieties, which is made possible by concentrated splitting or reduced adhesion to the tree within a certain timeframe. The same mechanism, namely promoting the formation of detachment tissue between the fruit or leaf portion and the branch portion of the plant, is also necessary for the controlled defoliation of useful plants, especially cotton.

[0736] In addition, the shortened time interval between the maturity of each cotton plant leads to improved fiber quality after harvest.

[0737] A Chemical Example

[0738] Chemical bonds drawn as bars in a chemical formula represent relative stereochemistry in a ring system.

[0739] Example 1:

[0740] Synthesis of 3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionic acid (Inter A)

[0741]

[0742] Lithium hydroxide (LiOH) (3.05 g, 127 mmol) was added to diethyl 2,2-difluoromalonate (1) (25 g, 127 mmol, CAS 680-65-9) in tetrahydrofuran / water (1:1). The reaction mixture was stirred overnight at room temperature. Tetrahydrofuran was removed under reduced pressure. The resulting aqueous solution was extracted with methyl tert-butyl ether (2 × 100 mL) and the organic phase was discarded. The aqueous layer was adjusted to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate (3 × 200 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude 3-ethoxy-2,2-difluoro-3-oxo-propionic acid (2) (1.4 g, 7% yield). 1 ¹H NMR (400 MHz, acetone-d5) δ 4.18 (q, J = 7.2 Hz, 2H), 1.20 (t, J = 7.2 Hz, 3H).

[0743]

[0744] At 25 °C, 3,5-dichloroaniline (1.77 g, 11.0 mmol), a solution of 1-propanephosphonic anhydride in ethyl acetate (T3P) (50%, in DMF, 11.8 g, 18.6 mmol), and triethylamine (4.6 mL, 33 mmol) were added to a mixture of 3-ethoxy-2,2-difluoro-3-oxopropionic acid (2) (1.84 g, 11.0 mmol), and triethylamine (4.6 mL, 33 mmol) and stirred at 75 °C under N2 for 2 hours. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated, and purified by preparative HPLC (acetonitrile / water with trifluoroacetic acid) to give the desired 3-(3,5-dichloroaniline)-2,2-difluoro-3-oxopropionic acid ester (3) (540 mg, 16% yield). 1H NMR: (400MHz, CDCl3) δ 8.11 (s, 1H), 7.56 (d, J = 1.8Hz, 2H), 7.22 (s, 1H), 4.42 (q, J = 7.2Hz, 2H), 1.38 (t, J = 7.2Hz, 3H).

[0745]

[0746] Lithium hydroxide (LiOH) (69 mg, 2.9 mmol) was added to ethyl 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (3) (450 mg, 1.44 mmol) in tetrahydrofuran / water (1:1). The reaction mixture was stirred overnight at room temperature. Tetrahydrofuran was removed under reduced pressure. The resulting aqueous solution was extracted with methyl tert-butyl ether (2 × 10 mL) and the organic phase was discarded. The aqueous layer was adjusted to pH 1 using concentrated hydrochloric acid and extracted with ethyl acetate (3 × 20 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give crude 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (Inter A) (123 mg, 30% yield). LC-MS (MH): 281.8.

[0747] Example 2

[0748] Synthesis of Cpd.I.1

[0749]

[0750] Amine 1 (70 mg, 0.46 mmol, CAS 13031-60-2) was added to a solution of 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (Inter A) (100 mg, 0.352 mmol) in dimethylformamide (DMF, 5 mL). HATU (174 mg, 0.458 mmol) was added to the resulting solution, followed by diisopropylethylamine (0.18 mL, 1.1 mmol). The resulting reaction mixture was stirred overnight at room temperature. Water (5 mL) and a saturated aqueous bicarbonate solution (5 mL) were added to the reaction mixture, and the mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to obtain methyl 4-[[3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionyl]amino]butyrate (23 mg, 17%, Cpd.I.1). 1 H NMR(400MHz,THF-d8)δ10.19(s,1H),8.44(t,J=6.1Hz,1H),7.76(d,J=1.9Hz,2H),7.25(t,J= 1.9Hz, 1H), 3.59 (s, 3H), 3.30 (q, J = 6.6Hz, 2H), 2.33 (t, J = 7.3Hz, 2H), 1.82 (p, J = 7.1Hz, 2H).

[0751] Example 3:

[0752] Synthesis of Cpd.I.2

[0753]

[0754] Amine 2 (29 mg, 0.19 mmol, CAS 139243-55-3) was added to a solution of 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (49 mg, 0.17 mmol) in dimethylformamide (DMF, 2 mL). HATU (72 mg, 0.19 mmol) was added to the resulting solution, followed by diisopropylethylamine (0.15 mL, 0.86 mmol). The resulting reaction mixture was stirred overnight at room temperature. Water (2 mL) and a saturated aqueous bicarbonate solution (2 mL) were added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to obtain methyl (3S)-3-[[3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionyl]amino]butyrate (20 mg, 30%, Cpd.I.2). ¹H NMR: (400 MHz, CDCl₃) δ 8.87 (s, 1H), 7.56 (d, J = 1.8 Hz, 2H), 7.46 (d, J = 8.5 Hz, 1H), 7.18 (t, J = 1.8 Hz, 1H), 4.41 (p, J = 6.6 Hz, 1H), 3.72 (s, 3H), 2.61 (m, 2H), 1.33 (d, J = 6.8 Hz, 3H).

[0755] Example 4:

[0756] Synthesis of Cpd.I.3

[0757]

[0758] To a solution of 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (Inter A) (100 mg, 0.352 mmol) in dimethylformamide (DMF, 5 mL), methyl (1R,3S)-3-aminocyclopentanecarboxylate (3) (70 mg, 0.387 mmol) was added. HATU (147 mg, 0.387 mmol) was added to the resulting solution, followed by diisopropylethylamine (0.24 mL, 1.4 mmol). The resulting reaction mixture was stirred overnight at room temperature. Water (5 mL) and a saturated aqueous bicarbonate solution (5 mL) were added to the reaction mixture, and the mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to obtain methyl (1R)-3-[[3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionyl]amino]cyclopentanecarboxylate (3 mg, 2%, Cpd.I.3). 1 HNMR(500MHz,THF-d8)δ10.22(s,1H),8.33(m,1H),7.77(d,J=1.8Hz,2H),7.25(t,J=1.8Hz,1H),4.25(p,J=7.3Hz,1H),3 .63(s,3H),2.85(p,J=8.2Hz,1H),2.23(dt,J=13.1,7.7Hz,1H),1.93(m,3H),1.81(dt,J=13.1,8.0Hz,1H),1.68(m,1H).

[0759] Example 5:

[0760] Synthesis of Cpd 1.4

[0761]

[0762] To a solution of 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (Inter A) (100 mg, 0.352 mmol) in dimethylformamide (DMF, 5 mL), methyl (1R,4S)-3-aminocyclopentane-2,3-carboxylate (4) (70 mg, 0.387 mmol) was added. HATU (147 mg, 0.387 mmol) was added to the resulting solution, followed by diisopropylethylamine (0.24 mL, 1.4 mmol). The resulting reaction mixture was stirred overnight at room temperature. Water (5 mL) and a saturated aqueous bicarbonate solution (5 mL) were added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (3 × 10 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to obtain methyl (1R)-3-[[3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionyl]amino]cyclopentanecarboxylate (3 mg, 2%, Cpd.I.4). 1 H NMR(500MHz,THF-d8)δ10.22(s,1H),8.33(m,1H),7.77(d,J=1.8Hz,2H),7.25(t,J=1.8Hz,1H),4.25(p,J=7.3Hz,1H),3 .63(s,3H),2.85(p,J=8.2Hz,1H),2.23(dt,J=13.1,7.7Hz,1H),1.93(m,3H),1.81(dt,J=13.1,8.0Hz,1H),1.68(m,1H).

[0763] Example 6:

[0764] Synthesis of 3-(3,5-dichloroaniline)-2-fluoro-3-oxo-propionic acid (Inter B):

[0765]

[0766] Potassium hydroxide (1.57 g, 28.1 mmol) was added to a solution of diethyl 2-fluoromalonate (1) (5.0 g, 28 mmol, CAS 344-14-9) in ethanol / water (1:1, 90 mL each) at 10 °C and stirred at this temperature for 3 hours. The mixture was heated to 40 °C and stirred for 16 hours. The mixture was concentrated to give crude product 3-ethoxy-2-fluoro-3-oxo-propionic acid (2) (3.9 g, 93% yield). 1 ¹H NMR (400MHz, acetone-d5) δ 5.25 (m, 1H), 4.28 (m, 2H), 1.26 (t, J = 7.2Hz, 3H).

[0767]

[0768] At 10 °C, 3,5-dichloroaniline (1.04 g, 6.4 mmol), 1-propanephosphonic anhydride solution (T3P) (50%, in DMF, 10.2 g, 16.0 mmol), and triethylamine (2.2 g, 21 mmol) were added to a mixture of 3-ethoxy-2-fluoro-3-oxo-propionic acid (2) (1.6 g, 11.0 mmol) in ethyl acetate / dimethylformamide (DMF) (1:1, 16 mL each) and stirred at the same temperature for 3 hours. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated, and purified by column chromatography (pentane / MTBE 9:1–7:3) to give the desired 3-(3,5-dichloroanilino)-2-fluoro-3-oxo-propionic acid ester (3) (1.7 g, 53%). 1H NMR: (400MHz, DMSO-d6) δ 10.9 (s, 1H), 7.74 (d, J = 1.8Hz, 2H), 7.39 (t, J = 1.9Hz, 1H), 5.72 (m, 1H), 4.45 (q, J = 7.1Hz, 2H), 1.23 (t, J = 7.2Hz, 3H).

[0769]

[0770] Ethyl 3-(3,5-dichloroanilino)-2-fluoro-3-oxo-propionic acid (3) (1.60 g, 5.44 mmol) in ethanol (20 mL) was added to water (12 mL) containing potassium hydroxide (914 mg, 16.3 mmol). After stirring at 10 °C for 16 hours, the mixture was poured into ice water and the pH was adjusted to 6-7 using concentrated hydrochloric acid. After removing the organic layer, the aqueous solution was further adjusted to pH 2-3 using hydrochloric acid (2N) and extracted with ethyl acetate (3 × 20 mL). The combined extracts were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give crude 3-(3,5-dichloroanilino)-2-fluoro-3-oxo-propionic acid (Inter B) (123 mg, 30% yield) as a yellow solid. 1H NMR: (400MHz, DMSO-d6) δ14.12 (br s, 1H), 7.75 (d, J = 1.9Hz, 2H), 7.39 (t, J = 1.8Hz, 1H), 5.56 (m, 1H).

[0771] Example 7:

[0772] Synthesis of Cpd.I.5

[0773]

[0774] At 10 °C, amine 1 (0.67 g, 4.0 mmol), 1-propanephosphonic anhydride solution (T3P) (50%, in DMF, 3.8 g, 6.0 mmol), and triethylamine (0.81 g, 8.0 mmol) were added to a mixture of 3-(3,5-dichloroaniline)-2,2-difluoro-3-oxo-propionic acid (Inter B) (1.1 g, 4.0 mmol) in ethyl acetate / dimethylformamide (DMF) (1:1, 20 mL each) and stirred at the same temperature for 16 hours. The mixture was then poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried with sodium sulfate, concentrated, and purified by preparative HPLC (acetonitrile / water and trifluoroacetic acid) to obtain methyl (3S)-3-[[3-(3,5)-dichloroaniline)-2-fluoro-3-oxo-propionyl]amino]butyrate (430 mg, 20%, Cpd. I. 5, a 1:1 mixture of non-stereoisomers), a white solid. 1H NMR: (400MHz, DMSO-d6) δ10.66(d,J=9.7Hz,2H),8.51(br t,J=9.0Hz,2H),7.75(m,4H),7.37(s,2H),5.46(s,1H),5.35(s,1H),4.18(br s, 2H), 3.57 (s, 3H), 3.56 (s, 3H), 2.45 (m, 6H), 1.13 (d, J = 6.7Hz, 3H).

[0775] Example 8:

[0776] Synthesis of Cpd.I.7

[0777]

[0778] The reaction was carried out in five reaction vessels, each equipped with a mixture of Cpd.I.5 (1 g, 2.75 mmol) and Umemoto reagent (1) (1.1 g, 2.75 mmol, CAS: 129946-88-9) in DMF (20 mL). After adding K₂CO₃ (1.14 g, 8.25 mmol) at 15 °C, the mixture was stirred at the same temperature for 2 hours. LC-MS showed trace amounts of the desired MS (~3%). After filtration, the filtrate was poured into HCl (150 mL, 0.1 N) and extracted with EtOAc (150 mL * 2). The combined extracts were dried over anhydrous Na₂SO₄ and concentrated. Purification was achieved by silica gel column chromatography using a gradient of ethyl acetate in pentane and preparative HPLC (acetonitrile / water with trifluoroacetic acid) to give the desired compound (73.7 mg, 1.2%, Cpd.I.7) as a 1:1 mixture of diastereomers. 1H NMR: (400MHz, CDCl3) δ9.57-9.39(m,1H),7.69(br d,J=7.2Hz,1H),7.56(t,J=1.6Hz,2H),7.23-7.18(m,1H),4.44(td,J=6.5,13. 4Hz, 1H), 3.73 (d, J = 4.2Hz, 3H), 2.70-2.54 (m, 2H), 1.34 (dd, J = 4.0, 6.8Hz, 3H).

[0779] Example 9:

[0780] Synthesis of Cpd.I.8

[0781]

[0782] Amine 2 (39 mg, 0.22 mmol) was added to a mixture of 3-(3,5-dichloroanilino)-2,2-difluoro-3-oxo-propionic acid (Inter B) (45 mg, 0.17 mmol) in DMF (2 mL). HATU (88 mg, 0.22 mmol) was added to the resulting solution, followed by diisopropylethylamine (0.086 mL, 0.51 mmol). The resulting reaction mixture was stirred overnight at room temperature. Water (5 mL) and a saturated aqueous bicarbonate solution (5 mL) were added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to obtain methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-fluoro-3-oxo-propionyl]amino]cyclopent-2-ene-1-carboxylate (60 mg, 91%, Cpd.I.8). 1¹H NMR (400MHz, CDCl₃) δ (diastereomer 1) 9.42 (s, 1H), 7.52 (m, 2H), 7.41 (m, 1H), 5.92 (m, 2H), 5.36 (dd, J = 47.6, 2.9 Hz, 1H), 5.07 (m, 1H), 3.71 (s, 3H), 3.53 (m, 1H), 3.24 (p, J = 6.6 Hz, 1H), 2.46 (m, 1H), 1.99 (m, 1H). δ(diastereomer 2) 9.42(s, 1H), 7.52(m, 2H), 7.41(m, 1H), 5.92(m, 2H), 5.36(dd, J = 47.6, 2.9 Hz, 1H), 5.07(m, 1H), 3.71(s, 3H), 3.53(m, 1H), 2.70(q, J = 7.2 Hz, 1H), 2.46(m, 1H), 1.99(m, 1H).

[0783] High performance liquid chromatography: HPLC column Kinetex XB C18 1.7μm (50x2.1mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 over 1.5 min at 60 °C, flow rate gradient from 0.8 to 1.0 ml / min over 1.5 min).

[0784] Similar to the examples above, compounds of formula (I) were prepared starting from a commercially available diester and using a commercially available amine, wherein R 1 and R 8 It is hydrogen:

[0785]

[0786] Table 2

[0787] In Table 2, It refers to cyclopropyl.

[0788] HPLC / MS = mass-to-charge ratio

[0789]

[0790]

[0791]

[0792] B Application Examples

[0793] The herbicidal activity of the compound of formula (I) was demonstrated by the following greenhouse tests:

[0794] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% humus as the substrate. Seeds of test plants were sown individually for each variety.

[0795] For pre-emergence treatment, apply the active ingredient, either suspended or emulsified in water, directly after sowing using a fine-distribution nozzle. Gently irrigate the containers to promote germination and growth, then cover with a clear plastic cover until the test plants have rooted. This covering results in uniform germination of the test plants, unless this is disrupted by the active ingredient.

[0796] For post-emergence treatment, the test plants are first allowed to grow to a height of 3-15 cm, depending on the plant's habits, and only at this stage are they treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants are either directly sown and grown in the same containers, or they are first allowed to grow individually as seedlings and then transplanted into the test containers a few days before treatment.

[0797] Depending on the variety, the test plants were kept at 10-25℃ or 20-35℃.

[0798] The testing period is 2-4 weeks. During this period, the test plants are cared for and their responses to each treatment are evaluated.

[0799] Evaluation is conducted using a rating scale of 0-100. 100 indicates no plant emergence or at least complete damage to the above-ground portion, while 0 indicates no damage or normal growth. A score of 65-90 is given for good weed control activity, while a score of 90-100 is given for very good weed control activity.

[0800] The test plants used in the greenhouse experiment belong to the following varieties:

[0801]

[0802]

[0803] At an application rate of 0.250 kg / ha, apply via pre-emergence method:

[0804] Compounds I.14, I.15, and I.17 showed very good herbicidal activity against ECHCG.

[0805] Compound I.3 showed good herbicidal activity against ECHCG.

[0806] Compounds I.14 and I.17 showed very good herbicidal activity against APESV.

[0807] Compound I.16 showed good herbicidal activity against APESV.

[0808] Compound I.17 showed very good herbicidal activity against SETFA.

[0809] Compounds I.14 and I.15 showed good herbicidal activity against SETFA.

[0810] Compound I.15 showed very good herbicidal activity against AMARE.

[0811] At an application rate of 0.500 kg / ha, apply via pre-emergence method:

[0812] Compound I.2 showed good herbicidal activity against APESV.

[0813] At an application rate of 1,000 kg / ha, apply via pre-emergence method:

[0814] Compounds I.5 and I.12 showed good herbicidal activity against APESV.

[0815] Compound I.5 showed good herbicidal activity against ECHCG.

[0816] At an application rate of 0.250 kg / ha, apply via post-emergence method:

[0817] Compound I.3 showed very good herbicidal activity against ALOMY.

[0818] Compounds I.4, I.14, I.15, and I.17 showed very good herbicidal activity against AMARE.

[0819] Compound I.3 showed good herbicidal activity against ABUTH.

[0820] Compound I.15 showed very good herbicidal activity against AVEFA.

[0821] Compounds I.3 and I.16 showed good herbicidal activity against AVEFA.

[0822] Compounds I.4, I.14, I.15, I.16, and I.17 showed very good herbicidal activity against ECHCG.

[0823] Compounds I.4, I.14, I.16, and I.17 showed very good herbicidal activity against ABUTH.

[0824] At an application rate of 0.500 kg / ha, apply via post-emergence method:

[0825] Compound I.6 showed very good herbicidal activity against AMARE.

[0826] Compounds I.1 and I.2 showed good herbicidal activity against AMARE. Compound I.1 showed good herbicidal activity against AVEFA.

[0827] Compounds I.2 and I.6 showed very good herbicidal activity against ECHCG. Compounds I.1 and I.2 showed very good herbicidal activity against SETVI.

[0828] At an application rate of 1,000 kg / ha, apply via post-emergence method:

[0829] Compound I.5 showed very good herbicidal activity against ALOMY.

[0830] Compounds I.5 and I.13 showed good herbicidal activity against AMARE. Compound I.12 showed very good herbicidal activity against AVEFA.

[0831] Compound I.5 showed good herbicidal activity against AVEFA.

[0832] Compound I.12 showed very good herbicidal activity against ECHCG.

[0833] Compound I.12 showed very good herbicidal activity against SETVI.

Claims

1. Compound of formula (I): The substituents have the following meanings: R 1 hydrogen; R 2 hydrogen; R 3 Halogen, C1-C3 haloalkyl or C1-C3 haloalkoxy; R 4 Hydrogen or halogen; R 5 Hydrogen or halogen; R 6 hydrogen; R 7 Hydrogen, halogen, cyano, C1-C3 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl or C1-C3 hydroxyalkyl; R 8 hydrogen; X key; YZ, or C1-C8 alkyl, which is substituted by m groups selected from the following: CO2R e ; Z is a 5-member saturated or partially unsaturated carbon ring, substituted by m groups selected from the following: CO2R e ; R e Hydrogen or C1-C6 alkyl; m 1 or 2; This includes its agricultural salts, provided that the compound of formula (I) has a carboxyl group.

2. The compound according to claim 1, wherein the substituents have the following meanings: R 3 halogen; R 5 Hydrogen or halogen.

3. The compound according to claim 1 or 2, wherein the substituent has the following meaning: R 4 hydrogen.

4. The compound according to claim 1 or 2, wherein the substituent has the following meaning: R 7 Hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 hydroxyalkyl.

5. The compound according to claim 1 or 2, Where R e It is a C1-C6 alkyl group.

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

7. The composition of claim 6, wherein it comprises other herbicides.

8. Use of a compound according to any one of claims 1-5 or a composition according to claim 6 or 7 in the control of unwanted plants.

9. A method for controlling unwanted plants, comprising applying a herbicidal active amount of at least one compound according to any one of claims 1-5 or a composition according to claim 6 or 7 to a plant, its seeds or its growing ground.

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