Herbicidal malonamide and malonamide esters

Abstract

The present invention relates to the use of malonic monoamides and malonamide esters of formula (I) wherein the variables are as defined in the claims and the description for controlling unwanted vegetation, to a method for combating unwanted vegetation by using such compounds, to compositions comprising such compounds and to certain malonic acid monoamides and malonamide esters of formula (I). # imgabs0 #

Description

[0001] The present invention relates to the use of malonamides and malonamide esters of formula (I) as defined below for controlling unwanted vegetation, to methods for combating unwanted vegetation by using such compounds, to compositions comprising such compounds and to certain malonamides and malonamide esters of formula (I). Background Art

[0002] For controlling unwanted vegetation, especially in crops, there is a continuing need for new herbicides which have high activity and selectivity and are substantially non-toxic to humans and animals.

[0003] WO 2012 / 130798, WO 2014 / 04882, WO 2014 / 048882, WO 2018 / 228985, WO 2018 / 228986, WO 2019 / 034602, WO 2019 / 145245, WO 2020 / 114932, WO 2020 / 114934 and WO 2020 / 182723 describe 3-phenylisoxazoline-5-carboxamide and its use as herbicide.

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

[0005] Malonic acid derivatives are also described as plant growth regulators in US 3,072,473.

[0006] WO 01 / 12183 describes the use of malonic acid derivatives for the treatment of cell adhesion-mediated pathologies, which malonic acid derivatives are characterized by a monocyclic saturated heterocycle having up to two heteroatoms.

[0007] WO 2022 / 112351 relates to malonate diamides and their use as herbicides. Certain malonate monoamides and malonate esters are used as intermediates for the synthesis of target malonate diamides; however, they are not used for any other purpose, and in particular not as herbicides.

[0008] The compounds of the prior art often have insufficient herbicidal activity, especially at low application rates, and / or unsatisfactory selectivity, resulting in low compatibility with crop plants.

[0009] WO 2013 / 032797 relates to oxetane 3,3-dicarboxamides which modulate protein kinase signal transduction pathways, thereby making them useful as anticancer agents and for treating other diseases associated with said pathways. In the synthesis of one of said diamides, in Example 1B, 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid is prepared as an intermediate compound and further transformed.

[0010] US 5,123,951 relates to plant growth regulator compositions containing ethylene (type) response inducers and malonic acid derivative compounds. In Table 3, 2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester is listed as a representative of such malonic acid derivatives, among many other items. However, neither the synthesis of this compound nor its use or any combination with ethylene (type) response inducers is disclosed.

[0011] It was therefore an object of the present invention to provide further malonamide compounds which have strong herbicidal activity, in particular even at low application rates, sufficiently low toxicity to humans and animals and / or high compatibility with crop plants. The malonamide compounds should also exhibit a broad spectrum of activity against a large number of different unwanted plants.

[0012] These and further objects are achieved by the compounds of formula (I) as defined below, including agriculturally acceptable salts, stereoisomers and tautomers thereof. Summary of the invention

[0013] The present invention therefore relates to the use of a compound of formula (I), an agriculturally acceptable salt, a stereoisomer or a tautomer thereof for combating undesirable vegetation,

[0014]

[0015] in

[0016] R 1 is hydrogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0017] R 2 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0018] R 3is hydrogen, halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl;

[0019] R 4 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)-halocycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0020] R 5 is hydrogen, halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl;

[0021] R 6 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0022] R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5-, 6-, 7- or 8-membered monocyclic or bicyclic heterocyclic ring W which, in addition to this carbon atom, contains q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, one of the carbon ring atoms carries p oxo groups, and wherein the ring is surrounded by n radicals R b replace;

[0023] R 9is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or phenyl-(C1-C3)-alkyl,

[0024] wherein the last six groups are each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members;

[0025] R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy;

[0026] Each R b R is independently halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl; or two R bonded to the same carbon atom b Together they form a methylene group (=CH2);

[0027] Each m is independently 0, 1, 2, 3, 4 or 5;

[0028] Each n is independently 0, 1 or 2;

[0029] p is 0 or 1;

[0030] q is 1, 2, 3, 4, 5, or 6;

[0031] u is 0, 1, or 2;

[0032] v is 0, 1, 2, or 3;

[0033] w is 0, 1, or 2;

[0034] The premise is that at least one of u, v and w is not 0.

[0035] In a particular embodiment, the use according to the invention does not encompass the use of ethyl 2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylate.

[0036] In addition, the present invention relates to a herbicidal composition, which comprises at least one compound with formula (I) as defined above, its agriculturally acceptable salt, its stereoisomer or its tautomer, and at least one adjuvant commonly used in the preparation of crop protection compounds. In a specific embodiment, the composition according to the present invention does not cover the composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid as a compound with formula (I) and one or more of the following solvents: acetonitrile, ethyl acetate, water, methanol, tetrahydrofuran. More particularly, the composition according to the present invention does not cover the composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid (as compound (I)), and does not cover the composition comprising 2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester (as compound (I)).

[0037] In another specific embodiment, the composition according to the present invention does not encompass such compounds, which simultaneously contain one of the following compounds:

[0038] Compound (I), wherein

[0039] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), 2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-O-), 3,5-dimethyl-2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -C(CH3)=CH-CH(CH3)-O-), oxathiolane-2,2-diyl (ie, R 7and R 8 Together, they form a bridging group -S-CH2-CH2-O-), 1,3-dioxolane-5,5-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-O-CH2-O-), 3-methyl-4,5-dihydroisoxazole-5,5-diyl (ie, R 7 and R 8 together to form a bridging group -CH2-C(CH3)=NO-), or

[0040] And R 9 is hydrogen or ethyl;

[0041] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-) or 2,5-dihydrothiophene-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-S-), and R 9 is hydrogen or methyl;

[0042] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It's F, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), and R 9 is hydrogen or ethyl;

[0043] and one or more of the following solvents: N,N-dimethylformamide, acetonitrile, ethyl acetate, water, methanol, ethanol, tetrahydrofuran, methyl tert-butyl ether, toluene, pentane, and dichloromethane.

[0044] Furthermore, the present invention relates to a composition comprising at least one compound of formula (I) as defined above (component A), an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof, and at least one further compound selected from a herbicidal compound B different from compound (I) (component B) and a safener C (component C), preferably selected from herbicidal compounds B.

[0045] The present invention also relates to a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound of formula (I), its agriculturally acceptable salt, its stereoisomer or its tautomer or said composition to act on plants, their seeds and / or their habitat.

[0046] Furthermore, the present invention relates to compound (I), its agriculturally acceptable salt, its stereoisomer and its tautomer, in addition to compound (I), wherein:

[0047] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), 2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-O-), 3,5-dimethyl-2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -C(CH3)=CH-CH(CH3)-O-), oxathiolane-2,2-diyl (ie, R 7 and R 8 Together, they form a bridging group -S-CH2-CH2-O-), 1,3-dioxolane-5,5-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-O-CH2-O-), 3-methyl-4,5-dihydroisoxazole-5,5-diyl (ie, R 7 and R 8 together to form a bridging group -CH2-C(CH3)=NO-), or

[0048] And R 9 is hydrogen or ethyl;

[0049] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form 1-tert-butoxycarbonyl-pyrrolidine-2,2-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-CH2-CH2-N(-C(O)-OC(CH3)3)-), and R 9 It is ethyl;

[0050] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 is Cl or F, R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-) or 2,5-dihydrothiophene-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-S-), and R 9 is hydrogen or methyl;

[0051] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It's F, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), and R 9 is hydrogen or ethyl;

[0052] -R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-), and R9 is tert-butyl;

[0053] -R 1 is hydrogen or methyl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-3,3-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-O-CH2-), and R 9 is hydrogen or methyl; and

[0054] -R 7 and R 8 Together with the carbon atoms to which they are bonded, they form tetrahydropyran-4,4-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-CH2-CH2), and R 9 is hydrogen or ethyl;

[0055] And in addition to the following compound (I):

[0056] -2-[(3-fluoro-5-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0057] -2-[(3-bromophenyl)carbamoyl]oxolane-2-carboxylic acid;

[0058] -2-[(4-tert-butylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0059] -2-[(2,3-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0060] -2-[(3-bromo-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0061] -2-[(5-chloro-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0062] -2-[(4-trifluoromethoxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0063] -2-[(4-ethyl-3-fluorophenyl)carbamoyl]oxolane-2-carboxylic acid;

[0064] -2-[(3,5-difluoro-4-methoxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0065] -2-[(3-chloro-4-(2-methylpropyloxy)phenyl)carbamoyl]oxolane-2-carboxylic acid;

[0066] -2-[(4-hydroxy-2-methyl-5-(1-methylethyl)phenyl)carbamoyl]oxolane-2-carboxylic acid;

[0067] -2-[(4-hydroxy-2,3,5-trimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0068] -2-[(3-hydroxy-2,4-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0069] -2-[(5-ethyl-2-hydroxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0070] -3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid as the compound having formula (I); and

[0071] -2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester. DETAILED DESCRIPTION

[0072] definition

[0073] Depending on the type of substituent, compounds with formula (I) may have one or more stereocenters, in which case they may exist as mixtures of enantiomers or diastereomers, and may also exist in the form of pure enantiomers or pure diastereomers. The invention provides pure enantiomers or pure diastereomers and mixtures thereof of compounds with formula I, and uses according to the invention of pure enantiomers or pure diastereomers or mixtures thereof of compounds with formula I. Suitable compounds with formula I also include all possible geometric stereoisomers (cis / trans or Z / E isomers) and mixtures thereof as diastereomers of a particular form. Cis / trans (Z / E) isomers may exist with respect to olefins, carbon-nitrogen double bonds, nitrogen-sulfur double bonds, amide groups or cyclic non-aromatic moieties. The term "stereoisomer" encompasses optical isomers such as enantiomers or diastereomers (the latter due to the presence of more than one stereogenic center in a molecule) as well as geometric isomers (cis / trans (Z / E) isomers). By way of example only, a stereogenic center in compound (I) is a 7 and R 8 C atoms, provided that the ring formed by these groups and the carbon atoms to which they are bonded does not have a mirror axis of rotation.

[0074] If the above-mentioned herbicidal compounds B and / or safeners C have one or more stereocenters or can exist in different geometric stereoisomers (cis / trans or E / Z isomers), they can also exist as enantiomers or diastereomers or geometric stereoisomers, and pure enantiomers or diastereomers or geometric stereoisomers or mixtures of different enantiomers, diastereomers and / or geometric stereoisomers can be used.

[0075] If the compounds of formula (I), the herbicidal compounds B and / or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are generally salts of those cations and acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compound. By way of example only, if R 9 is hydrogen or if the compound contains the substituent -CO2R a , where R a is hydrogen, then the ionizable functional group is -C(O)OH, which may be present in compound (I). Compound (I) containing such a -C(O)OH group may be in the form of its salt, i.e., in the form of a compound containing one or more groups -C(O)OH. - M + The compound is used in the form of + is a cation equivalent. Examples of agriculturally suitable cations are given below.

[0076] Preferred cations are ions of alkali metals, preferably ions of lithium, sodium and potassium, ions of alkaline earth metals, preferably ions of calcium and magnesium, and ions of transition metals, preferably ions of manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tri(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, ammonium (diethanolamine salt), tris(2-hydroxyethyl)ammonium (triethanolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally salts of polyamines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0077] Useful anions of the acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0078] Compound (I) may exist in different tautomeric forms. For example, the amide moiety -N(H)-C(=O)- may be in equilibrium with its tautomeric form -N=C(OH)-.

[0079] If, for example, R 1 is hydrogen, the malonamide moiety can be -N(H)-C(=O)-C(R 7 )(R 8 )-C(=O)-OR 9 - or as -N=C(OH)-C(R 7 )(R 8 )-C(=O)-OR 9 -exist.

[0080] The same applies if ring W is a lactam, i.e. if it contains an amide group as a ring member (= an unsubstituted secondary nitrogen ring atom adjacent to a carbon ring atom carrying an oxo group); in this case, this ring moiety -N(H)-C(=O)- can be in equilibrium with its tautomeric form -N=C(OH)-.

[0081] The amount in which one or the other tautomeric form is present depends on the entire molecular structure and even more strongly on the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature, etc.).

[0082] The term "unwanted vegetation" ("weeds") is understood to include any vegetation growing in non-crop areas or in the location of crop plants or sowing and other desired crops, wherein the vegetation is any plant species other than the sown or desired crop (if any), including its germinating seeds, emerging seedlings and established vegetation. Weeds in the broadest sense are plants that are considered undesirable in a particular location.

[0083] The terms used in the definitions of the variables for organic radicals, like the expression "halogen", are collective terms representing the individual members of these groups of organic units.

[0084] Prefix C x -C y Indicates the possible number of carbon atoms in a particular case. All hydrocarbon chains may be straight or branched.

[0085] The term "halogen" denotes in each case fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

[0086] The term "partially or fully halogenated" means that one or more, for example one, two, three, four or five or all hydrogen atoms of a given group have been replaced by halogen atoms, in particular fluorine or chlorine. Partially or fully halogenated groups are also referred to below as "halo groups". For example, partially or fully halogenated alkyl groups are also referred to as haloalkyl groups.

[0087] The term "alkyl" as used herein (and in the alkyl moieties of other groups containing alkyl, such as alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, hydroxyalkyl and alkoxyalkyl)) indicates in each case a straight-chain or branched alkyl group, which generally has from 1 to 6 carbon atoms (=C1-C6-alkyl), in particular from 1 to 4 carbon atoms (=C1-C4-alkyl) and especially from 1 to 3 carbon atoms (=C1-C3-alkyl) or 1 or 2 carbon atoms (=C1-C2-alkyl). C1-C2-alkyl is methyl or ethyl. C1-C3-alkyl is methyl, ethyl, n-propyl or isopropyl. Examples of C1-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (=sec-butyl), isobutyl and tert-butyl. Examples of C1-C6-alkyl radicals, in addition to those mentioned for C1-C4-alkyl, are n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.

[0088] The term "haloalkyl" as used herein (and in the haloalkyl moiety of other groups comprising haloalkyl, such as haloalkoxy) (which is also indicated as "partially or fully halogenated alkyl") indicates in each case a straight-chain or branched alkyl group as defined above, which generally has from 1 to 3 carbon atoms (=C1-C3-haloalkyl), for example 1 or 2 carbon atoms (=C1-C2-haloalkyl), wherein the hydrogen atoms of this group are partially or fully replaced by halogen atoms. Preferred haloalkyl moieties are fluorinated alkyl groups, such as fluorinated C1-C2-alkyl or fluorinated C1-C3-alkyl. Examples of C1-C2-haloalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, etc. Examples of C1-C3-haloalkyl are, in addition to those mentioned for C1-C2-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, etc.

[0089] The term "hydroxyalkyl" in each case denotes a straight-chain or branched alkyl group as defined above, which generally has from 1 to 3 carbon atoms (=C1-C3-hydroxyalkyl), in which one of the hydrogen atoms of this group is replaced by a hydroxy group. Examples are hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-2-propyl, etc.

[0090] The term "alkenyl" as used herein denotes in each case a monounsaturated, straight-chain or branched hydrocarbon radical, which generally has 2 to 4 carbon atoms (=C2-C4-alkenyl) or 2 or 3 carbon atoms (=C2-C3-alkenyl) and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl; C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl.

[0091] The term "haloalkenyl" (which may also be expressed as "alkenyl substituted by halogen") as used herein and the haloalkenyl portion in haloalkenyloxy etc. refer to an unsaturated straight or branched hydrocarbon group having 2 to 4 (=C2-C4-haloalkenyl) or 2 to 3 (=C2-C3-haloalkenyl) carbon atoms and double bonds at any position, wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example vinyl chloride, chloroallyl etc.

[0092] The term "alkynyl" as used herein indicates an unsaturated straight or branched hydrocarbon group, which generally has 2 to 4 carbon atoms (=C2-C4-alkynyl) or 2 to 3 carbon atoms (=C2-C3-alkynyl) and a triple bond at any position, for example C2-C3-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C2-C4-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc.

[0093] The term "haloalkynyl" as used herein (also indicated as "halogen-substituted alkynyl") refers to unsaturated straight-chain or branched hydrocarbon radicals, which generally have 2 to 4 carbon atoms (= C2-C4-haloalkynyl) or 2 or 3 carbon atoms (= C2-C3-haloalkynyl) and a triple bond (as mentioned above) in any position, wherein some or all of the hydrogen atoms in these radicals are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

[0094] The term "cycloalkyl" as used herein indicates in each case a monocyclic or bicyclic saturated alicyclic group, which generally has from 3 to 6 carbon atoms (=C3-C6-cycloalkyl), 3 to 5 carbon atoms (=C3-C5-cycloalkyl) or 3 to 4 carbon atoms (=C3-C4-cycloalkyl) as (only) ring members. Examples of monocyclic saturated alicyclic groups with 3 or 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic saturated alicyclic groups with 3 to 5 carbon atoms include cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic saturated alicyclic groups with 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of bicyclic groups with 5 or 6 carbon atoms include bicyclo[1.1.1]pentyl and bicyclo[2.1.1]hexyl. Preferably, the cycloalkyl group is monocyclic.

[0095] The term "halocycloalkyl" as used herein (and in the halocycloalkyl part of other groups comprising a halocycloalkyl group) indicates in each case a monocyclic or bicyclic alicyclic radical having generally from 3 to 6 carbon atoms ("C3-C6-halocycloalkyl"), preferably 3 to 5 carbon atoms ("C3-C5-halocycloalkyl") or 3 to 4 carbon atoms ("C3-C4-halocycloalkyl"), in which at least one (e.g. 1, 2, 3, 4 or 5) of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 1-, 2- and 3-fluorocyclobutyl, 1,2-, 1,3-, 2,2-, 2,3-, 2,4-, 3 ,3-difluorocyclobutyl, 1-, 2- and 3-chlorocyclobutyl, 1,2-, 1,3-, 2,2-, 2,3-, 2,4-, 3,3-dichlorocyclobutyl, 1-, 2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl, and the like.

[0096] The term "hydroxycycloalkyl" denotes in each case a monocyclic or bicyclic alicyclic radical which generally has from 3 to 6 carbon atoms ("hydroxy-(C3-C6)-cycloalkyl"), preferably 3 to 5 carbon atoms ("hydroxy-(C3-C5)-cycloalkyl") or 3 to 4 carbon atoms ("hydroxy-(C3-C4)-cycloalkyl"), in which at least one (e.g. 1, 2, 3, 4 or 5) hydrogen atoms are replaced by a hydroxy group. Examples are 1-hydroxycyclopropyl, 2-hydroxycyclopropyl, 1,2-dihydroxycyclopropyl, 2,3-dihydroxycyclopropyl, 1-hydroxycyclobutyl, 2-hydroxycyclobutyl, 3-hydroxycyclobutyl, 1,2-dihydroxycyclobutyl, 1,3-dihydroxycyclobutyl, 2,3-dihydroxycyclobutyl, 1-hydroxycyclopentyl, 2-hydroxycyclopentyl, 3-hydroxycyclopentyl, 1,2-dihydroxycyclopentyl, 1,3-dihydroxycyclopentyl, 2,3-dihydroxycyclopentyl and the like.

[0097] The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group, which generally has from 1 to 3 carbon atoms (=C1-C3-alkoxy), in particular 1 or 2 carbon atoms (=C1-C2-alkoxy), which is bonded to the remainder of the molecule via an oxygen atom. C1-C2-alkoxy is methoxy or ethoxy. C1-C3-alkoxy is furthermore, for example, n-propoxy or 1-methylethoxy (isopropoxy).

[0098] The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group as defined above, generally having from 1 to 3 carbon atoms (= C1-C3-haloalkoxy), in particular 1 or 2 carbon atoms (= C1-C2-haloalkoxy), wherein the hydrogen atoms of this group are partially or completely replaced by halogen atoms, in particular fluorine atoms (in this case the group is also referred to as fluorinated alkoxy). C1-C2-haloalkoxy is, for example, 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 or OC2F5. C1-C3-Haloalkoxy is furthermore, for example, 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 or 1-(CH2Br)-2-bromoethoxy.

[0099] The term "alkylthio" (also called alkylsulfanyl or "alkyl-S") as used herein indicates in each case a straight-chain or branched saturated alkyl group as defined above, which generally contains 1 to 3 carbon atoms (=C1-C3-alkylthio) or 1 to 2 carbon atoms (=C1-C2-alkylthio), which is attached via a sulfur atom in any position of the alkyl group. C1-C2-Alkylthio is methylthio or ethylthio. C1-C3-Alkylthio is additionally, for example, n-propylthio or 1-methylethylthio (isopropylthio).

[0100] The term "alkylsulfinyl" indicates an alkyl group as defined above attached via a sulfinyl [S(O)]. For example, the term "C1-C2-alkylsulfinyl" refers to a C1-C2-alkyl group as defined above attached via a sulfinyl [S(O)]. The term "C1-C3-alkylsulfinyl" refers to a C1-C3-alkyl group as defined above attached via a sulfinyl [S(O)]. C1-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C3-alkylsulfinyl is additionally, for example, n-propylsulfinyl or 1-methylethylsulfinyl (isopropylsulfinyl).

[0101] The term "alkylsulfonyl" indicates an alkyl group as defined above attached via a sulfonyl [S(O)2]. The term "C1-C2-alkylsulfonyl" refers to a C1-C2-alkyl group as defined above attached via a sulfonyl [S(O)2]. The term "C1-C3-alkylsulfonyl" refers to a C1-C3-alkyl group as defined above attached via a sulfonyl [S(O)2]. C1-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C3-alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1-methylethylsulfonyl (isopropylsulfonyl).

[0102] The substituent "oxo" replaces a CH2 group with a C(=O) group.

[0103] The suffix "-carbonyl" in a group indicates in each case that the group is bonded to the remainder of the molecule via a carbonyl C=0 group. This is the case, for example, with alkoxycarbonyl.

[0104] The term "alkoxycarbonyl" indicates an alkoxy group as defined above attached to the rest of the molecule via a carbonyl [C(=O)]. C1-C3-alkoxycarbonyl is a C1-C3-alkoxy group as defined above attached to the rest of the molecule via a carbonyl [C(=O)]. Examples of C1-C3-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl.

[0105] Thiophenyl is a benzene ring attached to the rest of the molecule via the S atom.

[0106] Phenylsulfenyl is a benzene ring attached to the rest of the molecule via an S(O) group.

[0107] A phenylsulfonyl group is a benzene ring attached to the rest of the molecule via a S(O)2 group.

[0108] Phenyl-C1-C2-alkyl is a C1-C2-alkyl as defined above, in which one of the hydrogen atoms is replaced by a phenyl ring (i.e. attached to the rest of the molecule via the alkyl). Examples are benzyl, 1-phenylethyl and 2-phenylethyl. Phenyl-C1-C3-alkyl is a C1-C3-alkyl as defined above, in which one of the hydrogen atoms is replaced by a phenyl ring (i.e. attached to the rest of the molecule via the alkyl). Examples are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl or 2-phenyl-2-propyl.

[0109] If two R bonded to the same carbon atom b Together they form a methylene group (=CH2), which means that a carbon atom which is a ring member of ring W (-CH2-) is replaced by a carbon atom which carries an exocyclic methylene group (-C(=CH2)-).

[0110] The 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members contains 1 O, S or N as ring member, or 2 or 3 N atoms as ring members, or 1 O and 1 or 2 N atoms as ring members, or 1 S and 1 or 2 N as ring members. Examples are 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-triazol-3 -yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,5-oxadiazol-3-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

[0111] R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5-, 6-, 7- or 8-membered monocyclic or bicyclic heterocyclic ring W which, in addition to this carbon atom, contains q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, one of the carbon ring atoms carries p oxo groups, and wherein the ring is surrounded by n radicals R b Substitution. n groups R b Bonding may be to both carbon ring atoms and nitrogen ring atoms (if present and if not part of a double bond in the ring).

[0112] Examples of saturated four- to eight-membered monocyclic heterocycles W are azetidine-2,2-diyl, azetidine-3,3-diyl, oxetane-2,2-diyl, oxetane-3,3-diyl, thietane-2,2-diyl, thietane-3,3-diyl, 1-oxo-thietane-2,2-diyl, 1-oxo- ... ,3-diyl, 1,1-dioxo-thietane-2,2-diyl, 1,1-dioxothietane-3,3-diyl, pyrrolidine-2,2-diyl, pyrrolidine-3,3-diyl, tetrahydrofuran-2,2-diyl, tetrahydrofuran-3,3-diyl, tetrahydrothiophene-2,2-diyl, tetrahydrothiophene-3,3-diyl, 1-oxo-tetrahydro Thiophene-2,2-diyl, 1-oxotetrahydrothiophene-3,3-diyl, 1,1-dioxo-tetrahydrothiophene-2,2-diyl, 1,1-dioxotetrahydrothiophene-3,3-diyl, pyrazolidine-3,3-diyl, pyrazolidine-4,4-diyl, imidazolidine-2,2-diyl, imidazolidine-4,4-diyl, 1,3-dioxolane-2,2-diyl , 1,3-dioxolane-4,4-diyl, 1,3-dithiolane-2,2-diyl, 1,3-dithiolane-4,4-diyl, 1,3-oxathiolane-2,2-diyl, 1,3-oxathiolane-4,4-diyl, 1,3-oxathiolane-5,5-diyl, oxazolidine-2,2-diyl, oxazolidine-4,4-diyl, Oxazolidine-5,5-diyl, isoxazolidine-3,3-diyl, isoxazolidine-4,4-diyl, isoxazolidine-5,5-diyl, thiazolidine-2,2-diyl, thiazolidine-4,4-diyl, thiazolidine-5,5-diyl, isothiazolidine-3,3-diyl, isothiazolidine-4,4-diyl, isothiazolidine-5,5-diyl, 1,2,4-oxadiazole 1,2,4-oxadiazolidine-5,5-diyl, 1,2,4-thiadiazolidine-3,3-diyl, 1,2,4-thiadiazolidine-5,5-diyl, 1,3,4-oxadiazolidine-2,2-diyl, 1,3,4-thiadiazolidine-2,2-diyl, 1,2,4-triazolidine-3,3 ... oxazolidine-5,5-diyl, tetrahydropyran-2,2-diyl, tetrahydropyran-3,3-diyl, tetrahydropyran-4,4-diyl, tetrahydrothiopyran-2,2-diyl, tetrahydrothiopyran-3,3-diyl, tetrahydrothiopyran-4,4-diyl, 1-oxotetrahydrothiopyran-2,2-diyl, 1-oxotetrahydrothiopyran-3,3-diyl, 1-oxotetrahydrothiopyran-4,4-diyl ,4-diyl, 1,1-dioxotetrahydrothiopyran-2,2-diyl, 1,1-dioxotetrahydrothiopyran-3,3-diyl, 1,1-dioxotetrahydrothiopyran-4,4-diyl, piperidine-2,2-diyl, piperidine-3,3-diyl, piperidine-4,4-diyl, 1,3-dioxane-2,2-diyl, 1,3-dioxane-4,4-diyl, 1,3-Dioxane-5,5-diyl, 1,4-dioxane-2,2-diyl, piperazine-2,2-diyl, hexahydropyridazine-3,3-diyl, hexahydropyridazine-4,4-diyl, hexahydropyrimidine-2,2-diyl, hexahydropyrimidine-4,4-diyl, hexahydropyrimidine-5,5-diyl, morpholine-2,2-diyl, morpholine-3,3-diyl, thiomorpholine-2,2-diyl, thiomorpholine-3,3-diyl 3-diyl, 1-oxo-thiomorpholine-2,2-diyl, 1-oxo-thiomorpholine-3,3-diyl, 1,1-dioxo-thiomorpholine-2,2-diyl, 1,1-dioxo-thiomorpholine-3,3-diyl, azepane-2,2-, -3,3- or -4,4-diyl, oxepane-2,2-, -3,3- or -4,4-diyl, hexahydro-1,3-diazo hexahydro-1,4-diazepine-2,2-, -4,4-, -5,5-, -6,6-, -7,7-diyl, hexahydro-1,4-oxazepine-2,2-, -3,3-, -4,4-, -5,5-, -6,6-, -7,7-diyl , hexahydro-1,3-dioxepane-2,2-, -4,4- or -5,5-diyl, hexahydro-1,4-dioxepane-2,2-, -5,5- or -6,6-diyl, oxocane-2,2-, 3,3- or -4,4-diyl, thioocane-2,2-, 3,3- or -4,4-diyl, azoocane-2,2-, 3,3- or -4,4-diyl, etc. ,

[0113] Examples of partially unsaturated four- to eight-membered monocyclic heterocycles W are 2,3-dihydrofuran-2,2-diyl, 2,3-dihydrofuran-3,3-diyl, 2,5-dihydrofuran-2,2-diyl, 2,3-dihydrothiophene-2,2-diyl, 2,3-dihydrothiophene-3,3-diyl, 2,5-dihydrothiophene-2,2-diyl, 1-oxo-2,3 -dihydrothiophene-2,2-diyl, 1-oxo-2,3-dihydrothiophene-3,3-diyl, 1-oxo-2,5-dihydrothiophene-2,2-diyl, 1,1-dioxo-2,3-dihydrothiophene-2,2-diyl, 1,1-dioxo-2,3-dihydrothiophene-3,3-diyl, 1,1-dioxo-2,5-dihydrothiophene-2,2-diyl 2,3-dihydro-1H-pyrrole-2,2-diyl, 2,3-dihydro-1H-pyrrole-3,3-diyl, 2,5-dihydro-1H-pyrrole-2,2-diyl, 1,3-dioxole-2,2-diyl, 1,3-dioxole-4,4-diyl, 1,3-dithiole-2,2-diyl, 1,3-dithiole Heterocyclopentene-4,4-diyl, 1,3-oxathiole-2,2-diyl, 1,3-oxathiole-4,4-diyl, 1,3-oxathiole-5,5-diyl, 2,3-dihydro-1H-pyrazole-3,3-diyl, 2,5-dihydro-1H-imidazole-2,2-diyl, 2,5-dihydro-1H-imidazole-5,5-diyl , 2,3-dihydrooxazole-2,2-diyl, 2,5-dihydrooxazole-2,2-diyl, 2,5-dihydrooxazole-5,5-diyl, 4,5-dihydrooxazole-4,4-diyl, 4,5-dihydrooxazole-5,5-diyl, 2,3-dihydroisoxazole-3,3-diyl, 2,5-dihydroisoxazole-2,2-diyl, 4,5-dihydroisoxazole -4,4-diyl, 4,5-dihydroisoxazole-5,5-diyl, 2,3-dihydrothiazolidine-2,2-diyl, 2,5-dihydrothiazolidine-2,2-diyl, 2,5-dihydrothiazolidine-5,5-diyl, 4,5-dihydrothiazolidine-4,4-diyl, 4,5-dihydrothiazolidine-5,5-diyl, 2,3-dihydroisothiazolidine-3,3-diyl, 2,5 -dihydroisothiazol-2,2-diyl, 4,5-dihydroisothiazol-4,4-diyl, 4,5-dihydroisothiazol-5,5-diyl, 3,6-dihydro-2H-pyran-2,2-diyl, 3,6-dihydro-2H-pyran-3,3-diyl, 3,6-dihydro-2H-pyran-6,6-diyl, 3,4-dihydro-2H-pyran-4,4- diyl, 3,4-dihydro-2H-pyran-5,5-diyl, 3,4-dihydro-2H-pyran-6,6-diyl, 3,6-dihydro-2H-thiopyran-2,2-diyl, 3,6-dihydro-2H-thiopyran-3,3-diyl, 3,6-dihydro-2H-thiopyran-6,6-diyl, 3,4-dihydro-2H-thiopyran-4,4-diyl, 3,4-dihydro-2H-thiopyran-5,5-diyl, 3,4-dihydro-2H-thiopyran-6,6-diyl, 1,2,3,4-tetrahydropyridine-2,2-diyl, 1,2,3,4-tetrahydropyridine-3,3-diyl, 1,2,3,4-tetrahydropyridine-4,4-diyl, 1,2,3,6-tetrahydropyridine-2,2-diyl, 1,2,3,6-tetrahydropyridine-3,3-diyl, 1,2,3,6-tetrahydropyridine-6,6-diyl, 1,2-dihydropyridine-2,2-diyl, 1,4-dihydropyridine-4,4-diyl, etc.

[0114] Bicyclic W contains two rings, which have at least one common ring atom. The term includes thick (fused) ring systems, in which the two rings have two common adjacent ring atoms, and spiro ring systems, in which these rings have only one common ring atom, and bridged systems with at least three common ring atoms. Bicyclic is a heterocycle, containing at least one heteroatom or heteroatom group selected from N, O and S as a ring member. Bicyclic W usually has 5 to 8 ring members.

[0115] Examples of saturated 5- to 8-membered bicyclic fused heterocycles are:

[0116]

[0117] Examples of saturated 5- to 8-membered bicyclic spiro heterocycles are:

[0118]

[0119]

[0120] Examples of saturated 5- to 8-membered bicyclic bridged heterocycles are:

[0121]

[0122] Examples of partially unsaturated 5- to 8-membered bicyclic bridged heterocycles are:

[0123]

[0124] In the above structure, # indicates the attachment point of ring W to the two C (O) groups. The attachment point is not limited to being on the ring shown, but can be on either of the two rings. Since W is attached to two carbon atoms, the attachment point is on the carbon atom shown as CH2 in the above structure. If the ring carries one or more substituents, these substituents can be bonded to carbon and / or nitrogen ring atoms.

[0125] The preferred embodiments of the invention mentioned below are to be understood as being preferred independently of one another or in combination with one another. The descriptions of the variables of compound (I) apply both to its use, to its method of use, to the compositions containing them and to compound (I) itself, unless these variables are more specifically defined (especially with respect to R 9 or R b ).

[0126] R 1 Preferred is hydrogen or (C1-C3)-alkyl, and more preferred is hydrogen.

[0127] R 2 Preferred is hydrogen, halogen or (C1-C3)-alkyl, and more preferably hydrogen.

[0128] R 6 Preferred is hydrogen, halogen or (C1-C3)-alkyl, and more preferably hydrogen.

[0129] Preferably,

[0130] R 2 is hydrogen, halogen, or (C1-C3)-alkyl; and

[0131] R 6 is hydrogen, halogen, or (C1-C3)-alkyl.

[0132] More preferably,

[0133] R 2 is hydrogen; and

[0134] R 6 It's hydrogen.

[0135] Preferably, R 3 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy, more preferably halogen or (C1-C3)-haloalkoxy, and in particular halogen.

[0136] Preferably, R 5 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy, more preferably hydrogen or halogen, and in particular halogen.

[0137] Preferably,

[0138] R 3 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; and

[0139] R 5 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy.

[0140] More preferably,

[0141] R 3 is halogen or (C1-C3)-haloalkoxy; and

[0142] R 5 is hydrogen or a halogen.

[0143] In particular,

[0144] R 3 is a halogen; and

[0145] R 5 It's a halogen.

[0146] Specifically,

[0147] R 3 is F or Cl; and

[0148] R 5 It is F or Cl.

[0149] Preferably, R 4 is hydrogen or halogen, and more preferably is hydrogen.

[0150] In particular, R 2 , R 4 and R 6 is hydrogen, and R 3 and R 5 It's a halogen.

[0151] Preferably, R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocycle W or a saturated or partially unsaturated 7- or 8-membered bicyclic heterocycle W, wherein ring W contains, in addition to this carbon atom, q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, wherein the sum of u, v and w is 1 or 2, and wherein ring W is surrounded by n radicals R b replace.

[0152] An example of such a ring W is

[0153]

[0154] The arrows indicate the bonds to the two C(O) groups. Possible substituents R are not shown. bThey may be bonded to carbon ring atoms or to secondary nitrogen ring atoms (the latter not exemplified in the above ring structures).

[0155] Preferably,

[0156] u is 1 or 2, v is 0 and w is 0; or

[0157] u is 1, v is 1 and w is 0; or

[0158] u is 1, v is 0 and w is 1; or

[0159] u is 0, v is 0 and w is 1.

[0160] More preferably, R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or

[0161] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b wherein n is 0, 1 or 2.

[0162] In particular, R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b Substitution, wherein n is 0 or 1.

[0163] Preferably, each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b More preferably, each R b are independently (C1-C2)-alkyl or (C1-C2)-haloalkyl; or two R bonded to the same carbon atom b In particular, each R b are independently (C1-C2)-alkyl or (C1-C2)-haloalkyl.

[0164] Preferably, R 9 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or (C1-C4)-alkyl, which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein m is 1, 2 or 3.

[0165] More preferably, R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members. The 5-membered heteroaromatic ring is preferably furanyl.

[0166] In particular, R 9 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furanyl.

[0167] Examples of ring W, where R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or R 7 and R 8Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2, and wherein each R b are independently (C1-C2)-alkyl or (C1-C2)-haloalkyl or two R bonded to the same carbon atom b Forming a methylene group (=CH2); is:

[0168]

[0169] The compounds of the invention having formula (I) may contain stereogenic centers (*), depending on the structure of ring W (the ring must not contain a ring carrying R that would be a stereogenic center). 7 and R 8 The mirror axis of the carbon atom is shown below:

[0170]

[0171] Therefore, if with R 7 and R 8 If the carbon atom to which ring W is bonded is a stereogenic center, the compound of formula (I) exists in two stereoisomeric forms (if no additional stereogenic centers are present; otherwise, the compound of formula (I) exists in more than two stereoisomeric forms; more precisely, in 2 n The invention also includes all stereoisomers and mixtures thereof.

[0172] In specific embodiments, the substituents have the following meanings:

[0173] R 1 is hydrogen or (C1-C3)-alkyl; preferably hydrogen;

[0174] R 2 is hydrogen, halogen or (C1-C3)-alkyl;

[0175] R 3 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0176] R 4 is hydrogen or halogen; preferably hydrogen;

[0177] R 5is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy;

[0178] R 6 is hydrogen, halogen or (C1-C3)-alkyl;

[0179] R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocycle W or a saturated or partially unsaturated 7- or 8-membered bicyclic heterocycle W, wherein ring W contains, in addition to this carbon atom, q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, wherein the sum of u, v and w is 1 or 2, and wherein ring W is surrounded by n radicals R b replace;

[0180] R 9 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or (C1-C4)-alkyl, which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein m is 1, 2 or 3.

[0181] More particularly, these substituents have the following meanings:

[0182] R 1 It is hydrogen;

[0183] R 2 It is hydrogen;

[0184] R 3 is halogen or (C1-C3)-haloalkoxy;

[0185] R 4 It is hydrogen;

[0186] R 5 is hydrogen or a halogen;

[0187] R 6 It is hydrogen;

[0188] R 7 and R 8together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or

[0189] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; wherein

[0190] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b Forming a methylene group (=CH2); and

[0191] R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members (wherein the 5-membered heteroaromatic ring is preferably furanyl);

[0192] Where R 9 Preferred is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl.

[0193] Specifically, these substituents have the following meanings:

[0194] R 1 It is hydrogen;

[0195] R 2 It is hydrogen;

[0196] R 3 It is a halogen;

[0197] R 4 It is hydrogen;

[0198] R 5 It is a halogen;

[0199] R 6 It is hydrogen;

[0200] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein

[0201] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and

[0202] R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members (wherein the 5-membered heteroaromatic ring is preferably furanyl);

[0203] Where R 9 Preferred is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl.

[0204] More specifically, these substituents have the following meanings:

[0205] R 1 It is hydrogen;

[0206] R2 It is hydrogen;

[0207] R 3 It is a halogen;

[0208] R 4 It is hydrogen;

[0209] R 5 It is a halogen;

[0210] R 6 It is hydrogen;

[0211] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated 4-membered monocyclic heterocycle W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, or a partially unsaturated 5-membered monocyclic heterocycle W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring W is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein

[0212] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and

[0213] R 9 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 substituent selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furanyl.

[0214] In the context of the present invention, compounds of formula (I) wherein R 1 , R 2 and R 6 is hydrogen and R 3 , R 4 , R 5 and W (W is composed of R 7 and R 8 Together with the carbon atom to which they are bound) have the meanings defined in rows 1 to 3696 of Table 1 below and are particularly preferred. 7 and R 8 In case the carbon atom bonded to form W is a chiral centre, both enantiomers as well as mixtures thereof are subject matter of the present invention.

[0215] Table 1:

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253] *) The variables A.1 to A.16 representing W in Table 1 above have the following meanings:

[0254]

[0255] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is hydrogen and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.1), ie individual compounds I.1.1 - I.1.3696), being particularly preferred.

[0256] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is methyl and R 3 , R 4 , R 5 and R 7 , R 8(together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.2), ie individual compounds I.2.1 - I.2.3696), being particularly preferred.

[0257] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is ethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.3), ie individual compounds I.3.1 - I.3.3696), being particularly preferred.

[0258] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-methoxyethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.4), ie individual compounds I.4.1 - I.4.3696), being particularly preferred.

[0259] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-(methylsulfanyl)-ethyl (=2-(methylthio)-ethyl) and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.5), ie individual compounds I.5.1 - I.5.3696), being particularly preferred.

[0260] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-(methylsulfonyl)-ethyl and R3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.6), ie individual compounds I.6.1 - I.6.3696), being particularly preferred.

[0261] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-(phenylsulfanyl)-ethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.7), ie individual compounds I.7.1 - I.7.3696), being particularly preferred.

[0262] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-chloroethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.8), ie individual compounds I.8.1 - I.8.3696), being particularly preferred.

[0263] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2-fluoroethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.9), ie individual compounds I.9.1 - I.9.3696), being particularly preferred.

[0264] Compound (I), wherein R 1 , R2 and R 6 is hydrogen, R 9 is 2,2-difluoroethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.10), ie individual compounds I.10.1 - I.10.3696), being particularly preferred.

[0265] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is 2,2,2-trifluoroethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.11), ie individual compounds I.11.1 - I.11.3696), being particularly preferred.

[0266] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is furan-2-yl-methyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.12), ie individual compounds I.12.1 - I.12.3696), being particularly preferred.

[0267] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is benzyl and R 3 , R 4 , R 5 and R 7 , R 8(together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.13), ie individual compounds I.13.1 - I.13.3696), being particularly preferred.

[0268] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is cyclopropylmethyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.14), ie individual compounds I.14.1 - I.14.3696), being particularly preferred.

[0269] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is cyclopropyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.15), ie individual compounds I.15.1 - I.15.3696), being particularly preferred.

[0270] Compound (I), wherein R 1 , R 2 and R 6 is hydrogen, R 9 is cyclobutyl and R 3 , R 4 , R 5 and R 7 , R 8 (together with the carbon atom to which they are bound to form W) have the meanings as defined above in rows 1 to 3696 of Table 1 (also referred to as compound (I.16), ie individual compounds I.16.1 - I.16.3696), being particularly preferred.

[0271] Compound (I) (wherein R 9 is hydrogen (carboxylic acid)) is commercially available or can be prepared from the corresponding ester (I); that is, from compound (I) (wherein R 9is not hydrogen) (hereinafter, such ester compound (I) is referred to as compound (I'), and R is not hydrogen 9 Known as R 91 ) preparation. If R 91 is an alkyl group, the ester (I') can be cleaved using an aqueous alkali metal hydroxide solution. Preferably, lithium hydroxide, sodium hydroxide or potassium hydroxide (1-2 equivalents) is used. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol or acetonitrile. The reaction is carried out at a temperature between 0°C and 100°C. Preferably, the reaction is carried out at room temperature. If R in (I') 91 If it is benzyl, palladium on carbon (0.001-1 equivalent) can be used as a catalyst and hydrogen at a temperature between 0°C and reflux to cleave the ester. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol or ethanol is used.

[0272]

[0273] Cyclic compounds of formula (I') can be prepared from cyclic carboxylic acids 2 and commercially available amines 1 using bases and coupling agents. Thus, compounds of formula (I') can be synthesized from the corresponding carboxylic acid (1 equivalent) using a coupling agent (1-2 equivalents) such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate)), an organic base (1-3 equivalents) and amine 1 (1-3 equivalents). The reaction is typically carried out in an organic solvent. Preferably, an aprotic organic solvent is used. Most preferably, tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN) is used. The reaction is carried out at a temperature between 0°C and the reflux temperature. Preferably, the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[0274]

[0275] Cyclic carboxylic acids 2 can be prepared from the corresponding diesters 3 by selective cleavage of one ester group. q If the alkyl ester is an alkyl ester, an aqueous base can be used to achieve selective ester cleavage. Preferably, an alkali metal hydroxide is used. Most preferably, lithium hydroxide, sodium hydroxide or potassium hydroxide is used. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, THF, methanol or acetonitrile is used. The reaction is carried out at a temperature between 0°C and 100°C, preferably at room temperature.

[0276] Alternatively, trimethyltin hydroxide (e.g. 1 equivalent) in 1,2-dichloroethane at room temperature to reflux (as described in Angew. Chem. Int. Ed [Applied Chemistry International Edition], 2005, 44: 1378-1382) can be used, preferably at reflux. q If it is benzyl, the ester can be cleaved using palladium on carbon (0.001-1 equivalent) as a catalyst and hydrogen at a temperature between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is employed.

[0277] Preferably, THF, methanol or ethanol is used.

[0278]

[0279] Cyclic diester 3 can be synthesized from commercially available cyclic monoester 4, base and chloroformate 5 (1-3 equivalents) as described in Bioorganic & Medicinal Chemistry Letters, 12 (11), 1501-1505; 2002. The reaction is typically carried out in an organic solvent, preferably tetrahydrofuran. A suitable temperature range is between -78°C and 25°C. Preferably, the reaction is allowed to warm from -78°C to 25°C over a period of 16 h. Preferably, lithium diisopropylamide (1 equivalent) is used as the base.

[0280] Alternatively, specific cyclic diesters can be prepared according to the following method:

[0281]

[0282] Alternatively, the cyclic diester 3a can be prepared from commercially available diethyl dibromomalonate 6a, a base and an alcohol or thiol having formula 7 (V is -CH2CH2- or

[0283] -CH2CH2CH2-, which is optionally replaced by R b substituted; each A is independently selected from O, S, NH and NR b1 , A' is independently selected from OH, SH, NHR b1 , and R b1The reaction is typically carried out in an organic solvent, preferably in tetrahydrofuran. The suitable temperature range is between 0°C and 25°C. Preferably, sodium hydride (2 equivalents) is used as the base.

[0284]

[0285] Cyclic diesters of formula 3b containing oxy-heterocycles are commercially available or can be prepared from the corresponding diazo-compounds 6b using dimeric rhodium acetate ([Rh(OAc)2]2) (0.001-0.1 equivalents) and commercially available halogenated (Hal=Cl, Br) alcohols of formula 8 (V is -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, optionally with R b substituted), followed by cyclization using sodium hydride (1.2 eq.) in N,N-dimethylformamide (DMF) as described in Angew. Chem. Int. Ed., 2014, 53, 14230-14234.

[0286]

[0287] Alternatively, the cyclic unsaturated diester of formula 3c containing an oxy-heterocycle can be prepared from the corresponding diazo-compound 6b using dimeric rhodium acetate ([Rh(OAc)2]2) (0.001-0.1 equivalents) and an alcohol of formula 9 (U is -CH2- or -CH2CH2-, optionally replaced by R b substituted), followed by cyclization using cesium carbonate (2.0 equiv.) in acetonitrile. A suitable temperature range is from room temperature to 60°C.

[0288]

[0289] The N-heterocyclic ring-containing cyclic diester 3d can be prepared from the corresponding diazo-compound 6b using bis[rhodium (α, α, α', α'-tetramethyl-1,3-benzenedipropionic acid)] ([Rh(esp)]2, CAS [819050-89-0]) (0.001-0.1 equivalents) and a halogen (Hal = Br, Cl)-containing amine of formula 10 (V is -CH2CH2-, -CH2CH2CH2- or -CH2CH2CH2CH2-, optionally replaced by R b substituted) in toluene at 60 ° C, followed by the addition of cesium hydroxide monohydrate (2 equivalents) and tetrabutylammonium bromide (0.1 equivalents) as described in Angew. Chem. Int. Ed. [Applied Chemistry International Edition], 2019, 58, 1458-1462. b1 It is hydrogen, (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 or (C1-C3)-alkylsulfonyl.

[0290]

[0291] An unsaturated diester containing an O-heterocycle of formula 3e (U is -CH2- or

[0292] -CH2CH2-) can be prepared from commercially available ketomalonate (CAS 609-09-6) 6c using cyclic or acyclic dienes of formula 11 in acetonitrile at 130°C as described in J. Org. Chem. 1977, 42, 4095-4103. Alternatively, heating is carried out at 130°C for 4 h by irradiating the reaction mixture with microwaves (300 W).

[0293]

[0294] The corresponding N-heterocyclic unsaturated diester of formula 3f (U is -CH2- or

[0295] -CH2CH2-) can be similarly prepared from the corresponding iminomalonate 6d using a cyclic or acyclic diene of formula 11 in tetrahydrofuran at 100°C as described in Tetrahedron Lett. 1981, 22, 4607; Synth. Commun. 1972, 2, 211; and J. Med. Chem. 1973, 16, 853, or by irradiating the reaction mixture with microwaves (100°C, 4h, 300W). b1 It is hydrogen, (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 or (C1-C3)-alkylsulfonyl.

[0296]

[0297] The corresponding triazoline of formula 3g can be prepared from commercially available olefins of formula 6e using azides of formula 12 using catalytic amounts of N,N-dimethylurea in toluene at 60°C as described in Org. Lett. [Organic Chemistry Communications] 2015, 17, 4568-4571. b1 R is hydrogen, (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 or (C1-C3)-alkylsulfonyl. Each R b2 are independently hydrogen or have a b One of the meanings given.

[0298] The compounds of the invention having formula (I) may contain stereogenic centers (*), depending on the structure of ring W (the ring must not contain a ring carrying R that would be a stereogenic center). 7 and R 8 The mirror axis of the carbon atom is shown below:

[0299]

[0300] Therefore, if with R7 and R 8 If the carbon atom to which ring W is bonded is a stereogenic center, the compound of formula (I) exists in two stereoisomeric forms (if no additional stereogenic centers are present; otherwise, the compound of formula (I) exists in more than two stereoisomeric forms; more precisely, in 2 n The invention also includes all stereoisomers and mixtures thereof.

[0301] In order to broaden the spectrum of action, the compounds of formula (I) can be mixed with representatives of many other herbicidal or growth regulating active ingredient groups and then applied simultaneously. Suitable components for combination are, for example, herbicides from the following classes: acetamide, amide, aryloxyphenoxypropionate, benzamide, benzofuran, benzoic acid, benzothiadiazinone, bipyridylium, carbamate, chloroacetamide, chlorocarboxylic acid, cyclohexanedione, dinitroaniline, dinitrophenol, diphenyl ether, glycine, imidazolinone, isoxazole, isoxazolidinone, nitrile, N-phenylphthalimide, oxadiazole, oxazolidinedione, glycolamide, phenoxycarboxylic acid, phenylamino formic acid esters, phenylpyrazole, phenylpyrazoline, phenylpyridazine, phosphinic acid, phosphoramidate, phosphorodithioate, o-carbamoylbenzoate, pyrazole, pyridazinone, pyridine, pyridinecarboxylic acid, pyridinecarboxamide, pyrimidinedione, pyrimidinyl(thio)benzoate, quinolinecarboxylic acid, semicarbazone, sulfonylaminocarbonyltriazolinone, sulfonylurea, tetrazolinone, thiadiazole, thiocarbamate, triazine, triazone, triazole, triazolinone, triazolocarboxamide, triazolopyrimidine, triketone, uracil, urea.

[0302] Furthermore, it may be useful to apply the compounds of formula (I) alone or in combination with other herbicides or else in the form of a mixture with other crop protection agents, for example with agents for controlling harmful organisms or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions for treating nutrient and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

[0303] In one embodiment of the present invention, the combination according to the present invention comprises at least one compound of formula (I) (compound A or component A) and at least one additional active compound selected from the group consisting of herbicides B (compound B) (preferably herbicides B of classes b1) to b15)) and safeners C (compound C).

[0304] In a further embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one further active compound B (herbicide B).

[0305] Examples of herbicides B which can be used in combination with the compounds A of formula (I) according to the invention are:

[0306] b1) From the group of lipid biosynthesis inhibitors:

[0307] ACC-herbicides such as diclofop, diclofop-sodium, clodinafop-butyl, clethodim, clodinafop-butyl, clodinafop-butyl, cyhalofop-butyl, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-butyl p-P), fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, oxadiazine, pinoxadone, cyproconazole, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-ethyl lofop-P-ethyl), quizalofop-P-tefuryl, sethoxydim, pyraclostrobin, oxaclostrobin, 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-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312337-48-6);5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonate(CAS1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)- 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl furan-3-yl carbonate methyl ester (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, pyraclostrobin, EPTC, pentocarb, ethoxyfuroxan, tetrafluoropropionic acid, molinate, orbencarb, pebulate, benfuresate, TCA, molinate, orbencarb, pebulate, ernolate, and ernolate;

[0308] b2) From the group of ALS inhibitors:

[0309] Sulfonylureas, such as sulfamethoxazole, tetrazosulfuron-methyl, benzylsulfuron-methyl, benzylsulfuron-methyl, chlorimuron-methyl, chlorimuron-ethyl, chlorimuron, ethoxysulfuron-methyl, cyprosulfuron-methyl, ethametsulfuron-methyl, ethoxysulfuron-methyl, flazasulfuron-methyl, flutosulfuron-methyl, flutosulfuron-methyl, flutosulfuron-methyl-sodium, foramsulfuron-methyl, chlorimuron-methyl, chlorimuron-methyl, chlorimuron-methyl, iodosulfuron-methyl, iodosulfuron-methyl, iodosulfuron-methyl-sodium, disulfuron acid, azine metazosulfuron, metsulfuron-methyl, metsulfuron-methyl, nicosulfuron, pyrimidosulfuron-methyl, oxasulfuron-methyl, primisulfuron-methyl, primisulfuron-methyl, promazinesulfuron-methyl, prosulfuron, pyrazosulfuron-methyl, pyrazosulfuron-ethyl, sulfasulfuron-methyl, sulfasulfuron-methyl, sulfasulfuron-methyl, thifensulfuron-methyl, thifensulfuron-methyl, bensulfuron-methyl, bensulfuron-methyl, bensulfuron-methyl, trifloxysulfuron, trifloxysulfuron, trifloxysulfuron-methyl and trifloxysulfuron,

[0310] imidazolinones such as imazapic, imazapic-methyl, imazapic-methyl, imazapic-methyl, imazapic-pyr, imazapic-pyr, imazapic-quin and imazapic-pyr, triazolopyrimidine herbicides, and sulfonanilides such as clofosulphonic acid, clofosulphonic acid-methyl, bisclosulam, fluazifop, bispyribac, sulfamethoxam, penoxsulam, pyrimisulfan and pyrimisulfan,

[0311] Pyrimidinyl benzoates, such as bispyribac-sodium, bispyribac-sodium, pyrimidinylpyrimidinyl, pyrimidinylpyrimidinyl, pyrimidinylpyrimidinyl acid, pyrimidinylpyrimidinyl acid-methyl, pyrimidinylpyrimidinyl, pyrimidinylpyrimidinyl-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8),

[0312] Sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiamethoxam acid and thiamethoxam methyl; and flucarbazone;

[0313] Among them, preferred embodiments of the present invention relate to those compositions comprising at least one imidazolinone herbicide;

[0314] b3) From the group of photosynthesis inhibitors:

[0315] Amitriptyline, inhibitors of photosystem II, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1- (5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrrol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrrol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one )-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2 -ketone (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one (CAS1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS1844836-64-1), triazine herbicides, including chlorotriazines, triazinones, triazindiones, methylthiotriazines, and pyridazinones, such as ametryn, atrazine , chloranil, cyanazine, dichlorvos, isopentanol, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn and trietazin, aryl ureas such as chlorbromide, chlorotoluron, chloroxuron, oxazolone, diuron, flumethuron, isoproturon, isoxuron, linuron, metamitron, methylbenzene, pyranuron, methoxuron, chlorothiazuron, cypermethrin, thiocarb, and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, betaine -ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, iobenzonil and its salts and esters, uracils such as cypermethrin, cypermethrin and terpyrimidine, as well as bentazone and bentazone-sodium, pyridate, pyridafol, mechlorethamide and propanil, and inhibitors of photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-bis-methylsulfate. Among them, preferred embodiments of the present invention relate to those compositions comprising at least one aryl urea herbicide. Among them, preferred embodiments of the present invention also relate to those compositions comprising at least one triazine herbicide. Among them, preferred embodiments of the present invention also relate to those compositions comprising at least one nitrile herbicide;,

[0316] b4) from the group of protoporphyrinogen-IX oxidase inhibitors:

[0317] Acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzylpyridin, chlorphthalim, flufenpyr, flufenpyr-ethyl, chlorphthalim, chlorphthalim, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flufenoxal, flufenoxal pentyl, flumioxazin, fluoroglycofen, fluoroglycofen ethyl, flufenoxal, flufenoxal methyl, flumioxazin, halosafen, lactofen, oxadiargyl, Oxadiazole, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraclostrobin, pyraclostrobin ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-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]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS1304113-05-0), (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoic acid methyl ester (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6- Methyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS2158274-96-3), ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS158274-50-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- Oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridinyl]oxy]acetic acid methyl ester (CAS2271389-22-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS2230679-62-4), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- )-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (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]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS2158274-56-5),6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS2158276-22-1);

[0318] b5) From the group of the bleaching agent herbicides:

[0319] PDS inhibitors: fluazifop, flufenac, flupyralidone, flurochloridone, furazolidone, fluazifop, flupyralidone, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, flupyralidone, clomazone, fenquinone, isoxaflutole, mesotrione, oxotrione (CAS1486617-21-3 ), pyrazolynate, pyrazoxyfen, sulfotrione, tefuryltrione, cypermethrin, pyraclostrobin, bleaching agents, unknown targets: aclonifen, cypermethrin, fluazifop-butyl, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS1361139-71-0), bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS81778-66-7);

[0320] b6) From the group of EPSP synthase inhibitors:

[0321] glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimethylsulfide (glyphosate-sulfide);

[0322] b7) From the group of glutamine synthase inhibitors:

[0323] Bialaphos (bialaphos), bialaphos-sodium, glufosinate, glufosinate-fine, and glufosinate-ammonium;

[0324] b8) From the group of DHP synthase inhibitors:

[0325] Asulam;

[0326] b9) From the group of mitotic inhibitors:

[0327] K1 group compounds: dinitroanilines, such as fluazifop, butalin, dimethoate, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin; phosphamides, such as phosphoamidophos, phosphoamidophos-methyl and butamiphos; benzoic acid, such as Herbicides, such as chlorthal, chlorthal-dimethyl, pyridines, such as dithiopyr and thiamethoxam, benzamides, such as propyzamide and tebutam; K2 group compounds: carbetamide, chlorpropamide, chlorpyrifos, chlorpyrifos-isopropyl, chlorpyrifos-methyl, chlorpyrifos-isopropyl, chlorpyrifos-methyl and chlorpyrifos; among them, K1 group compounds, especially dinitroanilines, are preferred;

[0328] b10) from the group of VLCFA inhibitors:

[0329] Chloroacetamides, such as acetochlor, alachlor, acetamiprid, butachlor, dimethachlor, dimethenamid, dimethenamid-S, pyraclostrobin, metolachlor, metolachlor-S, pethoxamid, pretilachlor, chlorfenapyr, propisochlor, and thenylchlor, oxyacetanilides, such as flufenacet and mefenacet, acetanilide herbicides such as diphenamid, naproxenamide, naproxenamide and naproxenamide-M, tetrazolinones such as fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, pyroxasulfone, and isoxazoline compounds of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

[0330]

[0331]

[0332] Isoxazoline compounds of formula (II) are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0333] Among the VLCFA inhibitors, preferred are chloroacetamides and oxyacetamides;

[0334] b11) from the group of the cellulose biosynthesis inhibitors:

[0335] Fenpyraclostrobin, dichlorvos, fluazifop, indazine fluazifop, isoxadiazine, triazine fluazifop and 1-cyclohexyl-5-pentafluorophenoxy-1 4 -[1,2,4,6]thiatriazine-3-ylamine (CAS175899-01-1);

[0336] b12) from the group of the decoupling herbicides:

[0337] Dinoseb, dinoterb and DNOC and their salts;

[0338] b13) from the group of the auxin herbicides:

[0339] 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-tri(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, chloroformyl Clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, 2,4-dichlorprop and its salts and esters, flopyrauxifen, fluroxypyr, flopyrauxifen butoxyisopropyl, flopyrauxifen ethylhexyl, 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, s-methyltetrachloropropionic acid and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);

[0340] b14) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

[0341] b15) From the group of other herbicides: bromobutyric acid, cloroxyl fluorene acid, cloroxyl fluorene acid-methyl, cyproconazole, benzyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomethan, difluanid, difluanid-methyl sulfonate, thiamethoxam, DSMA, cypermethrin, endoxan and its salts, ethoxybencarb, fluorenebutyric acid, fluorenebutyric acid-butyl, furamidol, cypermethrin, cypermethrin ammonium, indole, maleic hydrazide, fluosulphan, metamidine, methoxythiazide, methyl azide, methyl bromide, methyl-cypermethrin, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, cypermethrin, tetrafluanid, and cypermethrin.

[0342] In addition, it may be useful to apply the compound of formula (I) in combination with a safener. Safeners are chemical compounds that prevent or reduce damage to useful plants and do not have a significant impact on the herbicidal action of the compound of formula (I) against undesirable vegetation. They can be applied before sowing of useful plants (e.g., on seed treatment, branches or seedlings) or before or after emergence. Safeners and compounds of formula (I) and optional herbicides B can be applied simultaneously or sequentially.

[0343] In a further embodiment of the present invention, the combination according to the invention comprises at least one compound of the formula (I) and at least one safener C (component C).

[0344] Examples of safeners are, for example, (quinolin-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oximinophenylacetonitrile, acetophenone oxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamide, 1,8-naphthalene dicarboxylic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided that they have an acid group.

[0345] Examples of safener compounds C are fenoxazolidinone, fenchlorazole, fenclorim, fenoxaprozil, cyprosulfonamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalene dicarboxylic anhydride, fenoxaprozil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), sulfonamide and BPCMS (CAS 54091-06-4).

[0346] Active compounds B and active compounds C of groups b1) to b15) are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Vol. 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, RR Schmidt, Herbizides, Georg Thieme Verlag, Stuttgart 1995; WH Hrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and KK Hatzios, Herbicide Handbook, Supplement to 7th edition, Weed Science Society of America, 1996. America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also known as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660.

[0347] The active compounds were assigned to the corresponding mechanisms of action based on current knowledge. If several mechanisms of action were applicable to an active compound, this substance was assigned to only one mechanism of action.

[0348] In addition, the present invention relates to a herbicidal composition comprising at least one compound having formula (I) as defined above, an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof, and at least one adjuvant commonly used in the formulation of crop protection compounds. The adjuvant commonly used in the formulation of crop protection compounds is defined as follows.

[0349] In addition, the present invention also relates to a herbicidal composition comprising at least one compound with formula (I) as defined above and a herbicide different from the compound with formula (I). Suitable herbicides are as defined above. In a specific embodiment, the composition according to the present invention does not encompass a composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid and one or more of the following solvents as a compound with formula (I): acetonitrile, ethyl acetate, water, methanol, tetrahydrofuran. More particularly, the composition according to the present invention does not encompass a composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid (regardless of the nature of the other components present in the composition), and does not encompass a composition comprising 2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester.

[0350] In another specific embodiment, the composition according to the present invention does not encompass such compounds, which simultaneously contain one of the following compounds:

[0351] Compound (I), wherein

[0352] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), 2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-O-), 3,5-dimethyl-2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -C(CH3)=CH-CH(CH3)-O-), oxathiolane-2,2-diyl (ie, R 7 and R 8 Together, they form a bridging group -S-CH2-CH2-O-), 1,3-dioxolane-5,5-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-O-CH2-O-), 3-methyl-4,5-dihydroisoxazole-5,5-diyl (ie, R 7 and R 8 together to form a bridging group -CH2-C(CH3)=NO-), or

[0353] And R 9 is hydrogen or ethyl;

[0354] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-) or 2,5-dihydrothiophene-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-S-), and R 9 is hydrogen or methyl;

[0355] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It's F, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), and R 9 is hydrogen or ethyl;

[0356] and one or more of the following solvents: N,N-dimethylformamide, acetonitrile, ethyl acetate, water, methanol, ethanol, tetrahydrofuran, methyl tert-butyl ether, toluene, pentane, and dichloromethane.

[0357] The formulation comprises a pesticidal effective amount of a compound of formula (I). The term "effective amount" indicates a combination or amount of a compound of formula (I) sufficient to control undesirable vegetation, especially undesirable vegetation in crops (i.e., cultivated plants) and which does not produce significant damage to the treated crop plants. This amount can vary over a wide range and depends on various factors, such as undesirable vegetation to be controlled, the treated crop plants or materials, climatic conditions, and the specific compound of formula (I) used.

[0358] The compound of formula (I) or its salt can be converted into conventional types of formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, molded products, capsules and mixtures thereof. Examples of formulation types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), molded products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticide preparations (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and additional formulation types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition, May 2008, CropLife International.

[0359] The formulations are prepared in a known manner, as described, for example, by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS 243, T&F Informa, London, 2005.

[0360] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[0361] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, for example kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0362] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, for example cereal flour, bark flour, wood flour, nut shell flour and mixtures thereof.

[0363] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American Edition).

[0364] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. The example of sulfonates is alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, fatty acids and oily sulfonates, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, sulfonates of dodecyl- and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalene, sulfosuccinates or sulfosuccinamates. The example of sulfates is sulfates of fatty acids and oily sulfates, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. The example of phosphates is phosphate esters. The example of carboxylates is alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0365] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated by 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0366] Suitable cationic surfactants are quaternary ammonium surfactants, for example quaternary ammonium compounds with 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 comprising blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polyalkalis. The example of polyacids is the alkali metal salt of polyacrylic acid or polyacid comb-like polymers. The example of polyalkalis is polyvinylamine or polyvinylamine.

[0367] Suitable adjuvants are compounds that have negligible pesticidal activity or even no pesticidal activity and improve the biological performance of the compound of formula (I) to the target. Examples are surfactants, mineral oils 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.

[0368] Suitable thickeners are polysaccharides (eg, xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0369] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

[0370] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0371] Suitable defoamers are silicones, long chain alcohols, and salts of fatty acids.

[0372] Suitable colorants (for example red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic colorants (for example iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (for example alizarin colorants, azo colorants and phthalocyanine colorants).

[0373] Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0374] Examples of formulation types and their preparation are:

[0375] i) Water-soluble concentrates (SL, LS)

[0376] 10 wt% to 60 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C) and 5 wt% to 15 wt% of a wetting agent (e.g. alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g. alcohol) to 100 wt%. The active substance dissolves when diluted with water.

[0377] ii) Dispersible Concentrate (DC)

[0378] 5 wt% to 25 wt% of the compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) and 1 wt% to 10 wt% of a dispersant (e.g. polyvinyl pyrrolidone) are dissolved in an organic solvent (e.g. cyclohexanone) added to 100 wt%. Dilution with water gives a dispersion.

[0379] iii) Emulsifiable concentrates (EC)

[0380] 15 wt% to 70 wt% of the compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) and 5 wt% to 10 wt% of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g. aromatic hydrocarbon) added to 100 wt%. Dilute with water to obtain an emulsion.

[0381] iv) Emulsion (EW, EO, ES)

[0382] 5 wt% to 40 wt% of the compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) and 1 wt% to 10 wt% of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 wt% to 40 wt% of a water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into 100 wt% of water by means of an emulsifier and a uniform emulsion is prepared. The emulsion is obtained by dilution with water.

[0383] v) Suspension (SC, OD, FS)

[0384] In a stirred ball mill, 20% to 60% by weight of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compound B (component B) and safener C (component C) are comminuted with addition of 2% to 10% by weight of dispersants and wetting agents (e.g. sodium lignin sulfonates and alcohol ethoxylates), 0.1% to 2% by weight of thickeners (e.g. xanthan gum) and up to 100% by weight of water to give a finely divided active substance suspension. Dilution with water gives a stable active substance suspension. For FS type formulations, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0385] vi) Water dispersible granules and water soluble granules (WG, SG)

[0386] 50 wt% to 80 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground with up to 100 wt% of dispersants and wetting agents (e.g. sodium lignin sulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble granules by means of industrial equipment (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable active substance dispersion or solution.

[0387] vii) Water dispersible powders and water soluble powders (WP, SP, WS)

[0388] 50 wt% to 80 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C) is ground in a rotor-stator mill with the addition of 1 wt% to 5 wt% of a dispersant (e.g. sodium lignin sulfonate), 1 wt% to 3 wt% of a wetting agent (e.g. alcohol ethoxylate) and up to 100 wt% of a solid carrier (e.g. silica gel). Dilution with water gives a stable active substance dispersion or solution.

[0389] viii) Gel (GW, GF)

[0390] In a stirred ball mill, 5% to 25% by weight of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compound B (component B) and safener C (component C) are comminuted with addition of 3% to 10% by weight of a dispersant (e.g. sodium lignin sulfonate), 1% to 5% by weight of a thickener (e.g. carboxymethylcellulose) and up to 100% by weight of water to give a finely divided active substance suspension. Dilution with water gives a stable active substance suspension.

[0391] iv) Microemulsion (ME)

[0392] 5 wt% to 20 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) is added to 5 wt% to 30 wt% of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10 wt% to 25 wt% of a surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate) and to 100 wt% of water. This mixture is stirred for 1 h to spontaneously generate a thermodynamically stable microemulsion.

[0393] iv) Microcapsules (CS)

[0394] An oil phase comprising 5 wt% to 50 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C), 0 wt% to 40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), 2 wt% to 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 wt% to 50 wt% of a compound of formula (I) according to the invention, 0 wt% to 40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon) and an isocyanate monomer (e.g., diphenylmethylene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of polyamines (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is 1 wt% - 10 wt%. wt% relative to the total CS formulation.

[0395] ix) Dustable powders (DP, DS)

[0396] 1 wt% to 10 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground and intimately mixed with a solid carrier (e.g. finely divided kaolin) added to 100 wt%.

[0397] x) Granules (GR, FG)

[0398] 0.5 wt% to 30 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground and combined with up to 100 wt% of a solid carrier (e.g. a silicate). Granulation is achieved by extrusion, spray drying or fluidized bed.

[0399] xi) Ultra Low Volume Liquid (UL)

[0400] 1 wt% to 50 wt% of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicidal compound B (component B) and safener C (component C) is dissolved in an organic solvent (e.g. an aromatic hydrocarbon) added to 100 wt%.

[0401] Formulation types i) to xi) may optionally comprise further auxiliaries, such as 0.1 wt% to 1 wt% bactericide, 5 wt% to 15 wt% antifreeze agent, 0.1 wt% to 1 wt% antifoaming agent, and 0.1 wt% to 1 wt% colorant.

[0402] The formulations and / or combinations generally contain between 0.01% and 95%, preferably between 0.1% and 90% and in particular between 0.5% and 75% by weight of the compound of formula (I).

[0403] The compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0404] Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used for the purpose of treating plant propagation material, in particular seeds. The formulations in question give active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use formulations after two- to ten-fold dilution. (nach unten verschoben)

[0405] The method for applying the compound of formula (I), its preparation and / or combination to plant propagation materials, especially seeds comprises seed dressing, coating, granulation, dusting, soaking and in-furrow application method of propagation materials. Preferably, the compound of formula (I), its preparation and / or combination is applied to plant propagation materials respectively by seed dressing, granulation, coating and dusting by making the method that germination is not induced.

[0406] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and additional pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added as premixes to the compounds of formula (I), the formulations and / or combinations comprising them or (if appropriate) not added until just before use (tank mix). These agents can be mixed with the formulations according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0407] The user usually uses a pre-dosing device, a backpack sprayer, a spray can, a spray aircraft or an irrigation system to apply the compound with formula (I) according to the present invention, the preparation and / or combination comprising them. Usually, the preparation is supplemented to the desired application concentration with water, a buffer, and / or an additional adjuvant and thereby obtains a ready-to-use spray liquid or a preparation according to the present invention. Usually, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of agricultural available area.

[0408] According to one embodiment, the individual components or partially premixed components of the formulation according to the invention (e.g. the component comprising the compound of formula (I) and optionally the active substance from groups B and / or C)) can be mixed by the user in a spray tank and further auxiliaries and additives can be added if appropriate.

[0409] In a further embodiment, the individual components of the formulation according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank and further auxiliaries can be added if appropriate.

[0410] In a further embodiment, the individual components or partially premixed components of the formulations according to the invention, for example the component comprising the compound of formula (I) and optionally the active substances from groups B and / or C), can be applied jointly (for example after tank mixing) or sequentially.

[0411] In a preferred embodiment, the adjuvant comprises a liquid carrier and / or a solid carrier, wherein the liquid carrier is selected from the group consisting of: water, an organic solvent and a mixture thereof, wherein the organic solvent is selected from the group consisting of: a mineral oil fraction, such as kerosene or diesel; an oil of plant or animal origin; paraffin, tetralin, alkylated naphthalene; an alcohol, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or a diol; DMSO; a ketone, such as cyclohexanone; an ester other than ethyl acetate, such as lactic acid esters, carbonates, fatty acid esters, γ-butyrolactone; Esters; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof; and wherein these solid carriers are preferably selected from the group consisting of silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal flour, bark flour, wood flour, nut shell flour and mixtures thereof;

[0412] Wherein, in the case where the adjuvant comprises water, the composition preferably further comprises a surface-active compound, wherein the surface-active compound is preferably selected from the group consisting of anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. More details of suitable surfactants are given above.

[0413] In another preferred embodiment, the adjuvant comprises water and a surface-active compound.

[0414] In another preferred embodiment, the composition comprises a herbicide other than the compound of formula (I).

[0415] Furthermore, the invention relates to a method for controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound (I) as defined above or a composition as defined above to act on the plants, their seeds and / or their habitat.

[0416] The compounds of formula (I) are suitable as herbicides. They are suitable as such or in combination with at least one further compound selected from the group consisting of herbicidally active compounds B (component B) and safeners C (component C) as appropriate formulations.

[0417] Compounds of formula (I) or formulations and / or combinations comprising compounds of formula (I) are very effective in controlling undesirable vegetation in non-crop areas, especially at high application rates. They act on broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low application rates.

[0418] In particular, the compounds of formula (I) or formulations and / or combinations comprising the compounds of formula (I) can be used to control at least one of the following undesirable plant species: Abutilon theophrasti (ABUTH), Alopercurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Apera spica-venti (APESV), Avena fatua (AVEFA), Echinocloacrus-galli (ECHCG), Lolium multiflorum (LOLMU), Fallopia convolvulus (POLCO), Setaria viridis (SETVI), Setaria faberi (SETFA).

[0419] Compounds of formula (I) or preparations and / or combinations comprising them are mainly applied to plants by spraying leaves. Here, application can be carried out using, for example, water as a carrier by conventional spraying techniques using a spraying liquid amount from about 100 l / ha to 1000 l / ha (e.g., from 300 l / ha to 400 l / ha). Compounds of formula (I) or preparations and / or combinations comprising them can also be applied by low-volume or ultra-low-volume methods or in the form of microgranules.

[0420] The application of the compounds of formula (I) or formulations and / or combinations comprising them can be carried out before, during and / or after, preferably during and / or after, the emergence of the undesired vegetation.

[0421] The application of the compounds or formulations of formula (I) and / or combinations can be carried out before or during sowing.

[0422] Compound with formula (I) or preparation and / or combination comprising them can be used before emergence, after emergence or before planting, or applied together with the seed of crop plants. Compound with formula (I) or preparation and / or combination comprising them can also be applied by applying the seed of crop plants with compound with formula (I) or preparation and / or combination pretreatment. If active component is not well tolerated by some crop plants, spraying combination by means of spray equipment can be used, in a way that they do not contact the leaves of sensitive crop plants as far as possible, and active component is reached to grow in the leaves of undesirable vegetation below or the application technology of exposed soil surface (post-seedling base application (post-directed, last pass field operation) .

[0423] In a further embodiment, the compounds of formula (I) or the preparations and / or combinations comprising them can be applied by treating the seeds. The treatment of seeds includes essentially all procedures familiar to those skilled in the art based on the compounds of formula (I) or the preparations and / or combinations prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed coating, seed multilayer coating, seed shelling, seed dripping and seed pelleting). Here, the combination can be applied diluted or undiluted.

[0424] The term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, rice seedlings and similar forms. Here, preferably, the term seed describes corn and seeds. The seeds used can be seeds of the crop plants mentioned above, but can also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0425] When used in plant protection, the amount of active substance applied (i.e. compound of formula (I), component B and, if appropriate, component C without formulation auxiliaries) is, depending on the kind of effect desired, from 0.001 to 2 kg / ha, preferably from 0.005 to 2 kg / ha, more preferably from 0.05 to 0.9 kg / ha and in particular from 0.1 to 0.75 kg / ha.

[0426] In another embodiment of the invention, the application rates of the compound of formula (I), component B and, if appropriate, component C are from 0.001 to 3 kg / ha, preferably from 0.005 to 2.5 kg / ha and in particular from 0.01 to 2 kg / ha of active substance (as).

[0427] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) according to the present invention (total amount of the compound of formula (I)) is from 0.1 g / ha to 3000 g / ha, preferably from 10 g / ha to 1000 g / ha, depending on the control target, season, target plant and growth stage.

[0428] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is in the range of from 0.1 g / ha to 5000 g / ha and preferably in the range of from 1 g / ha to 2500 g / ha or from 5 g / ha to 2000 g / ha.

[0429] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is 0.1 to 1000 g / ha, preferably 1 to 750 g / ha, more preferably 5 to 500 g / ha.

[0430] The desired application rate of the herbicidal compound B is generally in the range of from 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of from 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / h as.

[0431] The desired application rate of safener C is generally in the range of from 0.0005 kg / ha to 2.5 kg / ha and preferably in the range of from 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / h as.

[0432] In the treatment of plant propagation material such as seeds, for example by dusting, coating or soaking, an amount of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g per 100 kg of plant propagation material, preferably seeds, is generally required.

[0433] In another embodiment of the invention, for the treatment of seeds, the amount of active substance applied (ie compound of formula (I), component B and, if appropriate, component C) is generally employed in an amount of from 0.001 to 10 kg / 100 kg of seeds.

[0434] When used for the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. Usually the amount applied for the protection of materials is 0.001g to 2kg, preferably 0.005g to 1kg of active substance per cubic meter of treated material.

[0435] In the case of the combinations according to the invention, it is immaterial whether the compound of the formula (I) and the further component B and / or component C are formulated and applied jointly or separately.

[0436] In the case of separate application, the order in which the application occurs is not very important. It is only necessary that the compound of formula (I) and the additional component B and / or component C are applied within a time frame that allows the active ingredients to act simultaneously on the plant, preferably within a time frame of up to 14 days, in particular up to 7 days.

[0437] Depending on the application method in question, the compounds of formula (I) or formulations and / or combinations comprising them can additionally be used in a further number of crop plants to eliminate undesirable vegetation. Examples of suitable crops are as follows:

[0438] 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), rapeseed (Brassica napus var.napus), turnip (Brassica napus var.napobrassica), turnip (Brassica rapa var.silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), large-leaf tea (Camellia sinensis), safflower (Carthamus tinctorius), American pecan (Caryaillinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruit coffee (Coffea arabica) (medium-fruit coffee (Coffea canephora), large-fruit coffee (Coffea liberica), cucumber (Cucumissa tivus), bermudagrass (Cynodon dactylon), carrot (Daucus carota), oil palm (Elaeisguineensis), European strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum), (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), rubber tree (Hevea brasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersiconlycopersicum), apple (Malus) species, cassava (Manihot esculenta), alfalfa (Medicago sativa), Musa species, Nicotiana tabacum (N.rustica), olive (Oleaeuropaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus) species, pistachio (Pistacia vera), pea (Pisum sativum), European sweet cherry (Prunus avium), peach (Prunus persica), pear (Pyrus communis), apricot (Prunus armeniaca), European sour cherry (Prunus cerasus), almond (Prunus dulcis) and European plum (Prunus domestica), currant (Ribes sylvestre), castor (Ricinus communis), sugar cane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapisalba), potato (Solanum tuberosum), sorghum (Sorghum bicolor) (sorghum (s. vulgare)), cocoa (Theobromacacao), red clover (Trifolium pratense), common wheat (Triticum aestivum), triticale (Triticale), durum wheat (Triticum durum), broad bean (Vicia faba), grape (Vitis vinifera) and maize (Zea mays).

[0439] Preferred crops are groundnut, sugar beet (Beta vulgaris spec. altissima), rapeseed, kale, lemon, sweet orange, small-fruit coffee (Coffea canephora, Coffea macrocarpa), bermudagrass, soybean, upland cotton, (Gossypium hirsutum, Gossypium vitifolium), sunflower, barley, walnut, lentil, flax, tomato, apple species, alfalfa, tobacco (Nicotiana vulgaris), olive, rice, golden bean, bean, pistachio, pea, almond, sugarcane, rye, potato, sorghum, triticale, common wheat, durum wheat, broad bean, grape and maize.

[0440] Particularly preferred crops are cereals, corn, soybeans, rice, rapeseed, cotton, potatoes, peanuts or perennial crops.

[0441] The compounds of formula (I) or formulations and / or combinations comprising them according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide the plants with new traits or to modify already existing traits.

[0442] The term "crop plants" as used herein also includes (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide the plants with new traits or to modify already existing traits.

[0443] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques to generate mutations at specific loci in the plant genome. Targeted mutagenesis techniques often use oligonucleotides or proteins like CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases to achieve targeted effects.

[0444] Genetic engineering usually uses recombinant DNA technology to produce modifications in plant genomes, and such modifications can not be easily obtained by hybridization, mutagenesis or natural recombination under natural environments. Typically, one or more genes are integrated into the genome of plants to increase traits or improve traits. These integrated genes are also referred to as transgenic in the art, and the plants comprising such transgenic are referred to as transgenic plants. The plant transformation process usually produces several transformation events, which are different on the genomic loci of transgenics that have been integrated therein. Plants comprising specific transgenics on specific genomic loci are usually described as comprising specific "events", which are referred to by specific event names. The traits introduced into plants or modified particularly include herbicide tolerance, insect resistance, the yield of improvement and tolerance to abiotic conditions such as drought.

[0445] Herbicide tolerance has been generated by the use of mutagenesis as well as by genetic engineering. Plants that have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those that may be named Commercially available plant varieties. However, most herbicide tolerance traits have been generated through the use of transgenics.

[0446] Herbicide tolerance has been developed to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors like isoxathiapiprolin and mesotrione.

[0447] Transgenics that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1 and aad-12, for dicamba tolerance: dmo, for benzonitrile herbicide tolerance: bxn, for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA, for ALS inhibitor herbicide tolerance: csr1-2, for HPPD inhibitor herbicide tolerance: hppdPF, W336 and avhppd-03.

[0448] Transgenic maize events comprising herbicide tolerance genes are, for example, but not exclusively, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0449] Transgenic soybean events comprising herbicide tolerance genes are, for example, but not exclusively, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, W62, W98, FG72 and CV127.

[0450] Transgenic cotton events comprising a herbicide tolerance gene are, for example, but not exclusively, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40.

[0451] Transgenic canola events comprising a herbicide tolerance gene are for example, but not exclusively, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0452] Insect resistance is mainly produced by transferring bacterial genes of insecticidal proteins into plants. The most commonly used transgenics are toxin genes of Bacillus species (Bacillus spec.) and synthetic variants thereof, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A (a), vip3Aa20. However, plant-derived genes are also transferred into other plants. In particular, genes encoding protease inhibitors, such as CpTI and pinII. Another method uses transgenics to produce double-stranded RNA in plants to target and lower insect genes. The example of this transgenic is dvsnf7.

[0453] Transgenic maize events comprising a gene for an insecticidal protein or double-stranded RNA are, for example, but not exclusively, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

[0454] Transgenic soybean events comprising a gene for an insecticidal protein are for example, but not exclusively, MON87701, MON87751 and DAS-81419.

[0455] Transgenic cotton events comprising a gene for an insecticidal protein are, for example, but not exclusively, 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.

[0456] Increased yield is achieved by increasing ear biomass using the transgene athb17 present in maize event MON87403, or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0457] Crops containing improved oil content have been produced by using the following transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[0458] Tolerance to abiotic conditions, in particular drought tolerance, has been demonstrated through the use of the transgene cspB contained in maize event MON87460 and through the use of the transgene cspB contained in soybean event The included transgenic Hahb-4 was produced.

[0459] Traits are usually combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combinations of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different species of insects, in particular tolerance to Lepidoptera and Coleoptera, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield and a combination of herbicide tolerance and tolerance to abiotic conditions.

[0460] Plants containing single or stacked traits and genes and events providing these traits are well known in the art. For example, detailed information on mutagenic or integrated genes and corresponding events can be obtained from the International Service for the Application of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / www.isaaa.org / gmapprovaldatabase). http: / / cera-gmc.org / GMCropDatabase )'s website and patent applications like EP3028573 and WO2017 / 011288.

[0461] The use of compounds with formula (I) according to the present invention or formulations or combinations comprising them on crops may result in a unique effect on crops comprising a certain gene or event. These effects may relate to changes in growth behavior or altered resistance to biological or abiotic stress factors. Such effects may particularly include increased yield, increased resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasmas, viruses or viroid pathogens and early growth potential (earlyvigor), precocious or delayed maturity, cold or heat tolerance and altered amino acid or fatty acid profiles or content.

[0462] Furthermore, plants containing modified amounts of components or novel components by the use of recombinant DNA techniques, in particular to improve raw material production, such as potatoes producing increased amounts of amylopectin (e.g. Potatoes, BASF SE, Germany).

[0463] In addition, it has been found that the compounds of formula (I) according to the invention or preparations and / or combinations comprising them are also suitable for defoliation and / or dehydration of plant parts of crops such as cotton, potatoes, rape, sunflower, soybean or broad bean, in particular cotton. In this regard, preparations and / or combinations for dehydration and / or defoliation of crops, methods for preparing these preparations and / or combinations and methods for dehydrating and / or defoliating plants using compounds of formula (I) have been found.

[0464] As dehydrating agents, the compounds of formula (I) are particularly suitable for dehydrating the above-ground parts of crop plants such as potatoes, rape, sunflower and soybeans and also cereals. This enables fully mechanized harvesting of these important crop plants.

[0465] Also of economic interest is the promotion of the harvest of pernicious fruits, drupes and nuts of citrus fruits, olives and other species and varieties, which is made possible by concentrated cracking or reduced sticking to the tree within a certain time period. The same mechanism, i.e. the promotion of the development of abscissing tissue between the fruit part or the leaf part and the branch part of the plant, is also necessary for the controlled defoliation of useful plants, in particular cotton.

[0466] Furthermore, the shortening of the time interval between maturity of individual cotton plants results in improved fiber quality after harvest.

[0467] Furthermore, the present invention relates to compounds (I) per se, insofar as they are novel.

[0468] In one embodiment, the present invention relates to a compound having formula (I), an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof

[0469]

[0470] Where R 1 To R 9 has one of the general or preferred meanings given above,

[0471] Except for the following compounds (I), wherein:

[0472] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R5 It is Cl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), 2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-O-), 3,5-dimethyl-2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -C(CH3)=CH-CH(CH3)-O-), oxathiolane-2,2-diyl (ie, R 7 and R 8 Together, they form a bridging group -S-CH2-CH2-O-), 1,3-dioxolane-5,5-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-O-CH2-O-), 3-methyl-4,5-dihydroisoxazole-5,5-diyl (ie, R 7 and R 8 together to form a bridging group -CH2-C(CH3)=NO-), or

[0473] And R 9 is hydrogen or ethyl;

[0474] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form 1-tert-butoxycarbonyl-pyrrolidine-2,2-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-CH2-CH2-N(-C(O)-OC(CH3)3)-), and R 9 It is ethyl;

[0475] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 is F or Cl, R 7 and R 8Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-) or 2,5-dihydrothiophene-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-S-), and R 9 is hydrogen or methyl;

[0476] -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It's F, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-), and R 9 is hydrogen or ethyl;

[0477] -R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-), and R 9 is tert-butyl;

[0478] -R 1 is hydrogen or methyl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-3,3-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-O-CH2-), and R 9 is hydrogen or methyl; and

[0479] -R 7 and R 8 Together with the carbon atoms to which they are bonded, they form tetrahydropyran-4,4-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-CH2-CH2), and R 9 is hydrogen or ethyl;

[0480] And in addition to the following compound (I):

[0481] -2-[(3-fluoro-5-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0482] -2-[(3-bromophenyl)carbamoyl]oxolane-2-carboxylic acid;

[0483] -2-[(4-tert-butylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0484] -2-[(2,3-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0485] -2-[(3-bromo-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0486] -2-[(5-chloro-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0487] -2-[(4-trifluoromethoxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0488] -2-[(4-ethyl-3-fluorophenyl)carbamoyl]oxolane-2-carboxylic acid;

[0489] -2-[(3,5-difluoro-4-methoxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0490] -2-[(3-chloro-4-(2-methylpropyloxy)phenyl)carbamoyl]oxolane-2-carboxylic acid;

[0491] -2-[(4-hydroxy-2-methyl-5-(1-methylethyl)phenyl)carbamoyl]oxolane-2-carboxylic acid;

[0492] -2-[(4-hydroxy-2,3,5-trimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0493] -2-[(3-hydroxy-2,4-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0494] -2-[(5-ethyl-2-hydroxyphenyl)carbamoyl]oxolane-2-carboxylic acid;

[0495] -3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid as the compound having formula (I); and

[0496] -2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester.

[0497] More preferably, in the compound (I) according to the present invention, R 1 To R 8 has one of the general or preferred meanings given above, and

[0498] R 9 is n-propyl, isopropyl, n-butyl, sec-butyl (= 2-butyl), isobutyl (= 2-methylpropyl), (C5-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or phenyl-(C1-C3)-alkyl, wherein the last six radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; or

[0499] R 9 is (C1-C2)-alkyl, which is substituted by m1 groups selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein

[0500] R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy;

[0501] Each m is independently 0, 1, 2, 3, 4 or 5; and

[0502] m1 is 1, 2, 3, 4, or 5.

[0503] In particular, in the compounds (I) according to the present invention, R 1 To R 8has one of the general or preferred meanings given above, and

[0504] R 9 is composed of m1 groups R 9a substituted (C1-C6)-alkyl; (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl,

[0505] The last four radicals are each represented by m radicals R 9a replace;

[0506] Each R 9a are independently selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members;

[0507] R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy;

[0508] Each m is independently 0, 1, 2, 3, 4 or 5; and

[0509] m1 is 1, 2, 3, 4, or 5.

[0510] More particularly, in the compound (I) according to the present invention,

[0511] R 9 is composed of m1 groups R 9a substituted (C1-C4)-alkyl; (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl; and

[0512] Each R 9a is independently selected from the group consisting of fluorine, chlorine, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members (wherein the 5-membered heteroaromatic ring is preferably furanyl).

[0513] Even more particularly, in compounds (I) according to the invention, R 9 is (C1-C4)-alkyl which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members (wherein the 5-membered heteroaromatic ring is preferably furanyl); or R 9 It is (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl.

[0514] Specifically, in the compound (I) according to the present invention, R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio, and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

[0515] Specifically, the substituents in the compound (I) according to the present invention have the following meanings:

[0516] R 1 It is hydrogen;

[0517] R 2 It is hydrogen;

[0518] R 3 It is a halogen;

[0519] R 4 It is hydrogen;

[0520] R 5 It is a halogen;

[0521] R 6 It is hydrogen;

[0522] R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R bsubstituted, wherein n is 0, 1 or 2; or

[0523] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; wherein

[0524] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b Forming a methylene group (=CH2); and

[0525] R 9 is as defined above;

[0526] In particular, R 9 is (C1-C4)-alkyl which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members (wherein the 5-membered heteroaromatic ring is preferably furanyl); or R 9 is (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl;

[0527] Specifically, R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio, and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

[0528] In this context, preferably, R 7 and R 8Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5-, 6-, 7- or 8-membered monocyclic or bicyclic heterocyclic ring W which, in addition to this carbon atom, contains q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, one of the carbon ring atoms carries p oxo groups, and wherein the ring is substituted by methylene (═CH 2 ); wherein q, u, v and w are as defined above. More preferably, wherein R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated 5- or 6-membered, preferably 5-membered, monocyclic heterocycle W which, in addition to this carbon atom, contains 3 or 4 carbon atoms and 1 oxygen atom as ring members and in which the ring is substituted by methylene (═CH 2 ).

[0529] In more specific embodiments, the substituents in compound (I) according to the present invention have the following meanings:

[0530] R 1 It is hydrogen;

[0531] R 2 It is hydrogen;

[0532] R 3 It is a halogen;

[0533] R 4 It is hydrogen;

[0534] R 5 It is a halogen;

[0535] R 6 It is hydrogen;

[0536] R 7 and R 8 together with the carbon atom to which they are bound, form a saturated 5- or 6-membered, preferably 5-membered, monocyclic heterocyclic ring W which, in addition to this carbon atom, contains 3 or 4 carbon atoms and 1 oxygen atom as ring members and in which the ring is substituted by a methylene group (═CH 2 ); and

[0537] R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; and is preferably hydrogen.

[0538] In an even more specific embodiment, the substituents in compounds (I) according to the invention have the following meanings:

[0539] R 1 It is hydrogen;

[0540] R 2 It is hydrogen;

[0541] R 3 It is a halogen;

[0542] R 4 It is hydrogen;

[0543] R 5 It is a halogen;

[0544] R 6 It is hydrogen;

[0545] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein

[0546] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and

[0547] R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

[0548] In very specific embodiments, the substituents in the compounds (I) according to the invention have the following meanings:

[0549] R 1 It is hydrogen;

[0550] R 2 It is hydrogen;

[0551] R 3 It is a halogen;

[0552] R 4 It is hydrogen;

[0553] R 5 It is a halogen;

[0554] R 6 It is hydrogen;

[0555] R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated 4-membered monocyclic heterocycle W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, or a partially unsaturated 5-membered monocyclic heterocycle W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein

[0556] Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and

[0557] R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

[0558] Examples

[0559] A Chemical Example

[0560] abbreviation

[0561] DMAP 4-(dimethylamino)-pyridine

[0562] EtOAc Ethyl acetate

[0563] EtOH

[0564] LDA Lithium diisopropylamide

[0565] MeCN Acetonitrile

[0566] OAc acetate

[0567] PE Petroleum Ether

[0568] THF Tetrahydrofuran

[0569] Chemical bonds drawn as bars in chemical formulas indicate relative stereochemistry on the ring system.

[0570] Example 1:

[0571] Synthesis of ethyl 5-[(3,5-dichlorophenyl)carbamoyl]-2H-furan-5-carboxylate (Compound I.1)

[0572]

[0573] At 20°C, to a mixture of diethyl malonate (1) (50g, 310mmol) (CAS [53051-81-3]) and triethylamine (75g, 744mmol) in MeCN (500ml) was added 4-acetamidobenzenesulfonyl azide (2) (p-ABSA, 12g, 465mmol) (CAS [2158-14-7]). The mixture was stirred at 20°C for 16h. The reactants were filtered and the filtrate was concentrated. Dichloromethane (100mL) was added to the filtrate. The mixture was filtered and the filtrate was concentrated. The crude product was purified by HPLC (EtOAc / PE=0% to 100%) to give diethyl 2-diazomalonate (2) (62g, quantitative) as a yellow oil. 1 H NMR (400 MHz, CHLOROFORM-d) δ 4.31 (q, 4H), 1.32 (t, 6H).

[0574]

[0575] To a solution of diethyl 2-diazomalonate (3) (62 g, 330 mmol) and propargyl alcohol (4) (18.5 g, 330 mmol) (CAS [107-19-7]) in toluene (600 ml) was added Rh2(OAc)4 (1.3 g, 2.9 mmol) (CAS [15956-28-2]) at 20°C. The mixture was stirred at 60°C for 1 h. The reaction was filtered and the filtrate was concentrated. The crude product was purified by HPLC (EtOAc / PE = 0% to 100%) to give diethyl 2-prop-2-ynyloxymalonate (5) (53 g, 80% over two steps) as a yellow oil. 1 H NMR (400 MHz, CHLOROFORM-d) δ 4.82-4.80 (s, 1H), 4.41 (d, 2H), 4.28 (m, 4H), 2.53 (t, 1H), 1.31 (t, 6H).

[0576]

[0577] At 20 ° C, KOH (7.85 g, 140 mmol) was added in batches to a solution of diethyl 2-prop-2-ynyloxymalonate (5) (30 g, 140 mmol) in EtOH / H2O (200 / 200 mL). The mixture was stirred at 20 ° C for 16 h. The mixture was quenched with H2O, adjusted to pH=3 with 6N HCl, and extracted with EtOAc. The combined organics were washed with brine, dried and concentrated to give 2-ethoxycarbonylhydrofuran-2-carboxylic acid (6) (20 g, 77%) as a yellow oil. 1 H NMR (400 MHz, CHLOROFORM-d) δ 6.23 (m, 1H), 6.02 (tdd, 1H), 4.93 (m, 1H), 4.87 (m, 1H), 4.29 (q, 2H), 1.32 (t, 3H).

[0578]

[0579] Aniline 7 (50 mL, 1.2 M) was added to a solution of 2-ethoxycarbonylhydrofuran-2-carboxylic acid (12 g, 64 mmol) in dimethylformamide (DMF). HATU (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]) (29.4 g, 77.4 mmol) was added to the resulting solution, followed by diisopropylethylamine (33 mL, 194 mmol). The resulting reaction mixture was stirred at room temperature overnight. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as a solvent to produce 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid ethyl ester (Compound I.1) (21 g, 99%) as a yellow solid. 1 H NMR (400 MHz, CHLOROFORM-d) δ 8.32 (br s, 1H), 7.56 (d, J=1.8 Hz, 2H), 7.14 (m, 1H), 6.20 (m, 1H), 6.01 (m, 1H), 4.89-4.86 (m, 1H), 4.81 (s, 1H), 4.28 (m, 4H), 1.32 (t, 3H).

[0580] Example 2:

[0581] Synthesis of 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Compound I.2)

[0582]

[0583] At 20 ° C, to 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid ethyl ester (Compound I.1) (1.33 g, 4.03 mmol) in EtOH / H2O (40 / 20 mL) was added KOH (452 ​​mg, 8.06 mmol) in batches. The mixture was stirred at 20 ° C for 16 h. The mixture was quenched with H2O, adjusted to pH = 3 with 6N HCl, and extracted with EtOAc. The combined organics were washed with brine, dried and concentrated to give 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Compound I.2) (950 mg, 78%) as a yellow oil. 1 H NMR (400 MHz, CHLOROFORM-d) δ 8.72 (s, 1H), 7.54 (m, 2H), 7.20 (m, 1H), 6.26 (m, 1H), 6.10 (m, 1H), 5.15 (m, 1H), 5.06 (m, 1H).

[0584] Example 3:

[0585] Synthesis of ethyl 5-[(3,5-difluorophenyl)carbamoyl]-2H-furan-5-carboxylate (Compound I.20)

[0586]

[0587] According to Example 2, to a solution of 2-ethoxycarbonylhydrofuran-2-carboxylic acid (6) (7.1 g, 38 mmol) in dimethylformamide (DMF) (50 mL, 0.76 M) was added aniline 8 (4.9 g, 38 mmol). To the resulting solution was added HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]) (17.4 g, 45.8 mmol) followed by diisopropylethylamine (19.5 mL, 114 mmol). The resulting reaction mixture was stirred at room temperature overnight. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid ethyl ester (Compound I.20) (8.4 g, 74%) as a yellow to brown oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.61 (s, 1H), 7.25–7.14 (m, 2H), 6.58 (tt, J = 8.9, 2.3 Hz, 1H), 6.26–6.11 (m, 2H), 4.94 (dd, J = 2.2, 1.3 Hz, 2H), 4.27 (q, J = 7.1 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H).

[0588] Example 4:

[0589] Synthesis of 5-[(3,5-difluorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Compound I.7)

[0590]

[0591] At 20 ° C, to 5- [(3,5-difluorophenyl) carbamoyl] -hydrofuran-5-carboxylic acid ethyl ester (compound I.20) (8.4 g, 28 mmol) in a 1: 1 mixture (50 mL) of THF and water, LiOH (1.35 g, 56.5 mmol) was added in batches. The mixture was stirred at room temperature overnight. The mixture was quenched with H2O, adjusted to pH = 3 with 6N HCl, and extracted with EtOAc. The combined organics were washed with brine, dried and concentrated to give 5- [(3,5-difluorophenyl) carbamoyl] -hydrofuran-5-carboxylic acid (compound I.7) (7 g, 92%) as a colorless liquid. 1 H NMR (400 MHz, CHLOROFORM-d) δ 8.75 (s, 1H), 7.18 (dd, J = 8.3, 2.2 Hz, 2H), 6.75–6.59 (m, 1H), 6.26 (dt, J = 6.1, 1.6 Hz, 1H), 6.09 (dt, J = 6.0, 2.4 Hz, 1H), 5.23–5.12 (m, 1H), 5.05 (dt, J = 13.5, 2.0 Hz, 1H).

[0592] Example 5:

[0593] Synthesis of cyclopropylmethyl 5-[(3,5-dichlorophenyl)carbamoyl]-2H-furan-5-carboxylate (Compound I.18):

[0594]

[0595] To a solution of 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (0.10 mg, 0.37 mmol) in dichloromethane (3 mL, 0.1 M) was then added DMAP (45 mg, 0.37 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (214 mg, 1.11 mmol) and cyclopropylmethanol (27 mg, 0.37 mmol). After stirring for 18 h, the reaction was quenched with 1N HCl (1 mL). The organic layer was separated and washed with 1N HCl (2x), then dried over sodium sulfate. The filtrate was concentrated to provide compound I.18 (71 mg, 59%) as a colorless viscous oil. 1 H NMR (400MHz, chloroform-d) δ8.59(s,1H),7.25–7.14(m,2H),6.59(tt,J=8.9,2.3Hz,1H),6.26-6.14(m,2H),4.95(d t, J=2.3, 1.6Hz, 2H), 4.05 (dd, J=7.3, 0.9Hz, 2H), 1.24-1.10 (m, 1H), 0.64-0.49 (m, 2H), 0.35-0.26 (m, 2H).

[0596] Example 6:

[0597] Synthesis of ethyl 2-[(3,5-difluorophenyl)carbamoyl]-3H-furan-2-carboxylate (Compound I.25)

[0598]

[0599] At 20 ° C, Zn (78.4 g, 1225 mmol) was added to a solution of ethyl glyoxylate (9) (50 g, 490 mmol) and propargyl bromide (10) (116 g, 980 mmol) in THF (200 mL). The mixture was initially stirred at room temperature and heated to 80 ° C in a time period of 1 h. After cooling to room temperature, the mixture was filtered. The filtrate was quenched with HCl (2N, 300 mL) and extracted with EtOAc (100 mL x 3). The combined organic matter was washed with brine, dried and concentrated, and purified by column chromatography (hexane / EtOAc=100:0 to 0:100) to obtain 2-hydroxypent-4-ynoic acid ethyl ester (11) (100 g, 72.2% yield) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ=4.40 (t, J=4.9Hz, 1H), 4.37-4.26 (m, 2H), 2.80-2.65 (m, 2H), 2.07 (t, J=2.6Hz, 1H), 1.33 (t, J=7.1Hz, 3H).

[0600]

[0601] At room temperature, Ag2O (44.5g, 193mmol) and triethylamine (39.1g, 387mmol) were added to a mixture of 2-hydroxypent-4-ynoic acid ethyl ester (55g, 387mmol) in acetone (1100ml). After stirring the reactant for 2h at 50°C, the suspension was filtered, and the filtrate was quenched with water (1L). The aqueous layer was extracted with methyl tert-butyl ether (3x 500mL). The combined ether was washed with brine, dried and concentrated. The crude product was purified by flash column chromatography (methyl tert-butyl ether) and distilled at 75°C at 20 torr to obtain 2,3-dihydrofuran-2-carboxylic acid ethyl ester (12) (15.8g, 29%) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ = 6.38 (q, J = 2.5Hz, 1H), 4.99-4.93 (m, 1H), 4.26 (q, J = 7.1H z, 2H), 3.04-2.94 (m, 1H), 2.79 (tdd, J = 2.4, 7.3, 15.6Hz, 1H), 1.31 (t, J = 7.1Hz, 3H).

[0602]

[0603] At -78 ° C, to a solution of LDA (29 ml, 59.1 mmol) in THF (60 mL), 2,3-dihydrofuran-2-carboxylic acid ethyl ester (12) (6.0 g, 42 mmol) in THF (60 ml) was added within 5 min, and stirred at -78 ° C for 10 min. CO2 (dry ice) was added and stirred at -78 ° C for 1 h. The mixture was quenched with HCl (1N, 150 ml) and extracted with ethyl acetate (100 mL x 2). The combined organics were washed with brine, dried and concentrated to give 2-ethoxycarbonyl-3H-furan-2-carboxylic acid (13) (8 g, 100%) as a yellow oil. Based on instability, the crude product was used in the next step without further purification.

[0604]

[0605] At 0 ° C, T3P (41.0 g, 64.5 mmol) was added dropwise to a solution of 2-ethoxycarbonyl-3H-furan-2-carboxylic acid (13) (8 g, 43 mmol), aniline 8 (8.32 g, 64.5 mmol) and triethylamine (17.43 g, 172 mmol) in THF (20 mL). After stirring for 16 h, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (100 mL x 3). The combined organic layer was washed with brine (200 mL), dried and concentrated to give a crude product, which was purified by column chromatography (hexane / ethyl acetate = 100: 0 to 7: 3) to give 2- [(3,5-difluorophenyl) carbamoyl] -3H-furan-2-carboxylic acid ethyl ester (compound I.25) (6 g, 47% yield) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ = 8.49 (br s,1H),7.26-7.19(m,2H),6.62(tt,J=2.3,8.9Hz,1H),6.39(q,J=2.5Hz,1H),5.12(q,J=2.6Hz,1H), 4.42-4.21(m,2H),3.49(td,J=2.5,16.6Hz,1H),3.23(td,J=2.4,16.7Hz,1H),1.33(t,J=7.2Hz,3H).

[0606] Example 7:

[0607] Synthesis of 2-[(3,5-difluorophenyl)carbamoyl]-3H-furan-2-carboxylate (Compound I.26)

[0608]

[0609] At 0 ° C, LiOH · H2O (0.84 g, 21 mmol) in water (8 mL) was added dropwise to a solution of compound I.25 (4.0 g, 14 mmol) in THF (40 mL). After stirring at room temperature for 3 h, the mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL). The aqueous phase was adjusted to pH = 3 with 6N HCl and extracted with ethyl acetate (50 mL x 3). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to give a crude product (2.7 g, 75%). In order to analyze the data, 600 mg of the crude product was purified by preparative HPLC (NH4HCO3, MeCN-H2O) to give 2-[(3,5-difluorophenyl)carbamoyl]-3H-furan-2-carboxylate (compound I.26) (337 mg): 1H-NMR (400MHz, CDCl3): δ=7.63-7.45(m,2H), 6.91-6.79(m,1H), 6.39(q,J=2.3Hz,1H), 4.86(q,J=2.4Hz,1H), 3.11-2.90(m,2H).

[0610] Example 8:

[0611] Synthesis of methyl 3-[(3,5-difluorophenyl)carbamoyl]-2H-furan-3-carboxylate (Compound I.27)

[0612]

[0613] At 0 ° C, NaHCO (1.95 g, 23.26 mmol) and formaldehyde (37% in water) (20.7 g, 256 mmol) were added to a solution of 2-allylmalonate (40 g, 232.56 mmol) in ethanol (160 mL) and water (80 mL), and stirred for 16 h at 15 ° C. The reaction mixture was poured into ice water (200 mL) and extracted with EtOAc (200 mL x 3). The organic phase was washed with brine, dried over sodium sulfate, concentrated and purified by column chromatography (hexane / ethyl acetate=100:0 to 6:4) to obtain 2-allyl-2-hydroxy-malonate (39 g, 83%) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ = 5.81-5.66 (m, 1H), 5.21-5.10 (m, 2H), 3.95 (d, J = 6.8Hz, 2H), 3.78 (s, 6H), 2.70 (d, J = 7.4Hz, 2H), 2.54 (t, J = 6.9Hz, 1H).

[0614]

[0615] At -78 ° C, ozone was bubbled through a solution of 2-allyl-2-hydroxy-malonic acid dimethyl ester (39 g, 193 mmol) in dichloromethane (390 mL) and methanol (39 mL) for 3 h. After adding dimethyl sulfide, the reaction mixture was stirred at 15 ° C for 16 h. The reaction mixture was concentrated and purified by column chromatography (hexane / ethyl acetate = 100: 0 to 60: 40) to give 5-hydroxytetrahydrofuran-3,3-dicarboxylic acid dimethyl ester (16) (35 g, 88%) as a yellow oil. 1H-NMR (400MHz, CDCl3): δ = 5.57 (dt, J = 1.4, 5.5Hz, 1H), 4.48 (d, J = 9.4Hz, 1H), 4.31 (d, J = 9.3H z,1H),3.80(s,3H),3.77(s,3H),3.51(d,J=5.9Hz,1H),2.70-2.62(m,1H),2.56-2.49(m,1H).

[0616]

[0617] At 0 ° C, triethylamine (14.8 g, 147 mmol) and methanesulfonyl chloride [CAS: 124-63-0] (8.38 g, 73.53 mmol) were added dropwise to a solution of 5-hydroxytetrahydrofuran-3,3-dicarboxylic acid dimethyl ester (16) (10 g, 49 mmol) in dichloromethane (100 mL) at 0 ° C. After stirring for 3 h at the same temperature, the mixture was stirred at 70 ° C for 16 h. The reaction mixture was poured into ice water (100 mL) and extracted with ethyl acetate (100 mL x 3). The organic phase was washed with brine, dried over sodium sulfate, concentrated and purified by column chromatography (hexane / ethyl acetate = 100: 0 to 60: 40) to give 2H-furan-3,3-dicarboxylic acid dimethyl ester (17) (5.84 g, 64%) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ=6.47 (d, J=2.6Hz, 1H), 5.19 (d, J=2.6Hz, 1H), 4.75 (s, 2H), 3.77 (s, 6H).

[0618]

[0619] According to Example 3, to a solution of dimethyl 2H-furan-3,3-dicarboxylate (17) (3.7 g, 19.9 mmol) in methanol (20 mL) was added dropwise LiOH (14.82 g) in water (20 mL) at 0°C. After stirring at 15°C for 16 h, the reaction mixture was lyophilized to give 3-methoxycarbonyl-2H-furan-3-carboxylic acid (3.7 g, 100%) as a white amorphous solid. The crude product was used without further purification. 1 H-NMR (400MHz, CDCl3): δ=6.37 (d, J=2.6Hz, 1H), 5.21 (d, J=2.6Hz, 1H), 4.72 (d, J=9.4Hz, 1H), 4.61 (d, J=9.4Hz, 1H), 3.69 (s, 3H).

[0620]

[0621] According to Example 1, aniline 8 (40 mL, 0.55 M) was added to a solution of 3-ethoxycarbonyl-2H-furan-3-carboxylic acid (3.7 g, 22 mmol) in dimethylformamide (DMF). HATU (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]) (16 g, 43 mmol) was added to the resulting solution, followed by triethylamine (10.9 g, 108 mmol). The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water (100 mL) and extracted with ethyl acetate (100 mL x 3). The organic phase was washed with brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (hexane / ethyl acetate = 100:0 to 60:40) to give methyl 3-[(3,5-difluorophenyl)carbamoyl]-2H-furan-3-carboxylate (Compound I.27) (6.8 g, quantitative crude yield) as a yellow oil. 1 H NMR (400MHz, chloroform-d) δ = 8.18 (br s,1H),7.20-7.12(m,2H),6.67(d,J=2.6Hz,1H),6.60(tt,J=2.3,8.9Hz,1H),5. 24(d,J=2.6Hz,1H), 5.07(d,J=10.3Hz,1H), 4.83(d,J=10.3Hz,1H), 3.84(s,3H).

[0622] Example 9:

[0623] Synthesis of 3-[(3,5-difluorophenyl)carbamoyl]-2H-furan-3-carboxylate (Compound I.28)

[0624]

[0625] According to 2, to a solution of 3-[(3,5-difluorophenyl)carbamoyl]-2H-furan-3-carboxylic acid methyl ester (compound I.27) (1.0 g, 3.5 mmol) in methanol (6 mL) was added dropwise LiOH (223 mg) in water (6 mL) at 0° C. After stirring at 15° C. for 16 h, the reaction mixture was purified by preparative HPLC (NH3`H2O) to give 3-methoxycarbonyl-2H-furan-3-carboxylic acid (200 mg, 21%) as a white amorphous solid. 1H NMR (400 MHz, methanol-d) δ = 7.33-7.23 (m, 2H), 6.62 (tt, J = 2.4, 9.1 Hz, 1H), 6.42 (d, J = 2.6 Hz, 1H), 5.33 (d, J = 2.6 Hz, 1H), 4.93-4.90 (m, 1H), 4.83-4.80 (m, 1H).

[0626] Example 10:

[0627] Synthesis of ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (Compound II.1)

[0628]

[0629] A solution of lithium hydroxide (118 mg, 4.95 mmol) in water was added dropwise to a mixture of 2,2-diethoxyoxetane-2,2-dicarboxylate (19) (CAS [1384465-73-9]) (1000 mg, 4.95 mmol), tetrahydrofuran (THF) (50 ml) and water (50 ml), and the reaction mixture was stirred at room temperature overnight. THF was evaporated in vacuo and the remainder was washed with methyl tert-butyl ether. The aqueous solution was concentrated in vacuo and the remainder was dried to give the product (20) (740 mg, 86% yield). 1 H NMR (500 MHz, deuterium oxide) δ = 4.55 (t, 2H), 4.28 (m, 2H), 3.13 (m, 1H), 2.91 (m, 1H), 1.29 (t, 3H).

[0630]

[0631] To a solution of ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (20) (3.52 g, 19.6 mmol) in dimethylformamide (DMF) was added aniline 7 (3.17 g, 19.6 mmol). To the resulting solution was added HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]) (8.18 g, 21.5 mmol) and then diisopropylethylamine (16.6 mL). The resulting reaction mixture was stirred at room temperature overnight. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to yield ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (Compound II.1) (1.6 g, 26%). 1 H NMR (500 MHz, CHLOROFORM-d) δ=8.71(s,1H),7.61(d,2H),7.16(d,1H),4.74(dt,1H),4.66(m,1H),4.31(q,2H),3.42(ddd,1H),2.95(ddd,1H),1.32(t,3H).

[0632] Example 11:

[0633] Synthesis of 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylic acid (Compound II.18)

[0634]

[0635] A solution of lithium hydroxide (23 mg, 3.8 mmol) in water was added dropwise to a mixture of ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (Compound II.1) (150 mg, 0.472 mmol), tetrahydrofuran (THF) (10 ml) and water (10 ml), and the reaction mixture was stirred at room temperature overnight. THF was evaporated in a vacuum and the remainder was washed with methyl tert-butyl ether (MTBE). The aqueous solution was concentrated in a vacuum and the residue was dried to give 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylic acid (Compound II.18) (130 mg, 95% yield). 1 H NMR (500 MHz, methanol-d4) δ = 7.76 (d, 2H), 7.21 (t, 1H), 6.56 (m, 1H), 4.67 (t, 2H), 3.31 (m, 1H), 2.94 (dt, 1H).

[0636] Example 12:

[0637] Synthesis of methyl 3-[(3,5-difluorophenyl)carbamoyl]oxetane-3-carboxylate (Compound II.19)

[0638]

[0639] According to Example 6, at 0 ° C, 3-methoxycarbonyloxetane-3-carboxylic acid (21) [CAS: 1395668-39-9] (400 mg, 2.50 mmol), aniline 7 (322 g, 2.50 mmol) and triethylamine (1.04 mL, 7.5 mmol) in THF (5 mL, 0.5 M) solution was added dropwise T3P (50%, in DMF, 2.4 mL, 4.0 mmol). After stirring at room temperature for 3 h, the mixture was quenched with brine (10 mL) and extracted with ethyl acetate (10 mL x 2). The combined organic layers were concentrated and purified by preparative HPLC (water / acetonitrile) to give 3-[(3,5-difluorophenyl)carbamoyl]oxetane-3-carboxylic acid methyl ester (Compound II.19) (590 mg, 87%) as a yellow oil. 1 H-NMR (400MHz, CDCl3): δ = 8.77 (s, 1H), 7.24–7.13 (m, 2H), 6.60 (tt, J = 8.9, 2.4Hz, 1H), 5.13 (d, J = 6.2Hz, 2H), 4.98 (d, J = 6.2Hz, 2H), 3.95 (s, 3H).

[0640] Example 13:

[0641] Synthesis of 3-[(3,5-difluorophenyl)carbamoyl]oxetane-3-carboxylic acid (Compound II.20)

[0642]

[0643] According to Example 3, to a solution of methyl 3-[(3,5-difluorophenyl)carbamoyl]oxetane-3-carboxylate (Compound II.19) (0.55 mg, 2.0 mmol) in a 1:1 mixture (30 mL) of THF and water, LiOH (97 mg, 4.1 mmol) was added. The mixture was stirred at room temperature for 2 h. After the reaction mixture was concentrated under reduced pressure, the residue was washed with ethyl acetate. After the pH value of the aqueous residue was adjusted to 3 with 6N HCl, the aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated to give crude 3-[(3,5-difluorophenyl)carbamoyl]oxetane-3-carboxylic acid (Compound II.20) (450 mg, 88%) as a colorless amorphous solid.1 H NMR (400MHz, THF-d) δ = 9.45 (s, 1H), 7.35-7.27 (m, 2H), 6.65 (tt, J = 9.1, 2.3Hz, 1H), 4.95 (d, J = 6.0Hz, 2H), 4.87 (d, J = 6.0Hz, 2H).

[0644] High performance liquid chromatography: HPLC-column Kinetex XB C18 1,7μ (50 x 2,1 mm); eluent: acetonitrile / water+0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml / min in 1.5 min).

[0645] Analogously to the above examples, starting from commercially available diesters and using commercially available amines, the following compounds of formula (I) were prepared, wherein R 1 is hydrogen, and W is composed of R 7 and R 8 Together with the carbon atoms to which they are bonded, they form:

[0646]

[0647] Table 2

[0648] HPLC / MS = mass-to-charge ratio

[0649]

[0650]

[0651]

[0652]

[0653] Table 3

[0654] HPLC / MS = mass-to-charge ratio

[0655]

[0656]

[0657]

[0658] Table 4

[0659] HPLC / MS = mass-to-charge ratio

[0660]

[0661] Table 5

[0662] HPLC / MS = mass-to-charge ratio

[0663]

[0664] Table 6

[0665] HPLC / MS = mass-to-charge ratio

[0666]

[0667] B Application Examples

[0668] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiment:

[0669] The culture containers used were plastic pots containing sandy loam with about 3.0% humus as a substrate. The seeds of the test plants were sown individually for each species.

[0670] For the pre-emergence treatment, the active ingredient suspended or emulsified in water is applied directly after sowing with the aid of a fine dispensing nozzle. The containers are gently irrigated to promote germination and growth and then covered with a transparent plastic cover until the test plants have rooted. This covering allows the test plants to germinate uniformly, unless they have been damaged by the action of the active ingredient.

[0671] For the post-emergence treatment, the test plants are first grown to a height of 3 to 15 cm, depending on the plant habit, and then treated only with the active ingredient suspended or emulsified in water. For this purpose, the test plants are sown directly and grown in the same container, or first grown individually as seedlings and transplanted into test containers a few days before treatment.

[0672] Depending on the species, the test plants were maintained at 10°C-25°C or 20°C-35°C, respectively.

[0673] The test period lasts from 2 to 4 weeks. During this time, the test plants are cared for and their response to the individual treatments is evaluated.

[0674] Evaluation was performed using a scale of 0 to 100. 100 means that no test plant emerged, or at least the above-ground part was completely destroyed, and 0 means no damage, or normal growth process. Values ​​of 70 to <90 were given for good herbicidal activity and values ​​of 90 to 100 were given for very good herbicidal activity.

[0675] The test plants used in the greenhouse experiments belonged to the following species:

[0676] Bayer Code scientific name ALOMY Alopecurus sibiricus AMARE Amaranthus retroflexus APESV Apiraea AVEFA Wild Oats DIGSA Crataegus ECHCG Barnyard grass LOLMU Lolium multiflorum SETVI Setaria SETFA giant foxtail

[0677] At an application rate of 0.125 kg / ha, applied by pre-emergence method:

[0678] Compound I.6 showed good herbicidal activity against AMARE

[0679] Compound I.6 showed good herbicidal activity against APESV

[0680] At an application rate of 0.250 kg / ha, applied by pre-emergence method:

[0681] Compound II.8 showed good herbicidal activity against AMARE

[0682] Compounds I.1, I.2, I.5, and II.5 showed good herbicidal activity against APESV

[0683] Compounds I.10 and I.25 showed good herbicidal activity against LOLMU

[0684] At an application rate of 0.500 kg / ha, applied by pre-emergence method:

[0685] Compounds I.8, I.14, and I.16 showed good herbicidal activity against AMARE

[0686] Compound I.7 showed very good herbicidal activity against APESV

[0687] Compound I.7 showed good herbicidal activity against ECHCG

[0688] Compounds I.8, I.9, I.12, I.13, I.18, and I.19 showed very good herbicidal activity against LOLMU

[0689] Compounds I.11, I.14, I.15, I.16, and I.17 showed good herbicidal activity against LOLMU

[0690] Compound I.7 showed good herbicidal activity against SETFA

[0691] Compound I.9 showed very good herbicidal activity against SETVI

[0692] Compounds I.14 and I.18 showed good herbicidal activity against SETVI

[0693] At an application rate of 1.000 kg / ha, applied by the pre-emergence method:

[0694] Compounds I.26 and II.1 showed very good herbicidal activity against AMARE

[0695] Compound II.1 showed good herbicidal activity against APESV

[0696] Compound I.26 showed very good herbicidal activity against DIGSA

[0697] Compound II.1 showed good herbicidal activity against ECHCG

[0698] Compound I.26 showed very good herbicidal activity against LOLMU

[0699] At an application rate of 0.250 kg / ha, applied by post-emergence method:

[0700] Compound I.25 showed very good herbicidal activity against ALOMY

[0701] Compounds I.1, I.10, and II.5 showed good herbicidal activity against ALOMY

[0702] Compounds I.25 and II.10 showed very good herbicidal activity against AMARE

[0703] Compounds I.4, II.4, II.6, II.7, II.8, II.9, II.11, II.12, II.15, II.16, and II.17 showed good herbicidal activity against AMARE

[0704] Compounds I.25, II.5, II.6, II.7, II.9, II.10, II.11, II.12, II.13, II.16, and II.17 showed very good herbicidal activity against AVEFA

[0705] Compounds I.1, I.2, I.10, II.8, II.14, and II.15 showed good herbicidal activity against AVEFA

[0706] Compounds I.25, II.7, II.8, II.10, II.11, II.12, II.13, II.14, II.15, II.16, and II.17 showed very good herbicidal activity against ECHCG

[0707] Compounds I.10, II.6, and II.9 showed good herbicidal activity against ECHCG

[0708] Compound II.5 showed very good herbicidal activity against SETVI

[0709] At an application rate of 0.500 kg / ha, applied by post-emergence method:

[0710] Compound I.7 showed very good herbicidal activity against ALOMY

[0711] Compounds I.13, I.16, I.17, and I.19 showed good herbicidal activity against ALOMY

[0712] Compounds I.8, I.12, I.14, and II.20 showed good herbicidal activity against AMARE

[0713] Compounds I.7, I.9, I.11, I.12, I.13, I.15, I.16, and I.18 showed very good herbicidal activity against AVEFA

[0714] Compounds I.8, I.14, I.17, and I.19 showed good herbicidal activity against AVEFA

[0715] Compounds I.7, I.14 and I.18 showed very good herbicidal activity against ECHCG

[0716] Compounds I.8, I.9, I.11, I.12, I.15, I.17, I.19, and II.20 showed good herbicidal activity against ECHCG

[0717] At an application rate of 1.000 kg / ha, applied by post-emergence method:

[0718] Compounds II.1 and II.2 showed very good herbicidal activity against AMARE

[0719] Compound I.26 showed good herbicidal activity against AMARE

[0720] Compound I.26 showed very good herbicidal activity against AVEFA

[0721] Compounds I.26, II.1, and II.2 showed very good herbicidal activity against ECHCG

[0722] Compounds II.1 and II.2 showed very good herbicidal activity against SETVI.

Claims

1. A compound of formula (I), its agriculturally acceptable salt, stereoisomer or tautomer for use in combating undesirable vegetation, in R 1 is hydrogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 2 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 3 is hydrogen, halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl; R 4 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)-halocycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 5 is hydrogen, halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl; R 6 is hydrogen, halogen, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5-, 6-, 7- or 8-membered monocyclic or bicyclic heterocyclic ring W which, in addition to this carbon atom, contains q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, one of the carbon ring atoms carries p oxo groups, and wherein the ring is surrounded by n radicals R b replace; R 9 is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or phenyl-(C1-C3)-alkyl, wherein the last six groups are each substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy; Each R b R is independently halogen, nitro, hydroxy, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl; or two R bonded to the same carbon atom b Together they form a methylene group (=CH2); Each m is independently 0, 1, 2, 3, 4 or 5; Each n is independently 0, 1 or 2; p is 0 or 1; q is 1, 2, 3, 4, 5, or 6; u is 0, 1, or 2; v is 0, 1, 2, or 3; w is 0, 1, or 2; The premise is that at least one of u, v and w is not 0.

2. The use according to claim 1, wherein One, two, three or all four of the following conditions a), b), c), d) apply: a) R 1 is hydrogen or (C1-C3)-alkyl; b) R 2 is hydrogen, halogen, or (C1-C3)-alkyl, and R 6 is hydrogen, halogen, or (C1-C3)-alkyl; c) R 3 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy, and R 5 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; d) R 4 is hydrogen or a halogen.

3. The use according to claim 2, wherein One, two, three or all four of the following conditions a), b), c), d) apply: a) R 1 It is hydrogen; b) R 2 is hydrogen, and R 6 It is hydrogen; c) R 3 is halogen or (C1-C3)-haloalkoxy, preferably halogen; and R 5 is hydrogen or halogen, preferably halogen; d) R 4 It's hydrogen.

4. The use according to any one of the preceding claims, wherein R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocycle W or a saturated or partially unsaturated 7- or 8-membered bicyclic heterocycle W, wherein ring W contains, in addition to this carbon atom, q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, wherein the sum of u, v and w is 1 or 2, and wherein ring W is surrounded by n radicals R b replace.

5. The use according to any one of the preceding claims, wherein u is 1 or 2, v is 0 and w is 0; or u is 1, v is 1 and w is 0; or u is 1, v is 0 and w is 1; or u is 0, v is 0 and w is 1.

6. The use according to any one of the preceding claims, wherein R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; Preferably, R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b Substitution, wherein n is 0 or 1.

7. The use according to any one of the preceding claims, wherein Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b A methylene group (=CH2) is formed.

8. The use according to any one of the preceding claims, wherein R 9 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or (C1-C4)-alkyl, which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein m is 1, 2 or 3.

9. The use according to claim 8, wherein R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl.

10. The use according to any one of the preceding claims, wherein These substituents have the following meanings: R 1 is hydrogen or (C1-C3)-alkyl; preferably hydrogen; R 2 is hydrogen, halogen or (C1-C3)-alkyl; R 3 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 4 is hydrogen or halogen; preferably hydrogen; R 5 is hydrogen, halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy or (C1-C3)-haloalkoxy; R 6 is hydrogen, halogen or (C1-C3)-alkyl; R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocycle W or a saturated or partially unsaturated 7- or 8-membered bicyclic heterocycle W, wherein ring W contains, in addition to this carbon atom, q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, wherein the sum of u, v and w is 1 or 2, and wherein ring W is surrounded by n radicals R b replace; R 9 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or (C1-C4)-alkyl, which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein m is 1, 2 or 3.

11. The use according to claim 10, wherein These substituents have the following meanings: R 1 It is hydrogen; R 2 It is hydrogen; R 3 is halogen or (C1-C3)-haloalkoxy; R 4 It is hydrogen; R 5 is hydrogen or a halogen; R 6 It is hydrogen; R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; wherein Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b Forming a methylene group (=CH2); and R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl; Where R 9 Preferred is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl.

12. The use according to claim 11, wherein These substituents have the following meanings: R 1 It is hydrogen; R 2 It is hydrogen; R 3 It is a halogen; R 4 It is hydrogen; R 5 It is a halogen; R 6 It is hydrogen; R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and R 9 is hydrogen, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C4)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl; Where R 9 Preferred is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-cycloalkyl-(C1-C2)-alkyl, phenyl-(C1-C2)-alkyl or (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of: (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl.

13. A herbicidal composition comprising at least one compound of formula (I) as defined in any one of claims 1 to 12, an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof, and at least one adjuvant commonly used in the formulation of crop protection compounds; In addition to a composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid as a compound having formula (I) and one or more of the following solvents: acetonitrile, ethyl acetate, water, methanol, tetrahydrofuran; Preferably, in addition to the following compositions: - a composition comprising 3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid; - A composition comprising ethyl 2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylate.

14. The composition of claim 13, wherein The adjuvant comprises a liquid carrier and / or a solid carrier, wherein the liquid carrier is selected from the group consisting of: water, an organic solvent and a mixture thereof, wherein the organic solvent is selected from the group consisting of: a mineral oil fraction, such as kerosene or diesel; an oil of plant or animal origin; paraffin, tetralin, alkylated naphthalene; Alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycols; DMSO; ketones, such as cyclohexanone; esters other than ethyl acetate, such as lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof; and wherein these solid carriers are preferably selected from the group consisting of silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal flour, bark flour, wood flour, nut shell flour and mixtures thereof; Wherein, in the case where the auxiliary agent comprises water, the composition preferably further comprises a surface-active compound, wherein the surface-active compound is preferably selected from the group consisting of anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.

15. A herbicidal composition comprising at least one compound with formula (I) as defined in any one of claims 1 to 12, an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof, at least one auxiliary agent commonly used in the formulation of crop protection compounds, wherein the auxiliary agent is preferably as defined in claim 14, and further comprises a herbicide different from the compound with formula (I).

16. A compound having formula (I), an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof Where R 1 To R 9 is as defined in any one of claims 1 to 12, In addition to compound (I), wherein: -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 Together to form a bridging group -CH2-CH2-O-), 2,5-dihydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH=CH-CH2-O-), 3,5-dimethyl-2,5-dihydrofuran-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -C(CH3)=CH-CH(CH3)-O-), oxathiolane-2,2-diyl (ie, R 7 and R 8 Together, they form a bridging group -S-CH2-CH2-O-), 1,3-dioxolane-5,5-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-O-CH2-O-), 3-methyl-4,5-dihydroisoxazole-5,5-diyl (ie, R 7 and R 8 together to form a bridging group -CH2-C(CH3)=NO-), or And R 9 is hydrogen or ethyl; -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 It is Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form 1-tert-butoxycarbonyl-pyrrolidine-2,2-diyl (i.e., R 7 and R 8 Together they form a bridging group -CH2-CH2-CH2-N(-C(O)-OC(CH3)3)-), and R 9 It is ethyl; -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 is F or Cl, R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 Together to form a bridging group -CH2-CH2-CH2-O-) or 2,5-dihydrothiophene-2,2-diyl (ie, R 7 and R 8 together to form a bridging group -CH=CH-CH2-S-), and R 9 is hydrogen or methyl; -R 1 , R 2 , R 4 and R 6 is hydrogen, R 3 and R 5 Yes F, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-2,2-diyl radical (i.e., R 7 and R 8 Together to form a bridging group -CH2-CH2-O-), and R 9 is hydrogen or ethyl; -R 7 and R 8 Together with the carbon atom to which they are bonded, they form tetrahydrofuran-2,2-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-CH2-O-), and R 9 is tert-butyl; -R 1 is hydrogen or methyl, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form an oxetane-3,3-diyl radical (i.e., R 7 and R 8 together to form a bridging group -CH2-O-CH2-), and R 9 is hydrogen or methyl; and -R 7 and R 8 Together with the carbon atoms to which they are bonded, they form tetrahydropyran-4,4-diyl (i.e., R 7 and R 8 together to form a bridging group -CH2-CH2-O-CH2-CH2), and R 9 is hydrogen or ethyl; And in addition to the following compound (I): -2-[(3-fluoro-5-methylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(3-bromophenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(4-tert-butylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(2,3-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(3-bromo-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(5-chloro-2-methylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(4-trifluoromethoxyphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(4-ethyl-3-fluorophenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(3,5-difluoro-4-methoxyphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(3-chloro-4-(2-methylpropyloxy)phenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(4-hydroxy-2-methyl-5-(1-methylethyl)phenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(4-hydroxy-2,3,5-trimethylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(3-hydroxy-2,4-dimethylphenyl)carbamoyl]oxolane-2-carboxylic acid; -2-[(5-ethyl-2-hydroxyphenyl)carbamoyl]oxolane-2-carboxylic acid; -3-[(4-fluorophenyl)carbamoyl]oxetane-3-carboxylic acid; and -2-[(4-bromo-2-methyl-phenyl)carbamoyl]-1,3-dithiolane-2-carboxylic acid ethyl ester.

17. The compound according to claim 16, wherein R 1 To R 8 is as defined in any one of claims 1 to 12, and wherein R 9 is n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, (C5-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or phenyl-(C1-C3)-alkyl, wherein the last six radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; or R 9 is (C1-C2)-alkyl, which is substituted by m1 groups selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy; Each m is independently 0, 1, 2, 3, 4 or 5; and m1 is 1, 2, 3, 4, or 5; In particular, R 9 is composed of m1 groups R 9a substituted (C1-C6)-alkyl; (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl, The last four radicals are each represented by m radicals R 9a replace; Each R 9a are independently selected from the group consisting of fluorine, chlorine, bromine, cyano, COOR a , (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, wherein the aliphatic or aromatic part of the last seven radicals is each substituted by m radicals selected from the group consisting of fluorine, chlorine and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members; R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, and (C1-C3)-alkoxy; Each m is independently 0, 1, 2, 3, 4 or 5; and m1 is 1, 2, 3, 4, or 5; Specifically R 9 is composed of m1 groups R 9a substituted (C1-C4)-alkyl; (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl; and Each R 9a independently selected from the group consisting of fluorine, chlorine, (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl; More specifically, R 9 is (C1-C4)-alkyl which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl; or R 9 is (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl; Even more specifically, R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio, and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

18. The compound according to any one of claims 16 or 17, wherein These substituents have the following meanings: R 1 It is hydrogen; R 2 It is hydrogen; R 3 It is a halogen; R 4 It is hydrogen; R 5 It is a halogen; R 6 It is hydrogen; R 7 and R 8 together with the carbon atoms to which they are bound, form a saturated or partially unsaturated 4-, 5- or 6-membered monocyclic heterocyclic ring W containing 1 or 2 oxygen atoms as ring members, or 1 oxygen atom and 1 nitrogen atom as ring members, or 1 oxygen atom and 1 sulfur atom as ring members, or 1 sulfur atom as ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; or R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 7- or 8-membered bicyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0, 1 or 2; wherein Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; or two R bonded to the same carbon atom b Forming a methylene group (=CH2); and R 9 as defined in any one of claims 16 or 17; In particular, R 9 is (C1-C4)-alkyl which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 radical selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl and a 5-membered heteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the 5-membered heteroaromatic ring is preferably furanyl; or R 9 It is (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C3)-alkyl.

19. The compound according to claim 18, wherein These substituents have the following meanings: R 1 It is hydrogen; R 2 It is hydrogen; R 3 It is a halogen; R 4 It is hydrogen; R 5 It is a halogen; R 6 It is hydrogen; R 7 and R 8 Together with the carbon atoms to which they are bound, they form a saturated or partially unsaturated 4- or 5-membered monocyclic heterocyclic ring W containing 1 oxygen atom as a ring member, the remaining ring members being carbon atoms, and wherein the ring is surrounded by n radicals R b substituted, wherein n is 0 or 1; wherein Each R b are independently (C1-C3)-alkyl or (C1-C3)-haloalkyl; and R 9 is (C1-C3)-alkyl, which is substituted by 1, 2 or 3 fluorine or chlorine atoms or by 1 group selected from the group consisting of (C1-C3)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfonyl, phenylthio and furyl; or R 9 It is (C3-C4)-cycloalkyl or (C3-C4)-cycloalkyl-(C1-C2)-alkyl.

20. The compound of claim 16, wherein R 7 and R 8 together with the carbon atom to which they are bound, form a saturated or partially unsaturated 4-, 5-, 6-, 7- or 8-membered monocyclic or bicyclic heterocycle W which, in addition to this carbon atom, contains q carbon atoms, u oxygen atoms, v nitrogen atoms and w sulfur atoms as ring members, one of the carbon ring atoms carries p oxo groups, and wherein the ring is substituted by methylene (═CH2); wherein p, q, u, v and w are as defined in any one of claims 1 to 12; Preferably, R 7 and R 8 Together with the carbon atom to which they are bound, they form a saturated 5- or 6-membered, preferably 5-membered, monocyclic heterocycle W which, in addition to this carbon atom, contains 3 or 4 carbon atoms and 1 oxygen atom as ring members and in which the ring is substituted by methylene (═CH 2 ).

21. A method for controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 12, an agriculturally acceptable salt thereof, a stereoisomer thereof or a tautomer thereof or a composition as defined in any one of claims 13 to 15 to act on plants, their seeds and / or their habitat.

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