Herbicidal malonamides containing monocyclic heteroaromatic rings

Abstract

The present invention relates to a malonamide compound of formula (I) [Formula 1] The present invention relates to a compound represented by the formula: JPEG2024532421000133.jpg22170, wherein the variables are as defined in the claims and the specification, and compositions comprising these compounds. The present invention also relates to the use of said malonamide compounds or corresponding compositions for controlling undesirable vegetation. Furthermore, the present invention also relates to a method for applying the malonamide compounds or corresponding compositions.

Description

[Technical Field]

[0001] The present invention relates to malonamide compounds containing a monocyclic heteroaromatic ring and compositions containing the same. The present invention also relates to the use of malonamide compounds containing a monocyclic heteroaromatic ring or corresponding compositions for controlling undesirable vegetation. Furthermore, the present invention relates to a method for applying malonamide compounds containing a monocyclic heteroaromatic ring or corresponding compositions. [Background technology]

[0002] There is a continuing need for new herbicides that are highly active and selective, yet substantially non-toxic to humans and animals, particularly for the purpose of controlling undesirable vegetation in crops.

[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-carboxamides and their use as herbicides.

[0004] WO 87 / 05898 describes the use of malonic acid derivatives to retard plant growth.

[0005] Malonic acid derivatives are also described as plant growth regulators in US Pat. No. 3,072,473. Summary of the Invention [Problem to be solved by the invention]

[0006] Prior art compounds often have poor herbicidal activity, especially at low application rates, and / or poor selectivity resulting in poor compatibility with crop plants.

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

[0008] These and further objects are achieved by the compounds of formula (I) as defined below, including their agriculturally acceptable salts, stereoisomers and tautomers. [Means for solving the problem]

[0009] Thus, the present invention provides a compound of formula (I) [ka] wherein the substituents have the following meanings: Q is a 5- or 6-membered heteroaromatic ring containing, as ring members, 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S, and the ring is Q1 and n substituents R Q2 having; R Q1 is halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl or (C2-C3)-haloalkynyl; R Q2is phenyl-(C1-C3)-alkyl, (C1-C4)-alkylcarbonyl, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, (C1-C4)-alkoxycarbonyl, benzyloxycarbonyl, fluorenyloxycarbonyl, allyloxycarbonyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl or phenylsulfonyl, in which the aliphatic or aromatic moiety in the last-mentioned 14 radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy; 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, (C1-C3)-haloalkoxy or (C1-C3)-alkoxy-(C1-C3)-alkoxy; R 2 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl or (C1-C3)-alkoxy-(C1-C3)-alkyl, in which the aliphatic or cycloaliphatic part of the last five groups is substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R 3is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C2-C6)-alkynyl , (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy or (C1-C3)-alkylthio; R 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy or (C1-C3)-alkoxy-(C1-C3)-alkoxy; X is a bond (X 0 ) or (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ) is a divalent entity selected from the group consisting of: [ka] R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently and independently at each occurrence hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d , N.R.b CO2R e , R a ; (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, imidazolyl (the last six aliphatic, cycloaliphatic, aromatic or heteroaromatic groups being substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano); (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl or (C1-C3)-alkylsulfonyl, in which the aliphatic or cycloaliphatic moiety of the last seven groups is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy; Y is hydrogen, cyano, hydroxyl, Z; (C1~C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl or (C2-C 12 )-alkynyl (the last four aliphatic or cycloaliphatic groups are fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e ,CONR b R h , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. bSO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e substituted with m groups selected from the group consisting of: Z is formed from r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e , R a , R c , R e and R fwherein the sulfur and carbon atoms are substituted with m groups selected from the group consisting of a 3-, 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, fully unsaturated, or aromatic monocyclic, bicyclic, or polycyclic ring, excluding phenyl, bearing n oxo groups; R a is (C1-C6)-alkyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, wherein the last three aliphatic or cycloaliphatic groups are substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C1-C3)-alkoxy; R b are hydrogen or independently R a having one of the meanings given in relation to; R c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl; (C1-C6)-alkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, the aliphatic moieties of the last three groups being substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy; R d is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or furanyl-(C1-C3)-alkyl (the aliphatic, cycloaliphatic, aromatic or heteroaromatic part of the last seven groups can be fluorine, chlorine, bromine, cyano, COR a ,CONR b R h , (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl); R e are independently d has one of the given meanings: R fis (C1-C3)-alkyl or (C1-C3)-alkoxy; R h is hydrogen, (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl (the aliphatic or cycloaliphatic moiety of the last six groups is fluorine, chlorine, bromine, cyano, COR a and (C1-C2)-alkoxy); each k is independently 0, 1, 2, 3, or 4; each m is independently 0, 1, 2, 3, 4, or 5; each n is independently 0, 1, or 2; each r is independently 1, 2, 3, 4, 5, 6, 7, or 8 and agriculturally acceptable salts, stereoisomers and tautomers thereof.

[0010] The present invention also relates to compositions comprising at least one compound of formula (I) and at least one adjuvant customary for formulating crop protection compounds.

[0011] The present invention also provides a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from a herbicidal compound B (component B; different from component A) and an antidote C (component C).

[0012] The present invention further relates to the use of compounds of formula (I) or said compositions for controlling undesired vegetation, as well as to a method for controlling undesired vegetation which comprises applying a herbicidally effective amount of at least one compound of formula (I) or said composition to plants, their seeds and / or their habitats. DETAILED DESCRIPTION OF THE INVENTION

[0013] Definition: Depending on the type of substituents, compounds of formula (I) may have one or more centers of chirality, and in this case may exist as a mixture of enantiomers or diastereomers, but also in the form of pure enantiomers or pure diastereomers. The present invention provides both pure enantiomers or pure diastereomers of compounds of formula I and their mixtures, as well as the use according to the present invention of pure enantiomers or pure diastereomers of compounds of formula I or their mixtures. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and their mixtures, as specific forms of diastereomers. Cis / trans isomers may exist with respect to alkenes, carbon-nitrogen double bonds, nitrogen-sulfur double bonds, amide groups, or cyclic, non-aromatic moieties. The term "stereoisomer" encompasses both optical isomers, such as enantiomers or diastereomers (the latter existing due to the presence of one or more stereocenters in the molecule), and geometric isomers (cis / trans isomers). By way of example, a stereocenter may be present at X 1 ~X 6 R in 5 and R 6 C atoms carrying R 5 and R 6 Another example of a stereogenic center is OR 2 and R 3 is an atom having the formula:

[0014] When the herbicidal compound B and / or antidote C have one or more asymmetric centers, they may also exist as enantiomers or diastereomers, and it is possible to use both the pure enantiomers and diastereomers or mixtures thereof.

[0015] When the compounds of formula (I), herbicidal compound B, and / or antidote C described herein have an ionizable functional group, they can also be utilized in the form of their agriculturally acceptable salts. Suitable salts are generally salts of their cations and acid addition salts of their acids, whose cations and anions, respectively, do not adversely affect the activity of the active compound.

[0016] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably manganese, copper, zinc and iron, as well as 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, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethyl ... and tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), further phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, for example trimethylsulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0017] Useful anions of acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carboxylate, hexafluorosilicate, hexafluorophosphate, benzoate, and also anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0018] Compound (I) may exist in different tautomeric forms. For example, the keto form N(R 1 )-C(=O)-C(OR 2 )(R 3 )-C(=O)-N(R 4 ) is R 3 is hydrogen, its enol form N(R 1 )-C(OH)=C(OR 2 )-C(=O)-N(R 4 ) and N(R 1 )-C(=O)-C(OR 2 )=C(OH)-N(R 4 ) can be in equilibrium with

[0019] The same applies when ring Z contains a C(=O) group as a ring member adjacent to a CH ring member.

[0020] Also, R Q1 When Q is a hydroxyl, ring Q can also exist in the corresponding keto form. For example, when Q is a pyridine ring bearing an OH group at the 2-position, ring Q can exist as its tautomeric form, 1,2-dihydropyridin-2-one.

[0021] Furthermore, when ring Z is a lactam, i.e., contains an amide group (= an unsubstituted secondary nitrogen ring atom adjacent to a carbon ring atom bearing an oxo group) as a ring member, this ring moiety -N(H)-C(=O)- can be in equilibrium with its tautomer -N=C(OH)-.

[0022] The two amide groups -N(R 1 )-C(=O)-C(OR 2 )(R3 )-C(=O)-N(R 4 )-, R 1 and R 4 The same applies when one or both of are hydrogen.

[0023] R 1 is hydrogen, the malonamide moiety -N(H)-C(=O)-C(OR 2 )(R 3 )-C(=O)-N(R 4 )- or -N=C(OH)-C(OR 2 )(R 3 )-C(=O)-N(R 4 )- or as a mixture of the two forms.

[0024] R 4 is hydrogen, the malonamide moiety -N(R 1 )-C(=O)-C(OR 2 )(R 3 )-C(=O)-N(H)- or as -N(R 1 )-C(=O)-C(OR 2 )(R 3 )-C(OH)=N- or as a mixture of these two forms.

[0025] R 1 and R 4 are hydrogen, the malonamide moiety -N(H)-C(=O)-C(OR 2 )(R 3 )-C(=O)-N(H)- or -N=C(OH)-C(OR 2 )(R 3 )-C(=O)-N(H)-, or -N(H)-C(=O)-C(OR 2 )(R 3 ) -C(OH)=N- or -N=C(OH)-C(OR 2 )(R 3)-C(OH)=N- or as a mixture of two, three or all four of the forms shown above.

[0026] The amount of one or the other tautomer present depends on the complete molecular structure and is also strongly dependent on the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature, etc.).

[0027] The term "undesirable vegetation" ("weeds") is understood to include any vegetation growing on non-crop land or at the crop plant site or location of sown crops and other desired crops. Vegetation is any vegetation other than the sown crop or desired crop (if present), including their germinated seeds, emerged seedlings, and established vegetation. Weeds, broadly defined, are plants that are considered undesirable in a particular location.

[0028] The organic moieties mentioned in the definitions of the variables above, like the term halogen, are generic to the individual lists of members of that group. n ~C m indicates in each case the possible number of carbon atoms in the group.

[0029] The term halogen in each case denotes fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

[0030] The term "partially or fully halogenated" means that one or more, for example, one, two, three, four, or five, or all, of the hydrogen atoms of a given group have been replaced by halogen atoms, particularly fluorine or chlorine. Partially or fully halogenated groups are also referred to hereinafter as "halo groups." For example, partially or fully halogenated alkyls are also referred to as haloalkyls.

[0031] As used herein, the term "alkyl" (and other groups that contain an alkyl group, e.g., the alkyl portions of alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, and alkoxyalkyl) generally refers to an alkyl group having, in each instance, 1 to 12 carbon atoms (=C1 to C6 12 -alkyl), often denotes a straight-chain or branched alkyl group having 1 to 6 carbon atoms (=C1-C6-alkyl), in particular 1 to 4 carbon atoms (=C1-C4-alkyl), in particular 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, 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. Examples of C1-C8-alkyl, in addition to those mentioned for C1-C6-alkyl, are n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl and 2-propylpentyl. 12Examples of -alkyl, in addition to those mentioned for C1-C8-alkyl, are nonyl, decyl, 2-propylheptyl, 3-propylheptyl, undecyl, dodecyl and positional isomers thereof.

[0032] As used herein, the term "haloalkyl" (and the haloalkyl moieties of other groups containing a haloalkyl group, such as haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl, and haloalkylsulfinyl) may also be referred to as "partially or fully halogenated alkyl," in each case referring to a straight-chain or branched alkyl group, as defined above, typically having 1 to 6 carbon atoms (=C1-C6-haloalkyl), more often 1 to 3 carbon atoms (=C1-C3-haloalkyl), in which the hydrogen atoms of the group are partially or fully replaced by halogen atoms. Preferred haloalkyl moieties are selected from C1-C3-haloalkyl, particularly C1-C2-haloalkyl, and especially fluorinated C1-C2-alkyl. Examples of C1-C2-haloalkyl include 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, in addition to those mentioned for C1-C2-haloalkyl, are 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, etc.

[0033] The term "hydroxyalkyl" denotes in each case a straight-chain or branched alkyl group, as defined above, usually having 1 to 6 carbon atoms (=C1-C6-hydroxyalkyl), more often 1 to 3 carbon atoms (=C1-C3-hydroxyalkyl), in which one hydrogen atom has been replaced by a hydroxyl group. Examples are hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-2-propyl, etc.

[0034] The term "cyanoalkyl" denotes in each case a straight-chain or branched alkyl group, as defined above, usually having 1 to 6 carbon atoms (=C1-C6-cyanoalkyl), more often 1 to 3 carbon atoms (=C1-C3-cyanoalkyl), in which one hydrogen atom is replaced by a cyano group, e.g., cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyano-2-propyl, etc.

[0035] As used herein, the term "alkenyl" refers, in each case, to an alkyl group having 2 to 12 carbon atoms (=C2 to C4). 12-alkenyl), preferably 2 to 6 carbon atoms (=C2-C6-alkenyl), for example 3 to 6 carbon atoms (=C3-C6-alkenyl), in particular 2 to 4 carbon atoms (=C2-C4-alkenyl) or 2 or 3 carbon atoms (=C2-C3-alkenyl), monounsaturated straight-chain or branched hydrocarbon radicals having a double bond in any position; for example C2-C3-alkenyl, for example ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl; C2-C4-alkenyl, for example 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; C2-C6-alkenyl, for example, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -Methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl nyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3- dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, etc., or C2 to C6, 12 -alkenyl, for example the radicals mentioned for C2-C6-alkenyl, and also 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, nonenyl, decenyl, undecenyl, dodecenyl, etc., and positional isomers thereof.

[0036] Examples of C3-C6-alkenyl are those mentioned for C2-C6-alkenyl, except ethenyl.

[0037] As used herein, the term "haloalkenyl" is also expressed as "alkenyl substituted with halogen," and the haloalkenyl moiety in haloalkenyloxy and the like refers to an unsaturated linear or branched hydrocarbon group having 2 to 6 (=C-C-haloalkenyl), 2 to 4 (=C-C-haloalkenyl), or 2 to 3 (=C-C-haloalkenyl) carbon atoms and a double bond at any position, in which some or all of the hydrogen atoms in these groups have been replaced by the above-mentioned halogen atoms, particularly fluorine, chlorine and bromine, for example, chlorovinyl, chloroallyl, etc.

[0038] As used herein, the term "alkynyl" refers to an alkyl group having 2 to 12 carbon atoms (=C2 to C4). 12-alkynyl), often an unsaturated linear or branched hydrocarbon group having 2 to 6 carbon atoms (=C2-C6-alkynyl), preferably 2 to 4 carbon atoms (=C2-C4-alkynyl) or 2 to 3 carbon atoms (=C2-C3-alkynyl) and a triple bond in any position; for example, C2-C3-alkynyl, for example, ethynyl, 1-propynyl or 2-propynyl; C2-C4-alkynyl, for example, ethynyl, 1-propynyl or 2-propynyl; ethynyl, 1-propynyl or 2-propynyl; 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc.; C2-C6-alkynyl, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, etc. thynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, Examples include 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.

[0039] As used herein, the term "haloalkynyl", also expressed as "alkynyl substituted with halogen", refers to an unsaturated linear or branched hydrocarbon group (as defined above) usually having 2 to 6 carbon atoms (=C2-C6-haloalkynyl), preferably 2 to 4 carbon atoms (=C2-C4-haloalkynyl) or 2 or 3 carbon atoms (=C2-C3-haloalkynyl) and a triple bond at any position, in which some or all of the hydrogen atoms of these groups have been replaced by the above-mentioned halogen atoms, particularly fluorine, chlorine and bromine.

[0040] As used herein (and in other groups containing cycloalkyl groups, e.g., the cycloalkyl moiety of cycloalkoxy and cycloalkylalkyl), the term "cycloalkyl" denotes, in each case, as the (only) ring member, a monocyclic or bicyclic saturated cycloaliphatic group, typically having 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). Examples of monocyclic saturated cycloaliphatic groups having 3 or 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic saturated cycloaliphatic groups having 3 to 5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic saturated cycloaliphatic groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. C5-C6-cycloalkyl is cyclopentyl or cyclohexyl. Examples of bicyclic groups having 5 or 6 carbon atoms include bicyclo[1.1.1]pentyl and bicyclo[2.1.1]hexyl. Preferably, the cycloalkyl is monocyclic.

[0041] As used herein (and in the halocycloalkyl moiety of other groups that contain halocycloalkyl groups), the term "halocycloalkyl" denotes a monocyclic or bicyclic cycloaliphatic group, typically having 3 to 8 carbon atoms ("C3-C8-halocycloalkyl"), preferably 3 to 5 carbon atoms ("C3-C5-halocycloalkyl"), in each case in which at least one, e.g., 1, 2, 3, 4 or 5, of the hydrogen atoms has been replaced by a halogen, in particular 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-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 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.

[0042] As used herein, the term "alkoxy" denotes in each case a straight-chain or branched alkyl radical, usually having 1 to 6 carbon atoms (=C1-C6-alkoxy), preferably 1 to 3 carbon atoms (=C1-C3-alkoxy), in particular 1 or 2 carbon atoms (=C1-C2-alkoxy), which is attached 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). C1-C6-Alkoxy further includes, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy), pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpropoxy, 1-methylpentoxy, 2-methylpropoxy, 1-methylethoxy, 1-methylbutoxy, 1-methylpentoxy, 2-methylpropoxy, 1-methyleth ... ethylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.

[0043] As used herein, the term "haloalkoxy" denotes a straight-chain or branched alkoxy group, in each case as defined above, having 1 to 6 carbon atoms (=C1-C6-haloalkoxy), preferably 1 to 3 carbon atoms (=C1-C3-haloalkoxy), in particular 1 or 2 carbon atoms (=C1-C2-haloalkoxy), in which the hydrogen atoms are partially or fully replaced by halogen atoms, in particular fluorine atoms (in which 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. C1-C6-Haloalkoxy is furthermore, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0044] The term "cyanoalkoxy" denotes in each case a straight-chain or branched alkyl group, as defined above, usually having 1 to 6 carbon atoms (=C1-C6-cyanoalkoxy), more often 1 to 3 carbon atoms (=C1-C3-cyanoalkoxy), in which one hydrogen atom is replaced by a cyano group. Examples are cyanomethoxy, 1-cyanoethoxy, 2-cyanoethoxy, 1-cyanopropoxy, 2-cyanopropoxy, 3-cyanopropoxy, 1-cyano-2-propoxy, etc.

[0045] The term "alkenyloxy" denotes an alkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C2-C6-alkenyloxy is a C2-C6-alkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C3-C6-alkenyloxy is a C3-C6-alkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom.

[0046] The term "haloalkenyloxy" denotes a haloalkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C2-C6-haloalkenyloxy is a C2-C6-haloalkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C3-C6-haloalkenyloxy is a C3-C6-haloalkenyl group as defined above which is bonded to the rest of the molecule via an oxygen atom.

[0047] The term "alkynyloxy" denotes an alkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C2-C6-alkynyloxy is a C2-C6-alkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C3-C6-alkynyloxy is a C3-C6-alkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom.

[0048] The term "haloalkynyloxy" denotes a haloalkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C2-C6-haloalkynyloxy is a C2-C6-haloalkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom. C3-C6-haloalkynyloxy is a C3-C6-haloalkynyl group as defined above which is bonded to the rest of the molecule via an oxygen atom.

[0049] The term "cycloalkoxy" denotes a cycloalkyl group as defined above, which is bonded to the rest of the molecule via an oxygen atom. C3-C6-cycloalkoxy is a C3-C6-cycloalkyl group as defined above, which is bonded to the rest of the molecule via an oxygen atom. Examples of C3-C6-cycloalkoxy include cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy.

[0050] The term "C1-C3-alkoxy-C1-C3-alkyl" refers to an alkyl group having 1 to 3 carbon atoms as defined above, in which one hydrogen atom is replaced by a C1-C3-alkoxy group as defined above. Examples include methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, etc.

[0051] The term "C3-C5-cycloalkyl-C1-C3-alkyl" refers to an alkyl group having 1 to 3 carbon atoms as defined above, in which one hydrogen atom is replaced by a C3-C5-cycloalkyl group as defined above. Examples include cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 1-cyclopropylethoxy, 2-cyclopropylethoxy, 1-cyclobutylethoxy, 2-cyclobutylethoxy, 1-cyclopentylethoxy, 2-cyclopentylethoxy, 1-cyclopropylpropoxy, 2-cyclopropylpropoxy, 3-cyclopropylpropoxy, 1-cyclobutylpropoxy, 2-cyclobutylpropoxy, 3-cyclobutylpropoxy, 1-cyclopentylpropoxy, 2-cyclopentylpropoxy, 3-cyclopentylpropoxy, etc.

[0052] As used herein, the term "alkoxy-alkoxy" refers to an alkoxy group as defined above in which one hydrogen atom is replaced by another alkoxy group as defined above. As used herein, the term "C1-C3-alkoxy-C1-C3-alkoxy" refers to an alkoxy group having 1 to 3 carbon atoms as defined above in which one hydrogen atom is replaced by a C1-C3-alkoxy group as defined above. Examples include methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, and the like.

[0053] As used herein, the term "alkylthio" (including alkylsulfanyl, "alkyl-S" or "alkyl-S(O) k " (where k is also 0)) denotes in each case a linear or branched saturated alkyl group as defined above, which usually contains 1 to 6 carbon atoms (=C1-C6-alkylthio), preferably 1 to 3 carbon atoms (=C1-C3-alkylthio), and is bonded via a sulfur atom at any position of the alkyl group. C1-C2-Alkylthio is methylthio or ethylthio. C1-C3-Alkylthio is furthermore, for example, n-propylthio or 1-methylethylthio (isopropylthio). C1-C6-Alkylthio is furthermore, for example, butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio), 1,1-dimethylethylthio (tert-butylthio), pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1methylpropylthio or 1-ethyl-2-methylpropylthio.

[0054] As used herein, the term "haloalkylthio" refers to an alkylthio group as defined above in which the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine, and / or iodine. C1-C2-haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCHCl2, SCCl3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, or SC2F5. C1-C4-Haloalkylthio is furthermore, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C1-C6-Haloalkylthio is furthermore, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.

[0055] "Alkylsulfinyl" and "Alkyl-S(O) kThe terms "C1-C2-alkylsulfinyl" (where k is 1) are equivalent and, as used herein, denote an alkyl group as defined above bonded via a sulfinyl [S(O)] group. For example, the term "C1-C2-alkylsulfinyl" denotes a C1-C2-alkyl group as defined above bonded via a sulfinyl [S(O)] group. The term "C1-C3-alkylsulfinyl" denotes a C1-C3-alkyl group as defined above bonded via a sulfinyl [S(O)] group. The term "C1-C6-alkylsulfinyl" denotes a C1-C6-alkyl group as defined above bonded via a sulfinyl [S(O)] group. C1-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C3-alkylsulfinyl is further, for example, n-propylsulfinyl or 1-methylethylsulfinyl (isopropylsulfinyl). C1-C6-Alkylsulfinyl further includes, for example, butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl), 1,1-dimethylethylsulfinyl (tert-butylsulfinyl), pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, phenylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.

[0056] "Alkylsulfonyl" and "Alkyl-S(O) k The terms "C1-C2-alkylsulfonyl" (where k is 2) are equivalent and, as used herein, denote an alkyl group as defined above bonded via a sulfonyl [S(O)2] group. The term "C1-C2-alkylsulfonyl" denotes a C1-C2-alkyl group as defined above bonded via a sulfonyl [S(O)2] group. The term "C1-C3-alkylsulfonyl" denotes a C1-C3-alkyl group as defined above bonded via a sulfonyl [S(O)2] group. The term "C1-C6-alkylsulfonyl" denotes a C1-C6-alkyl group as defined above bonded via a sulfonyl [S(O)2] group. C1-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C3-alkylsulfonyl is further, for example, n-propylsulfonyl or 1-methylethylsulfonyl (isopropylsulfonyl). C1-C6-Alkylsulfonyl further includes, for example, butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), 1,1-dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, nyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.

[0057] The substituent "oxo" replaces a CH2 group with a C(=O) group.

[0058] The radical suffix "-carbonyl" indicates that the radical is attached to the remainder of the molecule via a carbonyl (C=O) group, as in, for example, alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, and haloalkoxycarbonyl.

[0059] The term "alkylcarbonyl" denotes an alkyl group as defined above, which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. C1-C3-alkylcarbonyl is a C1-C3-alkyl group as defined above, which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. C1-C4-alkylcarbonyl is a C1-C4-alkyl group as defined above, which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. Examples of C1-C3-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl. Examples of C1-C4-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, etc.

[0060] The term "alkoxycarbonyl" denotes an alkoxy group as defined above which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. C1-C3-alkoxycarbonyl is a C1-C3-alkoxy group as defined above which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. Examples of C1-C3-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl. C1-C6-alkoxycarbonyl refers to a C1-C6-alkoxy group as defined above which is bonded to the rest of the molecule via a carbonyl [C(=O)] group. Examples of C1-C6-alkoxycarbonyl, in addition to those listed for C1-C3-alkoxycarbonyl, are n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl and hexoxycarbonyl.

[0061] The term "alkoxycarbonyl-alkyl" denotes an alkyl group as defined above, in which one hydrogen atom is replaced by an alkoxycarbonyl group as defined above. C1-C6-alkoxycarbonyl-C1-C6-alkyl is a C1-C6-alkyl group as defined above, in which one hydrogen atom is replaced by a C1-C6-alkoxycarbonyl group as defined above.

[0062] Aminocarbonyl refers to the group H2NC(O)-.

[0063] The term "C1-C4-alkylaminocarbonyl" denotes the group C1-C4-alkyl-N(H)-C(O)-. Examples thereof are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-butylaminocarbonyl.

[0064] The term "di-(C1-C4-alkyl)aminocarbonyl" denotes the group (C1-C4-alkyl)N-C(O)-. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropylaminocarbonyl, diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisopropylaminocarbonyl, ethylpropylaminocarbonyl, ethylisopropylaminocarbonyl, n-butyl-methylaminocarbonyl, n-butyl-ethylaminocarbonyl, n-butyl-propylaminocarbonyl, di-n-butylaminocarbonyl, 2-butyl-methylaminocarbonyl, 2-butyl-ethylaminocarbonyl, 2-butyl-propylaminocarbonyl, isobutyl-methylaminocarbonyl, ethyl-isobutylaminocarbonyl, isobutyl-propylaminocarbonyl, tert-butyl-methylaminocarbonyl, tert-butyl-ethylaminocarbonyl, tert-butyl-propylaminocarbonyl and the like.

[0065] Benzyloxycarbonyl is also known as the group Cbz or Z, fluorenyloxycarbonyl is also known as Fmoc, and allyloxycarbonyl is also known as Alloc.

[0066] Phenyl-(C1-C3-alkyl) is a C1-C3-alkyl group as defined above in which one hydrogen atom is replaced by a phenyl ring (i.e. the bond to the rest of the molecule is via the alkyl group). Examples are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl or 2-phenyl-2-propyl.

[0067] Furanyl-(C1-C3-alkyl) is a C1-C3-alkyl group as defined above in which one hydrogen atom is replaced by a 2- or 3-furanyl ring (i.e., the bond to the rest of the molecule is via the alkyl group). Examples are furan-2-yl-methyl, furan-3-yl-methyl, 1-(furan-2-yl)-ethyl, 1-(furan-3-yl)-ethyl, 2-(furan-2-yl)-ethyl, 2-(furan-3-yl)-ethyl, etc.

[0068] Phenylthio is a phenyl ring attached to the rest of the molecule via an S atom.

[0069] Phenylsulfinyl is a phenyl ring attached to the rest of the molecule via an S(O) group.

[0070] Phenylsulfonyl is a phenyl ring attached to the rest of the molecule via an S(O)2 group.

[0071] In the context of this invention, a bicyclic ring includes two rings that share at least one ring atom in common. This term includes condensed (fused) ring systems, in which two rings share two adjacent ring atoms, as well as spiro systems, in which the rings share only one ring atom, and bridged systems, in which the rings share at least three ring atoms in common. Unless otherwise specified, a bicyclic ring may be a carbocyclic ring containing only carbon atoms as ring members, as well as a heterocyclic ring containing at least one heteroatom or group of heteroatoms selected from N, OS, S(O), and S(O)2 as a ring member. Further details are provided below.

[0072] A polycyclic ring contains three or more rings, each of which shares at least one ring atom with at least one other ring in the polycyclic ring system. The rings may be fused, spiro-linked, or bridged; mixed systems (e.g., one ring spiro-linked to a fused system, or a bridged system fused to another ring) are also possible. Unless otherwise specified, a polycyclic ring may be carbocyclic, containing only carbon atoms as ring members, or heterocyclic, containing at least one heteroatom or heteroatom group selected from N, OS, S(O), and S(O)2 as a ring member. Further details are provided below.

[0073] Z is a 3-, 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, fully unsaturated, or aromatic monocyclic, bicyclic, or polycyclic ring (excluding phenyl) formed from r carbon atoms (r=1-8), k nitrogen atoms (k=0-4), n sulfur atoms, and n oxygen atoms, with n oxo groups (n=0-2) attached to the sulfur carbon ring atoms. A carbon ring atom can, of course, have zero or only one oxo group. If the sulfur atom contains one or two oxo groups, the resulting heteroatom groups S(O) and S(O)2 become ring members.

[0074] Thus, ring Z can be a carbocyclic ring (i.e., containing only carbon atoms as ring members; r is 3 to 8, and k, and n as the number of O and S ring atoms, is 0) or a heterocyclic ring (i.e., also containing at least one N, O, and / or S as ring member atom; thus, r is 1 to 7, and at least one of n as the number of O and S ring atoms, and / or k is 1).

[0075] An unsaturated carbocycle contains at least one CC double bond. An unsaturated heterocycle contains at least one CC and / or CN and / or NN double bond. A partially unsaturated carbocycle contains fewer CC double bonds than the maximum allowed by the ring size. A partially unsaturated heterocycle contains fewer CC and / or CN and / or NN double bonds than the maximum allowed by the ring size. A fully (or maximally) unsaturated carbocycle contains as many conjugated CC double bonds as the ring size allows, with the exception that phenyl is not included in the definition of Z. A fully (or maximally) unsaturated heterocycle contains as many conjugated CC and / or CN and / or NN double bonds as the ring size allows. Maximum unsaturated 5- or 6-membered heteromonocycles are generally aromatic. Exceptions are maximum unsaturated 6-membered rings containing O, S, SO, and / or SO as ring members, such as pyran and thiopyran, which are not aromatic.

[0076] Examples of 3-, 4-, 5-, 6-, 7- or 8-membered saturated monocyclic carbocyclic rings Z are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

[0077] Examples of 3-, 4-, 5-, 6-, 7- or 8-membered partially or fully unsaturated monocyclic carbocycles Z are cycloprop-1-enyl, cycloprop-2-enyl, cyclobut-1-enyl, cyclobut-2-enyl, cyclobutadienyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyl, cyclopenta-2,4-dienyl, cyclohex-1-enyl, cyclohex-2-enyl, Cyclohex-3-enyl, cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl, cyclohexa-2,4-dienyl, cyclohexa-2,5-dienyl, cyclohept-1-enyl, cyclohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclohepta-1,3-dienyl, cyclohepta-1,4-dienyl, cyclohepta-1,5-dienyl, cyclohepta-1,6-dienyl, cyclo cyclohepta-2,4-dienyl, cyclohepta-2,5-dienyl, cyclohepta-2,6-dienyl, cyclohepta-3,5-dienyl, cyclohepta-1,3,5-trienyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl, cyclooct-4-enyl, cyclooct-5-enyl, cyclooct-6-enyl, cyclooct-7-enyl, cycloocta-1,3-dienyl, cycloocta-1,4-dienyl, cycloocta -1,5-dienyl, cycloocta-1,6-dienyl, cycloocta-1,7-dienyl, cycloocta-2,4-dienyl, cycloocta-2,5-dienyl, cycloocta-2,6-dienyl, cycloocta-2,7-dienyl, cycloocta-3,5-dienyl, cycloocta-3,6-dienyl, cycloocta-1,3,5-trienyl, cycloocta-1,3,7-trienyl, cycloocta-2,4,6-trienyl, and cyclooctatetraenyl.

[0078] Examples of 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated, fully unsaturated or aromatic heterocycles Z are shown below:

[0079] 3-, 4-, 5-, 6-, 7- or 8-membered saturated monocyclic heterocycles: for example, oxiran-2-yl, thiiran-2-yl, aziridin-1-yl, aziridin-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, 1-oxothietan-2-yl, 1-oxothietan-3-yl, 1,1-dioxothietan-2-yl, 1,1-dioxothietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3 ... tetrahydrothien-2-yl, tetrahydrothien-3-yl, 1-oxotetrahydrothien-2-yl, 1,1-dioxotetrahydrothien-2-yl, 1-oxotetrahydrothien-3-yl, 1,1-dioxotetrahydrothien-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, pyrrolidin-1-yl, pyrrolidin 2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-3-yl, thiazolidin-4-yl 4-oxodiazolidin-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,2,4-Triazolidin-4-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-2-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2 -yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, 1,2,4-hexahydrotriazin-4-yl, 1,2,4-hexahydrotriazin-5-yl, 1,2 ,4-Hexahydrotriazin-6-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-, -2-, -3- or -4-yl, oxepane-2-, -3-, -4- or -5-yl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl, hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl, hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl, oxocane, thiocane, azocanyl, [1,3]diazocanyl, [1,4]diazocanyl, [1,5]diazocanyl, [1,5]oxazocanyl, etc.;

[0080] 3-, 4-, 5-, 6-, 7- or 8-membered partially unsaturated monocyclic heterocycles: 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazoline Isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl , 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydro pyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl, 2, 3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, Droxepinil, for example 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl, tetrahydro-1,3-oxepinyl Sazepinil, tetrahydro-1,4-oxazepinyl, tetrahydro-1,3-dioxepinyl, tetrahydro-1,4-dioxepinyl, 1,2,3,4,5,6-hexahydroazocine, 2,3,4,5,6,7-hexahydroazocine, 1,2,3,4,5,8-hexahydroazocine, 1,2,3,4,7,8-hexahydroazocine, 1,2,3,4,5,6-hexahydro-[1,5]diazocine, 1,2,3,4,7,8-hexahydro-[1,5]diazocine, etc.;

[0081] Maximum unsaturated (non-aromatic) monocyclic heterocycles of 3, 4, 5, 6, 7 or 8 members: pyran-2-yl, pyran-3-yl, pyran-4-yl, thiopyran-2-yl, thiopyran-3-yl, thiopyran-4-yl, 1-oxothiopyran-2-yl, 1-oxothiopyran-3-yl, 1-oxothiopyran-4-yl, 1,1-dioxothiopyran-2-yl, 1,1-dioxothiopyran-3-yl, 1,1-dioxothiopyran-4-yl, 2H-oxazin-2-yl, 2H-oxazin-3-yl, 2H-oxazine -4-yl, 2H-oxazin-5-yl, 2H-oxazin-6-yl, 4H-oxazin-3-yl, 4H-oxazin-4-yl, 4H-oxazin-5-yl, 4H-oxazin-6-yl, 6H-oxazin-3-yl, 6H-oxazin-4-yl, 7H-oxazin-5-yl, 8H-oxazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 4H-1,3-oxazin-2- yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3 -yl, 4H-1,4-oxazin-4-yl, 4H-1,4-oxazin-5-yl, 4H-1,4-oxazin-6-yl, 6H-1,4-oxazin-2-yl, 6H-1,4-oxazin-3-yl, 6H-1,4-oxazin-5-yl, 6H-1,4-oxazin-6-yl, 1,4-dioxin-2-yl, 1,4-oxathiin-2-yl, 1H-azepine, 1H-[1,3]-diazepine, 1H-[1,4]-diazepine, [1,3]diazocine, [1,5]diazocine, [1,5]diazocine, etc.;

[0082] 5- or 6-membered monocyclic aromatic heterocycles: for example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4- Thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,3,4-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, 1,4,3-Thiadiazol-2-yl, 1,2,3,4-Tetrazol-1-yl, 1,2,3,4-Tetrazol-2-yl, 1,2,3,4-[1H]-Tetrazol-5-yl, 1,2,3,4-[2H]-Tetrazol-5-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-oxo 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,3,4-tetrazin-1-yl, 1,2,3,4-tetrazin-2-yl, 1,2,3,4-tetrazin-5-yl and the like.

[0083] The bicyclic ring has 4 to 8 members, preferably 5 to 8 members.

[0084] Examples of 5-8 membered bicyclic saturated spirocyclic carbocycles include spiro[2.2]pentyl, spiro[2.3]hexyl, spiro[2.4]heptyl, spiro[3.3]heptyl, spiro[4.4]nonyl, spiro[5.5]undecyl, and the like.

[0085] Examples of 5-8 membered bicyclic saturated fused carbocycles include bicyclo[3.1.0]hexyl, bicyclo[3.2.0]heptyl, bicyclo[3.3.0]octyl, 1,2,3,3a,4,5,6,6a-octahydropentalenyl, bicyclo[4.2.0]octyl, and the like.

[0086] Examples of 5-8 membered bicyclic saturated bridged carbocycles include bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[3.2.1]octyl, and the like.

[0087] An example of a 5-8 membered polycyclic saturated carbocyclic ring is cubyl.

[0088] An example of a 5-8 membered partially unsaturated bicyclic bridged carbocycle is bicyclo[2.2.2]oct-2-enyl.

[0089] Examples of 5- to 8-membered bicyclic saturated fused heterocycles are shown below. [ka]

[0090] Examples of 5-8 membered bicyclic saturated spirocyclic heterocycles are shown below. [ka]

[0091] Examples of 5- to 8-membered bicyclic saturated bridged heterocycles are shown below. [ka]

[0092] Examples of 5- to 8-membered partially unsaturated bicyclic bridged heterocycles are shown below. [ka]

[0093] In the structures shown above, # represents the point of attachment to the rest of the molecule. The point of attachment is not limited to the ring on which it is shown, but can be on either of the two rings, and on either a carbon ring atom or a nitrogen ring atom. When a ring has one or more substituents, these may be attached to a carbon ring atom and / or a nitrogen ring atom.

[0094] Q is a 5- or 6-membered heteroaromatic ring containing, as ring members, 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S. Examples thereof include furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5 ... 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, 1,2,5-oxadiazol-3-yl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,2,3-triazol-4 ... 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, 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl, 1,2,3,4-[1H]-tetrazol-5-yl, 1,2,3,4-[2H] ...2-yl Examples of the tetrazin-1-yl include pyrazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,3,4-tetrazin-1-yl, 1,2,3,4-tetrazin-2-yl, and 1,2,3,4-tetrazin-5-yl.

[0095] Examples of 5-membered heteroaromatic rings Q containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members are furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl and isothiazol-5-yl.

[0096] Examples of 6-membered heteroaromatic rings Q containing 1 or 2 nitrogen ring atoms are pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl and pyrazin-2-yl.

[0097] The following statements regarding preferred embodiments of the variants (substituents) of the compounds of formula I are valid on their own and preferably in combination with one another, and in combination with their stereoisomers, tautomers or salts. The following statements regarding preferred embodiments of the variants are also valid on their own and preferably in combination with one another, where applicable, with respect to the compounds of formula I and to the uses and methods according to the invention, and to the compositions according to the invention.

[0098] Preferably, R 1 is selected from the group consisting of hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl. More preferably, R 1is hydrogen, (C1-C3)-alkyl or (C1-C3)-alkoxy-(C1-C3)-alkyl, in particular hydrogen, methyl or methoxymethyl. In particular R 1 is hydrogen or (C1-C3)-alkyl. In particular, R 1 is hydrogen.

[0099] Preferably, R 4 is selected from the group consisting of hydrogen, (C1-C6)-alkyl and (C3-C6)-cycloalkyl. More preferably, R 4 is hydrogen or (C1-C3)-alkyl. In particular, R 4 is hydrogen.

[0100] Preferably, R 1 is hydrogen or (C1-C3)-alkyl; and R 4 is hydrogen or (C1-C3)-alkyl.

[0101] More preferably, R 1 and R 4 are both hydrogen.

[0102] Preferably, R 2 is selected from the group consisting of (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, and (C1-C3)-alkoxy-(C1-C3)-alkyl, each substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano. More preferably, R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl or (C3-C6)-alkynyl. More preferably, R 2 is (C1-C6)-alkyl, for example (C1-C4)-alkyl. In particular, R 2 is methyl or ethyl, especially methyl.

[0103] Preferably, R 3is selected from the group consisting of hydrogen, halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy and (C3-C6)-alkynyloxy. More preferably, R 3 is hydrogen, halogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy, or (C3-C6)-alkynyloxy. 3 is hydrogen or halogen; in particular hydrogen or fluorine, especially hydrogen.

[0104] Divalent group (X 1 )~(X 6 ), the intramolecular orientation is as depicted, with the left arrow representing the bond to the adjacent nitrogen atom and the right arrow representing the bond to Y.

[0105] X is bonded ("X 0 "), compound (I) can also be depicted as: [ka]

[0106] X is the formula (X 1 ), compound (I) may also be represented as follows: [ka]

[0107] X is the formula (X 2 ), compound (I) may also be represented as follows: [ka]

[0108] X is the formula (X 3 ), compound (I) may also be represented as follows: [ka]

[0109] X is the formula (X 4 ), compound (I) may also be represented as follows: [ka]

[0110] X is the formula (X 5 ), compound (I) may also be represented as follows: [ka]

[0111] X is the formula (X 6 ), compound (I) may also be represented as follows: [ka]

[0112] Divalent group (X 1 )~(X 6 ) in R 5 ~R 10 are, independently of each other and independently of each other occurrence, preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d(C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl (the last three aliphatic or cycloaliphatic groups are each independently substituted with m fluorine atoms); (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl and (C1-C3)-alkylthio (the aliphatic or cycloaliphatic moieties of the last seven groups are each independently substituted with m fluorine atoms).

[0113] More preferably, R 5 ~R 10 are each independently and independently at each occurrence hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, COR e ,CONR b R d (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl (the last three aliphatic or cycloaliphatic groups are each independently substituted with m fluorine atoms); (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy and (C2-C6)-alkynyloxy (the aliphatic or cycloaliphatic moieties of the last four groups are each independently substituted with m fluorine atoms).

[0114] In particular, R 5 ~R 10 are each independently and independently at each occurrence hydrogen, fluorine, chlorine, CO2R e ,CONR b R d , (C1-C6)-alkyl substituted with m fluorine atoms, and (C1-C6)-alkoxy substituted with m fluorine atoms.

[0115] In particular, R 5 ~R 10are, independently at each occurrence and independently at each occurrence, hydrogen, halogen, (C1-C6)-alkyl, (C1-C3)-alkoxy and COR e More particularly, R 5 ~R 10 is independently at each occurrence and independently at each occurrence hydrogen or (C1-C6)-alkyl, in particular hydrogen or methyl.

[0116] A suitable divalent group (X 1 )~(X 6 Non-exhaustive examples of ) are CH, CHCH, CH(CH), CHCHCH, CH(CHCH), CH(CHCH), CH(CH)CH, C(CH), C(CH)CH, C(iPr)CH, CH(CHiPr)CH, CHCH=CH, C(CH)C≡C, CH(CF)CH, CH(CH)CHO, CHCHO, CH(cPr)CHO, CH(CHOCH), CH(CHCHSCH), CH(COOH), CH(COOCH), CH(COOH)CH, CH(COOCH)CH, CHC(OH)(CF), CH(CONHCH), CH(CONHCH)CH and CHCHCONHCH. cPr is cyclopropyl; iPr is isopropyl.

[0117] In a preferred embodiment, X is a bond or a divalent unit (X 1 In the latter case, preferably, R 5 and R 6 are each independently hydrogen or (C1-C6)-alkyl, more preferably hydrogen or methyl. In particular, R 5 and R 6 One of the groups is hydrogen and the other is methyl, so X 1 is, in particular, CH(CH3).

[0118] Y is preferably hydrogen, cyano, hydroxyl, Z; (C1-C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl and (C2-C 12)-alkynyl (the aliphatic or cycloaliphatic portions of the last four groups each independently represent fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, COR e and CONR b R h and m groups selected from the group consisting of:

[0119] More preferably, Y is hydrogen, cyano, hydroxyl, Z, (C1-C 12 )-alkyl and (C3-C8)-cycloalkyl (the aliphatic or cycloaliphatic moieties of the last two groups each independently represent fluorine, COR e and CONR b R h and m groups selected from the group consisting of:

[0120] In another more preferred embodiment, Y is (C1 to C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl and (C2-C 12 )-alkynyl (the aliphatic or cycloaliphatic portions of the last four groups each independently represent fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e ,CONR b R h , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2Re , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e More preferably, Y is selected from the group consisting of (C1 to C 12 )-alkyl, (C3-C8)-cycloalkyl, (C2-C 12 )-alkenyl and (C2-C 12 )-alkynyl (the aliphatic or cycloaliphatic portions of the last four groups each independently represent fluorine and COR e and m groups selected from the group consisting of:

[0121] In particular, Y is Z, (C1~C 12 )-alkyl and (C3-C8)-cycloalkyl (the aliphatic or cycloaliphatic moieties of the last two groups are each independently fluorine, (C1-C2)-alkoxy, CO2R e and CONR b R h More particularly, Y is selected from the group consisting of Z and m groups COR e (C1 to C 12 In this context, m is preferably 1 or 2, in particular 1.

[0122] In one preferred embodiment, Y is Z.

[0123] Representative, non-exhaustive examples of (non-phenyl) 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated, fully unsaturated or aromatic monocyclic, bicyclic or polycyclic rings Z are the following structures (and, of course, the exemplary rings defined above): [ka] [ka]

[0124] The ring may be further substituted as defined above. The arrow or # represents the bond / point of attachment to Y (or NR4 if Y is a bond).

[0125] Z is preferably formed from r carbon atoms and n oxygen atoms, each of which is represented by COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f , C(R b )=NOR e , R a , R c , R e and R fand wherein the carbon atoms are substituted with m groups from the group consisting of: e ,CONR b R h , R a , R c , R e and R f Preferred are 4-, 5- or 6-membered saturated, partially unsaturated or fully unsaturated, monocyclic rings (excluding phenyl), including aromatic, substituted with m groups from the group consisting of:

[0126] In another preferred embodiment, Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and is COR e ,CONR b R h ,CONR e SO2R a , R a , R c , R e and R f and wherein the sulfur and carbon atoms are substituted with m groups from the group consisting of 3-, 4-, 5-, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic rings, excluding phenyl, and wherein the sulfur and carbon atoms have n oxo groups. e ,CONR b R h , R a , R c , R e and R f and the sulfur and carbon atoms bear n oxo groups.

[0127] More preferably, Z is COR e ,CONR bR h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e S(O)R a ,CONR e SO2R a ,CONR b1 SO2NR b2 R b3 , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b1 SO2NR b2 R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e , R a , R c , R e and R f and wherein the carbon ring atoms bear n oxo groups. In this context, m is preferably 0, 1, 2 or 3, more preferably 1 or 2, in particular 1, and in this context, n is preferably 0 or 1, in particular 0. More preferably, the 3-, 4-, 5- or 6-membered saturated, partially unsaturated or fully unsaturated monocyclic carbocycle Z is COR e ,CONR b R h , S(O) n R a , SO2NR bR d , SO2NR b COR e , C.O.R. b ,CONR e S(O)R a ,CONR e SO2R a ,CONR b1 SO2NR b2 R b3 , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b1 SO2NR b2 R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e m groups selected from the group consisting of: a , R c , R e and R f wherein m1 has one of the meanings given for m and is preferably 0, 1, 2 or 3, more preferably 1 or 2, in particular 1; and m2 has one of the meanings given for m and is preferably 0, 1 or 2, in particular 0. Further preferably, the 3-, 4-, 5- or 6-membered saturated, partially unsaturated or fully unsaturated monocyclic carbocyclic ring Z is substituted with COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e S(O)R a ,CONRe SO2R a ,CONR b1 SO2NR b2 R b3 , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b1 SO2NR b2 R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e wherein m1 has one of the meanings given for m and is preferably 0, 1, 2 or 3, more preferably 1 or 2, especially 1.

[0128] More preferably, Z is COR e ,CONR b R h ,CONR e SO2R a , R a , R c , R e and R f and m groups selected from the group consisting of: e ,CONR b R h and CONR e SO2R a m groups selected from the group consisting of: a , R c , R e and R fwherein m1 has one of the meanings given for m and is preferably 0, 1, 2 or 3, more preferably 1 or 2, in particular 1; and m2 has one of the meanings given for m and is preferably 0, 1 or 2, in particular 0. Further preferably, the 5- or 6-membered saturated or partially unsaturated carbocyclic ring Z is substituted with m groups selected from the group consisting of COR e ,CONR b R h and CONR e SO2R a and m1 groups selected from the group consisting of, where m1 has one of the meanings given for m and is preferably 0, 1, 2 or 3, more preferably 1 or 2, in particular 1 (and the group R a , R c , R e and R f (not replaced by ).

[0129] Examples of 5- or 6-membered saturated or partially unsaturated carbocyclic rings are cyclopentyl, cyclopent-1-en-1-yl, cyclopent-2-en-1-yl, cyclopent-3-en-1-yl, cyclopenta-1,3-dien-1-yl, cyclopenta-1,4-dien-1-yl, cyclopenta-2,4-dien-1-yl, cyclohexyl, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl, cyclohexa-1,3-dien-1-yl, cyclohexa-1,4-dien-1-yl, cyclohexa-1,5-dien-1-yl, cyclohexa-2,4-dien-1-yl and cyclohexa-2,5-dien-1-yl. Among these, cyclopentyl, cyclopent-1-en-1-yl, cyclopent-2-en-1-yl, cyclopent-3-en-1-yl and cyclohexyl are preferred, a specific example being cyclopent-2-en-1-yl.

[0130] Non-exhaustive examples of such rings include the following structures: [ka] [ka]

[0131] In the above structure, # represents the point of attachment to the rest of the molecule, and R x is CO2R e ,CONR b R h ,CONR e SO2R a , R a , R c , R e or R f The ring may further have one or two substituents at any position selected from F, CN, methyl, CF3 or methoxy. More preferably, R x is CO2R e ,CONR b R h or CONR e SO2R a represents CO2R e In this context, R e is preferably hydrogen or (C1-C6)-alkyl, more preferably (C1-C4)-alkyl.

[0132] Thus, even more preferably, Z is a group selected from m groups COR e is a 5- or 6-membered saturated or partially unsaturated carbocyclic ring substituted with e is hydrogen or (C1-C6)-alkyl, preferably (C1-C4)-alkyl. In this context, m is preferably 1 or 2, more preferably 1. Examples of such rings are R x CO2R e represents R e is the above structure in which is hydrogen or (C1-C6)-alkyl, preferably (C1-C4)-alkyl.

[0133] In particular, Z is a group consisting of m groups COR e is a 5- or 6-membered partially unsaturated carbocyclic ring substituted with eis hydrogen or (C1-C6)-alkyl, preferably (C1-C4)-alkyl. In this context, m is preferably 1 or 2, more preferably 1.

[0134] More particularly, Z is a group COR e is a 5-membered partially unsaturated carbocyclic ring substituted with R e is hydrogen or (C1-C6)-alkyl, preferably (C1-C4)-alkyl. Examples of such rings are: [ka] (In the formula, R x is CO2R e represents R e is hydrogen or (C1-C6)-alkyl).

[0135] In particular, Z is [ka] (In the formula, R x is CO2R e represents R e is hydrogen or (C1-C6)-alkyl, in particular (C1-C4)-alkyl).

[0136] In another preferred embodiment, Z is COR e ,CONR b R h , S(O) n R a , SO2NR b R d , SO2NR b COR e , C.O.R. b ,CONR e S(O)R a ,CONR e SO2R a ,CONR b1 SO2NR b2 R b3 , N.R. b R e , N.R. b COR e , N.R.b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b1 SO2NR b2 R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e and wherein the carbon ring atoms bear n oxo groups. In this context, m is preferably 1 or 2, more preferably 1. In this context, n is preferably 0 or 1, in particular 0. More preferably, Z contains one oxygen atom as a ring member and m groups COR e In this context, R is a saturated or partially unsaturated 5- or 6-membered heterocycle substituted with e is preferably hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl; in particular hydrogen or (C1-C6)-alkyl, in this connection m is preferably 1 or 2, more preferably 1. Thus, more particularly, Z contains one oxygen atom as a ring member and m groups COR e a saturated or partially unsaturated 5- or 6-membered heterocycle substituted with e is hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl; in particular is hydrogen or (C1-C6)-alkyl and m is 1 or 2, preferably 1. More particularly, Z contains one oxygen atom as a ring member and m groups COR e a saturated or partially unsaturated 5-membered heterocycle substituted with eis hydrogen or (C1-C6)-alkyl, in which context m is preferably 1 or 2, more preferably 1. In particular, Z contains one oxygen atom as a ring member and one group COR e wherein Re is hydrogen or (C1-C6)-alkyl.

[0137] Examples of 3-, 4-, 5- or 6-membered saturated, partially unsaturated or fully unsaturated heterocyclic rings containing one or two oxygen atoms as ring members are oxiran-2-yl, oxetan-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2,3-dihydrofuran ...oxan-2-yl, 2 yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 3,6-dihydro-2H-pyran-2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-2-yl, 3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-5-yl or 3,4-dihydro-2H-pyran-6-yl.

[0138] Examples of saturated or partially unsaturated 5- or 6-membered heterocyclic rings containing one oxygen atom as a ring member are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 3,6-dihydro-2H-pyran- 2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-2-yl, 3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-5-yl or 3,4-dihydro-2H-pyran-6-yl.

[0139] Examples of saturated or partially unsaturated 5-membered heterocycles containing one oxygen atom as a ring member are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, or 2,5-dihydrofuran-3-yl.

[0140] Non-exhaustive examples of saturated or partially unsaturated five-membered heterocycles containing one oxygen atom as a ring member are the following structures: [ka]

[0141] In the above structure, the wavy line represents the point of attachment to the rest of the molecule, and the arrow represents the substituent CO2R e ,CONR b R h ,CONR e SO2R a , R a , R c , R e or R f The substituent preferably represents a point of attachment to COR. e ,CONR b Rh or CONR e SO2R a and CO2R in particular e In this regard, R e is preferably hydrogen or (C1-C6)-alkyl.

[0142] Among the above rings, the following structures are preferred: [ka] Here again, the wavy line represents the point of attachment to the rest of the molecule, and the arrow represents the substituent CO2R e ,CONR b R h ,CONR e SO2R a , R a , R c , R e or R f The substituent preferably represents a point of attachment to COR. e ,CONR b R h or CONR e SO2R a and CO2R in particular e In this regard, R e is preferably hydrogen or (C1-C6)-alkyl.

[0143] Preferably, however, ring Z is a carbocyclic ring.

[0144] In another preferred embodiment, Y is S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e ,CONR b R h , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R.b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e More preferably, Y is a (C1-C8)-alkyl substituted with m groups selected from the group consisting of: e (C1-C4)-alkyl substituted with, where R e is hydrogen or (C1-C6)-alkyl and m is 1 or 2. More preferably, Y is a group CO2R e (C1-C4)-alkyl substituted with, where R e is hydrogen or (C1-C6)-alkyl, and R e is preferably (C1-C4)-alkyl.

[0145] In a preferred embodiment, X is a bond and Y is Z, where Z has one of the general or preferred meanings given above.

[0146] In another preferred embodiment, X is a divalent unit (X 1 ) and R 5 and R 6 is as defined above and in particular independently hydrogen or (C1-C6)-alkyl; and Y is S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e ,CONR b R h, C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )=NOR e and m groups selected from the group consisting of (C1-C8)-alkyl substituted with m groups.

[0147] In another preferred embodiment, X is a bond; and Y is S(O) n R a , SO2NR b R d , SO2NR b COR e , CO2R e ,CONR b R h , C.O.R. b ,CONR e SO2R a , N.R. b R e , N.R. b COR e , N.R. b CONR e R e , N.R. b CO2R e , N.R. b SO2R e , N.R. b SO2NR b R e , OCONR b R e, OCSNR b R e , POR f R f and C(R b )=NOR e and m groups selected from the group consisting of (C1-C8)-alkyl substituted with m groups.

[0148] More preferably, X is a divalent unit (X 1 ) and R 5 and R 6 is independently hydrogen or methyl; and Y is CO2R e ,CONR b R h and CONR e SO2R a and m groups selected from the group consisting of (C1-C4)-alkyl substituted with m groups.

[0149] In this context, Y preferably represents m groups COR e (C1-C4)-alkyl substituted with, where R e is hydrogen or (C1-C6)-alkyl, and R e is preferably (C1-C4)-alkyl.

[0150] In this context, m is preferably 1.

[0151] In another more preferred embodiment, X is a bond; and Y is CO2R e ,CONR b R h and CONR e SO2R a and m groups selected from the group consisting of (C1-C6)-alkyl substituted with m groups.

[0152] In this context, Y preferably represents m groups COR e (C1-C6)-alkyl substituted with, where R eis hydrogen or (C1-C6)-alkyl, and R e is preferably (C1-C4)-alkyl.

[0153] In this context, m is preferably 1.

[0154] In this latter alternative more preferred embodiment, (C1-C6)-alkyl in Y is preferably COR e ,CONR b R h and CONR e SO2R a a group -C(R 51 )(R 61 )-C1-C4-alkyl, and R 51 and R 61 is independently hydrogen or methyl.

[0155] In this context, Y is more preferably a group selected from m groups COR e A group -C(R 51 )(R 61 )-C1-C4-alkyl, where R e is hydrogen or (C1-C6)-alkyl, where R e is preferably (C1-C4)-alkyl; and R 51 and R 61 are independently hydrogen or methyl.

[0156] In this context, m is preferably 1.

[0157] Q is preferably a 5-membered heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing one or two nitrogen atoms as ring members, wherein the ring Q is Q1 and n substituents R Q2 It has.

[0158] Examples of such rings Q are furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5 ... The preferred examples of the present invention include thiazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl and pyrazin-2-yl.

[0159] R Q1 is in this context preferably selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy.

[0160] R Q2 is in this context preferably phenyl-(C1-C3)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, (C1-C4)-alkoxycarbonyl, benzyloxycarbonyl, fluorenyloxycarbonyl, allyloxycarbonyl or (C1-C3)-alkoxy-(C1-C3)-alkyl; more preferably benzyl, acetyl, methylaminocarbonyl, dimethylaminocarbonyl, (C1-C4)-alkoxycarbonyl or methoxymethyl, in particular (C1-C4)-alkoxycarbonyl.

[0161] k in this context is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and n in this context is preferably 0 or 1.

[0162] More preferably, Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein ring Q is selected from the group consisting of k substituents R Q1 and n substituents R Q2 It has.

[0163] Examples of such 5-membered heteroaromatic rings Q are furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl and isothiazol-5-yl.

[0164] Examples of such 6-membered heteroaromatic rings Q are pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl and pyrazin-2-yl.

[0165] In this regard, R Q1 is preferably selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy.

[0166] In this regard, R Q2 is preferably (C1-C4)-alkoxycarbonyl.

[0167] In this context, k is preferably 0, 1, 2 or 3, and in this context, n is preferably 0 or 1.

[0168] Particularly preferred ring Q has the following structure: [ka] That is, thien-2-yl, thien-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl.

[0169] These rings are each formed of k substituents R Q1 and n substituents R Q2 In this regard, R Q1 is preferably selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy. Q2 is preferably (C1-C4)-alkoxycarbonyl, in this context k is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, in this context n is preferably 0 or 1.

[0170] Specifically, Q is isoxazolyl, thienyl or pyridyl (more precisely thien-2-yl, thien-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl).

[0171] In a preferred embodiment, Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein ring Q is a ring containing k substituents R Q1 and n substituents R Q2 where R Q1is selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy, R Q2 is (C1-C4)-alkoxycarbonyl; where k is 0, 1, 2 or 3 and n is 0 or 1; R 1 is hydrogen; R 2 is (C1-C6)-alkyl; R 3 is hydrogen or halogen; R 4 is hydrogen; X is a bond; and Y is Z; where Z is a group selected from m groups COR e is a 5- or 6-membered saturated or partially unsaturated carbocyclic ring substituted with R e is hydrogen or (C1-C6)-alkyl and m is 1 or 2; or X is a divalent unit (X 1 ) and R 5 and R 6 are, independently of one another, hydrogen or (C1-C6)-alkyl; and Y is a group selected from m groups COR e (C1-C4)-alkyl substituted by, where R e is hydrogen or (C1-C6)-alkyl and m is 1 or 2.

[0172] More preferably, Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein ring Q is a ring containing k substituents R Q1 and n substituents R Q2 where R Q1 is selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy, R Q2is (C1-C4)-alkoxycarbonyl; where k is 0, 1, 2 or 3 and n is 0 or 1; R 1 is hydrogen; R 2 is methyl or ethyl; R 3 is hydrogen; R 4 is hydrogen; X is a bond; and Y is Z; where Z is a group COR e is a 5-membered partially unsaturated carbocyclic ring substituted by e is (C1-C6)-alkyl; or X is a divalent unit (X 1 ), where R 5 and R 6 one of which is hydrogen and the other is hydrogen or methyl; and Y is one group COR e (C1-C4)-alkyl substituted by, where R e is (C1-C6)-alkyl.

[0173] Even more preferably, Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein ring Q is a ring containing k substituents R Q1 and n substituents R Q2 where R Q1 is selected from the group consisting of halogen, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy and (C1-C3)-haloalkoxy, R Q2 is (C1-C4)-alkoxycarbonyl; where k is 0, 1 or 2 and n is 0 or 1; R 1 is hydrogen; R 2 is methyl or ethyl; R 3 is hydrogen; R4 is hydrogen; X is a bond; and Y is Z; where Z is a group COR e is a 5-membered partially unsaturated carbocyclic ring substituted by e is (C1-C4)-alkyl; or X is a divalent unit (X 1 ), where R 5 and R 6 one of which is hydrogen and the other is hydrogen or methyl; and Y is one group COR e (C1-C4)-alkyl substituted by, where R e is (C1-C4)-alkyl.

[0174] especially, Q is a 5-membered heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing one nitrogen atom as a ring member, wherein ring Q is a ring containing k substituents R Q1 and n substituents R Q2 where R Q1 is selected from the group consisting of halogen, cyano, (C1-C3)-alkyl and (C1-C3)-alkoxy, R Q2 is (C1-C4)-alkoxycarbonyl; where k is 0, 1 or 2 and n is 0 or 1; R 1 is hydrogen; R 2 is methyl or ethyl, preferably methyl; R 3 is hydrogen; R 4 is hydrogen; X is a bond; and Y is Z; where Z is a group COR e is a 5-membered partially unsaturated carbocyclic ring substituted by e is (C1-C4)-alkyl; or X is a divalent unit (X 1 ), where R 5 and R 6one of which is hydrogen and the other is hydrogen or methyl; and Y is one group COR e (C1-C4)-alkyl substituted by, where R e is (C1-C4)-alkyl.

[0175] In the above specific and particular embodiments, the 5-membered partially unsaturated carbocyclic ring Z is preferably ring Z10 (shown below), where # indicates the point of attachment to the rest of the molecule.

[0176] R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are compounds (I) in which the combinations of X and Y have the meanings defined in each row of Table A below.

[0177] [Table 1]

[0178] [Table 2]

[0179] [Table 3]

[0180] [Table 4]

[0181] [Table 5]

[0182] [Table 6]

[0183] [Table 7]

[0184]

Table 8

[0185]

Table 9

[0186]

Table 10

[0187]

Table 11

[0188]

Table 12

[0189]

Table 13

[0190]

Table 14

[0191]

Table 15

[0192] Table 16

[0193] Table 17

[0194]

Table 18

[0195] Table 19

[0196] Table 20

[0197] Table 21

[0198] Table 22

[0199] Table 23

[0200] Table 24

[0201] Table 25

[0202] Table 26

[0203] Table 27

[0204] Table 28

[0205] Table 29

[0206] Table 30

[0207] Table 31

[0208] Table 32

[0209]

Table 33

[0210] Table 34

[0211] Table 35

[0212] Table 36

[0213] Table 37

[0214] Table 38

[0215] Table 39

[0216] Table 40

[0217] Table 41

[0218] Table 42

[0219] Table 43

[0220] Table 44

[0221] Table 45

[0222] Table 46

[0223] Table 47

[0224] Table 48

[0225] Table 49

[0226]

Table 50

[0227] Table 51

[0228] Table 52

[0229] Table 53

[0230] Table 54

[0231] Table 55

[0232] Table 56

[0233] Table 57

[0234] Table 58

[0235] Table 59

[0236] Table 60

[0237] Table 61

[0238] Table 62

[0239] Table 63

[0240] Table 64

[0241] Table 65

[0242] Table 66

[0243] Table 67

[0244] Table 68

[0245] Table 69

[0246] Table 70

[0247] Table 71

[0248] Table 72

[0249] Table 73

[0250] Table 74

[0251] Table 75

[0252] Table 76

[0253] Table 77

[0254] Table 78

[0255] Table 79

[0256] [Table 80]

[0257] [Table 81]

[0258] [Table 82]

[0259] [Table 83]

[0260] [ka]

[0261] In Z1 to Z39, # is NR 4 indicates the attachment point to

[0262] Among rings Z1 to Z39, ring Z10 is particularly preferred.

[0263] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is pyridin-2-yl.

[0264] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-fluoropyridin-2-yl.

[0265] For a single compound, R 1 and R4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-chloropyridin-2-yl.

[0266] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-bromopyridin-2-yl.

[0267] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-cyanopyridin-2-yl.

[0268] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-methylpyridin-2-yl.

[0269] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-methoxypyridin-2-yl.

[0270] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoropyridin-2-yl.

[0271] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloropyridin-2-yl.

[0272] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromopyridin-2-yl.

[0273] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyanopyridin-2-yl.

[0274] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methylpyridin-2-yl.

[0275] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxypyridin-2-yl.

[0276] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoropyridin-2-yl.

[0277] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloropyridin-2-yl.

[0278] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromopyridin-2-yl.

[0279] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanopyridin-2-yl.

[0280] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylpyridin-2-yl.

[0281] For a single compound, R 1 and R 4is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxypyridin-2-yl.

[0282] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridin-2-yl.

[0283] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridin-2-yl.

[0284] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridin-2-yl.

[0285] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridin-2-yl.

[0286] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridin-2-yl.

[0287] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridin-2-yl.

[0288] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,6-difluoropyridin-2-yl.

[0289] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,6-dichloropyridin-2-yl.

[0290] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,6-dibromopyridin-2-yl.

[0291] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,6-dimethylpyridin-2-yl.

[0292] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,6-dimethoxypyridin-2-yl.

[0293] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-6-fluoropyridin-2-yl.

[0294] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-chloro-4-fluoropyridin-2-yl.

[0295] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-6-fluoropyridin-2-yl.

[0296] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-bromo-4-fluoropyridin-2-yl.

[0297] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-6-chloropyridin-2-yl.

[0298] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-bromo-4-chloropyridin-2-yl.

[0299] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-6-methylpyridin-2-yl.

[0300] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-fluoro-4-methylpyridin-2-yl.

[0301] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-6-methylpyridin-2-yl.

[0302] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-chloro-4-methylpyridin-2-yl.

[0303] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-6-methylpyridin-2-yl.

[0304] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-bromo-4-methylpyridin-2-yl.

[0305] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-6-methylpyridin-2-yl.

[0306] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-cyano-4-methylpyridin-2-yl.

[0307] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxy-6-methylpyridin-2-yl.

[0308] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 6-methoxy-4-methylpyridin-2-yl.

[0309] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is pyridin-4-yl.

[0310] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoropyridin-4-yl.

[0311] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloropyridin-4-yl.

[0312] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromopyridin-4-yl.

[0313] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanopyridin-4-yl.

[0314] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylpyridin-4-yl.

[0315] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxypyridin-4-yl.

[0316] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridin-4-yl.

[0317] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridin-4-yl.

[0318] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridin-4-yl.

[0319] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridin-4-yl.

[0320] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridin-4-yl.

[0321] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridin-4-yl.

[0322] For a single compound, R 1 and R 4is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-difluoropyridin-4-yl.

[0323] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-dichloropyridin-4-yl.

[0324] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-dibromopyridin-4-yl.

[0325] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-dicyanopyridin-4-yl.

[0326] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-dimethylpyridin-4-yl.

[0327] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2,6-dimethoxypyridin-4-yl.

[0328] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloro-6-fluoropyridin-4-yl.

[0329] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromo-6-fluoropyridin-4-yl.

[0330] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromo-6-chloropyridin-4-yl.

[0331] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyano-6-fluoropyridin-4-yl.

[0332] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloro-6-cyanopyridin-4-yl.

[0333] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromo-6-cyanopyridin-4-yl.

[0334] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoro-6-methylpyridin-4-yl.

[0335] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloro-6-methylpyridin-4-yl.

[0336] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromo-6-methylpyridin-4-yl.

[0337] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyano-6-methylpyridin-4-yl.

[0338] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxy-6-methylpyridin-4-yl.

[0339] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoro-6-methoxypyridin-4-yl.

[0340] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloro-6-methoxypyridin-4-yl.

[0341] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromo-6-methoxypyridin-4-yl.

[0342] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyano-6-methoxypyridin-4-yl.

[0343] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoropyridin-5-yl.

[0344] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloropyridin-5-yl.

[0345] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromopyridin-5-yl.

[0346] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanopyridin-5-yl.

[0347] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylpyridin-5-yl.

[0348] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxypyridin-5-yl.

[0349] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-(trifluoromethyl)-pyridin-5-yl.

[0350] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-(trifluoromethoxy)-pyridin-5-yl.

[0351] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridin-5-yl.

[0352] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridin-5-yl.

[0353] For a single compound, R 1and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridin-5-yl.

[0354] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridin-5-yl.

[0355] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridin-5-yl.

[0356] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridin-5-yl.

[0357] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(trifluoromethyl)-pyridin-5-yl.

[0358] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(trifluoromethoxy)-pyridin-5-yl.

[0359] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoropyridin-5-yl.

[0360] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloropyridin-5-yl.

[0361] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromopyridin-5-yl.

[0362] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanopyridin-5-yl.

[0363] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylpyridin-5-yl.

[0364] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxypyridin-5-yl.

[0365] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(trifluoromethyl)-pyridin-5-yl.

[0366] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(trifluoromethoxy)-pyridin-5-yl.

[0367] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridazin-4-yl.

[0368] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridazin-4-yl.

[0369] For a single compound, R1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridazin-4-yl.

[0370] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridazin-4-yl.

[0371] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridazin-4-yl.

[0372] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridazin-4-yl.

[0373] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridazin-5-yl.

[0374] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridazin-5-yl.

[0375] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridazin-5-yl.

[0376] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridazin-5-yl.

[0377] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridazin-5-yl.

[0378] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridazin-5-yl.

[0379] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoropyridazin-6-yl.

[0380] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloropyridazin-6-yl.

[0381] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromopyridazin-6-yl.

[0382] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanopyridazin-6-yl.

[0383] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylpyridazin-6-yl.

[0384] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxypyridazin-6-yl.

[0385] For a single compound, R 1 and R 4is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoropyrimidin-4-yl.

[0386] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloropyrimidin-4-yl.

[0387] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromopyrimidin-4-yl.

[0388] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanopyrimidin-4-yl.

[0389] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylpyrimidin-4-yl.

[0390] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxypyrimidin-4-yl.

[0391] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoropyrimidin-5-yl.

[0392] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloropyrimidin-5-yl.

[0393] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromopyrimidin-5-yl.

[0394] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanopyrimidin-5-yl.

[0395] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylpyrimidin-5-yl.

[0396] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxypyrimidin-5-yl.

[0397] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluoropyrimidin-6-yl.

[0398] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chloropyrimidin-6-yl.

[0399] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromopyrimidin-6-yl.

[0400] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanopyrimidin-6-yl.

[0401] For a single compound, R 1 and R4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylpyrimidin-6-yl.

[0402] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxypyrimidin-6-yl.

[0403] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is thien-2-yl.

[0404] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluorothien-2-yl.

[0405] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chlorothien-2-yl.

[0406] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromothien-2-yl.

[0407] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyanothien-2-yl.

[0408] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methylthien-2-yl.

[0409] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxythien-2-yl.

[0410] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-thien-2-yl.

[0411] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluorothien-2-yl.

[0412] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chlorothien-2-yl.

[0413] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromothien-2-yl.

[0414] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanothien-2-yl.

[0415] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylthien-2-yl.

[0416] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxythien-2-yl.

[0417] For a single compound, R 1 and R 4 is hydrogen and R2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-thien-2-yl.

[0418] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluorothien-2-yl.

[0419] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chlorothien-2-yl.

[0420] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromothien-2-yl.

[0421] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanothien-2-yl.

[0422] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylthien-2-yl.

[0423] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxythien-2-yl.

[0424] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-thien-2-yl.

[0425] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-difluorothien-2-yl.

[0426] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-dichlorothien-2-yl.

[0427] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-dibromothien-2-yl.

[0428] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-dicyanothien-2-yl.

[0429] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-dimethylthien-2-yl.

[0430] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-dimethoxythien-2-yl.

[0431] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,4-di(methoxycarbonyl)-thien-2-yl.

[0432] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-difluorothien-2-yl.

[0433] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-dichlorothien-2-yl.

[0434] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-dibromothien-2-yl.

[0435] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-dicyanothien-2-yl.

[0436] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-dimethylthien-2-yl.

[0437] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-dimethoxythien-2-yl.

[0438] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3,5-di(methoxycarbonyl)-thien-2-yl.

[0439] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-difluorothien-2-yl.

[0440] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-dichlorothien-2-yl.

[0441] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-dibromothien-2-yl.

[0442] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-dicyanothien-2-yl.

[0443] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-dimethylthien-2-yl.

[0444] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-dimethoxythien-2-yl.

[0445] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4,5-di(methoxycarbonyl)-thien-2-yl.

[0446] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-4-fluorothien-2-yl.

[0447] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-3-fluorothien-2-yl.

[0448] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-fluorothien-2-yl.

[0449] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-fluorothien-2-yl.

[0450] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-chlorothien-2-yl.

[0451] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-chlorothien-2-yl.

[0452] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-4-fluorothien-2-yl.

[0453] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-3-fluorothien-2-yl.

[0454] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-4-cyanothien-2-yl.

[0455] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-3-cyanothien-2-yl.

[0456] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-cyanothien-2-yl.

[0457] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-cyanothien-2-yl.

[0458] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-4-methylthien-2-yl.

[0459] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-3-methylthien-2-yl.

[0460] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-4-methylthien-2-yl.

[0461] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-3-methylthien-2-yl.

[0462] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-methylthien-2-yl.

[0463] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-methylthien-2-yl.

[0464] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-4-methoxythien-2-yl.

[0465] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-3-methoxythien-2-yl.

[0466] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-4-methoxythien-2-yl.

[0467] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-3-methoxythien-2-yl.

[0468] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-methoxythien-2-yl.

[0469] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-methoxythien-2-yl.

[0470] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-4-(methoxycarbonyl)-thien-2-yl.

[0471] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-3-(methoxycarbonyl)-thien-2-yl.

[0472] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-4-(methoxycarbonyl)-thien-2-yl.

[0473] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-3-(methoxycarbonyl)-thien-2-yl.

[0474] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-4-(methoxycarbonyl)-thien-2-yl.

[0475] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-3-(methoxycarbonyl)-thien-2-yl.

[0476] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-4-methylthien-2-yl.

[0477] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-3-methylthien-2-yl.

[0478] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-4-methoxythien-2-yl.

[0479] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-3-methoxythien-2-yl.

[0480] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-4-(methoxycarbonyl)-thien-2-yl.

[0481] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-3-(methoxycarbonyl)-thien-2-yl.

[0482] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxy-4-methylthien-2-yl.

[0483] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxy-3-methylthien-2-yl.

[0484] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-4-methylthien-2-yl.

[0485] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-3-methylthien-2-yl.

[0486] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-4-methoxythien-2-yl.

[0487] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-3-methoxythien-2-yl.

[0488] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-5-fluorothien-2-yl.

[0489] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-3-fluorothien-2-yl.

[0490] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-fluorothien-2-yl.

[0491] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-fluorothien-2-yl.

[0492] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-chlorothien-2-yl.

[0493] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-chlorothien-2-yl.

[0494] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-5-fluorothien-2-yl.

[0495] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-3-fluorothien-2-yl.

[0496] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-5-cyanothien-2-yl.

[0497] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-3-cyanothien-2-yl.

[0498] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-cyanothien-2-yl.

[0499] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-cyanothien-2-yl.

[0500] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-5-methylthien-2-yl.

[0501] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-3-methylthien-2-yl.

[0502] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-5-methylthien-2-yl.

[0503] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-3-methylthien-2-yl.

[0504] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-methylthien-2-yl.

[0505] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-methylthien-2-yl.

[0506] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-5-methoxythien-2-yl.

[0507] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-3-methoxythien-2-yl.

[0508] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-5-methoxythien-2-yl.

[0509] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-3-methoxythien-2-yl.

[0510] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-methoxythien-2-yl.

[0511] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-methoxythien-2-yl.

[0512] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoro-5-(methoxycarbonyl)-thien-2-yl.

[0513] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-3-(methoxycarbonyl)-thien-2-yl.

[0514] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 and -XY has one of the meanings defined in the single row of Table A and Q is 3-chloro-5-(methoxycarbonyl)-thien-2-yl.

[0515] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-3-(methoxycarbonyl)-thien-2-yl.

[0516] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromo-5-(methoxycarbonyl)-thien-2-yl.

[0517] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-3-(methoxycarbonyl)-thien-2-yl.

[0518] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-5-methylthien-2-yl.

[0519] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-3-methylthien-2-yl.

[0520] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-5-methoxythien-2-yl.

[0521] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-3-methoxythien-2-yl.

[0522] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3and -XY has one of the meanings defined in the single row of Table A and Q is 3-cyano-5-(methoxycarbonyl)-thien-2-yl.

[0523] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-3-(methoxycarbonyl)-thien-2-yl.

[0524] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxy-5-methylthien-2-yl.

[0525] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxy-3-methylthien-2-yl.

[0526] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-5-methylthien-2-yl.

[0527] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-3-methylthien-2-yl.

[0528] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-5-methoxythien-2-yl.

[0529] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-3-methoxythien-2-yl.

[0530] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-5-fluorothien-2-yl.

[0531] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-4-fluorothien-2-yl.

[0532] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-fluorothien-2-yl.

[0533] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-fluorothien-2-yl.

[0534] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-chlorothien-2-yl.

[0535] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-chlorothien-2-yl.

[0536] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-5-fluorothien-2-yl.

[0537] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-4-fluorothien-2-yl.

[0538] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-5-cyanothien-2-yl.

[0539] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-4-cyanothien-2-yl.

[0540] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-cyanothien-2-yl.

[0541] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-cyanothien-2-yl.

[0542] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-5-methylthien-2-yl.

[0543] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-4-methylthien-2-yl.

[0544] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-5-methylthien-2-yl.

[0545] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-4-methylthien-2-yl.

[0546] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-methylthien-2-yl.

[0547] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-methylthien-2-yl.

[0548] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-5-methoxythien-2-yl.

[0549] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-4-methoxythien-2-yl.

[0550] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-5-methoxythien-2-yl.

[0551] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-4-methoxythien-2-yl.

[0552] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-methoxythien-2-yl.

[0553] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-methoxythien-2-yl.

[0554] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoro-5-(methoxycarbonyl)-thien-2-yl.

[0555] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoro-4-(methoxycarbonyl)-thien-2-yl.

[0556] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 and -XY has one of the meanings defined in the single row of Table A and Q is 4-chloro-5-(methoxycarbonyl)-thien-2-yl.

[0557] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloro-4-(methoxycarbonyl)-thien-2-yl.

[0558] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromo-5-(methoxycarbonyl)-thien-2-yl.

[0559] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromo-4-(methoxycarbonyl)-thien-2-yl.

[0560] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-5-methylthien-2-yl.

[0561] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-4-methylthien-2-yl.

[0562] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-5-methoxythien-2-yl.

[0563] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-4-methoxythien-2-yl.

[0564] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyano-5-(methoxycarbonyl)-thien-2-yl.

[0565] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyano-4-(methoxycarbonyl)-thien-2-yl.

[0566] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxy-5-methylthien-2-yl.

[0567] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxy-4-methylthien-2-yl.

[0568] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-5-methylthien-2-yl.

[0569] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-4-methylthien-2-yl.

[0570] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-5-methoxythien-2-yl.

[0571] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-4-methoxythien-2-yl.

[0572] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3and -XY has one of the meanings defined in the single row of Table A and Q is thien-3-yl.

[0573] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-fluorothien-3-yl.

[0574] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-chlorothien-3-yl.

[0575] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-bromothien-3-yl.

[0576] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-cyanothien-3-yl.

[0577] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methylthien-3-yl.

[0578] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-methoxythien-3-yl.

[0579] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 2-(methoxycarbonyl)-thien-3-yl.

[0580] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluorothien-3-yl.

[0581] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chlorothien-3-yl.

[0582] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromothien-3-yl.

[0583] For a single compound, R 1 and R 4 is hydrogen and R2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanothien-3-yl.

[0584] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylthien-3-yl.

[0585] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxythien-3-yl.

[0586] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-thien-3-yl.

[0587] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluorothien-3-yl.

[0588] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chlorothien-3-yl.

[0589] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromothien-3-yl.

[0590] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyanothien-3-yl.

[0591] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methylthien-3-yl.

[0592] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxythien-3-yl.

[0593] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-thien-3-yl.

[0594] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is isoxazol-3-yl.

[0595] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoroisoxazol-3-yl.

[0596] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloroisoxazol-3-yl.

[0597] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromoisoxazol-3-yl.

[0598] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyanoisoxazol-3-yl.

[0599] For a single compound, R 1 and R 4is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methylisoxazol-3-yl.

[0600] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-tert-butylisoxazol-3-yl.

[0601] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxyisoxazol-3-yl.

[0602] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-isoxazol-3-yl.

[0603] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoroisoxazol-3-yl.

[0604] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloroisoxazol-3-yl.

[0605] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromoisoxazol-3-yl.

[0606] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanoisoxazol-3-yl.

[0607] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylisoxazol-3-yl.

[0608] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-tert-butylisoxazol-3-yl.

[0609] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxyisoxazol-3-yl.

[0610] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-isoxazol-3-yl.

[0611] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is isoxazol-5-yl.

[0612] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-fluoroisoxazol-5-yl.

[0613] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-chloroisoxazol-5-yl.

[0614] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-bromoisoxazol-5-yl.

[0615] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-cyanoisoxazol-5-yl.

[0616] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methylisoxazol-5-yl.

[0617] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-tert-butylisoxazol-5-yl.

[0618] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-methoxyisoxazol-5-yl.

[0619] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-isoxazol-5-yl.

[0620] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoroisoxazol-5-yl.

[0621] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloroisoxazol-5-yl.

[0622] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromoisoxazol-5-yl.

[0623] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanoisoxazol-5-yl.

[0624] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylisoxazol-5-yl.

[0625] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-tert-butylisoxazol-5-yl.

[0626] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxyisoxazol-5-yl.

[0627] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-isoxazol-5-yl.

[0628] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is isoxazol-4-yl.

[0629] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-fluoroisoxazol-4-yl.

[0630] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-chloroisoxazol-4-yl.

[0631] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-bromoisoxazol-4-yl.

[0632] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-cyanoisoxazol-4-yl.

[0633] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methylisoxazol-4-yl.

[0634] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-tert-butylisoxazol-4-yl.

[0635] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-methoxyisoxazol-4-yl.

[0636] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 3-(methoxycarbonyl)-isoxazol-4-yl.

[0637] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-fluoroisoxazol-4-yl.

[0638] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-chloroisoxazol-4-yl.

[0639] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-bromoisoxazol-4-yl.

[0640] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-cyanoisoxazol-4-yl.

[0641] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methylisoxazol-4-yl.

[0642] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-tert-butylisoxazol-4-yl.

[0643] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-methoxyisoxazol-4-yl.

[0644] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 5-(methoxycarbonyl)-isoxazol-4-yl.

[0645] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 1-methyl-2-(methoxycarbonyl)-pyrrol-4-yl.

[0646] For a single compound, R 1 and R 4 is hydrogen and R 2 , R 3 Particularly preferred are further compounds (I) in which -XY has one of the meanings defined in the single row of Table A and Q is 4-(methoxycarbonyl)-thiazol-2-yl.

[0647] The compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example the following processes: [ka]

[0648] The compounds of formula (I) can be prepared according to methods described in the prior art, or methods analogous thereto, which synthesizes utilize commercially available starting materials or starting materials that can be prepared according to conventional procedures starting from readily available compounds.

[0649] Compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling reagent. Thus, compounds of formula (I) can be synthesized from the corresponding carboxylic acid (1 equivalent) using a coupling reagent (1-2 equivalents), such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), an organic base (1-3 equivalents), and an amine (II) (1-3 equivalents). The reaction is typically carried out in an organic solvent. Preferably, an aprotic organic solvent is used. Most preferably, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) is used. The reaction is carried out at a temperature between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine. [ka]

[0650] Carboxylic acids (III) are commercially available or can be prepared from the corresponding esters (IV) (where R P is alkyl or benzyl). P When R is alkyl, the ester (IV) can be cleaved using aqueous alkali metal hydroxide. Preferably, lithium hydroxide, sodium hydroxide, or potassium hydroxide (1-2 equivalents) is utilized. 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. When R in (IV) is P When is benzyl, the ester can be cleaved using palladium on charcoal (0.001 to 1 equivalent) and hydrogen gas as a catalyst at temperatures between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol, or ethanol is used. [ka]

[0651] Compounds of formula (IV) can be prepared from carboxylic acids (VI) and commercially available amines (V) using a base and a coupling reagent. Thus, compounds of formula (IV) can be synthesized from the corresponding carboxylic acid (1 equivalent) using a coupling reagent (1-2 equivalents), such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate), an organic base (1-3 equivalents), and an amine (V) (1-3 equivalents). The reaction is typically carried out in an organic solvent. Preferably, an aprotic organic solvent is used. Most preferably, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) is used. The reaction is carried out at a temperature between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine. [ka]

[0652] Carboxylic acids (VI) may be prepared from the corresponding diesters by selective cleavage of one ester group. q When is an alkyl ester, selective ester cleavage can be achieved using an aqueous base. Preferably, an alkali metal hydroxide is used. Most preferably, lithium hydroxide, sodium hydroxide, or potassium hydroxide is used. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, THF, methanol, or acetonitrile is used. The reaction is carried out at a temperature between 0°C and 100°C, preferably at room temperature.

[0653] Alternatively, trimethyltin hydroxide (e.g., 1 equivalent) in 1,2-dichloroethane may be used at room temperature to reflux temperature, preferably under reflux (as described in Angew. Chem. Int. Ed., 2005, 44:1378-1382), preferably at reflux temperature. q When is benzyl, the ester can be cleaved using palladium on charcoal (0.001 to 1 equivalent) and hydrogen gas as a catalyst at temperatures between 0°C and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol, or ethanol is used. [ka]

[0654] The diester (VII) is commercially available or can be prepared from the corresponding diazo compound (VIII) by the addition of rhodium tetraacetate ([Rh(OAc)2]2) (0.001-0.1 equivalents) and the alcohol HO-R. 7 and the alkoxy malonate (VII) (R 8 =H) is obtained. The reaction is typically carried out in an organic solvent, preferably toluene, at a temperature between 0°C and 100°C. Preferably, the reaction is carried out at 60°C as described in Angew. Chem. Int. Ed. 2014, 53, 14230-14234. If the diazo compound (VIII) is not commercially available, it can be prepared as described in Angew. Chem. Int. Ed. 2014, 53, 14230-14234. [ka]

[0655] Alternatively, the diester (VII) can be synthesized from the commercially available monoester (XI), a base, and chloroformate (XII) (1-3 equivalents) as described in Bioorganic & Medicinal Chemistry Letters, 12(11), 1501-1505; 2002. The reaction is typically carried out in an organic solvent, preferably tetrahydrofuran. The preferred temperature range is between -78°C and 25°C. Preferably, the reaction is warmed from -78°C to 25°C over 16 hours. Preferably, lithium diisopropylamide (1 equivalent) is used as the base.

[0656] Or, R 8 The diester (VII) in which ≡ is fluorine can be prepared from the corresponding non-fluorinated malonate using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) as described in WO 12 / 129384. Water and / or an organic solvent can be used. Preferably, the reaction is carried out in acetonitrile. The reaction is carried out using 1 to 4 equivalents of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) at a temperature between 0°C and reflux, preferably 60°C. Alternatively, N-fluorobenzenesulfonimide (CAS 133745-75-2) may be utilized (see, for example, Differding, E., & Ofner, H. (1991). N-Fluorobenzenesulfonimide: A practical reagent for electrophilic fluorinations. Synlett, 1991 (03)) 187-189). [ka]

[0657] Amines of formula (XIII) can be prepared from lactams (XIV), which are commercially available or can be prepared by alkylation as described in Org. Process Res. Dev. 2018, 22, 337-343, and commercially available alcohols (XV), using thionyl chloride (2 equivalents) as described in Tetrahedron Lett. 2001, 42, 1347-1350. This reaction is typically carried out in the coupling alcohol (XV) as a solvent. This reaction is carried out at a temperature between 0°C and reflux. Preferably, this reaction is carried out at room temperature.

[0658] To broaden the spectrum of action, the compounds of formula (I) may be mixed with many representatives of other herbicidal or growth-regulating active ingredients, and then applied simultaneously. Suitable ingredients for combination include, for example, acetamide, amide, aryloxyphenoxypropionate, benzamide, benzofuran, benzoic acid, benzothiadiazinon, bipyridinium, carbamate, chloroacetamide, chlorocarboxylic acid, cyclohexanedione, dinitroaniline, dinitrophenol, diphenyl ether, glycine, imidazolinone, isoxazole, isoxazolidinone, nitrile, N-phenylphthalimide, oxadiazole, oxazolidinedione, oxyacetamide, phenoxycarboxylic acid, phenylcarbamate, phenylpyrazole ... Herbicides from the classes of zolines, phenylpyridazines, phosphinates, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl (thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, and ureas.

[0659] It may be more advantageous to apply the compound of formula (I) alone or in combination with other herbicides, or in the form of a mixture with other crop protection agents, such as agents for controlling pests or plant pathogenic fungi or bacteria.Also, the compatibility with mineral salt solutions used to treat nutrient and trace element deficiencies is also interesting.Other additives, such as non-phytotoxic oils and concentrated oils, may also be added.

[0660] In one embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) (compound A or component A) and at least one further active compound selected from herbicides B (compound B), preferably herbicides B of classes b1) to b15), and antidotes C (compound C).

[0661] In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one further active compound B (herbicide B).

[0662] Examples of herbicides B that can be used in combination with compounds A of formula (I) according to the invention are:

[0663] b1) From the group of the lipid biosynthesis inhibitors: ACC inhibitor herbicides (ACC-herbicide), for example, alloxydim, alloxydim sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop- Methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6; 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3;5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6);5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate methyl ester (CAS 1312337-51-1;4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5);Non-ACC inhibitor herbicides, such as benfuresate, butyrate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazyl, triallate, and vernolate;

[0664] b2) From the group of ALS inhibitors: Sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cyclosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, Iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxlam, pyrimisulfan and pyroxsulam, pyrimidinyl benzoates such as bispyribac, bispyri Bac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-Dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides, such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; Of these, preferred embodiments of the present invention relate to those compositions comprising at least one imidazolinone herbicide;

[0665] b3) From the group of photosynthetic inhibitors: Amicarbazones, inhibitors of photosystem II, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-Dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides such as chlorotriazine, triazinones, triazinediones, methylthiotriazines and pyridazinones, for example, ametryn, atrazine, chloridazon, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl ureas such as chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, methox Herbicides include but are not limited to: thiadiazuron, monolinuron, nebulon, siduron, tebuthiuron, and thiadiazuron; phenylcarbamates such as desmedipham, karbutilat, phenmedipham, and phenmedipham ethyl; nitrile herbicides such as bromofenoxime, bromoxynil, and its salts and esters, and ioxynil and its salts and esters; uracils such as bromacil, lenacil, and terbacil; bentazone and bentazone sodium; pyridate, pyridafol, pentanochlor and propanil; and photosystem I inhibitors such as diquat, diquat dibromide, paraquat, paraquat dichloride, and paraquat dimethyl sulfate. Among these, preferred embodiments of the present invention relate to compositions containing at least one aryl urea herbicide. Among these, equally preferred embodiments of the present invention relate to compositions containing at least one triazine herbicide. Among these, an equally preferred embodiment of the present invention relates to a composition comprising at least one nitrile herbicide.

[0666] b4) From the group of the protoporphyrinogen-IX oxidase inhibitors: Acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranyl, fluazolate, flufurenpyr, flufurenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluroglicofen, fluroglicofen-ethyl, fluthiacet, fluthiacet-methyl, fomesa Fen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiafenacil, trifludimoxadine, 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 10147-10-1) 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 (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetic acid ethyl ester (CAS 158274-50-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]methyl acetate (CAS 2271389-22-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]ethyl acetate (CAS 2230679-62-4), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-Dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);,

[0667] b5) From the group of bleaching herbicides: PDS inhibitors: beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7); HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, whitening agents, and agents with unknown site of action. target): aclonifen, amitrole, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixuzolone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7).

[0668] b6) From the group of the EPSP synthase inhibitors: Glyphosate, glyphosate isopropylammonium, glyphosate potassium salt and glyphosate trimesium salt (sulfosate).

[0669] b7) From the group of the glutamine synthetase inhibitors: Viranafos (Bialaphos), Viranafos sodium, Glufosinate, Glufosinate P and Glufosinate ammonium.

[0670] b8) From the group of the DHP synthase inhibitors: Ashram.

[0671] b9) From the group of the mitotic inhibitors: Compounds of the K1 group: dinitroanilines, such as benfluralin, butralin, dinitramine, ethalfuralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates, such as amiprophos, amiprophos-methyl and butamifos, benzoic acid herbicides, such as chlorthal, chlorthal-dimethyl, pyridines, such as dithiopyr and thiazopyr, benzamides, such as propyzamide and tebutam; compounds of the K2 group: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham, of which compounds of the K1 group, especially dinitroaniline, are preferred;

[0672] b10) From the group of VLCFA inhibitors: Chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamide, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and other herbicides such as anilophos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9. [ka] Isoxazoline compounds of formula (III) are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576; Among the VLCFA inhibitors, chloroacetamide and oxyacetamide are preferred;

[0673] b11) From the group of the cellulose biosynthesis inhibitors: Chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);

[0674] b12) From the group of the uncoupler herbicides: Dinoseb, dinoterb and DNOC and their salts;

[0675] b13) From the group of the auxin herbicides: 2,4-D and its salts and esters, for example, clasifos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts, for example, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benzolin, benzolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, furopyrixifene, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, halaxifene and its salts and esters (CAS 943832-60-8);MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA(2,3,6) and its salts and esters, triclopyr and its salts and esters, florpilauxifene, florpilauxifene-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);

[0676] b14) From the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr sodium, naptalam and naptalam sodium.

[0677] b15) From the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipine, DSMA, dymron, endothal and its salts, etobenzanide, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozoline, methyl azide, methyl bromide, methyldymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetflupyrolimet and tridiphane.

[0678] Furthermore, it may be useful to apply the compound of formula (I) in combination with a safener. A safener is a compound that prevents or reduces damage to useful plants without significantly affecting the herbicidal action of the compound of formula (I) on undesirable vegetation. It can be applied either before sowing (planting) the useful plants (for example, seed treatment, shoot or seedling), or as a pre-emergence or post-emergence application. The safener and the compound of formula (I) and optional herbicide B can be applied simultaneously or sequentially.

[0679] In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one safener C (component C).

[0680] Examples of antidotes are, for example, (quinoline-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-diallyl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oximinophenylacetonitrile, acetophenoxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic acid amide, 1,8-naphthalene anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, phosphothiolates and N-alkyl-O-phenylcarbamates and agriculturally acceptable salts thereof, and agriculturally acceptable derivatives thereof, such as amides, esters and thioesters, provided that they contain an acid group.

[0681] Examples of antidote compounds C are benoxacor, cloquintocet, siometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), metcamifen, and BPCMS (CAS 54091-06-4).

[0682] The active compounds B and C of groups b1) to b15) are known herbicides and antidotes, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R.R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W.H.Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS number 52836-31-4] is also known as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS number 71526-07-3] is also known as AD-67 and MON4660.

[0683] The assignment of active compounds to each mechanism of action is based on current knowledge. If an active compound applies to several mechanisms of action, it is assigned to only one mechanism of action.

[0684] The present invention also relates to a formulation comprising at least an adjuvant and at least one compound of formula (I) according to the invention.

[0685] The formulations contain a pesticidally effective amount of a compound of formula (I). The term "effective amount" refers to an amount of a combination or compound of formula (I) that is sufficient to control undesirable plants, particularly undesirable vegetation in crops (i.e., cultivated plants), without causing substantial damage to the treated crop plants. Such amounts can vary within a wide range and depend on various factors, such as the undesirable vegetation to be controlled, the treated crop plants or materials, climatic conditions, and the particular compound of formula (I) used.

[0686] The compounds of formula (I), their salts, amides, esters or thioesters can be converted into conventional formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, 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, lozenges, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), presses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations (e.g., GF) for the treatment of plant seedlings, such as seeds. These and other formulation types are described in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th As defined in CropLife International, Ed. May 2008.

[0687] The formulations can be prepared in a known manner, for example as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0688] Suitable auxiliaries are solvents, liquid carriers, solid carriers or extenders, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizers, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0689] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling fractions of mineral oil, e.g., kerosene, light oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g., toluene, paraffin, tetrahydronaphthalene, alkylated naphthalene; alcohols, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonate esters; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0690] Suitable solid carriers or extenders are mineral earths, such as 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 grain flour, bark flour, wood flour, nut shell flour and mixtures thereof.

[0691] 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, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0692] Suitable anionic surfactants are alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates include alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates include phosphoric acid esters. Examples of carboxylates include alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0693] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters, alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for the alkoxylation. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerin esters, or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants include homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0694] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybasics. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybasics are polyvinylamine or polyethyleneamine.

[0695] Suitable adjuvants are compounds that themselves have negligible or even no pesticidal activity, but enhance the biological performance of the compound of formula (I) on the target. Examples include surfactants, mineral or vegetable oils, and other adjuvants. Further examples are described in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0696] Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0697] Suitable fungicides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

[0698] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[0699] Suitable antifoaming agents are silicones, long chain alcohols and salts of fatty acids.

[0700] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes, examples of which include inorganic colorants (e.g., iron oxide, titanium oxide, ferricyanide) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0701] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.

[0702] Examples of formulation types and methods for their preparation are as follows:

[0703] i) Water-soluble concentrate (SL, LS) 10 to 60% by weight of a compound of formula (I) according to the invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and antidote C (component C), and 5 to 15% by weight of a wetting agent (for example, an alcohol alkoxylate), are dissolved in water and / or a water-soluble solvent (for example, an alcohol) in a remaining amount up to 100% by weight. The active substance dissolves upon dilution with water.

[0704] ii) Dispersed concentrate (DC) 5 to 25% by weight of a compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and antidote C (component C), and 1 to 10% by weight of a dispersant (for example, polyvinylpyrrolidone) are dissolved in a remaining amount up to 100% by weight of an organic solvent (for example, cyclohexanone). Upon dilution with water, a dispersion is obtained.

[0705] iii) Emulsifiable concentrate (EC) 15 to 70% by weight of a compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and antidote C (component C), and 5 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., aromatic hydrocarbon) with the remaining amount being up to 100% by weight. Upon dilution with water, an emulsion is obtained.

[0706] iv) Emulsions (EW, EO, ES) 5 to 40% by weight of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicide compound B (component B) according to the present invention and safener C (component C), and 1 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is introduced into the remaining amount of water up to 100% by weight using an emulsifier to form a homogeneous emulsion. Dilution with water results in an emulsion.

[0707] v) Suspension (SC, OD, FS) 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 herbicidal compound B (component B) and antidote C (component C), is ground to a finely divided active substance suspension with the addition of 2 to 10% by weight of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylates), 0.1 to 2% by weight of a thickener (e.g., xanthan gum), and the remaining amount of water up to 100% by weight. Upon dilution with water, a stable suspension of the active substance is obtained. For FS-type formulations, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0708] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50 to 80% by weight of a compound of formula (I) according to the invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and antidote C (component C), is milled with the addition of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylate) in a remaining amount up to 100% by weight, and prepared as water-dispersible or water-soluble granules by means of technical equipment (e.g., extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0709] vii) Water-dispersible and water-soluble powders (WP, SP, WS) 50-80% by weight of a compound of formula (I) according to the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and antidote C (component C), is ground in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g., sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate), and 100% by weight of a solid carrier (e.g., silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

[0710] viii) Gel (GW, GF) 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 herbicidal compound B (component B) and antidote C (component C), is ground with 3 to 10% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 5% by weight of a thickener (e.g., carboxymethylcellulose), and the remaining amount of water up to 100% by weight to obtain a fine suspension of the active substance. Upon dilution with water, a stable suspension of the active substance is obtained.

[0711] iv) Microemulsion (ME) To 5-20% by weight of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from herbicide compound B (component B) and safener C (component C) according to the invention, 5-30% by weight of a blend of organic solvents (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a blend of surfactants (e.g., alcohol ethoxylate and arylphenol ethoxylate), and water to make up 100%. The mixture is stirred for 1 hour, and a thermodynamically stable microemulsion spontaneously forms.

[0712] iv) Microcapsules (CS) An oil phase containing 5 to 50% by weight of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one additional compound selected from herbicide compound B (component B) and safener C (component C) according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2 to 15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization is initiated with a radical initiator to form poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5 to 50% by weight of a compound of formula (I) according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Polyurea microcapsules are formed by adding a polyamine (e.g., hexamethylenediamine). The amount of the monomer is 1-10% by weight. The weight % is based on the total CS formulation.

[0713] ix) Powder (DP, DS) 1 to 10% by weight of a compound of formula (I) or a combination of at least one compound of formula (I) (component A) with at least one further compound selected from herbicide compound B (component B) and safener C (component C) according to the invention is finely ground and intimately mixed with a solid carrier (e.g. finely divided kaolin) to make up 100% by weight.

[0714] x) Granules (GR, FG) 0.5 to 30% by weight of a compound of formula (I) or a combination of at least one compound of formula (I) (component A) with at least one further compound selected from herbicide compound B (component B) and safener C (component C) according to the invention is finely ground and combined with a total of 100% by weight of a solid carrier (e.g., silicate). Granulation is carried out by extrusion, spray drying or fluidized bed.

[0715] xi) Ultra-low volume liquid (UL) 1 to 50% by weight of a compound of formula (I) or a combination of at least one compound of formula (I) (component A) with at least one further compound selected from a herbicide compound B (component B) according to the invention and a safener C (component C) is dissolved in an organic solvent (e.g., an aromatic hydrocarbon) to make up 100% by weight.

[0716] Formulations of types i) to xi) may optionally contain further adjuvants, for example 0.1 to 1% by weight of a bactericide, 5 to 15% by weight of an antifreeze agent, 0.1 to 1% by weight of an antifoaming agent and 0.1 to 1% by weight of a colorant.

[0717] The formulations and / or combinations generally contain 0.01 to 95% by weight, preferably 0.1 to 90% by weight, in particular 0.5 to 75% by weight, of a compound of formula (I).

[0718] The compound of formula (I) is used with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

[0719] For the treatment of plant seeds, especially seeds, seed treatment solutions (LS), emulsions (SE), flowable formulations (FS), dry seed treatment powders (DS), wettable powders for seed treatment (WS), water-soluble powders for seed treatment (SS), seed treatment emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF) are usually used. The preparations in question are diluted 2 to 10 times to obtain ready-to-use preparations with an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40% by weight.

[0720] Methods for applying the compounds of formula (I), formulations and / or combinations thereof to plant seeds, particularly seeds, include dressing, covering, pelleting, dusting, soaking and furrow application to the seeds. Preferably, the compounds of formula (I), formulations and / or combinations thereof are applied to the plant seeds in a manner that does not induce germination, such as seed dressing, pelleting, coating and dusting, respectively.

[0721] To the compounds of formula (I), formulations and / or combinations containing them, various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, antidotes) can be added as premixes or, if appropriate, can be added only immediately before use (tank mix). These agents can be mixed with the formulations according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0722] The user typically applies the compounds of formula (I) according to the invention, formulations and / or combinations containing them from a pre-dosing device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation device. Typically, the formulation is brought to the desired application concentration with water, buffers, and / or further adjuvants, thus obtaining a ready-to-use spray solution or a formulation according to the invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray solution are applied per hectare of agriculturally useful area.

[0723] According to one embodiment, either the individual or partially premixed components of the formulation according to the invention, for example the components comprising a compound of formula (I) and optionally an active substance from group B and / or C, are mixed by the user in a spray tank, and further auxiliaries and additives may be added, if appropriate.

[0724] In a further embodiment, the individual components of the formulation according to the invention, such as parts of a kit or parts of a two- or three-component mixture, are mixed by the user himself in a spray tank, and further auxiliaries may be added if appropriate.

[0725] In a further embodiment, any of the individual or partially premixed components of the formulation according to the invention, e.g. components comprising a compound of formula (I) and optionally an active substance from group B and / or C, can be applied together (e.g. after a tank mix) or sequentially.

[0726] The compounds of formula (I) are suitable as herbicides, either on their own or in suitable combination with at least one further compound selected from herbicidally active compound B (component B) and antidote C (component C).

[0727] The compounds of formula (I) or formulations and / or combinations containing the compounds of formula (I) provide highly effective control of undesirable vegetation in non-crop lands, especially at high application rates. They act against broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing significant damage to the crop plants. This effect is mainly observed at low application rates.

[0728] The compounds of the present invention are useful, for example, for controlling the following weeds: representative examples include velvetleaf (Abutilon theophrasti) (ABUTH), black-grass (Alopercurus myosuroides) (ALOMY), redroot pigweed (Amaranthus retroflexus) (AMARE), common branweed (Apera spica-venti) (APESV), wild oat (Avena fatua) (AVEFA), barnyardgrass (Echinocloa crus-galli) (ECHCG), foxtail (Setaria faberi) (SETFA), and green foxtail (Setaria viridis) (SETVI).

[0729] The compounds of formula (I) or formulations and / or combinations containing them are applied to plants primarily by spraying onto the leaves. Application can be carried out by conventional spraying techniques, for example using water as a carrier and a spray volume of about 100 to 1000 l / ha (e.g., 300 to 400 l / ha). The compounds of formula (I) or formulations and / or combinations containing them may also be applied by low-volume or ultra-low-volume methods or in the form of fine particles.

[0730] Application of the compounds of formula (I), or formulations and / or combinations containing them, may be carried out before, during and / or after the emergence of the undesired vegetation, preferably during and / or after the emergence.

[0731] The application of the compounds of formula (I), or the formulations and / or combinations, can be carried out before or during sowing.

[0732] The compounds of formula (I), or formulations and / or combinations containing them, can be applied pre-emergence, post-emergence, or pre-planting, or together with the seeds of crop plants. It is also possible to apply the compounds of formula (I), or formulations and / or combinations containing them, by applying the seeds of crop plants that have been pre-treated with the compounds of formula (I), or formulations and / or combinations containing them. If the active ingredient is poorly tolerated by a particular crop plant, a post-direct application technique (lay-by) can be used in which the combination is sprayed with the aid of a spraying device so as to avoid contact with the leaves of sensitive crop plants as much as possible, but the active ingredient reaches the leaves of underlying undesirable vegetation or the bare soil surface.

[0733] In a further embodiment, the compound of formula (I) or the formulations and / or combinations comprising them can be applied by treating seeds. Seed treatment essentially includes all procedures known to those skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi-coating, seed envelopment, seed dripping and seed pelleting) based on the compound of formula (I) or the formulations and / or combinations prepared therefrom. Here, the combination can be applied diluted or undiluted.

[0734] The term "seed" includes all kinds of seeds, such as corn, seeds, fruits, tubers, seedlings and similar forms. Preferably, the term seed here describes corn and seeds. The seeds used can be seeds of the above-mentioned crop plants, but can also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0735] When used in plant protection, the application rates of the active substance without formulation auxiliaries, i.e. the compound of formula (I), component B and, where appropriate, component C, are, depending on the type of effect desired, between 0.001 and 2 kg, preferably between 0.005 and 2 kg, more preferably between 0.05 and 0.9 kg, in particular between 0.1 and 0.75 kg per hectare.

[0736] In another embodiment of the invention, the application rates of the compound of formula (I), component B and, where 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).

[0737] 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 0.1 g / ha to 3000 g / ha, preferably 10 g / ha to 1000 g / ha, depending on the target to be controlled, the season, the target plant, and the growth stage.

[0738] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is in the range of 0.1 g / ha to 5000 g / ha, preferably in the range of 1 g / ha to 2500 g / ha or 5 g / ha to 2000 g / ha.

[0739] 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.

[0740] The required application rate of herbicidal compound B is generally in the range of 0.0005 kg / ha to 2.5 kg / ha, preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / h as.

[0741] The required application rate of Antidote C is generally in the range of 0.0005 kg / ha to 2.5 kg / ha, preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / h as.

[0742] In the treatment of plant seeds and other seedlings, for example by dusting, coating or irrigating seeds, the amount of active substance required is generally 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g per 100 kilograms of plant seeds and seedlings (preferably seeds).

[0743] In another embodiment of the invention, for treating seeds, the application rate of active substances, i.e. the compound of formula (I), component B and, where appropriate, component C, is generally employed in an amount of 0.001 to 10 kg per 100 kg of seeds.

[0744] When used in the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0745] In the case of the combinations according to the invention, it is immaterial whether the compound of formula (I) and the further component B and / or component C are formulated and applied together or applied separately.

[0746] If applied separately, it is not important in what order the applications are carried out: it is only necessary that the compound of formula (I) and the further component B and / or component C are applied in a time frame that allows the simultaneous action of the active ingredients on the plant, preferably within a time frame of at most 14 days, in particular at most 7 days.

[0747] Depending on the application method, the compounds of formula (I), or formulations and / or combinations containing them, can be additionally applied to many more crop plants to eliminate undesirable vegetation. Examples of suitable crops include: Onion (Allium cepa), pineapple (Ananas comosus), groundnut (Arachis hypogaea), asparagus (Asparagus officinalis), oats (Avena sativa), beet (Beta vulgaris spec. altissima), beet (Beta vulgaris spec. rapa), rapeseed (Brassica napus var. napus), rutabaga (Brassica napus var. napobrassica), and winter tuna rape (Brassica rapa var.silvestris, kale (Brassica oleracea), black mustard (Brassica nigra), tea plant (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Carya illinoinensis), lemon (Citrus limon), orange (Citrus sinensis), Arabica coffee (Coffea arabica), Robusta coffee (Coffea canephora), Liberica coffee (Coffea liberica), cucumber (Cucumis sativus), corngrass (Cynodon dactylon), wild carrot (Daucus carota), oil palm (Elaeis guineensis), wild strawberry (Fragaria vesca), soybean (Glycine max), and upland cotton (Gossypium hirsutum, green cotton (Gossypium arboreum), Asiatic cotton (Gossypium herbaceum), Gossypium vitifolium, sunflower (Helianthus annuus), rubber tree (Hevea brasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), oak walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), musa (Musa spec.), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), Norway spruce (Picea abies), pine (Pinus spec.), pistachio (Pistacia vera), pea (Pisum sativum), sweet cherry (Prunus avium), peach (Prunus persica), pear (Pyrus communis), apricot (Prunus armeniaca), black cherry (Prunus cerasus), almond (Prunus dulcis) and plum (Prunus domestica), Ribes sylvestre, castor bean (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis alba), potato (Solanum tuberosum), sorghum (Sorghum bicolor (S. vulgare)), cocoa (Theobroma cacao) cacao), red clover (Trifolium pratense), bread wheat (Triticum aestivum), triticale (Triticale), durum wheat (Triticum durum), broad beans (Vicia faba), European grape (Vitis vinifera), and corn (Zea mays).

[0748] Preferred crops include peanut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), kale (Brassica oleracea), lemon (Citrus limon), orange (Citrus sinensis), coffee (Coffea arabica), coffee (Coffea canephora), coffee (Coffea liberica), corngrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum), green cotton (Gossypium arboreum), and Asiatic cotton (Gossypium herbaceum, Gossypium vitifolium, sunflower (Helianthus annuus), barley (Hordeum vulgare), oak walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), pistachio (Pistacia vera), pea (Pisum sativum), almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor (s. grugare (s.vulgare), triticale (Triticale), bread wheat (Triticum aestivum), durum wheat (Triticum durum), broad beans (Vicia faba), European grape (Vitis vinifera), and corn (Zea mays).

[0749] Particularly preferred crops are cereals, corn, soybeans, rice, rapeseed, cotton, potato, peanut or perennial crops.

[0750] The compounds of formula (I) according to the present invention, or formulations and / or combinations comprising them, may also be used in crop plants that have been modified by mutagenesis or genetic engineering in order to provide the plants with new traits or to modify traits that are already present.

[0751] As used herein, the term "crop plant" also includes (crop) plants that have been modified by mutagenesis or genetic engineering to provide the plant with new traits or to modify traits that are already present.

[0752] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis to generate mutations at specific loci in the plant genome, which often use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases to achieve the targeted effect.

[0753] Genetic engineering typically uses recombinant DNA technology to create modifications in plant genomes that are not readily obtainable through breeding, mutation, or natural recombination in natural environments. Typically, one or more genes are incorporated into a plant's genome to add or improve a trait. These incorporated genes are also known in the art as transgenes, and plants containing such transgenes are called transgenic plants. During plant transformation, several transformation events typically occur, each with a different genomic locus at which the transgene is integrated. Plants containing a particular transgene at a particular genomic locus are typically described as containing a particular "event" and are referred to by the name of that event. Traits introduced or modified in plants include herbicide tolerance, insect resistance, increased yield, and tolerance to biotic conditions such as drought, among others.

[0754] Herbicide tolerance has been engineered using mutations as well as genetic modification. Plants that have been made tolerant to acetolactate synthase (ALS)-inhibiting herbicides by traditional mutagenesis and breeding methods include plant varieties marketed under the name Clearfield®. However, most herbicide tolerance traits have been engineered using transgenes.

[0755] Herbicide tolerance has been engineered to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isoxaflutole and mesotrione.

[0756] Transgenes used to provide herbicide tolerance traits include: tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, and goxv247; tolerance to glufosinate: pat and bar; tolerance to 2,4-D: aad-1 and aad-12; tolerance to dicamba: dmo; tolerance to oxynil herbicides: bxn; tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; tolerance to ALS inhibitor herbicides: csr1-2; tolerance to HPPD inhibitors: hppdPF, W336, and adhppd-03.

[0757] Transgenic corn events containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275.

[0758] Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, 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, SYHTφH2, W62, W98, FG72, and CV127.

[0759] Transgenic cotton events containing herbicide resistance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40.

[0760] Transgenic canola events containing herbicide tolerance genes include, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0761] Insect resistance has primarily been achieved by introducing bacterial genes encoding insecticidal proteins into plants. The most frequently used transgenes are Bacillus species toxin genes and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes have also been introduced into other plants, particularly genes encoding protease inhibitors such as CpTI and pinII. Another approach involves using transgenes to produce double-stranded RNA in plants to target and downregulate insect genes. An example of such a transgene is dvsnf7.

[0762] Transgenic corn events containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098.

[0763] Transgenic soybean events containing genes for insecticidal proteins are, for example, but not exclusive of, MON87701, MON87751 and DAS-81419.

[0764] Transgenic cotton events containing genes for insecticidal proteins include, but are not limited to, 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.

[0765] Increasing panicle biomass using the transgene athb17 present in corn event MON87403 or enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712 results in increased yield.

[0766] The transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A have been used to create crops with improved oil content. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[0767] Tolerance to abiotic conditions, particularly drought tolerance, has been conferred by using the transgene cspB contained in the maize event MON87460 and by using the transgene Hahb-4 contained in the soybean event IND-φφ41φ-5.

[0768] Trait combinations are often achieved by combining genes contained in transformation events or by combining different events during breeding. Preferred trait combinations are herbicide resistance to different groups of herbicides, insect resistance to different types of insects, especially resistance to lepidopteran and coleopteran insects, herbicide resistance and resistance to one or more insects, herbicide resistance and increased yield, and herbicide resistance and tolerance to abiotic conditions.

[0769] Plants containing single or stacked traits, as well as the genes and events that confer these traits, are well known in the art. For example, detailed information about mutated or integrated genes and their respective events is available from the websites of the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase), as well as from patent applications such as EP 3028573 and WO 2017 / 011288.

[0770] The use of compounds of formula (I) according to the present invention or formulations or combinations containing them in crops may result in effects specific to the crop containing a particular gene or event. These effects may include changes in growth behavior or resistance to biotic or abiotic stress factors. Such effects may include, inter alia, increased yield, resistance or improved tolerance to insect, nematode, fungal, bacterial, mycoplasmal, viral or viroid pathogens, early vigor, early or late maturity, low or high temperature tolerance, and changes in amino acid or fatty acid spectrum or content.

[0771] Furthermore, plants whose ingredient content has been adjusted or new ingredients have been added using recombinant DNA techniques, particularly to improve the yield of the raw material, such as potatoes with increased amylopectin production (e.g., Amflora® potatoes, BASF SE, Germany).

[0772] Furthermore, it has been found that the compounds of formula (I) according to the invention or formulations and / or combinations comprising them are also suitable for defoliating and / or desiccating plant parts of crop plants such as cotton, potato, rapeseed, sunflower, soybean or broad bean, in particular cotton. In this connection, formulations and / or combinations for desiccating and / or defoliating crops, processes for preparing said formulations and / or combinations and methods for desiccating and / or defoliating plants using compounds of formula (I) have been found.

[0773] The compounds of formula (I) as desiccants are particularly suitable for drying the above-ground parts of crop plants such as potato, rapeseed, sunflower and soybean as well as cereals, thereby allowing the complete mechanical harvesting of these important crop plants.

[0774] There is also economic interest in facilitating yields by concentrating within a certain time period the reduction of dehiscence or attachment to the tree of seeds and varieties of citrus fruits, olives, and other pernicious fruits, drupes, and nuts. The same mechanism, i.e., the promotion of the development of an abscission layer between the fruit or leaf and shoot of the plant, is also essential for regulating defoliation of useful plants, particularly cotton.

[0775] Additionally, shortening the time it takes for individual cotton plants to mature improves the quality of the fiber after harvest. [Example]

[0776] A. Synthesis Examples Chemical bonds depicted as bars in chemical formulas represent the relative configurations on the ring systems.

[0777] Example 1: Synthesis of 3-[[(1R,4S)-4-isopropoxycarbonylcyclopent-2-en-1-yl]amino]-2-methoxy-3-oxo-propanoic acid (Inter A) [ka] To a solution of (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (CAS 79200-56-9) (33.3 g, 305 mmol) (3.0 g, 24 mmol) in isopropanol (100 mL) was added thionyl chloride (72.6 g, 610 mmol) at 0° C. After stirring for 2 h and allowing the mixture to warm to room temperature, the solvent was removed under reduced pressure to give Inter C (54 g, 86%) as a colorless salt. 1H NMR(400MHz,D2O)δ 6.23(ddd,J=5.7,2.4,1.6Hz,1H),5.99(dt,J=5.7,2.3Hz,1H),5.03(hept,J=6.2Hz,1H),4.42(ddt,J=6.7,4.9,1.9Hz,1H),3. 75(dddd,J=10.4,4.1,3.3,2.0Hz,1H),2.70(dt,J=14.4,8.5Hz,1H),2.08(dt,J=14.4,5.2Hz,1H),1.28(dd,J=6.3,3.0Hz,6H). [ka] To a solution of lithium 2,3-dimethoxy-3-oxopropanoate (3) (37.5 g, 243 mmol) in dimethylformamide (DMF, 250 mL) was added isopropyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate (2) (50 g, 243 mmol) (CAS 229613-83-6) hydrochloride salt. To the resulting solution was added HATU (101 g, 729 mmol) (CAS: 148893-10-1), followed by diisopropylethylamine (124 mL). After stirring overnight, the reaction was quenched with water (50 mL) and saturated aqueous dicarbonate solution (50 mL). The aqueous layer was separated and extracted with ethyl acetate (3 × 100 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The crude product (4) (72 g, 99%) was obtained as a 1:1 mixture of diastereoisomers and was used in the next step without further purification. 1 H NMR (500 MHz, chloroform-d) δ 7.10-6.98 (m, 1H), 5.98-5.79 (m, 2H), 5.13-4.97 (m, 2H), 4.34-4.25 (m, 1H), 3.83 (s, 3H), 3.56-3.44 (m, 4H), 2.55-2.41 (m, 1H), 1.96-1.85 (m, 1H), 1.29-1.23 (m, 6H). [ka] To a solution of isopropyl (1S,4R)-4-[(2,3-dimethoxy-3-oxo-propanoyl)amino]cyclopent-2-ene-1-carboxylate (4) (21.1 g, 70.5 mmol) in 1,2-dichloroethane (200 mL), trimethyltin hydroxide (MeSnOH) (25.5 g, 141 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 16 hours, after which the reaction mixture was extracted with saturated aqueous sodium bicarbonate in water (3 × 100 mL). The combined organic phase was adjusted to pH 1 with concentrated aqueous hydrogen chloride. The resulting mixture was extracted with ethyl acetate (3 × 100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to give 3-[[(1R,4S)-4-isopropoxycarbonylcyclopent-2-en-1-yl]amino]-2-methoxy-3-oxo-propanoic acid (20 g, quantitative) as a mixture of diastereoisomers (1:1). 1 H NMR (500 MHz, chloroform-d) δ 9.64 (s, 1H), 7.65-7.43 (m, 1H), 6.05-5.79 (m, 2H), 5.13-4.96 (m, 2H), 4.32 (s, 1H), 3.70-3.60 (m, 3H), 3.55-3.45 (m, 1H), 2.55-2.41 (m, 1H), 2.01-1.89 (m, 1H), 1.31-1.21 (m, 6H).

[0778] Example 2: Synthesis of isopropyl (1S,4R)-4-[[3-[(5-tert-butylisoxazol-3-yl)amino]-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd.I.1 in Table 1 below): [ka] To a solution of Inter A (300 mg, 1.05 mmol) in dimethylformamide (DMF, 5 mL) was added 5-tert-butylisoxazol-3-amine (1) (50 g, 243 mmol) (CAS [55809-36-4]). To the resulting solution was added HATU (460 mg, 1.21 mmol) (CAS: 148893-10-1) and diisopropylethylamine (0.36 mL, 2.1 mmol). After stirring overnight, the reaction was quenched with water (5 mL) and saturated aqueous dicarbonate solution (5 mL). The aqueous layer was separated and extracted with ethyl acetate (3 × 10 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The residue was purified by column chromatography using ethyl acetate to give the title compound (40 mg, 9%) as a 1:1 mixture of diastereoisomers. 1 H NMR (500 MHz, THF-d) δ 10.20-10.09(m,1H),7.46(t,J=7.7Hz,1H),6.69(d,J=2.2Hz,1H),5.84(ddd t,J=50.0,7.7,5.6,2.5Hz,2H),4.98(ddtd,J=15.4,12.5,6.3,2.4Hz,2H),4 .32(d,J=3.4Hz,1H),3.49-3.41(m,4H),2.47(dtd,J=13.4,8.3,5.0Hz,1H), 1.85(dtd,J=13.4,5.6,3.5Hz,1H),1.32(s,9H),1.23(dd,J=6.3,3.7Hz,6H).

[0779] Example 3: Synthesis of isopropyl (1S,4R)-4-[[3-[(4-chloro-2-pyridyl)amino]-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd.I.4 in Table 1 below): [ka] A solution of 1-propanephosphonic anhydride (T3P) (1.14 g, 1.79 mmol, 50% in ethyl acetate) and triethylamine (0.44 mL, 3.2 mmol) was added to a solution of 3-[[(1R,4S)-4-isopropoxycarbonylcyclopent-2-en-1-yl]amino]-2-methoxy-3-oxo-propanoic acid (Inter A) (300 mg, 1.05 mmol) and 4-chloropyridin-2-amine (1) (149 mg, 1.26 mmol) in tetrahydrofuran (30 mL). After stirring overnight at room temperature, the mixture was poured into ice water and extracted with ethyl acetate (three times). The extract was washed with brine, dried, concentrated, and purified by column chromatography using ethyl acetate as the solvent to give the title compound Cpd I.4 (290 mg, 66% yield) as a 1:1 mixture of diastereoisomers. 1 H NMR(400MHz,chloroform-d)δ 9.58-9.47(m,1H),8.26(d,J=1.9Hz,1H),8.23-8.15(m,1H),7.39-7.27(m,1H),7.11-6.99(m,1H),5.98-5.80(m,2H),5.16-4 .96(m,2H),4.46-4.37(m,1H),3.68-3.57(m,3H),3.53-3.45(m,1H),2.53-2.41(m,1H),2.01-1.87(m,1H),1.32-1.16(m,6H).

[0780] Example 4: Synthesis of isopropyl (1S,4R)-4-[[3-[(2-chloro-6-methyl-4-pyridyl)amino]-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd.I.6 in Table 1 below): [ka] A solution of 1-propanephosphonic anhydride (T3P) (1.14 g, 1.79 mmol, 50% in ethyl acetate) and triethylamine (0.44 mL, 3.2 mmol) was added to a solution of 3-[[(1R,4S)-4-isopropoxycarbonylcyclopent-2-en-1-yl]amino]-2-methoxy-3-oxo-propanoic acid (Inter A) (300 mg, 1.05 mmol) and 2-chloro-6-methyl-pyridin-4-amine (1) (165 mg, 1.16 mmol) in tetrahydrofuran (30 mL). After stirring overnight at room temperature, the mixture was poured into ice water and extracted with ethyl acetate (three times). The extract was washed with brine, dried, concentrated, and purified by column chromatography using ethyl acetate as the solvent to give the title compound Cpd I.6 (290 mg, 66% yield) as a 1:1 mixture of diastereoisomers. 1 H NMR(400MHz,chloroform-d)δ 9.81-9.60(m,1H),7.58-7.42(m,2H),7.35-7.20(m,1H),6.05-5.80(m,2H),5.15-4.94(m,2H), 4.50-4.41(m,1H),3.65-3.45(m,4H),2.55-2.16(m,4H),2.08-1.94(m,1H),1.36-1.14(m,6H).

[0781] Example 5: Synthesis of isopropyl (1S,4R)-4-[[3-[(4-chloro-2-thienyl)amino]-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd.I.20): [ka] To a solution of Inter A (200 mg, 0.701 mmol) in dimethylformamide (DMF, 5 mL) was added 4-chlorothiophene-2-amine (1) (137 mg, 0.806 mmol). To the resulting solution were added HATU (307 mg, 0.806 mmol) (CAS: 148893-10-1) and diisopropylethylamine (0.24 mL, 1.4 mmol). After stirring overnight, the reaction was quenched with water (5 mL) and saturated aqueous dicarbonate solution (5 mL). The aqueous layer was separated and extracted with ethyl acetate (3 × 10 mL). The combined organic phases were dried (sodium sulfate), filtered, and evaporated under reduced pressure. The residue was purified by column chromatography using ethyl acetate to give the title compound Cpd.I.20 (60 mg, 21%) as a 1:1 mixture of diastereoisomers. 1 H NMR(500MHz,chloroform-d)δ 9.09-8.96(m,1H),7.32-7.28(m,1H),7.24-7.17(m,1H),6.97-6.93(m,1H),5.99-5.80(m,2H),5.10-4.95(m,2H), 4.27-4.21(m,1H),3.69-3.60(m,3H),3.52-3.42(m,1H),2.53-2.38(m,1H),1.98-1.87(m,1H),1.28-1.19(m,6H).

[0782] High performance liquid chromatography: HPLC-column Kinetex XB C18 1.7μ (50×2.1 mm); eluent: acetonitrile / water+0.1% trifluoroacetic acid (60° C., gradient from 5:95 to 100:0 in 1.5 min, flow gradient from 0.8 to 1.0 ml / min in 1.5 min).

[0783] Similar to the previous example, R 1 and R 4 The following compounds of formula (I) where is hydrogen were prepared starting from commercially available diesters and using commercially available amines: [ka]

[0784] [Table 84]

[0785] [Table 85]

[0786] [Table 86]

[0787] [Table 87]

[0788] [Table 88]

[0789] [Table 89]

[0790] B. Biological Examples The herbicidal activity of the compounds of formula (I) was demonstrated in the following greenhouse experiments:

[0791] Plastic flower pots were used as culture medium containers, and loamy sandy soil containing about 3.0% humus was placed as a substrate. Seeds of the test plants were sown according to species.

[0792] For pre-emergence treatment, the active ingredient was suspended or emulsified in water and applied using a finely distributing nozzle directly after sowing. To promote germination and growth, the containers were gently watered and then covered with a transparent plastic hood until the test plants had rooted. This cover allowed the test plants to emerge uniformly, unless adversely affected by the active ingredient.

[0793] For post-emergence treatment, the test plants were first grown to a height of 3-15 cm, depending on the plant habit, and only then were they treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same container, or grown separately as seedlings and transplanted into the test containers a few days before treatment.

[0794] Test plants were maintained at 10 to 25°C or 20 to 35°C, depending on the variety.

[0795] The test period lasted from 2 to 4 weeks, during which the test plants were cared for and their response to each treatment was evaluated.

[0796] The ratings were made on a scale of 0 to 100, with 100 meaning that the test plants had not emerged or at least the above-ground parts had been completely destroyed, and 0 meaning that the plants were undamaged and in a normal state of growth. A value of 70 to <90 indicates high herbicidal activity, and a value of 90 to 100 indicates very high herbicidal activity.

[0797] The test plant species used in the greenhouse experiments were as follows:

[0798] [Table 90]

[0799] Applied by pre-emergence method at an application rate of 0.125 kg / ha: Compounds I.1 and I.16 showed very good herbicidal activity against AMARE.

[0800] Applied by post-emergence method at an application rate of 0.125 kg / ha: Compound I.11 showed good herbicidal activity against ALOMY. Compound I.11 showed good herbicidal activity against AVEFA.

[0801] Applied by pre-emergence method at an application rate of 0.250 kg / ha: Compound I.13 showed very good herbicidal activity against ABUTH. Compound I.20 showed very good herbicidal activity against AMARE. Compounds I.19 and I.23 showed high herbicidal activity against AMARE. Compounds I.3, I.13, I.18, I.20, I.21, and I.25 showed very high herbicidal activity against APESV. Compounds I.19, I.22, and I.23 showed good herbicidal activity against APESV. Compounds I.20, I.21 and I.25 showed very good herbicidal activity against ECHCG. Compound I.7 showed good herbicidal activity against ECHCG. Compound I.25 showed very good herbicidal activity against SETFA.

[0802] Applied by post-emergence method at an application rate of 0.250 kg / ha: Compounds I.7, I.13, I.14, I.20 and I.21 showed very good herbicidal activity against ABUTH. Compounds I.4, I.5, I.6, I.9, I.12, I.15, I.22, I.23, and I.25 showed good herbicidal activity against ABUTH. Compounds I.4, I.5, I.8, I.14, I.25, and I.35 showed very high herbicidal activity against ALOMY. Compounds I.2, I.9, I.12, I.20, I.38, and I.40 showed good herbicidal activity against ALOMY. Compounds I.13, I.18, I.35 and I.36 showed very good herbicidal activity against AMARE. Compounds I.4, I.6, I.9, I.18, and I.36 showed very good herbicidal activity against AVEFA. Compounds I.3, I.5, I.23, I.38, I.39, I.40, and I.41 showed good herbicidal activity against AVEFA. Compounds I.7, I.8, I.13, I.14, I.21, I.35, I.36, and I.39 showed very good herbicidal activity against ECHCG. Compound I.3 showed good herbicidal activity against ECHCG. Compounds I.3, I.6, I.7, I.18, I.21, I.38, and I.41 showed very good herbicidal activity against SETVI. Compounds I.8, I.23, I.25, I.39, and I.40 showed good herbicidal activity against SETVI.

Claims

1. Formula (I) 【Chemical 1】 wherein the substituents have the meanings given below: Q is a 5- or 6-membered heteroaromatic ring containing, as ring members, 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S, and the ring is Ｑ１ and n substituents R Ｑ２ having R Ｑ１ is a halogen, nitro, hydroxyl, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, hydroxy-(C １ ~C ３ )-alkyl, (C ３ ~C ５ )-cycloalkyl, (C １ ~C ３ )-alkoxy, (C １ ~C ３ )-haloalkoxy, (C ２ ~C ３ )-alkenyl, (C ２ ~C ３ )-haloalkenyl, (C ２ ~C ３ )-alkynyl or (C ２ ~C ３ )-haloalkynyl; R Ｑ２ is phenyl-(C １ ~C ３ )-alkyl, (C １ ~C ４ )-alkylcarbonyl, aminocarbonyl, (C １ ~C ４ )-alkylaminocarbonyl, di-(C １ ~C ４ -alkyl)aminocarbonyl, (C １ ~C ４ )-alkoxycarbonyl, benzyloxycarbonyl, fluorenyloxycarbonyl, allyloxycarbonyl, (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ )-alkylsulfonyl or phenylsulfonyl, in which the aliphatic or aromatic moiety in the last-mentioned 14 groups is fluorine, chlorine, bromine, cyano, and (C １ ~C ２ )-alkoxy; R １ is hydrogen, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C ３ ~C ４ )-cycloalkyl, (C ２ ~C ３ )-alkenyl, (C ２ ~C ３ )-haloalkenyl, (C ２ ~C ３ )-alkynyl, (C ２ ~C ３ )-haloalkynyl, (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, (C １ ~C ３ )-alkoxy, (C １ ~C ３ )-haloalkoxy or (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkoxy; R ２ is (C １ ~C ６ )-alkyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-alkenyl, (C ３ ~C ６ )-alkynyl, or (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, wherein the aliphatic or cycloaliphatic portion of the last-mentioned five groups is substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; R ３ is hydrogen, halogen, cyano, (C １ ~C ６ )-alkyl, (C １ ~C ６ )-haloalkyl, (C １ ~C ６ )-cyanoalkyl, (C １ ~C ３ )-hydroxyalkyl, (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkoxy-(C １ ~C ３ )-alkyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-alkenyl, (C ２ ~C ６ )-alkynyl, (C １ ~C ６ )-alkoxy, (C １ ~C ６ )-haloalkoxy, (C １ ~C ３ )-cyanoalkoxy, (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkoxy, (C ３ ~C ６ )-cycloalkoxy, (C ３ ~C ５ )-cycloalkyl-(C １ ~C ３ )-alkoxy, (C ３ ~C ６ )-alkenyloxy, (C ３ ~C ６ )-alkynyloxy or (C １ ~C ３ )-alkylthio; R ４ is hydrogen, (C １ ~C ６ )-alkyl, (C １ ~C ６ )-haloalkyl, (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, (C ３ ~C ４ )-cycloalkyl, (C ２ ~C ６ )-alkenyl, (C ２ ~C ６ )-haloalkenyl, (C ２ ~C ６ )-alkynyl, (C ２ ~C ６ )-haloalkynyl, (C １ ~C ６ )-alkoxy, (C １ ~C ６ )-haloalkoxy or (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkoxy; X is a bond (X ０ ) or (X １ ), (X ２ ), (X ３ ), (X ４ ), (X ５ ) and (X ６ ) is a divalent entity selected from the group consisting of: 【Chemistry 2】 R ５ , R ６ , R ７ , R ８ , R ９ and R １０ are each independently and independently at each occurrence hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ２ R ｅ , C.O.R. ｂ R ｄ , N.R. ｂ CO ２ R ｅ , R ａ ; (C １ ~C ６ )-alkyl, (C ３ ~C ５ )-cycloalkyl, (C ２ ~C ６ )-alkenyl, (C ２ ~C ６ ) -alkynyl, phenyl, imidazolyl (the last six aliphatic, cycloaliphatic, aromatic or heteroaromatic groups being substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano); (C １ ~C ６ )-alkoxy, (C ３ ~C ６ )-cycloalkoxy, (C ３ ~C ６ )-alkenyloxy, (C ３ ~C ６ )-alkynyloxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl or (C １ ~C ３ )-alkylsulfonyl (the aliphatic or cycloaliphatic portion of the last seven groups is fluorine, chlorine, bromine, iodine, cyano and (C １ ~C ２ )-alkoxy; Y is hydrogen, cyano, hydroxyl, Z; (C １ ~C １２ )-alkyl, (C ３ ~C ８ )-cycloalkyl, (C ２ ~C １２ )-alkenyl or (C ２ ~C １２ )-alkynyl (the last four aliphatic or cycloaliphatic groups are fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR ｄ ,Z,OZ,NHZ,S(O) ｎ R ａ , S.O. ２ NR ｂ R ｄ , S.O. ２ NR ｂ COR ｅ , CO ２ R ｅ , C.O.R. ｂ R ｈ , C.O.R. ｂ , C.O.R. ｅ SO ２ R ａ , N.R. ｂ R ｅ , N.R. ｂ COR ｅ , N.R. ｂ CONR ｅ R ｅ , N.R. ｂ CO ２ R ｅ , N.R. ｂ SO ２ R ｅ , N.R. ｂ SO ２ NR ｂ R ｅ , OCONR ｂ R ｅ , OCSNR ｂ R ｅ , P.O.R. ｆ R ｆ and C(R ｂ ) = NOR ｅ and m groups selected from the group consisting of: Z is formed from r carbon atoms, k nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ２ R ｅ , C.O.R. ｂ R ｈ , S(O) ｎ R ａ , S.O. ２ NR ｂ R ｄ , S.O. ２ NR ｂ COR ｅ , C.O.R. ｂ , C.O.R. ｅ SO ２ R ａ , N.R. ｂ R ｅ , N.R. ｂ COR ｅ , N.R. ｂ CONR ｅ R ｅ , N.R. ｂ CO ２ R ｅ , N.R. ｂ SO ２ R ｅ , N.R. ｂ SO ２ NR ｂ R ｅ , OCONR ｂ R ｅ , OCSNR ｂ R ｅ , P.O.R. ｆ R ｆ and C(R ｂ ) = NOR ｅ , R ａ , R ｃ , R ｅ and R ｆ wherein the sulfur and carbon atoms are substituted with m groups selected from the group consisting of: R ａ is (C １ ~C ６ )-alkyl, (C ２ ~C ４ )-alkynyl or (C ３ ~C ６ )-cycloalkyl (the last three aliphatic or cycloaliphatic groups are fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C １ ~C ３ )-alkoxy; R ｂ are hydrogen or independently R ａ has one of the meanings given for R ｃ represents fluorine, chlorine, bromine, iodine, cyano, hydroxyl; １ ~C ６ )-alkoxy, (C ３ ~C ６ )-alkenyloxy or (C ３ ~C ６ )-alkynyloxy (the aliphatic portion of the last three groups is fluorine, chlorine, bromine, cyano and (C １ ~C ２ )-alkoxy; R ｄ is hydrogen, (C １ ~C ６ )-alkyl, (C ２ ~C ４ )-alkenyl, (C ２ ~C ４ )-alkynyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-cycloalkyl-(C １ ~C ３ )-alkyl, phenyl-(C １ ~C ３ )-alkyl or furanyl-(C １ ~C ３ )-alkyl (the aliphatic, cycloaliphatic, aromatic or heteroaromatic portion of the last seven groups may contain fluorine, chlorine, bromine, cyano, CO ２ R ａ , C.O.R. ｂ R ｈ , (C １ ~C ２ )-alkoxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ )-substituted with m groups selected from the group consisting of alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R ｅ are independently R ｄ has one of the meanings given for: R ｆ is (C １ ~C ３ )-alkyl or (C １ ~C ３ )-alkoxy; R ｈ is hydrogen, (C １ ~C ６ )-alkyl, (C １ ~C ２ )-alkoxy, (C ３ ~C ６ )-cycloalkyl, (C ２ ~C ４ )-alkenyl, (C ２ ~C ４ )-alkynyl or (C １ ~C ６ )-alkoxycarbonyl-(C １ ~C ６ )-alkyl (the aliphatic or cycloaliphatic portion of the last six groups may contain fluorine, chlorine, bromine, cyano, CO ２ R ａ and (C １ ~C ２ )-alkoxy; each k is independently 0, 1, 2, 3, or 4; each m is independently 0, 1, 2, 3, 4, or 5; each n is independently 0, 1, or 2; each r is independently 1, 2, 3, 4, 5, 6, 7, or 8; and agriculturally acceptable salts, stereoisomers and tautomers thereof.

2. The above substituents have the following meanings: R １ is hydrogen or (C １ ~C ３ )-alkyl; and R ４ is hydrogen or (C １ ~C ３ )-alkyl 2. The compound of claim 1 having the formula:

3. R １ and R ４ The compound of claim 2 wherein is hydrogen.

4. The following conditions a) and b): a) R ２ is (C １ ~C ６ )-alkyl, (C １ ~C ６ )-haloalkyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-alkenyl or (C ３ ~C ６ )-alkynyl; b) R ３ is hydrogen, halogen, (C １ ~C ６ )-alkyl, (C ３ ~C ６ )-cycloalkyl, (C １ ~C ６ )-alkoxy, (C １ ~C ６ )-haloalkoxy, (C ３ ~C ６ )-cycloalkoxy, (C ３ ~C ６ )-alkenyloxy, or (C ３ ~C ６ )-alkynyloxy The compound according to claim 1, wherein the compound satisfies one or both of the following conditions:

5. The following conditions a) and b): a) R ２ is (C １ ~C ６ )-alkyl; b) R ３ is hydrogen or halogen The compound according to claim 4, wherein the compound satisfies one or both of the following conditions:

6. The following conditions a) and b): a) R ２ is methyl or ethyl; preferably methyl; b) R ３ is hydrogen The compound according to claim 5, wherein the compound satisfies one or both of the following conditions:

7. X is a bond; and Y is Z, and Z is preferably CO ２ R ｅ , C.O.R. ｂ R ｈ , S(O) ｎ R ａ , S.O. ２ NR ｂ R ｄ , S.O. ２ NR ｂ COR ｅ , C.O.R. ｂ , C.O.R. ｅ S(O)R ａ , C.O.R. ｅ SO ２ R ａ , C.O.R. ｂ１ SO ２ NR ｂ２ R ｂ３ , N.R. ｂ R ｅ , N.R. ｂ COR ｅ , N.R. ｂ CONR ｅ R ｅ , N.R. ｂ CO ２ R ｅ , N.R. ｂ SO ２ R ｅ , N.R. ｂ１ SO ２ NR ｂ２ R ｅ , OCONR ｂ R ｅ , OCSNR ｂ R ｅ , P.O.R. ｆ R ｆ , C(R ｂ ) = NOR ｅ , Ra, Rc, Re and Rf, and the carbon ring atoms bear n oxo groups; Z is preferably CO ２ R ｅ , C.O.R. ｂ R ｈ , S(O) ｎ R ａ , S.O. ２ NR ｂ R ｄ , S.O. ２ NR ｂ COR ｅ , C.O.R. ｂ , C.O.R. ｅ S(O)R ａ , C.O.R. ｅ SO ２ R ａ , C.O.R. ｂ１ SO ２ NR ｂ２ R ｂ３ , N.R. ｂ R ｅ , N.R. ｂ COR ｅ , N.R. ｂ CONR ｅ R ｅ , N.R. ｂ CO ２ R ｅ , N.R. ｂ SO ２ R ｅ , N.R. ｂ１ SO ２ NR ｂ２ R ｅ , OCONR ｂ R ｅ , OCSNR ｂ R ｅ and P.O.R. ｆ R ｆ , C(R ｂ ) = NOR ｅ m groups selected from the group consisting of: ａ , R ｃ , R ｅ and R ｆ 2. The compound of claim 1, wherein m is substituted with m groups selected from the group consisting of:

8. Z is m groups CO ２ R ｅ is a 5- or 6-membered saturated or partially unsaturated carbocyclic ring substituted with R ｅ is hydrogen or (C １ ~C ６ )-alkyl; Z is preferably m groups CO ２ R ｅ is a 5- or 6-membered partially unsaturated carbocyclic ring substituted with R ｅ is hydrogen or (C １ ~C ６ 8. The compound of claim 7, wherein the aryl group is aryl.

9. Z is one group CO ２ R ｅ is a 5-membered partially unsaturated carbocyclic ring substituted with R ｅ is hydrogen or (C １ ~C ６ )-alkyl, preferably (C １ ~C ４ 9. The compound of claim 8, wherein the aryl group is aryl.

10. X is a divalent unit (X １ ), where R ５ and R ６ are as defined in claim 1 and preferably independently hydrogen or (C １ ~C ６ )-alkyl; and Y is S(O) ｎ R ａ , S.O. ２ NR ｂ R ｄ , S.O. ２ NR ｂ COR ｅ , CO ２ R ｅ , C.O.R. ｂ R ｈ , C.O.R. ｂ , C.O.R. ｅ SO ２ R ａ , N.R. ｂ R ｅ , N.R. ｂ COR ｅ , N.R. ｂ CONR ｅ R ｅ , N.R. ｂ CO ２ R ｅ , N.R. ｂ SO ２ R ｅ , N.R. ｂ SO ２ NR ｂ R ｅ , OCONR ｂ R ｅ , OCSNR ｂ R ｅ , P.O.R. ｆ R ｆ and C(R ｂ ) = NOR ｅ (C １ ~C ８ 2. The compound of claim 1, wherein the aryl group is aryl.

11. Y is m groups CO ２ R ｅ (C １ ~C ４ )-alkyl; R ｅ is hydrogen or (C １ ~C ６ )-alkyl, preferably (C １ ~C ４ 11. The compound of claim 10, wherein the aryl group is aryl.

12. 2. The compound of claim 1, wherein m is 1 or 2, preferably 1.

13. Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein the ring Q is Ｑ１ and n substituents R Ｑ２ where R Ｑ１ is a halogen, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C １ ~C ３ )-alkoxy and (C １ ~C ３ )-haloalkoxy, and ring Q is selected from the group consisting of k substituents R Ｑ１ and n substituents R Ｑ２ where R Ｑ１ is a halogen, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C １ ~C ３ )-alkoxy and (C １ ~C ３ )-haloalkoxy; R Ｑ２ is phenyl-(C １ ~C ３ )-alkyl, (C １ ~C ４ )-alkylcarbonyl, (C １ ~C ４ )-alkylaminocarbonyl, di-(C １ ~C ４ -alkyl)aminocarbonyl, (C １ ~C ４ )-alkoxycarbonyl, benzyloxycarbonyl, fluorenyloxycarbonyl, allyloxycarbonyl, or (C １ ~C ３ )-alkoxy-(C １ ~C ３ )-alkyl, preferably benzyl, acetyl, methylaminocarbonyl, dimethylaminocarbonyl, (C １ ~C ４ 2. The compound of claim 1, wherein k is 0, 1, 2, or 3, and n is 0 or 1.

14. Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein the ring Q is a ring containing k substituents R Ｑ１ and n substituents R Ｑ２ where R Ｑ１ is a halogen, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C １ ~C ３ )-alkoxy and (C １ ~C ３ )-haloalkoxy; R Ｑ２ is (C １ ~C ４ )-alkoxycarbonyl; where k is 0, 1 or 2 and n is 0 or 1.

15. Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein the ring Q is Ｑ１ and n substituents R Ｑ２ where R Ｑ１ is a halogen, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C １ ~C ３ )-alkoxy and (C １ ~C ３ )-haloalkoxy; R Ｑ２ is (C １ ~C ４ )-alkoxycarbonyl; where k is 0, 1, 2 or 3, preferably 0, 1 or 2, and n is 0 or 1; R １ is hydrogen; R ２ But (C １ ~C ６ )-alkyl; R ３ is hydrogen or halogen; R ４ is hydrogen; X is a bond; and Y is Z; where Z is a group selected from m groups CO ２ R ｅ is a 5- or 6-membered saturated or partially unsaturated carbocyclic ring substituted with R ｅ is hydrogen or (C １ ~C ６ )-alkyl and m is 1 or 2; or X is a divalent unit (X １ ) and R ５ and R ６ are each independently hydrogen or (C １ ~C ６ )-alkyl; and Y is m groups CO ２ R ｅ (C １ ~C ４ )-alkyl, where R ｅ is hydrogen or (C １ ~C ６ 2. The compound of claim 1, wherein m is 1 or 2.

16. Q is a 5-membered heteroaromatic ring containing 1 or 2 heteroatoms selected from the group consisting of N, O and S as ring members, or a 6-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as ring members, wherein the ring Q is Ｑ１ and n substituents R Ｑ２ where R Ｑ１ is a halogen, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C １ ~C ３ )-alkoxy and (C １ ~C ３ )-haloalkoxy; R Ｑ２ is (C １ ~C ４ )-alkoxycarbonyl; where k is 0, 1, 2 or 3, preferably 0, 1 or 2, and n is 0 or 1; R １ is hydrogen; R ２ is methyl or ethyl; R ３ is hydrogen; R ４ is hydrogen; X is a bond; and Y is Z; where Z is a group CO ２ R ｅ is a 5-membered partially unsaturated carbocyclic ring substituted by ｅ However, (C １ ~C ６ )-alkyl; or X is a divalent unit (X １ ), where R ５ and R ６ one of which is hydrogen and the other is hydrogen or methyl; and Y is one group CO ２ R ｅ (C １ ~C ４ )-alkyl, where R ｅ However, (C １ ~C ６ 16. The compound of claim 15, wherein the aryl group is aryl.

17. 10. A composition comprising at least one compound according to claim 1 and at least one adjuvant customarily used in the formulation of crop protection compounds.

18. 20. The composition of claim 17, further comprising an herbicide.

19. Use of a compound according to any one of claims 1 to 16 or a composition according to claim 17 or 18 for controlling undesired vegetation.

20. 19. A method for controlling undesirable vegetation, comprising applying a herbicidally effective amount of at least one compound according to any one of claims 1 to 16, or a composition according to claim 17 or 18, to plants, their seeds and / or their habitats.

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