Substituted isophthalic acid diamide

Abstract

The present invention relates to isophthalic acid diamides having the general formula (I) as herbicides. In the formula (I), X, Y and Z represent groups such as hydrogen, alkyl and halogen. Q represents a heterocycle such as tetrazolyl.

Description

[0001] The present invention relates to the technical field of herbicides, in particular to the technical field of herbicides for selectively controlling broadleaf weeds and grass weeds in useful plants.

[0002] WO 2012 / 028579 A1, WO 2012 / 126932 A1, WO 2013 / 017559 A1 and WO 2017 / 144402 A1 describe isophthalimides which are particularly herbicidally active and differ fundamentally in the nature of the substituents on the two amide functions.

[0003] The isophthalimides specifically disclosed therein always have a tertiary amide group. However, the isophthalimides known from these documents do not always have sufficient herbicidal efficacy and / or compatibility with crop plants. It has been found that isophthalimides having primary or secondary amide groups have superior properties compared to the isophthalimides known from the prior art.

[0004] Therefore, the present invention provides an isophthalimide of formula (I) or a salt thereof

[0005]

[0006] The symbols and subscripts are defined as follows:

[0007] Q for Q 1 , Q 2 , Q 3 or Q 4

[0008]

[0009] R 1 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl,

[0010] R 2 is (C1-C6)-alkyl,

[0011] R x is (C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or phenyl,

[0012] R y is halogen, (C1-C6)-alkyl or halo-(C1-C6)-alkyl,

[0013] R z is hydrogen, (C1-C6)-alkyl or halo-(C1-C6)-alkyl,

[0014] X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R 1 O.R 2 (O) n S or R 1 O-(C1-C6)-alkyl or R 2 S(O) n -(C1-C6)-alkyl,

[0015] Y is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 1 O or R 2 (O) n S,

[0016] Z is hydrogen,

[0017] One of the following groups, each of which is selected from halogen, cyano, R 1 C(O), R 1 OC(O),R 1 O and R 2 (O) n S is substituted by a group: (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyl-(C1-C6)-alkyl, (C2-C6)-alkynyl, (C2-C6)-alkynyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, R 2 S(O) n -(C1-C6)-alkyl, R 1 C(O), R 1 OC(O),R 1 C(O)-(C1-C6)-alkyl, R 1 OC(O)-(C1-C6)-alkyl, R 1 NH-(C1-C6)-alkyl, R 1 2N-(C1-C6)-alkyl, R 1 NHC(O)-(C1-C6)-alkyl or R 1 2NC(O)-(C1-C6)-alkyl, or

[0018] One of the following groups, each of which is selected from halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, R 1 C(O) and R 1The radical substitution of OC(O) is: phenyl, benzyl, phenyl, benzyl, heterocyclyl or heterocyclyl-(C1-C6)-alkyl,

[0019] n is 0, 1, or 2,

[0020] s is 0, 1, 2, or 3

[0021] In formula (I) and all the following formulas, the alkyl group with more than two carbon atoms can be straight or branched. The alkyl group is, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, allyl, 1-methylprop-2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methylbut-3-yn-1-yl. Multiple bonds can be located at any position in each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system with three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Alkyl substituted with halogen means a straight or branched alkyl group, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms, for example C1-C2-haloalkyl, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

[0022] Halogen represents fluorine, chlorine, bromine or iodine.

[0023] A heterocyclic group (heterocyclyl) is a 5- or 6-membered cyclic group which, in addition to carbon atoms, contains at least one heteroatom selected from N, O, S and which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, in which case the point of bond is at a ring atom. Examples of heterocyclic groups are 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-1- or 2- or 3- or 4 -yl; 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or -4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3 ,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2- or 3-tetrahydrophenylthio; 2,3-dihydrophenylthio-2- or 3- or 4- or 5-yl; 2,5-dihydrophenylthio-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran -2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl; 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl;Hexahydropyridazine-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3- or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3- or 4-yl; 1,6-dihydropyriazin-1- or 3- or 4- or 5- or 6-yl; Hexahydropyrimidine-1- or 2- or 3- or 4-yl; 1,4,5,6 -tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazine- 1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazine-1- or 2- or 3-yl; 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazine-2- or 3-yl; 1,3-dioxol-2- or 4- or 5-yl; 1,3-dioxan-2- or 4- or 5-yl; 4H-1,3-dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxin-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxol hexen-2-, 3-, 5-, or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiolan-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiolan-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithiol-2- or 4- or 5-yl;4H-1,3-dithien-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3-oxazolin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro- 2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2 H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazine-3- or 4- or 5- or 6-yl; 4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 6H -1,3-oxazine-2- or 4- or 5- or 6-yl; 4H-1,3-oxazine-2- or 4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 2H- 1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2- or 3-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl;1,3-thiazinane (thiazinan)-2-or 3-or 4-or 5-or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2-or 3-or 4-or 5-or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2-or 3-or 4-or 5-or 6-yl; 5,6-dihydro-2H-1,3-thiazin-2-or 4-or 5-or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2-or 4-or 5-or 6-yl; 2H-1,3-thiazin- oxazine-2- or 4- or 5- or 6-yl; 6H-1,3-thiazine-2- or 4- or 5- or 6-yl; 4H-1,3-thiazine-2- or 4- or 5- or 6-yl; 4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazine-3- or 5- or 6-yl; 1,4,2-dioxazine-3- or 5- or 6-yl. ;

[0024] Depending on the nature of the substituents and their mode of attachment, the compounds of general formula (I) may exist as stereoisomers. For example, if there are one or more asymmetrically substituted carbon atoms, enantiomers and diastereomers may exist. When n is 1 (sulfoxide), stereoisomers may also occur. Stereoisomers can be obtained from the mixture obtained during the preparation process by conventional separation methods, for example by chromatographic separation methods. Stereoisomers can also be selectively prepared by using stereoselective reactions and using optically active starting materials and / or auxiliary agents. The present invention also relates to all stereoisomers and mixtures thereof covered but not explicitly defined by (I).

[0025] The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example, having the formula [NRR′R″R″′] + A salt of a cation wherein R to R"' are each independently an organic group, in particular an alkyl, aryl, aralkyl or alkylaryl group. Also useful are alkylsulfonium salts and alkylsulfoxonium salts, for example (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkylsulfoxonium salts.

[0026] The compounds of formula (I) can be formed into salts by the adduct formation reaction of a suitable inorganic or organic acid (e.g. mineral acid, e.g. HCl, HBr, H2SO4, H3PO4 or HNO3, or an organic acid, e.g. a carboxylic acid such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or a sulfonic acid such as p-toluenesulfonic acid) with a basic group (e.g. amino, alkylamino, dialkylamino, piperidinyl, morpholino or pyrido). These salts then contain the conjugate base of the acid as an anion.

[0027] Preference is given to compounds of the general formula (I) in which the symbols and indices have the following meanings:

[0028] Q for Q 1 , Q 2 , Q 3 or Q 4

[0029]

[0030] R x is Me, Et, Pr, i-Pr, c-Pr, (CH2)2OMe or Ph,

[0031] R y is Cl, Me, Et or CF3,

[0032] R z is hydrogen, Me, Et or CF3,

[0033] X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, c-Pr, OMe, OEt, SMe, SEt, SO2Me, SO2Et, CH2OMe, CH2SMe, CH2SO2Me, (CH2)2SMe or (CH2)2SO2Me,

[0034] Y is halogen, halo-(C1-C6)-alkyl, OMe, SMe, S(O)Me, SO2Me, SEt, S(O)Et or SO2Et,

[0035] Z is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2c-Pr, halo-(C1-C6)-alkyl, (CH2)2OMe, (CH2)2OEt, allyl, propynyl, (CH2)2SMe, (CH2)2SO2Me, C(O)Me, C(O)cPr, C(O)OMe, C(O)OEt, CH2-(tetrahydrofuran-2-yl), oxetan-3-yl, CH2C(O)Me, CH2C(O)c-Pr, CH2C(O)NMe2, CH2CN, Ph, CH2Ph ​​or CH2-(thiophen-2-yl), OMe, OEt, OPr, Oi-Pr.

[0036] Particular preference is given to compounds of the general formula (I), in which the symbols and indices have the following meanings:

[0037] Q is Q1 or Q4,

[0038] R x is Me, Et or Pr,

[0039] R z is H or Me,

[0040] X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt, CH2OMe or CF3,

[0041] Y is F, Cl, Br, I, SMe, S(O)Me, SO2Me, CF3, CHF2 or C2F5,

[0042] Z is hydrogen, Me, Et, c-Pr, Pr, i-Pr, c-Bu, CH2-c-Pr, CH2CHF2, CH2CF3, CH(Me)-c-Pr, (CH2)2OMe, (CH2)2SMe, CH2CN, CH2-(tetrahydrofuran-2-yl), CH2C(O)NMe2, Ph or CH2-(thiophen-2-yl), oxetan-3-yl, OMe, OEt, OPr, Oi-Pr.

[0043] The compounds of the present invention can be prepared, for example, by the method described in detail in Scheme 1 of WO 2012 / 028579 A1. The corresponding benzoyl chlorides or their parent benzoic acids are known in principle and can be prepared, for example, by the methods described in WO1997 / 041105, WO1998 / 029383, WO1999 / 021852, EP282944, JP11021280, JP11012275 or CN103130730. The working examples described further below further illustrate the preparation of the compounds of the present invention.

[0044] Work-up of the respective reaction mixture is generally effected by known methods, for example by crystallization, aqueous-extractive workup, by chromatography or by a combination of these methods.

[0045] Depending on the nature of the substituents and their mode of attachment, the compounds of general formula (I) may exist as stereoisomers. For example, if there are one or more asymmetrically substituted carbon atoms, enantiomers and diastereomers may exist. When n is 1 (sulfoxide), stereoisomers may also occur. Stereoisomers can be obtained from the mixture obtained during the preparation process by conventional separation methods, for example by chromatographic separation methods. Stereoisomers can also be selectively prepared by using stereoselective reactions and using optically active starting materials and / or auxiliaries. The present invention also relates to all stereoisomers and mixtures thereof that are encompassed but not clearly defined by general formula (I).

[0046] The compound of formula (I) and / or its salt collection that can be synthesized by the above-mentioned reaction can also be prepared in a parallel manner, in which case this can be done manually, partially automatically or fully automatically. For example, the reaction, post-treatment or purification of product and / or intermediate can be automated. In general, this is understood to mean the operation described in, for example, D. Tiebes in Combinatorial Chemistry-Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999, pages 1 to 34.

[0047] The compounds of formula (I) (and / or their salts) of the present invention, hereinafter collectively referred to as "compounds of the present invention", have excellent herbicidal efficacy against a wide spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants.

[0048] Therefore, the present invention also provides a method for controlling unwanted plants or for regulating plant growth, preferably in plant crops, wherein one or more compounds of the present invention are applied to plants (e.g., harmful plants, such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g., grains, seeds or vegetative propagation bodies, such as tubers or shoot parts with buds) or areas where plants grow thereon (e.g., cultivated areas). The compounds of the present invention can be used, for example, before sowing (if appropriate, also by incorporation into the soil), before emergence or after emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are as follows, but this enumeration is not intended to impose a restriction on specific species.

[0049] Monocotyledonous harmful plants of the following genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrosti s), Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0050] Dicotyledonous weeds of the following genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Thistle Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindern ia), Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0051] When the compounds of the present invention are applied to the soil surface before emergence, emergence of weed seedlings is completely prevented, or the weeds grow until they have reached the cotyledon stage but then cease to grow.

[0052] If the active ingredients are applied to the green parts of the plants after emergence, growth stops after the treatment and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, thus eliminating competition from weeds that are harmful to the crop plants very early and in a permanent manner.

[0053] The compounds according to the invention can be selective in crops of useful plants and can also be used as non-selective herbicides.

[0054] By virtue of its weeding and plant growth regulating properties, the active ingredients can also be used to control harmful plants in known or undeveloped genetically modified plant crops. Typically, transgenic plants are characterized by particularly favorable properties, such as resistance to certain active ingredients (particularly certain herbicides) used in the agrochemical industry, resistance to plant diseases or pathogens of plant diseases (e.g., certain insects or microorganisms such as fungi, bacteria or viruses). Other specific features relate to, for example, the quantity, quality, storage, composition and specific ingredients of the harvested material. For example, there are known transgenic plants with increased starch content or altered starch quality, or those transgenic plants with different fatty acid compositions in the harvested material. Other specific properties are tolerance or resistance to abiotic stress factors (e.g., heat, cold, drought, salinity and ultraviolet radiation).

[0055] The compounds of the formula (I) or salts thereof according to the invention are preferably used in transgenic crops of economically important useful plants and ornamental plants.

[0056] The compounds of the formula (I) can be employed as herbicides in crops of useful plants which are resistant to the phytotoxic effects of herbicides or have been rendered resistant to the phytotoxic effects of herbicides by genetic engineering.

[0057] Conventional methods for producing novel plants which have modified properties compared to existing plants consist essentially, for example, in conventional cultivation methods and the generation of mutants.

[0058] Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP 0221044, EP 0131624). Described are, for example, several cases of genetic modification of crop plants in order to improve the starch synthesis in the plants (e.g. WO 92 / 011376 A, WO 92 / 014827 A, WO 91 / 019806 A), transgenic crop plants which are resistant to certain herbicides of the glufosinate class (see, for example, EP 0242236 A, EP 0242246 A), the glyphosate class (WO 92 / 000377 A), the sulfonylurea class (EP 0257993 A, US 5,013,659) or combinations or mixtures of these herbicides by "gene stacking", for example transgenic crop plants such as corn or soybeans which have the trade name or designation Optimum™ GAT™ (glyphosate ALS tolerant).

[0059] - transgenic crop plants, such as cotton, which produce Bacillus thuringiensis toxins (Bt toxins) which render the plants resistant to specific pests (EP 0142924 A, EP 0193259 A),

[0060] - transgenic crop plants with improved fatty acid composition (WO 91 / 013972 A),

[0061] - genetically modified crop plants with new components or secondary metabolites, such as new phytoalexins, which confer enhanced disease resistance (EP 0309862 A, EP 0464461 A),

[0062] - genetically modified plants with reduced photorespiration, which have higher yield and higher stress tolerance (EP0305398 A),

[0063] - transgenic crop plants producing pharmaceutically or diagnostically important proteins ("molecular pharming"),

[0064] - genetically modified crop plants characterized by higher yield or better quality,

[0065] - Transgenic crop plants characterized by, for example, a combination of the above-mentioned novel properties ("gene stacking").

[0066] In principle, a large number of molecular biology techniques are known for producing novel transgenic plants with improved properties; see, for example, I. Potrykus and G. Spangenberg (eds), Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, "Trends in Plant Science" 1 (1996) 423-431).

[0067] For such genetic manipulation, a nucleic acid molecule that allows mutation or sequence changes by recombinant DNA sequences can be introduced into a plasmid. With the aid of standard methods, for example, base exchanges, removal of partial sequences, or addition of natural or synthetic sequences can be performed. In order to connect DNA fragments to each other, adapters or linkers can be added to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

[0068] For example, the production of plant cells with reduced gene product activity can be achieved by the following methods: by expressing at least one corresponding antisense RNA, a sense RNA for achieving co-suppression, or by expressing at least one appropriately constructed ribozyme that specifically cuts the transcript of the above-mentioned gene product. To this end, firstly, DNA molecules that cover the entire coding sequence of the gene product (including any flanking sequences that may be present) can be used, as well as DNA molecules that only cover part of the coding sequence, in which case these parts must be long enough to produce an antisense effect in the cell. DNA sequences that have a high degree of homology to the coding sequence of the gene product but are not completely identical thereto can also be used.

[0069] When expressing nucleic acid molecules in plants, the synthesized protein can be positioned in any desired compartment of the plant cell. However, in order to achieve positioning in a specific compartment, the coding region can be connected to a DNA sequence that ensures positioning in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in organelles of plant cells.

[0070] Transgenic plant cells can be regenerated by known techniques to grow into complete plants. In principle, the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledons but also dicotyledons. Transgenic plants can be obtained in this way, the properties of which are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

[0071] The compounds (I) of the present invention can be preferably used in transgenic crops resistant to the following substances: growth regulators, such as 2,4-D, dicamba; or herbicides that inhibit important plant enzymes (such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD)); or herbicides selected from sulfonylureas, glyphosate, glufosinate or benzoyl isoxazole and similar active ingredients; or any desired combination of these active ingredients.

[0072] The compounds of the present invention can be particularly preferably used for transgenic crop plants resistant to the combination of glyphosate and glufosinate, glyphosate and sulfonylurea or imidazolinone. Most preferably, the compounds of the present invention can be used for transgenic crop plants such as corn or soybeans, for example, under the trade name or the name OptimumTM GATTM (glyphosate ALS tolerance).

[0073] When the active ingredients of the present invention are used in transgenic crops, not only the effects on harmful plants observed in other crops will appear, but also effects specific to the application in a particular transgenic crop will often appear, for example, an altered or particularly broadened spectrum of weeds that can be controlled, an altered application rate that can be used for application, preferably good compatibility with herbicides to which the transgenic crops are resistant, and an effect on the growth and yield of the transgenic crop plants.

[0074] The present invention therefore also relates to the use of the compounds of the formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0075] The compounds of the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in conventional formulations. Therefore, the present invention also provides herbicidal compositions and plant growth regulating compositions containing the compounds of the invention.

[0076] The compounds of the invention can be formulated in various ways according to the desired biological and / or physicochemical parameters. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as water emulsions and oil emulsions, sprayable solutions, suspensions (SC), oil- or water-based dispersions, oil-miscible solutions, microcapsule suspensions (CS), dusting products (DP), dressings, granules for broadcasting and soil application, granules in microgranular form (GR), spray granules, absorption granules and adsorption granules, water-dispersible granules (WG), soluble granules (SG), ULV preparations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th edition, 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973, K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. London.

[0077] Necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books, Caldwell NJ, HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd edition, Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MCPubl. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, [Interface-active EthyleneOxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", volume 7, C. Hanser Verlag Munich, 4th edition, 1986.

[0078] Based on these formulations, combinations with other active ingredients (for example insecticides, acaricides, herbicides, fungicides) and with safeners, fertilizers and / or growth regulators can also be prepared, for example in the form of ready formulations or tank mixes.

[0079] Combination partners that can be used for the compounds of the invention in mixed formulations or tank mixes are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as known, for example, from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein. Known herbicides or plant growth regulators that can be combined with the compounds of the invention are, for example, the following substances, where the active ingredients are indicated by "common names" according to the International Organization for Standardization (ISO) or by their chemical names or code numbers. They always encompass all use forms, such as acids, salts, esters and all isomeric forms such as stereoisomers and optical isomers, even if they are not explicitly mentioned.

[0080] Examples of such herbicidal combinations include:

[0081] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate sulfamate), anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bispyribac, benzophenone, benzophenone-methyl, benzophenone-oxazolidinone, benzophenone-oxazolidinone, benzophenone-methyl ... fenox), bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate, busoxinone, butachlor, butafenacil,butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenp rop), chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, 3-[5-chloro-4-(trifluoromethyl)piperidin-2-yl]-4-hydroxy-1-methylimidazolin-2-one, cinidon ), cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide anamide), cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropylammonium, 2,4-D-potassium, 2,4-D-triisopropanolammonium and 2,4-D-triethanolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmediphthol am), detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat , diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, diinitramine, dinoterb, diphenamid 、diquat、diquat-dibromid、dithiopyr、diuron、DNOC、endothal、EPTC、esprocarb、ethalfluralin、ethametsulfuron、ethametsulfuron-methyl、ethiozin、ethofumesate、ethoxyfen、ethoxyfen-ethyl、Ethoxysulfuron, etobenzanid, F-9600, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluaz ifop), fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flufenoxal flumiclorac), flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium and flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron,Flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fo samine), glufosinate, glufosinate-ammonium, glufosinate-sodium, glufosinate-ammonium, glufosinate-sodium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium, H-9201 (O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylphosphoramidothioate), halaux ifen), halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethyl ethoxylate, haloxyfop-ethyl ethoxylate, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e. (2,4-dichlorophenoxy)acetic acid 1-(dimethoxy) 4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin, imazapyr, imazethapyr,imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, iodosulfuron potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxadiazine xaben), isoxaflutole, karbutilate, KUH-043 (i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butoxyethyl ester, MCPA-dimethylammonium, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium, MCPA-potassium and MCPA-sodium, MCPB, MC PB-methyl ester, MCPB-ethyl ester and MCPB-sodium, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid sodium and 2-methyl-4-chloropropionic acid butoxyethyl ester, 2-methyl-4-chloropropionic acid (mecoprop-P), 2-methyl-4-chloropropionic acid butoxyethyl ester, 2-methyl-4-chloropropionic acid dimethylammonium ester, 2-methyl-4-chloropropionic acid-2-ethylhexyl ester and 2-methyl-4-chloropropionic acid potassium ester, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione ione), methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methylisothiocyanate, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), neburon, nicosulfuron, pelargonic acid acid), norflurazon, oleic acid, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione, lancotrione, oxyfluorfen, paraquat, paraquatdichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils), phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham,propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolynate yrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-ethyl ofop-P-ethyl), quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523,SYP-249 (i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, pyranose tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl ), thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron floxysulfuron), trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), and the following compounds:,

[0082]

[0083] Examples of plant growth regulators as possible admixtures are:

[0084] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, fiurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid acid), inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, methyl jasmonate, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture mixture), 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, and uniconazole-P.

[0085] The safeners which can be used in combination with the compounds of formula (I) according to the present invention and optionally in combination with other active ingredients (such as the insecticides, acaricides, herbicides, fungicides listed above) are preferably selected from:

[0086] S1) A compound of formula (S1),

[0087]

[0088] The symbols and superscripts have the following meanings:

[0089] n A is a natural number from 0 to 5, preferably from 0 to 3;

[0090] R A 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl;

[0091] W A is an unsubstituted or substituted divalent heterocyclic group selected from partially unsaturated or aromatic five-membered heterocyclic rings having 1 to 3 ring heteroatoms selected from N and O, wherein at least one nitrogen atom and at most one oxygen atom are present in the ring, preferably selected from (W A 1 ) to (W A 4 ),

[0092]

[0093] m A is 0 or 1;

[0094] R A 2 OR A 3 , SR A 3 or NR A 3 R A 4 , or a saturated or unsaturated 3- to 7-membered heterocyclic ring having at least one nitrogen atom and up to 3 heteroatoms (preferably selected from O and S), which is linked to the carbonyl group in (S1) via the nitrogen atom and is unsubstituted or substituted by (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR A 3 、NHR A 4 or N(CH3)2, especially a group of formula OR A 3;

[0095] R A 3 is hydrogen, or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0096] R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl;

[0097] R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 , where R A 9 is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C 12 )-cycloalkyl or tri-(C1-C4)-alkylsilyl;

[0098] R A 6 , R A 7 , R A 8 are identical or different and are hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or substituted or unsubstituted phenyl;

[0099] Preferably:

[0100] a) dichlorophenylpyrazoline-3-carboxylic acid type compound (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874;

[0101] b) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4), and related compounds as described in EP-A-333131 and EP-A-269806;

[0102] c) 1,5-diphenylpyrazole-3-carboxylic acid derivatives (S1 c ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6), and related compounds as described in, for example, EP-A-268554;

[0103] d) Triazole carboxylic acid type compounds (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0104] e) a compound of the type 5-benzyl-2-isoxazoline-3-carboxylic acid, 5-phenyl-2-isoxazoline-3-carboxylic acid, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9), and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897.

[0105] S2) Quinoline derivatives of formula (S2)

[0106]

[0107] The symbols and superscripts have the following meanings:

[0108] R B 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl;

[0109] n B is a natural number from 0 to 5, preferably from 0 to 3;

[0110] R B 2 OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocyclic ring having at least one nitrogen atom and up to 3 heteroatoms (preferably selected from O and S), which in (S2) is linked to the carbonyl group via the nitrogen atom and which is unsubstituted or substituted by a radical selected from (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR B 3 、NHR B 4 or N(CH3)2, especially a group of formula OR B 3 ;

[0111] R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0112] R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl;

[0113] T B is a (C1 or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4)-alkyl groups or by [(C1-C3)-alkoxy]carbonyl groups;

[0114] Preferably:

[0115] a) 8-quinolinyloxyacetic acid type compounds (S2 a), preferably (5-chloro-8-quinolinyloxy)acetic acid 1-methylhexyl ester ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutan-1-yl ester (S2-2), (5-chloro-8-quinolinyloxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-chloro-8-quinolinyloxy)acetic acid 1-allyloxypropan-2-yl ester (S2-4), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolyloxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolyloxy)acetic acid allyl ester (S2-7), (5-chloro-8-quinolyloxy)acetic acid 2-(2-propylene iminooxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolyloxy)acetic acid 2-oxopropan-1-yl ester (S2-9), and EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 Related compounds described in 492 366, and (5-chloro-8-quinolinyloxy)acetic acid (S2-10), hydrates and salts thereof, such as lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002 / 34048;

[0116] b) (5-chloro-8-quinolinyloxy)malonic acid type compound (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolyloxy)malonate, diallyl (5-chloro-8-quinolyloxy)malonate, methyl ethyl (5-chloro-8-quinolyloxy)malonate, and related compounds as described in EP-A-0 582 198.

[0117] S3) Compound of formula (S3)

[0118]

[0119] The symbols and subscripts are defined as follows:

[0120] R C 1 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;

[0121] R C 2 , R C 3are the same or different and are hydrogen, (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, (C1-C4) haloalkyl, (C2-C4) haloalkenyl, (C1-C4) alkylcarbamoyl-(C1-C4) alkyl, (C2-C4) alkenylcarbamoyl-(C1-C4) alkyl, (C1-C4) alkoxy-(C1-C4) alkyl, dioxolyl-(C1-C4) alkyl, thiazolyl, furanyl, furanylalkyl, thienyl, piperidinyl, substituted or unsubstituted phenyl, or R C 2 and R C 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;

[0122] Preferably:

[0123] Active ingredients of the dichloroacetamide type, which are often used as pre-emergence safeners (safeners acting on the soil), e.g.

[0124] "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1),

[0125] "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2) from Stauffer,

[0126] "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3) from Stauffer,

[0127] "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),

[0128] "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5) from PPG Industries,

[0129] "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6) from Sagro-Chem,

[0130] "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7) from Nitrokemia or Monsanto,

[0131] "TI-35" (1-dichloroacetylazepane) (S3-8) from TRI-Chemical RT,

[0132] "diclonon" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF,

[0133] "Furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11).

[0134] S4) N-acylsulfonamide of formula (S4) and its salt,

[0135]

[0136] The symbols and subscripts are defined as follows:

[0137] A D SO2-NR D 3 -CO or CO-NR D 3 -SO2

[0138] X D is CH or N;

[0139] R D 1 For CO-NR D 5 R D 6 or NHCO-R D 7 ;

[0140] R D 2 is halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;

[0141] R D 3 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl;

[0142] R D4 is halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;

[0143] R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or contains v D 3- to 6-membered heterocyclic radicals having 3 to 6 heteroatoms selected from nitrogen, oxygen and sulfur, wherein the last seven radicals are replaced by v D substituted by halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl and phenyl and, in the case of cyclic groups, also (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0144] R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, wherein the last three radicals are replaced by v D substituted by a group selected from halogen, hydroxy, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio, or

[0145] R D 5 and R D 6 Together with the nitrogen atom that carries them, they form a pyrrolidinyl or piperidinyl group;

[0146] R D 7 is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, wherein the last two radicals are replaced by v D substituted by a substituent selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic groups, also (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0147] nD is 0, 1, or 2;

[0148] m D is 1 or 2;

[0149] v D is 0, 1, 2, or 3;

[0150] Among them, N-acylsulfonamide type compounds are preferred, such as the following formula (S4 a ) of the N-acylsulfonamide type, which are known, for example, from WO-A-97 / 45016

[0151]

[0152] in

[0153] R D 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, wherein the last two groups are v D substituted by a substituent selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic groups, also (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0154] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0155] m D is 1 or 2;

[0156] v D is 0, 1, 2, or 3;

[0157] and compounds of acylaminosulfonylbenzamide, such as the following formula (S4 b ) of the acylaminosulfonylbenzamides known, for example, from WO-A-99 / 16744,

[0158]

[0159] For example, compounds in which

[0160] R D 5 = cyclopropyl and (R D 4 )=2-OMe("cyprosulfamide", S4-1),

[0161] R D5 = cyclopropyl and (R D 4 )=5-Cl-2-OMe(S4-2),

[0162] R D 5 = ethyl and (R D 4 )=2-OMe(S4-3),

[0163] R D 5 = isopropyl and (R D 4 )=5-Cl-2-OMe(S4-4) and

[0164] R D 5 = isopropyl and (R D 4 )=2-OMe(S4-5)

[0165] as well as

[0166] Formula (S4 c ) of the N-acylsulfamoylphenylurea type, which are known, for example, from EP-A-365484,

[0167]

[0168] in

[0169] R D 8 and R D 9 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,

[0170] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3,

[0171] m D is 1 or 2;

[0172] For example

[0173] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea ("metcamifen", S4-6),

[0174] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0175] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

[0176] as well as

[0177] Formula (S4 d ), which is known, for example, from CN 101838227,

[0178]

[0179] For example, compounds in which

[0180] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0181] m D is 1 or 2;

[0182] R D 5 It is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl.

[0183] S5) Active ingredients from the class of hydroxyaromatic compounds and aromatic aliphatic carboxylic acid derivatives (S5), for example

[0184] Ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, and WO-A-2005 / 016001.

[0185] S6) Active ingredients (S6) from the class of 1,2-dihydroquinoxaline-2-ones, for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, as described in WO-A-2005 / 112630.

[0186] S7) A compound of formula (S7), as described in WO-A-1998 / 38856,

[0187]

[0188] The symbols and subscripts are defined as follows:

[0189] R E 1 , R E 2 are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro;

[0190] A E For COOR E 3 or COSR E 4

[0191] R E 3 , R E 4 are independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridylalkyl and alkylammonium,

[0192] n E 1 0 or 1

[0193] n E 2 、n E 3 are independently 0, 1 or 2,

[0194] Preferably:

[0195] Diphenylmethoxyacetic acid,

[0196] Ethyl diphenylmethoxyacetate,

[0197] Methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

[0198] S8) A compound of formula (S8), as described in WO-A-98 / 27049,

[0199]

[0200] in

[0201] X F is CH or N,

[0202] n F In X F=N is an integer from 0 to 4,

[0203] In X F =CH is an integer from 0 to 5,

[0204] R F 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy,

[0205] R F 2 is hydrogen or (C1-C4)-alkyl,

[0206] R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different, groups selected from halogen and alkoxy; or a salt thereof,

[0207] Preferred compounds include

[0208] X F For CH,

[0209] n F is an integer from 0 to 2,

[0210] R F 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy,

[0211] R F 2 is hydrogen or (C1-C4)-alkyl,

[0212] R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different groups selected from halogen and alkoxy,

[0213] or a salt thereof.

[0214] S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example

[0215] 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.

[0216] S10 a ) or (S10 b )

[0217] As described in WO-A-2007 / 023719 and WO-A-2007 / 023764

[0218]

[0219] in

[0220] R G 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,

[0221] Y G , Z G Independently of each other, they represent O or S,

[0222] n G is an integer from 0 to 4,

[0223] R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halogenated benzyl,

[0224] R G 3 is hydrogen or (C1-C6)-alkyl.

[0225] S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressings, for example

[0226] "oxabetrinil" ((Z)-1,3-dioxol-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed dressing safener for millet / sorghum against metolachlor damage,

[0227] "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxol-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against metolachlor damage, and

[0228] "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum against metolachlor damage.

[0229] S12) Active ingredients from the class of isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.

[0230] S13) One or more compounds from group (S13):

[0231] "Naphthalic anhydride" (1,8-naphthalene dicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against damage by thiocarbamate herbicides,

[0232] "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,

[0233] "flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet / sorghum against damage by alachlor and isopropylamine,

[0234] "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American cyanamid, which is known as a safener for corn against damage by imidazolinones,

[0235] "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known to be used as a safener for corn,

[0236] "MG 838" from Nitrokemia (CAS Reg. No. 133993-74-5) (2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6),

[0237] "disulfoton" (S-2-ethylthioethyl dithiophosphoric acid O,O-diethyl ester) (S13-7),

[0238] "Dietholate" (O-phenylthiophosphorothioate O,O-diethyl ester) (S13-8),

[0239] "mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

[0240] S14) Active ingredients which, in addition to their herbicidal action against harmful plants, also act as safeners for crop plants such as rice, e.g.

[0241] "dimepiperate" or "MY-93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide graminis,

[0242] "daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron,

[0243] "cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage by some herbicides,

[0244] "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,

[0245] "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4) from Kumiai, which is known as a safener for use in rice against damage by some herbicides.

[0246] S15) A compound of formula (S15) or a tautomer thereof

[0247]

[0248] As described in WO-A-2007 / 131861 and WO-A-2008 / 131860

[0249] in,

[0250] R H 1 is a (C1-C6)-haloalkyl group, and

[0251] R H 2 is hydrogen or a halogen, and

[0252] R H 3 , R H 4 are independently hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl,

[0253] wherein the last three radicals are each unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl,

[0254] or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused at one side of the ring to form a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl fused at one side of the ring to form a 4- to 6-membered saturated or unsaturated carbocyclic ring,

[0255] wherein the last four radicals are each unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl,

[0256] or

[0257] R H3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy, and

[0258] R H 4 is hydrogen or (C1-C4)-alkyl, or

[0259] R H 3 and R H 4 Together with the directly attached nitrogen atom, represents a four- to eight-membered heterocycle which, in addition to the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms selected from N, O and S, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0260] S16) Active compounds which are primarily used as herbicides but have a safener effect on crop plants, e.g.

[0261] (2,4-dichlorophenoxy)acetic acid (2,4-D),

[0262] (4-Chlorophenoxy)acetic acid,

[0263] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

[0264] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

[0265] (4-chloro-o-tolyloxy)acetic acid (MCPA),

[0266] 4-(4-chloro-o-tolyloxy)butyric acid,

[0267] 4-(4-chlorophenoxy)butyric acid,

[0268] 3,6-Dichloro-2-methoxybenzoic acid (dicamba),

[0269] 1-(Ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

[0270] Particularly preferred safeners are mefenpyr-butyl, cyproconazole, isoxadiazine, cloquintocet-mexyl, benoxacor, mefenacet and metcamifen.

[0271] Wettable powders are preparations which can be dispersed uniformly in water and which contain, in addition to the active ingredient, surfactants (wetting agents, dispersants) of the ionic and / or nonionic type, in addition to diluents or inert substances, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare such wettable powders, the active herbicidal ingredient is finely ground, for example, in conventional apparatus such as hammer mills, blower mills and jet mills, and simultaneously or subsequently mixed with formulation adjuvants.

[0272] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or relatively high-boiling aromatic compounds or hydrocarbons) or a mixture of organic solvents and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0273] Dusting products are obtained by grinding the active ingredient with finely divided solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0274] Suspensions can be water-based or oil-based. They can be prepared, for example, by wet grinding with the aid of a commercially available bead mill and optionally with the addition of surfactants such as have been listed above for the other formulation types.

[0275] Emulsions, such as emulsions in water (EW), can be prepared, for example, using aqueous organic solvents and optionally surfactants as have been listed above, for example, for the other formulation types, with the aid of stirrers, colloid mills and / or static mixers.

[0276] Granules can be prepared by spraying the active ingredient onto a granular inert material capable of absorption or by applying the active ingredient concentrate to the surface of a carrier material (e.g. sand, kaolinite or granular inert material) with the aid of a binder (e.g. polyvinyl alcohol, sodium polyacrylate or mineral oil). Suitable active compounds can also be granulated in a manner customary for the preparation of fertilizer granules, if desired mixed with fertilizers.

[0277] Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized bed granulation, pan granulation with mixing with a high-speed mixer and extrusion without solid inert material.

[0278] For the preparation of pan granules, fluidized bed granules, extruded granules and spray granules, see, for example, the methods in "Spray Drying Handbook", 3rd edition, 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq.; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw Hill, New York 1973, pages 8-57.

[0279] For further detailed information on the formulation of crop protection compositions, see, for example, GC Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, “Weed Control Handbook”, 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0280] Agrochemical formulations generally contain 0.1% to 99% by weight, especially 0.1% to 95% by weight of the compound of the present invention. In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, and the remainder to 100% by weight is composed of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active ingredient may be about 1% to 90% by weight and preferably 5% to 80% by weight. Formulations in the form of powders contain 1% to 30% by weight of active ingredients, preferably usually 5% to 20% by weight of active ingredients; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredients. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active ingredient is in liquid or solid form, as well as the granulation aids, fillers, etc. used. In water-dispersible granules, the content of the active ingredient is, for example, 1 to 95% by weight, preferably 10 to 80% by weight.

[0281] Furthermore, the active ingredient preparations mentioned optionally contain various customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, antifoams, evaporation inhibitors and agents for influencing pH and viscosity.

[0282] Based on these formulations, it is also possible to prepare combinations with other pesticide active substances (eg insecticides, acaricides, herbicides, fungicides), and also with safeners, fertilizers and / or growth regulators, for example in the form of ready formulations or tank mixes.

[0283] For application, commercially available formulations are diluted, if appropriate, in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersible concentrates and water-dispersible granules. Formulations in the form of dusts, granules for soil application or granules for broadcasting and sprayable solutions are usually not further diluted with other inert substances before application.

[0284] The required application rate of the compound of formula (I) and its salt varies according to external conditions (e.g., especially temperature, humidity and the type of herbicide used). It can vary over a wide range, for example, from 0.001 to 10.0 kg / ha or more of active substance, but it is preferably from 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, more preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence applications and to post-emergence applications.

[0285] A carrier is a natural or synthetic, organic or inorganic substance with which the active ingredient is mixed or combined for better applicability, especially for application to plants or plant parts or seeds. The carrier can be solid or liquid, is generally inert, and should be suitable for use in agriculture.

[0286] Useful solid or liquid carriers include, for example, ammonium salts; and natural rock powders, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth; and synthetic rock powders, such as finely divided silicon dioxide, aluminum oxide and natural or synthetic silicates; resins; waxes; solid fertilizers; water; alcohols, especially butanol; organic solvents; mineral oils; vegetable oils; and derivatives thereof. Mixtures of these carriers may also be used. Useful solid carriers for granules include, for example, crushed and classified natural rocks, such as calcite, marble, pumice, sepiolite, dolomite, and synthetic particles of inorganic and organic cereals, and particles of organic materials such as sawdust, coconut shells, corn cob cobs and tobacco stalks.

[0287] Suitable liquefied gas extenders or carriers are liquids which are gaseous at standard temperature and atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons, or butane, propane, nitrogen and carbon dioxide.

[0288] In the preparation, viscosity enhancers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids such as cephalin and lecithin, and synthetic phospholipids can be used. Other additives can be mineral oils and vegetable oils.

[0289] When the extender used is water, it is also possible to use, for example, an organic solvent as a cosolvent. Useful liquid solvents mainly include: aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffin, for example mineral oil fractions, mineral oils and vegetable oils, alcohols such as butanol or ethylene glycol and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

[0290] The composition of the present invention may additionally contain other components, such as surfactants. Useful surfactants are those having ionic or nonionic

[0291] Emulsifiers and / or foam formers, dispersants or wetting agents of a nature, or mixtures of these surfactants. Examples are polyacrylates, lignin sulfonates, phenol sulfonates or naphthalene sulfonates, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinates, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or polyethoxylated phenols, fatty acid esters of polyols and derivatives of compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysates, lignin sulfite waste liquors and methylcellulose. If one of the active ingredients and / or one of the inert carriers is insoluble in water and the application is carried out in water, the presence of a surfactant is necessary. The proportion of the surfactant is 5 to 40% by weight of the composition according to the invention. Dyes such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be used.

[0292] If suitable, other additional components may also be present, such as protective colloids, adhesives, binders, thickeners, thixotropic substances, penetrants, stabilizers, chelating agents, complexing agents. In general, the active ingredient may be combined with any solid or liquid additive that is conventionally used for formulation purposes. In general, the active ingredient contained in the compositions and preparations of the present invention is 0.05% to 99% by weight, 0.01% to 98% by weight, preferably 0.1% to 95% by weight, more preferably 0.5% to 90% by weight, most preferably 10% to 70% by weight. The active ingredient or composition of the present invention can be used as such, or, depending on their respective physical and / or chemical properties, in the form of a formulation or a use form prepared therefrom, such as an aerosol, a microcapsule suspension, a cold mist concentrate, a warm mist concentrate, a microcapsule granule, a fine granule, a seed treatment suspension, a ready-to-use solution, a dustable powder, an emulsifiable concentrate, an emulsion in water, an oil emulsion, a large granule, a microgranule, an oil-dispersible powder, an oil suspension, an oil, a foam, a paste, a pesticide-coated seed, a suspension, a suspoemulsion, a soluble solution, a suspension, a sprayable powder, a soluble powder, a dust and granule, a water-soluble granule or tablet, a water-soluble powder for seed treatment, a wettable powder, natural products and synthetic substances impregnated with the active ingredient, and microcapsules in polymeric substances and seed coating materials, and ULV cold mist and warm mist formulations.

[0293] The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredient with at least one customary extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, optionally drying agent and UV stabilizer and optionally dyes and pigments, defoamers, preservatives, secondary thickeners, tackifiers, gibberellins and other processing aids.

[0294] The compositions according to the invention include not only preparations which are ready for use and can be applied to plants or seeds with suitable equipment, but also commercial concentrates which have to be diluted with water before use.

[0295] The active ingredients according to the invention may be present as such or in their (commercially standard) formulations, or in use forms prepared from these formulations in the form of a mixture with other (known) active ingredients (e.g. insecticides, attractants, disinfectants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals).

[0296] The treatment of plants and plant parts with the active ingredients or compositions according to the invention is carried out directly by customary treatment methods or by acting on their surroundings, habitat or storage space, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigation, and in the case of propagation materials, in particular seeds, by dry seed treatment, wet seed treatment, slurry treatment, crusting, coating with one or more coatings, etc. The active ingredients can also be applied by the ultra-low volume method or by injecting the active ingredient preparation or the active ingredient itself into the soil.

[0297] One of the advantages of the present invention is that the specific systemic properties of the active ingredients and compositions of the present invention mean that treatment of the seed with these active ingredients and compositions protects not only the seed itself, but also the resulting plant after emergence from damage by phytopathogenic fungi. In this way, direct treatment of the crop at sowing or shortly after sowing can be dispensed with.

[0298] It is also considered advantageous that the active ingredients or compositions according to the invention can also be used in particular for transgenic seeds, in which case the plants grown from the seeds are able to express proteins that combat harmful organisms. Treatment of such seeds with the active ingredients or compositions according to the invention can lead to the control of certain harmful organisms simply through the expression of proteins (e.g. insecticidal proteins). Surprisingly, in this case, other synergistic effects can be observed, which further increase the effectiveness of preventing pest attacks.

[0299] The composition of the invention is suitable for protecting seeds of any plant variety used in agriculture, greenhouses, forestry or horticulture and viticulture. In particular, the seeds are seeds of cereals (e.g. wheat, barley, rye, triticale, sorghum / millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (e.g. sugar beets and fodder beets), peanuts, rapeseed, poppy, olives, coconuts, cocoa, sugar cane, tobacco, vegetables (e.g. tomatoes, cucumbers, onions and lettuce), turf and ornamental plants (see also below). The treatment of cereals (e.g. wheat, barley, rye, triticale and oats), corn and rice seeds is particularly important.

[0300] As described below, the treatment of transgenic seeds with the active ingredients or compositions according to the invention is of particular interest. This relates to plant seeds containing at least one heterologous gene capable of expressing a polypeptide or protein with insecticidal properties. The heterologous gene in the transgenic seeds may originate, for example, from microorganisms of the genera Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The heterologous gene preferably originates from a Bacillus species, in which case the gene product is effective against European corn borer and / or western corn rootworm. The heterologous gene more preferably originates from Bacillus thuringiensis.

[0301] In the context of the present invention, the composition of the present invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state where it is sufficiently stable to not be damaged during the treatment process. In general, the seed can be treated at any time between harvesting and sowing. It is customary to use seeds that are separated from the plant and do not contain cobs, shells, stems, epidermis, hairs or pulp. For example, seeds that have been harvested, cleaned and dried to a moisture content of less than 15% by weight can be used. Alternatively, seeds that are treated with water after drying and then dried again, for example, can also be used.

[0302] In general, when treating seed, it must be ensured that the amount of the composition according to the invention and / or other additives applied to the seed is chosen so that germination of the seed is not impaired and the plant grown therefrom is not harmed. This must be ensured in particular in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

[0303] The composition of the present invention can be applied directly, i.e. without comprising any other components and without dilution. Usually, the composition is preferably applied to the seed in a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described in, for example, US 4,272,417A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003 / 0176428A1, WO 2002 / 080675 A1, WO 2002 / 028186 A2.

[0304] The active ingredients used according to the invention can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, pastes or other seed coating compositions, and ULV formulations.

[0305] These formulations are prepared in a known manner by mixing the active ingredients with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, binders, gibberellins and also water.

[0306] Dyes that may be present in the seed dressing formulations usable according to the invention are all dyes commonly used for such purposes. Pigments that are sparingly soluble in water or dyes that are readily soluble in water may be used. Examples include the dyes known by the names Rhodamine B, CI Pigment Red 112 and CISolvent Red 1.

[0307] Useful wetting agents that may be present in the seed dressing formulations which can be used according to the invention are all substances which promote wetting and are customarily used in the formulation of agrochemical active ingredients. Alkylnaphthalenesulfonates, such as diisopropylnaphthalenesulfonate or diisobutylnaphthalenesulfonate, can preferably be used.

[0308] Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants which are usually used for the formulation of agrochemical active ingredients. It is preferred to use nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include in particular ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and phosphated or sulfated derivatives thereof. Suitable anionic dispersants are in particular lignin sulfonates, polyacrylates and arylsulfonate-formaldehyde condensates.

[0309] Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances which are customary for the formulation of agrochemical active ingredients. Silicone defoamers and magnesium stearate can preferably be used.

[0310] Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorobenzene and benzyl alcohol hemiformal.

[0311] Secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silica.

[0312] Useful binders which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in seed dressing products. Preferred examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and methylcellulose (tylose).

[0313] The seed dressing formulations usable according to the invention can be used directly or after prior dilution with water to treat a wide range of different seeds, including seeds of transgenic plants. In this case, the interaction with the substances formed by expression may also produce additional synergistic effects.

[0314] For treating the seed with the seed dressing formulations which can be used according to the invention or with the formulations prepared therefrom by adding water, useful apparatus are all mixing devices which can usually be used for seed dressing. In particular, the seed dressing method consists in placing the seed in a mixer, adding the seed dressing formulation itself or the seed dressing formulation diluted with water in the specific desired amount, and mixing them until the formulation is evenly distributed on the seed. If appropriate, this is followed by a drying operation.

[0315] Due to good plant compatibility, favorable thermotoxicity and good environmental compatibility, the active ingredients according to the invention are suitable for protecting plants and plant organs, increasing harvest yields and improving the quality of harvested crops. They can preferably be used as crop protection agents. They are active against normally sensitive and resistant species and against all or specific development stages.

[0316] Plants that can be treated according to the invention include the following major crop plants: corn, soybeans, cotton, Brassica oilseeds, such as rapeseed (e.g. Canola), Brassica rapa, B. juncea (e.g. (field) mustard) and Brassica carinata, rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, grapes and various fruits and vegetables from various botanical taxa, such as Rosaceae sp. (e.g., pome fruits such as apples and pears, and stone fruits such as apricots, cherries, almonds and peaches, and berries such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp. sp.), Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g. banana trees and banana plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g. lemons, oranges and grapefruit), Solanaceae sp. (e.g. tomatoes, potatoes, peppers, eggplants), Liliaceae sp., Compositae sp. (e.g. lettuce, artichokes and chicory - including root chicory, European chicory or common chicory), Umbelliferae sp. (e.g. sp.) (e.g., carrots, parsley, celery and celeriac), Cucurbitaceae sp. (e.g., cucumbers - including gherkins, pumpkins, watermelons, gourds and melons), Alliaceae sp. (e.g., leeks and onions), Cruciferae sp. (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radish, horseradish, cress and Chinese cabbage), Leguminosae sp. (e.g., peanuts, peas and beans - such as beans and broad beans), Chenopodiaceae sp. (e.g., cauliflower, cabbage, cauliflower, broccoli, cauliflower, brussels sprouts, pakchoi, kohlrabi, radish, horseradish, cress and Chinese cabbage), Leguminosae sp. (e.g., peanuts, peas and beans - such as beans and broad beans), Chenopodiaceae sp. (e.g., cauliflower, broccoli, cauliflower, broccoli, cauliflower, cauliflower, cauliflower, cauliflower and Chinese cabbage),) (e.g. Swiss chard, fodder beets, spinach, beetroot), Malvaceae (e.g. okra), Asparagaceae (e.g. asparagus); useful and ornamental plants for gardens and forests; and, in each case, genetically modified forms of these plants.

[0317] As mentioned above, all plants and their parts can be treated according to the present invention. In a preferred embodiment, wild plant species and plant cultivars, or those plants and their parts obtained by traditional biological breeding techniques (such as hybridization or protoplast fusion) are treated. In another preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) and their parts obtained by genetic engineering methods (if appropriate in combination with traditional methods) are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. According to the present invention, it is particularly preferred that plants of each commercially available conventional plant cultivar or those plants in use are treated. Plant cultivars are understood to mean plants with new properties ("traits") cultivated by conventional breeding, by mutagenesis or by recombinant DNA technology. They can be cultivars, varieties, biotypes and genotypes.

[0318] The treatment method of the present invention can be used for treating genetically modified organisms (GMO), such as plants or seeds.Genetically modified plants (or transgenic plants) refer to plants into which heterologous genes have been stably integrated into the genome.Term "heterologous gene" essentially means such a gene, which is provided or assembled outside the plant, and after the gene is introduced into the nuclear genome, chloroplast genome or mitochondrial genome, due to its expression of a protein or polypeptide of interest or another gene present in the plant, or other genes present in the plant are downregulated or closed (such as by antisense technology, co-suppression technology or RNAi technology [RNA interference]), and agronomy or other characteristics new or improved are given to the transformed plant.The heterologous gene located in the genome is also referred to as transgenic.The transgenic defined by its specific presence in the plant genome is called conversion or transgenic event.

[0319] Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also lead to superadditive ("synergistic") effects. For example, the following effects are possible that exceed the actual expected effect: reduced application rates and / or broadened activity spectrum and / or enhanced efficacy of the active ingredients and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher harvest yield, larger fruits, taller plant height, greener leaves, earlier flowering, higher quality and / or higher nutritional value of the harvested product, higher sugar concentration in the fruit, better storage stability and / or better processability of the harvested product.

[0320] Under certain application rates, the active ingredient combinations of the present invention can also have a strengthening effect on plants. Therefore, they are suitable for mobilizing the defense system of plants to resist the attack of unwanted plant pathogenic fungi and / or microorganisms and / or viruses. This may be one of the reasons why the activity of the composition of the present invention is enhanced, for example, antifungal. Plant strengthening (resistance induction) substances should be understood in this article to mean those substances or material compositions that can stimulate the plant defense system in the following manner: when the unwanted plant pathogenic fungi are subsequently inoculated, the plants processed show a great degree of resistance to these unwanted plant pathogenic fungi. Therefore, the material of the present invention can be used to protect plants from the attack of the mentioned pathogens in a specific time period after the treatment. After the plant is treated with the active ingredient, the period for achieving protection is usually extended by 1 to 10 days, preferably 1 to 7 days.

[0321] Plants and plant cultivars which are preferably treated according to the invention include all plants which have genetic material which imparts particularly advantageous, useful traits to these plants (whether obtained by breeding and / or biotechnological means).

[0322] Likewise preferably, the plants and plant cultivars to be treated according to the invention are resistant to one or more biotic stress factors, meaning that these plants are better defended against animal and microbial pests (for example nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids).

[0323] Examples of nematode-resistant plants are described, for example, in the following U.S. patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 11 / 657,964, 12 / 192,904, 11 / 396,808, 12 / 166,253, 12 / 166,239, 12 / 166,124, 12 / 166,209, 11 / 762,886, 12 / 364,335, 11 / 763,947, 12 / 252,453, 12 / 209,354, 12 / 491,396, and 12 / 497,221.

[0324] Plants and plant cultivars that may also be treated according to the invention are those that are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, drought, low temperature exposure, heat exposure, osmotic stress, waterlogging, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, or lack of shade.

[0325] Plants and plant varieties that can also be processed according to the present invention are those plants characterized by the yield characteristics of improvement. The yield that improves in the described plant can be the result of the following factors: for example, improved plant physiological function, growth and development, such as water use efficiency, water holding efficiency, improved nitrogen utilization rate, enhanced carbon assimilation, improved photosynthesis, improved germination rate and accelerated maturity. Yield can also be affected by the improved plant architecture (under stress and non-stress conditions), including but not limited to: early flowering, flowering control to hybrid seed production, rice seedling vigor, plant size, internode number and internode distance, root growth, seed size, fruit size, pod size, pod number or ear number, seed quantity of each pod or ear, seed quality, enhanced seed fullness, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Other yield characteristics include seed composition, such as carbohydrate content, protein content, oil content and oil composition, nutritional value, anti-nutritional compounds reduction, improved processability and better storage stability.

[0326] Plants that can be treated according to the present invention are hybrid plants that have shown heterosis or hybrid effect characteristics, which generally result in higher yields, vigor, better health and resistance to biological and abiotic stress factors. Such plants are generally produced by hybridizing an inbred male sterile parent line (female crossbreeding parent) with another inbred male fertile parent line (male crossbreeding parent). Hybrid seeds are generally harvested from male sterile plants and sold to growers. Male sterile plants can sometimes (for example in corn) be produced by emasculation (i.e. mechanical removal of male reproductive organs or male flowers), but more typically, male sterility is the result of genetic determinants in the plant genome. In this case, particularly when seed is the desired product harvested from a hybrid plant, it is generally beneficial to ensure that male fertility in the hybrid plant is fully restored, wherein the hybrid plant contains genetic determinants that cause male sterility. This can be achieved by ensuring that the male cross breeding parent has a suitable fertility restorer gene, which can restore male fertility in a hybrid plant containing a genetic determinant that causes male sterility. The genetic determinant of male sterility can be located in the cytoplasm. For example, examples of cytoplasmic male sterility (CMS) of Brassica species are recorded. However, the genetic determinant of male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. The particularly useful method for obtaining male sterile plants is recorded in WO 89 / 10396, wherein for example ribonucleases such as barnase (barnase) are selectively expressed in the tapetum cells of stamens. Then, fertility can be restored by expressing ribonuclease inhibitors such as barstar in the tapetum cells.

[0327] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that impart such herbicide tolerance.

[0328] Plants tolerant to herbicides are, for example, plants tolerant to glyphosate, i.e. plants tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate by various methods. Thus, for example, plants tolerant to glyphosate can be obtained by transforming plants with genes encoding 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science, 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the gene encoding the petunia EPSPS (Shah et al., 1986, Science 233, 478-481), the tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or the Eleusine EPSPS (WO 01 / 66704). It may also be a mutated EPSPS. Plants tolerant to glyphosate may also be obtained by expressing a gene encoding a glyphosate oxidoreductase. Plants tolerant to glyphosate can also be obtained by expressing a gene encoding a glyphosate acetyltransferase. Plants tolerant to glyphosate can also be obtained by selecting plants containing naturally occurring mutations of the above genes. Plants expressing the EPSPS gene that confers glyphosate tolerance have been documented. Plants expressing other genes such as decarboxylase genes that confer glyphosate tolerance have been documented.

[0329] Other herbicide-resistant plants are, for example, plants that tolerate herbicides that inhibit glutamine synthase (e.g., bialaphos, phosphinothricin, or glufosinate). Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of glutamine synthetase that resists inhibition. An example of such an effective detoxifying enzyme is an enzyme encoding phosphinothricin acetyltransferase (e.g., bar or pat proteins from Streptomyces). Plants expressing exogenous phosphinothricin acetyltransferase have been documented.

[0330] Other herbicide-tolerant plants are also plants that have been rendered tolerant to herbicides that inhibit hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenase is an enzyme that catalyzes a reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors can be transformed with genes encoding naturally occurring anti-HPPD enzymes or genes encoding mutant or chimeric HPPD enzymes, as described in WO 96 / 38567, WO 99 / 24585, WO 99 / 24586, WO 2009 / 144079, WO 2002 / 046387 or US 6,768,044. Tolerance to HPPD inhibitors can also be obtained by transforming plants with genes encoding certain specific enzymes capable of forming homogentisate, despite the fact that the HPPD inhibitors inhibit the natural HPPD enzyme. Such plants are described in WO 99 / 34008 and WO 02 / 36787. In addition to genes encoding HPPD-tolerant enzymes, plants can also be transformed with genes encoding prephenate dehydrogenases to improve tolerance to HPPD inhibitors, as described in WO 2004 / 024928. In addition, plants can be made more tolerant to HPPD inhibitors by inserting genes encoding enzymes that metabolize or degrade HPPD inhibitors (e.g., CYP450 enzymes) into their genome (see WO 2007 / 103567 and WO 2008 / 150473).

[0331] Other herbicide-resistant plants are plants that are tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylureas, imidazolinones, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the known ALS enzyme (also known as acetohydroxyacid synthase, AHAS) confer tolerance to different herbicides and groups of herbicides, as described, for example, in Tranel and Wright (Weed Science 2002, 50, 700-712). The production of plants tolerant to sulfonylureas and plants tolerant to imidazolinones has been documented. Other plants tolerant to sulfonylureas and imidazolinones have also been documented.

[0332] Other plants tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutations, by selection in cell cultures in the presence of the herbicide or by mutagenesis breeding (see, for example, US 5,084,082 for soybeans, WO 97 / 41218 for rice, US 5,773,702 and WO 99 / 057965 for sugar beet, US 5,198,599 for lettuce or WO 01 / 065922 for sunflower).

[0333] Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that impart such insect resistance.

[0334] As used herein, the term "insect-resistant transgenic plant" includes any plant containing at least one transgene comprising a coding sequence encoding:

[0335] 1) insecticidal crystal proteins of Bacillus thuringiensis or insecticidal parts thereof, such as those compiled by Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807-813) and updated by Crickmore et al. (2005) in the Glossary of Bacillus thuringiensis Toxins (online address: http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / ), or insecticidal parts thereof, such as proteins of the Cry protein classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa or Cry3Bb or insecticidal parts thereof (e.g. EP-A 1999141 and WO 2007 / 107302), or those encoded by synthetic genes, such as those described in U.S. Patent Application No. 12 / 249,016; or

[0336] 2) a crystal protein of Bacillus thuringiensis or a portion thereof, which is insecticidal in the presence of a second crystal protein other than Bacillus thuringiensis or a portion thereof, such as a binary toxin composed of Cy34 and Cy35 crystal proteins (Nat. Biotechnol. 2001, 19, 668-72; Applied Environm. Microbiol. 2006, 71, 1765-1774) or a binary toxin composed of Cry1A or Cry1F protein and Cry2Aa or Cry2Ab or Cry2Ae protein (U.S. Patent Application No. 12 / 214,022 and EP08010791.5); or

[0337] 3) a hybrid insecticidal protein comprising parts of two different insecticidal crystal proteins of Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, such as the Cry1A.105 protein produced by corn event MON98034 (WO 2007 / 027777); or

[0338] 4) A protein of any one of 1) to 3) above, wherein some, in particular 1 to 10, amino acids are substituted by another amino acid to obtain higher insecticidal activity against target insect species, and / or to expand the range of target insect species affected, and / or due to changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn event MON863 or MON88017, or the Cry3A protein in corn event MIR604; or

[0339] 5) insecticidal secretory proteins of Bacillus thuringiensis or Bacillus cereus, or insecticidal parts thereof, such as the vegetative insecticidal proteins (VIPs) listed at http: / / www.lifesci.sussex.ac.uk / home / Neil_Crickmore / Bt / vip.html, such as proteins of the VIP3Aa protein class; or

[0340] 6) a secretory protein of Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secretory protein of Bacillus thuringiensis or Bacillus cereus, such as a binary toxin consisting of VIP1A and VIP2A proteins (WO 94 / 21795); or

[0341] 7) a hybrid insecticidal protein comprising parts of different secretory proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or

[0342] 8) The protein of any of the above points 5) to 7), wherein some, in particular 1 to 10, amino acids have been substituted with another amino acid to obtain higher insecticidal activity against target insect species, and / or to expand the range of target insect species affected, and / or due to changes induced in the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT 102; or

[0343] 9) secretory proteins of Bacillus thuringiensis or Bacillus cereus, which are insecticidal in the presence of crystallized proteins of Bacillus thuringiensis, such as binary toxins composed of proteins VIP3 and Cry1A or Cry1F (U.S. patent applications 61 / 126083 and 61 / 195019), or binary toxins composed of VIP3 protein and Cry2Aa or Cry2Ab or Cry2Ae protein (U.S. patent application 12 / 214,022 and EP 08010791.5); or

[0344] 10) A protein according to point 9) above, wherein some, in particular 1 to 10, amino acids have been substituted by another amino acid to obtain higher insecticidal activity against target insect species, and / or to expand the range of target insect species affected, and / or due to changes induced in the encoding DNA during cloning or transformation (while still encoding an insecticidal protein).

[0345] Of course, the insect-resistant transgenic plants used herein also include any plants containing a combination of genes encoding any of the proteins in categories 1 to 10 above. In one embodiment, the insect-resistant plant contains more than one transgene encoding any of the proteins in categories 1 to 10 above, by using different proteins that are insecticidal to the same target insect species but have different modes of action (e.g., binding to different receptor binding sites in insects) to expand the range of target insect species affected or delay the development of insect resistance to the plant.

[0346] As used herein, "insect-resistant transgenic plants" additionally include any plant containing at least one transgene containing a sequence for producing double-stranded RNA that prevents the growth of an insect pest after the pest has consumed a food product.

[0347] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing mutations imparting such stress resistance. Particularly useful stress-tolerant plants include:

[0348] a. A plant containing a transgenic plant capable of reducing the expression and / or activity of a poly(ADP-ribose) polymerase (PARP) gene in a plant cell or plant;

[0349] b. Plants containing a transgenic plant that reduces the expression and / or activity of a PARG encoding gene in a plant or plant cell and enhances stress tolerance;

[0350] c. A plant containing a transgene that enhances stress tolerance, wherein the transgene encodes a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotinatephosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.

[0351] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and / or storage stability of the harvested products and / or altered properties of specific components of the harvested products, for example:

[0352] 1) Transgenic plants that synthesize modified starch, wherein the physicochemical characteristics of the modified starch, in particular the amylose content or amylose / amylopectin ratio, degree of branching, average chain length, side chain distribution, viscosity behavior, gel strength, starch granule size and / or starch granule morphology are changed compared to the synthesized starch in wild-type plant cells or plants, so that the modified starch is better suitable for specific purposes.

[0353] 2) Transgenic plants that synthesize non-starch carbohydrate polymers or synthesize non-starch carbohydrate polymers with altered properties compared to wild-type plants that have not been genetically modified. Examples are: plants that produce polyfructose, especially inulin and fructan types, plants that produce α-1,4-glucans, plants that produce α-1,6-branched α-1,4-glucans, and plants that produce alternans.

[0354] 3) Transgenic plants producing hyaluronic acid.

[0355] 4) Transgenic plants or hybrid plants, such as onions, with special properties, such as "high soluble solids content", "low pungency" (LP) and / or "long storage" (LS).

[0356] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber properties. These plants can be obtained by genetic transformation, or by screening for plants containing mutations imparting these altered fiber properties, and include:

[0357] a) plants, such as cotton plants, containing a variant of a cellulose synthase gene;

[0358] b) plants, such as cotton plants, containing a variant of a rsw2 or rsw3 homologous nucleic acid, such as a cotton plant with increased expression of sucrose phosphate synthase;

[0359] c) plants, such as cotton plants, having increased expression of sucrose synthase;

[0360] d) plants such as cotton plants, in which the timing of plasmodesmata gating at the base of fiber cells is altered, for example by downregulation of fiber-selective β-1,3-glucanase;

[0361] e) Plants, such as cotton plants, having fibers with altered responsiveness, for example by expressing N-acetylglucosamine transferase genes including nodC and chitin synthase genes.

[0362] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil composition characteristics. Such plants can be obtained by genetic transformation or by screening for plants containing mutations imparting these altered oil properties, and include:

[0363] a) Plants producing oil with a high oleic acid content, such as oilseed rape plants;

[0364] b) plants producing oil with a low linolenic acid content, such as oilseed rape plants;

[0365] c) Plants which produce oils having a low saturated fatty acid content, such as oilseed rape plants.

[0366] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering) that may also be treated according to the invention are plants such as potato that are virus-resistant, for example to potato virus Y (SY230 and SY233 events from Tecnoplant, Argentina), or that are resistant to diseases such as potato late blight (for example the RB gene), or that exhibit reduced low-temperature-induced sweetness (that carry the genes Nt-Inh, II-INV) or that exhibit a dwarf phenotype (A-20 oxidase gene).

[0367] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation imparting such altered characteristics, and include plants, such as oilseed rape, with delayed or reduced seed shattering.

[0368] Particularly useful transgenic plants that can be treated according to the present invention are plants with a transformation event or combination of transformation events that are the subject of a non-regulated status application granted or pending by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) in the United States. Information related thereto can be obtained at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), for example, via the website http: / / www.aphis.usda.gov / brs / not_reg.html. On the filing date of this application, an application containing the following information has been approved or pending at APHIS:

[0369] - Application: Identification number of the application. Technical descriptions of transformation events can be found in the specific application documents obtained by application number on the APHIS website. These descriptions are disclosed herein by reference.

[0370] -Extension of application: refers to a request to extend the scope or duration of an earlier application.

[0371] -Institution: The name of the person submitting the application.

[0372] - Regulated items: relevant plant species.

[0373] - Transgenic phenotype: A trait conferred to a plant by a transformation event.

[0374] - Transformation Event or Transformation Strain: The name of the event (sometimes also called the strain) for which non-regulated status is requested.

[0375] -APHIS Documents: Various documents that APHIS has published regarding the application or that are available from APHIS upon request.

[0376] Particularly useful transgenic plants which can be treated according to the invention are plants which contain one or more genes encoding one or more toxins, such as the transgenic plants sold under the trade name: YIELD (e.g. corn, cotton, soybeans), (such as corn), (such as corn), (such as corn), (such as corn), (cotton), (cotton), (cotton), (such as corn), and (potato). Examples of herbicide-tolerant plants which may be mentioned include maize varieties, cotton varieties and soybean varieties available under the following trade names: Roundup (glyphosate-tolerant, e.g. corn, cotton, soybean), Liberty (phosphinothricin-resistant, e.g. oilseed rape), (Imidazolinone resistant) and (tolerant to sulfonylureas), for example corn. Herbicide-tolerant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include those marketed under the name The variety of corn sold.

[0377] Particularly useful transgenic plants which may be treated according to the invention are plants which contain a transformation event or a combination of transformation events and which are listed, for example, in the databases of various national or regional regulatory agencies (see, for example, http: / / gmoinfo.jrc.it / gmp_browse.aspx and http: / / cera-gmc.org / index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit).

[0378] The active ingredients or compositions according to the invention can also be used in the protection of materials, in order to protect industrial materials from attack and destruction by unwanted microorganisms, such as fungi and insects.

[0379] Furthermore, the compounds of the present invention can be used as antifouling compositions alone or in combination with other active ingredients.

[0380] In this article, industrial materials are understood to mean non-biological materials prepared for use in industry. For example, industrial materials protected from microbial changes or destruction by the active ingredient of the present invention can be adhesives, sizing agents (sizes), paper, wallpaper and cardboard, textiles, carpets, leather, wood, paints and plastic products, cooling lubricants and other materials that can be infected or destroyed by microorganisms. The range of materials to be protected also includes parts of production plants and buildings, such as cooling water circuits, cooling and heating systems, and ventilation systems and air-conditioning systems, which may be damaged by the breeding of microorganisms. Industrial materials within the scope of the present invention preferably include adhesives, sizing agents, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood. Active ingredients or compositions of the present invention can prevent adverse effects, such as rotting, decomposition, discoloration, decolorization or the formation of mold. In addition, the compounds of the present invention can be used to protect objects (especially hulls, screens, fishing nets, buildings, mooring equipment and signal systems) in contact with salt water or brackish water from being contaminated.

[0381] The method for preventing and treating unwanted fungi of the present invention can also be used for protecting stored goods." stored goods " is understood to mean natural substances or processed products thereof from natural plant sources or animal sources, and it is necessary to protect them for a long time. Stored goods of plant origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected by (pre) drying, moistening, crushing, grinding, pressing or baking after fresh harvest or processing. Stored goods also include wood, whether it is unprocessed wood, such as building wood, electric poles and obstacles, or wood in finished product form, such as furniture. Stored goods of animal origin are, for example, raw hides, leather, fur and hair. Active ingredients of the present invention can prevent adverse effects, such as rotting, decomposition, discoloration, discoloration or the formation of mold.

[0382] Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include: diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaeraleucotricha; Sphaerotheca species, such as Sphaerothecafuliginea; Uncinula species, such as Uncinula necator; diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora spp. species, such as Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, such as Puccinia recondita or Puccinia triticina; Uromyces species, such as Uromyces appendiculatus; diseases caused by pathogens from the oomycetes, such as Bremia species, such as Bremialactucae; Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmoparaviticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis;Pythium species, for example Pythium ultimum; leaf blotch disease and leaf wilt disease caused by, for example, Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium); Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoefawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Microdochium species, for example Microdochium nivale;Mycosphaerella species, such as Mycosphaerelle graminicola and M.fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Rhizoctonia species, such as Rhizoctonia solani; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis solani; basicola); ear and panicle diseases (including corn crops) caused by, for example, Alternaria species, such as Alternaria species; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium species; Claviceps species, such as Claviceps purpurea;Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Septoria species, such as Septoria nodorum; diseases caused by smut fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries, T. controversy; Urocystis species, such as Urocystis occulta; Ustilago Nuda, U. nuda tritici; fruit rot caused by, for example, Aspergillus species, for example, Aspergillus flavus; Botrytis species, for example, Botrytis cinerea; Penicillium species, for example, Penicillium expansum and P. purpurogenum; Sclerotinia species, for example, Sclerotinia sclerotiorum; Verticilium species, for example, Verticilium alboatrum; seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by, for example, Fusarium species, for example, Fusarium sclerotiorum. culmorum); Phytophthora species (e.g., Phytophthora cactorum); Pythium species (e.g., Pythium ultimum); Rhizoctonia species, e.g., Rhizoctonia solani; Sclerotium species, e.g., Sclerotium rolfsii;Cancerous diseases, galls and broomcorn diseases caused by pathogens such as Nectria species, for example Nectria galligena;

[0383] Wilt diseases caused by pathogens such as Monilinia species, such as Monilinia laxa;

[0384] Deformations of leaves, flowers and fruits caused by, for example, Taphrina species, such as Taphrina deformans; degenerative diseases of woody plants caused by, for example, Esca species, such as Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;

[0385] Diseases of flowers and seeds caused by pathogens such as Botrytis species (e.g. Botrytis cinerea); diseases of plant tubers caused by pathogens such as Rhizoctonia species (e.g. Rhizoctonia solani), Helminthosporium species, e.g. Helminthosporium solani; diseases caused by bacterial pathogens such as Xanthomonas species, e.g. Xanthomonas campestris pv. oryzae; Pseudomonas species, e.g. Pseudomonas syringae pv. lachrymans; Erwinia species, e.g. Erwinia amylovora.

[0386] The following soybean diseases can be controlled preferentially:

[0387] Fungal diseases of leaves, stems, pods and seeds caused by pathogens such as alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora), dactuliophora leaf spot (Dactuliophora glycines), soybean downy mildew (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora), dactuliophora leaf spot (Dactuliophora glycines), soybean downy mildew (Septoria glycines), soybean spores ... mildew (Peronospora manshurica), rechslera wilt (Drechslera glycini), frogeye (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem wilt (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

[0388] Fungal diseases at the base of the root and stem caused by pathogens such as blackroot rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var.caulivora), Phytophthora rot (Phytophthora megasperma), Brown stem rot (Phialophora gregata), Pythium diseases (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia root rot, stem rot and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia white rot (Sclerotinia rolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0389] Microorganisms capable of degrading or modifying industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The active ingredients according to the invention preferably act on fungi, in particular molds, wood-discoloring and wood-destroying fungi (Basidiomycetes), as well as on slime organisms and algae. Examples include microorganisms of the genera Alternaria, such as Alternaria tenuis; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; viride); Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.

[0390] In addition, the active ingredients according to the invention also have very good antifungal activity. They have a very broad spectrum of antifungal activity, in particular against dermatophytes and yeasts, molds and diphasic fungi (e.g. against Candida species, such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species (e.g. Aspergillus niger and Aspergillus fumigatus), Trichophyton species (e.g. Trichophyton mentagrophytes), Microsporon species (e.g. Microsporon canis) and audouinii. The enumeration of these fungi in no way constitutes a restriction of the fungal spectrum that can be controlled, but has only an illustrative character.

[0391] Therefore, the active ingredients of the present invention can be used for both medical and non-medical applications.

[0392] If appropriate, the compounds according to the invention can also be used as herbicides, safeners, growth regulators or agents for improving plant properties at certain concentrations or application rates, or as microbicides, for example fungicides, antifungals, bactericides, viricides (including anti-viroid agents) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). As appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0393] The following examples illustrate the invention.

[0394] A. Chemical Examples

[0395] 4-Bromo-2-chloro-N 3 -ethyl-N 1 -Synthesis of (1-methyl-1H-tetrazolyl-5-yl)isophthalimide (Example No. 1-178)

[0396] Step 1: Preparation of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic acid

[0397] First, 1.47g (5.29mmol) of 4-bromo-2-chloro-3-formylbenzoic acid methyl ester was fed into 100ml of acetone. A solution of 636mg (6.35mmol) of chromium oxide (VI) in dilute sulfuric acid (H2O:H2SO4 3:1) was slowly added dropwise. The mixture was heated to room temperature and stirred for 12 hours. Thereafter, a small amount of isopropanol was added, and the mixture was concentrated under reduced pressure. The residue was absorbed in water and extracted with ethyl acetate, and the organic phase was dried and concentrated to a dry state. 1.23g of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic acid was obtained.

[0398] 1 H-NMR (400MHz, DMSO-d6): δ = 14.30 (br s, 1H); 7.82 (d, 1H); 7.77 (d, 1H); 3.88 (s, 3H)

[0399] Step 2: Preparation of methyl 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoate

[0400] To an initial charge of 753 mg (2.56 mmol) of 6-bromo-2-chloro-3-(methoxycarbonyl)benzoic acid in 30 ml of dichloromethane was added a catalytic amount of dimethylformamide. Thereafter, 490 mg (3.84 mmol) of oxalyl chloride was added at room temperature and the mixture was stirred for a further hour. The mixture was concentrated to dryness and the residue was co-evaporated with toluene. The resulting residue was taken up in 5 ml of dichloromethane. At 0° C., an acid chloride solution was added to an initial charge of 1.9 ml (3.84 mmol) of ethylamine in tetrahydrofuran and 663 mg (5.13 mmol) of Hünig's base in 50 ml of dichloromethane. The mixture was stirred for a further 4 hours at room temperature. Thereafter, 100 ml of dichloromethane was added and the mixture was washed with a 2M aqueous hydrochloric acid solution. The organic phase was dried and concentrated to dryness. 773 mg of methyl 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoate were obtained.

[0401] 1 H-NMR (400MHz, DMSO-d6): δ = 8.68 (t, 1H); 7.77 (d, 1H); 7.69 (d, 1H); 3.87 (s, 3H); 3.28 (m, 2H); 1.12 (t, 3H).

[0402] Step 3: Preparation of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid

[0403] At room temperature, 192 mg (4.82 mmol) of 1M sodium hydroxide aqueous solution was added to 773 mg (2.41 mmol) of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid methyl ester dissolved in 80 ml of methanol. The mixture was stirred at 50 ° C for 12 hours and then concentrated to dryness. The residue was absorbed in a small amount of water, and the solution was acidified with 2M hydrochloric acid aqueous solution and extracted with dichloromethane. The organic phase was dried and concentrated. 582 g of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid was obtained.

[0404] 1 H-NMR (400MHz, DMSO-d6): δ = 13.69 (br s, 1H); 8.65 (t, 1H); 7.72 (d, 1H); 7.66 (d, 1H); 3.26 (m, 2H); 1.12 (t, 3H).

[0405] Step 4: 4-Bromo-2-chloro-N 3 -ethyl-N 1 Preparation of -(1-methyl-1H-tetrazolyl-5-yl)isophthalimide

[0406] At room temperature, 155 mg (1.22 mmol) of oxalyl chloride was added to an initial charge of 189 mg (0.61 mmol) of 4-bromo-2-chloro-3-(ethylcarbamoyl)benzoic acid and 93.5 mg (0.92 mmol) of 5-amino-1-methyl-1H-tetrazole dissolved in 3 ml of pyridine. The mixture was stirred for another 12 hours. 10 ml of water was added, followed by extraction with dichloromethane, and the organic phase was dried and concentrated. The residue was purified by column chromatography (HPLC, C18, gradient: acetonitrile / water (++0.05% trifluoroacetic acid), 10 / 90→100 / 0 in 30 minutes). 66 mg of 4-bromo-2-chloro-N 3 -ethyl-N 1 -(1-methyl-1H-tetrazol-5-yl)isophthalimide (Example No. 1-178).

[0407] The examples listed in the table below were prepared or are obtainable analogously to the methods described above. These compounds are very particularly preferred.

[0408] The abbreviations used in this article mean:

[0409] Me = methyl Bu = butyl Et = ethyl Pr = propyl c = cyclo

[0410] Ph = Phenyl

[0411] Table 1: Compounds of the general formula (I) of the present invention, wherein Q is Q 1 , Rx is methyl, and other substituents are defined as follows.

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423] Table 2: Compounds of the general formula (I) of the present invention, wherein Q is Q 1 , R x is ethyl, and other substituents are defined as follows.

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435] Table 3: Compounds of the general formula (I) of the present invention, wherein Q is Q 1 , R x is propyl, and other substituents are as defined below.

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446] Table 4: Compounds of the general formula (I) of the present invention, wherein Q is Q 2 , R x is methyl, and other substituents are defined as follows.

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455] Table 5: Compounds of the general formula (I) of the present invention, wherein Q is Q 4 , R z is hydrogen, and the other substituents are as defined below.

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464] Table 6: Compounds of the general formula (I) of the present invention, wherein Q is Q 4 , R z is methyl, and other substituents are defined as follows.

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474] The NMR data for many of the compounds of formula (I) of the present invention mentioned in the above table are disclosed below for further characterization:

[0475] Embodiment No. 1-4: 1 H-NMR (400MHz, DMSO-d6): δ = 11.63 (br s, 1H); 8.50 (q, 1H); 7.67 (d, 1H); 7.50 (d, 1H); 3.98 (s, 3H); 2.80 (d, 3H); 2.33 (s, 3H);

[0476] Embodiment No. 1-19: 1H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.57 (q, 1H); 7.94 (d, 1H); 7.89 (d, 1H); 4.01 (s, 3H); 3.27 (s, 3H); 2.78 (d, 3H); 2.35 (s, 3H);

[0477] Embodiment No. 1-20: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.63(t,1H);7.94(d,1H);7.88(d,1H);4.01(s,3H);3.27(m,2H);3.27(s,3H);2.38(s,3H);1.13(t,3H);

[0478] Embodiment No. 1-21: 1 H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s,1H);8.70(d,1H);7.93(d,1H);7.88(d,1H);4.00(s,3H);3.27(s,3H);2.78(m,1H);2.35(s,3H);0.69(m,2H);0.62(m,1H);0.51(m,1H);

[0479] Embodiment No. 1-25: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s, 1H); 8.51 (q, 1H); 7.83 (d, 1H); 7.76 (d, 1H); 4.00 (s, 3H); 2.79 (d, 3H); 2.34 (s, 3H);

[0480] Embodiment No. 1-26: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s, 1H); 8.49 (t, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 3.28 (m, 2H); 2.36 (s, 3H); 1.11 (t, 3H);

[0481] Embodiment No. 1-27: 1 H-NMR (400MHz, DMSO-d6): δ = 11.75 (br s,1H);8.66(d,1H);7.83(d,1H);7.75(d,1H);4.00(s,3H);2.81(m,1H);2.34(s,3H);0.71(m,2H);0.49(m,2H);

[0482] Embodiment No. 1-28: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s,1H);8.72(t,1H);7.83(d,1H);7.76(d,1H);4.01(s,3H);3.13(m,2H);2.38(s,3H);1.01(m,1H);0.45(m,2H);0.23(m,2H);

[0483] Embodiment No. 1-29: 1 H-NMR (400MHz, DMSO-d6): δ = 11.80 (br s, 1H); 9.38 (t, 1H); 7.88 (d, 1H); 7.80 (d, 1H); 4.13 (m, 2H); 4.01 (s, 3H); 2.35 (s, 3H);

[0484] Embodiment No. 1-30: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.09 (t, 1H); 7.86 (d, 1H); 7.78 (d, 1H); 6.13 (tt, 1H); 4.01 (s, 3H); 3.71 (2H); 2.36 (s, 3H);

[0485] Embodiment No. 1-31: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s,1H);8.62(t,1H);7.82(d,1H);7.75(d,1H);4.01(s,3H);3.40(m,1H);2.39(d,3H);1.20(dd,3H);0.91(m,1H);0.44(m,2H);0.29(m,2H);

[0486] Embodiment No. 1-32: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s,1H);8.81(t,1H);7.91(d,1H);7.78(d,1H);6.95(t,1H);4.01(s,3H);3.24(m,2H);1.54(m,2H);0.92(t,3H);

[0487] Embodiment No. 1-33: 1H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s,1H);8.51(d,1H);7.82(d,1H);7.75(d,1H);4.08(m,1H);4.00(s,3H);2.37(s,3H);1.16(d,3H);1.12(d,3H);

[0488] Embodiment No. 1-34: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s, 1H); 8.70 (d, 1H); 7.83 (d, 1H); 7.75 (d, 1H); 4.00 (s, 3H); 3.52-3.31 (m, 4H); 3.27 (s, 3H); 2.36 (s, 3H);

[0489] Embodiment No. 1-36: 1 H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.42 (t, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 4.49 (m, 2H); 4.01 (s, 3H); 2.35 (s, 3H);

[0490] Embodiment No. 1-37: 1 H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s, 1H); 8.72 (br s,1H);7.83(d,1H);7.75(d,1H);4.00(s,3H);3.97(m,1H);3.77(m,1H);3.63(m,1 H);3.35(m,1H);3.27(m,1H);2.36(s,3H);1.92(m,1H);1.83(m,2H);1.60(m,1H);

[0491] Embodiment No. 1-41: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s,1H);9.41(d,1H);7.87(d,1H);7.80(d,1H);4.98(m,1H);4.80(t,2H);4.54(t,1H);4.48(t,1H);4.01(s,3H);2.36(s,3H);

[0492] Embodiment No. 1-44: 1H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s, 1H); 8.56 (q, 1H); 7.80 (d, 1H); 7.63 (d, 1H); 6.91 (t, 1H); 4.00 (t, 1H); 2.80 (d, 3H); 2.33 (s, 3H);

[0493] Embodiment No. 1-45: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.65(t,1H);7.79(d,1H);7.63(d,1H);6.91(t,1H);4.00(s,3H);3.30(m,2H);2.35(s,3H);1.13(t,3H);

[0494] Embodiment No. 1-46: 1 H-NMR (400MHz, DMSO-d6): δ = 11.68 (br s,1H);8.71(d,1H);7.79(d,1H);7.62(d,1H);6.90(t,1H);3.99(s,3H);2.85(m,1H);2.33(s,3H);0.71(m,1H);0.54(m,2H);

[0495] Embodiment No. 1-47: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.79(t,1H);7.80(d,1H);7.64(d,1H);6.92(t,1H);4.00(s,3H);3.15(m,2H);2.38(s,3H);1.04(m,1H);0.46(m,2H);0.24(m,2H);

[0496] Embodiment No. 1-49: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);9.12(t,1H);7.82(d,1H);7.66(d,1H);6.93(t,1H);6.19(tt,1H);4.00(s,3H);3.72(m,2H);2.36(s,3H);

[0497] Embodiment No. 1-56: 1H-NMR (400MHz, DMSO-d6): δ = 11.66 (br s, 1H); 8.53 (q, 1H); 7.89 (d, 1H); 7.67 (d, 1H); 3.99 (s, 3H); 3.86 (s, 3H); 2.79 (d, 3H);

[0498] Embodiment No. 1-57: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.60 (t, 1H); 7.88 (d, 1H); 7.67 (d, 1H); 3.99 (s, 3H); 3.87 (s, 3H); 3.29 (m, 2H); 1.11 (t, 3H);

[0499] Embodiment No. 1-58: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s,1H);8.68(d,1H);7.88(d,1H);7.66(d,1H);3.99(s,3H);3.86(s,3H);2.80(m,1H);0.71(m,2H);0.49(m,2H);

[0500] Embodiment No. 1-72: 1 H-NMR (400MHz, DMSO-d6): δ = 11.53 (br s, 1H); 8.57 (q, 1H); 7.85 (d, 1H); 7.54 (d, 1H); 6.96 (t, 1H); 3.99 (s, 3H); 3.85 (s, 3H); 2.81 (d, 3H);

[0501] Embodiment No. 1-73: 1 H-NMR (400MHz, DMSO-d6): δ = 11.52 (br s,1H);8.65(t,1H);7.84(d,1H);7.54(d,1H);6.96(t,1H);3.99(s,3H);3.86(s,3H);3.20(m,2H);1.13(t,3H);

[0502] Embodiment No. 1-74: 1 H-NMR (400MHz, DMSO-d6): δ = 11.51 (br s,1H);8.72(d,1H);7.84(d,1H);7.52(d,1H);6.95(t,1H);3.98(s,3H);3.85(s,3H);2.85(m,1H);0.71(m,2H);0.54(m,2H);

[0503] Embodiment No. 1-81: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.48 (q, 1H); 7.95 (d, 1H); 7.88 (d, 1H); 4.05 (s, 3H); 2.80 (d, 3H); 2.43 (s, 3H);

[0504] Embodiment No. 1-82: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.56 (t, 1H); 7.95 (d, 1H); 7.88 (d, 1H); 4.06 (s, 3H); 3.32 (m, 2H); 2.44 (s, 3H); 1.14 (t, 3H);

[0505] Embodiment No. 1-83: 1 H-NMR (400MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.64 (d, 1H); 7.94 (d, 1H); 7.88 (d, 1H); 4.05 (s, 3H); 2.80 (m, 1H); 2.43 (s, 3H); 0.71 (m, 2H); 0.53 (br s,2H);

[0506] Embodiment No. 1-84: 1 H-NMR (400MHz, DMSO-d6): δ = 11.83 (br s,1H);8.68(t,1H);7.95(d,1H);7.87(d,1H);4.05(s,3H);3.16(m,2H);2.45(s,3H);1.02(m,1H);0.45(m,2H);0.24(m,2H);

[0507] Embodiment No. 1-86: 1 H-NMR (400MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.10 (t, 1H); 7.98 (d, 1H); 7.92 (d, 1H); 6.11 (tt, 1H); 4.05 (s, 3H); 3.71 (m, 2H); 2.43 (s, 3H);

[0508] Embodiment No. 1-87: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s, 1H); 8.54 (q, 1H); 7.81 (s, 2H); 6.90 (t, 1H); 4.04 (s, 3H); 2.82 (d, 3H); 2.42 (s, 3H);

[0509] Embodiment No. 1-88: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s, 1H); 8.62 (t, 1H); 7.82 (s, 2H); 6.91 (t, 1H); 4.05 (s, 3H); 3.33 (m, 2H); 2.43 (s, 3H); 1.16 (t, 3H);

[0510] Embodiment No. 1-89: 1 H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s, 1H); 8.70 (d, 1H); 7.81 (br s,2H);6.90(t,1H);4.05(s,3H);2.85(m,1H);2.41(s,3H);0.71(m,2H);0.58(m,2H);

[0511] Embodiment No. 1-90: 1 H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s, 1H); 8.76 (t, 1H); 7.82 (br s,1H);6.91(t,1H);4.05(s,3H);3.18(m,2H);2.44(s,3H);1.06(m,1H);0.46(m,2H);0.26(m,2H);

[0512] Embodiment No. 1-92: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.14 (t, 1H); 7.85 (br s, 2H); 6.92 (t, 1H); 6.18 (tt, 1H); 4.05 (s, 3H); 3.73 (m, 2H); 2.42 (s, 3H);

[0513] Embodiment No. 1-123: 1 H-NMR (400MHz, DMSO-d6): δ = 12.03 (br s, 1H); 8.72 (q, 1); 8.07 (d, 1H); 8.02 (d, 1H); 4.01 (s, 3H); 3.31 (s, 3H); 2.79 (d, 3H);

[0514] Embodiment No. 1-125: 1H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s,1H);8.85(d,1H);8.06(d,1H);8.02(d,1H);4.01(s,3H);3.31(s,3H);2.78(m,1H);0.70(m,2H);0.60(m,1H);0.56(m,1H);

[0515] Embodiment No. 1-129: 1 H-NMR (400MHz, DMSO-d6): δ = 12.00 (br s, 1H); 8.69 (q, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

[0516] Embodiment No. 1-130: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 8.76 (t, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.01 (s, 3H); 3.29 (m, 2H); 1.11 (t, 3H);

[0517] Embodiment No. 1-131: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 8.82 (d, 1H); 7.97 (d, 1H); 7.92 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.50 (br s, 2H);

[0518] Embodiment No. 1-132: 1 H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s,1H);8.89(t,1H);7.98(d,1H);7.93(d,1H);4.02(s,3H);3.15(m,2H);1.00(m,1H);0.45(m,2H);0.24(m,2H)

[0519] Embodiment No. 1-133: 1 H-NMR (400MHz, DMSO-d6): δ = 12.06 (br s, 1H); 9.56 (t, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.16 (m, 2H); 4.02 (s, 3H);

[0520] Embodiment No. 1-134: 1H-NMR (400MHz, DMSO-d6): δ = 12.05 (br s, 1H); 9.29 (t, 1H); 8.02 (d, 1H); 7.96 (d, 1H); 6.12 (tt, 1H); 4.02 (s, 3H); 3.72 (m, 2H);

[0521] Embodiment No. 1-135: 1 H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s,1H);8.77(d,1H);7.97(d,1H);7.93(d,1H);4.02(s,3H);3.44(m,1H);1.20(m,3H);0.90(m,1H);0.43(m,2H);0.29(m,2H);

[0522] Embodiment No. 1-136: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.78 (t, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.02 (s, 3H); 3.22 (m, 2H); 1.53 (m, 2H); 0.92 (t, 3H);

[0523] Embodiment No. 1-137: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.66 (d, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.07 (m, 1H); 4.01 (s, 3H); 1.14 (br s, 6H);

[0524] Embodiment No. 1-138: 1 H-NMR (400MHz, DMSO-d6): δ = 12.00 (br s, 1H); 8.91 (t, 1H); 7.97 (d, 1H); 7.92 (d, 1); 4.01 (s, 3H); 3.43 (m, 4H); 3.27 (s, 3H);

[0525] Embodiment No. 1-139: 1 H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s, 1H); 8.99 (t, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 4.01 (s, 3H); 3.45 (m, 2H); 2.63 (t, 2H); 2.11 (s, 3H);

[0526] Embodiment No. 1-140: 1H-NMR (400MHz, DMSO-d6): δ = 12.05 (br s, 1H); 9.61 (t, 1H); 8.04 (d, 1H); 7.99 (d, 1H); 4.42 (d, 2H); 4.01 (s, 3H);

[0527] Embodiment No. 1-141: 1 H-NMR (400MHz, DMSO-d6): δ = 12.00 (br s,1H);8.90(t,1H);7.97(d,1H);7.92(d,1H);4.01(s,3H);3.95(m,1H);3. 77(m,1H);3.63(m,1H);3.30(m,2H);1.95(m,1H);1.83(m,2H);1.63(m,1H);

[0528] Embodiment No. 1-142: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 8.90 (t, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.18 (br d, 2H); 4.01 (s, 3H); 3.00 (s, 3H); 2.86 (s, 3H);

[0529] Embodiment No. 1-143: 1 H-NMR (400MHz, DMSO-d6): δ = 12.08 (br s, 1H); 10.86 (br s, 1H); 8.04 (m, 2H); 7.65 (d, 2H); 7.38 (m, 2H); 7.15 (t, 1H); 4.02 (s, 3H);

[0530] Embodiment No. 1-144: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 9.36 (t, 1H); 7.98 (d, 1H); 7.94 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.98 (m, 1H); 4.66 (br s,2H);4.01(s,3H);

[0531] Embodiment No. 1-146: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s,1H);9.01(d,1H);7.97(d,1H);7.93(d,1H);4.35(m,1H);4.01(s,3H);2.25(m,2H);1.98(m,2H);1.70(m,2H);

[0532] Embodiment No. 1-147: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 8.72 (q, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.01 (s, 3H); 2.81 (d, 3H);

[0533] Embodiment No. 1-148: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 8.78 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.95 (t, 1H); 4.01 (s, 3H); 3.31 (m, 2H); 1.13 (t, 3H);

[0534] Embodiment No. 1-149: 1 H-NMR (400MHz, DMSO-d6): δ = 11.92 (br s,1H);8.85(d,1H);7.90(d,1H);7.77(d,1H);6.95(t,1H);4.00(s,3H);2.83(m,1H);0.72(m,2H);0.55(m,2H);

[0535] Embodiment No. 1-155: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s, 1H); 8.70 (d, 1H); 7.90 (d, 1H); 7.77 (d, 1H); 6.94 (t, 1H); 4.09 (m, 1H); 4.01 (s, 3H); 1.16 (d, 6H);

[0536] Embodiment No. 1-156: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s, 1H); 8.92 (t, 1H); 7.91 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.01 (s, 3H); 3.46 (m, 4H); 3.29 (s, 3H);

[0537] Embodiment No. 1-157: 1 H-NMR (400MHz, DMSO-d6): δ = 11.95 (br s,1H);8.99(t,1H);7.92(d,1H);7.80(d,1H);7.05(t,1H);4.01(s,3H);3.49(m,2H);2.67(m,2H);2.12(s,3H);

[0538] Embodiment No. 1-158: 1 H-NMR (400MHz, DMSO-d6): δ = 11.98 (br s, 1H); 9.59 (t, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.40 (d, 2H); 4.01 (s, 3H);

[0539] Embodiment No. 1-159: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s,1H);8.94(t,1H);7.91(d,1H);7.78(d,1H);6.97(t,1H);4.01(s,3H);3.98(m,1 H);3.78(m,1H);3.64(m,1H);3.35(m,2H);1.95(m,1H);1.84(m,2H);1.62(m,1H);

[0540] Embodiment No. 1-160: 1 H-NMR (400MHz, DMSO-d6): δ = 11.95 (br s,1H);9.12(t,1H);7.94(d,1H);7.83(d,1H);7.58(t,1H);4.17(d,2H);4.01(t,3H);3.02(s,3H);2.89(s,3H);

[0541] Embodiment No. 1-161: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 10.84 (br s,1H);7.99(d,1H);7.85(d,1H);7.69(m,2H);7.38(m,2H);7.15(m,1H);7.12(t,1H);4.02(s,3H);

[0542] Embodiment No. 1-162: 1 H-NMR (400MHz, DMSO-d6): δ = 11.95 (br s,1H);9.45(t,1H);7.93(d,1H);7.79(d,1H);7.45(m,1H);7.08(m,1H);6.99(m,1H);6.92(t,1H);4.68(d,2H);4.00(s,3H);

[0543] Embodiment No. 1-164: 1H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s,1H);9.05(d,1H);7.91(d,1H);7.78(d,1H);6.93(t,1H);4.37(m,1H);4.01(s,3H);2.26(m,2H);2.01(m,2H);1.72(m,2H);

[0544] Embodiment No. 1-165: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.61 (q, 1H); 8.00 (d, 1H); 7.85 (d, 1H); 4.01 (s, 3H); 2.78 (d, 3H);

[0545] Embodiment No. 1-166: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.67 (t, 1H); 7.99 (d, 1H); 7.85 (d, 1H); 4.01 (s, 3H); 3.29 (m, 1H); 1.11 (t, 3H);

[0546] Embodiment No. 1-173: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 8.79 (d, 1H); 7.77 (d, 1H); 7.66 (d, 1H); 3.99 (s, 3H); 2.82 (m, 1H); 0.72 (m, 2H); 0.52 (m, 2H);

[0547] Embodiment No. 1-177: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.65 (q, 1H); 7.81 (d, 1H); 7.69 (d, 1H); 3.99 (s, 3H); 2.79 (d, 3H);

[0548] Embodiment No. 1-178: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.71 (t, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.28 (m, 2H); 1.14 (t, 3H);

[0549] Embodiment No. 1-179: 1H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.77 (d, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 2.81 (m, 1H); 0.72 (m, 2H); 0.54 (d, 2H);

[0550] Embodiment No. 1-180: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s,1H);8.80(t,1H);7.81(d,1H);7.68(d,1H);3.99(s,3H);3.16(m,2H);1.02(m,1H);0.46(m,2H);0.26(m,2H);

[0551] Embodiment No. 1-181: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 9.49 (t, 1H); 7.85 (d, 1H); 7.74 (d, 1H); 4.14 (m, 2H); 3.99 (s, 3H);

[0552] Embodiment No. 1-182: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 9.23 (t, 1H); 7.83 (d, 1H); 7.72 (d, 1H); 6.14 (tt, 1H); 3.99 (s, 3H); 3.70 (m, 2H);

[0553] Embodiment No. 1-183: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s,1H);8.66(d,1H);7.80(d,1H);7.67(d,1H);3.99(s,3H);3.49(m,1H);1.22(d,3H);0.92(m,1H);0.43(m,2H);0.32(m,2H);

[0554] Embodiment No. 1-184: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.72 (t, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.21 (m, 2H); 1.55 (m, 2H); 0.94 (t, 3H);

[0555] Embodiment No. 1-185: 1H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.61 (d, 1H); 7.80 (d, 1H); 7.67 (d, 1H); 4.05 (m, 1H); 3.99 (s, 3H); 1.17 (d, 6H);

[0556] Embodiment No. 1-186: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.86 (t, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 3.99 (s, 3H); 3.47 (m, 2H); 3.41 (m, 2H); 3.28 (s, 3H);

[0557] Embodiment No. 1-187: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.93 (t, 1H); 7.81 (d, 1H); 7.69 (d, 1H); 3.99 (s, 3H); 3.44 (m, 2H); 2.66 (m, 2H); 2.12 (s, 3H);

[0558] Embodiment No. 1-195: 1 H-NMR (400MHz, DMSO-d6): δ = 11.86 (br s, 1H); 8.58 (q, 1H); 7.98 (d, 1H); 7.47 (d, 1H); 3.98 (s, 3H); 2.79 (d, 3H);

[0559] Embodiment No. 1-196: 1 H-NMR (400MHz, DMSO-d6): δ = 11.85 (br s, 1H); 8.64 (t, 1H); 7.98 (d, 1H); 7.47 (d, 1H); 3.99 (s, 3H); 3.27 (m, 2H); 1.15 (t, 3H);

[0560] Embodiment No. 1-197: 1 H-NMR (400MHz, DMSO-d6): δ = 11.86 (br s, 1H); 8.70 (d, 1H); 7.97 (d, 1H); 7.46 (d, 1H); 3.98 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.57 (br s, 2H);

[0561] Embodiment No. 1-207: 1H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 8.67 (q, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.03 (s, 3H); 2.79 (d, 3H);

[0562] Embodiment No. 1-208: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s, 1H); 8.72 (t, 1H); 7.91 (d, 1H); 7.96 (d, 1H); 4.03 (s, 3H); 3.29 (m, 2H); 1.12 (t, 3H);

[0563] Embodiment No. 1-209: 1 H-NMR (400MHz, DMSO-d6): δ = 12.00 (br s,1H);8.81(d,1H);7.96(d,1H);7.91(d,1H);4.03(s,3H);2.79(m,1H);0.72(m,2H);0.57(m,1H);0.48(m,1H);

[0564] Embodiment No. 1-210: 1 H-NMR (400MHz, DMSO-d6): δ = 11.99 (br s,1H);8.84(t,1H);7.96(d,1H);7.91(d,1H);4.03(s,3H);3.14(m,2H);1.01(m,1H);0.45(m,2H);0.24(m,2H);

[0565] Embodiment No. 1-211: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 9.52 (t, 1H); 8.01 (d, 1H); 7.97 (d, 1H); 4.20 (m, 1H); 4.08 (m, 1H); 4.04 (s, 3H);

[0566] Embodiment No. 1-212: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 9.26 (t, 1H); 7.99 (d, 1H); 7.95 (d, 1H); 6.12 (tt, 1H); 4.03 (s, 3H); 3.70 (m, 2H);

[0567] Embodiment No. 1-225: 1H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.70 (q, 1H); 7.86 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.03 (s, 3H); 2.81 (d, 3H);

[0568] Embodiment No. 1-226: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.77 (t, 1H); 7.86 (d, 1H); 7.81 (d, 1H); 6.93 (t, 1H); 4.03 (s, 3H); 3.29 (m, 2H); 1.14 (t, 3H);

[0569] Embodiment No. 1-227: 1 H-NMR (400MHz, DMSO-d6): δ = 11.92 (br s,1H);8.83(d,1H);7.85(d,1H);7.80(d,1H);6.93(t,1H);4.02(s,3H);2.83(m,1H);0.71(m,2H);0.57(m,2H);

[0570] Embodiment No. 1-228: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s,1H);8.90(t,1H);7.86(d,1H);7.81(d,1H);6.93(t,1H);4.03(s,3H);3.16(m,2H);1.04(m,1H);0.46(m,2H);0.26(m,2H);

[0571] Embodiment No. 1-229: 1 H-NMR (400MHz, DMSO-d6): δ = 11.96 (br s, 1H); 9.54 (t, 1H); 7.91 (d, 1H); 7.84 (d, 1H); 6.92 (t, 1H); 4.14 (m, 2H); 4.03 (s, 3H);

[0572] Embodiment No. 1-230: 1 H-NMR (400MHz, DMSO-d6): δ = 11.95 (br s, 1H); 9.28 (t, 1H); 7.90 (d, 1H); 7.83 (d, 1H); 6.94 (t, 1H); 6.18 (tt, 1H); 4.03 (s, 3H); 3.72 (m, 2H);

[0573] Embodiment No. 1-271:1 H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s, 1H); 8.52 (q, 1H); 7.85 (d, 1H); 7.78 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H); 2.72 (m, 2H); 1.17 (t, 3H);

[0574] Embodiment No. 1-272: 1 H-NMR (400MHz, DMSO-d6): δ = 11.80 (br s,1H);8.62(t,1H);7.84(d,1H);7.77(d,1H);4.01(s,3H);3.29(q,2H);2.77(m,2H);1.18(t,3H);1.11(t,3H);

[0575] Embodiment No. 1-273: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s,1H);8.68(d,1H);7.84(d,1H);7.76(d,1H);4.01(s,3H);2.81(m,2H)M2.70(m,1H);1.17(t,3H);0.71(m,2H);0.49(m,2H);

[0576] Embodiment No. 1-274: 1 H-NMR (400MHz, DMSO-d6): δ = 11.80 (br s,1H);8.74(t,1H);7.84(d,1H);7.76(d,1H);4.01(s,3H);3.19(m,1H);3. 08(m,1H); 2.80(m,2H); 1.20(t,3H); 1.02(m,1H); 0.45(m,2H); 0.24(m,2H);

[0577] Embodiment No. 1-276: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);9.10(t,1H);7.88(d,1H);7.79(d,1H);6.13(tt,1H);4.01(s,3H);3.77(m,1H);3.63(m,1H);2.77(m,2H);1.17(t,3H);

[0578] Embodiment No. 1-277: 1H-NMR (400MHz, DMSO-d6): δ = 11.73 (br s,1H);8.57(q,3H);7.80(d,1H);7.64(d,1H);6.89(t,1H);4.00(s,3H);2.81(d,3H);2.74(q,2H);1.15(t,3H);

[0579] Embodiment No. 1-278: 1 H-NMR (400MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.67 (t, 1H); 7.80 (d, 1H); 7.64 (d, 1H); 6.90 (t, 1H); 4.00 (s, 3H); 3.21 (m, 2H); 2.76 (q, 2H); 1.15 (2x t,6H)

[0580] Embodiment No. 1-279: 1 H-NMR (400MHz, DMSO-d6): δ = 11.72 (br s,1H);8.75(d,1H);7.80(d,1H);7.63(d,1H);6.89(t,1H);4.00(s,3H);2.86(m,1H);2,75(m,2H);1.15(t,3H);0.71(m,2H);0.53(m,2H);

[0581] Embodiment No. 1-286: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 8.44 (q, 1H); 7.77 (br s, 2H); 4.03 (s, 3H); 2.79 (d, 3H); 2.11 (m, 1H); 0.84 (m, 2H); 0.64 (m, 2H);

[0582] Embodiment No. 1-287: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 8.51 (t, 1H); 7.77 (br s,2H);4.03(s,3H);3.29(m,2H);2.14(m,1H);1.13(t,3H);0.84(m,2H);0.66(m,2H);

[0583] Embodiment No. 1-288: 1H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 8.59 (d, 1H); 7.77 (br s,2H);4.03(s,3H);2.79(m,1H);2.11(m,1H);0.85(m,2H);0.70(m,2H);0.66(m,2H);0.51(m,2H);

[0584] Example No. 1-289: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 8.63 (t, 1H); 7.77 (br s,2H);4.03(s,3H);3.13(m,2H);2.15(m,1H);1.03(m,1H);0.85(m,2H);0.68(m,2H);0.45(m,2H);0.23(m,2H);

[0585] Embodiment No. 1-291: 1 H-NMR (400MHz, DMSO-d6): δ = 11.72 (br s, 1H); 9.03 (t, 1H); 7.80 (br s,2H);6.13(tt,1H);4.04(s,3H);3.69(m,2H);2.13(m,1H);0.87(m,2H);0.64(m,2H);

[0586] Embodiment No. 1-292: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s, 1H); 8.55 (d, 1H); 7.76 (br s,2H);4.03(s,3H);3.38(m,1H);2.18(m,1H);1.21(d,3H);0.89(m,3H);0.69(m,2H);0.44(m,2H);0.34(m,1H);0.24(m,1H);

[0587] Embodiment No. 1-304: 1 H-NMR (400MHz, DMSO-d6): δ = 11.64 (br s,1H);8.52(q,1H);7.73(d,1H);7.66(d,1H);6.94(t,1H);4.03(s,3H);2.81(d,3H);2.17(m,1H);0.83(m,2H);0.58(m,2H);

[0588] Embodiment No. 1-305: 1H-NMR (400MHz, DMSO-d6): δ = 11.62 (br s,1H);8.60(t,1H);7.72(d,1H);7.66(d,1H);6.94(t,1H);4.03(s,3H);3.31(m,2H);2.19(m,1H);1.14(t,3H);0.83(m,2H);0.60(m,2H);

[0589] Embodiment No. 1-306: 1 H-NMR (400MHz, DMSO-d6): δ = 11.61 (br s,1H);8.67(d,1H);7.72(d,1H);7.65(d,1H);6.94(t,1H);4.03(s,3H);2.84(m,1H);2.16(m,1H);0.83(m,2H);0.70(m,2H);0.57(m,4H);

[0590] Embodiment No. 1-337: 1 H-NMR (400MHz, DMSO-d6): δ = 12.03 (br s, 1H); 7.98 (br s, 2H); 4.02 (s, 3H); 3.91 (br s, 1H); 2.07 (br s, 3H);

[0591] Embodiment No. 1-338: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.22 (s, 1H); 8.00 (s, 1H); 7.97 (d, 1H); 7.94 (d, 1H); 4.03 (s, 3H);

[0592] Embodiment No. 1-339: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.70(d,1H);7.79(d,1H);7.64(d,1H);6.90(t,1H);4.00(s,3H);3.45(m,1 H);2.38(s,3H);1.22(d,3H);0.93(m,1H);0.46(m,2H);0.35(m,1H);0.28(m,1H);

[0593] Embodiment No. 1-340: 1H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s,1H);8.79(d,1H);7.85(d,1H);7.81(d,1H);6.91(t,1H);4.03(s,3H);3. 45(m,1H);1.23(d,3H);0.92(m,1H);0.44(m,2H);0.38(m,1H);0.29(m,1H);

[0594] Embodiment No. 1-341: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s,1H);8.66(d,1H);7.83(d,1H);7.76(d,1H);4.01(s,3H);3.40(m,1H);2.84(q,2 H);2.78(m,1H);1.22(t,3H);1.17(t,3H);0.91(m,1H);0.43(m,2H);0.29(m,2H);

[0595] Embodiment No. 1-342: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.62 (q, 1H); 7.84 (d, 1H); 7.64 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

[0596] Embodiment No. 1-343: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.68 (t, 1H); 7.83 (d, 1H); 7.63 (d, 1H); 4.01 (s, 3H); 3.28 (q, 2H); 1.14 (t, 3H);

[0597] Embodiment No. 1-344: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 8.74 (d, 1H); 7.82 (d, 1H); 7.63 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.56 (m, 2H);

[0598] Embodiment No. 1-345: 1H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.67(t,1H);7.79(d,1H);7.64(d,1H);6.90(t,1H);4.00(s,3H);3.24(m,2H);2.36(s,3H);1.54(m,2H);0.91(t,3H);

[0599] Embodiment No. 1-346: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.57(d,1H);7.79(d,1H);7.63(d,1H);6.91(t,1H);4.11(m,1H);4.00(s,3H);2.36(s,3H);1.16(d,6H);

[0600] Embodiment No. 1-347: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.74(t,1H);7.79(d,1H);7.62(d,1H);6.93(t,1H);4.00(s,3H);3.47(m,4H);3.28(s,3H);2.36(s,3H);

[0601] Embodiment No. 1-348: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.81(t,1H);7.80(d,1H);7.65(d,1H);7.01(t,1H);4.00(s,3H);3.49(m,2H);2.68(m,2H);2.38(s,3H);2.11(s,3H);

[0602] Embodiment No. 1-349: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.65 (q, 1H); 7.73 (d, 1H); 7.70 (d, 1H); 4.01 (s, 3H); 2.79 (d, 3H);

[0603] Embodiment No. 1-350: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.71 (t, 1H); 7.73 (d, 1H); 7.69 (d, 1H); 4.01 (s, 3H); 3.28 (m, 2H); 1.14 (t, 3H);

[0604] Embodiment No. 1-351: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 8.77 (d, 1H); 7.72 (d, 1H); 7.68 (d, 1H); 4.01 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.55 (m, 2H);

[0605] Embodiment No. 1-352: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.56(d,1H);7.94(d,1H);7.86(d,1H);4.06(s,3H);3.47(m,1H);2.45(s,3H);1.21(d,3H);0.91(m,1H);0.41(m,2H);0.33(m,2H);

[0606] Embodiment No. 1-353: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s, 1H); 8.65 (d, 1H); 7.82 (br s,2H);6.88(t,1H);4.05(s,3H);3.51(m,1H);2.44(s,3H);1.23(d,3H);0.93(m,1H);0.41(m,3H);0.30(m,1H);

[0607] Embodiment No. 1-354: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.35 (q, 1H); 7.74 (d, 1H); 7.19 (d, 1H); 3.97 (s, 3H); 3.85 (s, 3H); 2.74 (d, 3H);

[0608] Embodiment No. 1-355: 1 H-NMR (400MHz, DMSO-d6): δ = 11.64 (br s, 1H); 8.41 (t, 1H); 7.74 (d, 1H); 7.18 (d, 1H); 3.97 (s, 3H); 3.85 (s, 3H); 3.24 (m, 2H); 1.10 (t, 3H);

[0609] Embodiment No. 1-356: 1H-NMR (400MHz, DMSO-d6): δ = 11.64 (br s,1H);8.48(d,1H);7.73(d,1H);7.18(d,1H);3.97(s,3H);3.85(s,3H);2.79(m,1H);0.68(m,2H);0.49(m,2H);

[0610] Embodiment No. 1-357: 1 H-NMR (400MHz, DMSO-d6): δ = 12.05 (br s, 1H); 11.93 (br s, 1H); 8.06 (d, 1H); 7.99 (d, 1H); 4.02 (s, 3H); 3.74 (s, 3H);

[0611] Embodiment No. 1-358: 1 H-NMR (400MHz, DMSO-d6): δ = 12.04 (br s, 1); 11.81 (br s, 1H); 8.05 (d, 1H); 7.99 (d, 1H); 4.02 (s, 3H); 3.97 (m, 2H); 1.23 (t, 3H);

[0612] Example No. 1-359: 1 H-NMR (400MHz, DMSO-d6): δ = 12.04 (br s, 1H); 11.81 (br s, 1H); 8.05 (d, 1H); 7.98 (d, 1H); 4.02 (s, 3H); 3.88 (m, 2H); 1.64 (m, 2H); 0.94 (t, 3H);

[0613] Embodiment No. 1-360: 1 H-NMR (400MHz, DMSO-d6): δ = 12.04 (br s, 1H); 11.65 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.18 (m, 1H); 4.02 (s, 3H); 1.22 (d, 6H);

[0614] Embodiment No. 1-361: 1 H-NMR (400MHz, DMSO-d6): δ = 11.98 (br s, 1H); 11.92 (br s, 1H); 7.98 (d, 1H); 7.81 (d, 1H); 7.04 (t, 1H); 4.01 (s, 3H); 3.76 (s, 3H);

[0615] Embodiment No. 1-362: 1H-NMR (400MHz, DMSO-d6): δ = 11.98 (br s, 1H); 11.81 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.02 (t, 1H); 4.01 (s, 3H); 3.99 (q, 2H); 1.23 (t, 3H);

[0616] Embodiment No. 1-363: 1 H-NMR (400MHz, DMSO-d6): δ = 11.97 (br s, 1H); 11.81 (br s,1H);7.97(d,1H);7.81(d,1H);7.02(t,1H);4.01(s,3H);3.90(t,2H);1.64(m,2H);0.94(t,3H);

[0617] Embodiment No. 1-364: 1 H-NMR (400MHz, DMSO-d6): δ = 11.97 (br s, 1H); 11.67 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.21 (m, 1H); 4.01 (s, 3H); 1.23 (d, 6H);

[0618] Example No. 2-19: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);8.57(q,1H);7.94(d,1H);7.88(d,1H);4.36(q,2H);3.27(s,3H);2.78(d,3H);2.35(s,3H);1.47(t,3H);

[0619] Embodiment No. 2-20: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);8.63(t,1H);7.94(d,1H);7.87(d,1H);4.35(q,2H);3.27(m,2H);3.27(s,3H);2.37(s,3H);1.47(t,3H);1.13(t,3H);

[0620] Embodiment No. 2-21: 1H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.70(d,1H);7.93(d,1H);7.87(d,1H);4.35(q,2H);3.27(s,3H);2. 77(m,1H);2.35(s,3H);1.47(t,3H);0.69(m,2H);0.62(m,1H);0.51(m,1H);

[0621] Embodiment No. 2-25: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.51 (q, 1H) 7.82 (d, 1H); 7.76 (d, 1H); 4.35 (q, 2H); 2.79 (d, 3H); 2.33 (s, 3H); 1.47 (t, 3H);

[0622] Embodiment No. 2-26: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s,1H);8.60(t,1H);7.83(d,1H);7.76(d,1H);4.35(q,2H);3.30(m,2H);2.35(s,3H);1.47(t,3H);1.11(t,3H);

[0623] Embodiment No. 2-27: 1 H-NMR (400MHz, DMSO-d6): δ = 11.64 (br s,1H);8.66(d,1H);7.82(d,1H);7.75(d,1H);4.35(q,2H);2.81(m,1H);2.34(s,3H);1.47(t,3H);0.71(m,2H);0.49(m,2H);

[0624] Embodiment No. 2-28: 1 H-NMR (400MHz, DMSO-d6): δ = 11.68 (br s,1H);8.72(t,1H);7.82(d,1H);7.76(d,1H);4.35(q,2H);3.13(m,2H);2.38(s,3H);1.47(t,3H);1.01(m,1H);0.45(m,2H);0.23(m,2H);

[0625] Embodiment No. 2-29: 1H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 9.38 (t, 1H); 7.87 (d, 1H); 7.80 (d, 1H); 4.35 (q, 2H); 4.13 (m, 2H); 2.35 (s, 3H); 1.47 (t, 3H);

[0626] Embodiment No. 2-30: 1 H-NMR (400MHz, DMSO-d6): δ = 11.68 (br s,1H);9.08(t,1H);7.85(d,1H);7.78(d,1H);6.14(tt,1H);4.35(q,2H);3.70(m,2H);2.36(s,3H);1.47(t,3H);

[0627] Embodiment No. 2-31: 1 H-NMR (400MHz, DMSO-d6): δ = 11.66 (br s,1H);0.62(t,1H);7.81(d,1H);7.75(d,1H);4.35(q,2H);3.40(m,1H);2.3 9(d,3H);1.48(t,3H);1.20(dd,3H);0.90(m,1H);0.45(m,2H);0.30(m,2H);

[0628] Embodiment No. 2-32: 1 H-NMR (400MHz, DMSO-d6): δ = 11.67 (br s,1H);8.62(t,1H);7.82(d,1H);7.76(d,1H);4.35(q,2H);3.21(m,2H);2.36(s,3H);1.51(m,2H);1.47(t,3H);0.91(t,3H);

[0629] Embodiment No. 2-33: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s,1H);8.50(d,1H);7.81(d,1H);7.75(d,1H);4.35(q,2H);4.09(m,1H);2.36(s,3H);1.47(t,3H);1.16(d,3H);1.12(d,3H);

[0630] Embodiment No. 2-34: 1H-NMR (400MHz, DMSO-d6): δ = 11.66 (br s, 1H); 8.70 (d, 1H); 4.35 (q, 2H); 3.52-3.30 (m, 4H); 3.27 (s, 3H); 2.36 (s, 3H); 1.47 (t, 3H);

[0631] Embodiment No. 2-35: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.78(t,1H);7.83(d,1H);7.76(d,1H);4.35(q,2H);3.50(m,1H);3.40(m,1H);2.64(m,2H);2.39(s,3H);2.11(s,3H);1.47(t,3H);

[0632] Embodiment No. 2-36: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s, 1H); 9.42 (t, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 4.49 (m, 2H); 4.36 (q, 2H); 2.35 (s, 3H); 1.47 (t, 3H);

[0633] Embodiment No. 2-37: 1 H-NMR (400MHz, DMSO-d6): δ = 11.67 (br s, 1H); 8.72 (br s,1H);7.82(d,1H);7.75(d,1H);4.37(q,2H);3.96(m,1H);3.77(m,1H);3.62(m,1H);3. 37(m,1H); 3.27(m,1H); 2.36(s,3H); 1.94(m,1H); 1.82(m,2H); 1.60(m,1H); 1.47(t,3H);

[0634] Embodiment No. 2-42: 1 H-NMR (400MHz, DMSO-d6): δ = 11.66 (br s, 1H); 8.85 (d, 1H); 7.82 (d, 1H); 7.76 (d, 1H); 4.37 (m, 1H); 4.35 (q, 2H); 2.34 (s, 3H); 2.24 (m 2H);1.97(m,2H);1.69(m,2H);1.47(t,3H);

[0635] Embodiment No. 2-44: 1H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s,1H);8.56(q,1H);7.79(d,1H);7.64(d,1H);6.91(t,1H);4.34(q,2H);2.81(d,3H);2.33(s,3H);1.47(t,3H);

[0636] Embodiment No. 2-45: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s,1H);8.65(t,1H);7.78(d,1H);7.64(d,1H);6.91(t,1H);4.34(q,2H);3.31(m,2H);2.35(s,3H);1.47(t,3H);1.13(t,3H);

[0637] Embodiment No. 2-46: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s,1H);8.71(d,1H);7.78(d,1H);7.63(d,1H);6.91(t,1H);4.34(q,2H);2.85(m,1H);2.33(s,3H);1.47(t,3H);0.71(m,2H);0.53(m,2H);

[0638] Embodiment No. 2-47: 1 H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s,1H);8.79(t,1H);7.79(d,1H);7.64(d,1H);6.92(t,1H);4.35(q,2H);3. 16(m,2H);2.38(s,3H);1.47(t,3H);1.05(m,1H);0.46(m,2H);0.24(m,2H);

[0639] Embodiment No. 2-49: 1 H-NMR (400MHz, DMSO-d6): δ = 11.60 (br s,1H);9.12(t,1H);7.82(d,1H);7.66(d,1H);6.93(t,1H);6.19(tt,1H);4.35(q,2H);3.72(m,2H);2.36(s,3H);1.47(t,3H);

[0640] Embodiment No. 2-56: 1H-NMR (400MHz, DMSO-d6): δ = 11.56 (br s, 1H); 8.53 (q, 1H); 7.88 (d, 1H); 7.67 (d, 1H); 4.34 (q, 2H); 3.86 (s, 3H); 2.79 (d, 3H); 1.47 (t, 3H);

[0641] Embodiment No. 2-57: 1 H-NMR (400MHz, DMSO-d6): δ = 11.54 (br s,1H);8.61(t,1H);7.88(d,1H);7.67(d,1H);4.34(q,2H);3.88(s,3H);3.28(m,2H);1.47(t,3H);1.11(t,3H);

[0642] Embodiment No. 2-58: 1 H-NMR (400MHz, DMSO-d6): δ = 11.54 (br s,1H);8.68(d,1H);7.87(d,1H);7.66(d,1H);4.34(q,2H);3.87(s,3H);2.80(m,1H);1.47(t,3H);0.71(m,2H);0.49(m,2H);

[0643] Embodiment No. 2-72: 1 H-NMR (400MHz, DMSO-d6): δ = 11.42 (br s,1H);8.58(q,1H);7.84(d,1H);7.54(d,1H);6.96(t,1H);4.34(q,2H);3.85(s,3H);2.81(d,3H);1.47(t,3H);

[0644] Embodiment No. 2-73: 1 H-NMR (400MHz, DMSO-d6): δ = 11.42 (br s,1H);8.65(t,1H);7.84(d,1H);7.54(d,1H);6.96(t,1H);4.34(q,2H);3.86(s,3H);3.30(m,2H);1.47(t,3H);1.13(t,3H);

[0645] Embodiment No. 2-74: 1H-NMR (400MHz, DMSO-d6): δ = 11.40 (br s,1H);8.72(d,1H);7.83(d,1H);7.53(d,1H);6.95(t,1H);4.33(q,2H);3.85(s,3H);2.85(m,1H);1.47(t,3H);0.72(m,2H);0.55(m,2H);

[0646] Embodiment No. 2-81: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s, 1H); 8.48 (q, 1H); 7.95 (d, 1H); 7.86 (d, 1H); 4.43 (q, 2H); 2.80 (d, 3H); 2.43 (s, 3H); 1.48 (t, 3H);

[0647] Embodiment No. 2-82: 1 H-NMR (400MHz, DMSO-d6): δ = 11.70 (br s,1H);8.56(t,1H);7.94(d,1H);7.86(d,1H);4.43(q,2H);3.30(m,2H);2.44(s,3H);1.48(t,3H);1.13(s,3H);

[0648] Embodiment No. 2-83: 1 H-NMR (400MHz, DMSO-d6): δ = 11.72 (br s,1H);8.64(d,1H);7.94(d,1H);7.86(d,1H);4.43(q,2H);2.80(m,1H);2.43(s,3H);1.48(t,3H);0.71(m,2H);0.53(br s,2H);

[0649] Embodiment No. 2-84: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);8.68(t,1H);7.95(d,1H);7.86(d,1H);4.44(q,2H);3.16(m,2H);2.45(s,3H);1.47(t,3H);1.02(m,1H);0.45(m,2H);0.25(m,2H);

[0650] Embodiment No. 2-86: 1H-NMR (400MHz, DMSO-d6): δ = 11.73 (br s,1H);9.10(t,1H);7.98(d,1H);7.91(d,1H);6.12(tt,1H);4.43(q,2H);3.71(m,2H);2.43(s,3H);1.49(t,3H);

[0651] Embodiment No. 2-87: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.55 (q, 1H); 7.81 (s, 2H); 6.91 (t, 1H); 4.43 (q, 2H); 2.83 (d, 3H); 2.42 (s.3H); 1.49 (t, 3H);

[0652] Embodiment No. 2-88: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s,1H);8.62(t,1H);7.81(s,2H);6.90(t,1H);4.43(q,2H);3.32(m,2H);2.43(s,3H);1.48(t,3H);1.15(t,3H);

[0653] Embodiment No. 2-89: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.70 (d, 1H); 7.80 (br s,2H);6.90(t,1H);4.43(q,2H);2.85(m,1H);2.41(s,3H);1.48(t,3H);0.72(m,2H);0.57(m,2H);

[0654] Embodiment No. 2-90: 1 H-NMR (400MHz, DMSO-d6): δ = 11.66 (br s,1H);8.76(t,1H);7.83(m,2H);6.91(t,1H);4.43(q,2H);3.19(m,2H);2.44(s,3H);1.49(t,3H);1.06(m,1H);0.46(m,2H);0.26(m,2H);

[0655] Embodiment No. 2-92: 1H-NMR (400MHz, DMSO-d6): δ = 11.68 (br s, 1H); 9.14 (t, 1H); 7.84 (br s,2H);6.92(t,1H);6.18(tt,1H);4.43(q,2H);3.73(m,2H);2.42(s,3H);1.48(t,3H);

[0656] Embodiment No. 2-123: 1 H-NMR (400MHz, DMSO-d6): δ = 11.92 (br s, 1H); 8.73 (q, 1H); 8.07 (d, 1H); 8.02 (d, 1H); 4.37 (q, 2H); 2.79 (d, 3H); 1.47 (t, 3H);

[0657] Embodiment No. 2-125: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s,1H);8.85(d,1H);8.05(d,1H);8.02(d,1H);4.37(q,2H);3.31(s,3H);2.77(m,1H);1.47(t,3H);0.69(m,2H);0.58(m,2H);

[0658] Embodiment No. 2-129: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.70 (q, 1H); 7.97 (d, 1H); 7.93 (d, 1H); 4.37 (q, 2H); 2.79 (d, 3H); 1.47 (t, 3H);

[0659] Embodiment No. 2-130: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.76 (t, 1H); 7.96 (d, 1H); 7.93 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (t, 3H); 1.12 (t, 3H);

[0660] Embodiment No. 2-131: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.83 (d, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.37 (q, 2H); 2.80 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.50 (br s,2H);

[0661] Embodiment No. 2-132: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s,1H);8.89(t,1H);7.97(d,1H);7.93(d,1H);4.38(q,2H);3.15(m,3H);1.47(t,3H);0.46(m,2H);0.23(m,2H);

[0662] Embodiment No. 2-133: 1 H-NMR (400MHz, DMSO-d6): δ = 11.96 (br s, 1H); 9.56 (t, 1H); 8.03 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 4.15 (m, 2H); 1.47 (t, 3H);

[0663] Embodiment No. 2-134: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 9.29 (t, 1H); 8.01 (d, 1H); 7.96 (d, 1H); 6.12 (tt, 1H); 4.38 (q, 2H); 3.71 (m, 2H); 1.47 (t, 3H);

[0664] Embodiment No. 2-135: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s,1H);8.77(d,1H);7.96(d,1H);7.92(d,1H);4.38(q,2H);3.43(m,1H);1.48(t,3H);1.20(m,3H);0.90(m,1H);0.43(m,2H);0.30(m,2H);

[0665] Embodiment No. 2-138: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.91 (t, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.38 (q, 2H); 3.45 (m, 4H); 3.27 (s, 3H); 1.47 (t, 3H);

[0666] Embodiment No. 2-139: 1H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s,1H);8.99(t,1H);7.98(d,1H);7.93(d,1H);4.38(q,2H);3.45(m,2H);2.63(t,2H);2.11(s,3H);1.47(t,3H);

[0667] Embodiment No. 2-141: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.90 (t, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.37 (q, 2H); 3.96 (m, 1H); 3.78 (m, 1H); 3.65 (m, 1H); 3.32 (br s,2H);1.93(m,1H);1.83(m,2H);1.62(m,1H);1.47(t,3H);

[0668] Embodiment No. 2-142: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.90 (t, 1H); 7.95 (d, 1H); 7.90 (d, 1H); 4.37 (q, 2H); 4.18 (br d,2H);3.00(s,3H);2.86(s,3H);1.47(t,3H);

[0669] Embodiment No. 2-143: 1 H-NMR (400MHz, DMSO-d6): δ = 11.98 (br s, 1H); 10.88 (br s,1H);8.06(d,1H);8.02(d,1H);7.65(d,2H);7.38(t,2H);7.16(t,1H);4.38(q,2H);1.47(t,3H);

[0670] Embodiment No. 2-144: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 9.37 (t, 1H); 7.98 (d, 1H); 7.93 (d, 1H); 7.45 (m, 1H); 7.07 (m, 1H); 6.99 (m, 1H); 4.66 (br s,2H);4.37(q,2H);1.47(t,3H);

[0671] Embodiment No. 2-146: 1H-NMR (400MHz, DMSO-d6): δ = 11.61 (br s,1H);7.74(d,1H);7.71(d,1H);4.62(m,1H);4.57(q,2H);2.46(m,2H);2.19(m,2H);1.82(m,2H);1.62(t,3H);

[0672] Embodiment No. 2-147: 1 H-NMR (400MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.72 (q, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 6.96 (t, 1H); 4.37 (q, 2H); 2.81 (d, 3H); 1.47 (t, 3H);

[0673] Embodiment No. 2-148: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.79(t,1H);7.90(d,1H);7.78(d,1H);6.96(t,1H);4.37(q,2H);3.31(m,2H);1.47(t,3H);1.13(t,3H);

[0674] Embodiment No. 2-149: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.85(d,1H);7.89(d,1H);7.77(d,1H);6.95(t,1H);4.37(q,2H);2.84(m,1H);1.47(t,3H);0.72(m,2H);0.55(m,2H);

[0675] Embodiment No. 2-154: 1 H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s,1H);8.81(t,1H);7.90(d,1H);7.78(d,1H);6.95(t,1H);4.37(q,2H);3.24(m,2H);1.54(m,2H);1.47(t,3H);0.92(t,3H);

[0676] Embodiment No. 2-155: 1H-NMR (400MHz, DMSO-d6): δ = 11.83 (br s,1H);8.70(d,1H);7.89(d,1H);7.77(d,1H);6.95(t,1H);4.37(q,2H);4.09(m,1H);1.47(t,3H);1.16(d,6H);

[0677] Embodiment No. 2-156: 1 H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s,1H);8.93(t,1H);7.90(d,1H);7.78(d,1H);6.93(t,1H);4.37(q,2H);3.47(m,4H);3.29(s,3H);1.47(t,3H);

[0678] Embodiment No. 2-157: 1 H-NMR (400MHz, DMSO-d6): δ = 11.85 (br s,1H);8.99(t,1H);7.92(d,1H);7.80(d,1H);7.05(t,1H);4.37(q,2H);3.49(m,2H);2.67(m,2H);2.12(s,3H);1.47(t,3H);

[0679] Embodiment No. 2-158: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 9.59 (t, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.01 (t, 1H); 4.37 (m, 4H); 1.47 (t, 3H);

[0680] Embodiment No. 2-159: 1 H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s,1H);8.94(t,1H);7.90(d,1H);7.78(d,1H);6.98(t,1H);4.37(q,2H);3.99(m,1H);3. 78(m,1H);3.65(m,1H);3.35(m,2H);1.94(m,1H);1.84(m,2H);1.62(m,1H);1.47(t,3H);

[0681] Embodiment No. 2-160: 1H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s,1H);9.12(t,1H);7.93(d,1H);7.83(d,1H);7.58(t,1H);4.37(q,2H);4.17(d,2H);3.02(s,3H);2.89(s,3H);1.47(t,3H);

[0682] Embodiment No. 2-161: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 10.84 (br s,1H);7.98(d,1H);7.85(d,1H);7.69(m,2H);7.38(m,2H);7.16(m,1H);7.12(t,1H);4.38(q,2H);1.48(t,3H);

[0683] Embodiment No. 2-162: 1 H-NMR (400MHz, DMSO-d6): δ = 11.85 (br s,1H);9.45(t,1H);7.92(d,1H);7.79(d,1H);7.45(m,1H);7.07(m,1H);6.99(m,1H);6.92(t,1H);4.68(d,2H);4.36(q,2H);1.47(t,3H);

[0684] Embodiment No. 2-164: 1 H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s,1H);9.05(d,1H);7.90(d,1H);7.78(d,1H);6.93(t,1H);4.37(m,3H);2.25(m,2H);2.01(m,2H);1.71(m,2H);1.47(t,3H);

[0685] Embodiment No. 2-173: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s,1H);8.79(d,1H);7.76(d,1H);7.66(d,1H);4.35(q,2H);2.82(m,1H);1.47(t,3H);0.73(m,2H);0.53(m,2H);

[0686] Embodiment No. 2-177: 1H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s, 1H); 8.65 (d, 1H); 7.81 (d, 1H); 7.68 (d, 1H); 4.35 (q, 2H); 2.79 (d, 3H); 1.46 (t, 3H);

[0687] Embodiment No. 2-178: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s, 1H); 8.71 (t, 1H); 7.81 (d, 1H); 7.67 (d, 1H); 4.35 (q, 1H); 3.28 (m, 2H); 1.46 (t, 3H); 1.14 (t, 3H);

[0688] Embodiment No. 2-179: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s,1H);8.77(d,1H);7.80(d,1H);7.67(d,1H);4.35(q,2H);2.81(m,1H);1.46(t,3H);0.72(m,2H);0.54(m,2H);

[0689] Embodiment No. 2-180: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s,1H);8.80(t,1H);7.81(d,1H);7.67(d,1H);4.35(q,2H);3.16(m,2H);1.46(t,3H);1.02(m,1H);0.46(m,2H);0.26(m,2H);

[0690] Embodiment No. 2-181: 1 H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.50 (t, 1H); 7.85 (d, 1H); 7.73 (d, 1H); 4.35 (q, 2H); 4.13 (m, 2H); 1.46 (t, 3H);

[0691] Embodiment No. 2-182: 1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.23 (t, 1H); 7.83 (d, 1H); 7.71 (d, 1H); 6.14 (tt, 1H); 4.35 (q, 2H); 3.70 (m, 2H); 1.46 (t, 3H);

[0692] Embodiment No. 2-183:1 H-NMR (400MHz, DMSO-d6): δ = 11.79 (br s,1H);8.67(d,1H);7.80(d,1H);7.66(d,1H);4.35(q,2H);3.49(m,1H);1.47(t,3H);1.22(d,3H);0.92(m,1H);0.43(m,2H);0.32(m,2H);

[0693] Embodiment No. 2-184: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s,1H);8.72(t,1H);7.81(d,1H);7.67(d,1H);4.35(q,2H);3.22(m,2H);1.56(m,2H);1.46(t,3H);0.94(t,3H);

[0694] Embodiment No. 2-185: 1 H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s, 1H); 7.80 (d, 1H); 7.66 (d, 1H); 4.35 (q, 2H); 4.06 (m, 1H); 1.46 (t, 3H); 1.17 (d, 6H);

[0695] Embodiment No. 2-186: 1 H-NMR (400MHz, DMSO-d6): δ = 11.78 (br s,1H);8.86(t,1H);7.80(d,1H);7.67(d,1H);4.35(q,2H);3.48(m,2H);3.41(m,2H);3.28(s,3H);1.46(s,3H);

[0696] Embodiment No. 2-187: 1 H-NMR (400MHz, DMSO-d6): δ = 11.80 (br s,1H);8.93(t,1H);7.81(d,1H);7.69(d,1H);4.35(q,2H);3.44(m,2H);2.67(m,2H);2.09(s,3H);1.46(t,3H);

[0697] Embodiment No. 2-195: 1 H-NMR (400MHz, DMSO-d6): δ = 11.74 (br s, 1H); 8.58 (q, 1H); 7.98 (d, 1H); 7.46 (d, 1H); 4.34 (q, 2H); 2.79 (d, 3H); 1.45 (t, 3H);

[0698] Embodiment No. 2-196: 1 H-NMR (400MHz, DMSO-d6): δ = 11.75 (br s, 1H); 8.64 (t, 1H); 7.98 (d, 1H); 7.46 (d, 1H); 4.34 (q, 2H); 3.27 (m, 2H); 1.46 (t, 3H); 1.15 (t, 3H);

[0699] Embodiment No. 2-197: 1 H-NMR (400MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.70 (d, 1H); 7.97 (d, 1H); 7.45 (d, 1H); 4.34 (q, 2H); 2.79 (m, 1H); 1.45 (t, 3H); 0.72 (m, 2H); 0.57 (br s,2H);

[0700] Embodiment No. 2-207: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.67 (q, 1H); 7.96 (d, 1H); 7.91 (d, 1H); 4.39 (q, 2H); 2.79 (d, 3H); 1.48 (t, 3H);

[0701] Embodiment No. 2-208: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 7.90 (d, 1H); 4.39 (q, 2H); 3.29 (m, 2H); 1.48 (t, 3H); 1.12 (t, 3H);

[0702] Embodiment No. 2-210: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s,1H);8.84(t,1H);7.96(d,1H);7.90(d,1H);4.40(q,2H);3.14(m,2H);1.48(t,3H);1.01(m,1H);0.46(m,2H);0.24(m,2H);

[0703] Embodiment No. 2-211: 1H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s, 1H); 9.52 (t, 1H); 8.00 (d, 1H); 7.96 (d, 1H); 4.40 (q, 2H); 4.19 (m, 1H); 4.08 (m, 1H); 1.48 (t, 3H);

[0704] Embodiment No. 2-212: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 9.26 (t, 1H); 7.99 (d, 2H); 7.94 (d, 1H); 6.12 (tt, 1H); 4.40 (q, 2H); 3.70 (m, 2H); 1.48 (t, 3H);

[0705] Embodiment No. 2-213: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 4.40 (q, 2H); 3.42 (m, 1H); 1.48 (t, 3H); 1.24and 1.18 (2x d,3H);0.90(m,1H);0.33(m,4H);

[0706] Embodiment No. 2-225: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.70 (q, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 6.94 (t, 1H); 4.39 (q, 2H); 2.81 (d, 3H); 1.47 (t, 3H);

[0707] Embodiment No. 2-226: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.77(t,1H);7.85(d,1H);7.81(d,1H);6.93(t,1H);4.39(q,2H);3.30(m,2H);1.48(t,3H);1.14(t,3H);

[0708] Embodiment No. 2-227: 1H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s,1H);8.83(d,1H);7.84(d,1H);7.80(d,1H);6.93(t,1H);4.39(q,2H);2.83(m,1H);1.47(t,3H);0.72(m,2H);0.57(m,2H);

[0709] Embodiment No. 2-228: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s,1H);8.90t,1H);7.85(d,1H);7.81(d,1H);6.93(t,1H);4.39(q,2H);3.16(t,2H);1.48(t,3H);1.04(m,1H);0.48(m,2H);0.25(m,2H);

[0710] Embodiment No. 2-229: 1 H-NMR (400MHz, DMSO-d6): δ = 11.84 (br s, 1H); 9.54 (t, 1H); 7.90 (d, 1H); 7.84 (d, 1H); 6.93 (t, 1H); 4.39 (q, 2H); 4.14 (m, 2H); 1.48 (t, 3H);

[0711] Embodiment No. 2-230: 1 H-NMR (400MHz, DMSO-d6): δ = 11.83 (br s,1H);9.28(t,1H);7.89(d,1H);7.83(d,1H);6.94(t,1H);6.18(tt,1H);4.39(q,2H);3.72(m,2H);1.48(t,3H);

[0712] Embodiment No. 2-271: 1 H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.53(q,1H);7.84(d,1H);7.77(d,1H);4.36(q,2H);2.79(d,3H);2.69(m,2H);1.48(t,3H);1.17(t,3H);

[0713] Embodiment No. 2-272: 1H-NMR (400MHz, DMSO-d6): δ = 11.69 (br s,1H);8.62(t,1H);7.83(d,1H);7.77(d,1H);4.36(q,2H);3.29(m,2H);2.77(m,2H);1.48(t,3H);1.18(t,3H);1.11(t,3H);

[0714] Embodiment No. 2-273: 1 H-NMR (400MHz, DMSO-d6): δ = 11.67 (br s,1H);8.67(d,1H);7.82(d,1H);7.76(d,1H);4.35(q,2H);2.80(m,2H);2.70(m,1H);1.47(t,3H);1.17(t,3H);0.71(m,2H);0.49(m,2H);

[0715] Embodiment No. 2-276: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);9.10(t,1H);7.86(d,1H);7.79(d,1H);6.13(tt,1H);4.36(q,2H);3.78(m,1H);3.63(m,1H);2.77(m,2H);1.48(t,3H);1.17(t,3H);

[0716] Embodiment No. 2-277: 1 H-NMR (400MHz, DMSO-d6): δ = 11.62 (br s,1H);8.58(q,1H);7.79(d,1H);7.65(d,1H);6.90(t,1H);4.35(q,2H);2.81(d,3H);2.74(q,2H);1.47(t,3H);1.15(t,3H);

[0717] Embodiment No. 2-278: 1 H-NMR (400MHz, DMSO-d6): δ = 11.61 (br s,1H);8.67(t,1H);7.79(d,1H);7.65(d,1H);6.90(t,1H);4.35(q,2H);3.31(m,2H);2.76(q,2H);1.48(t,3H);1.15(2x t,6H);

[0718] Embodiment No. 2-279: 1H-NMR (400MHz, DMSO-d6): δ = 11.60 (br s,1H);8.74(d,1H);7.78(d,1H);7.64(d,1H);6.89(t,1H);4.35(q,2H);2. 86(m,1H);2.73(m,2H);1.47(t,3H);1.15(t,3H);0.72(m,2H);0.53(m,2H);

[0719] Embodiment No. 2-286: 1 H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s, 1H); 8.45 (q, 1H); 7.77 (br s,2H);4.38(q,2H);2.79(d,3H);2.11(m,1H);1.48(t,3H);0.84(m,2H);0.64(m,2H);

[0720] Embodiment No. 2-287: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.51 (t, 1H); 7.77 (br s,2H);4.38(q,2H);3.29(m,2H);2.14(m,1H);1.48(t,3H);1.13(t,3H);0.84(m,2H);0.67(m,2H);

[0721] Embodiment No. 2-288: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.59 (d, 1H); 7.76 (br s,2H);4.37(q,2H);2.79(m,1H);2.12(m,1H);1.48(t,3H);0.85(m,2H);0.70(m,2H);0.66(m,2H);0.51(br s,2H);

[0722] Embodiment No. 2-289: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.64 (t, 1H); 7.77 (br s,2H);4.38(q,2H);3.13(m,2H);2.15(m,1H);1.49(t,3H);1.03(m,1H);0.86(m,2H);0.68(m,2H);0.45(m,2H);0.23(m,2H);

[0723] Embodiment No. 2-291: 1H-NMR (400MHz, DMSO-d6): δ = 11.60 (br s, 1H); 9.03 (t, 1H); 7.80 (br s,2H);6.13(tt,1H);4.38(q,2H);3.69(m,2H);2.13(m,1H);1.49(t,3H);0.87(m,2H);0.65(m,2H);

[0724] Embodiment No. 2-292: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.55 (d, 1H); 7.76 (br s, 2H); 4.38 (q, 2H); 3.37 (m, 1H); 2.17 (m, 1H); 1.49 (t, 3H); 1.20 (br s,3H);0.89(m,3H);0.70(br s,2H);0.45(m,2H);0.24(m,1H);

[0725] Embodiment No. 2-304: 1 H-NMR (400MHz, DMSO-d6): δ = 11.52 (br s,1H);8.53(q,1H);7.72(d,1H);7.66(d,1H);6.94(t,1H);4.37(q,2H);2.81(d,3H);2.16(m,1H);1.49(t,3H);0.83(m,2H);0.58(m,2H);

[0726] Embodiment No. 2-305: 1 H-NMR (400MHz, DMSO-d6): δ = 11.52 (br s,1H);8.61(t,1H);7.72(d,1H);7.66(d,1H);6.95(t,1H);4.38(q,2H);2 .32(q,2H);2.19(m,1H);1.49(t,3H);1.14(3H);0.83(m,2H);0.61(m,2H);

[0727] Embodiment No. 2-306: 1 H-NMR (400MHz, DMSO-d6): δ = 11.51 (br s,1H);8.68(d,1H);7.72(d,1H);7.65(d,1H);6.94(t,1H);4.37(q,2H);2. 85(m,1H);2.16(m,1H);1.48(t,3H);0.83(m,2H);0.71(m,2H);0.58(m,4H);

[0728] Embodiment No. 2-337: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.98 (br s, 2H); 4.37 (q, 2H); 3.81 (br s, 1H); 2.07 (br s, 3H); 1.47 (t, 3H);

[0729] Embodiment No. 2-338: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.22 (s, 1H); 8.00 (s, 1H); 7.96 (d, 1H); 7.93 (d, 1); 4.39 (q, 2H); 1.49 (t, 3H);

[0730] Embodiment No. 2-339: 1 H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s,1H);8.70(d,1H);7.78(d,1H);7.64(d,1H);6.91(t,1H);4.35(q,2H);3.45(m,1H);2. 38(s,3H);1.47(t,3H);1.22(d,3H);0.93(m,1H);0.45(m,2H);0.35(m,1H);0.27(m,1H);

[0731] Embodiment No. 2-340: 1 H-NMR (400MHz, DMSO-d6): δ = 11.81 (br s,1H);8.79(d,1H);7.84(d,1H);7.81(d,1H);6.91(t,1H);4.39(q,2H);3.45(m,1 H);1.48(s,3H);1.23(d,3H);0.93(m,1H);0.44(m,2H);0.38(m,1H);0.29(m,1H);

[0732] Embodiment No. 2-341: 1 H-NMR (400MHz, DMSO-d6): δ = 11.68 (br s,1H);8.67(d,1H);7.82(d,1H);7.76(d,1H);4.36(q,2H);3.40(m,1H);2.82(q,2H);2. 78(m,1H);1.48(t,3H);1.22(t,3H);1.19(t,3H);0.91(m,1H);0.45(m,2H);0.29(m,2H);

[0733] Embodiment No. 2-342: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s, 1H); 8.68 (t, 1H); 7.83 (d, 1H); 7.62 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (s, 3H); 1.14 (t, 3H);

[0734] Embodiment No. 2-343: 1 H-NMR (400MHz, DMSO-d6): δ = 11.75 (br s,1H);8.74(d,1H);7.82(d,1H);7.61(d,1H);4.37(q,2H);2.79(m,1H);1.47(t,3H);0.72(m,2H);0.56(m,2H);

[0735] Embodiment No. 2-344: 1 H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s,1H);8.67(t,1H);7.79(d,1H);7.64(d,1H);6.90(t,1H);4.35(q,2H);3.24(m,2H);2.35(s,3H);1.54(m,2H);1.47(t,3H);0.92(t,3H);

[0736] Embodiment No. 2-345: 1 H-NMR (400MHz, DMSO-d6): δ = 11.58 (br s,1H);8.56(d,1H);7.78(d,1H);7.63(d,1H);6.91(t,1H);4.34(q,2H);4.11(m,1H);2.36(s,3H);1.47(t,3H);1.16(d,6H);

[0737] Embodiment No. 2-346: 1 H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s,1H);8.74(t,1H);7.78(d,1H);7.64(d,1H);6.93(t,1H);4.35(q,2H);3.47(m,4H);3.28(s,3H);2.35(s,3H);1.47(t,3H);

[0738] Embodiment No. 2-347: 1H-NMR (400MHz, DMSO-d6): δ = 11.59 (br s,1H);8.81(t,1H);7.79(d,1H);7.65(d,1H);7.01(t,1H);4.35(q,2H);3.49(m,2H);2.68(m,2H);2.38(s,3H);2.11(s,3H);1.47(t,3H);

[0739] Embodiment No. 2-348: 1 H-NMR (400MHz, DMSO-d6): δ = 11.77 (br s, 1H); 8.71 (t, 1H); 7.72 (d, 1H); 7.69 (d, 1H); 4.37 (q, 2H); 3.28 (m, 2H); 1.47 (t, 3H); 1.14 (t, 3H);

[0740] Embodiment No. 2-349: 1 H-NMR (400MHz, DMSO-d6): δ = 11.76 (br s,1H);8.77(d,1H);7.71(d,1H);7.68(d,1H);4.37(q,2H);2.80(m,2H);1.47(t,3H);0.72(m,2H);0.54(m,2H);

[0741] Embodiment No. 2-350: 1 H-NMR (400MHz, DMSO-d6): δ = 11.71 (br s,1H);8.57(d,1H);7.94(d,1H);7.85(d,1H);4.44(q,2H);3.47(m,1H);2. 46(s,3H);1.49(t,3H);1.21(d,3H);0.91(m,1H);0.42(m,2H);0.33(m,2H);

[0742] Embodiment No. 2-351: 1 H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s,1H);8.66(d,1H);7.83(d,1H);7.79(d,1H);6.89(t,1H);4.44(q,2H);3. 51(m,1H);2.45(s,3H);1.49(t,3H);1.23(d,3H);0.93(m,1H);0.30(m,2H);

[0743] Embodiment No. 2-352: 1H-NMR (400MHz, DMSO-d6): δ = 11.54 (br s, 1H); 8.35 (q, 1H); 7.73 (d, 1H); 7.19 (d, 1H); 7.33 (m, 2H); 3.85 (s, 3H); 2.74 (d, 3H); 1.45 (t, 3H);

[0744] Embodiment No. 2-353: 1 H-NMR (400MHz, DMSO-d6): δ = 11.53 (br s,1H);8.41(t,1H);7.72(d,1H);7.18(d,1H);4.33(q,2H);3.85(s,3H);3.24(m,2H);1.46(t,3H);1.10(t,3H);

[0745] Embodiment No. 2-354: 1 H-NMR (400MHz, DMSO-d6): δ = 11.53 (br s,1H);8.48(d,1H);7.72(d,1H);7.18(d,1H);4.33(q,2H);3.85(s,3H);2.80(m,1H);1.47(t,3H);0.69(m,2H);0.48(m,2H);

[0746] Embodiment No. 2-357: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s, 1H); 11.93 (br s, 1H); 8.05 (d, 1H); 7.99 (d, 1H); 4.38 (q, 2H); 3.74 (s, 3H); 1.47 (t, 3H);

[0747] Embodiment No. 2-358: 1 H-NMR (400MHz, DMSO-d6): δ = 11.94 (br s, 1H); 11.81 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 3.97 (m, 2H); 1.48 (t, 3H); 1.23 (t, 3H);

[0748] Embodiment No. 2-359: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 11.81 (br s,1H);8.04(d,1H);7.98(d,1H);4.38(q,2H);3.88(m,2H);1.64(m,2H);1.47(t,3H);0.94(t,3H);

[0749] Embodiment No. 2-360: 1 H-NMR (400MHz, DMSO-d6): δ = 11.93 (br s, 1H); 11.65 (br s, 1H); 8.04 (d, 1H); 7.98 (d, 1H); 4.38 (q, 2H); 4.18 (m, 2H); 1.47 (t, 3H); 1.23 (d, 6H);

[0750] Embodiment No. 2-361: 1 H-NMR (400MHz, DMSO-d6): δ = 11.92 (br s, 1H); 11.87 (br s, 1H); 7.97 (d, 1H); 7.81 (d, 1H); 7.04 (t, 1H); 4.37 (q, 2H); 3.76 (s, 3H); 1.47 (t, 3H);

[0751] Embodiment No. 2-362: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 11.81 (br s,1H);7.97(d,1H);7.81(d,1H);7.02(t,1H);4.37(q,2H);3.99(q,2H);1.47(t,3H);1.23(t,3H);

[0752] Embodiment No. 2-363: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 11.81 (br s,1H);7.96(d,1H);7.81(d,1H);7.02(t,1H);4.38(q,2H);3.91(t,2H);1.65(m,2H);1.48(t,3H);0.95(t,3H);

[0753] Embodiment No. 2-364: 1 H-NMR (400MHz, DMSO-d6): δ = 11.87 (br s, 1H); 11.67 (br s,1H);7.96(d,1H);7.81(d,1H);7.01(t,1H);4.37(q,2H);4.21(m,1H);1.47(t,3H);1.23(d,6H);

[0754] Embodiment No. 3-26: 1H-NMR (400MHz, DMSO-d6): δ = 11.63 (br s,1H);8.59(t,1H);7.80(d,1H);7.76(d,1H);4.30(t,2H);3.28(m,2H);2.35(s,3H);1.88(m,2H);1.11(t,3H);0.88(t,3H);

[0755] Embodiment No. 3-27: 1 H-NMR (400MHz, DMSO-d6): δ = 11.62 (br s,1H);8.66(d,1H);7.80(d,1H);7.75(d,1H);4.30(t,2H);2.81(m,1H);2.34(s,3H);1.88(m,2H);0.88(t,3H);0.71(m,2H);0.49(m,2H);

[0756] Embodiment No. 3-125: 1 H-NMR (400MHz, DMSO-d6): δ = 11.90 (br s,1H);8.85(d,1H);8.06(d,1H);8.00(d,1H);4.32(t,2H);3.31(s,3H);2.77(m,1H);1.88(m,2H);0.88(t,3H);0.70(m,2H);0.58(m,2H);

[0757] Embodiment No. 3-129: 1 H-NMR (400MHz, DMSO-d6): δ = 11.88 (br s, 1H); 8.70 (q, 1h); 7.96 (d, 1H); 7.93 (d, 1H); 4.32 (t, 2H); 2.80 (d, 3H); 1.88 (m, 2H); 0.88 (t, 3H);

[0758] Embodiment No. 3-208: 1 H-NMR (400MHz, DMSO-d6): δ = 11.85 (br s, 1H); 8.73 (t, 1H); 7.95 (d, 1H); 7.89 (d, 1H); 4.34 (t, 2H); 3.29 (m, 2H); 1.89 (m 2H);1.12(t,3H);0.89(t,3H);

[0759] Embodiment No. 3-273: 1H-NMR (400MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.68 (d, 1H); 7.81 (d, 1H); 7.76 (d, 1H); 4.30 (t, 2H); 2.81 (m 2H); 2.70 (m, 1H); 1.89 (m, 2H); 1.17 (t, 3H); 0.89 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

[0760] Embodiment No. 3-337: 1 H-NMR (400MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.97 (br s, 2H); 4.31 (t, 2H); 3.89 (br s, 1H); 2.07 (br s, 3H); 1.89 (m, 2H); 0.88 (t, 3H);

[0761] Embodiment No. 3-338: 1 H-NMR (400MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.22 (s, 1H); 8.01 (s, 1H); 7.94 (s, 2H); 4.34 (t, 2H); 1.90 (m, 2H); 0-90 (t, 3H);

[0762] Embodiment No. 4-212: 1 H-NMR (400MHz, DMSO-d6): δ = 11.22 (br s,1H);8.66(d,1H);7.91(s,1H);7.77(d,1H);7.72(d,1H);3.77(s,3H);2.80(m,2H);2.71(m,1H);1.17(t,3H);0.71(m,2H);0.48(m,2H);

[0763] Embodiment No. 5-58: 1 H-NMR (400MHz, DMSO-d6): δ = 12.45 (br s, 1H); 9.05 (s, 1H); 8.46 (q, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 2.79 (d, 3H); 2.39 (s, 3H);

[0764] Embodiment No. 5-59: 1 H-NMR (400MHz, DMSO-d6): δ = 12.42 (br s, 1H); 9.07 (s, 1H); 8.53 (t, 1H); 7.90 (d, 1H); 7.78 (d, 1H); 3.28 (m, 2H); 2.40 (s, 3H); 1.12 (t, 3H);

[0765] Embodiment No. 5-74: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s, 1H); 9.05 (s, 1H); 8.52 (q, 1H); 7.77 (d, 1H); 7.72 (d, 1H); 6.88 (t, 1H); 2.81 (d, 1H); 2.37 (s, 3H);

[0766] Embodiment No. 5-75: 1 H-NMR (400MHz, DMSO-d6): δ = 12.35 (br s,1H);9.05(s,1H);8.60(t,1H);7.77(d,1H);7.72(d,1H);6.88(t,1H);3.32(m,2H);2.39(s,3H);1.14(t,3H);

[0767] Embodiment No. 5-117: 1 H-NMR (400MHz, DMSO-d6): δ = 12.62 (br s, 1H); 9.07 (s, 1H); 8.74 (t, 1H); 7.89 (s, 2H); 3.31 (m, 2H); 1.11 (t, 3H);

[0768] Embodiment No. 5-122: 1 H-NMR (400MHz, DMSO-d6): δ = 12.55 (br s, 1H); 9.07 (s, 1H); 8.70 (q, 1H); 7.82 (d, 1H); 7.75 (d, 1H); 6.95 (t, 1H); 2.80 (d, 3H);

[0769] Embodiment No. 5-123: 1 H-NMR (400MHz, DMSO-d6): δ = 12.56 (br s, 1H); 9.06 (s, 1H); 8.77 (t, 1H); 7.82 (d, 1H); 7.74 (d, 1H); 3.29 (m, 2H); 1.13 (t, 3H);

[0770] Embodiment No. 5-253: 1 H-NMR (400MHz, DMSO-d6): δ = 12.61 (br s, 1H); 9.07 (s, 1H); 8.19 (s, 1H); 7.96 (s, 1H); 7.89 (d, 1H); 7.86 (d, 1H);

[0771] Embodiment No. 5-254: 1H-NMR (400MHz, DMSO-d6): δ = 12.67 (br s, 1H); 9.59 (t, 1H); 9.08 (s, 1H); 7.96 (s, 2H); 4.41 (d, 2H);

[0772] Embodiment No. 5-255: 1 H-NMR (400MHz, DMSO-d6): δ = 12.71 (br s, 1H); 10.85 (br s, 1H); 9.08 (s, 1H); 7.98 (m, 2H); 7.65 (m, 2H); 7.38 (m, 2H); 7.15 (m, 1H);

[0773] Embodiment No. 6-26: 1 H-NMR (400MHz, DMSO-d6): δ = 12.18 (br s, 1H); 8.58 (t, 1H); 7.71 (s, 2H); 3.29 (m, 2H); 2.50 (s, 3H); 2.31 (s, 3H); 1.10 (t, 3H);

[0774] Embodiment No. 6-32: 1 H-NMR (400MHz, DMSO-d6): δ = 12.11 (br s,1H);8.64(t,1H);7.67(d,1H);7.59(d,1);6.89(t,1H);3.30(m,2H);2.49(s,3H);2.31(s,3H);1.12(t,3H);

[0775] Embodiment No. 6-33: 1 H-NMR (400MHz, DMSO-d6): δ = 12.10 (br s,1H);8.70(d,1H);7.67(d,1H);7.58(d,1H);6.89(t,1H);2.85(m,1H);2.49(s,3H);2.28(s,3H);0.70(m,2H);0.53(m,2H);

[0776] Embodiment No. 6-34: 1 H-NMR (400MHz, DMSO-d6): δ = 12.11 (br s,1H);8.78(t,1H);7.68(d,1H);7.60(d,1H);6.90(t,1H);3.15(m,2H);2.49(s,3H);2.33(s,3H);1.04(m,1H);0.46(m,2H);0.23(m,2H);

[0777] Embodiment No. 6-43:1 H-NMR (400MHz, DMSO-d6): δ = 12.19 (br s, 1H); 8.49 (q, 1H); 7.77 (d, 1H); 7.61 (d, 1H); 3.80 (s, 3H); 2.77 (d, 3H); 2.49 (s, 3H);

[0778] Embodiment No. 6-44: 1 H-NMR (400MHz, DMSO-d6): δ = 12.17 (br s, 1H); 8.57 (t, 1H); 7.76 (d, 1H); 7.62 (d, 1H); 3.81 (s, 3H); 3.27 (m, 2H); 2.49 (s, 3H); 1.10 (t, 3H);

[0779] Embodiment No. 6-45: 1 H-NMR (400MHz, DMSO-d6): δ = 12.17 (br s,1H);8.64(d,1H);7.76(d,1H);7.61(d,1H);3.80(s,3H);2.79(m,1H);2.49(s,3H);0.70(m,2H);0.47(m,2H);

[0780] Embodiment No. 6-49: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.53 (q, 1H); 7.72 (d, 1H); 7.49 (d, 1H); 6.93 (t, 1H); 3.79 (s, 3H); 2.79 (d, 3H); 2.49 (s, 3H);

[0781] Embodiment No. 6-50: 1 H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s,1H);8.61(t,1H);7.72(d,1H);7.49(d,1H);6.94(t,1H);3.81(s,3H);3.29(m,2H);2.49(s,3H);1.12(t,3H);

[0782] Embodiment No. 6-51: 1 H-NMR (400MHz, DMSO-d6): δ = 12.02 (br s,1H);8.68(d,1H);7.72(d,1H);7.48(d,1H);6.92(t,1H);3.79(s,3H);2.84(m,1H);2.49(s,3H);0.70(m,2H);0.53(m,2H);

[0783] Embodiment No. 6-58: 1 H-NMR (400MHz, DMSO-d6): δ = 12.24 (br s, 1H); 8.46 (q, 1H); 7.90 (d, 1H); 7.76 (d, 1H); 2.79 (d, 3H); 2.49 (s, 3H); 2.39 (s, 3H);

[0784] Embodiment No. 6-60: 1 H-NMR (400MHz, DMSO-d6): δ = 12.25br s, 1H); 8.61 (d, 1H); 7.89 (d, 1H); 7.76 (d, 1H); 2.79 (m, 1H); 2.49 (s, 3H); 2.39 (s, 3H); 0.71 (m, 2H); 0.52 (br s,1H);

[0785] Embodiment No. 6-74: 1 H-NMR (400MHz, DMSO-d6): δ = 12.18 (br s, 1H); 8.52 (q, 1H); 7.76 (d, 1H); 7.70 (d, 1H); 6.88 (t, 1H); 2.81 (d, 3H); 2.49 (s, 3H); 2.38 (s, 3H);

[0786] Embodiment No. 6-75: 1 H-NMR (400MHz, DMSO-d6): δ = 12.16 (br s,1H);8.59(t,1H);7.77(d,1H);7.69(d,1H);6.88(t,1H);3.31(m,2H);2.49(s,3H);2.39(s,3H);1.14(t,3H);

[0787] Embodiment No. 6-76: 1 H-NMR (400MHz, DMSO-d6): δ = 12.17 (br s,1H);8.67(d,1H);7.76(d,1H);7.69(d,1H);6.88(t,1H);2.84(m,1H);2.49(s,3H);2.37(s,3H);0.71(m,2H);0.57(m,2H);

[0788] Embodiment No. 6-116: 1 H-NMR (400MHz, DMSO-d6): δ = 12.44 (br s, 1H); 8.67 (q, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 2.78 (d, 3H); 2.50 (s, 3H);

[0789] Embodiment No. 6-117: 1 H-NMR (400MHz, DMSO-d6): δ = 12.44 (br s, 1H); 8.74 (t, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 3.27 (m, 2H); 2.49 (s, 3H); 1.11 (t, 3H);

[0790] Embodiment No. 6-118: 1 H-NMR (400MHz, DMSO-d6): δ = 12.44 (br s, 1H); 8.81 (d, 1H); 7.88 (d, 1H); 7.85 (d, 1H); 2.79 (m, 1H); 2.49 (s, 3H); 0.72 (m, 2H); 0.50 (br s, 2H);

[0791] Embodiment No. 6-120: 1 H-NMR (400MHz, DMSO-d6): δ = 12.51 (br s, 1H); 9.54 (t, 1H); 7.93 (s, 2H); 4.14 (m, 2H); 2.52 (s, 3H);

[0792] Embodiment No. 6-124: 1 H-NMR (400MHz, DMSO-d6): δ = 12.36 (br s,1H);8.83(d,1H);7.80(d,1H);7.72(d,1H);6.93(t,1H);2.83(m,1H);2.48(s,3H);0.71(m,2H);0.54(m,2H);

[0793] Embodiment No. 6-141: 1 H-NMR (400MHz, DMSO-d6): δ = 12.31 (br s, 1H); 8.69 (t, 1H); 7.76 (d, 1H); 7.57 (d, 1H); 3.27 (m, 2H); 2.48 (s, 3H); 1.13 (t, 3H);

[0794] Embodiment No. 6-143: 1 H-NMR (400MHz, DMSO-d6): δ = 12.31 (br s,1H);8.79(t,1H);7.76(d,1H);7.57(d,1H);3.15(m,2H);2.49(s,3H);1.01(m,1H);0.44(m,2H);0.25(m,2H);

[0795] Embodiment No. 6-144: 1H-NMR (400MHz, DMSO-d6): δ = 12.32 (br s, 1H); 9.48 (t, 1H); 7.80 (d, 1H); 7.63 (d, 1H); 4.12 (m, 2H); 2.49 (s, 3H);

[0796] Embodiment No. 6-145: 1 H-NMR (400MHz, DMSO-d6): δ = 12.31 (br s, 1H); 9.21 (t, 1H); 7.78 (d, 1H); 7.61 (d, 1H); 6.13 (tt, 1H); 3.69 (m, 2H); 2.49 (s, 3H);

[0797] Embodiment No. 6-159: 1 H-NMR (400MHz, DMSO-d6): δ = 12.41 (br s, 1H); 8.72 (t, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 3.28 (m, 2H); 2.50 (s, 3H); 1.11 (t, 3H);

[0798] Embodiment No. 6-161: 1 H-NMR (400MHz, DMSO-d6): δ = 12.42 (br s,1H);8.82(t,1H);7.91(d,1H);7.80(d,1H);3.13(m,2H);2.49(s,3H);1.00(m,1H);0.45(m,2H);0.23(m,2H);

[0799] Embodiment No. 6-165: 1 H-NMR (400MHz, DMSO-d6): δ = 12.35 (br s, 1H); 8.75 (t, 1H); 7.77 (d, 1H); 7.74 (d, 1H); 6.91 (t, 1H); 3.29 (m, 2H); 2.49 (s, 3H); 1.13 (t, 3H);

[0800] Embodiment No. 6-166: 1 H-NMR (400MHz, DMSO-d6): δ = 12.36 (br s,1H);8.81(d,1H);7.76(d,1H);7.73(d,1H);6.91(t,1H);2.80(m,1H);2.49(s,3H);0.71(m,2H);0.56(m,2H);

[0801] Embodiment No. 6-167: 1H-NMR (400MHz, DMSO-d6): δ = 12.35 (br s,1H);8.88(t,1H);7.78(d,1H);7.74(d,1H);6.91(t,1H);3.15(m,2H);2.49(s,3H);1.03(m,1H);0.46(m,2H);0.24(m,2H);

[0802] Embodiment No. 6-168: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s, 1H); 9.52 (t, 1H); 7.80 (s, 2H); 6.90 (t, 1H); 4.13 (m, 2H); 2.49 (s, 3H);

[0803] Embodiment No. 6-169: 1 H-NMR (400MHz, DMSO-d6): δ=12.37(br s,1H)M 9.26(t,1H); 7.80(d,1H); 7.78(d,1H); 6.92(t,1H); 6.17(tt,1H); 3.71(m,2H); 2.49(s,3H);

[0804] Embodiment No. 6-210: 1 H-NMR (400MHz, DMSO-d6): δ = 12.22 (br s, 1H); 8.52 (q, 1H); 7.72 (s, 2H); 2.78 (d, 3H); 2.66 (m, 2H); 2.46 (s, 3H); 1.13 (t, 3H);

[0805] Embodiment No. 6-211: 1 H-NMR (400MHz, DMSO-d6): δ = 12.21 (br s, 1H); 8.61 (t, 1H); 7.72 (br s,2H);3.28(m,2H);2.78(m,1H);2.69(m,1H);2.49(s,3H);1.15(t,3H);1.10(t,3H);

[0806] Embodiment No. 6-212: 1 H-NMR (400MHz, DMSO-d6): δ = 12.19 (br s,1H);8.66(d,1H);7.71(s,2H);2.80(m,2H);2.68(m,1H);2.52(s,3H);1.13(t,3H);0.71(m,2H);0.48(m,2H);

[0807] Embodiment No. 6-228:1 H-NMR (400MHz, DMSO-d6): δ = 12.08 (br s,1H);8.61(t,1H);7.73(d,1H);7.63(d,1H);3.12(m,2H);2.49(s,3H);2. 11(m,1H); 1.02(m,1H); 0.80(m,2H); 0.62(m,2H); 0.46(m,2H); 0.22(m,2H);

[0808] Embodiment No. 6-230: 1 H-NMR (400MHz, DMSO-d6): δ = 12.11 (br s,1H);9.01(t,1H);7.76(d,1H);7.67(d,1H);6.12(tt,1H);3.68(m,2H);2.49(s,3H);2.10(m,1H);0.83(m,2H);0.59(m,2H);

[0809] Embodiment No. 6-231: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s,1H);8.51(q,1H);7.63(d,1H);7.60(d,1H);6.92(t,1H);2.81(d,3H);2.49(s,3H);2.13(m,1H);0.79(m,2H);0.51(m,2H);

[0810] Embodiment No. 6-233: 1 H-NMR (400MHz, DMSO-d6): δ = 12.01 (br s,1H);8.66(d,1H);7.60(m,2H);6.92(t,1H);2.84(m,1H);2.49(s,3H);2.12(m,1H);0.79(m,2H);0.70(m,2H);0.54(m,4H);

[0811] Embodiment No. 6-252: 1 H-NMR (400MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.91 (br s, 2H); 4.30 (br s, 1H); 2.38 (s, 3H); 1.99 (s, 3H);

[0812] Embodiment No. 6-253: 1H-NMR (400MHz, DMSO-d6): δ = 12.45 (br s, 1H); 8.20 (s, 1H); 7.98 (s, 1H); 7.89 (d, 1H); 7.86 (d, 1H); 2.52 (s, 3H);

[0813] Embodiment No. 6-254: 1 H-NMR (400MHz, DMSO-d6): δ = 12.44 (br s,1H);8.73(d,1H);7.85(d,1H);7.88(d,1H);3.43(m,1H);1.19(m,3H);0.89(m,1H);0.42(m,2H);0.29(m,2H);

[0814] Embodiment No. 6-255: 1 H-NMR (400MHz, DMSO-d6): δ = 12.19 (br s, 1H); 8.50 (d, 1H); 7.70 (s, 2H); 4.07 (m, 1H); 2.49 (s, 3H); 2.31 (s, 3H); 1.15 (d, 3H); 1.11 (d, 3H);

[0815] Embodiment No. 6-256: 1 H-NMR (400MHz, DMSO-d6): δ = 12.20 (br s,1H);8.84(d,1H);7.71(s,2H);4.36(m,1H);2.49(s,3H);2.30(s,3H);2.24(m,2H);1.97(m,2H);1.48(m,2H);

[0816] Embodiment No. 6-257: 1 H-NMR (400MHz, DMSO-d6): δ = 12.31 (br s,1H);8.65(d,1H);7.75(d,1H);7.57(d,1H);3.48(m,1H);2.49(s,3H);1.21(d,3H);0.91(m,1H);0.42(m,2H);0.34(m,2H);

[0817] Embodiment No. 6-258: 1H-NMR (400MHz, DMSO-d6): δ = 12.11 (br s,1H);8.69(d,1H);7.68(d,1H);7.59(d,1H);6.89(t,1H);3.44(m,1H);2.49(s,3 H);2.34(s,3H);1.22(d,3H);0.92(m,1H);0.43(m,2H);0.34(m,1H);0.26(m,1H);

[0818] Embodiment No. 6-259: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s,1H);8.79(t,1H);7.80(d,1H);7.74(d,1H);6.92(t,1H);3.23(m,2H);2.49(s,3H);1.54(m,2H);0.92(t,3H);

[0819] Embodiment No. 6-260: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s, 1H); 8.69 (d, 1H); 7.79 (d, 1H); 7.73 (d, 1H); 6.92 (t, 1H); 4.08 (m, 1H); 2.49 (s, 3H); 1.16 (d, 6H);

[0820] Embodiment No. 6-261: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s,1H);9.03(d,1H);7.80(d,1H);7.73(d,1H);6.91(t,1H);4.36(m,1H);2.49(s,3H);2.26(m,2H);2.01(m,2H);1.69(m,2H);

[0821] Embodiment No. 6-262: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s, 1H); 8.90 (t, 1H); 7.80 (d, 1H); 7.74 (d, 1H); 6.94 (t, 1H); 3.45 (m, 4H); 3.28 (s, 3H); 2.49 (s, 3H);

[0822] Embodiment No. 6-263: 1H-NMR (400MHz, DMSO-d6): δ = 12.35 (br s,1H);8.91(t,1H);7.80(d,1H);7.73(d,1H);6.95(t,1H);3.98(m,1H);3.78(m,1 H); 3.65 (m, 1H); 3.34 (m, 2H); 2.49 (s, 3H); 1.94 (m, 1H); 1.84 (m, 2H); 1.62 (m, 1H);

[0823] Embodiment No. 6-264: 1 H-NMR (400MHz, DMSO-d6): δ = 12.38 (br s,1H);9.43(t,1H);7.82(d,1H);7.75(d,1H);7.45(m,1H);7.07(m,1H);6.99(m,1H);6.90(t,1H);4.67(d,3H);2.49(s,3H);

[0824] Embodiment No. 6-265: 1 H-NMR (400MHz, DMSO-d6): δ = 12.39 (br s, 1H); 9.10 (t, 1H); 7.83 (d, 1H); 7.79 (d, 1H); 7.57 (t, 1H); 4.16 (d, 2H); 3.01 (s, 3H); 2.88 (s, 3H);

[0825] Embodiment No. 6-266: 1 H-NMR (400MHz, DMSO-d6): δ = 12.41 (br s, 1H); 10.83 (br s,1H);7.88(d,1H);7.80(d,1H);7.69(m,2H);7.37(m,2H);7.15(m,1H);7.10(t,1H);2.49(s,3H);

[0826] Embodiment No. 6-267: 1 H-NMR (400MHz, DMSO-d6): δ = 12.35 (br s,1H);8.77(d,1H);7.75(m,2H);6.89(t,1H);3.45(m,1H);2.49(s,3H);1.22(d,3H);0.92(m,1H);0.41(m,3H);0.28(m,1H);

[0827] Embodiment No. 6-268: 1H-NMR (400MHz, DMSO-d6): δ = 12.08 (br s,1H);8.53(d,1H);7.73(d,1H);7.62(d,1H);3.36(m,1H);2.49(s,3H);2.21(m,1H);1.20(d,3H);0.89(m,1H);0.83(m,2H);0.63(br s,2H); 0.44(m,2H); 0.32(m,1H); 0.24(m,1H).

[0828] B. Formulation Examples

[0829] a) A dusting product is obtained by mixing 10 parts by weight of the compound of formula (I) and / or its salt with 90 parts by weight of talc as an inert substance and pulverizing the mixture in a hammer mill.

[0830] b) Wettable powders which are readily dispersible in water are obtained by mixing 25 parts by weight of the compound of formula (I) and / or its salt, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.

[0831] c) obtaining a dispersion concentrate that is easily dispersible in water by the following method: mixing 20 parts by weight of the compound of formula (I) and / or its salt with 6 parts by weight of alkylphenol polyglycol ether ( X207), 3 parts by weight of isotridecanol polyethylene glycol ether (8EO) and 71 parts by weight of paraffin mineral oil (boiling point range is, for example, about 255°C to above 277°C) are mixed, and the mixture is ground in a friction ball mill to a fineness of less than 5 microns.

[0832] d) An emulsifiable concentrate is obtained by mixing 15 parts by weight of the compound of formula (I) and / or its salt, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0833] e) obtaining water dispersible granules by the following method:

[0834] Mix the following substances

[0835] 75 parts by weight of a compound of formula (I) and / or a salt thereof,

[0836] 10 parts by weight of calcium lignin sulfonate,

[0837] 5 parts by weight of sodium lauryl sulfate,

[0838] 3 parts by weight of polyvinyl alcohol and

[0839] 7 parts by weight of kaolin,

[0840] The mixture was ground in a pin-disc mill and the powder was granulated in a fluidized bed by spraying water as granulating liquid.

[0841] f) obtaining water dispersible granules by the following method:

[0842] The following substances were homogenized and pre-crushed in a colloid mill:

[0843] 25 parts by weight of a compound of formula (I) and / or a salt thereof,

[0844] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,

[0845] 2 parts by weight of sodium oleoyl methyl taurate,

[0846] 1 part by weight of polyvinyl alcohol,

[0847] 17 parts by weight of calcium carbonate and

[0848] 50 parts by weight of water,

[0849] The mixture was subsequently ground in a ball mill, and the resulting suspension was atomized through a single-phase nozzle in a spray tower and dried.

[0850] C. Biological Examples

[0851] The abbreviations for harmful plants mean:

[0852] ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides

[0853] AVEFA Wild Oats (Avena fatua) AMARE Amaranthus retroflexus

[0854] CYPES Cyperus esculentus DIGSA Digitaria sanguinalis

[0855] ECHCG Echinochloa crus-galli HORMU Hordeum murinum

[0856] LOLMU Lolium multiflorum LOLRI Lolium rigidum

[0857] MATIN Matricaria inodora PHBPU Pharbitis purpurea

[0858] POLCO Polygonum convolvulus SETVI Setaria viridis

[0859] STEME Stellaria media VERPE Veronica persica

[0860] VIOTR Viola tricolor

[0861] 1. Pre-emergence weed control of harmful plants

[0862] Seeds of monocotyledonous or dicotyledonous weed plants and crop plants are placed in sandy loam in wood fiber pots and covered with soil. Then, the compounds of the present invention prepared in the form of wettable powders (WP) or emulsifiable concentrates (EC) are applied to the surface of the covering soil in the form of aqueous suspensions or emulsions at a water application rate equivalent to 600 to 800 L / ha and with the addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and the test plants are kept under good growth conditions. After a test period of 3 weeks, the damage to the test plants is visually assessed by comparison with the untreated control group (herbicidal activity percentage (%): 100% activity = plant has died, 0% activity = like control plants). Many compounds of the present invention show very good effects on many important harmful plants. The following table illustrates the post-emergence herbicidal effect of the compounds of the present invention in an illustrative manner, and the herbicidal activity is expressed as a percentage.

[0863] Table 1a: Pre-emergence effect on ABUTH at 20 g / ha, in %

[0864]

[0865]

[0866]

[0867]

[0868]

[0869]

[0870] Table 1b: Pre-emergence effect on ABUTH at 80 g / ha, in %

[0871]

[0872]

[0873]

[0874]

[0875]

[0876]

[0877]

[0878] Table 1c: Pre-emergence effect on ABUTH at 3200 g / ha, in %

[0879]

[0880] Table 2a: Pre-emergence effect on ALOMY at 20 g / ha, in %

[0881]

[0882]

[0883]

[0884] Table 2b: Pre-emergence effect on ALOMY at 80 g / ha, in %

[0885]

[0886]

[0887]

[0888]

[0889]

[0890]

[0891] Table 2c: Pre-emergence effect on ALOMY at 320 g / ha, in %

[0892]

[0893] Table 3a: Pre-emergence effect on AMARE at 20 g / ha, in %

[0894]

[0895]

[0896]

[0897]

[0898]

[0899]

[0900]

[0901]

[0902] Table 3b: Pre-emergence effect on AMARE at 80 g / ha, in %

[0903]

[0904]

[0905]

[0906]

[0907]

[0908]

[0909]

[0910]

[0911] Table 3c: Pre-emergence effect on AMARE at 320 g / ha, in %

[0912]

[0913]

[0914] Table 4a: Pre-emergence effect of AVEFA at 20 g / ha, in %

[0915]

[0916]

[0917] Table 4b: Pre-emergence effect of AVEFA at 80 g / ha, in %

[0918]

[0919]

[0920]

[0921]

[0922]

[0923]

[0924] Table 4c: Pre-emergence effect of AVEFA at 320 g / ha, in %

[0925]

[0926] Table 5a: Pre-emergence effect on CYPES at 20 g / ha, in %

[0927]

[0928] Table 5b: Pre-emergence effect on CYPES at 80 g / ha, in %

[0929]

[0930] Table 5c: Pre-emergence effect on CYPES at 320 g / ha, in %

[0931]

[0932] Table 6a: Pre-emergence effect on ECHCG at 20 g / ha, in %

[0933]

[0934]

[0935] Table 6b: Pre-emergence effect on ECHCG at 80 g / ha, in %

[0936]

[0937]

[0938]

[0939]

[0940]

[0941]

[0942]

[0943] Table 6c: Pre-emergence effect on ECHCG at 320 g / ha, in %

[0944]

[0945] Table 7a: Pre-emergence effect on HORMU at 20 g / h, in %

[0946]

[0947] Table 7b: Pre-emergence effect on HORMU at 80 g / ha, in %

[0948]

[0949]

[0950] Table 7c: Pre-emergence effect on HORMU at 320 g / ha, in %

[0951]

[0952] Table 8a: Pre-emergence effect on LOLRI at 20 g / ha, in %

[0953]

[0954] Table 8b: Pre-emergence effect on LOLRI at 80 g / ha, in %

[0955]

[0956]

[0957]

[0958] Table 8c: Pre-emergence effect on LOLRI at 320 g / ha, in %

[0959]

[0960] Table 9a: Pre-emergence effect on MATIN at 20 g / ha, in %

[0961]

[0962]

[0963]

[0964]

[0965]

[0966]

[0967]

[0968] Table 9b: Pre-emergence effect on MATIN at 80 g / ha, in %

[0969]

[0970]

[0971]

[0972]

[0973]

[0974]

[0975]

[0976]

[0977] Table 9c: Pre-emergence effect on MATIN at 320 g / ha, in %

[0978]

[0979] Table 10a: Pre-emergence effect on PHBPU at 20 g / ha, in %

[0980]

[0981] Table 10b: Pre-emergence effect on PHBPU at 80 g / ha, in %

[0982]

[0983]

[0984]

[0985]

[0986]

[0987] Table 10c: Pre-emergence effect on PHBPU at 320 g / ha, in %

[0988]

[0989] Table 11a: Pre-emergence effect on POLCO at 20 g / ha, in %

[0990]

[0991] Table 11b: Pre-emergence effect on POLCO at 80 g / ha, in %

[0992]

[0993]

[0994]

[0995]

[0996]

[0997] Table 11c: Pre-emergence effect on POLCO at 320 g / ha, in %

[0998]

[0999] Table 12a: Pre-emergence effect on SETVI at 20 g / ha, in %

[1000]

[1001]

[1002]

[1003] Table 12b: Pre-emergence effect on SETVI at 80 g / ha, in %

[1004]

[1005]

[1006]

[1007]

[1008]

[1009]

[1010]

[1011] Table 12c: Pre-emergence effect on SETVI at 320 g / ha, in %

[1012]

[1013]

[1014] Table 13a: Pre-emergence effect on STEME at 20 g / ha, in %

[1015]

[1016]

[1017] Table 13b: Pre-emergence effect on STEME at 80 g / ha, in %

[1018]

[1019]

[1020]

[1021] Table 13c: Pre-emergence effect on STEME at 320 g / ha, in %

[1022]

[1023]

[1024] Table 14a: Pre-emergence effect on VERPE at 20 g / ha, in %

[1025]

[1026]

[1027] Table 14b: Pre-emergence effect on VERPE at 80 g / ha, in %

[1028]

[1029]

[1030]

[1031]

[1032]

[1033]

[1034] Table 14c: Pre-emergence effect on VERPE at 320 g / ha, in %

[1035]

[1036] Table 15a: Pre-emergence effect on VIOTR at 20 g / ha, in %

[1037]

[1038]

[1039]

[1040]

[1041]

[1042] Table 15b: Pre-emergence effect on VIOTR at 80 g / ha, in %

[1043]

[1044]

[1045]

[1046]

[1047]

[1048]

[1049]

[1050]

[1051] Table 15c: Pre-emergence effect on VIOTR at 320 g / ha, in %

[1052]

[1053] Table 16a: Pre-emergence effect on DIGSA at 20 g / ha, in %

[1054]

[1055]

[1056]

[1057]

[1058]

[1059] Table 16b: Pre-emergence effect on DIGSA at 80 g / ha, in %

[1060]

[1061]

[1062]

[1063]

[1064]

[1065]

[1066] Table 16c: Pre-emergence effect on DIGSA at 320 g / ha, in %

[1067]

[1068] 2. Post-emergence weed control against harmful plants

[1069] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in wood fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. The test plants are treated at the single leaf stage 2 to 3 weeks after sowing. Then, the compounds of the invention formulated in the form of wettable powders (WP) or emulsifiable concentrates (EC) are sprayed on the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l / ha and with the addition of 0.2% of a wetting agent. After the test plants have been left in a greenhouse under optimal growth conditions for about 3 weeks, the effect of the preparations is visually assessed by comparison with an untreated control group (percentage of herbicidal action (%): 100% activity = plant has died, 0% activity = like control plants). Many compounds of the invention show very good effects on many important harmful plants. The following table illustrates the post-emergence herbicidal action of the compounds of the invention in an illustrative manner, the herbicidal activity being expressed in percentage.

[1070] Table 17a: Post-emergence effect on ABUTH at 5 g / ha, in %

[1071]

[1072]

[1073]

[1074]

[1075]

[1076] Table 17b: Post-emergence effect on ABUTH at 20 g / ha, in %

[1077]

[1078]

[1079]

[1080]

[1081]

[1082]

[1083]

[1084] Table 17c: Post-emergence effect on ABUTH at 80 g / ha, in %

[1085]

[1086] Table 18a: Post-emergence effect on ALOMY at 5 g / ha, in %

[1087]

[1088]

[1089] Table 18b: Post-emergence effect on ALOMY at 20 g / ha, in %

[1090]

[1091]

[1092]

[1093]

[1094]

[1095] Table 18c: Post-emergence effect on ALOMY at 80 g / ha, in %

[1096]

[1097] Table 19a: Post-emergence effect on AMARE at 5 g / ha, in %

[1098]

[1099]

[1100]

[1101]

[1102]

[1103]

[1104] Table 19b: Post-emergence effect on AMARE at 20 g / ha, in %

[1105]

[1106]

[1107]

[1108]

[1109]

[1110]

[1111]

[1112] Table 19c: Post-emergence effect on AMARE at 80 g / ha, in %

[1113]

[1114] Table 20a: Post-emergence effect of AVEFA at 5 g / ha, in %

[1115]

[1116] Table 20b: Post-emergence effect of AVEFA at 20 g / ha, in %

[1117]

[1118]

[1119]

[1120] Table 20c: Post-emergence effect of AVEFA at 80 g / ha, in %

[1121]

[1122] Table 21a: Post-emergence effect on CYPES at 20 g / ha, in %

[1123]

[1124] Table 21b: Post-emergence effect on CYPES at 80 g / ha, in %

[1125]

[1126] Table 22a: Post-emergence effect on ECHCG at 5 g / ha, in %

[1127]

[1128]

[1129]

[1130]

[1131] Table 22b: Post-emergence effect on ECHCG at 20 g / ha, in %

[1132]

[1133]

[1134]

[1135]

[1136]

[1137]

[1138]

[1139] Table 22c: Post-emergence effect on ECHCG at 80 g / ha, in %

[1140]

[1141] Table 23a: Post-emergence effect on HORMU at 5 g / ha, in %

[1142]

[1143] Table 23b: Post-emergence effect on HORMU at 20 g / ha, in %

[1144]

[1145]

[1146] Table 23c: Post-emergence effect on HORMU at 80 g / ha, in %

[1147]

[1148]

[1149] Table 24a: Post-emergence effect on LOLRI at 5 g / ha, in %

[1150]

[1151] Table 24b: Post-emergence effect on LOLRI at 20 g / ha, in %

[1152]

[1153] Table 24c: Post-emergence effect on LOLRI at 80 g / ha, in %

[1154]

[1155]

[1156] Table 25a: Post-emergence effect on MATIN at 5 g / ha, in %

[1157]

[1158]

[1159]

[1160] Table 25b: Post-emergence effect on MATIN at 20 g / ha, in %

[1161]

[1162]

[1163]

[1164]

[1165]

[1166] Table 25c: Post-emergence effect on MATIN at 80 g / ha, in %

[1167]

[1168]

[1169] Table 26a: Post-emergence effect on PHBPU at 5 g / ha, in %

[1170]

[1171]

[1172]

[1173] Table 26b: Post-emergence effect on PHBPU at 20 g / ha, in %

[1174]

[1175]

[1176]

[1177]

[1178]

[1179] Table 26c: Post-emergence effect on PHBPU at 80 g / ha, in %

[1180]

[1181] Table 27a: Post-emergence effect on POLCO at 5 g / ha, in %

[1182]

[1183] Table 27b: Post-emergence effect on POLCO at 20 g / ha, in %

[1184]

[1185]

[1186] Table 27c: Post-emergence effect on POLCO at 80 g / ha, in %

[1187]

[1188] Table 28a: Post-emergence effect on SETVI at 5 g / ha, in %

[1189]

[1190]

[1191]

[1192]

[1193] Table 28b: Post-emergence effect on SETVI at 20 g / ha, in %

[1194]

[1195]

[1196]

[1197]

[1198]

[1199]

[1200] Table 28c: Post-emergence effect on SETVI at 80 g / ha, in %

[1201]

[1202] Table 29a: Post-emergence effect on STEME at 5 g / ha, in %

[1203]

[1204]

[1205] Table 29b: Post-emergence effect on STEME at 20 g / ha, in %

[1206]

[1207]

[1208]

[1209] Table 29c: Post-emergence effect on STEME at 80 g / ha, in %

[1210]

[1211] Table 30a: Post-emergence effect on VERPE at 5 g / ha, in %

[1212]

[1213] Table 30b: Post-emergence effect on VERPE at 20 g / ha, in %

[1214]

[1215]

[1216]

[1217]

[1218] Table 30c: Post-emergence effect on VERPE at 80 g / ha, in %

[1219]

[1220] Table 31a: Post-emergence effect on VIOTR at 5 g / ha, in %

[1221]

[1222]

[1223]

[1224]

[1225] Table 31b: Post-emergence effect on VIOTR at 20 g / ha, in %

[1226]

[1227]

[1228]

[1229]

[1230]

[1231] Table 31c: Post-emergence effect on VIOTR at 80 g / ha, in %

[1232]

[1233]

[1234] Table 32a: Post-emergence effect of DIGSA at 5 g / ha, in %

[1235]

[1236]

[1237]

[1238] Table 32b: Post-emergence effect of DIGSA at 20 g / ha, in %

[1239]

[1240]

[1241]

[1242]

[1243]

[1244] Table 32c: Post-emergence effect on DIGSA at 80 g / ha, in %

[1245]

[1246] Comparative Experiment

[1247] In subsequent experiments, the herbicidal action of a number of compounds according to the invention and the closest structural compounds known from D1 (WO 2012 / 028579 A1) was compared by the pre-emergence method and the post-emergence method under the conditions specified above. The example numbers given in the table relate to the compounds disclosed in the respective documents.

[1248] Table 5: Pre-emergence herbicidal effect

[1249]

[1250] Table 6: Post-emergence herbicidal effect

[1251]

Claims

1. Isophthalimide of formula (I) or its salt The symbols and subscripts are defined as follows: Q for Q 1 , R 1 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl, R 2 is (C1-C6)-alkyl, R x is (C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or phenyl, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R 1 O.R 2 (O) n S, R 1 O-(C1-C6)-alkyl or R 2 S(O) n -(C1-C6)-alkyl, Y is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 1 O or R 2 (O) n S, Z is hydrogen, One of the following groups, each of which is selected from halogen, cyano, R 1 C(O), R 1 OC(O),R 1 O and R 2 (O) n S is substituted by a group: (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyl-(C1-C6)-alkyl, (C2-C6)-alkynyl, (C2-C6)-alkynyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, R 2 S(O) n -(C1-C6)-alkyl, R 1 C(O), R 1 OC(O),R 1 C(O)-(C1-C6)-alkyl, R 1 OC(O)-(C1-C6)-alkyl, R 1 NH-(C1-C6)-alkyl, R 1 2N-(C1-C6)-alkyl, R 1 NHC(O)-(C1-C6)-alkyl or R 1 2NC(O)-(C1-C6)-alkyl, or One of the following groups, each of which is selected from halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, R 1 C(O) and R 1 OC(O) group substitution: phenyl or benzyl, n is 0, 1, or 2, and s is 0, 1, 2, or 3.

2. The isophthalimide of formula (I) according to claim 1 or its salt The symbols and subscripts are defined as follows: Q for Q 1 , R 1 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl, R 2 is (C1-C6)-alkyl, R x is (C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or phenyl, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R 1 O.R 2 (O) n S, R 1 O-(C1-C6)-alkyl or R 2 S(O) n -(C1-C6)-alkyl, Y is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 1 O or R 2 (O) n S, Z is hydrogen, One of the following groups, each of which is selected from halogen, cyano, R 1 C(O), R 1 OC(O),R 1 O and R 2 (O) n S is substituted by a group: (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyl-(C1-C6)-alkyl, (C2-C6)-alkynyl, (C2-C6)-alkynyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, R 2 S(O) n -(C1-C6)-alkyl, R 1 C(O), R 1 OC(O),R 1 C(O)-(C1-C6)-alkyl, R 1 NHC(O)-(C1-C6)-alkyl or R 1 2NC(O)-(C1-C6)-alkyl, or one of the following groups, each of which is substituted by s groups selected from halogen, (C1-C6)-alkyl and halo-(C1-C6)-alkyl: phenyl or benzyl, n is 0, 1, or 2, and s is 0, 1, 2, or 3.

3. The isophthalimide according to claim 1, wherein Q is Q 1 , R x is Me, Et, Pr, i-Pr, (CH2)2OMe or Ph, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, c-Pr, OMe, OEt, SMe, SEt, SO2Me, SO2Et, CH2OMe, CH2SMe, CH2SO2Me, (CH2)2SMe or (CH2)2SO2Me, Y is halogen, halo-(C1-C6)-alkyl, OMe, SMe, S(O)Me, SO2Me, SEt, S(O)Et or SO2Et, and Z is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2c-Pr, CH(Me)-c-Pr, halo-(C1-C6)-alkyl, (CH2)2OMe, (CH2)2OEt, allyl, propynyl, (CH2)2SMe, (CH2)2SO2Me, C(O)Me, C(O)cPr, C(O)OMe, C(O)OEt, CH2C(O)Me, CH2C(O)c-Pr, CH2C(O)NMe2, CH2CN, Ph, CH2Ph, OMe, OEt, OPr or Oi-Pr.

4. The isophthalimide according to claim 1, wherein Q for Q 1 , R x is Me, Et, Pr, i-Pr or (CH2)2OMe, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, c-Pr, OMe, OEt, SMe, SEt, SO2Me, SO2Et, CH2OMe, CH2SMe, CH2SO2Me, (CH2)2SMe or (CH2)2SO2Me, Y is halogen, halo-(C1-C6)-alkyl, OMe, SMe, S(O)Me, SO2Me, SEt, S(O)Et or SO2Et, and Z is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2c-Pr, CH(Me)-c-Pr, halo-(C1-C6)-alkyl, (CH2)2OMe, (CH2)2OEt, (CH2)2SMe, (CH2)2SO2Me, CH2C(O)NMe2, CH2CN, Ph, CH2Ph, OMe, OEt, OPr or Oi-Pr.

5. The isophthalimide according to claim 1, wherein Q for Q 1 , R x is Me, Et or Pr, X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt, CH2OMe or CF3, Y is F, Cl, Br, I, SMe, S(O)Me, SO2Me, CF3, CHF2 or C2F5, and Z is hydrogen, Me, Et, c-Pr, Pr, i-Pr, c-Bu, CH2-c-Pr, CH2CHF2, CH2CF3, CH(Me)-c-Pr, (CH2)2OMe, (CH2)2SMe, CH2CN, CH2C(O)NMe2, Ph, OMe, OEt, OPr or Oi-Pr.

6. The isophthalimide according to claim 1, wherein Q for Q 1 , R x is Me, Et or Pr, X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt, CH2OMe or CF3, Y is F, Cl, Br, I, SMe, S(O)Me, SO2Me, CF3, CHF2 or C2F5, and Z is hydrogen, Me, Et, c-Pr, Pr, i-Pr, c-Bu, CH2-c-Pr, CH2CHF2, CH2CF3, CH(Me)-c-Pr, (CH2)2OMe, (CH2)2SMe, CH2CN, OMe, OEt, OPr or Oi-Pr.

7. Isophthalimide of formula (Ia) or its salt The symbols and subscripts are defined as follows:

8. Isophthalimide of formula (Ia) or its salt The symbols and subscripts are defined as follows:

9. Isophthalimide of formula (Ia) or its salt The symbols and subscripts are defined as follows: 。 10. Isophthalimide of formula (Ib) or its salt The symbols and subscripts are defined as follows:

11. Isophthalimide of formula (Ib) or its salt The symbols and subscripts are defined as follows:

12. Isophthalimide of formula (Ib) or its salt The symbols and subscripts are defined as follows: 。 13. Isophthalimide of formula (Ic) or its salt The symbols and subscripts are defined as follows: 。 14. Isophthalimide of formula (Ic) or its salt The symbols and subscripts are defined as follows: 。 15. A herbicidal composition or a plant growth regulating composition, characterized in that: It contains one or more isophthalimides or salts thereof as claimed in any one of claims 1 to 14.

16. The herbicidal composition according to claim 15, further comprising a formulation adjuvant.

17. The herbicidal composition according to claim 15 or 16, comprising at least one further active ingredient selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and / or growth regulators.

18. The herbicidal composition according to claim 15 or 16, comprising a safener.

19. The herbicidal composition according to claim 18, wherein the safener is selected from the group consisting of mefenpyr-butyl, cyproconazole, isoxadiazole, cloquintocet-butyl, chlorpyrifos-butyl and mefenacet.

20. A method for controlling unwanted vegetation, characterized in that An effective amount of at least one isophthalimide or salt thereof as claimed in any one of claims 1 to 14 or a herbicidal composition as claimed in any one of claims 15 to 19 is applied to the plant or the locus of the unwanted vegetation.

21. Use of an isophthalimide or a salt thereof according to any one of claims 1 to 14 or a herbicidal composition according to any one of claims 15 to 19 for controlling unwanted plants.

22. The use according to claim 21, characterized in that The isophthalimide or the salt thereof as claimed in any one of claims 1 to 14 is used for controlling unwanted plants in crops of useful plants.

23. The use according to claim 22, characterized in that The useful plants are transgenic useful plants.

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