Substituted isophthalic diamides and their use as herbicides

Abstract

The present invention relates to isophthalic acid diamides of general formula (I) which are used as herbicides. In formula (I), X and Y represent groups such as, for example, hydrogen, alkyl and halogen. Z 1 and Z 2 represent groups such as, for example, alkyl, cycloalkyl and phenyl. Q represents a heterocycle such as a tetrazolyl group.

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, WO2013 / 017559 A1 and WO 2017 / 144402 A1 describe isophthalic acid diamides having herbicidal activity in particular, and their fundamental difference lies in the nature of the substituents on the two amide functional groups.

[0003] WO 2012 / 028579 A1 describes the following isophthalic acid diamides having herbicidal activity:

[0004] 2-chloro-N 3 ,N 3 -dimethyl-4-(methylsulfonyl)-N 1 -(1-methyl-1H-1,2,4-triazol-5-yl)isophthalic acid diamide, 2-chloro-N 3 -methoxy-N 3 -methyl-4-(methylsulfonyl)-N 1 -(1-methyl-1H-1,2,4-triazol-5-yl)isophthalic acid diamide, 2-chloro-N 1 -(1-ethyl-1H-1,2,4-triazol-5-yl)-N 3 ,N 3 -dimethyl-4-(methylsulfonyl)isophthalic acid diamide, 2-chloro-N 1 -(1-ethyl-1H-1,2,4-triazol-5-yl)-N 3 -methoxy-N 3 -methyl-4-(methylsulfonyl)isophthalic acid diamide, 2-chloro-N 3 ,N 3 -dimethyl-4-(methylsulfonyl)-N 1 -(1-phenyl-1H-1,2,4-triazol-5-yl)isophthalic acid diamide, 2-chloro-N 3 -methoxy-N 3 -methyl-4-(methylsulfonyl)-N 1 -(1-phenyl-1H-1,2,4-triazol-5-yl)isophthalic acid diamide, 2-chloro-N 3 ,N 3 -dimethyl-4-(methylsulfonyl)-N 1 -(1-methyl-1H-tetrazol-5-yl)isophthalic acid diamide, 2-chloro-N 3 -methoxy-N 3 -methyl-4-(methylsulfonyl)-N1 -(1-Methyl-1H-tetrazol-5-yl)isophthalamide, 2-chloro-N 1 -(1-Ethyl-1H-tetrazol-5-yl)-N 3 ,N 3 -Dimethyl-4-(methylsulfonyl)isophthalamide, 2-chloro-N 1 -(1-Ethyl-1H-tetrazol-5-yl)-N 3 -Methoxy-N 3 -Methyl-4-(methylsulfonyl)isophthalamide, 2-chloro-N 3 ,N 3 -Dimethyl-4-(methylsulfonyl)-N 1 -(1-Phenyl-1H-tetrazol-5-yl)isophthalamide, 2-chloro-N 3 -Methoxy-N 3 -Methyl-4-(methylsulfonyl)-N 1 -(1-Phenyl-1H-tetrazol-5-yl)isophthalamide.

[0005] WO2013 / 017559A1 discloses the following isophthalamides having herbicidal activity:

[0006] 2-Chloro-N 1 -[1-(2-Methoxyethyl)-1H-tetrazol-5-yl]-N 3 ,N 3 -Dimethyl-4-(methylsulfonyl)isophthalamide, 2-chloro-N 3 -Methoxy-N 1 -[1-(2-Methoxyethyl)-1H-tetrazol-5-yl]-N 3 -Methyl-4-(methylsulfonyl)isophthalamide.

[0007] In particular, the isophthalamides disclosed therein always have a tertiary amide group. However, the isophthalamides known from these documents do not always have sufficient herbicidal efficacy and / or compatibility with crop plants.

[0008] It has been found that, compared with the isophthalamides known in the prior art, the isophthalamides having tertiary amide groups at the 2- and 4-positions of the benzene ring have better properties. Accordingly, the present invention provides an isophthalamide of formula (I) or a salt thereof

[0009]

[0010] wherein the symbols and superscripts are defined as follows:

[0011] Q is Q 1 or Q 2 ,

[0012]

[0013] W is nitrogen,

[0014] 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,

[0015] Y is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 1 O or R 2 (O) n S, provided that when X is chlorine, Y is not methylsulfonyl,

[0016] Z 1 , Z 2 each independently is the following group substituted by s groups selected from halogen, cyano, R 1 C(O), R 1 OC(O), R 1 O and R 2 (O) n S: (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,

[0017] or

[0018] each is a group 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) and which is substituted on the following groups: phenyl, benzyl, heterocycle or heterocycle-(C1-C6)-alkyl,

[0019] or

[0020] Z 1 and Z 2 together with the nitrogen atom to which they are attached form a four-, five-, six- or seven-membered heterocycle which contains n other heteroatoms selected from O, S and N as ring atoms and which is substituted by m groups selected from the following: carbonyl, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy,

[0021] R 1 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl,

[0022] R 2 is (C1-C6)-alkyl,

[0023] R x is (C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or phenyl,

[0024] m is 0, 1, 2 or 3,

[0025] n is 0, 1 or 2,

[0026] s is 0, 1, 2, 3 or 4.

[0027] In formula (I) and all of the following formulas, alkyl groups having more than two carbon atoms can be straight-chain or branched-chain. Alkyl groups are, 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 groups are, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-2-yl and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methylbut-3-yn-1-yl. The multiple bond can be located at any position in each of the unsaturated groups. Cycloalkyl is a carbocyclic saturated ring system having three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Halogen-substituted alkyl means a straight-chain or branched-chain alkyl group in which some or all of the hydrogen atoms in these groups can be replaced by halogen atoms, for example C1-C2-haloalkyl, such as 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.

[0028] Halogen represents fluorine, chlorine, bromine or iodine.

[0029] A heterocyclic group (heterocyclyl) is a 4-, 5- or 6-membered cyclic group which contains at least one heteroatom selected from N, O, S in addition to carbon atoms, and is saturated, unsaturated, partially saturated or heteroaromatic, and may be unsubstituted or substituted, in which case the bonding point is located on 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-tetrahydropyridin-2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-1- or 2- or 3- or 4-yl; 2,3-dihydropyridin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridin-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-tetrahydrothienyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-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-imidazol-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl;Hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyrazin-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-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-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolan-2- or 4- or 5-yl; 1,3-dioxolen-2- or 4-yl (1,3-dioxol-2-or 4-yl); 1,3-dioxan-2- or 4- or 5-yl (1,3-dioxan-2-or4-or 5-yl); 4H-1,3-dioxin-2- or 4- or 5- or 6-yl (4H-1,3-dioxin-2-or 4-or 5-or6-yl); 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl (1,3-dithiolan-3-or 4-yl); 3H-1,2-dithiol-3- or 4- or 5-yl (3H-1,2-dithiol-3-or 4-or 5-yl); 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- 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-dithiolan-2-or 4-or 5-yl; 4H-1,3-dithiolan-2-or 4-or 5-or 6-yl; isoxazolin-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-oxazin-2-or 3-or 4-or 5-or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl; 5,6-dihydro-2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3-or 4-or 5-or 6-yl; 2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl; 6H-1,2-oxazin-3-or 4-or 5-or 6-yl; 4H-1,2-oxazin-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-oxazin-2-or 3-or 4-or 5-or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2-or 3-or 4-or 5-or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2-or 4-or 5-or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2-or 4-or 5-or 6-yl; 2H-1,3-oxazin-2-or 4-or 5-or 6-yl; 6H-1,3-oxazin-2-or 4-or 5-or 6-yl; 4H-1,3-oxazin-2-or 4-or 5-or 6-yl; morpholin-2-or 3-or 4-yl; 3,4-dihydro-2H-1,4-oxazin-2-or 3-or 4-or 5-or 6-yl; 3,6-dihydro-2H-1,4-oxazin-2-or 3-or 5-or 6-yl; 2H-1,4-oxazin-2-or 3-or 5-or 6-yl; 4H-1,4-oxazin-2-or 3-yl; isothiazolin-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-thiazolin-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-thiazinan-2- or 3- or 4- or 5- or 6-yl (1,3-thiazinan-2-or 3-or 4-or5-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-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4,2-dioxolan-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl;

[0030] Depending on the nature of the substituents and their mode of attachment, the compounds of formula (I) can exist as stereoisomers. For example, if there is one or more asymmetrically substituted carbon atoms, enantiomers and diastereoisomers are possible. When n is 1 (sulfoxide), stereoisomers also occur. The stereoisomers can be obtained from the mixtures obtained in the preparation process by conventional separation methods (e.g., 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 covered by formula (I) but not explicitly defined.

[0031] The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine or pyridine; and hydroxides, carbonates and bicarbonates of ammonium, alkali metals or alkaline earth metals, especially 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, such as a metal salt, especially an alkali metal salt or an alkaline earth metal salt, especially sodium and potassium salts, or an ammonium salt, a salt with an organic amine or a quaternary ammonium salt, for example, having the formula [NRR′R″R″′] +Salts of cations, where 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, such as (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkylsulfoxonium salts.

[0032] The compounds of formula (I) can form salts by the reaction of an adduct of a suitable inorganic acid or organic acid (such as an inorganic acid, such as HCl, HBr, H2SO4, H3PO4 or HNO3; or an organic acid, such as a carboxylic acid like 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 (such as an amino, alkylamino, dialkylamino, piperidinyl, morpholinyl or pyridyl group). Thus, these salts contain the conjugate base of the acid as the anion.

[0033] Preferred are compounds of general formula (I), where the symbols and subscripts have the following meanings:

[0034] Q is Q 1 ,

[0035] R x is Me, Et, Pr, i-Pr, c-Pr, (CH2)2OMe or Ph,

[0036] W is nitrogen,

[0037] X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, c-Pr, OMe, OEt, SMe, SEt, CH2OMe or CH2SMe,

[0038] Y is halogen, halo-(C1-C6)-alkyl, OMe, SMe, S(O)Me, SO2Me, SEt, S(O)Et or SO2Et,

[0039] with the condition that when X is chlorine, Y is not methylsulfonyl,

[0040] Z 1 ,Z 2 independently are (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2c-Pr, halo-(C1-C6)-alkyl, (CH2)2OMe, (CH2)2SMe, allyl, propargyl, C(O)CH3, C(O)-c-Pr, CO2Me, CO2Et, Ph, (2-Me)Ph, (4-F)Ph, CH2C(O)NMe2, CH2C(O)Me or CH2C(O)cPr.

[0041] or Z 1 and Z 2 are together (CH2)3 or (CH2)4,

[0042] or W, Z 1 and Z 2 are both pyrazol-1-yl or L-proline-1-yl ethyl ester.

[0043] Particularly preferred are the compounds of general formula (I), in which the symbols and subscripts have the following meanings:

[0044] Q is Q 1 ,

[0045] R x is Me, Et or Pr,

[0046] W is nitrogen,

[0047] X is F, Cl, Br, I, Me, Et, c-Pr, OMe, SMe, SEt or CH2OMe,

[0048] Y is F, Cl, Br, I, SMe, S(O)Me, SO2Me, CHF2, CF3 or C2F5,

[0049] with the proviso that when X is chlorine, Y is not methylsulfonyl,

[0050] Z 1 , Z 2 are independently Me, Et, c-Pr, CH2-c-Pr, CH2CHF2, CH2CF3, C(O)CH3, C(O)c-Pr, CO2Me, CO2Et, Ph or (2-Me)Ph, or Z 1 and Z 2 are both (CH2)4,

[0051] or W, Z 1 and Z 2 are both pyrazol-1-yl or L-proline-1-yl ethyl ester,

[0052] R 1 is Me, Et or c-Pr,

[0053] R 2 is Me.

[0054] The compounds of the present invention can be prepared, for example, by the method detailed in Scheme 1 of WO 2012 / 028579 A1. The corresponding benzoyl chlorides or their parent benzoic acids are in principle known and can be prepared, for example, by the methods described in WO1998 / 029383, EP418013, EP282944, JP2000319251 or JP02045448. The preparation methods of the compounds of the present invention are further illustrated by the examples described below.

[0055] Work-up of the respective reaction mixtures is generally effected by known methods, for example by crystallization, aqueous extraction treatment, by chromatography or by a combination of these methods.

[0056] 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 is one or more asymmetrically substituted carbon atoms, enantiomers and diastereoisomers are possible. When n is 1 (sulfoxide), stereoisomers also occur. The stereoisomers can be obtained from the mixtures obtained in the preparation 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 invention also relates to all stereoisomers and mixtures thereof embraced by general formula (I) which are not explicitly defined.

[0057] The collection of compounds of formula (I) and / or their salts which can be synthesized by the abovementioned reactions can also be prepared in parallel fashion, in which case it can be effected manually, semi-automatically or fully automatically. For example, the reaction, work-up or purification of the product and / or intermediate can be effected automatically. In general, this is understood to mean, for example, the methods described by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Günther Jung).

[0058] The compounds of formula (I) (and / or their salts) according to the invention, hereinafter collectively referred to as "the compounds of the invention", have excellent herbicidal activity against economically important broad-spectrum monocotyledonous and dicotyledonous annual harmful plants.

[0059] The invention thus also provides a method for controlling unwanted plants or regulating plant growth (preferably in a plant crop), in which one or more compounds of the invention are applied to the plants (for example, harmful plants, such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (for example, grains, seeds or vegetative propagules, such as tubers or shoot parts with buds) or the area on which the plants grow (for example, a cultivation area). The compounds of the invention can be applied, for example, before sowing (if appropriate, also by incorporation into the soil), pre-emergence or post-emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds of the invention are given below, although the listing is not intended to impose a limitation to specific species.

[0060] Monocotyledonous harmful plant genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0061] Dicotyledonous weed genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, 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.

[0062] When the compounds of the present invention are applied to the soil surface before emergence, either the emergence of weed seedlings is completely prevented or the weeds grow until they have reached the cotyledon stage, but then growth stops.

[0063] If the active ingredient is applied to the green parts of the plants after emergence, growth stops after treatment and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, thereby eliminating the competition from weeds harmful to the crop plants at a very early stage and in a lasting manner in this way.

[0064] The compounds of the invention can be selective in useful plant crops or can be applied as non-selective herbicides.

[0065] By virtue of their herbicidal and plant growth-regulating properties, the active ingredients can also be used for controlling harmful plants in known or as yet undeveloped transgenic plant crops. In general, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain active ingredients used in the agrochemical industry (in particular certain herbicides), resistance to plant diseases or the pathogens of plant diseases (such as certain insects or microorganisms such as fungi, bacteria or viruses). Other specific characteristics relate, for example, to the yield, quality, storability, composition and specific constituents of the harvest. For example, there are transgenic plants with an increased starch content or an altered starch quality known, or those transgenic plants with a different fatty acid composition in the harvest. Other specific properties consist in the tolerance or resistance to abiotic stress factors (such as heat, cold, drought, salt and UV radiation).

[0066] Preferably, the compounds of formula (I) according to the invention or their salts are used in transgenic crops of economically important useful plants and ornamental plants. The compounds of formula (I) can be used as herbicides in useful plant crops which are resistant to the phytotoxic action of the herbicide or which have been genetically modified to be resistant to the phytotoxic action of the herbicide.

[0067] Conventional methods for producing new plants with improved properties compared to existing plants consist, for example, of traditional cultivation methods and the generation of mutants. Alternatively, new plants with altered properties can be generated by means 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 synthesized in plants (for example WO 92 / 011376A, WO 92 / 014827A, WO 91 / 019806A), specific herbicides of the glufosinate type (see, for example, EP 0242236 A, EP 0242246 A), the glyphosate type (WO 92 / 000377A), the sulfonylurea type (EP 0257993A, US 5,013,659) or transgenic crop plants resistant to combinations or mixtures of these herbicides by "gene stacking", for example transgenic crop plants with the trade name or designation OptimumTM GATTM (glyphosate ALS tolerance), such as maize or soybean.

[0068] - Transgenic crop plants that can produce Bacillus thuringiensis toxins (Bt toxins), such as cotton, which enable the plants to resist specific pests (EP 0142924 A, EP 0193259 A),

[0069] - Transgenic crop plants with an improved fatty acid composition (WO 91 / 013972A),

[0070] - Genetically modified crop plants with new components or secondary metabolites - such as new phytoalexins, which enhance disease resistance - (EP 0309862 A, EP0464461 A),

[0071] - Genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP0305398 A),

[0072] - Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming"),

[0073] - Transgenic crop plants characterized by higher yields or better quality,

[0074] - Transgenic crop plants characterized by, for example, the combination of the above new properties ("gene stacking").

[0075] In principle, a large number of molecular biological techniques for the preparation of new transgenic plants with improved properties are known; 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).

[0076] For such genetic manipulations, nucleic acid molecules capable of generating mutations or sequence alterations by recombinant DNA sequences can be introduced into plasmids. By means of standard methods, for example, base exchanges, removal of parts of sequences or addition of natural or synthetic sequences can be carried out. To ligate 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 ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

[0077] For example, the generation of plant cells with reduced gene product activity can be achieved by the following methods: by expressing at least one corresponding antisense RNA, sense RNA for co-suppression, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above gene product. For this purpose, DNA molecules containing the entire coding sequence of the gene product (including any possible flanking sequences) can first be used, as well as DNA molecules containing only a part of the coding sequence, in which case these parts must be long enough to produce an antisense effect in the cell. DNA sequences highly homologous but not identical to the coding sequence of the gene product can also be used.

[0078] When expressing a nucleic acid molecule in a plant, the synthesized protein can be localized in any desired compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be linked, for example, to a DNA sequence that ensures localization in the 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). The nucleic acid molecule can also be expressed in the organelles of the plant cell.

[0079] Transgenic plant cells can be regenerated into whole plants by known techniques. In principle, the transgenic plants can be plants of any desired plant variety, i.e., not only monocotyledonous plants but also dicotyledonous plants. Transgenic plants with altered properties can be obtained by overexpression, repression or inhibition of homologous (= native) genes or gene sequences, or by expression of heterologous (= foreign) genes or gene sequences.

[0080] The compounds (I) of the present invention can preferably be used in transgenic crops that are 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 isoxazoles and similar active ingredients; or any desired combination of these active ingredients.

[0081] The compounds of the present invention can be particularly preferably used in transgenic crop plants that are resistant to combinations of glyphosate and glufosinate, glyphosate and sulfonylureas or imidazolinones. Most preferably, the compounds of the present invention can be used in transgenic crop plants such as those with the trade name or name OptimumTM GATTM (glyphosate ALS - tolerant), such as corn or soybeans.

[0082] When the active ingredients of the present invention are used in transgenic crops, they not only have an impact on harmful plants observed in other crops, but often have a specific impact on the specific transgenic crops to which they are applied, 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 the herbicides to which the transgenic crops are resistant, and an impact on the growth and yield of the transgenic crop plants.

[0083] Accordingly, the present invention also relates to the use of a compound of formula (I) according to the present invention as a herbicide for controlling harmful plants in transgenic crop plants.

[0084] The compounds of the present invention can be used in conventional formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules. Accordingly, the present invention also provides a herbicidal and plant growth regulating composition containing a compound of the present invention.

[0085] The compounds of the present invention can be formulated in various ways according to their required 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 oil-in-water emulsions and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed dressings, granules for broadcasting and soil application, granules in the form of fine particles (GR), spray granules, absorbent granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are in principle known and are described, for example, in Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Chapter 7, C. Hanser Verlag, Munich, 4th Edition, 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Edition, 1979, G. Goodwin Ltd., London.

[0086] 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 N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Edition, J.Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide", 2nd Edition, Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Chapter 7, C.Hanser Verlag Munich, 4th Edition, 1986.

[0087] Based on these formulations, combinations with other active ingredients such as insecticides, acaricides, herbicides, fungicides and with safeners, fertilizers and / or growth regulators can also be prepared, for example in the form of ready-to-use formulations or tank mixes.

[0088] Binding and compatible substances in the form of a mixed formulation or a tank mix for the compounds of the present invention are, for example, known active ingredients based on the inhibition of, for example, the following substances: acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, 5-enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, 4-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as known from, for example, 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 which can be combined with the compounds of the present invention are, for example, the following active substances, where the active ingredients are represented by their “common name” or chemical name or code number according to the International Organization for Standardization (ISO). It always includes all use forms, for example acids, salts, esters and all isomeric forms such as stereoisomers and optical isomers, even if they are not explicitly mentioned.

[0089] Examples of such herbicidal mixed compatibility substances are:

[0090] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, 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, chlorfenprop, 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, 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-ethylhexyl, 2,4-D - isobutyl ester, 2,4-D - isooctyl ester, 2,4-D - isopropylammonium, 2,4-D - potassium, 2,4-D - triisopropanolammonium, and 2,4-D - triethanolamine, 2,4-DB, 2,4-DB - butyl ester, 2,4-DB - dimethylammonium, 2,4-DB - isooctyl ester, 2,4-DB - potassium, and 2,4-DB - sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, 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, dinitramine, dinoterb, diphenamid, diquat, diquat - dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron - methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen - ethylEthoxysulfuron, 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, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, 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, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e., (2,4-dichlorophenoxy)ethyl 1-(dimethoxyphosphoryl)ethyl ester), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyrImazethapyr-immonium, Imazosulfuron, Indanofan, Indaziflam, Iodosulfuron, Iodosulfuron-methyl-sodium, Ioxynil, Ioxynil-octanoate, Ioxynil potassium and Ioxynil sodium, IpFencarbazone, Isoproturon, Isouron, Isoxaben, 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, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium, Mecoprop, Mecoprop-sodium and Mecoprop-butoxyethyl ester, Mecoprop-P, Mecoprop-P-butoxyethyl ester, Mecoprop-P-dimethylammonium, Mecoprop-P-2-ethylhexyl ester and Mecoprop-P-potassium, Mefenacet, Mefluidide, Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanate, Metobromuron, Metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, 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, norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, 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 (pyrazolate), 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-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523,SYP-249 (i.e., 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl ester), 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, 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, 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:

[0091]

[0092] Examples of plant growth regulators as possible mixed formulations are:

[0093] Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propanoic 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, 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-naphthaleneacetic acid, 2-naphthoxyacetic acid, nitrophenolate 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, uniconazole-P.

[0094] Safeners that can be used in combination with the compounds of formula (I) of the present invention and optionally in combination with other active ingredients (such as the pesticides, acaricides, herbicides, fungicides mentioned above), are preferably selected from:

[0095] S1) Compounds of formula (S1),

[0096]

[0097] wherein the symbols and subscripts have the following meanings:

[0098] n A is a natural number from 0 to 5, preferably from 0 to 3;

[0099] R A 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl;

[0100] W A is an unsubstituted or substituted divalent heterocyclic group selected from partially unsaturated or aromatic five-membered heterocycles 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 the group is selected from (W A 1 ) to (W A 4 );

[0101]

[0102] m A is 0 or 1;

[0103] R A 2 is OR A 3 、SR A 3 or NR A 3 R A 4 , or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and at most 3 heteroatoms (preferably selected from O and S), which is connected to the carbonyl group in (S1) through a nitrogen atom and is unsubstituted or substituted by (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably the formula OR A 3 、NHR A 4 or N(CH3)2, especially the formula OR A 3group;

[0104] R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0105] R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or a substituted or unsubstituted phenyl;

[0106] R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 wherein 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;

[0107] R A 6 R A 7 R A 8 are the same or different and are hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or a substituted or unsubstituted phenyl;

[0108] Preferably:

[0109] a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr-diethyl”), and related compounds as described in WO-A-91 / 07874;

[0110] b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and related compounds as described in EP-A-333131 and EP-A-269806;

[0111] c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and related compounds as described in, for example, EP-A-268554;

[0112] d) compounds of the triazolecarboxylic acid type (S1 d ), preferably compounds such as fenchlorazole (-ethyl ester), i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0113] e) compounds of the 5-benzyl-2-isoxazoline-3-carboxylic acid or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (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.

[0114] S2) quinoline derivatives of formula (S2)

[0115]

[0116] where the symbols and subscripts have the following meanings:

[0117] R B 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl;

[0118] n B is a natural number from 0 to 5, preferably from 0 to 3;

[0119] R B 2 is OR B 3 、SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and at most 3 heteroatoms (preferably selected from O and S), which is linked via the nitrogen atom to the carbonyl group in (S2), and which is unsubstituted or substituted by a group selected from (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably the group of the formula OR B 3 、NHR B 4 or N(CH3)2, especially the group of the formula OR B 3 ;

[0120] R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0121] R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl;

[0122] T B is an unsubstituted or (C1 or C2)-alkanediyl chain substituted by one or two (C1-C4)-alkyl groups or by [(C1-C3)-alkoxy]carbonyl;

[0123] Preferably:

[0124] a) a compound of the 8-quinolyloxyacetic acid type (S2 a ), preferably

[0125] (5-chloro-8-quinolyloxy)acetic acid 1-methylhexyl ester (“ cloquintocet-mexyl ”)(S2-1),

[0126] (5-Chloro-8-quinolyloxy)acetic acid 1,3-dimethylbut-1-yl ester (S2-2),

[0127] (5-Chloro-8-quinolyloxy)acetic acid 4-allyloxybutyl ester (S2-3),

[0128] (5-Chloro-8-quinolyloxy)acetic acid 1-allyloxyprop-2-yl ester (S2-4),

[0129] (5-Chloro-8-quinolyloxy)acetic acid ethyl ester (S2-5),

[0130] (5-Chloro-8-quinolyloxy)acetic acid methyl ester (S2-6),

[0131] (5-Chloro-8-quinolyloxy)acetic acid allyl ester (S2-7),

[0132] (5-Chloro-8-quinolyloxy)acetic acid 2-(2-propylideneiminooxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolyloxy)acetic acid 2-oxoprop-1-yl ester (S2-9), and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492 366, and (5-chloro-8-quinolyloxy)acetic acid (S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as described in WO-A-2002 / 34048;

[0133] b) Compounds of the (5-chloro-8-quinolyloxy)malonic acid type (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.

[0134] S3) Compounds of formula (S3)

[0135]

[0136] wherein the definitions of the symbols and superscripts are as follows:

[0137] R C 1 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;

[0138] R C 2 、RC 3 are 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, dioxolanyl-(C1-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R C 2 and R C 3 together form a substituted or unsubstituted heterocycle, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;

[0139] Preferably:

[0140] active ingredients of the dichloroacetamide type, which are generally used as pre-emergence safeners (soil-acting safeners), such as

[0141] "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" from Stauffer (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2),

[0142] "R-28725" from Stauffer (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3),

[0143] "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),

[0144] "PPG-1292" from PPG Industries (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5),

[0145] "DKA-24" from Sagro-Chem (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6),

[0146] "AD-67" or "MON 4660" from Nitrokemia or Monsanto (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7),

[0147] “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” from BASF ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydro-pyrrolo[1,2-a]pyrimidin-6-one) (S3-9),

[0148] “furilazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11).

[0149] S4) N-acylsulfonamides of formula (S4) and their salts,

[0150]

[0151] where the symbols and superscripts are defined as follows:

[0152] A D is SO2-NR D 3 -CO or CO-NR D 3 -SO2

[0153] X D is CH or N;

[0154] R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;

[0155] 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;

[0156] R D 3 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl;

[0157] R D 4is 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;

[0158] R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or a 3- to 6-membered heterocyclic group containing v D heteroatoms selected from nitrogen, oxygen and sulfur, where the last seven groups are substituted by v D substituents: 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;

[0159] R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where the last three groups are substituted by v D groups selected from halogen, hydroxy, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio, or

[0160] R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl group;

[0161] R D 7 is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two groups are substituted by v D substituents: 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;

[0162] n Dis 0, 1 or 2;

[0163] m D is 1 or 2;

[0164] v D is 0, 1, 2 or 3;

[0165] wherein, preferably, a compound of the N-acylsulfonamide type such as the following formula (S4 a ) is known, for example, from WO-A-97 / 45016

[0166]

[0167] wherein

[0168] R D 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two groups are substituted by v selected from the following D substituents: halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of the cyclic group, also including (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0169] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0170] m D is 1 or 2;

[0171] v D is 0, 1, 2 or 3;

[0172] and a compound of acylaminosulfonylbenzamide of the following formula (S4 b ) is known, for example, from WO-A-99 / 16744,

[0173]

[0174] for example, those compounds wherein

[0175] R D 5 = cyclopropyl and (R D 4 ) = 2-OMe (“cyprosulfamide”, S4-1),

[0176] R D 5 = cyclopropyl and (R D 4) = 5-Cl-2-OMe (S4-2),

[0177] R D 5 = ethyl and (R D 4 ) = 2-OMe (S4-3),

[0178] R D 5 = isopropyl and (R D 4 ) = 5-Cl-2-OMe (S4-4) and

[0179] R D 5 = isopropyl and (R D 4 ) = 2-OMe (S4-5)

[0180] and

[0181] the N-acylsulfamoylphenylurea-type compounds of formula (S4 c ), which are known, for example, from EP-A-365484,

[0182]

[0183] wherein

[0184] R D 8 and R D 9 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,

[0185] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3,

[0186] m D is 1 or 2;

[0187] for example

[0188] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (“metcamifen”, S4-6),

[0189] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0190] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

[0191] and

[0192] N-phenylsulfonylterephthalamide of formula (S4 d ), for example known from CN 101838227

[0193]

[0194] for example those compounds in which

[0195] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0196] m D is 1 or 2;

[0197] R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl.

[0198] Active ingredient (S5) from the group of hydroxyaromatic compounds and aromatic aliphatic carboxylic acid derivatives, for example

[0199] ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxybenzoic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0200] Active ingredient (S6) from the group of 1,2-dihydroquinoxalin-2-ones, for example

[0201] 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.

[0202] Compound of formula (S7), as described in WO-A-1998 / 38856

[0203]

[0204] The symbols and subscripts are defined as follows:

[0205] R E 1 and R E 2 are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro;

[0206] A E is COOR E 3 or COSR E 4

[0207] R E 3 and 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,

[0208] n E 1 is 0 or 1

[0209] n E 2 and n E 3 are independently 0, 1 or 2,

[0210] Preferably:

[0211] diphenylmethoxyacetic acid,

[0212] ethyl diphenylmethoxyacetate,

[0213] methyl diphenylmethoxyacetate (CAS Registry No. 41858-19-9) (S7-1).

[0214] S8) A compound of formula (S8) as described in WO-A-98 / 27049,

[0215]

[0216] wherein

[0217] X F is CH or N,

[0218] n F if X F = N, is an integer from 0 to 4 and

[0219] If X F =CH, then it is an integer from 0 to 5,

[0220] 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,

[0221] R F 2 is hydrogen or (C1-C4)-alkyl,

[0222] 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,

[0223] Preferably, the compound wherein

[0224] X F is CH,

[0225] n F is an integer from 0 to 2,

[0226] R F 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy,

[0227] R F 2 is hydrogen or (C1-C4)-alkyl,

[0228] 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,

[0229] or a salt thereof.

[0230] S9) An active ingredient (S9) from 3-(5-tetrazolylcarbonyl)-2-quinolones, such as

[0231] 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 95855-00-8), as described in WO-A-1999 / 000020.

[0232] S10) A compound of formula (S10 a ) or (S10 b )

[0233] as described in WO-A-2007 / 023719 and WO-A-2007 / 023764

[0234]

[0235] wherein

[0236] R G 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,

[0237] Y G and Z G each independently represent O or S,

[0238] n G is an integer from 0 to 4,

[0239] R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halobenzyl,

[0240] R G 3 is hydrogen or (C1-C6)-alkyl.

[0241] S11) An active ingredient of the oxime-imino compound type (S11), which is known as a seed dressing agent, for example

[0242] "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against the damage of metolachlor,

[0243] "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against the damage of metolachlor, and

[0244] "Cyometrinil" or "CGA-43089", ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum against the damage of metolachlor.

[0245] Active ingredients (S12) from isothiochromanones, such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS registration number 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.

[0246] One or more compounds from group (S13):

[0247] "Naphthalic anhydride" (1,8-naphthalic anhydride) (S13-1), which is known as a seed dressing safener in maize against the damage of thiocarbamate herbicides.

[0248] "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice.

[0249] "Flurazole" (benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener in millet / sorghum against the damage of alachlor and metolachlor.

[0250] "CL 304415" from American cyanamid (CAS registration number 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), which is known as a safener in maize against the damage of imidazolinones.

[0251] "MG 191" from Nitrokemia (CAS registration number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), which is known to be used as a safener in maize.

[0252] "MG 838" from Nitrokemia (CAS registration number 133993-74-5) (allyl 1-oxa-4-azaspiro[4.5]decane-4-dithiocarboxylate) (S13-6).

[0253] "Disulfoton" (O,O-diethyl S-2-ethylthioethyl dithiophosphate) (S13-7),

[0254] "Dietholate" (O,O-diethyl O-phenyl thiophosphate) (S13-8),

[0255] "Mephenate" (4-chlorophenyl N-methylcarbamate) (S13-9).

[0256] S14) Active ingredients that, in addition to having a herbicidal effect on harmful plants, also have a safener effect on crop plants such as rice, for example

[0257] "Dimepiperate" or "MY-93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for use in rice to protect against damage by the herbicide molinate,

[0258] "Daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for use in rice to protect against damage by the herbicide flazasulfuron,

[0259] "Cumyluron" = "JC-940" (3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087270), which is known as a safener for use in rice to protect against damage by some herbicides,

[0260] "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for use in rice to protect against damage by some herbicides,

[0261] "CSB" from Kumiai (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS registration number 54091-06-4), which is known as a safener for use in rice to protect against damage by some herbicides.

[0262] S15) Compounds of formula (S15) or their tautomers

[0263]

[0264] as described in WO-A-2007 / 131861 and WO-A-2008 / 131860

[0265] wherein,

[0266] R H 1is a (C1-C6)-haloalkyl group, and

[0267] R H 2 is hydrogen or halogen, and

[0268] R H 3 and R H 4 are independently hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl,

[0269] wherein the last three groups are each unsubstituted or substituted by one or more groups selected from: 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 heterocyclic group,

[0270] or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring, (C4-C6)-cycloalkenyl fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring,

[0271] wherein the last four groups are each unsubstituted or substituted by one or more groups selected from: 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 heterocyclic group,

[0272] or

[0273] R H 3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy, and

[0274] R H 4is hydrogen or (C1-C4)-alkyl, or

[0275] R H 3 and R H 4 together with the directly linked nitrogen atom represent a 4- to 8-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 heterocycle is unsubstituted or substituted by one or more groups selected from: halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0276] S16) Active compounds which are used primarily as herbicides but have a safener action on crop plants, such as

[0277] (2,4-dichlorophenoxy)acetic acid (2,4-D),

[0278] (4-chlorophenoxy)acetic acid,

[0279] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

[0280] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

[0281] (4-chloro-o-tolyloxy)acetic acid (MCPA),

[0282] 4-(4-chloro-o-tolyloxy)butyric acid,

[0283] 4-(4-chlorophenoxy)butyric acid,

[0284] 3,6-dichloro-2-methoxybenzoic acid (dicamba),

[0285] ethyl 1-(ethoxycarbonyl)-3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

[0286] Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.

[0287] Wettable powders are preparations that can be uniformly dispersed in water and contain, in addition to the active ingredient and in addition to diluents or inert substances, surfactants (wetting agents, dispersants) of the ionic and / or non-ionic type, such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare the wettable powder, the active herbicidal ingredient is finely ground in conventional equipment such as hammer mills, air blast mills and jet mills and is mixed simultaneously or subsequently with formulation aids.

[0288] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (such as 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 non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers such as fatty acid polyethylene glycol esters, alkylaryl polyethylene glycol ethers, fatty alcohol polyethylene glycol 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.

[0289] Dusting products are obtained by grinding the active ingredient together with a finely divided solid, such as talc, natural clays (such as kaolin, bentonite and pyrophyllite) or diatomaceous earth.

[0290] Suspension concentrates can be water-based or oil-based. They can be prepared by wet grinding methods, for example, using a commercially available bead mill and optionally adding surfactants such as those listed above for other formulation types.

[0291] Emulsions, such as oil-in-water emulsions (EW), can be prepared using aqueous organic solvents and optionally surfactants such as those listed above, for example, for other formulation types, with the aid of, for example, stirrers, colloid mills and / or static mixers.

[0292] Granules can be prepared by spraying the active ingredient onto granular inert materials capable of adsorption or by applying a concentrate of the active ingredient to the surface of a carrier material (such as sand, kaolinite or granular inert materials) with the aid of an adhesive (such as polyvinyl alcohol, sodium polyacrylate or mineral oil). Suitable active compounds can also be granulated in a manner conventional for the preparation of fertilizer granules - if desired in admixture with fertilizers.

[0293] Wettable granules are generally prepared by conventional methods such as spray drying, fluidized bed granulation, pan granulation, mixing with a high-speed mixer and extrusion without solid inert materials.

[0294] 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; J. E. Browning, "Agglomeration", Chemical and Engineering 1967, page 147 et seq.; "Perry's Chemical Engineer's Handbook", 5th Edition, McGraw Hill, New York 1973, page 8-57.

[0295] For other details on formulations of crop protection compositions, see, for example, G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, "Weed Control Handbook", 5th Edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0296] Agrochemical formulations generally contain from 0.1% to 99% by weight, in particular from 0.1% to 95% by weight, of the compounds according to the invention. In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, the balance to 100% being composed of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active ingredient can be from about 1% to 90% by weight and preferably from 5% to 80% by weight. Formulations in powder form contain from 1% to 30% by weight of the active ingredient, preferably generally from 5% to 20% by weight of the active ingredient; sprayable solutions contain from about 0.05% to 80% by weight, preferably from 2% to 50% by weight, of the active ingredient. In the case of wettable granules, the active ingredient content depends in part on whether the active ingredient is in liquid or solid form, and on the granulation aids, fillers, etc. used. In wettable granules, the content of the active ingredient is, for example, from 1 to 95% by weight, preferably from 10 to 80% by weight.

[0297] In addition, the mentioned active ingredient preparations optionally contain various conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and reagents that affect pH and viscosity.

[0298] Based on these preparations, combinations with other pesticidal active substances (such as insecticides, acaricides, herbicides, fungicides) can also be prepared, as well as combinations with safeners, fertilizers and / or growth regulators, for example in the form of finished preparations or tank mixes.

[0299] For application, if appropriate, the preparations in commercial form are diluted in a conventional manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-type preparations, granules for soil application or broadcast granules and sprayable solutions are generally not further diluted with other inert substances before application.

[0300] The required application rate of the compounds of formula (I) and their salts varies according to external conditions (such as especially temperature, humidity and the type of herbicide used). It can vary within a wide range, for example the amount of active substance is from 0.001 to 10.0 kg / ha or more, but it is preferably from 0.005 to 5 kg / ha, more preferably from 0.01 to 1.5 kg / ha, and even more preferably from 0.05 to 1 kg / ha. This applies both to pre-emergence application and post-emergence application.

[0301] The carrier is a natural or synthetic, organic or inorganic substance with which the active ingredient is mixed or combined to obtain better applicability, especially for application to plants or plant parts or seeds. Solid or liquid carriers, which are usually inert, should be suitable for use in agriculture. 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 silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils, vegetable oils and their derivatives. Mixtures of such carriers can also be used. Useful solid carriers for granules include: for example, crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic cereals, and granules of organic materials such as sawdust, coconut husks, corn cobs and tobacco stalks.

[0302] Suitable liquefied gas fillers or carriers are liquids that are gaseous at standard temperature and atmospheric pressure, such as aerosol propellants, such as halogenated hydrocarbons, or butane, propane, nitrogen and carbon dioxide.

[0303] In the preparation, thickeners can be used, such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids, such as cephalin and lecithin, as well as synthetic phospholipids. Other additives can be mineral oils and vegetable oils.

[0304] When the filler used is water, organic solvents can also be used as cosolvents, for example. Useful liquid solvents are essentially: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils and vegetable oils, alcohols such as butanol or ethylene glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

[0305] The compositions of the present invention can additionally contain other components, such as surfactants. Useful surfactants are emulsifiers and / or foam formers, dispersants or wetting agents having ionic or non-ionic properties, or mixtures of these surfactants. Examples thereof are polyacrylates, lignosulfonates, phenolsulfonates or naphthalenesulfonates, condensates 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 alkyl taurates), phosphates of polyethoxylated alcohols or polyethoxylated phenols, fatty acid esters of polyols and derivatives of compounds containing sulfate, sulfonate and phosphate groups, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysates, lignosulfite waste liquors and methyl cellulose. If one of the active ingredients and / or one of the inert carriers is insoluble in water and is applied in water, then a surfactant must be present. The proportion of the surfactant is 5 to 40% by weight of the composition of the present invention. Dyes can be used, 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, as well as micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0306] If appropriate, there may also be present other additional components, such as protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, chelating agents, complexing agents. Generally speaking, the active ingredient can be combined with any solid or liquid additive commonly used for formulation purposes. Generally, the compositions and formulations of the present invention contain the active ingredient in an amount of 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, and most preferably 10% to 70% by weight. The active ingredient or the composition itself of the present invention can be used, or according to their respective physical and / or chemical properties, their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold fog concentrates, warm fog concentrates, capsule granules, fine granules, flowable concentrates for seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, large granules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, pesticidally coated seeds, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, sprayable powders, soluble powders, powders and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, natural products and synthetic substances impregnated with the active ingredient, and microcapsules in polymeric substances and seed coating materials, as well as ULV cold fog and warm fog formulations.

[0307] The mentioned formulations can be prepared in a manner known per se, for example, by mixing the active ingredient with at least one commonly used filler, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, optionally desiccant and UV stabilizer, and optionally dyes and pigments, defoamer, preservative, secondary thickener, tackifier, gibberellin and other processing aids.

[0308] The compositions of the present invention include not only the formulations that are ready for use and can be applied to plants or seeds using suitable equipment, but also the commercially available concentrates that must be diluted with water before use.

[0309] The active ingredient of the present invention can exist in itself or in its (commercially available standard) formulation, or in the use form prepared as a mixture of these formulations with other (known) active ingredients (such as insecticides, attractants, disinfectants, fungicides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or chemical pheromones).

[0310] The treatment of plants and plant parts with the active ingredients or compositions of the present invention is effected directly by conventional treatment methods or by acting on their surrounding environment, habitat or storage space, for example by dipping, spraying, atomizing, irrigation, evaporation, dusting, fogging, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigation, and in the case of propagation material, especially in the case of seeds, also by dry seed treatment, wet seed treatment, slurry treatment, coating, coating with one or more layers, etc. The active ingredient can also be applied by the ultra-low volume method or the active ingredient formulation or the active ingredient itself can be injected into the soil.

[0311] 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 treating seeds with these active ingredients and compositions protects not only the seeds themselves but also the plants obtained after emergence from damage by phytopathogenic fungi. In this way, direct treatment of the crop at the time of sowing or shortly after sowing can be dispensed with.

[0312] It is also considered advantageous that the active ingredients or compositions of the present invention can also be used in particular for transgenic seeds, in which case the plants growing from the seeds are capable of expressing proteins against pests. By the expression of the proteins alone (such as insecticidal proteins), treating such seeds with the active ingredients or compositions of the present invention can lead to the control of certain pests. Surprisingly, in this case a further synergistic effect can be observed, which additionally increases the effectiveness of preventing pest infestation.

[0313] The compositions of the present invention are suitable for protecting the seeds of any plant variety used in agriculture, greenhouses, forests or horticulture and viticulture. In particular, the seeds are those of cereals (such as wheat, barley, rye, triticale, sorghum / millet and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, kidney beans, coffee, sugar beets (such as sugar beet and fodder beet), peanuts, oilseed rape, poppies, olives, coconuts, cocoa, sugar cane, tobacco, vegetables (such as tomatoes, cucumbers, onions and lettuce), turf and ornamental plants (see also below). The treatment of seeds of cereals (such as wheat, barley, rye, triticale and oats), maize and rice is of particular importance.

[0314] As described below, treating transgenic seeds with the active ingredients or compositions of the present invention is of particular significance. 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 can be derived from microorganisms of, for example, the following genera: Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The heterologous gene is preferably derived from a species of the genus Bacillus, in which case the gene product is effective against the European corn borer and / or the western corn rootworm. The heterologous gene is more preferably derived from Bacillus thuringiensis.

[0315] In the context of the present invention, the compositions of the present invention are applied to the seeds alone or in a suitable formulation. Preferably, the seeds are treated in a state where they are stable enough not to be damaged during the treatment process. Generally, the seeds can be treated at any time between harvest and sowing. Customarily, seeds separated from plants and free of cobs, husks, stems, epidermis, hairs or pulp are used. 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 have been dried, treated with water and then dried again can also be used.

[0316] Generally, when treating seeds, it is necessary to ensure that the amount of the composition of the present invention and / or other additives applied to the seeds is selected such that the germination of the seeds is not impaired and the plants grown therefrom are not harmed. This must be ensured especially in the case of active ingredients that may exhibit phytotoxic effects at certain application rates.

[0317] The compositions of the present invention can be applied directly, i.e., without containing any other components and without dilution. Generally, it is preferred to apply the compositions to the seeds in a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US

[0318] 4,272,417A, US 4,245,432 A, US 4,808,430, US 5,876,739, US

[0319] 2003 / 0176428A1, WO 2002 / 080675 A1, WO 2002 / 028186 A2.

[0320] The active ingredients used according to the present invention can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, pastes or other coating compositions for seeds, as well as ULV formulations.

[0321] These preparations are prepared in a known manner by mixing the active ingredient with conventional additives such as conventional fillers and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, binders, gibberellins, and water.

[0322] The dyes that can be present in the seed dressing preparations used according to the invention are all dyes that are commonly used for such purposes. Pigments slightly soluble in water or dyes soluble in water can be used. Examples include dyes known by the names Rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1.

[0323] The useful wetting agents that can be present in the seed dressing preparations used according to the invention are all substances that promote wetting and are commonly used in preparations of agrochemical active ingredients. Alkylnaphthalenesulfonates such as diisopropylnaphthalenesulfonate or diisobutylnaphthalenesulfonate can preferably be used.

[0324] The suitable dispersants and / or emulsifiers that can be present in the seed dressing preparations used according to the invention are all nonionic, anionic, and cationic dispersants that are commonly used in preparations of agrochemical active ingredients. Nonionic dispersants or anionic dispersants or mixtures of nonionic dispersants or anionic dispersants can preferably be used. Suitable nonionic dispersants especially include ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers, and triphenylvinylphenol polyglycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants are especially lignosulfonates, polyacrylates, and arylsulfonate-formaldehyde condensates.

[0325] The defoamers that can be present in the seed dressing preparations used according to the invention are all foam-inhibiting substances that are commonly used in preparations of agrochemical active ingredients. Silicone defoamers and magnesium stearate can preferably be used.

[0326] The preservatives that can be present in the seed dressing preparations used according to the invention are all substances that can be used for such purposes in agrochemical compositions. Examples include dichlorobenzene and benzyl alcohol hemiformal.

[0327] The secondary thickeners that can be present in the seed dressing preparations used according to the invention are all substances that can be used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic derivatives, xanthan gum, modified clays, and finely divided silica.

[0328] The useful binders that can be present in the seed dressing preparations used according to the invention are all conventional binders that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and methylcellulose (tylose).

[0329] The seed dressing preparation used according to the present invention can be used directly or after prior dilution with water to treat various different seeds, including the seeds of transgenic plants. In this case, the interaction with the substances formed by expression can also produce additional synergistic effects.

[0330] In order to treat seeds with the seed dressing preparation that can be used according to the present invention or with the preparation prepared therefrom by adding water, useful devices are all mixing devices that can generally be used for seed dressing. Specifically, the seed dressing method is to put the seeds into a mixer, add a specific required amount of the seed dressing preparation itself or the seed dressing preparation diluted with water in advance, and mix them until the preparation is evenly distributed on the seeds. If appropriate, a drying operation is carried out after this.

[0331] The active ingredients of the present invention having good plant compatibility, beneficial constant temperature toxicity and good environmental compatibility are suitable for protecting plants and plant organs, to increase the harvest yield and improve the quality of the harvested crops. They can preferably be used as crop protection agents. They are active against generally sensitive and resistant species and are active against all or specific developmental stages.

[0332] Plants that can be treated according to the present invention include the following major crop plants: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (e.g., Canola), Brassica rapa, Brassica juncea (e.g., field mustard), Brassica carinata, rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet, and sorghum, triticale, flax, grapes, and various fruits and vegetables of various plant groups such as Rosaceae sp. (e.g., pomes such as apples and pears, and drupes such as apricots, cherries, almonds, and peaches, and berries such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae 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 grapefruits), Solanaceae sp. (e.g., tomatoes, potatoes, peppers, eggplants), Liliaceae sp., Compositae sp. (e.g., lettuce, artichokes, and chicories - including root chicory, Belgian endive, or common chicory), Umbelliferae 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, pak choi, kohlrabi, radishes, horseradish, watercress, and Chinese cabbage), Leguminosae sp. (e.g., peanuts, peas, and soybeans - e.g., kidney beans and fava beans), Chenopodiaceae sp.)(e.g., Swiss chard, fodder beet, spinach, beetroot), Malvaceae (e.g., okra), Asparagaceae (e.g., asparagus); useful and ornamental plants in gardens and forests; and, in each case, genetically modified forms of these plants.

[0333] As mentioned above, all plants and parts thereof can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those plants and parts thereof obtained by traditional biotechnological breeding techniques (e.g., hybridization or protoplast fusion) are treated. In another preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) obtained by genetic engineering methods (if appropriate, in combination with traditional methods) and parts thereof are treated. The terms "part" or "part of a plant" or "plant part" have been explained above. According to the invention, it is particularly preferred to treat plants of commercially available conventional plant cultivars or those plants that are in use. Plant cultivars are understood to mean plants having new properties ("characteristics") that have been bred by conventional breeding, mutagenesis or recombinant DNA techniques. They can be cultivars, varieties, biotypes and genotypes.

[0334] The treatment method according to the invention can be used to treat genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that has been provided or assembled outside the plant, and after introduction of this gene into the nuclear genome, chloroplast genome or mitochondrial genome, it confers new or improved agronomic or other characteristics on the transformed plant due to the expression of the protein or polypeptide of interest or another gene present in the plant, or another gene present in the plant that is downregulated or switched off (e.g., by antisense technology, co-suppression technology or RNAi technology [RNA interference]). A heterologous gene located in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is called a transformation or transgenic event.

[0335] Depending on the plant species or plant cultivar, their location and growth conditions (soil, climate, vegetation period, feeding), the treatment according to the invention can also result in supra-additive ("synergistic") effects. For example, the following effects that go beyond the actually expected effects are possible: a reduction in the application rate of the active ingredients and compositions that can be used according to the invention and / or a broadening of the activity spectrum and / or an enhancement of the efficacy, better plant growth, an increase in the tolerance to high or low temperatures, an increase in the tolerance to drought or to water or soil salinity, an improvement in the flowering performance, easier harvesting, accelerated ripening, a higher harvesting yield, larger fruits, a higher plant height, greener leaf color, earlier flowering, a higher quality and / or nutritional value of the harvested product, a higher sugar concentration in the fruits, better storage stability and / or better processability of the harvested product.

[0336] At certain application rates, the active ingredient combinations of the present invention can also have a fortifying effect on plants. Thus, they are suitable for mobilizing the defense systems of plants against attacks by unwanted phytopathogenic fungi and / or microorganisms and / or viruses. This may be one of the reasons for the enhanced activity, for example, antifungal activity of the compositions of the present invention. Plant fortifying (resistance-inducing) substances are to be understood herein as meaning those substances or combinations of substances that are capable of stimulating the defense systems of plants in such a way that when subsequently inoculated with unwanted phytopathogenic fungi, the treated plants exhibit a substantial degree of resistance to these unwanted phytopathogenic fungi. Thus, the substances of the present invention can be used to protect plants from the mentioned pathogens for a specific period of time after treatment. After treating the plants with the active ingredient, the period during which protection is achieved is generally extended from 1 to 10 days, preferably from 1 to 7 days.

[0337] Plants and plant cultivars preferably treated according to the present invention include all plants (whether obtained by breeding and / or biotechnological means) having genetic material that confers particularly advantageous and useful properties on these plants.

[0338] Also preferably, plants and plant cultivars treated according to the present invention are resistant to one or more biotic stress factors, meaning that these plants have better defense capabilities against animal and microbial pests (such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses, and / or viroids).

[0339] Examples of nematode-resistant plants are described, for example, in the following US 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.

[0340] Plants and plant cultivars that can also be treated according to the present invention are those that are resistant to one or more abiotic stress factors. Abiotic stress conditions can 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 shade avoidance.

[0341] Plants and plant varieties that can also be treated according to the present invention are those plants characterized by enhanced yield characteristics. The enhanced yield in such plants can be the result of, for example, improved plant physiology, growth, and development, such as water use efficiency, water holding efficiency, improved nitrogen utilization, enhanced carbon assimilation, improved photosynthesis, increased germination rate, and accelerated maturation. Yield can also be affected by improved plant architecture (under both stress and non-stress conditions), which includes but is not limited to: earlier flowering, flowering control for hybrid seed production, seedling vigor, plant size, number of internodes and internode spacing, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed quality, enhanced seed plumpness, reduced seed dispersal, reduced pod shattering, and lodging resistance. Other yield characteristics include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability, and better storage stability.

[0342] Plants that can be treated according to the present invention are hybrid plants that already exhibit characteristics of heterosis or hybrid vigor, which typically result in higher yields, vigor, better health, and resistance to biotic and abiotic stress factors. Such plants are usually produced by crossing an inbred male-sterile parent line (female hybrid parent) with another inbred male-fertile parent line (male hybrid parent). Hybrid seeds are usually harvested from the male-sterile plants and sold to growers. Male-sterile plants can sometimes (e.g., in maize) be produced by detasseling (i.e., mechanically removing the male reproductive organs or male flowers), but more typically, male sterility is the result of genetic determinants in the plant genome. In such cases, especially when the seeds are the desired product harvested from hybrid plants, it is usually beneficial to ensure that male fertility in the hybrid plants is fully restored, which contain genetic determinants causing male sterility. This can be achieved by ensuring that the male hybrid breeding parent has an appropriate fertility restoration gene that can restore male fertility in hybrid plants containing genetic determinants causing male sterility. The genetic determinants of male sterility can be located in the cytoplasm. For example, instances of cytoplasmic male sterility (CMS) in Brassica species have been documented. However, the genetic determinants 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. A particularly useful method for obtaining male-sterile plants is described in WO 89 / 10396, where, for example, ribonucleases such as Bacillus ribonuclease (barnase) are selectively expressed in the tapetal cells of the stamen. Then, fertility can be restored by expressing a ribonuclease inhibitor such as Bacillus ribonuclease inhibitor (Barstar) in the tapetal cells.

[0343] Plants or plant cultivars that can be processed according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are herbicide-tolerant plants, i.e., plants that are tolerant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such herbicide tolerance.

[0344] Herbicide-tolerant plants are, for example, plants that are tolerant to glyphosate, i.e., plants that are tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate by various methods. Thus, for example, glyphosate-tolerant plants can be obtained by transforming plants with a gene 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), genes encoding petunia EPSPS (Shah et al., 1986, Science 233, 478-481), tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or Eleusine EPSPS (WO 01 / 66704). It can also be a mutant EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding glyphosate oxidoreductase. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding glyphosate acetyltransferase. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally occurring mutations of the above genes. Plants expressing EPSPS genes that confer glyphosate tolerance have been described. Plants expressing other genes such as decarboxylase genes that confer glyphosate tolerance have been described.

[0345] Other herbicide-resistant plants are, for example, plants that are tolerant to herbicides that inhibit glutamine synthase (such as bilanafos, phosphinothricin or glufosinate). Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of glutamine synthase that is resistant to inhibition. An example of such an effective detoxifying enzyme is the enzyme encoding phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces). Plants expressing exogenous phosphinothricin acetyltransferase have been described.

[0346] Other herbicide-tolerant plants are also plants that have been made tolerant to herbicides that inhibit hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenase is the enzyme that catalyzes the reaction in which p-hydroxyphenylpyruvate (HPP) is converted into homogentisic acid. Plants tolerant to HPPD inhibitors can be transformed with genes encoding naturally occurring HPPD-resistant enzymes or genes encoding mutant or chimeric HPPD enzymes, as described in WO 96 / 38567, WO 99 / 24585, WO 99 / 24586, WO2009 / 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 that can form homogentisic acid, even though the HPPD inhibitors inhibit the native HPPD enzyme. Such plants are described in WO 99 / 34008 and WO 02 / 36787. In addition to genes encoding HPPD-resistant enzymes, the tolerance of plants to HPPD inhibitors can also be improved by transforming plants with genes encoding prephenate dehydrogenase, as described in WO2004 / 024928. Furthermore, plants can be made more tolerant to HPPD inhibitors by inserting genes encoding enzymes that metabolize or degrade HPPD inhibitors (such as CYP450 enzymes) into the genome of the plant (see WO 2007 / 103567 and WO 2008 / 150473).

[0347] Other herbicide-resistant plants are plants that are tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylureas, imidazolinones, triazolopyrimidines, pyrimidyloxy(thio)benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the known ALS enzyme (also called 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 described. Other plants tolerant to sulfonylureas and imidazolinones have also been described.

[0348] Other plants tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutation, by selection in cell culture in the presence of the herbicide or by mutagenic breeding (see, for example, for soybean US 5,084,082, for rice WO97 / 41218, for sugar beet US 5,773,702 and WO 99 / 057965, for lettuce US 5,198,599 or for sunflower WO 01 / 065922).

[0349] Plants or plant varieties that can also be processed according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are transgenic insect-resistant plants, i.e., plants that are resistant to the infestation of certain target insects. Such plants can be obtained by genetic transformation or by screening plants containing mutations that confer such insect resistance.

[0350] As used herein, the term "transgenic insect-resistant plant" includes any plant containing at least one transgene comprising a coding sequence encoding:

[0351] 1) An insecticidal crystal protein of Bacillus thuringiensis or an insecticidal portion thereof, such as those compiled by Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807-813), updated by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:

[0352] http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / ) and the insecticidal crystal proteins or insecticidal portions thereof, such as proteins of the Cry protein classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa or Cry3Bb or insecticidal portions thereof (e.g., EP-A 1999141 and WO 2007 / 107302), or proteins encoded by synthetic genes as described in U.S. Patent Application 12 / 249,016; or

[0353] 2) A crystal protein of Bacillus thuringiensis or a portion thereof that is insecticidal in the presence of a second crystal protein or a portion thereof other than Bacillus thuringiensis, said second crystal protein or portion thereof being, for example, a binary toxin consisting of Cy34 and Cy35 crystal proteins (Nat. Biotechnol. 2001, 19, 668-72; Applied Environm. Microbiol. 2006, 71, 1765-1774) or a binary toxin consisting of a Cry1A or Cry1F protein and a Cry2Aa or Cry2Ab or Cry2Ae protein (U.S. Patent Application 12 / 214,022 and EP08010791.5); or

[0354] 3) Hybrid insecticidal proteins comprising parts of two different insecticidal crystal proteins of Bacillus thuringiensis, such as hybrids of the proteins of 1) above or hybrids of the proteins of 2) above, such as the Cry1A.105 protein produced by maize line (event) MON98034 (WO 2007 / 027777); or

[0355] 4) The proteins of any one of 1) to 3) above, in which some, particularly 1 to 10 amino acids, are replaced by another amino acid to obtain higher insecticidal activity against target insect species, and / or to extend the range of target insect species affected, and / or due to changes introduced into the coding DNA during cloning or transformation, such as the Cry3Bb1 protein in maize line MON863 or MON88017, or the Cry3A protein in maize line MIR604; or

[0356] 5) Insecticidal secreted proteins of Bacillus thuringiensis or Bacillus cereus, or insecticidal parts thereof, such as 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

[0357] 6) Secreted proteins of Bacillus thuringiensis or Bacillus cereus that are insecticidal in the presence of a second secreted protein of Bacillus thuringiensis or Bacillus cereus, such as the binary toxin composed of VIP1A and VIP2A proteins (WO 94 / 21795); or

[0358] 7) Hybrid insecticidal proteins comprising parts of different secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as hybrids of the proteins of 1) above or hybrids of the proteins of 2) above; or

[0359] 8) The proteins of any one of 5) to 7) above, in which some, particularly 1 to 10 amino acids, are replaced by another amino acid to obtain higher insecticidal activity against target insect species, and / or to extend the range of target insect species affected, and / or due to changes introduced into the coding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton line COT 102; or

[0360] 9) A secreted protein of Bacillus thuringiensis or Bacillus cereus, which has insecticidal activity in the presence of the crystal protein of Bacillus thuringiensis, such as a binary toxin composed of protein VIP3 and Cry1A or Cry1F (U.S. Patent Applications 61 / 126083 and 61 / 195019), or a binary toxin composed of VIP3 protein and Cry2Aa or Cry2Ab or Cry2Ae protein (U.S. Patent Application 12 / 214,022 and EP 08010791.5); or

[0361] 10) The protein according to point 9) above, some of which, in particular 1 to 10 amino acids, have been replaced by another amino acid to obtain higher insecticidal activity against the target insect species, and / or to expand the range of target insect species affected, and / or due to changes introduced into the coding DNA during cloning or transformation (while still encoding an insecticidal protein).

[0362] Of course, the insect-resistant transgenic plants used herein also include any plant containing a combination of genes encoding any of the proteins in any of the above 1 to 10 categories. In one embodiment, the insect-resistant plant contains more than one transgene encoding any of the proteins in any of the above 1 to 10 categories, by using different proteins that have insecticidal activity against the same target insect species but have different modes of action (e.g., binding to different receptor binding sites in the insect) to expand the range of target insect species affected or to delay the development of insect resistance in the plant.

[0363] As used herein, "insect-resistant transgenic plant" additionally includes any plant containing at least one transgene that contains a sequence for producing double-stranded RNA, which prevents the growth of the pest after the pest consumes the food.

[0364] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the present invention are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such stress resistance. Particularly useful stress-tolerant plants include:

[0365] a) Plants containing a transgene capable of reducing the expression and / or activity of the poly(ADP-ribose) polymerase (PARP) gene in plant cells or plants;

[0366] b) Plants containing a transgene for enhancing stress tolerance that can reduce the expression and / or activity of the PARG-encoding gene in plants or plant cells;

[0367] c) Plants containing a transgene conferring enhanced stress tolerance, said transgene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinate mononucleotide adenylyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.

[0368] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention show alterations in the quantity, quality and / or storage stability of the harvested product and / or alterations in the properties of specific constituents of the harvested product, for example:

[0369] 1) Transgenic plants synthesizing modified starch, the physicochemical properties of which, in particular the amylose content or the amylose / amylopectin ratio, degree of branching, average chain length, side-chain distribution, viscosity behavior, gel strength, starch granule particle size and / or starch granule morphology, are altered compared to the starch synthesized in wild-type plant cells or plants, such that the modified starch is better suited for specific uses.

[0370] 2) Transgenic plants synthesizing non-starch carbohydrate polymers, or transgenic plants synthesizing non-starch carbohydrate polymers with altered properties compared to non-genetically modified wild-type plants. Examples are: plants producing polyfructans, especially inulin and fructan types, plants producing α-1,4-glucans, plants producing α-1,6-branched α-1,4-glucans, and plants producing alternan.

[0371] 3) Transgenic plants producing hyaluronic acid.

[0372] 4) Transgenic plants or hybrid plants, for example onions with specific properties such as "high soluble solids content", "low pungency" (LP) and / or "long-term storage" (LS).

[0373] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants with altered fiber properties, such as cotton plants. These plants can be obtained by genetic transformation or by screening plants containing mutations conferring such altered fiber properties, including the following plants:

[0374] a) Plants such as cotton plants containing a variant of the cellulose synthase gene;

[0375] b) Plants such as cotton plants containing a variant of the rsw2 or rsw3 homologous nucleic acid, for example cotton plants with increased sucrose phosphate synthase expression;

[0376] c) Plants such as cotton plants with increased sucrose synthase expression;

[0377] 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 a fiber-selective β-1,3-glucanase;

[0378] e) Plants such as cotton plants, having fibers with altered reactivity, for example by expressing an N-acetylglucosamine transferase gene including nodC and a chitin synthase gene.

[0379] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants having altered oil composition characteristics, such as oilseed rape or related Brassica plants. Such plants can be obtained by genetic transformation or by screening plants containing mutations that confer such altered oil properties, and include:

[0380] a) Plants that produce oil with a high oleic acid content, such as oilseed rape plants;

[0381] b) Plants that produce oil with a low linolenic acid content, such as oilseed rape plants;

[0382] c) Plants that produce oil with a low saturated fatty acid content, such as oilseed rape plants.

[0383] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants such as potatoes, which are, for example, virus-resistant to potato virus Y (strains SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (e.g., the RB gene), or which exhibit reduced cold-induced sweetening (carrying the gene Nt-Inh, II-INV) or which exhibit a dwarf phenotype (A-20 oxidase gene).

[0384] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants having altered seed shattering characteristics, such as oilseed rape or related Brassica plants. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such altered characteristics, and include plants having delayed or reduced seed shattering, such as oilseed rape.

[0385] Particularly useful transgenic plants that can be processed according to the present invention are plants having a transformed line or combination of transformed lines that are the subject of a non-regulated status application granted or pending with the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) in the United States. Information related thereto is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), for example, through the website

[0386] http: / / www.aphis.usda.gov / brs / not_reg.html. At the filing date of the present application, applications with the following information have been approved or are pending with APHIS:

[0387] - Application: The identification number of the application. Technical descriptions of the transformed lines can be found in the specific application documents available through the application number on the APHIS website. These descriptions are hereby incorporated by reference.

[0388] - Extension of application: Refers to a request to expand the scope or term of an earlier application.

[0389] - Agency: The name of the person who submitted the application.

[0390] - Regulated article: The plant species involved.

[0391] - Transgenic phenotype: The trait conferred on the plant by the transformed line.

[0392] - Transformed line or pedigree: The name of the line (sometimes also called a pedigree) for which non-regulated status is requested. - APHIS documents: Various documents published by APHIS regarding the application, or various documents that can be obtained from APHIS upon request.

[0393] Particularly useful transgenic plants that can be processed according to the present invention are plants that contain one or more genes encoding one or more toxins, such as transgenic plants sold under the following trade names: YIELD (e.g., corn, cotton, soybeans), (e.g., corn), (e.g., corn), (e.g., corn), (e.g., corn), (cotton), (cotton), Nucotn (cotton), (e.g., corn), and (potato). Examples of herbicide-tolerant plants include corn varieties, cotton varieties, and soybean varieties obtained under the following trade names: Roundup (glyphosate-tolerant, e.g. maize, cotton, soybean), Liberty (phosphinothricin-tolerant, e.g. oilseed rape), (imidazolinone-tolerant) and (sulfonylurea-tolerant), e.g. maize. Herbicide-resistant plants (plants with herbicide tolerance bred in a conventional manner) that may be mentioned include varieties sold under the trade name (e.g. maize).

[0394] Particularly useful genetically modified plants that can be treated according to the invention are plants containing a transformed line or a combination of transformed lines, and these are listed in the databases of, for example, a number of national or regional regulatory authorities (see, for example, http: / / gmoinfo.jrc.it / gmp_browse.aspx and

[0395] http: / / cera-gmc.org / index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit).

[0396] The active ingredients or compositions of the present invention can also be used for the protection of materials, to protect industrial materials from unwanted microorganisms such as fungi and insects and damage.

[0397] In addition, the compounds of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

[0398] In the present context, industrial materials are understood to mean non-biological materials that have been prepared for use in industry. For example, industrial materials protected from microbial alteration or damage by the active ingredients of the present invention can be adhesives, sizes, paper, wallpaper and cardboard, textiles, carpets, leather, wood, paints and plastic products, cooling lubricants and other materials that can be infected or damaged by microorganisms. The range of materials to be protected also includes components of production plants and buildings, such as cooling water circuits, cooling and heating systems, and ventilation and air-conditioning systems, which can be damaged by the reproduction of microorganisms. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood. The active ingredients or compositions of the present invention can prevent adverse effects such as decay, decomposition, discoloration, decolorization or the formation of mold. In addition, the compounds of the present invention can be used to protect objects in contact with salt water or brackish water (especially ship hulls, screens, fishing nets, buildings, mooring equipment and signal systems) from fouling.

[0399] The method according to the invention for controlling unwanted fungi can also be used for protecting stored goods. In the present context, "stored goods" are understood to mean natural substances of plant or animal origin or processed products of natural origin which require long-term protection. Stored goods of plant origin, such as plants or parts of plants, such as stems, leaves, tubers, seeds, fruits, grains, can be protected after fresh harvesting or processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Stored goods also include unprocessed wood (such as construction timber, telegraph poles and fence posts) and wood in finished form (such as furniture). Stored goods of animal origin are, for example, raw hides, leather, furs and hairs. The active ingredients according to the invention can prevent adverse effects, such as decay, decomposition, discoloration, decoloration or the formation of mould.

[0400] 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 species of Blumeria, such as Blumeria graminis; species of Podosphaera, such as Podosphaera leucotricha; species of Sphaerotheca, such as Sphaerotheca fuliginea; species of Uncinula, such as Uncinula necator; diseases caused by rust pathogens, such as species of Gymnosporangium, such as Gymnosporangium sabinae; species of Hemileia, such as Hemileia vastatrix; species of Phakopsora, such as Phakopsora pachyrhizi or Phakopsora meibomiae; species of Puccinia, such as Puccinia recondita or Puccinia triticina; species of Uromyces, such as Uromyces appendiculatus; diseases caused by pathogens from oomycetes, such as species of Bremia, such as Bremia lactucae; species of Peronospora, such as Peronospora pisi or Peronospora brassicae; species of Phytophthora, such as Phytophthora infestans; species of Plasmopara, such as Plasmopara viticola; species of Pseudoperonospora, such as Pseudoperonospora humuli or Pseudoperonospora cubensis;Pythium species, such as Pythium ultimum; leaf blotch disease and leaf wilt disease caused by the following pathogens: such as Alternaria species, such as Alternaria solani; Cercospora species, such as Cercospora beticola; Cladiosporium species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium); Colletotrichum species, such as Colletotrichum lindemuthanium; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulate; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Microdochium species, such as Microdochium nivale;Mycosphaerella species, such as Mycosphaerella graminicola and Mycosphaerella 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 incarnate; Venturia species, such as Venturia inaequalis; root and stem diseases caused by the following pathogens: 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 basicola; ear and panicle diseases (including maize crops) caused by the following pathogens: for example, Alternaria species, such as Alternaria species; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea;Species of Fusarium, such as Fusarium culmorum; species of Gibberella, such as Gibberella zeae; species of Monographella, such as Monographella nivalis; species of Septoria, such as Septoria nodorum; diseases caused by smut fungi, such as species of Sphacelotheca, such as Sphacelotheca reiliana; species of Tilletia, such as Tilletia caries, Tilletia controversa; species of Urocystis, such as Urocystis occulta; species of Ustilago, such as Ustilago nuda, Ustilago nuda tritici Fruit rot diseases caused by the following pathogens: for example, species of Aspergillus, such as Aspergillus flavus; species of Botrytis, such as Botrytis cinerea; species of Penicillium, such as Penicillium expansum and Penicillium purpurogenum; species of Sclerotinia, such as Sclerotinia sclerotiorum; species of Verticillium, such as Verticillium alboatrum; Seed-borne and soil-borne rot and wilt diseases, as well as seedling diseases caused by the following pathogens: for example, species of Fusarium, such as Fusarium culmorum; species of Phytophthora (such as Phytophthora cactorum); species of Pythium (such as Pythium ultimum); species of Rhizoctonia, such as Rhizoctonia solani; species of Sclerotium, such as Sclerotium rolfsii;Cancerous diseases, galls and witches' brooms caused by the following pathogens: for example, Nectria species, such as Nectria galligena;

[0401] Wilting diseases caused by the following pathogens: for example, Monilinia species, such as Monilinia laxa;

[0402] Deformities of leaves, flowers and fruits caused by the following pathogens: for example, Taphrina species, such as Taphrina deformans; Degenerative diseases of woody plants caused by the following pathogens: for example, Esca species, such as Phaeomoniella chlamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea;

[0403] Diseases of flowers and seeds caused by the following pathogens: for example, Botrytis species (such as Botrytis cinerea); Diseases of plant tubers caused by the following pathogens: for example, Rhizoctonia species (such as Rhizoctonia solani), Helminthosporium species, such as Helminthosporium solani; Diseases caused by the following bacterial pathogens: for example, Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. lachrymans; Erwinia species, such as Erwinia amylovora.

[0404] The following soybean diseases can be preferentially controlled:

[0405] Fungal diseases of leaves, stems, pods, and seeds caused by the following pathogens, such as: Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum loeosporoides dematium var. truncatum), Septoria leaf spot (Septoria glycines), shot hole and leaf blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frog eye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), Rhizoctonia aerial parts, leaf blight and damping-off (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), Stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

[0406] Fungal diseases located at the roots and the base of the stem caused by the following pathogens, such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or blight, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), Phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora regata), Pythium rot (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 southern blight (Sclerotinia rolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0407] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. The active ingredient of the present invention preferably acts on fungi, in particular molds, fungi that discolor and damage wood (Basidiomycetes), as well as on slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, 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; Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.

[0408] In addition, the active ingredients of the present invention also have very good antifungal activity. They have a very broad antifungal activity spectrum, especially against dermatophytes (antimycotic), yeasts, molds, and dimorphic fungi (diphasic fungi) (e.g., against Candida species, such as Candida albicans, Candida glabrata), 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 listing of these fungi in no way constitutes a limitation of the fungal spectrum that can be controlled, but merely has an illustrative character.

[0409] Therefore, the active ingredients of the present invention can be used for medical and non-medical applications.

[0410] If appropriate, the compounds of the present invention can also be used as herbicides, safeners, growth regulators, or reagents for improving plant characteristics, or as microbicides, such as fungicides, antifungals, bactericides, virucides (including antiviroids), or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms) at certain concentrations or application rates. Depending on the circumstances, they can also be used as intermediates or precursors for synthesizing other active ingredients.

[0411] The following examples illustrate the present invention.

[0412] A. Chemical Examples

[0413] Synthesis of N 3 -ethyl-N 3 -2-dimethyl-N 1 -(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl) isophthalamide

[0414] Step 1: Preparation of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl) benzoic acid

[0415] At -70 °C within 60 minutes, to 15 g (43.5 mmol) of methyl 3-iodo-2-methyl-4-(trifluoromethyl)benzoate initially added in 400 ml of dry THF, 43.6 ml (56.6 mmol) of a 1.3 M i-PrMgCl / LiCl THF solution was added. The reaction solution was warmed to -30 °C and stirred for an additional 60 minutes at this temperature. Subsequently, it was cooled back to -70 °C, and gaseous CO2 was introduced. Thereafter - with continuous introduction of CO2 and monitoring of the reaction - the mixture was warmed to room temperature. After the conversion was complete, the reaction solution was degassed in an ultrasonic bath and then concentrated to dryness. The residue was dissolved in water, adjusted to pH 3 - 4 with 2N HCl, and extracted with dichloromethane. The organic phase was dried and concentrated. The residue was purified by column chromatography (HPLC, normal phase, gradient: ethyl acetate / n-heptane: 5% → 70% ethyl acetate). 9 g of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl)benzoic acid was obtained.

[0416] 1 1H-NMR (400 MHz, DMSO-d6): δ = 14.08 (br s, 1H); 7.94 (d, 1H); 7.77 (d, 1H); 3.89 (s, 3H); 2.46 (s, 3H).

[0417] Step 2: Preparation of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate

[0418] To 400 mg (1.52 mmol) of 3-(methoxycarbonyl)-2-methyl-6-(trifluoromethyl)benzoic acid initially added in 20 ml of dichloromethane, a few drops of dimethylformamide were added. Subsequently, at room temperature, 0.2 ml (2.28 mmol) of oxalyl chloride was added, and the reaction mixture was stirred at room temperature for 2 hours. After the mixture was concentrated, it was co-evaporated with toluene twice. The residue was dissolved in 5 ml of dichloromethane and added dropwise at 0 °C to a solution of 0.2 ml (2.28 mmol) of N-methylethylamine and 0.5 ml (3.05 mmol) of Hünig's base in 10 ml of dichloromethane. The reaction mixture was stirred at room temperature for 12 hours and then concentrated to dryness. The residue was purified by column chromatography (HPLC, normal phase, gradient: ethyl acetate / n-heptane: 10% → 70% ethyl acetate). 424 mg of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate was obtained.

[0419] 1H-NMR (400 MHz, DMSO-d6): δ = 7.93 (d, 1H); 7.77 (d, 1H); 3.89 (s, 3H); 3.59 (m, 1H, isomer 1), 3.43 (m, 1H, isomer 1); 3.06 (m, 1H, isomer 2); 2.99 (s, 3H, isomer 1); 2.98 (m, 1H, isomer 2); 2.66 (s, 3H, isomer 2); 2.36 (s, 3H); 1.13 (t, 3H, isomer 1); 0.99 (t, 3H, isomer 2).

[0420] Step 3: Preparation of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid

[0421] At room temperature, 89 mg (2.09 mmol) of sodium hydroxide solution in 3 ml of water was added dropwise to 424 mg (1.39 mmol) of methyl 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoate initially added in 10 ml of methanol. The reaction mixture was stirred at room temperature for 4 hours. Subsequently, the reaction mixture was concentrated to dryness, and the residue was dissolved in 20 ml of water. The mixture was adjusted to pH 3 - 4 with 2N HCl, the formed precipitate was filtered off and dried. 352 mg of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid was obtained.

[0422] 1 H-NMR (400 MHz, DMSO-d6): δ = 13.58 (br s, 1H); 7.90 (m, 1H); 7.73 (d, 1H); 3.60 (m, 1H, isomer 1); 3.42 (m, 1H, isomer 1); 3.05 (m, 1H, isomer 2); 3.00 (s, 3H, isomer 1); 2.98 (m, 1H, isomer 2); 2.66 (s, 3H, isomer 2); 1.13 (t, 3H, isomer 1); 0.99 (t, 3H, isomer 2).

[0423] Step 4: Preparation of N 3 -ethyl-N 3 -2-dimethyl-N 1 -(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)isophthalamide

[0424] At room temperature, 0.09 ml (1.03 mmol) of oxalyl chloride was added to 200 mg (0.69 mmol) of 3-[ethyl(methyl)carbamoyl]-2-methyl-4-(trifluoromethyl)benzoic acid initially added in 3 ml of pyridine and 104.9 mg (1.03 mmol) of 1-methyl-1H-tetrazol-5-amine. The reaction mixture was stirred at room temperature for 12 hours. Then 10 ml of water was added and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated to dryness. The residue was purified by column chromatography (HPLC, C18, gradient: acetonitrile / water (+0.05% trifluoroacetic acid), 20 / 80 → 100 / 0 in 30 minutes). 44 mg (together with mixed fractions) of N 3 -ethyl-N 3 -2-dimethyl-N 1 -(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)isophthalamide (Example No. 1-20).

[0425] The examples listed in the following table were prepared in a similar manner to the above method or could be obtained similarly to the above method. These compounds are very particularly preferred.

[0426] The abbreviations used herein mean:

[0427] Me = methyl, Bu = butyl, Et = ethyl, Pr = propyl, c = cyclo, Ph = phenyl

[0428] Table 1: Compounds of general formula (I) of the present invention, where Q is Q 1 , R x is methyl and the other substituents have the definitions given below.

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442] Table 2: Compounds of general formula (I) of the present invention, where Q is Q 1 , R x is ethyl, and the other substituents have the following definitions.

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456] Table 3: Compounds of general formula (I) of the present invention, where Q is Q 1 , R x is propyl, and the other substituents have the definitions given below.

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470] The NMR data of the numerous compounds of formula (I) of the present invention described in the above table are disclosed below for further characterization:

[0471] Example Nos. 1 - 19: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s); 7.85 (d, 1H); 7.81 (d, 1H); 4.01 (s, 3H); 3.04 (s, 3H); 2.74 (s, 3H); 2.29 (s, 3H);

[0472] Example Nos. 1 - 20: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.85 (d, 1H); 7.82 (d, 1H); 4.01 (s, 3H); 3.60 (m, 1H); 3.45 (m, 1H); 3.05 (m, 2H); 3.00 (s, 3H); 2.71 (s, 3H); 2.30 (s, 3H); 1.14 (t, 3H); 1.02 (t, 3H);

[0473] Example Nos. 1 - 21: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 7.84 (d, 1H); 7.80 (d, 1H); 4.01 (s, 3H); 2.98 (s, 3H); 2.88 (m, 1H); 2.31 (s, 3H); 0.81 (m, 2H); 0.47 (m, 2H);

[0474] Example Nos. 1 - 24: 1H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 7.89 (d, 1H); 7.85 (d, 1H); 6.30 (tt, 1H); 4.02 (s, 3H); 3.98 (m, 2H); 2.84 (s, 3H); 2.33 (s, 3H);

[0475] Example Nos. 1 - 31: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 7.85 (d, 1H); 7.81 (d, 1H); 4.01 (s, 3H); 3.56 (m, 1H); 3.45 (m, 1H); 3.06 (m, 2H); 2.32 (s, 3H); 1.16 (t, 3H); 1.01 (t, 3H);

[0476] Example Nos. 1 - 32: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 7.84 (d, 1H); 7.80 (d, 1H); 4.01 (s, 3H); 3.55 (m, 1H); 3.45 (m, 1H); 2.51 (m, 1H); 2.32 (s, 3H); 1.16 (t, 3H); 0.48 (m, 4H);

[0477] Example Nos. 1 - 40: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.78 (br s, 1H); 7.84 (d, 1H); 7.79 (d, 1H); 4.01 (s, 3H); 2.67 (m, 1H); 2.36 (m, 1H); 2.29 (s, 3H); 0.86 (m, 2H); 0.81 (m, 2H); 0.60 (m, 2H); 0.46 (m, 2H);

[0478] Example Nos. 1 - 50: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.80 (d, 1H); 7.66 (d, 1H); 6.89 (t, 1H); 4.00 (s, 3H); 3.05 (s, 3H); 2.74 (s, 3H); 2.28 (s, 3H);

[0479] Example Nos. 1 - 51: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.79 (d, 1H); 7.67 (d, 1H); 6.89 (t, 1H); 4.00 (s, 3H); 3.54 (m, 2H); 3.02 (s, 3H); 2.29 (s, 3H); 1.16 (t, 3H);

[0480] Example Nos. 1 - 59: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 7.80 (d, 1H); 7.68 (d, 1H); 6.86 (t, 1H); 4.01 (s, 3H); 3.59 (m, 1H); 3.47 (m, 1H); 3.07 (m, 2H); 2.31 (s, 3H); 1.19 (t, 3H); 0.99 (t, 3H);

[0481] Example Nos. 1 - 123: 1 1H-NMR (400 MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.00 (s, 2H); 4.02 (s, 3H); 3.04 (s, 3H); 2.78 (s, 3H);

[0482] Example Nos. 1 - 124: 1 1H-NMR (400 MHz, DMSO-d6): δ = 12.01 (br s, 1H); 8.00 (s, 2H); 4.02 (s, 3H); 3.58 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 3.01 (s, 3H); 2.76 (s, 3H); 1.14 (t, 3H); 1.07 (t, 3H);

[0483] Example Nos. 1 - 125: 1 1H-NMR (400 MHz, DMSO-d6): δ = 12.03 (br s, 1H); 8.00 (d, 2H); 4.01 (s, 3H); 3.00 (s, 3H); 2.60 (m, 1H); 0.82 (m, 1H); 0.72 (m, 1H); 0.50 (m, 2H);

[0484] Example Nos. 1 - 126: 1 1H-NMR (400 MHz, DMSO-d6): δ = 12.02 (br s, 1H); 8.00 (s, 2H); 4.02 (br s, 3H); 3.43 (m, 2H); 3.36 (m, 2H); 3.11 (s, 3H); 2.94 (2, 2H); 2.83 (s, 3H); 1.09 (m, 1H); 0.86 (m, 1H); 0.51 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0485] Example No. 1 - 128: 1 H-NMR(400MHz, DMSO-d6): δ = 12.038(br s, 1H); 8.04(br s, 2H); 6.27(tt, 1H); 4.02(s, 3H); 4.00(m, 2H); 2.89(s, 3H);

[0486] Example No. 1 - 135: 1 H-NMR(400MHz, DMSO-d6): δ = 12.03(br s, 1H); 8.00(br s, 2H); 4.02(t, 3H); 3.55(m, 1H); 3.46(m, 1H); 3.10(m, 2H); 1.16(t, 3H); 1.05(t, 3H);

[0487] Example No. 1 - 136: 1 H-NMR(400MHz, DMSO-d6): δ = 12.06(br s, 1H); 8.00(br s, 2H); 4.02(s, 3H); 3.64(br s, 1H); 3.53(m, 2H); 1.17(t, 3H); 0.71(m, 1H); 0.51(m, 3H);

[0488] Example No. 1 - 144: 1 H-NMR(400MHz, DMSO-d6): δ = 12.03(br s, 1H); 7.99(br s, 2H); 4.01(s, 3H); 2.68(m, 1H); 0.83(m, 5H); 0.52(m, 3H);

[0489] Example No. 1 - 152: 1 H-NMR(400MHz, DMSO-d6): δ = 12.01(br s, 1H); 8.00(s, 2H); 4.02(s, 3H); 3.51(m, 2H); 3.12(m, 1H); 3.02(m, 1H); 1.88(m, 4H);

[0490] Example No. 1 - 153: 1 H-NMR(400MHz, DMSO-d6): δ = 12.11(br s, 1H); 8.75(br s, 1H); 8.20(d, 1H); 8.14(d, 1H); 7.97(s, 1H); 6.81(br s, 1H); 4.01(s, 3H);

[0491] Example No. 1 - 154: 11H-NMR (400 MHz, DMSO-d6): δ = 11.98 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.01 (s, 3H); 3.05 (s, 3H); 2.78 (s, 3H);

[0492] Example No. 1-155: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.97 (br s, 1H); 7.93 (br d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.02 (s, 3H); 3.54 (m, 1H); 3.02 (m, 1H); 2.76 (s, 3H); 1.16 (t, 3H);

[0493] Example No. 1-156: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.99 (br s, 1H); 7.93 (d, 1H); 7.81 (d, 1H); 6.96 (t, 1H); 4.02 (s, 3H); 3.02 (s, 3H); 2.65 (m, 1H); 0.79 (m, 1H); 0.52 (m, 1H); 0.44 (m, 2H);

[0494] Example No. 1-159: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.99 (br s, 1H); 7.99 (d, 1H); 7.87 (d, 1H); 7.01 (t, 1H); 6.31 (tt, 1H); 4.02 (s, 3H); 3.98 (m, 2H); 2.88 (s, 3H);

[0495] Example No. 1-166: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.97 (br s, 1H); 7.94 (d, 1H); 7.82 (d, 1H); 4.02 (s, 3H); 3.59 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 1.18 (t, 3H); 1.04 (t, 3H);

[0496] Example No. 1-167: 1H-NMR (400 MHz, DMSO-d6): δ = 11.99 (br s, 1H); 7.92 (d, 1H); 7.82 (d, 1H); 6.94 (t, 1H); 4.01 (s, 3H); 3.73 (m, 1H); 3.32 (m, 1H); 2.68 (m, 1H); 1.20 (t, 3H); 0.69 (m, 1H); 0.57 (m, 1H); 0.42 (m, 2H);

[0497] Example No. 1-175: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.98 (br s, 1H); 7.92 (br s, 1H); 7.82 (d, 1H); 6.99 (t, 1H); 4.01 (s, 3H); 2.72 (m, 1H); 2.50 (m, 1H); 0.84 (m, 5H); 0.59 (m, 1H); 0.49 (m, 1H); 0.40 (m, 1H);

[0498] Example No. 1-191: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.87 (d, 1H); 7.72 (d, 1H); 4.00 (s, 3H); 3.05 (s, 3H); 2.82 (s, 3H);

[0499] Example No. 1-192: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.87 (d, 1H); 7.71 (d, 1H); 4.00 (s, 3H); 3.54 (m 2H); 3.02 (s, 3H); 1.17 (t, 3H);

[0500] Example No. 1-200: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.86 (d, 1H); 7.71 (d, 1H); 4.35 (q, 2H); 3.99 (s, 3H); 3.51 (m, 2H); 3.13 (m, 2H); 1.19 (t, 3H); 1.09 (t, 3H);

[0501] Example No. 1-395: 1H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.95 (d, 1H); 7.89 (d, 1H); 4.01 (s, 3H); 3.25 (s, 3H); 3.01 (s, 3H); 2.72 (s, 3H); 2.31 (s, 3H);

[0502] Example Nos. 1 - 398: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (s, 1H); 7.89 (d, 1H); 7.81 (d, 1H); 7.37 - 7.22 (m, 4H); 4.02 (s, 3H); 3.19 (s, 3H);

[0503] Example Nos. 1 - 399: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.96 (s, 1H); 7.86 (d, 1H); 7.82 (d, 1H); 7.38 - 7.25 (m, 3H); 4.00 (s, 3H); 3.09 (s, 3H); 2.34 (s, 3H);

[0504] Example Nos. 1 - 400: 1 H-NMR (400 MHz, DMSO-d6): δ = 12.04 (br s, 1H); 8.03 (m, 2H); 4.48 (m, 1H); 4.15 (q, 2H); 4.02 (t, 3H); 3.21 (m, 1H); 2.31 (m, 1H); 1.95 (m, 4H); 1.21 (t, 3H);

[0505] Example Nos. 1 - 401: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 7.87 (d, 1H); 7.83 (d, 1H); 4.56 (m, 1H); 4.16 (q, 2H); 4.02 (s, 3H); 3.21 (m, 1H); 3.08 (m, 1H); 2.48 (s, 3H); 2.31 (m, 1H); 1.90 (m, 2H); 1.23 (t, 3H);

[0506] Example Nos. 1 - 402: 11H-NMR (400 MHz, DMSO-d6): δ = 11.98 (br s, 1H); 8.01 (d, 1H); 7.72 (d, 1H); 7.00 (t, 1H); 4.60 (m, 1H); 4.21 (m, 2H); 4.02 (s, 3H); 3.28 (m, 1H); 3.29 (m, 1H); 2.38 (m, 1H); 1.98 (m, 1H); 1.91 (m, 2H); 1.25 (t, 3H);

[0507] Example No. 2-19: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.69 (br s, 1H); 7.84 (d, 1H); 7.81 (d, 1H); 4.36 (q, 2H); 3.04 (s, 3H); 2.74 (s, 3H); 2.29 (s, 3H); 1.48 (t, 3H);

[0508] Example No. 2-21: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 7.82 (d, 1H); 7.80 (d, 1H); 4.36 (q, 2H); 2.98 (s, 3H); 2.88 (m, 1H); 2.30 (s, 3H); 1.48 (t, 3H); 0.82 (m, 1H); 0.73 (m, 1H); 0.52 (m, 1H); 0.46 (m, 1H);

[0509] Example No. 2-31: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.70 (br s, 1H); 7.84 (d, 1H); 7.81 (d, 1H); 4.36 (q, 2H); 3.57 (m, 1H); 3.46 (m, 1H); 3.07 (m, 2H); 2.31 (s, 3H); 1.48 (t, 3H); 1.16 (t, 3H); 1.01 (t, 3H);

[0510] Example No. 2-32: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 7.83 (d, 1H); 7.80 (d, 1H); 4.36 (q, 2H); 3.55 (m, 1H); 3.45 (m, 1H); 2.51 (m, 1H); 2.32 (s, 3H); 1.48 (t, 3H); 1.16 (t, 3H); 0.51 (m, 4H);

[0511] Example No. 2-50: 11H-NMR (400 MHz, DMSO-d6): δ = 11.62 (br s, 1); 7.89 (d, 1H); 7.66 (d, 1H); 6.89 (t, 1H); 4.35 (q, 2H); 3.05 (s, 3H); 2.74 (s, 3H); 2.28 (s, 3H); 1.48 (t, 3H);

[0512] Example No. 2-51: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.62 (br s, 1H); 7.79 (d, 1H); 7.67 (d, 1H); 6.89 (t, 1H); 4.35 (q, 2H); 3.53 (m, 2H); 3.03 (s, 3H); 2.29 (s, 3H); 1.48 (t, 3H); 1.17 (t, 3H);

[0513] Example No. 2-59: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.63 (br s, 1H); 7.79 (d, 1H); 7.68 (d, 1H); 6.86 (t, 1H); 4.35 (q, 2H); 3.60 (m, 1H); 3.46 (m, 1H); 3.07 (m, 2H); 2.30 (s, 3H); 1.48 (t, 3H); 1.19 (t, 3H); 0.99 (s, 3H);

[0514] Example No. 2-123: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.04 (s, 3H); 2.79 (s, 3H); 1.48 (t, 3H);

[0515] Example No. 2-124: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 7.99 (s, 2H); 4.38 (q, 2H); 3.58 (m, 1H); 3.47 (m, 1H); 3.10 (m, 2H); 3.00 (s, 3H); 2.76 (s, 3H); 1.48 (t, 3H); 1.14 (t, 3H); 1.07 (t, 3H);

[0516] Example No. 2-125: 1H-NMR (400 MHz, DMSO-d6): δ = 11.94 (br s, 1H); 7.99 (d, 2H); 4.37 (q, 2H); 3.00 (s, 3H); 2.59 (m, 1H); 1.47 (t, 3H); 0.81 (m, 1H); 0.70 (m, 1H); 0.49 (m, 2H);

[0517] Example No. 2-126: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.44 (m, 1H); 3.35 (m, 1H); 3.11 (s, 3H); 2.94 (m, 2H); 2.83 (s, 3H); 1.48 (t, 3H); 1.08 (m, 1H); 0.86 (m, 1H); 0.50 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0518] Example No. 2-128: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.95 (br s, 1H); 8.04 (br s, 2H); 6.27 (tt, 1H); 4.38 (q, 2H); 3.98 (m, 2H); 2.89 (s, 3H); 1.48 (t, 3H);

[0519] Example No. 2-135: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 3.55 (m, 1H); 3.47 (m, 1H); 3.09 (m, 2H); 1.47 (t, 3H); 1.16 (t, 3H); 1.05 (t, 3H);

[0520] Example No. 2-136: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.94 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 3.05 (m, 1H); 3.48 (m, 1H); 3.00 (m, 1H); 1.49 (t, 3H); 1.18 (t, 3H); 0.70 (m, 2H); 0.51 (m, 2H);

[0521] Example No. 2-144: 11H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.99 (br s, 2H); 4.37 (q, 2H); 2.68 (m, 2H); 1.47 (t, 3H); 0.85 (m, 5H); 0.52 (m, 3H);

[0522] Example No. 2-152: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 8.00 (s, 2H); 4.38 (q, 2H); 3.51 (m, 2H); 3.12 (m, 1H); 3.04 (m, 1H); 1.88 (m, 4H); 1.48 (t, 3H);

[0523] Example No. 2-153: 1 1H-NMR (400 MHz, DMSO-d6): δ = 12.00 (br s, 1H); 8.75 (br s, 1H); 8.19 (d, 1H); 8.14 (d, 1H); 7.97 (s, 1H); 6.81 (br s, 1H); 4.36 (q, 2H); 1.47 (t, 3H);

[0524] Example No. 2-154: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.37 (q, 2H); 3.05 (s, 3H); 2.78 (s, 3H); 1.48 (t, 3H);

[0525] Example No. 2-155: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.87 (br s, 1H); 7.91 (br s, 1H); 7.82 (d, 1H); 6.98 (t, 1H); 4.37 (q, 2H); 3.53 (m, 1H); 3.02 (m, 1H); 2.76 (s, 3H); 1.47 (t, 3H); 1.16 (t, 3H);

[0526] Example No. 2-156: 11H-NMR (400 MHz, DMSO-d6): δ = 11.87 (br s, 1H); 7.92 (d, 1H); 7.80 (d, 1H); 6.96 (t, 1H); 4.37 (q, 2H); 3.02 (s, 3H); 2.67 (m, 1H); 1.48 (t, 3H); 0.80 (m, 1H); 0.52 (m, 1H); 0.43 (m, 2H);

[0527] Example No. 2 - 159: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 7.97 (d, 1H); 7.85 (d, 1H); 7.01 (t, 1H); 6.31 (tt, 1H); 4.38 (q, 2H); 3.98 (m, 2H); 2.88 (s, 3H); 1.48 (t, 3H);

[0528] Example No. 2 - 166: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.88 (br s, 1H); 7.93 (d, 1H); 7.82 (d, 1H); 6.95 (t, 1H); 4.37 (q, 2H); 3.58 (m, 1H); 3.48 (m, 1H); 3.10 (m, 2H); 1.48 (t, 3H); 1.18 (t, 3H); 1.04 (t, 3H);

[0529] Example No. 2 - 167: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.87 (br s, 1H); 7.92 (br s, 1H); 7.82 (d, 1H); 6.94 (t, 1H); 4.37 (q, 2H); 3.74 (m, 1H); 3.33 (m, 1H); 2.67 (m, 1H); 1.48 (t, 3H); 1.20 (t, 3H); 0.69 (m, 1H); 0.57 (m, 1H); 0.41 (m, 2H);

[0530] Example No. 2 - 175: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.90 (br s, 1H); 7.82 (d, 1H); 6.99 (t, 1H); 4.37 (q, 2H); 2.72 (m, 1H); 2.50 (m, 1H); 1.47 (t, 3H); 0.85 (m, 5H); 0.59 (m, 1H); 0.50 (m, 1H); 0.40 (m, 1H);

[0531] Example No. 2 - 191:1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 7.87 (d, 1H); 7.71 (d, 1H); 4.35 (q, 2H); 3.05 (s, 3H); 2.82 (s, 3H); 1.47 (t, 3H);

[0532] Example No. 2-192: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 7.87 (d, 1H); 7.70 (d, 1H); 4.36 (q, 2H); 3.54 (m, 2H); 3.02 (s, 3H); 1.47 (t, 3H); 1.17 (t, 3H);

[0533] Example No. 2-200: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.86 (d, 1H); 7.70 (d, 1H); 4.35 (q, 2H); 3.52 (m, 2H); 3.13 (m, 2H); 1.46 (t, 3H); 1.19 (t, 3H); 1.09 (t, 3H);

[0534] Example No. 2-340: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.00 (d, 1H); 7.92 (d, 1H); 7.00 (t, 1H); 4.60 (m, 1H); 4.38 (q, 2H); 4.20 (m, 2H); 3.28 (m, 1H); 3.19 (m, 1H); 2.37 (m, 1H); 1.99 (m, 1H); 1.92 (m, 2H); 1.49 (t, 3H); 1.25 (t, 3H);

[0535] Example No. 2-398: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.94 (br s, 1H); 8.02 (br s, 1H); 4.47 (m, 1H); 4.38 (m, 2H); 4.15 (m, 2H); 3.21 (m, 1H); 3.31 (m, 1H); 1.96 (m, 4H); 1.49 (t, 3H); 1.22 (t, 3H);

[0536] Example No. 3-123: 11H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.04 (s, 3H); 2.79 (s, 3H); 1.89 (m, 2H); 0.88 (t, 3H);

[0537] Example No. 3-124: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.59 (m, 1H); 3.46 (m, 1H); 3.10 (m 2H); 3.00 (s, 3H); 2.76 (s, 3H); 1.89 (m, 2H); 1.14 (t, 3H); 1.06 (t, 3H); 0.88 (t, 3H);

[0538] Example No. 3-126: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.99 (s, 2H); 4.33 (t, 2H); 3.45 (m, 1H); 3.35 (m, 1H); 3.11 (s, 3H); 2.94 (m, 2H); 2.83 (s, 3H); 1.89 (m, 2H); 1.08 (m, 1H); 0.88 (t, 3H); 0.85 (m, 1H); 0.51 (m, 4H); 0.32 (m, 2H); 0.13 (m, 2H);

[0539] Example No. 3-152: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.99 (s, 2H); 4.32 (t, 2H); 3.50 (m, 2H); 3.12 (m, 1H); 3.04 (m, 1H); 1.89 (m, 6H); 0.88 (t, 3H);

[0540] Example No. 3-153: 1 1H-NMR (400 MHz, DMSO-d6): δ = 11.98 (br s, 1H); 8.75 (s, 1H); 8.18 (d, 1H); 8.14 (d, 1H); 7.97 (s, 1H); 6.81 (s, 1H); 4.31 (t, 2H); 1.88 (m, 2H); 0.88 (t, 3H).

[0541] B. Formulation Examples

[0542] a) The dusting product is obtained by the following method: 10 parts by weight of the compound of formula (I) and / or its salt are mixed with 90 parts by weight of talc as an inert substance, and the mixture is ground in a hammer mill.

[0543] b) The wettable powder which is easily dispersible in water is obtained by the following method: 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 lignosulfonate, and 1 part by weight of sodium oleoylmethyl taurate as a wetting agent and dispersant are mixed, and the mixture is ground in a pinned-disk mill.

[0544] c) The dispersion concentrate which is easily dispersible in water is obtained by the following method: 20 parts by weight of the compound of formula (I) and / or its salt are mixed with 6 parts by weight of alkylphenol polyglycol ether ( Triton X207), 3 parts by weight of isotridecyl alcohol polyglycol ether (8EO), and 71 parts by weight of paraffin mineral oil (boiling range, for example, about 255 °C to higher than 277 °C), and the mixture is ground in a friction ball mill to a fineness of less than 5 microns.

[0545] d) The emulsifiable concentrate is obtained by the following method: 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 are mixed.

[0546] e) The water-dispersible granule is obtained by the following method:

[0547] Mix the following substances

[0548] 75 parts by weight of the compound of formula (I) and / or its salt,

[0549] 10 parts by weight of calcium lignosulfonate,

[0550] 5 parts by weight of sodium dodecyl sulfate,

[0551] 3 parts by weight of polyvinyl alcohol, and

[0552] 7 parts by weight of kaolin,

[0553] The mixture is ground in a pinned-disk mill and granulated by spraying water as a granulating liquid in a fluidized bed.

[0554] f) The water-dispersible granule is obtained by the following method:

[0555] Homogenize and pre-grind the following substances in a colloid mill

[0556] 25 parts by weight of the compound of formula (I) and / or its salt,

[0557] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,

[0558] 2 parts by weight of sodium oleoylmethyltaurate,

[0559] 1 part by weight of polyvinyl alcohol,

[0560] 17 parts by weight of calcium carbonate and

[0561] 50 parts by weight of water,

[0562] Subsequently, the mixture was ground in a ball mill, and the resulting suspension was atomized and dried in a spray tower through a single-phase nozzle.

[0563] C. Biological Examples

[0564] Abbreviations for harmful plants mean:

[0565] ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides

[0566] AVEFA Avena fatua AMARE Amaranthus retroflexus

[0567] CYPES Cyperus esculentus DIGSA Digitaria sanguinalis

[0568] ECHCG Echinochloa crus-galli HORMU Hordeum murinum

[0569] LOLMU Lolium multiflorum LOLRI Lolium rigidum

[0570] MATIN Matricaria inodora PHBPU Pharbitis purpurea

[0571] POLCO Polygonum convolvulus SETVI Setaria viridis

[0572] STEME Stellaria media VERPE Veronica persica

[0573] VIOTR Pansy (Viola tricolor)

[0574] 1. Pre-emergence herbicidal effect on harmful plants

[0575] Seeds of monocotyledonous or dicotyledonous weed plants and crop plants are placed in sandy loam in a wooden fiber pot and covered with soil. Then, the compounds of the present invention (formulated as a wettable powder (WP) or as an emulsifiable concentrate (EC)) are applied in the form of an aqueous suspension or emulsion to the surface of the covered soil at a water application rate equivalent to 600 to 800 L / ha, while adding 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and the greenhouse conditions are maintained under good growth conditions for the test plants. After a 3-week test period, the damage to the test plants is visually evaluated by comparison with an untreated control group (herbicidal activity percentage (%): 100% activity = the plant has died, 0% activity = the same as the control plant). Many compounds of the present invention exhibit very good effects on many important harmful plants. The following table shows, by way of example, the post-emergence herbicidal effects of the compounds of the present invention, with the herbicidal activity expressed as a percentage.

[0576] Table 1a: Pre-emergence effect on ABUTH at 20 g / ha in %

[0577]

[0578]

[0579] Table 1b: Pre-emergence effect on ABUTH at 80 g / ha in %

[0580]

[0581]

[0582]

[0583] Table 1c: Pre-emergence effect on ABUTH at 320 g / ha in %

[0584]

[0585] Table 2a: Pre-emergence effect on ALOMY at 20 g / ha in %

[0586]

[0587]

[0588] Table 2b: Pre-emergence effect on ALOMY at 80 g / ha in %

[0589]

[0590]

[0591] Table 2c: Pre-emergence activity against ALOMY in % at 320 g / ha

[0592]

[0593]

[0594] Table 3a: Pre-emergence activity against AMARE in % at 20 g / ha

[0595]

[0596]

[0597] Table 3b: Pre-emergence activity against AMARE in % at 80 g / ha

[0598]

[0599]

[0600]

[0601] Table 3c: Pre-emergence activity against AMARE in % at 320 g / ha

[0602]

[0603] Table 4a: Pre-emergence activity against AVEFA in % at 20 g / ha

[0604]

[0605] Table 4b: Pre-emergence activity against AVEFA in % at 80 g / ha

[0606]

[0607] Table 4c: Pre-emergence activity against AVEFA in % at 320 g / ha

[0608]

[0609] Table 5a: Pre-emergence activity against CYPES in % at 20 g / ha

[0610]

[0611] Table 5b: Pre-emergence activity against CYPES in % at 80 g / ha

[0612]

[0613]

[0614] Table 5c: Pre-emergence activity against CYPES in % at 320 g / ha

[0615]

[0616] Table 6a: Pre-emergence activity against ECHCG in % at 20 g / ha

[0617]

[0618] Table 6b: Pre-emergence activity against ECHCG in % at 80 g / ha

[0619]

[0620]

[0621]

[0622] Table 6c: Pre-emergence activity against ECHCG in % at 320 g / ha

[0623]

[0624] Table 7a: Pre-emergence activity against MATIN in % at 20 g / ha

[0625]

[0626]

[0627] Table 7b: Pre-emergence activity against MATIN in % at 80 g / ha

[0628]

[0629]

[0630] Table 7c: Pre-emergence activity against MATIN in % at 320 g / ha

[0631]

[0632]

[0633] Table 8a: Pre-emergence activity against PHBPU in % at 80 g / ha

[0634]

[0635] Table 8b: Pre-emergence activity against PHBPU at 320 g / ha, in %

[0636]

[0637] Table 9a: Pre-emergence activity against POLCO at 20 g / ha, in %

[0638]

[0639] Table 9b: Pre-emergence activity against POLCO at 80 g / ha, in %

[0640]

[0641] Table 9c: Pre-emergence activity against POLCO at 320 g / ha, in %

[0642]

[0643]

[0644] Table 10a: Pre-emergence activity against SETVI at 20 g / ha, in %

[0645]

[0646] Table 10b: Pre-emergence activity against SETVI at 80 g / ha, in %

[0647]

[0648]

[0649] Table 10c: Pre-emergence activity against SETVI at 320 g / ha, in %

[0650]

[0651]

[0652] Table 11a: Pre-emergence activity against STEME at 20 g / ha, in %

[0653]

[0654] Table 11b: Pre-emergence activity against STEME at 80 g / ha, in %

[0655]

[0656]

[0657] Table 11c: Pre-emergence activity against STEME, % at 320 g / ha

[0658]

[0659] Table 12a: Pre-emergence activity against VERPE, % at 20 g / ha

[0660]

[0661] Table 12b: Pre-emergence activity against VERPE, % at 80 g / ha

[0662]

[0663] Table 12c: Pre-emergence activity against VERPE, % at 320 g / ha

[0664]

[0665]

[0666] Table 13a: Pre-emergence activity against VIOTR, % at 20 g / ha

[0667]

[0668] Table 13b: Pre-emergence activity against VIOTR, % at 80 g / ha

[0669]

[0670]

[0671] Table 13c: Pre-emergence activity against VIOTR, % at 320 g / ha

[0672]

[0673] Table 14a: Pre-emergence activity against LOLRI, % at 80 g / ha

[0674]

[0675] Table 14b: Pre-emergence activity against LOLRI, % at 320 g / ha

[0676]

[0677] Table 15a: Pre-emergence activity against HORMU, % at 80 g / ha

[0678]

[0679] Table 15b: Pre-emergence action against HORMU in % at 320 g / ha

[0680]

[0681] Table 16a: Pre-emergence action against DIGSA in % at 20 g / ha

[0682]

[0683]

[0684] Table 16b: Pre-emergence action against DIGSA in % at 80 g / ha

[0685]

[0686] 2. Post-emergence herbicidal action against harmful plants

[0687] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in a wooden fiber pot, covered with soil, and cultivated in a greenhouse under good growth conditions. Two to three weeks after sowing, the test plants are treated at the single-leaf stage. Then, the compounds of the present invention (formulated as wettable powder (WP) or as emulsifiable concentrate (EC)) are sprayed in the form of an aqueous suspension or emulsion onto the green parts of the plants, with a water application rate equivalent to 600 to 800 L / ha, while adding 0.2% wetting agent. Approximately three weeks after placing the test plants in a greenhouse under optimal growth conditions, the action of the formulation is visually evaluated by comparison with an untreated control group (herbicidal action percentage (%): 100% activity = plant death, 0% activity = same as control plants). Many compounds of the present invention exhibit good action against many important harmful plants. The following table exemplarily illustrates the post-emergence herbicidal action of the compounds of the present invention, with the herbicidal activity expressed as a percentage.

[0688] Table 17a: Post-emergence action against ABUTH in % at 5 g / ha

[0689]

[0690]

[0691] Table 17b: Post-emergence action against ABUTH in % at 20 g / ha

[0692]

[0693]

[0694] Table 17c: Post-emergence effect on ABUTH in % at 80 g / ha

[0695]

[0696]

[0697] Table 18a: Post-emergence effect on ALOMY in % at 5 g / ha

[0698]

[0699]

[0700] Table 18b: Post-emergence effect on ALOMY in % at 20 g / ha

[0701]

[0702]

[0703] Table 18c: Post-emergence effect on ALOMY in % at 80 g / ha

[0704]

[0705] Table 19a: Post-emergence effect on AMARE in % at 5 g / ha

[0706]

[0707]

[0708]

[0709] Table 19b: Post-emergence effect on AMARE in % at 20 g / ha

[0710]

[0711]

[0712] Table 19c: Post-emergence effect on AMARE in % at 80 g / ha

[0713]

[0714]

[0715] Table 20a: Post-emergence effect on AVEFA in % at 5 g / ha

[0716]

[0717] Table 20b: Post - emergence effect on AVEFA in % at 20 g / ha

[0718]

[0719]

[0720] Table 20c: Post - emergence effect on AVEFA in % at 80 g / ha

[0721]

[0722] Table 21a: Post - emergence effect on CYPES in % at 5 g / ha

[0723]

[0724] Table 21b: Post - emergence effect on CYPES in % at 20 g / ha

[0725]

[0726] Table 21c: Post - emergence effect on CYPES in % at 80 g / ha

[0727]

[0728] Table 22a: Post - emergence effect on ECHCG in % at 5 g / ha

[0729]

[0730]

[0731] Table 22b: Post - emergence effect on ECHCG in % at 20 g / ha

[0732]

[0733]

[0734] Table 22c: Post - emergence effect on ECHCG in % at 80 g / ha

[0735]

[0736]

[0737] Table 23a: Post - emergence effect on MATIN in % at 5 g / ha

[0738]

[0739] Table 23b: Post-emergence effect on MATIN at 20 g / ha, in %

[0740]

[0741]

[0742]

[0743] Table 23c: Post-emergence effect on MATIN at 80 g / ha, in %

[0744]

[0745] Table 24a: Post-emergence effect on PHBPU at 5 g / ha, in %

[0746]

[0747]

[0748] Table 24b: Post-emergence effect on PHBPU at 20 g / ha, in %

[0749]

[0750]

[0751] Table 24c: Post-emergence effect on PHBPU at 80 g / ha, in %

[0752]

[0753] Table 25a: Post-emergence effect on POLCO at 5 g / ha, in %

[0754]

[0755] Table 25b: Post-emergence effect on POLCO at 20 g / ha, in %

[0756]

[0757]

[0758] Table 25c: Post-emergence effect on POLCO at 80 g / ha, in %

[0759]

[0760] Table 26a: Post-emergence effect on SETVI at 5 g / ha, in %

[0761]

[0762]

[0763] Table 26b: Post-emergence effect on SETVI in % at 20 g / ha

[0764]

[0765]

[0766] Table 26c: Post-emergence effect on SETVI in % at 80 g / ha

[0767]

[0768]

[0769] Table 27a: Post-emergence effect on STEME in % at 5 g / ha

[0770]

[0771] Table 27b: Post-emergence effect on STEME in % at 20 g / ha

[0772]

[0773]

[0774] Table 27c: Post-emergence effect on STEME in % at 80 g / ha

[0775]

[0776] Table 28a: Post-emergence effect on VERPE in % at 5 g / ha

[0777]

[0778] Table 28b: Post-emergence effect on VERPE in % at 20 g / ha

[0779]

[0780]

[0781] Table 28c: Post-emergence effect on VERPE in % at 80 g / ha

[0782]

[0783]

[0784] Table 29a: Post - emergence effect on VIOTR in % at 5 g / ha

[0785]

[0786]

[0787] Table 29b: Post - emergence effect on VIOTR in % at 20 g / ha

[0788]

[0789]

[0790] Table 29c: Post - emergence effect on VIOTR in % at 80 g / ha

[0791]

[0792] Table 30a: Post - emergence effect on LOLRI in % at 5 g / ha

[0793]

[0794]

[0795] Table 30b: Post - emergence effect on LOLRI in % at 80 g / ha

[0796]

[0797] Table 31a: Post - emergence effect on HORMU in % at 5 g / ha

[0798]

[0799] Table 31b: Post - emergence effect on HORMU in % at 20 g / ha

[0800]

[0801] Table 31c: Post - emergence effect on HORMU in % at 80 g / ha

[0802]

[0803]

[0804] Table 32a: Post - emergence effect on DIGSA in % at 5 g / ha

[0805]

[0806] Table 32b: Post - emergence action against DIGSA in % at 20 g / ha

[0807]

[0808]

[0809] Comparative experiment

[0810] In subsequent experiments, under the specific conditions of the pre - emergence and post - emergence methods described above, the herbicidal action of many compounds of the present invention was compared with that of the structurally closest compounds known from D1 (WO 2012 / 028579 A1). The example numbers given in the table relate to the compounds disclosed in each document.

[0811] Table 33: Pre - emergence herbicidal action

[0812]

[0813]

[0814]

[0815]

[0816]

[0817]

[0818] Table 34: Post - emergence herbicidal action

[0819]

[0820]

[0821]

[0822]

Claims

1. Isophthalamide of formula (I) or a salt thereof Wherein the symbols and subscripts are defined as follows: Q is Q 1 R x is (C1-C6)-alkyl, W is nitrogen, X is halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, Y is halogen, halo-(C1-C6)-alkyl or R 2 (O)2S, with the proviso that when X is halogen, Y is not R 2 (O)2S, Z 1 and Z 2 are each independently one of the following groups, each optionally substituted by 0, 1, 2, 3 or 4 halogen atoms: (C1-C6)-alkyl, (C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, or phenyl optionally substituted by 0, 1, 2 or 3 halogen atoms or (C1-C6)-alkyl, or Z 1 and Z 2 together with the nitrogen atom to which they are attached form pyrazol-1-yl or L-prolin-1-yl ethyl ester, or Z 1 and Z 2 together are (CH2)4, and R 2 is methyl, ethyl, n-propyl or isopropyl.

2. The isophthalamide according to claim 1, wherein Q is Q 1 , R x is Me, Et, Pr or i-Pr, W is nitrogen, X is halogen, (C1-C6)-alkyl or c-Pr, Y is halogen, halo-(C1-C6)-alkyl or SO2Me, with the proviso that when X is halogen, Y is not methylsulfonyl, and Z 1 and Z 2independently (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2-c-Pr, (C1-C6)-alkyl substituted with 0, 1, 2, 3 or 4 halogens, Ph or (2-Me)Ph, or Z 1 and Z 2 together are (CH2)4, or W, Z 1 and Z 2 together are pyrazol-1-yl or L-proline-1-yl ethyl ester, and c-Pr represents cyclopropyl.

3. The isophthalamide according to claim 1, wherein Q is Q 1 , R x is Me, Et or Pr, W is nitrogen, X is F, Cl, Br, I, Me, Et or c-Pr, Y is F, Cl, Br, I, SO2Me, CHF2, CF3 or C2F5, with the proviso that when X is halogen, Y is not methylsulfonyl, and Z 1 and Z 2 independently are Me, Et, c-Pr, CH2-c-Pr, CH2CHF2, CH2CF3, Ph or (2-Me)Ph, or Z 1 and Z 2 together are (CH2)4, or W, Z 1 and Z 2 together are pyrazol-1-yl or L-proline-1-yl ethyl ester, and c-Pr represents cyclopropyl.

4. The isophthalamide of formula (I-a) or a salt thereof wherein the symbols and subscripts are defined as follows: and c-Pr represents cyclopropyl.

5. The isophthalamide of formula (I-a) or a salt thereof wherein the symbols and subscripts are defined as follows: .

6. Isophthalamide of formula (I-b) or a salt thereof Wherein the symbols and subscripts are defined as follows: and c-Pr represents cyclopropyl.

7. Isophthalamide of formula (I-b) or a salt thereof Wherein the symbols and subscripts are defined as follows: .

8. Isophthalamide of formula (I-c) or a salt thereof Wherein the symbols and subscripts are defined as follows: and c-Pr represents cyclopropyl.

9. A herbicidal composition or a plant growth regulating composition, characterized in that The composition comprises one or more of the isophthalamides or salts thereof according to any one of claims 1 to 8.

10. The herbicidal composition according to claim 9, further comprising formulation auxiliaries.

11. The herbicidal composition according to claim 9 or 10, comprising at least one other active ingredient selected from insecticides, acaricides, herbicides, fungicides, safeners and / or growth regulators.

12. The herbicidal composition according to claim 9 or 10, comprising a safener.

13. The herbicidal composition according to claim 12, wherein the safener is selected from pyraclonil, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dimepiperate and dimethachlor.

14. A method for controlling unwanted plants, characterized in that An effective amount of at least one of the isophthalamides according to any one of claims 1 to 8 or a herbicidal composition according to any one of claims 9 to 13 is applied to the location of plants or unwanted vegetation.

15. Use of the isophthalamide or a salt thereof according to any one of claims 1 to 8 or the herbicidal composition according to any one of claims 9 to 13 for controlling unwanted plants.

16. The use according to claim 15, characterized in that The isophthalamide according to any one of claims 1 to 8 is used for controlling unwanted plants in useful plant crops.

17. The use according to claim 16, characterized in that The useful plants are genetically modified useful plants.

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