WO2019228788A1 - 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones and their use as herbicides - Google Patents

Abstract

The present invention relates to new herbicidally active 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones according to general formula (I) or agrochemically acceptable salts thereof, and the use of these compounds for controlling weeds and weed grasses in plant crops.

Description

 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones and their use as herbicides

description

The present invention relates to novel herbicidally active 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones according to the general formula (I) or agrochemically acceptable salts thereof, as well as their use for controlling weeds and weeds in crops.

The class of 3-arylpyrrolidine-2,4-diones and their preparation and use as herbicides are well known in the art.

In addition, however, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) and also substituted monocyclic 3-arylene derivatives are also suitable. Arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) having herbicidal, insecticidal or fungicidal activity.

Alkynyl-substituted-3-phenylpyrrolidine-2,4-diones with herbicidal activity are also known from WO 96/82395, WO 98/05638, WO 01/74770, WO 15/032702 or WO 15/040114.

The effectiveness of these herbicides against harmful plants depends on numerous parameters, for example on the application rate used, the formulation (formulation), the respective harmful plants to be controlled, the harmful plant spectrum, the climate and soil conditions and the duration of action or rate of degradation of the herbicide. Numerous herbicides from the group of 3-arylpyrrolidine-2,4-diones require, in order to develop a sufficient herbicidal action, high application rates and / or have only a narrow weed spectrum, which makes their use economically unattractive. There is therefore a need for alternative herbicides which have improved properties as well as being economically attractive and at the same time efficient.

The object of the present invention is consequently to provide novel compounds which do not have the disadvantages mentioned.

The present invention therefore relates to novel 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones of the general formula (I),

and their agrochemically acceptable salts, in which

R ^{1 is} (C ¹ -C ₆ ) alkyl, (C ₂ -C ₄ ) haloalkyl or (C ₃ -C ₆ ) cycloalkyl;

R ^{2 is} (C ₁ -C ₂ ) -alkoxy or (C ₁ -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl;

G is hydrogen, a leaving group L or a cation E, where

L is one of the following radicals

means, in which

R ^{4 is} (C 1 -C ₄ ) alkyl or (C ₁ -C ₃ ) alkoxy (C ₂ -C ₄ ) alkyl;

R ^{5 is} (C 1 -C ₄ ) -alkyl;

R ^{6 is} (C 1 -C ₄ ) -alkyl, an unsubstituted phenyl or a mono- or polysubstituted with halogen,

(C ₁ -C ₄₎ - alkyl, (Ci-C ₄₎ -haloalkyl, (Ci-C ₄₎ alkoxy, (Ci-C ₄₎ haloalkoxy, nitro or cyano-substituted phenyl;

R ⁷ , R ⁷ 'independently of one another are methoxy or ethoxy;

R ⁸ , R ⁹ each independently represent methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen or Form sulfur atom,

E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal or a magnesium-halogen cation,

an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups (Ci-Cio) - alkyl or (C3-C7) -cycloalkyl can be replaced, whereby these independently of each other in each case one or more times with fluorine, chlorine, bromine, cyano, hydroxy substituted or interrupted by one or more oxygen or sulfur atoms could be,

 a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example, in each case morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [1.1.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undec -7-en (DBU),

 a heteroaromatic ammonium cation, for example, respectively

 protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline , 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate or

 may also stand for a Trimethylsulfoniumion.

Alkyl denotes saturated, straight-chain or branched hydrocarbon radicals with the number of carbon atoms given in each case, for example (C ₁ -C ₆ ) -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 Ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.

Alkyl substituted by halogen means straight-chain or branched alkyl groups, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms, e.g. C 1 -C 2 -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, l, l-trifluoropropane 2-yl.

Alkenyl denotes unsaturated, straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms and a double bond in any desired position, for example C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2 Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2- Methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2- pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3 - butenyl, 1,2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2- butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butene yl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2 propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

Alkynyl means straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms and a triple bond in any desired position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 1, 1-Dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1 - Ethyl 2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

Cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on the cycloalkyl, z. As an alkylidene group such as methylidene, are included.

Alkoxy represents saturated, straight-chain or branched alkoxy radicals with the number of carbon atoms given in each case, for example C ₁ -C ₆ -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethyl ethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3

Methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,

2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,

1.1.2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkoxy substituted by halogen means straight-chain or branched alkoxy radicals having in each case the number of carbon atoms indicated, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g. C 1 -C 2 -haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,

2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-1,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoro- ethoxy and l, l, l-trifluoroprop-2-oxy.

The compounds of the formula (I) may, depending on the nature of the substituents, be present as geo metric and / or optical isomers or mixtures of isomers, in different composition, for example, also in cis or trans form, which are defined as follows:

 trans-form cis-form

The optionally obtained in the synthesis isomer mixtures can be separated by the usual technical methods.

Both the pure isomers and the Tautomeren- and isomer mixtures, their preparation and use and compositions containing them are the subject of the present invention. However, in the following, for the sake of simplicity, reference will always be made to compounds of the formula (I), although both the pure compounds and optionally mixtures with different proportions of isomeric and tautomeric compounds are meant.

The compounds of the invention are generally defined by the formula (I). preferred Substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:

Preference is given to compounds of the formula (I) in which

R ^{1 is} (C ₁ -C ₃ ) alkyl, (C ₂ -C ₃ ) haloalkyl or cyclopropyl;

R ^{2 is} (C ₁ -C ₂ ) -alkoxy or (C ₁ -C ₂ ) -alkoxy- (C ₁ -C ₂ ) -alkyl;

G is hydrogen, a leaving group L or a cation E, where

F is one of the following radicals

means, in which

R ^{4 is} C ₁ -C 12 alkyl or (C ₁ -C ₂ ) alkoxyethyl;

R ^{5 is} (Ci-Cü-alkyl;

R ⁶ denotes (C 1 -C 4) -alkyl, an unsubstituted phenyl or a phenyl which is monosubstituted or polysubstituted by halogen, methyl, methoxy, halomethoxy, nitro or cyano,

E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation, or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups (Ci-C ₁₀₎ - alkyl or (C ₃ -C ₇ ) -cycloalkyl may be replaced, wherein these independently of one another in each case may be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms.

Particular preference is given to compounds of the formula (I) in which

R ^{1 is} methyl or ethyl;

R ^{2 is} methoxy, ethoxy or methoxymethyl;

 G is hydrogen, a leaving group F or a cation E, where

F is one of the following radicals

means, in which

R ^{4 is} methyl, ethyl, n-propyl, isopropyl or t-butyl;

R ^{5 is} methyl or ethyl;

 E is a sodium or potassium ion, an ion equivalent of magnesium, calcium or aluminum.

In detail, the following compounds of the formula (I) according to the invention may be mentioned by way of illustration:

Table 1: Compounds of the general formula (I)

The preparation of the compounds of general formula (I) according to the invention is known in principle or can be carried out according to methods known from the literature, for example by

a) a compound of general formula (II)

in which R ¹ and R ^{2 have} the abovementioned meaning, and R ^{10 is} alkyl, preferably methyl or ethyl, optionally in the presence of a suitable solvent or diluent, cyclized with a suitable base with formal cleavage of the group R ¹⁰ OH, or b) a compound of the general formula (Ia),

in which R ¹ and R ^{2 have} the meanings given above, for example with a compound of general formula (III), Hal-L (III) in which L has the abovementioned meaning and Hal is a halogen, preferably chlorine or bromine , optionally in the presence of a suitable solvent or diluent, and a suitable base, reacting,

(c) by reacting compounds of general formula (IV),

in which R ¹ , R ² and G have the abovementioned meanings, and U is a suitable leaving group, with a suitable alkynyl reagent of the general formula (V), w = - CH ₃ (V) in the W for hydrogen or a suitable leaving group, if appropriate in the presence of suitable catalysts and a suitable base, is reacted. Suitable leaving groups W are, for example, halogen atoms such as chlorine, bromine or iodine, alkylsulfone ester groups such as triflate, mesylate or nonaflate, magnesium chloride, magnesium bromide, zinc chloride, a trialkyltin radical, carboxyl and boric acid radicals such as -B (OHh or -B (Oalkyl) 2 Pd.sup. + Complexes are particularly well suited as catalysts, and in many cases the addition of Cu ^(I) salts can also be very advantageous, and also figured materials such as 1,4-bis (diphenylphosphino) butane can be used.

The methodology described is state of the art and, moreover, also under the heading "palladium-catalyzed cross-coupling", "Sonogashira, Negishi, Suzuki, Stille or Kumada coupling" pertinent literature known · Another alternative is a compound of general formula (IV) with an alkynyl reagent of general formula (IX), wherein R ^{11 is} , for example, a C 1 -C 4 -trialkylsilyl radical and W has the abovementioned meaning, in analogous application of the above-described coupling methodology to a compound of general formula (X) implement. The group R ¹¹ can then be split off under suitable conditions and gives compounds of the formula (I) according to the invention.

 This technique is described, for example, in the Journal of Medicinal Chemistry 2007, 50 (7), 1627-1634.

The required precursors of the general formula (II)

can in analogy to known methods, for example by reacting an amino acid ester of the general formula (XI) with a phenylacetic acid of the general formula (XII), wherein R ¹ , R ² and R ^{10 have} the meaning described above, optionally by adding a dehydrating agent and optionally in the presence of a suitable solvent or diluent. The preparation of amino acid esters of the general formula (XI) is described, for example, in WO 04/024688 or WO 08/067873.

Another variant for the preparation of precursors of the general formula (II) is, inter alia, that a compound having the general formula (XIII) in which R ¹ , R ² R ¹⁰ and U have the abovementioned meaning, according to the already described cross-coupling methodology with a compound of general formula (V), in which W has the meaning indicated above, is reacted:

The required precursors of the general formula (XII) can be obtained, for example, by using a compound having the general formula (XIV), in which R ¹ , R ¹¹ and U have the abovementioned meaning, according to the already described cross-coupling methodology with a Compound of the general formula (V), in which W has the meaning indicated above, and the resulting carboxylic acid esters are cleaved by standard methods:

The required precursors of the general formula (XIV) can be obtained, for example, by introducing, by literature methods, an acetate unit into compounds of the general formula (XVI) in which R ¹ and U have the abovementioned meaning.

This can be done, for example, analogously to the processes described in WO 05/44796 or in WO 10/115780 by Meerwein- arylation of an aniline of the general formula (XVI) with vinylidene chloride followed by hydrolysis of the intermediate compound (XV) with alcohol at:

In addition, other alternative production processes are known, which are described in WO 15/032702.

In turn, precursors of general formula (XVI) can be obtained by standard commercial methods such as bromination and / or alkylation from commercially available aminonitrophenols.

The compounds of the formula (I) according to the invention (and / or their salts), together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants.

The present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied. The compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufverfahren be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.

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

Dicotyledonous weeds of the 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 , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage stage, but then stop their growth.

When the active ingredients are applied to the green parts of the plant post-emergence, growth stops after treatment and the harmful plants remain in the application at the time of application existing stage of growth or die completely after a certain time, so that in this way harmful to the crops weed competition is eliminated very early and sustainably.

The compounds according to the invention can have selectivities in useful cultures and can also be used as nonselective herbicides.

Due to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain active ingredients used in the agricultural industry, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known. Other particular properties are tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation.

Preference is given to the use of the compounds of the formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants,

The compounds of the formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.

Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, EP 0131624). For example, in several cases, genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgenic crop plants which are resistant to certain glufosinate-type herbicides (US Pat. See, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or are resistant to combinations or mixtures of these herbicides by gene stacking, such as transgenic crops e.g. For example, corn or soybean with the trade name or designation Optimum ™ GAT ™ (Glyphosate ALS Tolerant). Transgenic crops, such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A). Transgenic crops with modified fatty acid composition (WO 91/013972 A). genetically modified crops with new content or secondary substances, for example, new phytoalexins which cause increased disease resistance (EP 0309862 A, EP 0464461 A) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398 A) transgenic crop plants produce pharmaceutically or diagnostically important proteins ("molecular pharming") transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of the above-mentioned new properties ("gene stacking")

Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; see, e.g. 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).

For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. By means of standard methods, for example, base exchanges can be made, partial sequences removed or natural or synthetic sequences added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see eg Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. However, to achieve localization in a particular compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a particular 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., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.

The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

Preferably, the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. 2,4-D, dicamba or against herbicides containing essential plant enzymes, e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenases (HPPD) inhibit or resistant to herbicides from the group of sulfonylureas, the glyphosate, glufosinate or Benzoylisoxazole and analogues, or against any combination of these agents resistant.

The compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. Very particularly preferably, the Inventive compounds in transgenic crops such. As corn or soybean with the trade name or the name OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.

In the application of the active compounds according to the invention in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.

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

The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.

The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Animal", MC Publ Corp., Ridgewood NJ, Sisley and Wood, "Encyclopaedia of Surface Active Agents", Chem. Publ. Co. Ine., NY 1964, Schonfeldt, "Border-Active Ethylene Oxide Adducts", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th Aull. 1986th

On the basis of these formulations, it is also possible to use combinations with other active substances, such as, for example, Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.

Examples of combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase are based, can be used, for example from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and cited there. The following are examples of known herbicides or plant growth regulators, which can be combined with the compounds of the invention, these agents either with their "common name" in the English version according to International Organization for Standardization (ISO) or with the chemical name or with the code number are designated. In this case, all forms of application such as acids, salts, esters and all isomeric forms such as stereoisomers and optical isomers are always included, even if they are not explicitly mentioned.

Examples of such herbicidal mixture partners are:

Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocycloprachlor-potassium, aminocyclopyrachloromethyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorofluorol, chlorofurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorothal-dimethyl, chlorosulfuron, 3- [5-chloro-4- (trifluoromethyl) pyridin-2-yl] 4-hydroxy-1-methylimidazolidin-2-one, cinidone, 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, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, - isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet , n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidine -3-one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidin-3-one, dichloroprop, dichloroprop-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-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb , ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozine, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, ie N- [2-chloro-4-fluoro-5- [4- (3 -fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967, ie 3 - [7 -chloro-5-fluoro-2- (trifluoromethyl) 1-H-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, flazasu lfuron, florasulam, florpyrauxifen, florpyraxifen-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, -dimethylammonium and -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, -isopropylammonium, -diammonium, - dimethylammonium, -potassium, -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioate, halo-tylose, halo-bis-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyf op, haloxyfop-P, haloxyfopethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, HW-02, ie, 1- (dimethoxyphosphoryl) ethyl- (2,4-dichlorophenoxy) acetate, 4-hydroxy-1-methoxy-5-methyl-3- [4- (trifluoromethyl) pyridin-2-yl] imidazolidin-2-one, 4-hydroxy-1-methyl-3- [4- (trifluoromethyl) pyridin-2-yl] imidazolidin-2-one, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr- isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyrimmonium , imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isourone, isoxaben, isoxaflutole, karbutilate, KUH-043, ie 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 butotyl, dimethyl ammonium, 2-ethylhexyl, isopropyl ammonium, potassium and sodium, MCPB, MCPB methyl, ethyl and sodium, mecoprop, mecoprop-sodium, P, mecoprop-P-butotyl, -dimethylammonium, 2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie, 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole , neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamide, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, pr opisochlor, 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, pyramidal, 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, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie, 1-ethoxy-3-methyl-1-oxobut 3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie 1- [7-fluoro-3-oxo-4- (prop-2 -n-1-yl) -3,4-dihydro-2H-l, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (Trif luoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, 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, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862, ie 3,4-dichloro-N- {2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following Links:

Examples of plant growth regulators as possible mixing partners are:

Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chloroform quaternary chloride, cloprop, cyclanilide, 3- (cycloprop-1-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA ), 4-indol-3-yl-butyric acid, isoprothiolanes, probenazoles, jasmonic acid, methyl jasmonate, maleic hydrazides, mepiquat chlorides, 1-methylcyclopropenes, 2- (1-naphthyl) acetamides, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate- mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

Safeners which can be used in combination with the compounds of the formula (I) according to the invention and, if appropriate, in combinations with further active ingredients such as, for example, insecticides, acaricides, herbicides, fungicides as listed above, are preferably selected from the group consisting of: S 1) compounds of the formula (S 1),

where the symbols and indices have the following meanings: n _A is a natural number from 0 to 5, preferably 0 to 3; R _A ¹ is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl;

WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (WA ¹ ) to (WA ⁴ ),

ni _A is 0 or 1;

RA ² is ORA ³ , SRA ³ or NRA ³ RA ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the Carbony lgruppe in (Sl) and is unsubstituted or substituted by radicals from the group (C1-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA ³ , NHRA ⁴ or N (CI F) 2, in particular the formula ORA ³ ;

RA ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms; R _A ⁴ is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;

RA ⁵ is H, (Ci-C ₈ ) alkyl, (Ci-C ₈ ) haloalkyl, (Ci-C ₄ ) alkoxy (Ci-C ₈ ) alkyl, cyano or COORA ⁹ , where RA ⁹ hydrogen, (Ci-Cs ) Alkyl, (C 1 -C 5) -haloalkyl, (C 1 -C 4) -alkoxy- (C 1 -C 4) -alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri (C 1 -C 4) -alkyl-silyl;

RA ⁶ , RA ⁷ , RA ⁸ are identical or different hydrogen, (C 1 -C ₈ ) alkyl, (C 1 -C ₈ ) haloalkyl, (C ₃ -C 12) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (Sl ^a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1 Ethyl (2- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S 1-1) ("mefenpyr-diethyl"), and related compounds as described in the A-91/07874 are described; b) Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl ^b ), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S 1-2), 1- (2,4-dichlorophenyl) -5 -isopropyl-pyrazole-3-carboxylic acid ethyl ester (S 1-3), l- (2,4-dichlorophenyl) -5- (l, l-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S 1-4) and related compounds as described in EP-A-333,131 and EP-A-269,806; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (Sl ^c ), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S 1-5), 1- (2- Chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (Sl-6) and related compounds as described, for example, in EP-A-268554; d) compounds of the type of the triazolecarboxylic acids (Sl ^d ), preferably compounds such as fenchlorazole (ethyl ester), ie 1- (2,4-dichlorophenyl) -5-trichloromethyl (1H) -1, 2,4-triazole-3 carboxylic acid ethyl ester (S 1-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S l ^e), preferably compounds such as 5- (2 , 4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S 1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S 1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S 1-11) ("isoxadifen-ethyl ") or n-propyl ester (S 1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-13), as described in the patent application WO-A-95 / 07897. S2) quinoline derivatives of the formula (S2)

where the symbols and indices have the following meanings:

R _B ¹ is halogen, ( _C ¹ -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl; ne is a natural number of 0 to 5, preferably 0 to 3; 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 N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N atom with the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _B ³ , NHR _B ⁴ or NfCl Fb, in particular of the formula OR _B ³ ;

RB ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;

RB ⁴ is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;

TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4) alkyl radicals or by [(C 1 -C 3) alkoxy] carbonyl; preferably: a) Compounds of the 8-quinolinoxyacetic acid (S2 ^a), preferably (5-chloro-8-quinolinoxy) acetic acid, ethyl (l-methylhexyl) ester ( "cloquintocet-mexyl") (S2-1), (5- Chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3),

(5-chloro-8-quinolinoxy) acetic acid 1-allyloxy-prop-2-yl ester (S2-4),

(5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),

(5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),

Allyl (5-chloro-8-quinolinoxy) acetates (S2-7), (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -l-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86,750, EP-A-94,349 and EP-A-191,736 or EP-A-0 492 366, and (5-chloro-8 -quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, such as they are described in WO-A-2002/34048; b) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 ^b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate,

(5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5-chloro-8-quinolineoxy) malonic acid methyl ethyl ester and related compounds, as described in EP-A-0 582 198.

S3) compounds of the formula (S3)

where the symbols and indices have the following meanings:

Rc ¹ is (Ci-C ₄₎ alkyl, (Ci-C ₄₎ haloalkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ haloalkenyl, _(C3-C7) cycloalkyl, preferably dichloromethyl;

Rc ² , Rc ³ are identical or different hydrogen, (Ci-C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, (C i -C) haloalkyl, (C ₂ -C ) haloalkenyl, (Ci-C) alkylcarbamoyl (Ci-C) alkyl, (C ₂ - C ₄₎ Alkenylcarbamoyl- (C i -C ₄ alkyl), (C i -C ₄₎ alkoxy (C i -C ₄ ) alkyl, dioxolanyl (C 1 -C ₄ ) alkyl,

Thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc ² and Rc ³ together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably:

Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-active safeners), such as. B. "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),

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

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

"Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N - [(1,3) dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG Industries

(S3-5),

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

 "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),

"TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)

((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "furilazole" or "MON 13900" ((RS) -3-dichloroacetyl) 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11).

S4) N-acylsulfonamides of the formula (S4) and their salts,

wherein the symbols and indices have the following meanings:

A _D is S0 ₂ -NR _D ³ -C0 or C0-NR _D ³ -S0 ₂ X _D is CH or N;

RD ¹ is CO-NR _D ⁵ RD ⁶ or NHCO-RD ⁷ ;

RD ² is halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -alkoxycarbonyl or ( Ci-C4) alkylcarbonyl;

RD ³ is hydrogen, (C ₁ -C 4) alkyl, (C ₂ -C 4) alkenyl or (C ₂ -C 4) alkynyl; RD ⁴ is halogen, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,

Phenyl, (Ci-C ₄₎ alkoxy, cyano, (Ci-C ₄₎ alkylthio, (Ci-C4) alkylsulfinyl, (Ci-C ₄₎ alkylsulfonyl, (Ci- C4) alkoxycarbonyl or (Ci-C4) alkylcarbonyl;

RD ⁵ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₅ -C ₆ ) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the seven latter radicals are represented by VD substituents from the group halogen, (Ci-C ₆ ) alkoxy, (Ci-C ₆ ) haloalkoxy, ( Ci-C ₂ ) alkylsulfinyl, (Ci-C ₂ ) alkylsulfonyl, (C ₃ -C 6) cycloalkyl, (Ci-C4) alkoxycarbonyl, (Ci-C4) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C 1 -C 4) alkyl and (C 1 -C 4) haloalkyl are substituted;

RD ⁶ is hydrogen, (C _I -C _Ö) alkyl, _(C2 -Ce) alkenyl or (C ₂ -C ₆₎ -alkynyl, where the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4 ) Alkyl, (C 1 -C 4) alkoxy and (C 1 -C 4) alkylthio, or

RD ⁵ and RD ⁶ together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

RD ⁷ is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-Ce) alkyl, (C3-C6) cycloalkyl, where the 2 latter radicals by VD substituents selected from the group halogen, (Ci -C4) alkoxy, (Ci-C ₆ ) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals are also (C1-C4) alkyl and (Ci-C4) haloalkyl substituted; nD is 0, 1 or 2; ni _D is 1 or 2;

VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 ^a ), which are, for example, B. are known from WO-A-97/45016

wherein

RD ⁷ (Ci-Ce) alkyl, (C3-C6) cycloalkyl, where the 2 latter radicals by VD substituents selected from the group consisting of halogen, (Ci-C4) alkoxy, (Ci-C ₆ ) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals also (C1-C4) alkyl and (Ci-C4) haloalkyl are substituted; RD ^{4 is} halogen, (C i -CU) alkyl, (C i -C ₄ ) alkoxy, CF _3; m _D 1 or 2;

VD is 0, 1, 2 or 3; such as

5 Acylsulfamoylbenzoesäureamide, for example, the following formula (S4 ^b ), for example, are known from WO-A-99/16744,

eg those in which

RD ⁵ = cyclopropyl and (RD ⁴ ) = 2-OMe ("cyprosulfamide", S4-1), 0 RD ⁵ = cyclopropyl and (RD ⁴ ) = 5-Cl-2-OMe (S4-2),

RD ⁵ = ethyl and (RD ⁴ ) = 2-OMe is (S4-3),

RD ⁵ = isopropyl and (RD ⁴ ) = 5-Cl-2-OMe is (S4-4) and RD ⁵ = isopropyl and (RD ⁴ ) = 2-OMe is (S4-5). 5 as well as compounds of the type of N-Acylsulfamoylphenylharnstoffe of the formula (S4 ^C), for example, are known from EP-A-365484

wherein

RD R ⁸ and _D ⁹ are independently hydrogen, (Ci-C ₈₎ alkyl, (C3-C8) cycloalkyl, (c3-0 C ₆₎ alkenyl, (C ₃ -C ₆₎ alkynyl, RD ⁴ halogen, (C i -CU) alkyl, (C i -C ₄ ) alkoxy, CF ₃

IU _{D is} 1 or 2; for example, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,

l- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,

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

N-phenylsulfonylterephthalamides of the formula (S4 ^d ) which are known, for example, from CN 101838227,

eg those in which

RD ^{4 is} halogen, (C i -CU) alkyl, (C i -C ₄ ) alkoxy, CF _3; ni _D 1 or 2;

RD ^{5 is} hydrogen, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₅ -C ₆ ) cycloalkenyl.

55) active ingredients from the class of hydroxyaromatic and aromatic-aliphatic

Carboxylic acid derivatives (S5), e.g.

Ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-

Dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.

56) Agents from the class of 1,2-dihydroquinoxaline-2-ones (S6), e.g.

1-Methyl-3 - (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3 - (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2-aminoethyl ) -3- (2-thienyl) -1,2-dihydro-quinoxalin-2-one hydrochloride, 1- (2-

Methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one as described in WO-A-2005/112630. S7) Compounds of the formula (S7) as described in WO-A-1998/38856

wherein the symbols and indices have the following meanings:

RE ¹ , RE ² are, independently of one another, halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkylamino, di (C 1 -C 4) alkylamino, nitro;

A _E is COORE ³ or COSRE ⁴

RE ³ , RE ⁴ are, independently of one another, hydrogen, (C ¹ -C ⁴ ) -alkyl, (C ² -C ⁶ ) -alkenyl,

(C 2 -C 4) alkynyl, cyanoalkyl, (C 1 -C 4) haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, PE ¹ is 0 or 1

P _E ² , n _E ³ are independently 0, 1 or 2, preferably:

 diphenylmethoxy,

 Diphenylmethoxyessigsäureethylester,

Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).

S8) compounds of the formula (S8) as described in WO-A-98/27049

wherein

X _E CH or N, n _F for the case that X _F = N, an integer from 0 to 4 and for the case that X _F = CH, an integer from 0 to 5,

RF ¹ halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, nitro, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylsulfonyl, ( Ci-C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,

RF ^{2 is} hydrogen or (C ¹ -C ₄ ) alkyl

RF ^{3 is} hydrogen, (C ¹ -C ₈ ) alkyl, (C ² -C 4) alkenyl, (C ² -C 4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, same or different radicals from the group consisting of halogen and alkoxy substituted; or their salts, preferably compounds wherein

XF CH, n _{F is} an integer from 0 to 2,

RF ¹ halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy,

RF ^{2 is} hydrogen or (Ci-C4) alkyl,

RF ^{3 is} hydrogen, (C 1 -C 6) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three, identical or different Radicals from the group consisting of halogen and alkoxy substituted, mean, or their salts.

S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.

1,2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS No 219479-18-2),

1,2-Dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS No. 95855-00-8), as described in WO-A-1999/000020 are described.

S 10) compounds of the formulas (S 10 ^a ) or (S 10 ^b ) as described in WO-A-2007/023719 and WO-A-2007/023764

wherein

R _G ^{1 is} halogen, (C 1 -C 4) alkyl, methoxy, nitro, cyano, CF 3, OCF 3

Y _G , Z _G independently of one another O or S, II _{G is} an integer from 0 to 4,

R _G ² (C ₁ -C ₆ ) alkyl, (C ² -C ₆ ) alkenyl, (C ³ -C ₆ ) cycloalkyl, aryl; Benzyl, halobenzyl,

R _G ^{3 is} hydrogen or (Ci-Ce) alkyl.

511) oxyimino compound type compounds (Si l) known as seed dressing agents, such as e.g. "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S 11-1), which is known as a seed safener for millet against damage by metolachlor,

"Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (Si l -2), which was used as seed dressing -Safener for millet is known against damage from metolachlor, and

"Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.

512) Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A- 1998/13361.

513) One or more compounds of group (S13): "naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S 13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.

Fenclorim "(4,6-dichloro-2-phenylpyrimidine) (S13-2), which is used as safener for pretilachlor in sown Rice is known

"Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for sorghum against damage by alachlor and metolachlor,

"CL 304415" (CAS No. 31541-57-8)

(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage of imidazolinones,

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

"MG 838" (CAS Reg. No. 133993-74-5)

(2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia,

"Disulfonone" (O, O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),

"Dietholate" (O, O-diethyl-O-phenyl phosphorothioate) (S13-8),

"Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as rice. B.

"Dimepiperate" or "MY 93" f.S'-1-methyl-1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide Molinate,

"Daimuron" or "SK 23" (1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea), which is known as a safener for rice against damage of the herbicide imazosulfuron,

"Cumyluron" = "JC 940" (3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254) known as safener for rice against damage of some herbicides is

"Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as safener for rice against damage of some herbicides,

"CSB" (l-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage of some herbicides in rice. S15) compounds of the formula (S15) or their tautomers

as described in WO-A-2008/131861 and WO-A-2008/131860, in which

RH ^{1 is} a (Ci-C ₆ ) haloalkyl radical and RH ^{2 is} hydrogen or halogen and

RH ³ , RH ^{4 are} independently hydrogen, (Ci-Ci ₆ ) alkyl, (C ₂ -C 16) alkenyl or (C ₂ -C ₆ ) alkynyl, each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen , Hydroxy, cyano, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4) alkylthio, (Ci-C4) alkylamino, di [(Ci-C4) alkyl] -amino, [(Ci-C4 ) Alkoxy] carbonyl, [(C 1 -C 4) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl fused on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl which is condensed on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 radicals unsubstituted or by an od it is a plurality of radicals from the group halogen, hydroxy, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy,

(C 1 -C 4) haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, [(C 1 -C 4) -alkoxy] -carbonyl, [(C 1 -C 4) Haloalkoxy] carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or denotes

RH ³ (C 1 -C 4) alkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4) haloalkoxy and

R _H ^{4 is} hydrogen or (C 1 -C ⁴ ) -alkyl or

RH ³ and RH ⁴ together with the directly attached N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (C 1 -C ₄ ) alkyl, (C 1 -C ₄ ) haloalkyl, (C 1 -C ₄ ) alkoxy, (C 1 -C ₄ ) haloalkoxy and (C 1 -C ₄ ) ₄ ) alkylthio is substituted, means.

S16) active substances, which are used primarily as herbicides, but also safeners on

Have crops, e.g.

(2,4-dichlorophenoxy) acetic acid (2,4-D),

(4-chlorophenoxy) acetic acid,

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

4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),

(4-chloro-o-tolyloxy) acetic acid (MCPA),

4- (4-chloro-o-tolyloxy) butyric acid,

 4- (4-chlorophenoxy) butyric acid,

 3,6-Dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).

Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichloromide and metcamifen.

Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,

Alkylbenzenesulfonates, lignosulfonate sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonate sodium or oleoylmethyltaurine acid. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatuses such as hammer mills, blower mills and jet mills, and mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic Solvents such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers) produced. Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxethylenesorbitan esters such as polyoxyethylene sorbitan fatty acid esters ,

Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water or oil based. They may, for example, be prepared by wet-milling by means of commercial beads and optionally adding surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.

Emulsions, e.g. Oil-in-water (EW) emulsions may be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.

Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.

Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the preparation of plate, fluid bed, extruder and spray granules, see e.g. Method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For more details on pesticide formulation see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, In., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, Pages 101-103.

The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active ingredient concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional

Formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.

On the basis of these formulations, combinations with other pesticidally active substances, e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.

For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.

With the external conditions such as temperature, humidity, the type of herbicide used, inter alia, the required application rate of the compounds of formula (I) and their salts varies. It can vary within wide limits, for example between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, in particular preferably in the range of 0.05 to 1 kg / ha g / ha. This applies to pre-emergence or post-emergence applications.

Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, v.a. for application to plants or plant parts or seeds, mixed or combined. The carrier, which may be solid or liquid, is generally inert and should be useful in agriculture.

Suitable solid or liquid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol , organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used. Suitable solid carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flour and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems.

Suitable liquefied gaseous diluents or carriers are those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.

It can be used in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.

In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or 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.

The inventive compositions may additionally contain other ingredients, such as surfactants. As surface-active substances are emulsifying and / or foam producing agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, protein hydrolysates, fignin-sulphite liquors and methylcellulose. The presence of a surfactant is necessary when one of the active ingredients and / or one of the inert carriers is not soluble in water and when applied in water. The proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention. Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

Optionally, other additional components may also be included, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers, sequestering agents, complexing agents. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes. In general, the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90%. Active ingredient, most preferably between 10 and 70 weight percent. The active compounds or compositions according to the invention, as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, Kapselsus pensionen, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for Seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macro granules, microgranules, oil dispersible powders, oil miscible flowable concentrates, oil miscible liquids, foams, pastes , Pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, active substance impregnation natural and synthetic substances as well as microencapsulations in polymeric substances and in seed mixtures for seeds, as well as UFV cold and warm mist formulations are used.

The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary diluent, diluent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, defoaming agents, preservatives , secondary thickeners, adhesives, gibberellins and other processing aids.

The compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.

The active compounds according to the invention, as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) active ingredients such as insecticides, Fockstoffen, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, Fertilizers, safeners or semiochemicals.

The treatment according to the invention of the plants and plant parts with the active compounds or agents is carried out directly or by acting on their environment, Febensraum or Fagerraum according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, sprinkling, foaming, brushing, spreading, pouring, drip irrigation and in the case of propagation material, in particular for seeds, Furthermore, by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible to apply the active ingredients by the Ultra-Fow-Volume method or to inject the active compound preparation or the active ingredient itself into the soil.

As also described below, the treatment of transgenic seed with the inventive active ingredients or agents is of particular importance. This relates to the seed of plants containing at least one heterologous gene which allows expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed can be derived, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Preferably, this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European corn borer (European corn borer) and / or Western Com Rootworm. Most preferably, the heterologous gene is from Bacillus thuringiensis.

In the context of the present invention, the agent according to the invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state that is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvest and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight. Alternatively, seed may also be used which, after drying, e.g. treated with water and then dried again.

In general, care must be taken in the treatment of the seed that the amount of the agent and / or other additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.

The agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.

The active compounds according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as UFV formulations.

These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, Konser vierungsmittel, secondary thickeners, adhesives, gibberellins and water ,

Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. As Examples include the known under the names rhodamine B, CI Pigment Red 112 and CI Solvent Red 1 dyes.

Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.

Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.

As preservatives, all substances which can be used for such purposes in agrochemical compositions can be present in the case-mimetic formulations which can be used according to the invention. Examples include dichlorophen and Benzylalkoholhemiformal.

Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.

The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. It can work in conjunction with the Expression-formed substances also experience additional synergistic effects.

For the treatment of seed with the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water, all mixing devices customarily usable for the dressing can be considered. In particular, in the case of pickling, the seed is introduced into a mixer which adds the desired amount of seed dressing formulations, either as such or after prior dilution with water, and mixes until uniformly distributing the formulation on the seed , Optionally, a drying process follows.

The active compounds according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

As plants which can be treated according to the invention, the following main crops are mentioned: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (eg canola), Brassica rapa, B. juncea (eg (field) mustard) and Brassica carinata, rice, Wheat sugar beet, cane, oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables of various botanical taxa such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, organs and grapefruit); Solanaceae sp. (for example, tomatoes, potatoes, peppers, eggplants), Liliaceae sp., Compositae sp. (for example, lettuce, artichoke and chicory - including root chicory, endive or common chicory), Umbelliferae sp. (for example, carrots, parsley, celery and celeriac), Cucurbitaceae sp. (for example cucumber - including gherkin, squash, watermelon, gourd and melons), Alliaceae sp. (for example, leek and onion), Cruciferae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage), Leguminosae sp. (for example, peanuts, peas, and beans - such as barley bean and field bean), Chenopodiaceae sp. (for example, Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), asparagaceae (for example asparagus); Crops and Ornamental plants in the garden and forest; and each genetically modified species of these plants.

As mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-occurring or by conventional biological breeding methods such as crossing or protoplast fusion obtained plant species and Pflan censorten and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.

The erfmdungsgemäße treatment method can for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. 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 refers to a gene that is provided or assembled outside the plant and that when introduced into the nuclear genome, chloroplast genome or mitochondrial genome imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide, or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene, which is defined by its specific Vorhegen in the plant genome, is referred to as a transformation or transgenic event.

Depending on the plant species or plant varieties, their location and their growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention can also lead to superadditive ("synergistic") effects. Thus, for example, the following effects are possible, which go beyond the actually expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active compounds and compositions which can be used according to the invention, better Plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or water or soil salinity, increased flowering, emolliency, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the emmentary products, higher sugar concentration in the fruits, better shelf life and / or processability of the harvested products.

Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).

Examples of nematode-resistant plants are e.g. following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417,

No. 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.

Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants of pollen sterility can also be localized in the nuclear genome his. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.

Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering) which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.

Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants 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 the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol., 7, 139-145), the genes useful for EPSPS from the petunia (Shah et al., 1986, Science 233, 478-481), for an EPSPS from tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704). It can also be a mutated EPSPS. Glyphosate tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above mentioned genes. Plants expressing EPSPS genes conferring glyphosate tolerance are described. Plants which confer other genes which confer glyphosate tolerance, e.g. Decarboxylase genes are described.

Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by having an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.

Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene coding for an HPPD-tolerant enzyme, with a gene coding for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described. In addition, plants can be made even more tolerant to HPPD inhibitors by incorporating into their genome a gene encoding an enzyme that metabolizes or degrades HPPD inhibitors, such as e.g. CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).

Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as acetohydroxy acid synthase, AHAS) confer tolerance to different herbicides or groups of herbicides, e.g. in Tranel and Wright (Weed Science 2002, 50, 700-712). The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described. Other sulfonylurea and imidazolinone tolerant plants are also described.

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

Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants containing a transgene capable of reducing the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in the plant cells or plants. b. Plants containing a stress tolerance enhancing transgene capable of reducing the expression and / or activity of the PARC-encoding genes of the plants or plant cells; c. Plants which contain a stress-promoting transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention have an altered quantity, quality and / or storability of the emmentary product and / or altered properties of certain components of the emmentary product; such as:

1) Transgenic plants that synthesize a modified starch with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of side chains, the viscosity behavior, the gel strength, the Stärkekomgröße and or starch comorphology is altered in wildtype plant cells or plants as compared to the synthesized starch, so that this modified starch is better suited for certain applications.

2) Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants, the Polyfmctose, in particular of the Inulin and levan types, plants that produce alpha-l, 4-glucans, plants that produce alpha-l, 6-branched alpha-l, 4-glucans, and plants that produce alternan.

3) Transgenic plants that produce hyaluronan.

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

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants such as cotton plants containing an altered form of cellulose synthase genes; b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants having increased expression of sucrose phosphate synthase; c) plants such as cotton plants with increased expression of sucrose synthase; d) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. By down-regulating the fiber-selective β-1,3-glucanase; e) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include: a) plants, such as oilseed rape plants, which produce oil of high oleic acid content; b) plants such as oilseed rape plants, which produce oil with a low linolenic acid content. c) plants such as rape plants that produce oil with a low saturated fatty acid content.

Plants or plant varieties (which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (eg RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).

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

Particularly useful transgenic plants which can be treated according to the present invention are plants having transformational events or combinations of transformation events which are the subject of issued or pending petitions in the United States Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the non-regulated status. The information is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http://www.aphis.usda.gov/brs/not_reg.html. At the filing date of this application, the APHIS had either given or is pending petitions with the following information:

- Petition: identification number of the petition. The technical description of the transformation event can be found in the individual petition document available from APHIS on the website via the petition number. These descriptions are hereby incorporated by reference.

- Enlargement of a petition: reference to a previous petition for which an extension or extension is requested. - Institution: name of the person submitting the petition.

- Regulated article: the affected plant species.

Transgenic phenotype: the trait conferred on the plant by the transformation event.

- transformation event or line: the name of the event (sometimes called a line (s)) for which the unregulated status is requested.

- APHIS Documente: various documents that may be published by APHIS regarding the petition or may be obtained from APHIS upon request.

Particularly useful transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).

Chemical examples

The following examples illustrate the invention in more detail.

Example 1.1

3- [2-Bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3-en-2-one

1,300 g (2.87 mmol) of methyl 1- {2- [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] acetamido} -4-methoxycyclohexanecarboxylate were initially charged in 5.8 ml of dimethylformamide, and 0.790 g (6.32 mmol) of potassium tert-butylate was added. The mixture was stirred for 1 h at room temperature, water was added, washed with dichloromethane and acidified with 2N aqueous hydrochloric acid. The precipitated solid was filtered off with suction.

900 mg of a yellow solid were obtained (74% yield).

Example 1.2

Sodium 3- [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] -8-methyl-2-oxo-1-azaspiro [4.5] dec-3-ene-4 -olat

0.102 g (0.243 mmol) of 3- [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3 -en-2-one were dissolved in 0.219 ml of methanol, treated with 0.054 ml of 25% methanolic sodium methoxide solution and stirred for 15 min.

 It was concentrated in vacuo.

 110 mg of the desired salt were obtained (yield 100%).

Example 1.3 3- [2-Bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-ene-4 - ylethyl carbonate

0.750 g (1.78 mmol) of 3- [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3 -en-2-one and 0.361 g of triethylamine were initially charged in 1.16 ml of methylene chloride, and 0.232 g (2.14 mmol) of ethyl chloroformate were added dropwise. The mixture was stirred for 1 h at room temperature. It was washed with water, dried, concentrated and the residue purified by chromatography.

 0.67 g of a light solid was obtained (yield 76%). By analogy with this example and according to the general information on the preparation, the following compounds are obtained:

Table 2: Compounds of the general formula (I)

Production Examples Starting Materials:

Example A.l

 Methyl 1- {2- [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] acetamido} -4-methoxycyclohexanecarboxylate

1,000 g (3.53 mmol) of [2-bromo-6-methoxy-4- (prop-1-yn-1-yl) phenyl] acetic acid were dissolved in 3.33 ml of dichloromethane and admixed with 2 drops of dimethylformamide. At room temperature, 0.616 ml (7.06 mmol) of oxalyl chloride were then slowly added dropwise, then heated to reflux until no more gas evolution was observed and concentrated. In a separate batch, 0.790 g (3.53 mmol) of 4-methoxy-1- (methoxycarbonyl) cyclohexanaminium chloride and 1.969 ml of triethylamine in 3.3 ml of dichloromethane were initially charged and the acid chloride, dissolved in dichloromethane, was added dropwise. It was stirred for 1 h at room temperature.

It was washed with water, the phases were separated and the organic phase was dried over sodium sulfate. After concentration, the residue was purified by chromatography.

1.3 g of a pale oil were obtained (yield 81%). In analogy to this example and according to the general information on the preparation, the following compounds are obtained:

Table A: Compounds of general formula (II) wherein R ¹⁰ = Me

 Example B.2:

 [2-bromo-6-methoxy-4- (prop-l-in-l-yl) phenyl] acetic acid

To a solution of 0.2 g (0.64 mmol) of methyl [2-bromo-6-ethoxy-4- (prop-1-yn-1-yl) phenyl] acetate in 20 ml of tetrahydrofuran and 20 ml of water was added 0.051 g at room temperature (1.28 mmol) of sodium hydroxide and the reaction mixture was heated to 50 ° C for 1 h. After being cooled to room temperature, the tetrahydrofuran was removed by distillation in vacuo and precipitated by the addition of 1M aqueous hydrochloric acid.

After suction, 180 mg of a solid (yield 84%) were obtained, which was used without further purification.

In analogy to this example and according to the general information on the preparation, the following compounds are obtained:

 Table B: Compounds of the general formula (XII)

Methyl [2-bromo-6-ethoxy-4- (prop-1-yn-1-yl) phenyl] acetate

To a solution of 0.102 g (0.75 mmol) of zinc chloride and 0.032 g (0.75 mmol) of lithium chloride in 7 ml of dry tetrahydrofuran under nitrogen were added dropwise at 0 ° C with stirring 1.5 ml (0.75 mmol) of a 0.5 M solution of 1-Propinylmagnesiumbromid in tetrahydrofuran dripped. The solution was warmed to room temperature with stirring over 1.5 h.

 In a second approach, 2.8 mg (0.01 mmol) of palladium (II) acetate and 10.6 mg (0.02 mmol) of l, 4-bis (diphenylphosphino) butane in 3 ml of dry tetrahydrofuran were stirred under nitrogen for 30 min at room temperature.

 In a third batch, 0.2 g (0.5 mmol) of methyl (2-bromo-6-ethoxy-4-iodophenyl) acetate was dissolved in 2 ml of dry tetrahydrofuran under nitrogen and stirred for 30 min at room temperature.

To the solution of the first batch was added dropwise at room temperature under nitrogen with stirring, the solution of the second batch and then the solution of the third approach. After the addition was stirred at 60 ° C for 3.5 h.

 After cooling to room temperature, water and saturated ammonium chloride solution were added and the mixture was extracted with ethyl acetate, and the organic phase was dried and concentrated. The crude product was purified by chromatography.

 98 mg of the desired intermediate were obtained (yield 63%).

'H-NMR (400 MHz, d in ppm, CDCh)

d = 1.35 (t, 3H), 2.05 (s, 3H), 3.70 (s, 3H), 3.85 (s, 2H), 4.00 (q, 2H), 6.80 (s, 1H), 7.20 (s, 1H)

Methyl (2-bromo-4-iodo-6-methoxyphenyl) acetate

 1,300 g (4.74 mmol) of methyl (4-amino-2-bromo-6-methoxyphenyl) acetate were dissolved in 19 ml of acetonitrile, and 2.706 g (14.2 mmol) of p-toluenesulfonic acid were added. The suspension was cooled to 10-15 ° C and slowly added to a solution of 0.654 g (9.48 mmol) of sodium nitrite and 1.968 g (11.08 mmol) of potassium iodide in 1.8 ml of water. After 10 min, the mixture was warmed to room temperature and stirred at 20 ° C. for a further 30 min.

Water was added, adjusted to pH 8 with saturated sodium bicarbonate solution, and saturated sodium thiosulfate added. After extraction with ethyl acetate, the mixture was concentrated and the residue was purified by chromatography.

There were 1,005 g of a yellow-orange oil obtained (55% yield). 'H-NMR (400 MHz, d in ppm, _CDCl3)

d = 3.70 (s, 3H), 3.80 (s, 3H), 3.85 (s, 2H), 7.10 (s, 1H), 7.55 (s, 1H)

Methyl (4-amino-2-bromo-6-methoxyphenyl) acetate

1,450 g (4.76 mmol) of methyl (2-bromo-6-methoxy-4-nitrophenyl) acetate were dissolved in 11 ml of tetrahydrofuran and a solution of 2.040 g (38.1 mmol) of ammonium chloride in 5.3 ml of water and 2.494 g (38.1 mmol). Zinc added. It was stirred for 30 min at room temperature. It was filtered, the filtrate diluted with water and extracted with ethyl acetate, the pH was adjusted to be greater than 7. It was dried with sodium sulfate and concentrated. There was obtained 1.3 g of an orange oil (99% yield).

'H-NMR (400 MHz, d in ppm, CDCl3)

d = 3.70 (s, 3H), 3.75 (s, 5H), 6.15 (s, 1H), 6.55 (s, 1H)

Methyl (2-bromo-6-methoxy-4-nitrophenyl) acetate

3.636 g (10.0 mmol) of 1-bromo-3-methoxy-5-nitro-2- (2,2,2-trichloroethyl) benzene were dissolved in 10 ml of methanol and slowly treated with 10 ml (54.4 mmol) of 30% methanolic sodium methanol At- offset solution, wherein a heat development occurred. The mixture was then heated under reflux for 12 h. Cautiously added 1.1 ml of concentrated sulfuric acid, causing heat to develop. The mixture was refluxed for 1 h. The mixture was concentrated, the residue dissolved in water and extracted with dichloromethane. It was dried with sodium sulfate, concentrated and chromatographed. 1.45 g of a yellow oil were obtained (48% yield).

'H-NMR (400 MHz, d in ppm, CDC1 ₃ )

d = 3.70 (s, 3H), 3.94 (s, 3H), 3.96 (s, 2H), 7.70 (s, 1H), 8.10 (s, 1H) 1-bromo-3-methoxy-5-nitro-2 (2,2,2-trichloroethyl) benzene

 1,547 g (15.0 mmol) of tert-butylnitrite and 1,842 g (13.7 mmol) of copper (II) chloride were suspended in 7.8 ml of acetonitrile and cooled to 0 ° C. Then, 16.48 g (170 mmol) of vinylidene chloride was slowly added dropwise and allowed to come to room temperature. Subsequently, 2,470 g (10 mmol) of 2-bromo-6-methoxy-4-nitroaniline dissolved in 10 ml of acetonitrile and 25 ml of acetone were slowly added dropwise. It was stirred at room temperature until no more gas evolution took place. Under ice-cooling was slowly added to 2 ml of 10% aqueous hydrochloric acid, extracted with ethyl acetate, dried with magnesium sulfate and concentrated.

 This gave 3,636 g of a crude product which still contained copper salts and was used directly in the following reaction.

A. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill. b) A wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and grinding in a pin mill. c) A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO ) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) and milled in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier. e) A water-dispersible granules are obtained by

75 parts by weight of a compound of the formula (I) and / or salts thereof,

 10 parts by weight of lignosulfonic acid calcium,

 5 parts by weight of sodium lauryl sulfate,

 3 parts by weight of polyvinyl alcohol and

7 parts by weight kaolin

milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit. f) A water-dispersible granules are also obtained by

25 parts by weight of a compound of the formula (I) and / or salts thereof,

 5 parts by weight of 2,2 'dinaphthylmethane 6,6' disulfonic acid sodium,

 2 parts by weight of oleoylmethyltaurine sodium,

 1 part by weight of polyvinyl alcohol,

 17 parts by weight of calcium carbonate and

50 parts by weight of water

Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.

B. Biological data

1. Herbicidal action or crop plant compatibility in the pre-emergence

Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then converted as aqueous suspension or emulsion with a water application rate of 600 to 800 1 / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil.

After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants).

Unwanted plants / weeds:

ALOMY: Alopecurus myosuroides SETVI: Setaria viridis

AMARE: Amaranthus retroflexus AVEFA: Avena fatua

CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli

LOLRI: Lolium rigidum STEM: Stellaria media

VERPE: Veronica persica VIOTR: Viola tricolor

POLCO: Polygonum convolvulus ABUTH: Abutylon threophrasti

HORMU: Hordeum murinum

1. pre-emergence effectiveness

As the results of Tables 3 and 4 show, compounds of the invention have good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.

 Table 3: Pre-emergence effect at 320 g / ha

For example, the compounds Nos. 1.01, 1.02, 1.03, 1.04, 1.08 and 1.09 in Table 3 at a rate of 320 g / ha each have a 100% action against Avena fatua, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum. Table 4: Pre-emergence effect at 80 g / ha

As the results from Table 4 show, the compounds Nos. 1.01, 1.02, 1.03, 1.04, 1.08, 1.09, 1.14, 1.15 and 1.16 at a rate of 80 g / ha each have a 90-100% action against Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum. The compounds according to the invention are therefore suitable in the pre-emergence process for

Control of undesirable plant growth.

2. Herbicidal action or crop plant compatibility postemergence

 Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the

Trial plants treated in the single leaf stage. The compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of plants as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent , After about 3 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal activity in percent (%): 100% effect = plants are dead, 0% effect = like control plants).

 As the results of Tables 5 and 6 show, compounds of the present invention have good post-emergence herbicidal activity against a broad spectrum of grass weeds and weeds.

 Table 5: Post-emergence effect at 80 g / ha

For example, compounds Nos. 1.01, 1.03, 1.04, 1.08 and 1.09 in Table 5 at a rate of 80 g / ha each have a 90-100% action against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum , Setaria viridis and Hordeum murinum.

Table 6: Post-emergence effect at 80 g / ha

As the results from Table 6 show, the compounds Nos. 1.02, 1.14, 1.15 and 1.16 at a rate of 80 g / ha each have a 90-100% action against Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum.

The compounds according to the invention are therefore suitable for postemergence treatment of unwanted plants.

Claims

claims

1. 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones of the general formula (I)

and their agrochemically acceptable salts, in which

R ^{1 is} (C ¹ -C ₆ ) alkyl, (C ₂ -C ₄ ) haloalkyl or (C ₃ -Ce) cycloalkyl;

R ^{2 is} (C 1 -C ² ) -alkoxy or (C 1 -C 4) -alkoxy- (C 1 -C 4) -alkyl;

G is hydrogen, a leaving group L or a cation E, where

L is one of the following radicals

means, in which

R ^{4 is} (C 1 -C ₄ ) alkyl or (C ₁ -C ₃ ) alkoxy (C ₂ -C ₄ ) alkyl;

R ^{5 is} (C 1 -C 4) -alkyl;

R ^{6 is} (C 1 -C 4) -alkyl, an unsubstituted phenyl or a mono- or polysubstituted with halogen,

(C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, nitro or cyano-substituted phenyl;

R ⁷ , R ⁷ 'independently of one another are methoxy or ethoxy;

R ⁸ , R ⁹ each independently represent methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen or Form sulfur atom,

E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, or a magnesium-halogen cation means

 an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups

 (Ci-Cio) - alkyl or (C3-C7) -cycloalkyl can be replaced, whereby these

 independently of one another may each be monosubstituted or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxyl or interrupted by one or more oxygen or sulfur atoms,

 a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example, in each case morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [1.1.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undec -7-en (DBU),

 a heteroaromatic ammonium cation, for example, respectively

 protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline , 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate or

 may also stand for a Trimethylsulfoniumion.

2. Compounds of the formula (I) according to Claim 1 or an agrochemically acceptable salt thereof, in which the radicals have the following meanings:

R ^{1 is} (C 1 -C 3) -alkyl, (C 2 -C 3) -propaloalkyl or cyclopropyl;

R ^{2 is} (C 1 -C ² ) -alkoxy or (C 1 -C ² ) -alkoxy- (C 1 -C 2) -alkyl;

G is hydrogen, a leaving group L or a cation E, where

L is one of the following radicals

means, in which

R ^{4 is} (C 1 -C 4) alkyl or (C 1 -C 2) alkoxyethyl;

R ^{5 is} (Ci-G alkyl;

R ^{6 is} (C 1 -C 4) -alkyl, an unsubstituted phenyl or a phenyl which is monosubstituted or polysubstituted by halogen, methyl, methoxy, halomethoxy, nitro or cyano, E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups (Ci-Cio) - alkyl or (C3-C7 ) -Cycloalkyl may be replaced, wherein these independently of one another in each case one or more times with fluorine, chlorine, bromine, cyano, hydroxy substituted or may be interrupted by one or more oxygen or sulfur atoms.

3. Compounds of formula (I) according to claim 1 or 2 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings:

R ^{1 is} methyl or ethyl;

R ^{2 is} methoxy, ethoxy or methoxymethyl;

 G is hydrogen, a leaving group L or a cation E, where

L is one of the following radicals

means, in which

R ^{4 is} methyl, ethyl, n-propyl, isopropyl or t-butyl;

R ^{5 is} methyl or ethyl;

 E is a sodium or potassium ion, an ion equivalent of magnesium, calcium or aluminum.

4. A process for the preparation of the compounds of the formula (I) or an agrochemically acceptable salt thereof according to any one of claims 1 to 3, by reacting a compound of the general formula (II)

in which R ¹ , R ² and R ^{3 have} the abovementioned meaning, and R ^{10 is} alkyl, preferably methyl or ethyl, if appropriate in the presence of a suitable solvent or diluent, with a suitable base with formal cleavage of the group R ¹⁰ OH is cyclized.

5. An agrochemical composition comprising a) at least one compound of formula (I) or an agrochemically acceptable salt thereof as defined in one or more of claims 1 to 3, and b) auxiliaries and additives customary in crop protection.

6. An agrochemical composition comprising a) at least one compound of formula (I) or an agrochemically acceptable salt thereof as defined in one or more of claims 1 to 3, b) one or more agrochemically active compounds other than component a), and optionally c) auxiliaries and additives customary in plant protection.

A method of controlling undesirable plants or regulating the growth of plants, wherein an effective amount of at least one compound of formula (I) or an agrochemically acceptable salt thereof as defined in one or more of claims 1 to 3, on the plants, the Seed or the surface on which the plants grow is applied.

8. Use of compounds of the formula (I) or an agrochemically acceptable salt thereof as defined in one or more of claims 1 to 3, as herbicides or plant growth regulators.

9. Use according to claim 8, wherein the compounds of formula (I) or an agrochemically acceptable salt thereof as defined in one or more of claims 1 to 3 are used for controlling harmful plants or for regulating the growth in plant crops.

Use according to claim 9, wherein the crop plants are transgenic or non-transgenic crop plants.