WO2001010849A2

WO2001010849A2 - Substituted arylalkylamino-1,3,5-triazines as herbicides

Info

Publication number: WO2001010849A2
Application number: PCT/EP2000/007073
Authority: WO
Inventors: Hans-Jochem Riebel; Stefan Lehr; Kristian Kather; Stefan Herrmann; Mark Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen; Yukiyoshi Watanabe; Toshio Goto
Original assignee: Bayer Aktiengesellschaft
Priority date: 1999-08-04
Filing date: 2000-07-24
Publication date: 2001-02-15
Also published as: AU6827300A; DE19936633A1; AR025000A1; CO5210948A1; WO2001010849A3

Abstract

The invention relates to new substituted arylalkylamino-1,3,5-triazines of formula (I), wherein n, R<1>, R<2>, R<3>, R<4>, R<5>,R<6> and R<7> have the meaning given in the description, to a method and intermediates for the production thereof and to their use as herbicides.

Description

Substituted arylal yiaιnino-l, 3..5-triazines

The invention relates to new substituted arylalkylamino-l, 3,5-triazines, a process and new intermediates for their preparation and their use as

Herbicides.

A number of substituted arylalkylamino-1,3,5-triazines are already known from the (patent) literature (cf. US-A-3816419, US-A-3932167, EP-A-191496, EP-A-273328, EP-A-411153 / WO-A-90/09378, WO-A-98/15536, WO-A-98/42684, JP-

A-62294669 - cited in Chem. Abstracts 109: 129062v, JP-A-63051379 - cited in Chem. Abstracts 109: 231079). However, these connections have so far not gained any particular importance.

The new substituted arylalkylamino-1,3,5-triazines of the general formula (I)

in which

n represents the numbers 0, 1, 2 or 3,

R represents hydrogen or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C1-C4alkoxy,

R for hydrogen, for formyl, for alkyl, alkylcarbonyl, alkoxycarbonyl optionally substituted by cyano, halogen or Ci-Cj-alkoxy or alkylaminocarbonyl each having 1 to 5 carbon atoms in the alkyl groups,

or the grouping N (R, R) also represents dialkylaminoalkylidene amino having 1 to 5 carbon atoms in the alkyl groups or in the alkylidene group,

R, 3 for optionally by hydroxy, cyano, halogen, C1-C4-alkoxy, C1-C4-alkyl-carbonyl, Cι-C4-alkoxy-carbonyl, C1-C4-alkylthio, Cι-C4-alkylsulfinyl or C1 - C4-alkylsulfonyl-substituted alkyl having 1 to 5 carbon atoms in the alkyl groups, or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkyl,

R »4 for optionally substituted by cyano, halogen or C1-C4-alkoxy

Alkyl having 1 to 5 carbon atoms or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkyl,

R ⁵ for cyano, nitro, halogen, for alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each with 1 to 5 each optionally substituted by cyano, halogen or -CC ₄ alkoxy Carbon atoms in the alkyl groups, and - if n stands for the numbers 2 or 3 - also stands for hydrogen,

R ⁶ for cyano, nitro, halogen, for alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each with 1 to 5 each optionally substituted by cyano, halogen or C 1 -C ₄ alkoxy Carbon atoms in the alkyl groups, and n

R represents halogen or alkyl or alkoxy each having 1 to 3 carbon atoms,

found.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are described below.

n preferably represents the numbers 0, 1, 2 or 3.

R ¹ preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.

R ² preferably represents hydrogen, formyl or, if appropriate, in each case

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethyl aminocarbonyl, n - or i-propylaminocarbonyl,

1 9 or the grouping N (R, R) also preferably represents dimethylamino-methylenamino or diethyaminomethyleneamino.

R preferably represents in each case optionally by hydroxy, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl. R ⁴ preferably represents in each case optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or for each cyclopropyl, cyclobutyl, cyclopentyl or optionally substituted by cyano, fluorine, chlorine, methyl or ethyl

Cyclohexyl.

R ⁵ preferably stands for cyano, nitro, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Butyl, acetyl, propionyl, n- or i-

Butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, Ethylsulfmyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, and - if n stands for the numbers 2 or 3 - also for hydrogen.

R preferably represents cyano, nitro, fluorine, chlorine, bromine, for methyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl .

Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.

n

R preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.

n particularly preferably represents the numbers 0, 1 or 2. R ¹ particularly preferably represents hydrogen, methyl or ethyl.

R ² particularly preferably represents hydrogen, formyl, methyl, ethyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

or the grouping N (R ', R ² ) is preferably also dimethylamino-methylenamino.

R, 3 particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , or for cyclopropyl optionally substituted by fluorine, chlorine or methyl.

R ⁴ particularly preferably represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine, or cyclopropyl which is optionally substituted by fluorine, chlorine or methyl.

R ⁵ particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxy, ethoxy, n, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy - or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, and - if n is 2 - also hydrogen. R ⁶ particularly preferably stands for cyano, nitro, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or, respectively, which are optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.

R ⁷ particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.

n very particularly preferably stands for the numbers 0 or 1.

R ¹ very particularly preferably represents hydrogen.

R ² very particularly preferably represents hydrogen, formyl, acetyl or

propionyl,

or the grouping N (R *, R ² ) is preferably also dimethylamino-methylenamino.

R ³ very particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy.

R ⁴ very particularly preferably represents methyl or ethyl.

R ⁵ very particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy

Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, and - in the event that n represents the number 2 - also for hydrogen.

R ⁶ very particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, and in each case methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-

Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, or for dimethylamino.

R ⁷ very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.

A particularly preferred group are the compounds of the general formula (I) in which the substituents on the carbon atom to which R ^{4 is} bonded are arranged in the R configuration.

Another particularly preferred group are the compounds of the general formula (I) in which the substituents on the carbon atom to which R ^{4 is} bonded are arranged in the S configuration.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges. Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to those compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Those compounds of the formula (I) which have a combination of the meanings listed above as being very particularly preferred are very particularly preferred according to the invention.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.

The alkyl groups in the definition of R ³ can optionally also contain asymmetrically substituted carbon atoms. In these cases, the possible R and S forms as well as the mixtures thereof are claimed according to the invention.

Examples of the compounds of formula (I) according to the invention are listed in the groups below. Group 1

R ⁴ , R ⁵ , R ⁶ and (R ⁷ ) _n have, for example, the meanings given in the table below:

Group 2

R, R ⁵ , R and (R ⁷ ) _n have, for example, the meanings given above in Group 1.

Group 3

R ⁴ , R ⁵ , R ⁶ and (R ⁷ ) _n have, for example, the meanings given above in Group 1.

Group 4

R ⁴ , R ⁵ , R ⁶ and (R ⁷ ) _n have, for example, the meanings given above in Group 1. Group 5

Group 6

Group 7

R ⁴ , R ⁵ , R ⁶ and (R ⁷ ) _n have, for example, the meanings given above in Group 1. Group 8

Group 9

Group 10

R ⁴ , R ⁵ , R ⁶ and (R ⁷ ) _n have, for example, the meanings given above in Group 1. Group 11

Group 12

The new substituted arylalkylamino-1,3,5-triazines of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.

The new substituted arylalkylamino-1,3,5-triazines of the general formula (I) are obtained if biguanides of the general formula (II)

in which

n, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given above,

and / or acid adducts of compounds of the general formula (II)

with alkoxycarbonyl compounds of the general formula (III)

R ^J -CO-OR '(III) in which

R has the meaning given above and

R 'represents alkyl,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and optionally on the compounds of the general formula (I) thus obtained as part of the definition of the substituent, further conversions according to customary methods

Methods.

If, for example, l- [l- (2,5-difluorophenyl) ethyl] biguanide and chlorodifluoroacetic acid methyl ester are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

The biguanides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II). In the general formula (II), n, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I ) preferably or as particularly preferred for n, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have been} specified.

Suitable acid adducts of compounds of formula (II) are their addition products with protonic acids, such as e.g. with hydrogen chloride (hydrogen chloride),

Hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.

The starting materials of the general formula (II) are not yet known from the literature; as new substances, they are also the subject of the present application.

The new biguanides of the general formula (II) are obtained if arylalkylamines of the general formula (IV)

R ⁴ R ⁵

»>» _R e _(IV)

in which

n, R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given above,

and / or acid adducts of compounds of the general formula (IV), such as e.g. the hydrochloride -

with cyanoguanidine ("dicyandiamide") of the formula (V)

optionally in the presence of a reaction auxiliary, such as hydrogen chloride, and optionally in the presence of a diluent, such as n-decane or 1,2-dichlorobenzene, at temperatures between 100 ° C and 200 ° C (cf. the preparation examples).

After their preparation, the biguanides of the general formula (II) can also be used directly for the preparation of the compounds of the general formula (I) by the process according to the invention, without intermediate isolation.

The arylalkylamines of the general formula (IV) required as precursors are known and / or can be prepared by processes known per se (cf. DE-A-3819438, DE-A-19650081, EP-A-551821, EP-A-736509 , EP-A-778260, US-A-5739401).

Formula (III) provides a general definition of the alkoxycarbonyl compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), R ³ preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for R ³ ; R 'preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.

The starting materials of the general formula (III) are known synthetic chemicals.

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent leads. In addition to water, diluents for carrying out the process according to the invention are in particular inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,

Chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium -amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or Potassium, methoxide, ethanolate, n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2.2.2] - octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. The work-up is carried out using customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver,

Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanth.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita,

Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

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, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagaria, Setaria, Rottboell ,

Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to others

Plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth. The active compounds according to the invention for weed control in permanent crops, for example forest, ornamental Wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture areas and for selective weed control in annual cultures are used.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers

Substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. 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.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides for weed control, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfüresate, Bensulfüron (-methyl) Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bis-pyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxy-dim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo- methoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralidon -methyl), chlorosulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiper ate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, diethiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyid, fenoxysulfuron, ethoxysulfuron, ethoxysulfur (-P-ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop- (-methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, Flumiclorac (-pentyl), flumioxazin, flumipropyn, flumet-sulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, fluprop-acil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), flurypyrone (flurypyrone) -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop- (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenone (-methyl),

Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo- sulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metachiazuron, metamiazuron , Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop- amide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiaronone, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon, Oxasulfonon , Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, pysulfufenon (prosulfufenon) , Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac- (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop ( -P-tef uryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor,

Thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

A mixture with other known active ingredients, such as fungicides,

Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the customary manner, for example by watering, spraying, spraying or scattering. The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

A solution of 3.6 g (66 mmol) of sodium methylate in 60 ml of methanol is added

Room temperature (approx. 20 ° C.) with stirring to a mixture of 19.0 g (60 mmol) of l- [l- (2,4-dichlorophenyl) ethyl] biguanide hydrochloride (racemic), 8.0 G

(60 mmol) 2-fluoropropanoic acid methyl ester and 85 ml of methanol. The reaction mixture is stirred for 15 hours at room temperature and then diluted to about three times the volume by slowly adding water. The product obtained in crystalline form is isolated by suction.

5.7 g (29% of theory) of 6- (l-fluoro-ethyl) -N ² - [l- (2,4-dichlorophenyl) ethyl] -l, 3,5-triazine-2 are obtained , 4-diamine (racemate) with a melting point of 122 ° C.

Example 2

A mixture of 3.0 g (9 mmol) of 6- (l-fluoro-ethyl) -N ² - [l- (2,4-dichlorophenyl) - ethyl] -l, 3,5-triazin-2, 4-diamine (racemic), 1.5 g (9 mmol) of N, N-dimethylformamide-dimethylacetal and 40 ml of 1,4-dioxane is at room temperature for 15 hours

(about 20 ° C) stirred. After adding 80 ml of water and 3 ml of conc. Hydrochloric acid, the mixture is stirred for a further 60 minutes at room temperature. The crystalline product is then isolated by suction. 1.4 g (43% of theory) of N- {4- [l- (2,4-dichlorophenyl) ethylamino] -6- (l-fluoro-ethyl) -l, 3,5-triazine are obtained -2-yl} -formamide (racemate) with a melting point of 172 ° C.

Example 3

A mixture of 3.0 g (9 mmol) of 6- (l-fluoro-1-methyl-ethyl) -N ² - [l- (3-chloro-2-fluoro-phenyl) -ethyl] -l, 3, 5-triazine-2,4-diamine and 15 ml propionic anhydride is stirred at 130 ° C for 30 minutes. Then the volatile components are carefully distilled off under reduced pressure. The residue is digested with 20 ml of ethanol and the crystalline product is isolated by suction.

3.1 g (89% of theory) of N- {4- [l- (3-chloro-2-fluorophenyl) ethylamino] -6- (l-fluoro-l-methyl-ethyl) -l are obtained , 3,5-triazin-2-yl} propionic acid amide (racemate) of melting point 130 ° C.

Analogously to Examples 1 to 3 and in accordance with the general description of the production process according to the invention, for example the compounds of the general formula (I) listed in Table 1 below can also be prepared.

Table 1: Examples of the compounds of the formula (I)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a) . (b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with b ⁾ .

The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

Starting materials of formula (II):

Example II-1

The water and as much toluene are distilled off from a mixture of 57 g (0.30 mol) of l- (2,4-dichloropheny) ethylamine, 36 g of 30% hydrochloric acid, 350 ml of toluene and 200 ml of decane until the internal temperature has risen to 140 ° C. Then 25.2 g (0.30 mol) of cyanoguanidine are added and the reaction mixture is 3

Heated to 140 ° C to 145 ° C for hours. After cooling, acetone is added to the mixture and the crystalline product is isolated by suction.

88.5 g (95% of theory) of l- [l- (2,4-dichlorophenyl) ethyl] biguanide hydrochloride are obtained as a solid product.

Analogously to Example II-1, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 2 below.

Table 2:

Examples of the compounds of the formula (II)

These are the corresponding hydrochlorides

Application examples:

Example A Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation so that the desired one

Amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control)

100% = total annihilation

In this test, the compounds according to Preparation Examples 15, 18, 27 and 38, for example, show a strong action against weeds, in some cases with good tolerance to cultivated plants, such as, for example, maize. Table AI: Pre emergence test / greenhouse

Table A2: Pre emergence test / greenhouse

Table A3: Pre emergence test / greenhouse

Table A4: Pre emergence test / greenhouse

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to preparation example 1, 3, 5, 14, 15, 16, 18, 27, 28, 37, 38 and 39 show strong tolerance to cultivated plants, such as cotton, barley, corn and wheat, in some cases with good tolerance Effect against weeds. Table B1: Post emergence test / greenhouse

Table B2: Post emergence test / greenhouse

Table B3: Post emergence test / greenhouse

Table B3: Post emergence test / greenhouse

Table B4: Post emergence test / greenhouse

Table B5: Post emergence test / greenhouse

Table B6: Post emergence test / greenhouse

Table B7: Post emergence test / greenhouse

Table B8: Post emergence test / greenhouse

Table B9: Post emergence test / greenhouse

Table BIO: Post emergence test / greenhouse

Table B 11: Post emergence test / greenhouse

Claims

claims

1. Compounds of the general formula (I)

in which

represents the numbers 0, 1, 2 or 3,

R stands for hydrogen, for formyl, for alkyl, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 5 carbon atoms in the alkyl groups,

or the grouping N (R, R) represents dialkylaminoalkylidene amino having 1 to 5 carbon atoms in the alkyl groups or in the alkylidene group,

R ³ for optionally by hydroxy, cyano, halogen, C1 -C4 alkoxy, Cι-C4 alkyl carbonyl, Cι -C4 alkoxycarbonyl, C1 -C4 alkylthio, Cι -C4 alkylsulfιnyl or C1-C4 alkyl sulfonyl substituted alkyl with 1 to 5 carbon atoms in the alkyl groups, or represents cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkyl, R ^{4 represents} alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen or C1-C4-alkoxy or represents cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4-alkyl,

R ⁵ for cyano, nitro, halogen, for each optionally by cyano,

Halogen or -CC ₄ - alkoxy substituted alkyl, alkylcarbonyl,

Alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 5 carbon atoms in the alkyl groups, and - in the event that n represents the numbers 2 or 3 - also represents hydrogen,

R ⁶ for cyano, nitro, halogen, each alkyl, alkylcarbonyl optionally substituted by cyano, halogen or -C ₄ alkoxy,

Alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 5 carbon atoms in the alkyl groups, and

R ^{7 represents} halogen or alkyl or alkoxy each having 1 to 3 carbon atoms.

2. Compounds according to claim 1, characterized in that

n represents the numbers 0, 1, 2 or 3,

R ^{1 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R ² for hydrogen, formyl or for methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,

1 or the grouping N (R, R) represents dimethylaminomethyleneamino or diethylaminomethyleneamino,

R ³ for each optionally by hydroxy, cyano, fluorine, chlorine,

Bromine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or for each optionally by cyano, fluorine, chlorine, Bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

R ⁴ for each optionally by cyano, fluorine, chlorine, methoxy or

Ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl,

R ⁵ for cyano, nitro, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, and - if n stands for the numbers 2 or 3 - also stands for hydrogen,

R ⁶ for cyano, nitro, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio , n- or i-Propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s - or t-butylamino, dimethylamino or diethylamino, and

R ^{7 represents} fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.

Compounds according to claim 1, characterized in that

n represents the numbers 0, 1 or 2,

R ^{1 represents} hydrogen, methyl or ethyl,

R ^{2 represents} hydrogen, formyl, methyl, ethyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

or the grouping N (R ', R ² ) represents dimethylaminomethyleneamino, R ³ for each optionally by fluorine, chlorine, bromine, methoxy,

Ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, or represents cyclopropyl optionally substituted by fluorine, chlorine or methyl,

R ⁴ for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine or chlorine, or for each optionally substituted by

Fluorine, chlorine or methyl substituted cyclopropyl,

R ⁵ for cyano, nitro, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxy, ethoxy, n- or i, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, and - in the event that n is for the number 2 stands - also stands for hydrogen,

R ⁶ for cyano, nitro, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio , n- or i-Propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or

Diethylamino stands, and R ^{7 represents} fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.

4. Compounds according to claim 1, characterized in that

n represents the numbers 0 or 1,

R ^{1 represents} hydrogen,

R ^{2 represents} hydrogen, formyl, acetyl or propionyl,

or the grouping N (R \ R ² ) represents dimethylaminomethyleneamino,

R ³ represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy,

R ^{4 represents} methyl or ethyl,

R ⁵ for cyano, nitro, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy , n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino,

R ⁶ for cyano, nitro, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy. carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, or represents dimethylamino, and

5. A process for the preparation of compounds according to any one of claims 1 to 4, characterized in that biguanides of the general formula (II)

in which

n, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given in one of claims 1 to 4,

and / or acid adducts of compounds of the general formula (II)

with alkoxycarbonyl compounds of the general formula (III)

R -CO-OR '(III) in which

R has the meaning given in one of claims 1 to 4 and R 'represents alkyl,

and, if appropriate, further conversions are carried out on the compounds of the general formula (I) thus obtained as part of the definition of the substituent by customary methods.

6. Compounds of the general formula (II)

in which

n, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given in one of claims 1 to 4.

7. A method for controlling undesired plant growth, characterized in that at least one compound according to one of claims 1 to 4 is allowed to act on undesired plants and / or their habitat.

8. Use of at least one compound according to one of claims 1 to 4 for controlling unwanted plants.

9. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 4 and conventional extenders and / or surface-active agents.