DE19919790A1 - Use of N-substituted heterocyclyalkylamines as herbicides and new N-substituted thienylaklylamines - Google Patents

Abstract

The invention relates to the use of N-substituted heterocyclylalkylamines of general formula (I), wherein A represents a single bond or alkanediyl, R<1> represents optionally substituted alkyl, R<2> represents hydrogen, amino or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, respectively, Y represents cyano or nitro and Z represents optionally substituted heterocyclyl, as herbicides. The invention also relates to novel N-substituted thienylalkylamines and to methods for producing the same.

Description

The invention relates to the use of N-substituted heterocyclylalkyl amines as herbicides and new N-substituted thienylalkylamines and processes for their manufacture.

It is known that certain N-substituted heterocyclylalkylamines are insecticidal Have properties (cf. EP-A-364844, EP-A-418199, JP-A-08231524 - cited in Chem. Abstracts 125: 300813). About herbicidal properties of such ver However, no ties have become known so far.

It is also known that certain substituted arylalkyl guanidines growth of plants can influence (see. DE-A-33 45 281, US-A-4639268).

It has now been found that the N-substituted heterocyclylalkylamines of the general formula (I)

in which
A represents a single bond or alkanediyl,
R ^{1 represents} optionally substituted alkyl,
R ^{2 represents} hydrogen, amino or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
Y stands for cyano or nitro and
Z represents optionally substituted heterocyclyl,
have strong herbicidal activity.

Saturated or unsaturated hydrocarbon residues, such as alkyl or alkenyl, are - also in connection with heteroatoms, such as in alkoxy - as far as possible in each case straight-chain or branched.

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

The compounds of general formula (I) according to the invention contain at least one carbon-nitrogen double bond and can therefore in ver different E- and Z-configured isomeric forms. The invention be meets both the use of the individual E- and Z-configured isomers Forms of the compounds of general formula (I) as well as the mixtures thereof isomeric compounds.

The compounds of general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore in different enantiomers (R- and S-configured forms) or diastereomers Shapes are available. The invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds the general formula (I) as well as the mixtures of these isomeric compounds.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are described below.
A preferably represents a single bond or alkanediyl having 1 to 4 carbon atoms.
R ¹ preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.
R ² preferably represents hydrogen, amino or alkyl which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl , Alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups.
Z preferably represents an optionally substituted, monocyclic or bi-cyclic heterocyclic grouping from the series furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isazylylol imolyl, isozolylol , Benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl,
where the preferred substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, 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 - haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ - alkylsulphonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkyl carbonyl, C ₁ -C ₄ alkoxy carbonyl, C ₁ -C ₄ alkylamino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl, C ₁ -C ₄ - Alkylaminosulfonyl, di (C ₁ -C ₄ alkyl) aminosulfonyl, phenyl are selected.
A particularly preferably represents a single bond, methylene (-CH ₂ -), dimethylene (ethane-1,2-diyl, -CH ₂ CH ₂ -), ethylidene (ethane-1,1-diyl, -CH (CH ₃ ) -), trimethylene (propane-1,3-diyl, -CH ₂ CH ₂ CH ₂ -) or propane-1,2-diyl (-CH ₂ CH (CH ₃ ) -).
R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
R ² particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, n- each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, 1-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino.
Z particularly preferably represents an optionally substituted, monocyclic or bicyclic heterocyclic grouping from the series furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolylazolol, isolyl, isolyl, isolol, isolyl , Oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, iso quinolinyl, pyrimidinyl, quinazolinyl,
the particularly preferred substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorine dichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s - or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethyl sulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propylyl, methionyl, methionyl, propyl Ethoxycarbonyl, n- or i-propoxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, dimethylaminosulfonyl, diethylamino are selected.
A very particularly preferably represents a single bond or dimethylene (-CH ₂ CH ₂ -).
R ¹ very particularly preferably represents methyl, ethyl, n- or i-propyl.
R ² very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
Z very particularly preferably represents in each case optionally substituted thienyl or benzothienyl,
the very particularly preferred substituents from the series nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfonyl, methylsulfonyl, nylsulfonyl, ethylsulfonyl, ethylsulfonyl, , Trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl are selected.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

According to the invention, the herbicidal use of compounds of Formula (I) in which a combination of those listed as preferred above Meanings exist.

According to the invention, the herbicidal use of Ver is particularly preferred Compounds of formula (I) in which a combination of the above as be meanings particularly preferred are present.

The herbicidal use of Ver is very particularly preferred according to the invention Compounds of formula (I), in which a combination of the above as whole meanings particularly preferred are present.

A small part of the compounds of the general formula (I) is already known (cf. EP-A-364844, EP-A-418199, EP-A-483062, JP-A-08231524 - cited in Chem. Abstracts 125: 300813) or is part of a previous, but not pre-published open registration (cf. DE-A-198 32 447).

A larger part of the compounds of general formula (I) is not yet from the Literature known. Of these, the new connections of the general my formula (I), in which Z represents in each case optionally substituted thienyl or benzothienyl is to be emphasized - the as examples in an older An compounds mentioned N'-cyano-N- [1-methyl-3- (3-thienyl) propyl] - ethanimidamide, N'-cyano-N- [1-ethyl-3- (3-thienyl) propyl] ethanimidamide, N'- Cyano-N- [1-methyl-3- (2-thienyl) propyl] ethanimidamide, N'-cyano-N- [1- (2-  thienyl) ethyl] ethanimidamide and N'-cyano-N- [1- (3-thienyl) ethyl] ethanimidamide (cf. DE-A-198 32 447) are to be excluded.

Thus, as compounds according to the invention, those compounds of general formula (I) are claimed in which
A represents a single bond or alkanediyl having 1 to 4 carbon atoms,
R ^{1 represents} alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ² for hydrogen, amino or for alkyl, alkoxy, alkylthio substituted in each case optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl , Alkylamino or di alkylamino each having 1 to 6 carbon atoms in the alkyl groups,
Y represents cyano or nitro, and
Z represents in each case optionally substituted thienyl or benzothienyl,
where the possible substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, 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 - haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ - C ₄ alkyl-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino-carbonyl, C ₁ -C ₄ -alkylamino- sulfonyl, di (C ₁ -C ₄ alkyl) amino sulfonyl, phenyl are selected,
where the compounds N'-cyano-N- [1-methyl-3- (3-thienyl) propyl] ethanimide amide, N'-cyano-N- [1-ethyl-3- (3-thienyl) propyl ] -ethanimidamide, N'-cyano-N- [1-methyl-3- (2-thienyl) -propyl] -ethanimidamide, N'-cyano-N- [1- (2-thienyl) -ethyl] -ethanimidamide and N'-cyano-N- [1- (3-thienyl) ethyl] ethanimidamide (cf. DE-A-198 32 447) are excluded.

A, R ¹ , R ² and the substituents listed for Z preferably have the preferred meanings indicated above.

Examples of the compounds of the general formula (I) according to the invention are listed in the groups below. Regardless of the individual formula representations are the connections sketched with them in each case possible E and Z isomers and their mixtures.  

Group 1

A, R ¹ , R ² and Y have, for example, the meanings listed in the table below.

Group 2

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 3

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 4

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 5

A, R ¹ R ² and Y have, for example, the meanings given above in Table 1 for group 1.

Group 6

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 7

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 8

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 9

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 10

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 11

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 12

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 13

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 14

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 15

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 16

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 17

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 18

A, R ¹ , R2 and Y have, for example, the meanings given above in the table for group 1.

Group 19

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 20

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 21

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 22

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 23

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

Group 24

A, R ¹ , R ² and Y have, for example, the meanings given above for group 1 in the table.

The compounds of the general formula (I) are obtained if heterocyclyl amines of the general formula (II)

in which
A, R ¹ and Z have the meaning given above,
with imino compounds of the general formula (III)

in which
R ² and Y have the meaning given above and
X represents alkoxy or alkylthio,
if appropriate in the presence of a diluent.

If, for example, 1- (5-fluoro-2-thienyl) ethylamine and (dimethoxy methylenamino) - (nitrilo) methane are used as starting materials, the course of the reaction in the process according to the invention can be sketched using the following formula:

Formula (II) provides a general definition of the heterocyclylalkylamines 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 (II), A, R ¹ and Z preferably have those meanings which are already preferred above, in connection with the description of the compounds of the general formula (I), particularly preferred or very particularly preferred for A, R ¹ and Z have been given.

The heterocyclylalkylamines of the general formula (II) are known and / or can be prepared by processes known per se (cf. DE-A-197 44 232 / LeA 32589, DE-A-198 16 055).

Formula (III) provides a general definition of the imino 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 ² and Y preferably have those meanings which have already been given as preferred, particularly preferred or very particularly preferred for R ² and Y above in connection with the description of the compounds of the general formula (I) according to the invention ; X is in particular C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkyl thio, in particular methoxy, ethoxy, methylthio or ethylthio.

The imino compounds of the general formula (III) are known and / or can can be produced by processes known per se (cf. Chem. Ber. 100 (1967), 2604-2615; J. Am. Chem. Soc. 76 (1954), 1877-1879; J. Org. Chem. 26 (1961), 3347-3350; 10c. cit. 28 (1963), 1816-1821; 10c. cit. 35: 2067-2069 (1970); Synthesis 1975, 332-334; Tetrahedron Lett. 1968, 5523-5526; US-A-3910928).

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. As a diluent for carrying out the method according to the invention In addition to water, inert organic solvents are particularly suitable. These include in particular aliphatic, alicyclic or aromatic, given if halogenated hydrocarbons, such as 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, propio nitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacet amide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric acid triamid; 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 mono methyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at 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 leads. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar to lead.

To carry out the process according to the invention, the starting materials in 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 were carried out a reaction auxiliary, and the reaction mixture is in space agitated several hours at the required temperature. The on work is carried out according to customary methods (cf. games).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. used in the following plants:
Dicot weeds of the genera:
Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippernia, Rorippa, Rorippa, Rorippa Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera:
Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocot weeds of the genera:
Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischatenumum, Ischaeaeaum Agrostis, Alopecurus, Apera, Aegilops, Phalaris.
Monocot cultures of the genera:
Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, 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 crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.  

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, ie emulsifiers and / or dispersants and / or foam generating means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and 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 foam  Generating funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates as well as protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite leach and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are 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), Benfuresate, Bensulfuron (-methyl) Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac- (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chloromoxy, Chlo methoxy, Chlo methoxy Chloridazon, Chlorimuron (-ethyl), Chloronitrofen, Chlor sulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra sulfuron (-mor -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, dimepiperate, di methachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, fenobenz- 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), Fluridone, Fluroxypyr (-methyl), Fluroxone , Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamoxethapyr, Imazamoxapyr , Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, Iodosulfuron (-methyl, - sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobromuronachon, Metobenzuriaz uron, Metobromurol Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, Neburon, Nicosulfüron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxa diazon, Oxasulfuron, Oxazicfluomalinone, Oxazicfluomalone, Paraz , Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primi sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfenzoxoxy, Oxen, Methyl , Pyributicarb, Pyridate, Pyriminobac (- methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine , Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosuliron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thia fluamide, Thiazopyr, Thidiazimin, Thifensulfuron (tri-carboxylate), tri-benzyl, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-oxy-tri-oxy-tri-benzo-tri , Triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin and triflusulfuron.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.  

Manufacturing examples

example 1

2.0 g (20 mmol) of N-cyano-thiolimidoacetic acid methyl ester become one Mixture of 2.0 g (20 mmol) of 1- (3-thienyl) ethylamine (racemic) and 60 ml Added methanol, and the reaction mixture is 15 hours at room temperature (about 20 ° C) stirred. The solvent is then removed under reduced pressure carefully distilled off.

3.9 g (100% of theory) of N'-cyano-N- [1- (3-thienyl) ethyl] ethanimide are obtained amide (racemate) as an amorphous residue with refractive index n 20 | D = 1.5572.

Example 2

A mixture of 2.0 g (20 mmol) of 1- (3-thienyl) ethylamine (racemic), 2.7 g (20 mmol) of S-methyl-N-nitro-isothiourea and 80 ml of ethanol is under for 8 hours Reflux heated. After cooling, the crystalline product is removed by Ab suck isolated.

3.1 g (72% of theory) of N'-nitro-N- [1- (3-thienyl) ethyl] guanidine are obtained (Racemate) melting point 167 ° C.  

Example 3

A mixture of 3.4 g (20 mmol) of S- [1-ethyl-3- (2-thienyl) propyl] amine, 2.9 g (20 mmol) of dimethyl N-cyano-dithiocarbonimidate and 50 ml of acetonitrile becomes 2 Heated under reflux for hours. After cooling, the mixture with 80 ml Diluted water and then shaken with methylene chloride. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is in the Water jet vacuum concentrated, the residue digested with ligroin and that crystalline product isolated by suction.

4.2 g (78% of theory) of 2 - ((3S) -3 - {[(cyanoimino) - (methylsulfanyl) - methyl] amino} pentyl) thiophene with a melting point of 104 ° C.

Example 4

A mixture of 1.7 g (10 mmol) of 1-ethyl-3- (2-thienyl) propylamine (racemic), 1.2 g (10 mmol) (dimethoxymethylene amino) - (nitrilo) methane and 60 ml methanol is stirred for 18 hours at room temperature (approx. 20 ° C). Then that will The solvent is carefully distilled off under reduced pressure.

2.4 g (96% of theory) of 2- (3 - {[(cyanoimino) - (methoxy) -methyl] - amino} -pentyl) thiophene (racemate) as an amorphous residue from the refractive index n 20 | D = 1.5400.  

Analogously to Examples 1 to 4 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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. AB 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 with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the Retention times through linear interpolation between two consecutive Alkanones).

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

Starting materials of formula (II)

Example (II-1)

step 1

150 ml of formic acid are added dropwise at 140 ° C to 160 ° C with stirring a mixture of 100 g (079 mol) of 2-acetylthiophene and 300 ml of formamide give, and the reaction mixture is stirred at 160 ° C for 2 hours. After Ab cool to room temperature with toluene to about twice the volume thin, washed twice with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum. 78 g (64% of theory) of N- (1-thien-2-yl-ethyl) -formamide (racemate) are obtained as amorphous residue.

Level 2

A mixture of 75 g (0.48 mol) of N- (1-thien-2-yl-ethyl) -formamide, 120 ml of conc. Hydrochloric acid and 50 ml of water are heated under reflux for 3 hours and then concentrated in a water jet vacuum. The residue is washed with water / methylene chloride shaken, the aqueous phase made alkaline with 2N sodium hydroxide solution and with toluene  shaken. The toluene phase is dried with sodium sulfate and filtered. The Filtrate is worked up by distillation under reduced pressure.

24.8 g (41% of theory) of 1- (thien-2-yl) ethylamine (racemate) are obtained Boiling point 40 ° C at 0.8 mbar.

Example (II-2)

A mixture of 160 g (1.25 mol) of 1- (thien-2-yl) ethylamine (racemate), 140 g Methyl methoxyacetate, 15 g novenzym 435 and 1 liter methyl t-butyl ether becomes 24 hours and after the addition of a further 5 g of Novenzym-435 another 24 Stirred at 60 ° C for hours. Then it is filtered, the filtrate in a water jet concentrated in vacuo, the residue taken up in 500 ml dichloromethane and with 1 Liter of 10% aqueous hydrochloric acid shaken. The organic phase is separated off and worked up as described below. The aqueous phase is through Addition of conc. Sodium hydroxide solution made alkaline and extracted with dichloromethane. The organic extraction solution is dried with sodium sulfate and filtered. The desired product is removed from the filtrate by distillation under reduced pressure Pressure isolated.

35.5 g (44% of theory) of S-1- (2-thienyl) ethylamine are obtained from the boiling point 50 ° C (at 0.8 mbar).

The one separated in the workup after the reaction described above organic phase is dried with sodium sulfate and filtered. From the filtrate the solvent is carefully distilled off under reduced pressure. You get on  this way 100 g (84% of theory) of R- (N-methoxyacetyl) -1- (2-thienyl) ethylamine as a solid residue, which melts at approx. 30 ° C.

60 g (0.30 mol) of R- (N-methoxyacetyl) -1- (2-thienyl) ethylamine are mixed with 200 ml Water and 200 ml conc. Hydrochloric acid heated under reflux for 8 hours. After Ab cooling is extracted with diethyl ether and the organic phase by distillation worked up under reduced pressure.

28.5 g (75% of theory) of R-1- (2-thienyl) ethylamine are obtained from the boiling point 55 ° C (at 2 mbar).

Example (II-3)

A mixture of 9.8 g (50 mmol) of N- (1-methyl-4- (thien-2-yl) butyl) formamide, 100 ml conc. Hydrochloric acid and 40 ml of water are heated under reflux for 90 minutes. It is then largely concentrated in a water jet vacuum and the residue stirred with diethyl ether. The ether phase is decanted off and the residue is removed the solvent is carefully distilled off in a water jet vacuum.

8.5 g (83% of theory) of 2-amino-5- (thien-2-yl) pentane hydrochloride are obtained as dark oil.

Analogously to Examples II-1 to II-3, for example the compounds of the general formula (II) listed in Table 2 below can also be prepared.

Table 2

Examples of the compounds of the formula (II)

Examples of use Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is sprayed with the active ingredient preparation so that the ge desired amount of active ingredient is applied per unit area. The concentration the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired amount of active ingredient is 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 annihilation

In this test, for example, the compounds according to preparation example 5 show and 18 with good tolerance to crops, such as. B. corn, Soy and wheat, powerful weed control.  

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, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5-15 cm have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l 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 annihilation

In this test, for example, the compounds according to preparation example 5 show and 44 with partially good tolerance to crops, such as. B. barley, Corn and wheat, strong weed control.

Claims (8)

1. Use of N-substituted heterocyclylalkylamines of the general formula (I)
in which
A represents a single bond or alkanediyl,
R ^{1 represents} optionally substituted alkyl,
R ^{2 represents} hydrogen, amino or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
Y stands for cyano or nitro and
Z represents optionally substituted heterocyclyl,
to control unwanted plants. 2. Use according to claim 1, characterized in that
A represents a single bond or alkanediyl having 1 to 4 carbon atoms,
R ¹ represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ^{2 represents} hydrogen, amino or alkyl, alkoxy which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, Alkylthio, alkyl amino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups and
Z for an optionally substituted, monocyclic or bicyclic heterocyclic grouping from the series furyl, tetrahydrofuryl, benzofuryl, isobenzofuryl, thienyl, tetrahydro thienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, iso-indolylolol, iso-indolylol Benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl,
where the substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, 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 haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ - alkyl-carbonyl, C ₁ -C ₄ alkoxy-carbonyl, C ₁ -C ₄ alkylamino-carbonyl, di- (C ₁ -C ₄ alkyl) -amino-carbonyl, C ₁ -C ₄ -alkylamino- sulfonyl, di (C ₁ -C ₄ alkyl) amino sulfonyl, phenyl are selected. 3. Use according to claim 1 or 2, characterized in that
A for a single bond, for methylene (-CH ₂ -), dimethylene (ethane-1,2-diyl, -CH ₂ CH ₂ -), ethylidene (ethane-1,1-diyl, -CH (CH ₃ ) -) , Tri methylene (propane-1,3-diyl, -CH ₂ CH ₂ CH ₂ -) or propane-1,2-diyl (- CHzCH (CH ₃ ) -),
R ¹ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ² for hydrogen, amino, for each methyl, ethyl, n- or i-propyl, n-, i-, optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s - or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino and
Z for an optionally substituted, monocyclic or bicyclic heterocyclic grouping from the series furyl, tetrahydrofuryl, benzofuryl, isobenzofuryl, thienyl, tetrahydro thienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, iso-indolylolol, iso-indolylol Benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl,
where the substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t -Butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propyloxy, nyl-, propyloxy, n- n- or i-propoxy carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino carbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, phenyl are selected. 4. Use according to one of claims 1 to 3, characterized in that
A stands for a single bond or for dimethylene (-CH ₂ CH ₂ -),
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ² for hydrogen Amino, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino , Dimethyl amino or diethylamino and
Z represents in each case optionally substituted thienyl or benzothienyl,
where the substituents from the series nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethyl sulfinyl, methylsulfonyl, ethylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl, nylsulfonyl or Tri fluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl are selected. 5. N-substituted heterocyclylalkylamines of the general formula (I)
in which
A represents a single bond or alkanediyl having 1 to 4 carbon atoms,
R ¹ represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ^{2 represents} hydrogen, amino or alkyl, alkoxy which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl , Alkylthio, alkyl amino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups,
Y represents cyano or nitro, and
Z represents in each case optionally substituted thienyl or benzothienyl,
where the possible substituents from the series nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, 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 haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - haloalkylsulfinyl, C2 -C ₄ alkylsulfonyl, C1 -C ₄ haloalkyl sulfonyl, C ₁ - C ₄ alkyl carbonyl, C1 -C ₄ alkoxy carbonyl, C ₁ -C ₄ alkyl amino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl, C ₁ -C ₄ alkylamino sulfonyl, di (C ₁ -C ₄ alkyl) amino sulfonyl, phenyl are selected,
where the compounds N'-cyano-N- [1-methyl-3- (3-thienyl) propyl] ethane imidamide, N'-cyano-N- [1-ethyl-3- (3-thienyl) propyl ] -ethanimidamide, N'- cyano-N- [1-methyl-3- (2-thienyl) propyl] -ethanimidamide, N ₁ -cyano-N- [1- (2-thienyl) -ethyl] -ethanimidamide and N'-cyano-N- [1- (3-thienyl) ethyl] ethane imidamide (cf. DE-A-198 32 447) are excluded. 6. Compounds according to claim 5, characterized in that A, R ¹ , R ² and the substituents listed for Z have the meanings given in claim 3 or 4. 7. A process for the preparation of compounds according to claim 5 or 6, characterized in that heterocyclylamines of the general formula (II)
in which
A, R ¹ and Z have the meaning given in claim 5 or 6, with imino compounds of the general formula (III)
in which
R ² and Y have the meaning given in claim 5 or 6 and
X represents alkoxy or alkylthio,
if appropriate in the presence of a diluent. 8. Herbicidal agent, characterized by the content of at least one A compound according to claim 5 or 6 and conventional extenders.