MXPA01011007A - Use of n-substituted heterocyclylalkylamines as herbicides and novel n-substituted thienylalkylamines. - 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, R1 represents optionally substituted alkyl, R2 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

USE OF N-SUBSTITUTED HETEROCICLILALQU1LAMINAS AS HERBICIDES AND NEW N-SUBSTITUTE TIENILALQUILAMINAS. Field of the invention. The invention relates to the use of N-substituted heterocyclylalkylamines as herbicides as well as to novel N-substituted thienylalkylamines and processes for their preparation. Description of the prior art. It is known that certain N-substituted heterocyclylalkylamines have insecticidal properties (see EP-A-364844, EP-A-418199, JP-A-08231524 - cited in Chem. Abstracts 125: 300813). However, nothing has been disclosed up to now about the herbicidal properties of such compounds. It is also known that certain substituted arylalkylguanidines can influence the growth of plants (see DE-A-3345281, US-A-4639268). Detailed description of the invention. It has been found that the N-substituted heterocyclylalkylamines of the general formula (I) wherein A means a single bond or means alkanediyl, R1 means substituted alkyl, if appropriate, R means hydrogen, amino or means alkyl, alkoxy, alkylthio, alkylamino REF: 133493 or dialkylamino substituted, if appropriate, Y means cyano or nitro and Z signifies substituted heterocyclyl, if appropriate, have a potent herbicidal activity. The saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl - even in combination with heteroatoms, such as in alkoxyls, as far as possible, respectively straight chain or branched chain. The optionally substituted radicals can be mono- or polysubstituted, the substituents being able to be the same or different, if appropriate, from a polysubstitution. The compounds of the general formula (I) according to the invention contain at least one carbon-nitrogen double bond and can therefore be present in various isomeric forms with the E and Z configuration. The invention relates both to the use of the individual isomeric forms with the E and Z configuration of the compounds of the general formula (I) as well as mixtures of these isomeric compounds. The compounds of the general formula (I) according to the invention contain at least one carbon atom substituted asymmetrically and can therefore be present in various enantiomeric forms (forms with the R and S configuration) or diastereomers. The invention relates to both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) as well as in the mixtures of these isomeric compounds.

The substituents or the preferred ranges of the residues present in the formulas described above and which will be described below, are described below. Preferably, A means a single bond or means alkanediyl having 1 to 4 carbon atoms. Preferably, R 1 represents alkyl with 1 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms. Preferably, R 2 represents hydrogen, amino or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted, where appropriate, by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms. Preferably, Z means a monocyclic or bicyclic, heterocyclic group, optionally substituted, of the series consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazil, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, the preferred substituents being selected from the series consisting of nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, alkyl having 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulphinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 atoms carbon, di- (C 1 -C 4 -alkyl) -amino-carbonyl, alkylaminosulfonyl with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) -amino-sulfonyl, phenyl. Particularly preferably, it means a single bond, means methylene (-CH2-), dimethylene (ethane-1,2-diyl, -CH2CH2-), ethylidene (ethanoyl-J-diyl, -CH (CH3) -), trimethylene (propane-1,3-diyl, -CH2CH2CH2-) or? ropano-l, 2-diyl (-CH2CH (CH3) -). R 1 is particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy. Particularly preferably, R 2 represents hydrogen, amino, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, 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 substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy, by ethoxy, by methylthio, by ethylthio, by methylisulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulphonyl. Particularly preferably, it means a heterocyclic, monocyclic or bicyclic group, optionally substituted, of the series consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, with particularly preferred substituents being selected from the series consisting of 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, fluorochloromethyl, methoxy, ethoxy, n- or -propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoridi lth, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethyl-sulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, phenyl. Very particularly preferably, it means a single bond or means dimethylene (-CH2CH2-). Very particularly preferably, R 1 is methyl, ethyl, n- or i-propyl. Very particularly preferably R2 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. Very particularly preferably, Z means thienyl or benzothienyl substituted, if appropriate, with the substituents being very particularly preferred from the series consisting of nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or -propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorochloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylisulfinyl, ethylsulfinyl, n - or i- propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, trifluoromethylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl. The definitions of the residues indicated above in general or in the preferred ranges are valid both for the final products of the formula (I) as well as, correspondingly, for the starting materials or for the intermediates required respectively for the obtaining. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated. According to the invention, the herbicidal use of the compounds of the formula (I) is preferred, in which a combination of the meanings indicated above is preferred.

According to the invention, the herbicidal use of the compounds of the formula (1), in which a combination of the abovementioned meanings is especially preferred, is particularly preferred. According to the invention, the herbicidal use of the compounds of the formula (I) is very particularly preferred, in which a combination of the meanings indicated above is very particularly preferred. A small part of the compounds of the general formula (I) is already known (see EP-A-364844, EP-A-418199, EP-A-483062, JP-A-08231524 - cited in Chem. Abstracts 125: 300813) or constitutes part of a previous application, but which, however, has not been published previously (see DE-A-19 832 447). A large part of the compounds of the general formula (I) however is not known from the literature. In this connection, the novel compounds of the general formula (I) in which Z means thienyl or benzothienyl substituted, respectively, should be mentioned in particular, the compounds mentioned in a previous application consisting of the N-cyano being considered as examples. -N- [l-Methyl-3- (3-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l-ethyl-3- (3-thienyl) -propyl] -ethanoimidoamide, N'-cyano -N- [l-methyl-3- (2-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l- (2-thienyl) -ethyl] -ethanoimidoamide and N'-cyano-N - [l- (3-thienyl) -ethyl] -ethanoimidoamide (see DE-A-19 832 447). Thus, new compounds according to the invention are claimed as those compounds of the general formula (I), in which A means a single bond or means alkanediyl having 1 to 4 carbon atoms, R 1 means alkyl having 1 to 6 carbon atoms replaced if necessary per cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, amino, or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 6 carbon atoms in the alkyl groups, respectively substituted by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, Y means cyano or nitro, Z means thienyl or benzothienyl respectively substituted, The possible substituents of the series consisting of nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, alkyl having 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms being chosen , halogenalkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 atoms 15 carbon, alkylsulfinyl with 1 to 4 carbon atoms, halogenoalkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms; (C 1 -C 4 -alkyl) -amino-carbonyl, alkylaminosulfonyl with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) -amino-sulfonyl, phenyl, the N-compounds being excluded -cyano-N- [l-methyl-3- (3-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l-ethyl-3- (3-thienyl) -propyl] -ethanoimidoamide, 25 N'-cyano-N- [l-methyl-3- (2-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l- Ü, (2-thienyl) -ethyl] -ethanoimidoamide and N'-cyano-N- [1- (3-thienyl) -ethyl] -ethanoimido-amide (see DE-A-19 832 447). The substituents A, R \ R2 and those indicated for Z preferably have the preferred meanings indicated above. Examples of compounds according to the invention of the general formula (I) have been indicated in the following groups. Independently of the individual representations by means of formulas, the compounds schematized by them are constituted by the possible E and Z isomers, as well as by their mixtures. Group 1.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the following table. 10 15 20 25? É3X 10 15 20 25 Group 2.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 3.

In this case A, R \ R2 and Y have, by way of example, the meanings indicated in the table for group 1.

Group 4.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 5.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. 15 Group 6.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. > «Y'yi 'Group 7.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 8.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 9.

In this case A, R \ R2 and Y have, by way of example, the meanings indicated in the table for group 1.

Group 10 In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 11.

In this case A, R ', R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 12.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1.

Group 13 In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 14.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. 15 Group 15.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1.

-? Group 16 In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 17.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 18.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1.

Group 19 In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 20. , < In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 21.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. 5 r ^.

Group 22 In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 23.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. Group 24.

In this case A, R1, R2 and Y have, by way of example, the meanings indicated in the table for group 1. The compounds of the general formula (I) are obtained, if heterocyclylamines of the general formula (II) are reacted ) R1 sAN-H (II), I H wherein A, R1 and Z have the meaning indicated above, with imino compounds of the general formula (III) wherein R2 and Y have the meaning indicated above and X means alkoxy or alkylthio, in the presence of a diluent. If, for example, l- (5-fluoro-2-thienyl) -ethylamine and (dimethoxy-methyleneamino) - (nitrile) -methane are used as starting materials, the development of the reaction of the process according to invention by means of the following formula scheme: The heterocyclylalkylamines, to be used as starting materials in the process according to the invention, for the preparation of the compounds of the general formula (I) are generally defined by means of formula (II). In the general formula (II)), A, R 'and Z preferably have those meanings which have already been mentioned above as preferred, as being especially preferred or very particularly preferred for A, R1 and Z in relation to the description of the compounds of the general formula (I). The heterocyclylalkylamines of the general formula (II) are known and / or can be prepared by processes known per se (cf. DE-A-19744232 / LeA 32589, DE-A-19816055). The imino compounds to be further used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) are generally defined by the formula (III). In the general formula (III), R2 and Y preferably have those meanings which have already been mentioned above as preferred, as being especially preferred or very particularly preferred for R2 and Y in relation to the description of the compounds according to the invention of the formula general (I); especially X means alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms, especially means methoxy, ethoxy, methyl or ethylthio. The imino compounds of the general formula (III) are known and / or can be prepared according to 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; loc. Cit. 28 (1963), 1816-1821; loe cit. 35 (1970), 2067-2069; 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. Suitable diluents for carrying out the process according to the invention are, in addition to water, primarily inert organic solvents. These include, in particular, the aliphatic, alicyclic or aromatic hydrocarbons, if appropriate halogenated such as, for example, benzene, 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-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorustriamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethisulfoxide; alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water. The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures between 0 ° C and 150 ° C, and preferably between 10 ° C and 120 ° C. The process according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out the process according to the invention at a higher pressure or at a lower pressure, generally between 0.1 bar and 10 bar. For carrying out the process according to the invention, the starting materials will generally be used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is carried out, in general, in a suitable diluent in the presence of an auxiliary agent of the reaction and the reaction mixture is stirred, in general, for several hours at the necessary temperature. The processing is carried out according to usual methods (see the preparation examples). The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as weed killers. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances, according to the The invention, whether they 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: Dicotyledonous weeds of the following types: Sinapis Lepidium, Galium, Stellaria, 15 Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex , Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. 20 Dicot crops of the classes; Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the kinds; Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, 25 Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, ? .- J Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The active compounds according to the invention are suitable, depending on the concentration, for totally combating weeds, for example, in industrial and road installations and on roads and squares, with and without tree growth. In the same way, compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in mono-annual crops. The compounds according to the invention of the formula (I) show a potent herbicidal activity and a broad spectrum of activity on the ground and on the aerial parts of the plants. They are also suitable to some extent to selectively control monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the pre-emergence procedure and in the post-emergence procedure. To a certain extent, the compounds of the general formula (I), according to the invention, also show a potent effect against animal pests, especially against nematodes.

All plants and parts of plants can be treated according to the invention. By plants, all plants and plant populations, such as desired and unwanted wild plants (including crop plants of natural origin), will be understood in this case. The crop plants can be plants that can be obtained by conventional methods and cultivation and optimization or by means of biotechnological and genetic engineering methods, including transgenic plants and including plant varieties that can be protected or not through the right of protection of plant varieties. By parts of the plants should be understood all parts and aerial and underground organs of plants, such as shoots, leaves, flowers and roots, can be indicated in an exemplary way leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds as well as roots, tubers and rhizomes. The harvests as well as vegetative and generative reproductive material, for example seedlings, tubers, rhizomes, layering and seeds, also belong to the parts of the plants. The treatment according to the invention of plants and parts of the plants with the active products is carried out directly or by action on the locality, on the environment or in the storage enclosure according to the usual treatment methods, for example by immersion, spraying, evaporation, nebulization, spreading, application by brush and in the case of the reproduction material, especially in the case of seeds , widely by means of coatings with one or several layers. The active ingredients can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly suitable liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane. , or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethisulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed , aluminum oxide and silicates, as solid excipients for granulates come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; as emulsifiers and / or foam generators come into consideration: for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as albumin hydrolysates; as dispersants they come into consideration: for example, sulfitic leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids can be used in the formulations. . Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between OJ up to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be presented as such or in their formulations also in mixtures with known herbicides and / or with products which improve the compatibility with the crop ps ("protectors") for the control against weeds, being possible formulations ready for use or tank mixes. Thus, mixtures with agents for controlling weeds, which contain one or more known herbicides and a protector are also possible. For the mixtures, known herbicides are suitable, for example: Acetochlor, Aciflufen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, BAS-662H, Benazolin (-ethyl), Benfuresate, Bensulfuron ( -methyl), Bentazon, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Conidon (-ethyl) Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (- methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperat e, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl) ), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flupyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide , Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr , Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, I Soproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon , Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, pelargonic acid, Pendimethalin, Pendralin, Pentoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P -ethyl), Quizalofop (-P-tefuril), Rimsulfon, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin, Trifloxysulfuron, Triflusulfuron (-methyl) and Triflusulfuron. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground. The active compounds can be used as such, in the form of their formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated into the soil before sowing. The amount of active product used can vary within a wide range. This depends fundamentally on the type of the desired effect. In general, The amounts used are between 1 g and 10 kg of active product per hectare of soil surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active substances according to the invention are deduced from the following examples. Preparation examples: Example 1. 0 2.0 g (20 mmol) of methyl N-cyano-thiolimidoacetate are added to a mixture consisting of 2.0 g (20 mmol) of 1- (3-thienyl) -ethylamine (racemic) and 60 ml of methanol. and the reaction mixture is stirred for 15 hours at room temperature (about 20 ° C). The solvent is then carefully distilled off under reduced pressure. 5 3.9 g (100% of the theory) of N'-cyano-N- [l- (3-thienyl) -ethyl] -ethanoimidoamide (racemate) are obtained as an amorphous residue with a refractive index n20D = 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 is heated at reflux for 8 hours. -isotiourea and 80 ml of ethanol. After cooling, the precipitated crystalline product is isolated by suction. 3J g (72% of theory) of N'-nitro-N- [1- (3-thienyl) -ethyl] -guanidine (racemate) with a melting point of 167 ° C are obtained. 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 N is refluxed for 2 hours. dimethyldialdecycarbonimidate and 50 ml of acetonitrile. After cooling, the mixture is diluted with 80 ml of water and then shaken with methylene chloride. The organic phase is separated, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation in vacuo of the water tube, the residue is digested with Hgroin and the precipitated crystalline product is isolated by suction filtration. 4.2 g (78% of theory) of 2 - ((3S) -3- { [(Cyanoimino) - (methylsulfanyl) -methyl] -amino.}. -pentyl) -thiophene are obtained with a dot of fusion of 104 ° C. Example 4 A mixture of 1.7 g (10 mmol) of l-ethyl-3- (2-thienyl) -propyl-amine (racemic) is stirred for 18 hours at room temperature (approximately 20 [deg.] C.), 1.2 g (10 mmol) of (dimethoxymethyleneamino) - (nitrile) -methane and 60 ml of methanol The solvent is then carefully distilled off under reduced pressure. 2.4 g (96% of theory) of 2- (3. {[[(Cyanoimino) - (methoxy) -methyl] -amino}. -pentyl) -thiophene (racemate) are obtained as a residue amorphous with a refractive index n20D = 1.5400. In a manner analogous to that of Examples 1 to 4, and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) indicated in Table 1 below.

Table 1: Examples of compounds of the formula (I). 10 15 0 5 * - •, The determination of the logP values indicated in Table 1 was carried out according to EEC Directive 79/831 annex V A8 by HPLC (high performance liquid chromatography) on a phase reversed column (C 18). Temperature: 43 ° C. (a) Eluents for the determination in the acid range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrilb to 90% acetonitrile - the corresponding measurement results have been marked in table 1 with a). (b) Eluents for determination in the neutral range: 0.01 molar aqueous solution of phosphate buffer, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - the corresponding measurement results have been marked in table 1 with b). The calibration was carried out with unbranched alkane-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two successive alkanones). The lambda-maximum values were determined by means of the spectra of UV with 200 nm to 400 nm at the maximum of the chromatography signals. j Starting products of the formula (II): Example (II-1).

First stage. 150 ml of formic acid are added, at 140 ° C to 160 ° C, dropwise, with stirring, to a mixture consisting of 100 g (0.79 mol) of 2-acetyl-thiophene and 300 ml of formamide and the The reaction mixture is stirred for 2 hours at 160 ° C. After cooling to room temperature, it is diluted with toluene to approximately twice the volume, washed twice with water, dried over sodium sulfate and filtered. The solvent is carefully removed by distillation of the filtrate under vacuum from the water pump. 78 g (64% of theory) of N- (1-thien-2-yl-ethyl) -formamide (racemate) are obtained as an amorphous residue.

Second stage.

A mixture of 75 g (0.48 mol) of N- (1-thien-2-yl-ethyl) -formamide, 120 ml of concentrated hydrochloric acid and 50 ml of water is heated at reflux for 3 hours and then concentrates by evaporation to the vacuum of the water pump. The residue is shaken with water / methylene chloride, the aqueous phase is made alkaline with 2N sodium hydroxide solution and shaken with toluene. 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 l- (thien-2-yl) -ethylamine (racemate) are obtained, with a boiling point of 40 ° C to 0.8 mbar. Example (II-2).

A mixture of 160 g (1.25 mol) of l- (thien-2-yl) -ethylamine (racemate), 140 g of methoxyacetate of methyl, 15 g of Novenzym-435 and 1 liter of water is stirred for 24 hours. methyl-t-butyl ether and, after addition of another 5 g of Novenzym-435, is stirred for another 24 hours at 60 ° C. It is then filtered, the filtrate is concentrated by evaporation under vacuum of the water pump, the residue is taken up in 500 ml of dichloromethane and shaken with 1 liter of hydrochloric acid. watery to 10%. The organic phase is separated and further processed as described below. The aqueous phase is made alkaline by the addition of concentrated sodium hydroxide solution and extracted with dichloromethane. The organic extraction solution is dried with sodium sulfate and filtered. The desired product is isolated from the filtrate by distillation under reduced pressure. 35.5 g (44% of theory) of S-1- (2-thienyl) -ethylamine with a boiling point of 50 ° C (at 0.8 mbar) are obtained. The organic phase separated during work-up after the reaction described above is dried with sodium sulfate and filtered. The solvent is carefully removed by distillation of the filtrate under reduced pressure. In this way, 100 g (84% of the theory) of R- (N-methoxyacetyl) -l- (2-thienyl) -ethylamine is obtained as a solid residue, which melts at approximately 30 ° C. 60 g (0.30 mol) of the R- (N-methoxy-acetyl) -l- (2-thienyl) -ethylamine in 200 ml of water and 200 ml of concentrated hydrochloric acid are heated at reflux for 8 hours. After cooling, it is extracted with diethyl ether and the organic phase is worked up by distillation under reduced pressure. 28.5 g (75% of the theory) of R-l- (2-thienyl) -ethylamine with a boiling point of 55 ° C (at 2 mbar) are obtained. Example (II-3).

A mixture of 9.8 g (50 mmol) of N- (1-methyl-4- (thien-2-yl) -butyl) -formamide, 100 ml of concentrated hydrochloric acid and 100 ml of concentrated hydrochloric acid is heated to reflux for 90 minutes. ml of water. It is then concentrated by evaporation under vacuum of the water pump and the residue is stirred with diethyl ether. The ether phase is separated by decantation and the solvent is removed carefully under vacuum from the water tube by distillation of the residue. 8.5 g (83% of theory) of 2-amino-5- (thien-2-yl) -pentane hydrochloride as dark oil are obtained. Analogously to examples II-1 to II-3, for example, the compounds of the general formula (II) indicated in the following table can also be prepared.

(II).

Table 2: Examples of compounds of the formula (II). 10 15 20 25 Application examples: Example A. Pre-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds are sown from the test plants in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active product in such a way that the desired amount of active compound per unit area is applied respectively. The concentration of the spray mixture will be chosen in such a way that it is applied in 1,000 liters of water per hectare, respectively, the amount of desired active product. After three weeks the degree of damage of the plants in% damage is evaluated in comparison with the development of control not treated. They mean: 0% = no effect (same as untreated controls). 100% = total destruction. In this test, for example, the compounds according to Preparation Examples 5 and 18 show a partially good compatibility with crop plants, such as, for example, corn, soybean and wheat, a potent effect against weeds .

Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Test plants are sprayed, which have a height of 5 to 15 cm with the preparation of the active product, so that, respectively, the desired quantities of active compound per unit area are applied. The concentration of the sprayable broths is chosen in such a way that the desired quantity in each case of active product is applied in 1,000 liters of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. They mean: 0% = no effect (same as the untreated controls). 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 5 and 44, with a partially good compatibility with the crop plants, such as, for example, barley, corn, and wheat, a potent effect against the bad herbs. It is noted that, with regard to this date, the best method known to the applicant, to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (1)

1. CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. Use of N-substituted heterocyclylalkylamines of the general formula (I) characterized in that A means a single bond or means alkanediyl, R1 means substituted alkyl, if appropriate, R2 means hydrogen, amino or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino respectively substituted, Y means cyano or nitro and z means substituted heterocyclyl if necessary, for the fight against undesirable plants. 2. Use according to claim 1, characterized in that A means a single bond or means alkanediyl having 1 to 4 carbon atoms, R1 means alkyl having 1 to 6 carbon atoms, optionally substituted by cyano, halogen or alkoxy with 1 to 4 carbon atoms, R 2 signifies hydrogen, amino or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted, where appropriate, by cyano, by halogen, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms and means a monocyclic or bicyclic, heterocyclic, substituted group if appropriate, from the series consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indole ilo, isoindolyl, pyrazolyl, indazyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, the substituents being selected from the series consisting of nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogen alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, halogen-alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -aminocarbonyl, a l-amino-sulfonyl with 1 to 4 carbon atoms, di- (with 1 to 4 carbon atoms) -amino-sulfonyl, phenyl. 3. Use according to claims 1 or 2, characterized in that it means a single bond, means methylene (-CH2-), dimethylene (etapfh ?,, 1, 59-1,2-diyl, -CH2CH2-), ethylidene (ethane-1,1-diol, -CH (CH3) -), trimethylene (propane-1,3-diyl, -CH2CH2CH2-) or propane-1,2-diyl (-CH2CH (CH3) -) R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or 5 by ethoxy, R2 means hydrogen, amino, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i -, 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 dipropyl-10 amino substituted respectively by cyano, by fluorine, by chlorine, by methoxy, by ethoxy, by methylthio, by ethylthio, by methylisulfinyl, by ethylsulfinyl, by methylsulfonyl or by ethylsulfonyl and means a heterocyclic, monocyclic or bicyclic group, optionally substituted, of the series consisting of furyl, tetrahydro furyl, benzofuryl, 15 dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolylindolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, the substituents being selected from the series consisting of 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, fluoride-chloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, 25 n- or i-propylthio, n-, i-, s- or t-butylthio, m 4 * t <; methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl, methylamino- carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethyl aminocarbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, phenyl. 4. Use according to one of claims 1 to 3, characterized in that A means a single bond or means dimethylene (-CH2CH2-), R1 means methyl, ethyl, n- or i-propyl, R2 means 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, and Z means thienyl or benzothienyl substituted, if appropriate, substituents of the series consisting of nitro, cyano, carbamoylOi thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, Fluoromethylmethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylisulfinyl, ethylsulphinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylisulfonyl, ethylsulfonyl, n - or i- propilsu lfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl. 5. N-Substituted Heterocyclylalkylamines of the general formula (I) characterized in that A means a single bond or means alkanediyl having 1 to 4 carbon atoms, R1 means alkyl having from 1 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, amino, or means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted respectively by cyano, by halogen, by alkoxy with 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, for alkylsulfinyl having 1 to 4 carbon atoms or for alkylsulphonyl with 1 to 4 carbon atoms, Y means cyano or nitro, and Z means thienyl or benzothienyl respectively substituted, optional substituents being chosen the series consisting of nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 atoms carbon, C 1 -C 4 alkoxy, C 1 -C 4 halogenoalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 halogenoalkyl, C 1 -C 4 alkylsulfinyl, haloalkyl sulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 4 carbon atoms, if HX alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino- carbonyl, alkylaminosulfonyl with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino-sulfonyl, phenyl, excluding the compounds N-cyano-N- [l-methyl-3- (3-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l-ethyl-3- (3-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l-methyl-3- (2-thienyl) -propyl] -ethanoimidoamide, N'-cyano-N- [l- (2-thienyl) -ethyl] -ethanoimidoamide and N'-cyano-N- [1- (3-thienyl) -ethyl] -etanoimido-10 amide (see DE-A-19 832 447). 6. Compounds according to claim 5, characterized in that A, R1, R2 and the substituents indicated for Z have the meanings indicated in claims 3 or 4. 7.- Procedure for obtaining the compounds according to? claims 5 or 6, characterized in that heterocyclylalkylamines of the general formula (II) are reacted 0 wherein A, R1 and Z have the meaning indicated in claims 5 or 6, with imino compounds of the general formula (III) 5 < - i í í. 4, i GÍ H Í ^ characterized in that R 'and Y have the meaning indicated in claims 5 or 6 and X means alkoxy or alkylthio, optionally in the presence of a diluent. 8. Herbicidal agent, characterized in that it has a content in at least one compound according to claims 5 or 6 and usual extenders. * - t t í 1 4 í * *