MXPA00008758A - 6-substituted 2,4-diamino-1,3,5-triazine derivatives having at least two asymmetrically substituted carbon atoms, the production thereof, and their use as herbicides - Google Patents

Abstract

The invention relates to substituted, optically active aminotriazines having at least two asymmetrically substituted carbon atoms of formula (I), in which A represents a single bond or each straight chained or branched alkandiyl or oxaalkandiyl;R1 represents amino, formylamino, or each alkylamino, dialkylamino, alkyl carbonyl amino, N-alkyl-N-alkyl carbonyl-amino, alkoxycarbonyl amino, N-alkyl-N-alkoxycarbonyl-amino, alkyl-aminoalkylide amino or dialkylamino alkylide amino which are optionally substituted by cyano, halogen or C1-C4-alkoxy;R2, R3 represent hydrogen, halogen or alkyl which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or R3 together with R2 represent alkandiyl which is optionally substituted by cyano, halogen, or C1-C4-alkyl;R4 represents alkyl or cycloalkyl;Y represents hydrogen, hydroxy, mercapto, amino, cyano, halogen or each alkyl, alkoxy, alkyl carbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, dialkylamino carbonyloxy, alkylthio, alkylamino or dialkylamino which are optionally substituted by cyano, halogen or C1-C4-alkoxy, and;Z represents a monocyclic or bicyclic carbocyclic or heterocyclic radicals which are optionally substituted. The substituents are provided with the provision that R2, R3 and Y are different from one another in each individual case, and that the substituents are bound on both carbon atoms, on which R2 and R3 or R4. R,R or R,S or S,R or S,S or R,rac or S,rac are configured [the first statement refers to the triazine-substituents -CR2R3Y, and the second statement refers to the amino-substituents -CHR4(A-Z)]. The invention also relates to a method for producing the compounds of formula (I) and to the utilization thereof as herbicides.

Description

DERIVATIVES OF 2, 4-DIAMINO-1, 3, 5-TRIAZINA 6- SUBSTITUTED WITH AT LEAST TWO ATOMS OF CARBO NO SUBSTITUTED ASYMMETRICS, ITS OBTAINING AND ITS EMPLOYMENT AS HERBICIDES FIELD OF THE INVENTION i • o-n refers to new optically active aminotriazines, substituted, with at least two carbon atoms substituted asymmetrically, to a procedure for obtaining them and their use as herbicides. Background of the Invention Substituted aminotriazines (patent) are already known from the literature (see J3S-3 816 419, US-3 932 167, EP-191 496, EP-273 328, EP-411 153 / WO 90/09 378, WO 97/00 -254, WO 97/08 156). However, these compounds - partly even with carbon atoms substituted asymmetrically - have not yet acquired any special significance. Detailed description of the invention. We have now found new optically active aminotriazines, substituted, with at least 2 carbon atoms substituted asymmetrically of the general formula (I), REF .: 122868 R1 where i A means a single bond or means alkanediyl or oxaalkanediyl, respectively of straight chain 3 branched chain, with respectively up to 6 carbon atoms, R 1 means amino, means formylamino or signi? Cant. alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonyl-amino, alkoxycarbonylamino, N-alkyl-N-alkoxycarbonylamino, alkylaminoalkylidenamino or dialkylaminoalkylideneamino with respectively up to 6 carbon atoms in the alkyl groups or in the alkylidene groups, substituted respectively by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, halogen or means alkyl with up to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 at 4 carbon atoms, R means hydrogen, halogen or alkyl with up to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or together with R2 means alkanediyl with 2 to 5 atoms of carbon, optionally substituted by cyano, by halogen or by alkyl with 1 to 1 ~ 4 carbon atoms, R4 means alkyl with up to 6 carbon atoms or means cycloalkyl uilo with 3 to 6 carbon atoms, Y means hydrogen, hydroxy, mercapto, amino, cyano, halogen, or means alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyl-thi, alkylthio, alkylamino or dialkylamino with respectively up to 6 atoms - of carbon in the alkyl groups, substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and Z means a monocyclic or bicyclic, carbocyclic or heterocyclic group, optionally substituted, of the series formed by cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofyl, dihydroisobenzoyl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, ox adiazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalyl, cinolinyl and phthalazinyl, the possible substituents being chosen, respectively, preferably from the following group: hydroxy, amino, cyano, nitro, carbamoyl , sulfamoyl, halogen, alkyl, alkoxy, alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, optionally substituted by hydroxy, by cyano or by halogen, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, alkylsulfinyl, alkylsul fonyl, alkylsulfonylamino, alkylaminosulfonyl or dialkylaminosulfonyl with 1 to 6 carbon atoms in the alkyl groupsare each substituted, where appropriate, by halogen, phenyl or phenoxy substituted, where appropriate, by hydroxy, by cyano, by nitro, by halogen, by alkyl having 1 to 4 carbon atoms, by halogen with 1 to 4 carbon atoms , by alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, as well as methylenedioxy or ethylenedioxy substituted respectively by halogen, provided that in each particular case, R2, R3 and Y they have to be different from each other and that the substituents on both carbon atoms, with which R2 and R3 or R4 are linked, have to be configured in the following manner: (a) R configuration at the carbon atom ' with which R2 and R3 are linked and R configuration at the carbon atom, with which R4 is linked ('diastereomers R, R'), (b) R configuration at the carbon atom, where R2 and R are linked; R3 and configuration S in the ato mo of carbon, with which R4 ('R, S diastereomers') is linked, (c) S configuration at the carbon atom, with which R2 and R3 are linked and R configuration at the carbon atom, in which is linked R ('diastereomers S, R'), (d) configuration S at the carbon atom, to which R2 and R3 are linked and configuration S at the carbon atom, to which R is linked ('S, S diastereomers "), (e) R configuration at the carbon atom, with which R2 and R3 are linked and racemic configuration at the carbon atom, with which R4 is linked (" R diastereomers, rae ") ), (f) S configuration at the carbon atom, with which R2 and R3 are bound and racemic configuration at the carbon atom, with which it is bound. ('diastereomers S, rae') Since the carbon atom, to which R2 and R3 and Y are linked or is present in racemic form, all the compounds according to the invention are therefore optically active. new aminotriazines substituted with at least 2 carbon atoms substituted asymmetrically of the general formula (I), if substituted biguanides of the general formula (II) are reacted) in which A, R1, R4 and Z have the meaning above indicated, - and / or adducts with acids of the compounds of the general formula (II) with (optically active) derivatives of carboxylic acids of the general formula (III) wherein R2, R3 and Y have the meaning indicated above and X means halogen or alkoxy, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent and, if appropriate, on the products of the general formula (1) / obtained in this way, other transformations according to usual methods within the scope of the above definition of the substituents. they can be converted, according to usual methods, "into other compounds of the general formula (I) according to the above definition of the substituents, for example by acylation of the compounds of the formula (I), wherein R 1 means amino and / or Y means hydroxyl, for example with acetyl chloride or with propionyl chloride, or, for example, by fluorination of the compounds of the formula (I), in which Y means hydroxyl, for example with diethylaminosulfur trifluoride ('DAST') -see the procurement examples-. The new substituted aminotriazines with at least 2 asymmetrically substituted carbon atoms of the formula (I) are characterized by a potent and selective herbicidal activity. To some extent they also have fungicidal and insecticidal activity.

In the definitions, 'the chains - hydrocarbons,. such as alkyl -even in combination with heteroatoms, such as alkoxy or alkylthio- are respectively straight-chain or branched chain. In general, halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially means fluorine or chlorine. The subject of the invention are preferably compounds of the formula (I), in which A means a single bond, means methylene (-CH2), dimethylene (ethane-1,2-diyl, -CH2CH2-Í) > ethylidene (ethane-1, 1-diyl, -CH (CH3) -), oxaet anodiyl (-CH20-), trimethylene '(propane-1,3-diyl, -CH2CH2CH2-), propylidene (propane-1,1-diyl, -CH (C2H5) -, propane-2, 3-diyl (-CH (CH3) CH2-), 2-methyl-propane-1,3-diyl (-CH2CH (CH3) CH2-), 3-oxa-propane - 1, 3-dii lo (-CH2CH20), 2-oxa-propane-1,3-diyl (-CH20CH2-), tetramethylene (butane-1,4-diyl, -CH2CH2CH2CH2-), butane-2, 4-diyl (CH (CH3) CH2CH2-), butane-2, 3-diyl (-CH (CH3) CH (CH3) -), 3-methyl-butane-2,4 -diyl (-CH (CH3) CH (CH3) CH2-), 4-oxa-butane-2,4-diyl (-CH (CH3) CH2-0-), pentane-3, 5-diyl (-CH ( C2H5) CH2CH2-), 5-oxa-pentane-3, 5-diyl (-CH (C2H5) CH20-), 4-oxa-pentane-2,5-diyl (-CH (CH3) CH2OCH2-) 5-oxa -hexane-3,6-diyl (-CH (C2H5) CH2OCH2-) R1 means amino, means formylamino or means methylamino, ethylamino, dimethylamino, acetylamino I, propionylamino, n- or i-butyroylamino, N-methyl-N-acetylamino , N-et-il-N-acetylamino, N-methyl-N-propionyl-amino, methoxy carbonyl amino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methyl 1-N-methoxycarbonyl-amino, N-ethyl-N- methoxy carbonyl-amino, N-met il-Ne toxicarbonyl-amino, methylaminomethyl enamino, ethylaminomethyl-1-enamyryl, -methylaminoethylidene, or dimethylaminomethylamino substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R2 means hydrogen, fluorine, chlorine, bromine, or means methyl, ethyl, - or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R3 means hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy or, together with R2, means dimethylene (ethane-1,2-diyl), trimethylene (propane-1,3-diyl) or tetramethylene (butane.-1,4-diyl) respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by bromine, by methyl or ethyl, 1 R4 means methyl, ethyl, n- or i-propyl, or means cyclopropyl, Y means hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n-? -propox? , n-butoxy, acetyloxy, propionyloxy, n- or i-butyloxyxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, and ylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethyl aminocarbonyloxy, methylthio , ethylthio, n- or i-propylthio, n-, i-, or s-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, or s-butylamino, or dimethylamino substituted respectively where appropriate by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and Z means a monocyclic or bicyclic, carbocyclic or heterocyclic group, optionally substituted, of the series consisting of cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl *,? dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinoline, isoquinolone, quinoxaline, cinolino or phthalacinyl,? The possible substituents being selected, respectively, preferably from the following group: hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino substituted, where appropriate, by hydroxy, by cyano, by fluorine or by chloro, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino. n- or i-butyroylamino, ethylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl,. methylthio, i-propylthio, n-, i-, s- or t-butyl-ethylsulfinyl, n- or i-propylsul finyl, methylsulfonyl, ethylsulphonyl, n- or i-propyl sulphonic, methylsulphonylamino, ethyl-sul phylamino, n- or i-propylsulphonylamino, methylaminosulphonyl, ethylaminosulphonyl, n- or i-propylaminosulphonyl, or dimethylaminosulphonyl, respectively, optionally substituted by fluorine and / or by chlorine, phenyl or phenoxy substituted respectively by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by difluoromethoxy or by trifluoromethoxy, as well as methylenedioxy or ethylenedioxy respectively substituted, if appropriate by fluorine and / or by chlorine, with the condition that in each particular case R2, 'R3 and Y are different from each other and from the substituents on the carbon atoms, with which R2 and R3 are linked or R4 is n configured as follows:) (a) R configuration in the carbon atom, with which R2 and R3 are linked and R configuration in the carbon atom, with which R4 is bound ('R, R diastereomers'), (b) R configuration at the carbon atom, where R2 and R3 are linked and S configuration at the carbon atom, to which R4 is linked ('diastereomers R, S "), * • (c) configuration S at the carbon atom, with which R2 and R3 are linked and R configuration at the carbon atom, where R4 ('diastereomers S, R') is linked, (d) S configuration at the carbon atom, to which R2 and R3 are linked and S configuration at the carbon atom, with which R4 ('diastereomers S, S') is linked, (e) R configuration at the carbon atom, with which R2 and R3 are linked and racemic configuration at the carbon atom, with which R4 ('diastereomers R, rae') is linked, (f) configuration S at the carbon atom, with which R2 and R3 are linked and configuration racemic on the carbon atom, with which R4 is linked ('diastereomers S, rae'). The invention relates especially to the compounds of the formula (I), in which A means a single bond, means dimethylene (ethane-1,2-diol, -CH2CH2-) oxaetanodii lo (-CH20-) or 2-oxa-propane-l, 3-diyl (-CH20CH2-), R1 means amino, means formylamino or means acetylamino, propionylamide, methoxycarbonylamino, ethoxycarbonyllamino or dimethylaminomethyl-amino substituted respectively by cyano, by fluorine, chlorine, methoxy or ethoxy, R2 means hydrogen, fluorine, chlorine or means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy R3 means hydrogen, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, or together with R, means dimethylene (ethane-1,2-diyl) substituted, where appropriate, by cyano, fluorine, chlorine or methyl, R 4 is methyl or ethyl, Y is hydrogen, hydroxyl, cyano, fluorine, chlorine, bromine or methyl. , ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, acetyloxy , propionyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy or dimethylaminocarbonyloxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and by 4; Z means a monocyclic or bicyclic, carbocyclic or heterocyclic group, optionally substituted, of the series consisting of phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzo thienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzo thienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinolino and phthalazinyl, the possible substrates being chosen, respectively, preferably from the following group:% f hydroxyl, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, dimethylamino, respectively substituted by hydroxy, by cyano, by fluorine or chlorine, acetyl, methoxycarbonyl, ethoxycarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulfinyl, methylsulfonyl, ilsulphonyl, or dimethylaminosul fonyl respectively substituted, if appropriate, by fluorine and / or or by chloro, phenyl or phenoxy substituted respectively by hydroxyl, by cyano, by nitro, by fluorine, by chlorine, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di-fluoro-toxy or trifluoromethoxy, as well as methylenedioxy or ethylenedioxy, respectively substituted, if appropriate, by fluorine and / or by chlorine, provided that in each particular case R2, R3 and Y are different from each other and that the substituents on the carbon atoms, with which R2 and R3 or R4 are linked, have the following configuration: (a) configuration R in the carbon atom, with which they are linked R2 and R3 and configuration R on the carbon atom, to which R4 is attached ('diastereomers R, R'), (b) R configuration at the carbon atom, where R2 and R3 are linked and S configuration at the carbon atom , with which R4 is linked ('diastereomers R, S "), s • (c) configuration S gn the carbon atom, to which R2 and R3 are linked and R configuration at the carbon atom, in which R4 ('S, R diastereomers') is linked, (d) S configuration in the carbon atom, to which R2 and R3 are linked and S configuration at the carbon atom, to which R4 is linked ('diastereomers S, S'), The definitions of the residues indicated above in general in the preferred ranges they are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the necessary intermediate products, respectively, for obtaining them. These definitions of the remains may arbitrarily be mutually exclusive, that is to say even preferred ranges indicated. Examples of compounds according to the invention of the general formula (I) are indicated in the following groups. Group 1.

In this case R1 means amino, formylamino, acetylamino, propionylamino or dimethylaminomet ileamino. The triazine substituent R2, R3 and Y in this case mean, by way of example, the following groups: -CH (CH3) "C2H5, -CH (CH3) C3H7-n, -CH (CH3) C3H7-i, -CH ( C2H5) C3H7-n, -CH (C2H5) C3H7-I, -C (CH3) (C2H5) C3H7-n, -C (CH3) (C2H5) C3H7-i -CH (OH) CH3. -CH (OH) C'2H5, -CH (OH) C3H7-n, -CH (OH) C3H7- i, • -CH (OCHO) CH3, # -CH (EIGHT) C2HS, -CH (EIGHT) C3H7-n, -CH (ECHO) C3H7-i, -CH (OCOCH3) CH3, -CH (0C0CH3) C2H5, -CH (0C0CH3) C3H7-n, -CH (OCOCH3) C3H7-i, -CH (OCOC2H5) CH3, -CH (OCOC3H7-n) CH3, -CH (OCOC3H7-i) CH3, -C (OH) (CH3) C2H5, -C (OH) (CH3) C3H7-n, -C ( OH) (CH3) C3H7-Í, -CH (SH) CH3, -CHBr'CH3, -CHBrC2H5, -CHBrC3H7_n, -CHBrC3H7-i, -CBr (CH3) C2H5, * ' -CBr (CH3) C3H7-n, -CBr (CH3) C3H7-Y, -CHCICH3, -CHC1C2H5, -CHClC3H7-n, -CHClC3H7-i, -CC1 (CH3) C2H5, -CC1 (CH3) C3H7-n, -CC1 (CH3) C3H7-i, -CHFCH3, -CHFC2H5, -CHFC3H7-n, -CHFC3H7-i, '-CF (CH3) C2H5 -CF (CH3) C3H7-n, -CF (CH3) C3H7-i, -CH (CF3) CH3, -CH (CF3) C2H5, -CH (CF3) C3H7-n, -CH (CF3) C3H7-i, -C (CF3) (CH3) C2H5, -C (CF3) (CH3) C3H7-n, -C (CF 3) (CH 3) C 3 H 7 -I, -CH (OH) CF 3, -C (OH) (CF 3) CH 3, -CF (OH) CF 3, -CH (CH 3) OCH 3, -CH (C 2 H 5) OCH 3, - -CH (C3H7-11) OCH3,. -CH (C3H7-i) OCH3, -C (CH3) (C2H5) OCH3, -C (CH3) (C3H7-n) OCH3, -C (CH3) (C3H7-Y) OCH3, -CH (CH3) OC2H5, -CH (C2H5) QC2H5, -CH (C3H7-n) OC2H5, -CH ( C3H7-Y) OC2H5, -CH (CH3) OC3H7-n, I -CH (CH3) OC3H7-Í, " -CH (C2H5) OC3H7-n, -CH (C2H5) OC3H-7-Í, '-CH (CF3) OCH3, -CH (CF3) OC2H5, -CHFCF3, -CHC1CF3, -CF (CH3) CF3, -CF (C2H5) CF3, -CF (C3H7-n) CF3, -CF (C3H7-i) CF3, -CH (CN) CH3 -CH (CN) C2H5, -CH (CN) C3H7-n, -CH (CN) C3H7-i, -C (CN) (CH3) C2H5, -C (CN) (CH3) C3H7-n, -C (CN) (CH3) C3H7-: n -CH (CH3) SCH3, -CH (C2H5) SCH3, -CH (C3H7-n) SCH3- '-CH (C3H7- i) SCH3, -C (CH3) (C2H5) SCH3, -C (CH3) (C3H7-n) SCH3, -C (CH3) (C3H7-i) SCH3, -CH (CH3) SC2H5, -CH (C2H5) SC2H5, -CH (C3H7-n) SC2H5, -CH (C3H7- i) SC2H5, -CHFBr, -CHFC1, -CFBrCH3, -CFCICH3, -CFBrCl, -CH (CH2C1) Cl, -CH (CH3) CH2OCH3, -CH (CH3) CH2OC2H5, -CH (C2H5) CH2OCH3, -CH (CH3) CH2CH2OCH3, CH, F CH, C! H, CH, CH. CH3 C2H5 Cla C2H5 CH3 C.H, CH3 For each of the examples indicated in this case and which will be indicated in the following groups and the definitions of the residues, the tereomeric forms described above will be especially preferred: (a) configuration R at the carbon atom , with which R2 and R3 are linked and R configuration at the carbon atom, with which R4 is linked ('diastereomers R, R'), (b) R configuration at the carbon atom, where R2 is linked and R3 and S configuration at the carbon atom, with which R4 ('R, S diastereomers') is linked, (c) S configuration at the carbon atom, with which R2 and R3 are linked and R configuration at the carbon atom, in which it is bound ('diastereomers S, R'), * (d) configuration S at the carbon atom, with which R2 and R3 are linked and S configuration at the carbon atom, to which R4 ('diastereomers S, S'), Group 2 is linked.

In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 3.

In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 4 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group-1 above. $ / Group 5.

In this case R1, • R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 6 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 7.

In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 8 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 9 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 10 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 11 R1 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 12 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 13 In this case R1, R2, R3 and Y have, for example, 'the meanings indicated in group 1 above.

Group 13a.

R In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 14 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 15 R1 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 16 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 17 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 18 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. (Group 19.

In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 20 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 21 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 22 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 23 In this case R1, R2, R3 and Y have, for example, the meanings indicated in the previous section. Group 24 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 25 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 26 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 27 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. t Group 28 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 5; 1 above. Group 29 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 30 In this case R1, R2, R3 and Y have, for example, the indicated meanings, in group 1 above. Group 31 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 32 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 33. 1 In this case R1, R2, R3 and Y have, for example, the meanings indicated in the group f I above. Group 34 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 35 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 36 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 37 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. ) Group 38 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 39 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 40 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 41 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 42 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 • previous.

Group 43 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 44 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 45 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 46 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 47 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. ) Group 48 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above. Group 49 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

Group 50 In this case R1, R2, R3 and Y have, for example, the meanings indicated in group 1 above.

If, for example, (S) -l- (1-phenyl-propyl) -biguanide and ethyl (S) -l-chloropropionate are used as starting materials, the development of the reaction can be schematized in the case of the process according to the invention by means of the following formula scheme: The substituted biguanides, to be used as starting materials, in the process according to the invention, for the preparation of the compounds of the formula (I), are generally defined by the formula (II). In the - formula (II), A ,. R1, R4 and Z preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably for A, R1, R4) and Z in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (II) are known and / or can be prepared according to known processes (cf. EP-509 544, US-3 816 419, US-3 860 648, WO 97/00 254, WO 97/08 156, DE-19 641 691 (Le A 31 995), DE-19 641 692 (Le A 32 037), DE-19 641 693 (Le AÍ31 975), 'Preparation examples). The derivatives of the carboxylic acids to be further used as starting materials in the process according to the invention are generally defined by the formula (III). In the formula (III), R.sup.2, R.sup.3 and Y preferably have or especially those meanings which have already been indicated above, preferably or particularly preferably for R.sup.2, R.sup.3 and Y in relation to the description of the compounds of the formula (I ) according to the invention; in this case X preferably means fluorine, chlorine, bromine or alkoxy having 1 to 4 carbon atoms, especially means methoxy or ethoxy. The starting materials of the general formula (III) are known and / or can be prepared according to known processes (see J. Chem. Soc. Per in Trans I, 1979, 2248-2252; Examples of preparation). The process according to the invention for the preparation of the compounds of the general formula (I). it is preferably carried out with the use of a reaction auxiliary agent. Suitable auxiliary agents of the reaction for the process according to the invention are, in general, the usual inorganic or organic acid bases or acceptors. These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals, such as, for example, sodium, potassium or calcium acetate, lithium amide, sodium acetate, of potassium or calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate , ethanolate, n- or i-propanolate, n-, i-, s- or sodium or potassium t-butanolate; also basic organic nitrogenous compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, et il-diisopropylamine, N, N-dimet ix-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl ina, N, N-dimethyl-aniline , N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3, 5 -dimet ilpyridine, 5-ethyl-2-met il-pir idina,4 - . 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2, 2, 2] -octane (DABCO), 1/5-diazabicyclo [4, 3, 0] -non-5-ene (DBN) or 1/8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU). The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out with the use of a diluent. Suitable diluents for carrying out the process according to the invention are, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic hydrocarbons, if appropriate halogenated, such as, for example, benzine, 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 met il-isobut il-ce tona; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacet amide, N-methyl-formanilide, N-methyl-pyrrole idone or hexamethyl phos forotriamid; esters such as methyl acetate or ethyl acetate; sulfoxides, such dimethyl sulfoxide; alcohols, such as methanol, ethanol, n- or i-propanol, et ilepgl icolmonomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, their mixtures 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, preferably between 10 ° C and 100 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under 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 are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is carried out, in general, in a suitable diluent in the presence of a reaction auxiliary agent and the reaction mixture is stirred, in general, for several hours at the necessary temperature. Working up is carried out by customary methods (see the procurement 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 invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: f Bad dicotyledonous herbs of the classes: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, E ex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus , Taraxacu? .- Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linu, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbris tyl is, Sagittaria, Eleocharis, Scirpus , Paspalum, lschaemum, Sphenoclea, Dactyloct enium, Agrostis, Alopecurus, Apera.Cultures of monocotyledonous classes: Ory'za, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is not, however, limited in any way to these classes, but extends in the same way also on other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in 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. of tea, rubber, oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in monoanal crops. The compounds according to the invention of the formula (I) are especially suitable for selectively controlling monocotyledonous and dicotyledonous weeds in monocotyledonous crops. and dicotyledons, both in the pre-emergence procedure and in the post-emergence procedure. The active compounds can be converted into customary formulations, such as solutions, emulsions, powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as micro-encapsulated in polymer materials. These formulations are prepared in a known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, if appropriate, using surfactants, that is, emulsifiers and / or dispersants. and / or foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: aromatic hydrocarbons, such as xylene, toluene, or alkyl-naphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, as cyclohexane, or parafams, for example, fractions of crude petroleum, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl tile ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water. * < Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmoril loni ta or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid. , aluminum oxide and silicates, as solid excipients for granulates are considered: 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 husk shells, corn ears and tobacco stems; . suitable emulsifiers and / or foam generators are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of polyoxyethylenated fatty acids, polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylaryl polyglycol ether, alkylsulphates, alkylsulfates, arylsulfonates, as well as albumin hydrolysates; as dispersants they come into consideration: for example, sulfitic leaching of lignin? and methylcellulose. In the formulations • 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 cephalins and lecithins, can be used; synthetic phospholipids. 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 contain, as a rule, between 0.1 to 95% by weight of active compound, preferably between 0.5 and 1. 90% The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides for combating weeds, ready-to-use preparations or tank mixtures being possible. For the mixtures are known herbicides, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, amidosulfuron, anilofos, Asulam, Atrazine, Azafenidin, Azimsul furon, benazolin (- ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium) Bromobutide, Bromo fenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl 1j, Clomazone, Clomep'rop, Clopyralid, Clopyrasul furon (-methyl), Cloransulam (methylo), Cumyluron, Cyanazine, Cycloate, Cyclosulfa uron, Cycloxydim, Cyhalo fop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Di ethatyl (-eti lo), Difenzoquat, Di flufenican, Di flufenzop ^ r, Dimefuron, Dimepiperate, Dimethachlor, Dimetha and tryn, Dime thenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethal flural in, Ethametsulfuron (-me ti lo), E thofumesate, Ethoxyfen, Ethoxysul furon, etobenzanid, fenoxaprop (-Pe linden), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Fl azasul furon, Fluazifop (-P-but i lo), Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flupyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (- eptyl), Flurprimidol, Flurtamon, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop I.-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazame thapyr, Ima zamox, lmazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, I soxapyri fop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metaitron, Metazachlor, Me thabenz thiazuron, Metobenzuron, Metobromuron, (alpha- ) Metolachlor, Metosulam, Metoxuron, Metribuzin, Met sul furon (-methyl), Molinate, monolinuron, naproanilide, Napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, Oxadiargyl, Oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, Pendime Thalin, pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-met yl), prometryn, propachlor, propanil, propaquizafop Propisochlor, propyzamide, prosulfocarb, prosulfuron, Pyra flufen (-ethyl), Pyrazolate, Pyrazosul furon (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-p-tefuril), Rimsul furon, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sul fometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiaf luamide, Thiazopyr, Thidiazimin, Thifensulfuron (-met ilo), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-met ilo), Triclopyr, Tridiphane, Trifluralin and Tri flusulfuron. t a mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, plant nutrient substances and agents which improve soil structure, it is also possible. The active products 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 land surface, preferably between 5 g: and 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.

A solution of 2.4 g (44 mmol) of sodium methylate in 10 ml of methanol is added dropwise, under stirring, at 20 ° C, to a mixture consisting of 9.7 g (40 mmol) of (S) ) -1- (1-phenyl-ethyl) -biguanide, 4.5 g (40 mmol) of ethyl (R) lactate Ile and 80 ml of methanol and the reaction mixture is stirred for another 15 hours at room temperature (about 20 hours). ° C). It is then diluted to a volume approximately three times greater with an approximately equal amount of methylene chloride and water, after shaking the organic phase is separated, washed with water, dried with sodium sulfate and filtered. The solvent is carefully removed by distillation of the filtrate in the vacuum of the water pump. 4.4 g (42% of theory) of 2-amino-4- (R) - (1-hydroxyethyl) -6- (S) - (1-phenylethyl-amino) -1,3,5-triazine are obtained in the form of amorphous residue. [a] 20D = 93.5 ° C.

In a manner analogous to that of the preparation example 1 and according to the general description of the preparation process according to the invention, for example, the compounds of the formula (I) indicated in the following table 1 can also be prepared. The stoichiometric data (relative to the characterization of the types of have been given therein as definition of the compounds of the formula (I) with the abbreviations R, R or R, S or S, R or S, S or R, rae or S, rac, ie the first indication refers respectively to the substituents of the triazines -CR2R3Y and the second indication refers to the substituents of the a-CHR4 (AZ).

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

Table 1: Continuation.

Table ^: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation.

Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1: Continuation.

Table 1: Continuation Table JL: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation Table 1: Continuation.

Table 1; Continuation.

Table 1: Continuation The determination of the logP values indicated in Table 1 or the one carried out according to EEC Directive 79/831 annex V.A8 by HPLC (high resolution liquid chromatography) in a column with phase inversion (C18). Temperature: 43 ° C. (a) Eluents for the determination in the acid range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile 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 1 * carbon atoms>, whose logP values are known (determination of the logarithm values of P by means of the retention times by interpolation). linear between two successive alkanones.) The lambda-maximum values were determined by means of the UV spectra with 200 nm to 400 nm at the maximums of the chromatography signals *.

Starting products of the formula (II). Example (II-l) 72 g of hydrochloric acid (33%) are added, at room temperature, with stirring, to a solution of 91 g (0.60 mol) of (S) -l-phenyl-ethylamine in 150 ml of methanol. The mixture is diluted approximately three times higher with toluene and the volatile components are carefully removed by vacuum distillation of the water tube. The residue is melted for 3 hours at 150 ° C to 170 ° C (internal temperature, bath temperature approximately 200 ° C) after the addition of 50.4 g (0.60 mole) of cyanoguanidine. 142 g (98% of theory) of the (S) -1- (1-phenyl-yl) -biguanide * hydrochloride are obtained in the form of a glassy mass, which can be used, without further purification, for the reaction according to the process according to the invention (see example 1). The compound constituted by the hydrochloride of (S) -1- (1-phenyl-propyl) -biguanide can be prepared analogously to that of example (II-1) from (S) -1-phenyl-propylamine Starting materials of the formula (III) Example (III-1) First stage 34.3 g (0.30 mole) of methanesulfonyl chloride are added, over the course of 15 minutes, in portions, under stirring, to an ice-cooled solution of 27.9 g (0.29 mole) of (R) -methyl methyl ester in 100 ml of pyridine. The reaction mixture is stirred for 2 hours at 5 ° C, then poured into 100 ml of water and extracted three times with 100 ml each of methyl-t-butyl ether, (MT'BE). The combined MTBE phases are washed with ice cold 6N hydrochloric acid (2 x 100 ml) with water (2 x 100 ml) and with ice-cold sodium bicarbonate solution (3 x 100 ml), dried over sodium sulfate and filtered . The filtrate is stirred for 30 minutes with activated carbon (Norit A) and filtered again. The solvent is carefully removed by distillation of the filtrate in the vacuum of the water pump. The methyl (R) -a-methylsulfonyloxypropionate is obtained in the form of an amorphous residue, which can be reacted without further purification t according to the description of the second step (see * - below). Second stage. 18.8 g (0.32 moles) of potassium fluoride are added, under stirring, to a mixture heated to 125 ° C formed by 47.9 g (0.26 moles) of methyl (R) -a-methylsulfonyloxy-propionate and 250 g of acetamide. Then, 8 ml of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran are added dropwise to the mixture. The reaction mixture is then stirred for 5 hours at 125 ° C - and for 15 hours at room temperature (approximately 20 ° C.,. it is then heated to 90 C and combined with 250 ml of water under vigorous stirring. After cooling to room temperature, it is extracted three times with 250 ml of dichloromethane each time. The combined organic phases are washed with saturated aqueous solution of common salt (2 x 100 ml) and then with water (1 x 100 ml), dried over sodium sulphate and filtered. The filtrate I is stirred for 30 minutes with activated charcoal and filtered again. The solvent is then removed carefully by distillation from the vacuum filtrate of the water pump. The methyl (S) -α-fluorine propionate is obtained in the form of amorphous residue, which can be used without further purification for the reaction according to the process of the invention - (see example 1). The compound constituted by methyl (R) -α-fluoropropionate can be prepared in a manner analogous to that of example (III-1) from (S) -methyl lactate.

Application examples: Application A. s i Post-outbreak test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 part by weight of alkylaryl polyglycol ether In order to obtain a convenient preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent t, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. With the preparation of the active compound, test plants having a height of 5 to 15 cm are sprayed in such a way that the desired quantities of active compound per unit area are respectively applied. The concentration of the pulverisable broths is chosen in such a way that it is applied in 1,000 liters of water / ha to the desired amount in each case of active product. 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). H.H 100% = total destruction. ^ In this test, for example, the compounds according to the preparation examples 1, 18, 19, 22 and 23 show a potent effect against weeds.

Table A-1: Post-emergence / greenhouse trial Table A-2: Post-emergence / greenhouse test% Table A-3: Post-emergence / greenhouse test.

Example B. 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 horss, the soil is irrigated with the preparation of the active product in such a way that the desired amount of active product per unit area is applied respectively. The concentration of the spray mixture will be chosen in such a way that the quantity of active product desired is applied in 1,000 liters of water per hectare, respectively. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control.

They mean: 0% = no effect (same as untreated controls). 100% = total destruction. In this test it shows, for example, gl composed according to the preparation example 1, with a good compatibility with the crop plants, such as, for example, sunflower, a potent effect against weeds.

Table Bl: Pre-shoot / greenhouse.

Table B2: Pre-outbreak / greenhouse ro Table B3: Pre-shoot / greenhouse, Table B4: Prebote / greenhouse * I Table B5: Pre-shoot / greenhouse I ' It is noted that in relation 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. Having described the invention as above, property is claimed as contained in the following:

Claims (8)

R E I V I N D I C A C I O N S

1. - Aminotriazines substituted with at least two carbon atoms substituted asymmetrically of the general formula (I), characterized in that A means a single bond or means alkanediyl or oxaalkanediyl, respectively straight chain or branched chain, with respectively up to 6 carbon atoms, R 1 means amino, means formylamino or means alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl- N-alkylcarbonyl-amino, alkoxycarbonylamino, N-alkyl-N-alkoxycarbonyl-amino, alkylaminoalkylidenamino or dialkylaminoalkylideneamino with respectively up to 6 carbon atoms in the alkyl groups or in the alkylidene groups, respectively substituted, if appropriate, by cyano, halogen or by alkoxy with 1 to 4 carbon atoms, R 2 signifies hydrogen, halogen or means alkyl with up to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R 3 means hydrogen , halogen or alkyl having up to 6 carbon atoms, optionally substituted by cyano, halogen or alkoxy with 1 to 4 carbon atoms, or together with R2 means alkanediyl having 2 to 5 carbon atoms, optionally substituted by cyano, by halogen or by alkyl having 1 to 4 carbon atoms, R4 means alkyl with up to 6 carbon atoms, or cycloalkyl with 3 to 6 carbon atoms, Y means hydrogen, hydroxyl, mercapto, amino, cyano, halogen, or means alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonylloxy, alkylthio, alkylamino or dialkylamino with respectively up to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and Z means a monocyclic or bicyclic, carbocyclic or heterocyclic group, in any case substituted, of the series consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrate obenzot ienyl, isobenzofuryl, dihydroisobenzoyl furyl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalyl, cinolinyl and phthalazinyl, the possible substituents being chosen, respectively, preferably from the following group: hydroxyl, amino, cyano, nitro, carbamoyl, sulfamoyl, halogen, alkyl, alkoxy, alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by hydroxyl, by cyano or by halogen, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonylamino, alkylaminosul fonyl 'dialkylaminosulfonyl or carbon atoms in the alkyl groups, respectively substituted, if appropriate, by halogen, phenyl or phenoxy substituted, where appropriate, by hydroxy, by cyano, by nitro, by halogen, by alkyl with 1 to 4 carbon atoms, by haloalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by haloalkoxy with 1 to 4 carbon atoms, thus methylenedioxy or ethylenedioxy substituted respectively by halogen, with the proviso that each In particular, R2, R3 and Y have to be different from each other and that the substituents on both carbon atoms, with which R2 and R3 or R4 are linked, have to be configured in the following manner: (a) configuration R in the carbon atom, to which R2 and R3 are linked and R configuration in the carbon atom, with which R4 is bound (* • diastereomers R, RA (b) configuration R at the carbon atom, where R2 and R3 are linked and S configuration at the carbon atom, with which R4 is bound ("R, S diastereomers"), (c) S configuration at the carbon atom, to which R and R are linked and R configuration at the carbon atom, where it is bound ('diastereomers S, R') , (d) S configuration at the carbon atom, with which R2 and R3 are linked and S configuration at the carbon atom, with which R4 is linked ('diastereomers S, S'), (e) R configuration in the carbon atom, with; which are linked R2 and R3 and racemic configuration at the carbon atom, to which R4 (* diastereomers R, rae ") is linked, (f) S configuration at the carbon atom, to which R2 and R3 are linked and racemic configuration at the carbon atom, to which R4 is linked ('diastereomers S, rae').

2. - Compounds of the formula (I) according to claim 1, characterized in that in the same A means a single bond, means methylene (-CH2), dimethylene (ethane-1,2-diyl, -CH2CH2-), ethylidene (ethano- 1, 1-diyl, -CH (CH3) -), oxaet anodiyl (-CH20-), trimethylene (propane-1,3-diyl, -CH2CH2CH2-), propylidene (propane-1, 1-diyl, -CH (C2H5) -, propane-2, 3-diyl (-CH (CH3) CH2-), 2-methyl-propane-1,3-diyl (-CH2CH (CH3) CH2-), 3-oxa-propane-1,3-diyl (-CH2CH20), 2-oxa-propane-1,3-diyl . (-CH2OCH2-), tetramethylene (butane-1,4-diyl, -CH2CH2CH2CH2-), butane-2, 4-diyl (CH (CH3) CH2CH2-), butane-2, 3-diyl (-CH (CH3) CH (CH3) -), 3-methyl-butane-2,4 -diyl (-CH (CH3) CH (CH3) CH2-), 4-oxa-butane-2,4-diyl (-CH (CH3) CH2-0-), pentane-3, 5-di-i lo (-CH (C2H5) CH2CH2-), 5-ox-pentane-3, 5-diol (-CH (C2H5) CH20-), 4-oxa-pentane-2,5-diyl (-CH (CH3) CH2OCH2-) or 5 -oxa-hexane-3,6-diyl (-CH (C2H5) CH2OCH2-), R1 means amino, means formylamino or means methylamino, ethylamino, dimethylamino, acetylamino, propionylamino, n- or i-butyroylamino, N-methyl-N-acetylamino, N-ethyl-N-acetylamino, N -methyl-N-propionyl-amino, methoxycarbonyl amino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methyl-N-methoxycarbonyl-amino, N-ethyl-N-ethoxycarbonyl-amino, N-met i 1 - Neoxycarbonyl-amino, methylaminomethylenamino, ethylaminomethyl, methylaminoethylideneamino or dimethylaminomethyl-ene substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, R2 means hydrogen, fluorine, chlorine, bromine, or. methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R3 means hydrogen, fluorine, chlorine , bromine, or means methyl , ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy or, together with R2, means dimethylene ( ethane-1,2-diyl), trimethylene (propane-1,3-diyl) or tetramethylene (butane-1,4-diyl) substituted, where appropriate, by cyano, fluorine, chlorine, bromine, by methyl or ethyl, R 4 means methyl, ethyl, n- or i-propyl, or means cyclopropyl, Y means hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or -propyl, n-, i- or s-butyl, methoxy, ethoxy, non-propoxy, n-, i- or s-butoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyl loxy, dimethylaminocarbonyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, or s-butylthio, methylamino, ethylamino, n- ' or i-propylamino, n-, i-, or s-butylamino, or dim ethylamino substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and Z means a monocyclic or bicyclic, carbocyclic or heterocyclic group, optionally substituted, of the series formed by cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzoyl, dihydroisobenzoyl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinoline, isoquinoline, quinoxaline, cinolino or phthalazinyl, the possible substituents being chosen, respectively, preferably from following group: hydroxyl, amino, cyano, nitro, carbamoyl, f-sulphamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, etbxi, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino substituted respectively where appropriate by hydroxy, by cyano, by fluorine or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n-; or i-propoxycarbonyl, acetylamino, propionylamino. n- or i-but-iroylamino, -methi-laminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, met iulul finyl, ethylsulphinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, methylsulphonylamino, -ethylsulfonylamino, n- or i-propylsulphonylamino, methylaminosulfonyl, ethylaminosul fonyl, n- or i-propylaminosulfonyl, or dimethylaminosulfonyl substituted, where appropriate, by fluorine and / or by chlorine, phenyl or phenoxy, each optionally substituted by hydroxy, by cyano, by nitro, by fluorine, by chlorine, by methyl, by ethyl, by n- or i- propyl, by n-, i-, s- or t-butyl, i by trifluoromethyl, by methoxy, by ethoxy, by n-> g. or i-propoxy, by n-, i-, s- or t-butoxy, by difluoromethoxy or by trifluoromethoxy, as well as methylenedioxy or ethylenedioxy respectively substituted, if appropriate, by fluorine and / or by chlorine, with the proviso that each particular case R2, R3 and Y are different from each other and from the substituents on the carbon atoms, with which R2 and R3 or R4 are linked are configured in the following manner: (a) R configuration at the carbon atom, with which R2 and R3 are linked and R configuration at the carbon atom, with which R4 is linked ('diastereomers R, R'), (b) R configuration at the carbon atom, where R2 and R are linked; R3 and configuration S at the carbon atom, with which R4 is linked ('diastereomers R, S'), (c) configuration S at the carbon atom, with which R2 and R3 are linked and R configuration at the atom of carbon, in which R4 is linked ('diastereomers S, R'), (d) S configuration in the carbon atom arbono, with which R2 and R3 are linked and configuration S in I. carbon atom, with which it is linked * R ("S, S diastereomers"), (e) R configuration at the carbon atom, with which R2 and R3 are linked and racemic configuration at the carbon atom, with which R4 is linked ('diastereomers R, rae ") ), (f) configuration S at the carbon atom, with which R2 and R3 are linked and racemic configuration at the carbon atom, to which R4 is linked ('diastereomers S, rae').

3. Compounds of the formula (I) according to claim 1, characterized in that in the same A means a single bond, means dimethylene (ethane-1,2-diyl, -CH2CH2-) oxaetanediyl (-CH? O-) or 2-oxa-propane-l, 3-diyl (-CH20CH2-), R1 means amino, means formylamino or means acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonilamino or dimethylaminomethyl-amino substituted respectively where appropriate by cyano, by fluorine, by chlorine, by "methoxy" or by "ethoxy", R 2 means hydrogen, fluorine, chlorine or means methyl, ethyl, n-i-propyl, respectively substituted, if appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, R 3 is hydrogen, fluorine , chlorine, bromine, or means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or together with R2, means dimethylene (ethane-1, 2-diyl) substituted, where appropriate, by cyano, by fluorine, per gold or methyl,; R4 means methyl or ethyl, Y means hydrogen, hydroxyl, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, methoxycarbonyloxy, ethoxycarbonyloxy , methylaminocarbonyloxy, ethylaminocarbonyloxy or dimethylaminocarbonyloxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, and Z means an oncyclic or bicyclic, carbocyclic or heterocyclic group, optionally substituted, of the series formed by phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, and sobenzofuryl, dihydroisobenzofuryl, isobenzo thienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl. , oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, qui nolyl, isoquinolyl, quinoxalinyl, cinolino and phthalazinyl, the possible substituents being chosen, respectively, preferably from the following group: hydroxyl, amino, cyano, -nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, dimethylamino, substituted respectively by hydroxy, by cyano, by fluorine or by chlorine, acetyl, methoxycarbonyl, ethoxycarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, etyl sulphonyl, methylsulfonyl, ethylsulphonyl, or dimethylaminosulfonyl respectively substituted, respectively, by fluorine and / or by chlorine, phenyl or phenoxy substituted respectively in case given by hydroxy, by cyano, by nitro, by fluorine, by chlorine, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by trifluoromethyl, by methoxy , by ethoxy, by n- or i-propoxy, by difluoromethoxy or by trifluoromethoxy, as well as methylendium xi or ethylenedioxy substituted respectively by fluorine and / or by chlorine, with the proviso that in each particular case R2, R3 and Y are different from each other and that the substituents on the carbon atoms, with which they are linked R2 and R3 or R4, have the following configuration: (a) R configuration at the carbon atom, to which R2 and R3 are linked and R configuration at the carbon atom, with which R4 is linked ("R, R diastereomers"), (b) R configuration at the carbon atom, where R2 and R3 are linked and S configuration at the carbon atom, to which R4 is linked ('R, S diastereomers'), (c) S configuration at the carbon atom, with which R2 and R3 are linked and R configuration at the carbon atom, in which it is bound • R ("S, R diastereomers"), (d) S configuration at the carbon atom, with which R2 and R3 are linked and S configuration at the carbon atom, with which R4 is linked ("S, S diastereomers"),

4. Process for obtaining the compounds of the formula (I) according to claim 1, characterized in that substituted biguanides of the general formula (II) are reacted wherein A, R1, R4 and Z have the meaning indicated in claim 1, and / or adducts with acids of the compounds of the general formula (II) - with (optically active) derivatives of carboxylic acids of the general formula (III) wherein R2, R3 and Y have the meaning indicated above and X means halogen or alkoxy, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent and optionally performed on the products of the general formula (I), obtained in this way, other transformations according to usual methods within the scope of the above definition of the substituents.

5. Herbicidal agents, characterized in that they have a content in at least one compound of the formula (I) according to claim 1.

6. Use of the compounds of the formula (I) according to claim 1, for the control against undesirable growth of plants.

7. Procedure for the fight against weeds, characterized in that compounds of the formula (I) according to claim 1 are allowed to act on the weeds or on their environment.

8. - Process for the preparation of herbicidal agents, characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and / or with surfactants. SUMMARY OF THE INVENTION The invention relates to substituted optically active aminotriazines having at least two asymmetrically substituted carbon atoms of the formula (I) wherein A means a single bond or signified alkanediyl or oxaalkanediyl, respectively straight chain or branched chain; R1 means amino, formylamino or alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonyl-amino, alkoxycarbonylamino, N-alkyl-N-alkoxycarboni 1-amino, alkylaminoalkylideneamino or dialkylaminoalkylideneamino which are respectively substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms; R2, R3 are hydrogen, halogen or alkyl, which is optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms or R3 together with R2 means alkanediyl which is optionally substituted by cyano, by halogen, alkyl with 1 to 4 carbon atoms; R4 means alkyl or cycloalkyl; Y means hydrogen, hydroxy, mercapto, amino, cyano, halogen, or alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkyl laminocarbonyl oxy, alkylthio, alkylamino or dialkylamino which are optionally substituted by cyano, by halogen or by alkoxy with to 4 carbon atoms and Z means a monocyclic or bicyclic, carbocyclic or heterocyclic radical, which may be substituted if appropriate. Substituents are such that R2, R3 and Y are different from each other in each individual case, and that the substituents on both carbon atoms, with which R2 and R3 or R4 are linked, have the R, R or R configuration , S or S, R or S, S or R, Rac or S, Rac [meaning the first indication to the triazine substituents, CR2R3Y, and the second indication referring to amino substituents -CHR4- (AZ)]. The invention also relates to a process for the preparation of the compounds of the formula (I) and their use as herbicides.