MXPA99008144A - Heterocyclically substituted aromatic amino compounds with a herbicidal effect - Google Patents

Abstract

New substituted aromatic amino compounds are disclosed having the general formula (I), in which R1, R2, R3, R4 and Z have the meanings given in the description, as well as a process for preparing the same and their use as herbicides.

Description

AROMATIC AMINOCOMPOSITES SUBSTITUTED IN A HETEROCYCLIC WAY WITH HERBICIDE EFFECT. Field of the invention. The invention relates to novel substituted aromatic amino compounds, to processes for their preparation and to their use as herbicides. Description of the prior art. Some substituted aromatic amino compounds, such as for example N- [2- (1, 5-dihydro-1-methyl-5-thioxo-3-trifluoromethyl-4H-1, 2) are already known from the patent literature as potential herbicides. , 4-triazol-4-yl) -5-fluoro-phenyl] -benzamide and N- [5-chloro-2- (1, 5-dihydro-l-methyl-5-thioxo-3-trifluoromethyl-4H- 1,2,4-triazol-4-yl) -phenyl] -acetamide (see US 5108486). However, these compounds have not acquired any special significance. Other substituted aromatic amino compounds, such as for example N- [5-chloro-2- (2,5-dihydro-3,4-dimethyl-2,5-dioxo-lH-pyrrole-1), have also already been disclosed. -yl) -phenyl] -acetamide (see Indian J. Chem. Sect. B, 29B (1990), 659-660 - cited in Chem. Abstracts 113: 211906), as well as N- [2- (5-diethylamino -3-t-butyl-lH-l, 2,4-triazol-l-yl) -5-trifluoromethyl-phenyl] -2,2-dimethyl-propanoamide and N- [2- (5-diethylamino-3- t-butyl-lH-l, 2,4-triazol-l-yl) -5-trifluoromethyl-phenyl] -acetamide (see JP 02091062 - cited in Chem. Abstracts REF .: 31018 113: 7612). However, nothing has been disclosed about a herbicidal activity of these compounds. Detailed description of the invention. New substituted aromatic amino compounds of the general formula (I) have now been found, wherein R 1 signifies hydrogen, hydroxy, amino, alkyl, alkoxy, alkylamino or dialkylamino or means one of the following groupings, -CQ ^ -R5, -CQ ^ -Q ^ -R6, -S (0) n-R7, R2 means one of the following groupings, -CQ ^ -R5, -CQ1- © .2 -! * 6, -S (0) n-R7, R3 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl respectively substituted, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2 / -N (S02-R7) (CO-R5), R4 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarba oyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl respectively substituted, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), n means 0, 1 or 2, Q1 means O or S, and Q2 means O, S, NH or N-alkyl, R5 means hydrogen or means alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl substituted respectively where appropriate R6 means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl substituted respectively where appropriate, R7 means alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl respectively substituted if appropriate, and Z means one of the groupings following heterocyclics: (Z1) (Z-) (Z5) (Z4) ((Z6) (Z ') (Z8) (Z9) Q1 (z10) (z11) (z, 2 > (Z; (Z23) (Z24) (Z28) (z29) (z30) ) (z34) (z35) (Z3S) wherein, respectively, Q1 and Q2 have the meaning indicated above, R8 signifies hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or means alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkenylthio, alkylamino, dialkylamino, cycloalkyl or cycloalkylalkyl substituted respectively where appropriate, and R9 signifies hydrogen, hydroxy, amino, cyano, or means alkyl, alkenyl, alkynyl, alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl respectively substituted, if any, meaning if appropriate, two contiguous residues -R8 and R8, R9 and R9 or R8 and R9- together with alkanediyl (alkylene) or oxalkanediyl, and the individual residues R8 and R9 may have -in so far as they are contained more than once in the same heterocyclic grouping, the same meanings or meanings within the scope of the above definition, with the exception of the previously known compound N- [5-chloro-2- (2,5-dihydro-3,4-dimethyl-2, 5-dioxo-lH-pyrrol-1-yl) -phenyl] -acetamide (see Indian J. Chem. Sect. B, 29B (1990), 659-660 - cited in Chem. Abstracts 113: 211906), as well as N- [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazole-1- il) -5-trifluoromethyl-phenyl] -2, 2-dimethyl-propanoamide and N- [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) - 5-trifluoromethyl-phenyl] -acetamide (see JP 02091062-cited in Chem. Abstracts 113: 97612) The novel substituted aromatic amino compounds of the general formula (I) are obtained, if aromatic amino compounds of the general formula (II) are reacted ) wherein R3, R4 and Z have the meaning indicated above and A1 means hydrogen, hydroxy, amino, alkyl, alkoxy, alkylamino, or dialkylamino, with electrophilic compounds of the general formula (III), XB in which R2 has the meaning indicated above and X means halogen, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, and the compounds obtained in this way of the general formula (I ), they are processed, if appropriate, according to usual methods, into other compounds of the general formula (I) according to the above-mentioned definition (see the preparation examples). The new substituted aromatic amino compounds of the general formula are characterized by a potent and selective herbicidal activity. In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl -even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino- are respectively straight-chain or branched chain. In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially fluorine or chlorine. The subject of the invention are preferably compounds of the formula (I), in which R 1 is hydrogen, hydroxy, amino, means alkyl, alkoxy, alkylamino or dialkylamino with 1 to 6 carbon atoms in the alkyl groups, or represents one of the following groupings, CQ ^ -R5, -CO ^ -Q ^ -R6, -S (0) n-R7, R2 means one of the following groupings, -CO ^ -R5, -CO ^ -O ^ -R6, -S (0) n-R7, R3 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 6 carbon atoms in the alkyl groups, respectively substituted in case given by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), R means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl with 1 to 6 carbon atoms in the alkyl groups, respectively substituted in case given by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), n means 0, 1 or 2, Q1 means 0 or S and Q2 means O, S, NH or N-alkyl having 1 to 4 carbon atoms, R5 means hydrogen, means alkyl having 1 to 6 carbon atoms substituted on case given by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means cycloalkyl or cycloalkylalkyl with respectively 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4 carbon atoms in the alkyl part, substituted respectively, optionally by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, means aryl or arylalkyl with 6 to 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the substituted alkyl part where appropriate, cyano, nitro, halogen, alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, or heterocyclic ilo substituted, if appropriate, 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 halogenalkoxy with 1 to 4 carbon atoms, Preferred as heterocyclyl groups are furyl, tetrahydrofuryl, thienyl, pyridyl and pyrimidinyl, R6 means alkyl having from 1 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atomsmeans alkenyl or alkynyl with respectively 2 to 6 carbon atoms substituted, where appropriate, by halogen, means cycloalkyl or cycloalkylalkyl with respectively 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the part alkyl substituted respectively by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, or means aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and, optionally, 1 to 4 carbon atoms in the alkyl part, respectively substituted, where appropriate by cyano, by nitro, by halogen, by alkyl having 1 to 4 carbon atoms, R means alkyl having from 1 to 6 carbon atoms, optionally substituted by halogen, means cycloalkyl or cycloalkylalkyl respectively 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, respectively substituted, if appropriate, by halogen no, it means aril Or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, optionally substituted by cyano, by nitro, by halogen, by alkyl with 1 to 4 carbon atoms , by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms, or means heterocyclyl optionally substituted by halogen, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms or for halogenalkoxy with 1 to 4 carbon atoms, with heterocyclyl pyridyl and pyrimidinyl groups being preferred, and Z being one of the following heterocyclic groupings, (Z5) (Z ") (Z5) (z10) (z11) (Z ") R ° R 'N N "R B N N N N N - N R ° Rß (Z22) (Z23) (Z24) Q1 R8 ^ Q t r N N A N -R = N-N i N N- ^ / Q (Z25) (Z26) (z27) (z28) (Z (Z30) ) (Z34) (z35y (Z35) where respectively Q1 and Q2 have the meaning indicated above, R8 means hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, means alkyl having 1 to 6 carbon atoms substituted if necessary by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl or alkynyl with respectively 2 to 6 carbon atoms substituted respectively by halogen, means alkoxy or alkoxycarbonyl having 1 to 6 carbon atoms in each case alkyl groups substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyloxy or alkynyloxy having respectively 3 to 6 carbon atoms substituted, if appropriate by halogen, means alkylthio with 1 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenylthio or alkynylthio with respectively 3 to 6 carbon atoms substituted, if appropriate, by halogen, means alkylamino or dialkylamino having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl or cycloalkylalkyl with respectively 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, respectively substituted, if appropriate, by cyano, halogen or alkyl with 1 to 4 carbon atoms, and means hydrogen, hydroxy, amino, cyano, means alkyl having 1 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl or alkynyl with respectively 2 to 6 carbon atoms substituted, if appropriate, by halogen, means alkoxycarbonyl optionally substituted by cyano, by halo or by alkoxy with 1 to 4 carbon atoms, means cycloalkyl or cycloalkylalkyl with 3 to 6 carbon atoms respectively in the cycloalkyl groups and, optionally, 1 to 4 carbon atoms in the alkyl part, optionally substituted by cyano, by halogen or by alkyl having 1 to 4 carbon atoms or means phenyl or phenyl-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by cyano, by nitro, by halogen, by alkyl having 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms and / or by haloalkoxy with 1 to 4 carbon atoms, meaning if appropriate two contiguous residues -R8 and R8, R9 and R9 or R8 and R9- collectively alkanediyl (alkylene) or oxaalkanediyl with respectively 2 to 6 carbon atoms, and the individual residues R8 and R9 may have - as long as they are contained more than once in the same heterocyclic group, the same meaning or different meanings within the scope of the above definition, with the exception of the previously known compound N- [5-chloro-2- (2,5-dihydro-3,4-dimethyl-2,5-dioxo) -lH-pyrrol-1-yl) -phenyl] -acetamide (see Indian J. Chem. Sect. B, 29B (1990), 659-660 - cited in Chem. Abstracts 113: 211906), as well as N- [ 2- (5-diethylamino-3-t-butyl-lH-l, 2,4-triazol-1-yl) -5-trifluoromethyl-phenyl] -2,2-dimethyl-propanoamide and the N- [2- ( 5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) -5-trifluoromethyl-phenyl] -acetamide (see JP 02091062 - cited in Chem. Abstracts 113: 97612). The subject of the invention are especially the compounds of the formula (I), in which R 1 is hydrogen, hydroxy, 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, methylamine, ethylamino, n- or i-propylamino, n-, i-, s- or t- butyl- a ino or dimethylamino, or means one of the following groupings, -CQ1-R5, -CQ1-Q2-R6, -S (0) n -R7 R2 means one of the following groupings, -CQ ^ -R5, -CQ ^ -Q ^ -R6, -S (0) n-R7, R3 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, 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, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio , methylsulfinyl, ethylsulfinyl, ethylsulphonyl, or ethylsulphonyl, respectively substituted by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5) R 4 is hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, 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, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t butylthio, methyl sulfinyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), n means 0, 1, or 2, Q1 means O or S and Q2 means O, S, NH or N-methyl, R5 means hydrogen, means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl optionally substituted by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted respectively in case given by cyano, by fluorine, by chlorine, by bromine, by methyl or by ethyl, means phenyl or benzyl substituted respectively by cyano, by nitro, by fluorine, by chlorine, by bromine, 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 n-, i-, s- or t -butoxy, by difluoromethoxy or by trifluoromethoxy, or means furyl, tetrahydrofuryl, thienyl or pyridyl optionally substituted by fluorine, by chlorine, by bromine, 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 n-, i-, s- or t- butoxy, by difluoromethoxy or by trifluoromethoxy, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propynyl or butynyl substituted, where appropriate, by fluorine, chlorine or bromine, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl respectively substituted by cyano, by fluorine, by chlorine, by bromine, by methyl or by ethyl, or by phenyl or benzyl respectively substituted by cyano, by nitro, by fluorine, by chlorine, by bromine, 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 n-, i-, s- or t- butoxi, by di fl uoromethoxy or trifluoromethoxy, R7 is methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl optionally substituted by fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl respectively substituted, where appropriate, by fluorine, chlorine or bromine, means phenyl or benzyl substituted, where appropriate, by cyano, by nitro, by fluorine, by chlorine, by bromine, 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 n-, i- , s- or t-butoxy, by difluoromethoxy, by trifluoromethoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, i-, s- or t-butylthio, by methylsulfinyl, by ethylsulfinyl, by methylsulfonyl, by ethylsulphonyl, by methoxycarbonyl or by ethoxycarbonyl, or by pyridyl or pyrimidinyl, optionally substituted by fluorine, by chlorine, by bromine, 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 n -, i-, s- or t-butoxy, by difluoromethoxy, or by trifluoromethoxy, and Z means one of the following heterocyclic groupings, (z4) (Z5) (Z6) (z7) (z8) (Z9) Q1 (Z10) (z11) (z12) Rß R "1 Q2 N ^ N 'R 8 N N ^ i, N N-N (z22) (z23) (z24) 17 (Z (Z, (2) (Z28) (Z29) (Z30) (z34) (z35) (z3E) where respectively Q1 and Q2 have the meaning indicated above, R8 means hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, if appropriate by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propynyl or butynyl respectively substituted, if appropriate by fluorine, by chlorine or by bromine, means methoxy, ethoxy, n- or -propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl or ethoxycarbonyl respectively substituted, optionally by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyloxy, butenyl-oxy, propynyloxy or butynyloxy substituted, where appropriate, by fluorine or by chlorine, means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, optionally substituted by cyano, by fluorine, by chlorine , by methoxy or by ethoxy, means propenylthio, butenylthio, propynylthio or butynylthio substituted respectively by fluorine or chlorine, respectively methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means cyclopropyl cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl respectively substituted, where appropriate, by cyano, fluorine, chlorine, bromine, methyl or ethyl, and means hydrogen, hydroxy, amino, cyano, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, if appropriate, by cyano, by fluorine, by cyclo, by methoxy or by ethoxy, means propenyl, buteni-lo , propynyl or butynyl substituted, where appropriate, by fluorine, chlorine or bromine, means methoxycarbonyl or ethoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclopropylmethyl. , cyclobutylmethyl , cyclo-pentylmethyl or cyclohexylmethyl substituted, where appropriate, by cyano, fluorine, chlorine, bromine, methyl or ethyl, or phenyl or benzyl respectively substituted, if appropriate, by cyano, by nitro, by fluorine, by chlorine , by bromine, 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 n-, i-, s- or t-butoxy, by difluoro methoxy and / or by trifluoromethoxy, signifying if necessary two contiguous residues -R8 and R8, R9 and R9 or R8 and R9 - together ethane-l, 2-diyl (dimethylethylene), propane-l, 3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or 1-oxabutane-1,4-diyl, and the individual residues R8 and R9 may have as long as they are contained more than once in the same heterocyclic grouping, the same meanings or meanings differ within the scope of the above definition, with the exception of the previously known compound N- [5-cl gold-2- (2,5-dihydro-3,4-dimethyl-2, 5-dioxo-lH-pyrrol-1-yl) -phenyl] -acetamide (see Indian J. Chem. Sect. B, 29B (1990 ), 659-660 - cited in Chem. Abstracts 113: 211906), as well as N- [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) -5 -trifluoromethyl-phenyl] -2,2-dimethyl-propanoamide and N- [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) -5-trifluoromethyl- phenyl] -acetamide (see JP 02091062-cited in Chem. Abstracts 113: 97612). Very particularly preferred are those compounds of the formula (I), in which R1, R2, R3, R4, n, Q1, Q2, R5, R6 and R7, have the meanings indicated above as being particularly preferred, and Z means one of the following heterocyclic groupings, (Z1) (Z3) < Z ") (Z, 3 > (z27) (z33)where, respectively Q1, Q2, R8 and R9 have the meanings indicated above as being especially preferred. The definitions of the residues indicated above in a general manner or indicated in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the intermediate products necessary 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. Examples of compounds according to the invention of the formula (I) have been indicated in the following groups.

Group 1.

R1, R2, R3 and R4 have, in this case, the meanings indicated in the following enumeration: Group 2 R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 3.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 4.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 5.

R, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 6.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 7.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 8.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 9.

R1, R2, R3 and R4 have in this case, for example, the meanings indicated in group 1.

Group 10 R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 11.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 12.

R1, R2, R3 and R4 have in this case, for example, the meanings indicated in group 1.

Group 13 R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 14.

R1, R2, R3 and R4 have, for example, the meanings indicated in group 1. Group 15.

R, R2, R3 and R4 have, for example, the meanings indicated in group 1. If, for example, 2- (2-amino-4-cyano-phenyl) -4-methyl-5-difluoromethyl is used, for example. -2,4-dihydro-3H-l, 2,4-triazol-3-one and the acetyl chloride as starting materials, the development of the reaction in the case of the process according to the invention can be schematized by means of the scheme of following formulas: The aromatic amino compounds, 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 formula (II), R3, R4 and Z preferably have or especially those meanings which have already been mentioned above in a preferential manner or, more preferably, for R3, R4 and Z in relation to the description of the compounds of the invention. formula (I) according to the invention; preferably A1 means hydrogen, hydroxy, amino, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or di- (alkyl with 1 to 6 carbon atoms) -amino , especially means hydrogen or methyl. The starting materials of the general formula (II) are not yet known from the literature; they constitute, as new products, also an object of the present application. The new aromatic amino compounds of the general formula (II) are obtained if aromatic nitrocompounds of the general formula (IV) are reacted R3, R4 and Z have the meaning indicated above, with reducing agents, such as for example with hydrogen in the presence of a catalyst, such as for example Raney nickel, or with tin (II) chloride dihydrate, or with iron in the presence of of an acid, such as for example hydrochloric acid, respectively in the presence of a diluent, such as for example water, methanol or ethanol, at temperatures between 0 ° C and 120 ° C (see the preparation examples). The aromatic nitro compounds necessary as starting materials of the general formula (IV) are known and / or can be prepared according to known processes (see US 3489761, DE 2413938, GB 2123420, US 4496390, WO 8702357, EP 617026, examples of preparation ). The electrophilic compounds to be further 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 (III). In the formula (III), R.sup.2 preferably has, in particular, those meanings which have already been mentioned above in a preferred manner or, more preferably, for R.sub.2 in relation to the description of the compounds of the formula (I) according to the invention; preferably X means fluorine, chlorine, bromine or iodine, especially chlorine or bromine. The starting materials of the general formula (III) are organic chemicals for known syntheses. The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out using an acid acceptor. Suitable acid acceptors for the process according to the invention are generally the customary inorganic or organic bases or the acid-binding agents. 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, potassium amide. or of calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate, ethanolate, n- or i-propane-lato, n-, i-, s- or sodium or potassium t-butanolate; furthermore, basic organic nitrogenous compounds, such as, for example, trimethylamine, triethylamine, tripro-phenylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl-amine, 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-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2, 2, 2] octane (DABCO), 1 , 5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] -undec-7-ene (DBU). The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention are all inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic hydrocarbons, if appropriate halogenated, such as, for example, benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloride tetro carbon; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol di ethyl or diethylether; 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-form-nilide, N-methyl-pyrrolidone or hexamethylphosphorotriamide; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The 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 120 ° C. The process according to the invention will generally be 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. In order to carry out the process according to the invention, the starting materials are generally used.in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction will be carried out in general in a suitable diluent in the presence of a reaction auxiliary agent and the reaction mixture will generally be stirred for several hours at the necessary temperature. The processing will be carried out according to usual methods (see the preparation examples). The active compounds according to the invention can be used as defoliants, desiccants, agents for removing harmful plants, especially for destroying weeds. 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: Dicotyledonous weeds of the following types: Sinapis, Lepi-dium, 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, Emex, Datura, Viola, Geleopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum . Dicotyledonous crops of the classes: Gossypiu, Gly-cine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusi-ne, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus , Paspalum, Ischaemum, Sphenoclea, Dac-tuloctenium, Agrotis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is, however, not limited in any way to these classes, but extends in the same way also to 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. Likewise, the compounds can be used to control weeds in permanent crops, for example, in forest installations, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, Te from the rubber tree, from oil palms, from cocoa, from berries and hops, on ornamental and sporting paths and on surfaces for meadows and to selectively control weeds in mono-annual crops. The compounds of the formula (I) according to the invention are suitable for the control of monocotyledonous and dicotyledonous weeds in monocotyledonous crops, such as, for example, wheat, both in the pre-emergence procedure and in the post-emergence process. -outbreak. 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 product, as well as micro-encapsulated 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 diluents, where appropriate, using surfactants, that is, emulsifiers and / or dispersants. santes and / or means generating foam.

In the case of using water as a loading material, it can be used, for example, also organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, hydrocarbons. aliphatics, such as cyclohexane or paraffins, for example, fractions of crude petroleum, 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 di-methylsulfoxide as well as water. Suitable solid excipients are, for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, atta-pulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates, as solid excipients for granulates 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, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulphates, aryl sulfonates, and albumin hydrolysis products; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellul Adhesives such as carboxymethylcellul natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cefaliña 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, ti-tanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight. The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides for the control of weeds, with possible finished formulations or tank mixtures. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Allo-xydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron ( -methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Biala-phos, Bifenox, Bromobutide, Bromophenoxy, Bromoxynil, Buta-chlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2 , 4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC , Esprocarb, Ethalfluralin, Etham etsulfuron (-methyl), Ethofu esate, Ethoxyfen, Etobenzanid, Fenoxaprop-ethyl, Framprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumi-chlorac (-pentol), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupro-pacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurta one, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen , Haloxyfop (-ethoxyethyl) - Hexa-zinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, loxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapy-rifop, Lactofen, Lenacil, Linuron, MCPA , MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Etobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metsulfu-ron (-methyl), Metribuzin, olinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orben-carb , Oryzalin, Oxadiazon, Oxyfluorfen, Paraq uat, Pnedime-thalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfu-rum (-methyl), Prometryn, Propachlor, Propanil, Propaquiza-fop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop - (- ethyl), Quizalofop (-p-tefuril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometu-ron (-methyl), Sulfosate, Tebutam, Tebuthiuron , Terbuthylazi-ne, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarba-zil, Tral oxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfu-ron. It is also possible to mix with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, products that protect against ingestion by birds, nutrient products for plants and agents that improve the structure of the soil. The active products can be used as such, in the form of their formulations or in the forms of application prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. The application is carried out in a conventional manner, for example by watering, atomising, 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 in the field before planting. The amount of active ingredient used can vary within wide limits. This depends, fundamentally, on the type of the desired effect. In general, the amounts applied are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per ha. The preparation and use of the active compounds according to the invention are illustrated by means of the following examples. Examples of obtaining: Example l: A mixture of 1.6 g (5.23 mmol) of l- (2-amino-5-chloro-phenyl) -3,6- is stirred for 45 minutes at room temperature (approximately 20 ° C). dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine, 0.72 g (5.23 mmol) of pivaloyl chloride, 1.21 g (12 mmol) of triethylamine and 30 ml of acetonitrile and it is then concentrated by evaporation under vacuum of the water pump. The residue is then stirred with IN hydrochloric acid, diethyl ether and petroleum ether and the crystalline product formed in this case is isolated by suction filtration. 1.65 g (81% of theory) of 1- (5-chloro-pivaloylamino-phenyl) -3,6-dihydro-2,6-dioxo-4-tri-fluoromethyl-1 (2H) are obtained pyrimidine with a melting point of 276 ° C. Example 2 A mixture consisting of 1.17 g (3 mmol) of 1- (5-chloro-2-pivaloylamino-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromide is heated at reflux for 45 minutes. tl-l (2H) -pyrimidine, 0.42 g (3 mmol) of dimethyl sulfate, 0.46 g (3 mmol) of potassium carbonate and 20 ml of acetone and then concentrated by vacuum evaporation of the tube of water. The residue is then stirred with IN hydrochloric acid, with ethyl acetate and with diethyl ether, the crystalline product formed in this case being isolated by suction filtration. 1.05 g (88% of theory) of 1- (5-chloro-2-pivaloylamino-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 are obtained (2H) -pyrimidine with a melting point of 267 ° C. In a manner analogous to that of the preparation examples 1 and 2 and according to the general description of the preparation process according to the invention, compounds of the formula (I) indicated in the following tables can also be prepared, for example.

A large part of the active compounds according to the invention can be represented by means of the general formula (la) below: (the) Table la: Examples of compounds of the formula (la) Another part of the active compounds according to the invention can be represented by the following general formula (Ib): Table Ib: Examples of the compounds of the formula (Ib) Table: Other examples of compounds of the formula (la) - eleven - Starting products of the formula (II): Example (II-1).

The mixture is stirred for 45 minutes at 80 ° C, a mixture consisting of 15.0 g (44.7 mmol) of l- (5-chloro-2-nitro-phenyl) -3,6-dihydro-2,6-dioxo. -4-trifluoromethyl-1 (2H) -pyrimidine, 30.25 g of tin (II) chloride dihydrate, 20 ml of water and 100 ml of 33% hydrochloric acid, and then concentrated by evaporation under vacuum of the water pump. The residue is then taken up in water and poured into a 5% aqueous solution of sodium dihydrogen phosphate and ethyl acetate. The organic phase is separated, washed with 5% aqueous sodium dihydrogen phosphate solution, dried over sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with diethyl ether / petroleum ether and the crystalline product formed is isolated by suction filtration. 11.6 g (85% of theory) of 1- (2-amino-5-chloro-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) are obtained. ) -pyrimidine with a melting point of 293 ° C. Example (II-2).

A mixture of 2.3 g (7 mmol) of 1- (2-nitro-4-trifluoromethyl-phenyl) -5-cyclopropyl-2-methyl-3,5-dioxo-2 was heated to reflux. , 4-triazole, 2.4 g (42 mmol) of iron and 100 ml of 50% aqueous ethanol and a solution of 0.2 ml of concentrated hydrochloric acid in 10 ml is added dropwise to the mixture. of 50% aqueous ethanol. The reaction mixture is refluxed for 70 minutes and then filtered off with suction through silica gel. The solvent is removed from the filtrate carefully by vacuum distillation of the water tube. 2.4 g (98% of theory) of l- (2-amino-4-trifluoromethyl-phenyl) -5-cyclopropyl-2-methyl-3,5-dio-x-1, 2,4- are obtained. triazole in the form of a crystalline residue with a melting point of 154 ° C. Example (II-3). 12 g (41 mmol) of 4-methyl-2- (2-nitro-phenyl) -5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 10 ml of methanol and hydrogenated, in the presence of 3 g of Raney nickel for 4 hours at 50 ° C and 50 bar of hydrogen pressure. The cooled reaction filtrate is filtered and the filtrate is concentrated by evaporation under vacuum of the water pump. The residue is then azeotropically dried with toluene. After a further concentration by evaporation, the residue is digested with petroleum ether and the crystalline product formed is isolated by suction filtration. 10 g (94% of theory) of 2- (2-amino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1, 2,4-triazol-3-one are obtained with a melting point of 101 ° C.

In a manner analogous to that of the preparation examples (II-1) to (II-3), for example, compounds of the formula (II) indicated in the following tables (2a and 2b) can also be prepared.

A large part of the starting products according to the invention can be represented by the following general formula (lia).

Table 2a: Examples of the compounds of the formula (lia).

Another part of the starting products according to the invention can be represented by means of the following general formula (Hb): Table 2b; Examples of the compounds of the formula (Ilb) Starting products of the formula (IV) Example (V-i) 1 ^ Stage. 118.9 g (109.5 mmol) of 5-chloro-2-nitroaniline are dissolved in 150 ml of acetone and added dropwise to this solution at room temperature (about 20 ° C) under stirring, 27 g (128 mmoles) of trichloromethyl chloroformate ("diphosgene"). The reaction mixture is stirred for 30 minutes then combined, dropwise, with 150 ml of ethanol. After a further 30 minutes, the mixture is evaporated under vacuum from the water pump, the residue is digested with water / petroleum ether and the crystalline product formed is isolated by suction filtration. 22.4 g (84% of theory) of N- (5-chloro-2-nitro-phenyl) -O-ethyl-urethane are obtained with a melting point of 86 ° C. 2nd Stage. 25 g (0.10 mol) of ethyl 3-amino-4,4,4-trifluoro-crotonate in 100 ml of N, N-dimethylformamide are placed. After addition of 3.5 g (0.15 mol) of sodium hydride, the mixture is stirred for 30 minutes at room temperature (about 20 ° C) and then combined with 24.5 g (0.10 moles) of N. - (5-chloro-2-nitro-phenyl) -O-ethyl-urethane (see 1st stage). The reaction mixture is then heated for 150 minutes at 130 ° C and then poured into an approximately two-fold volume of ice water. It is shaken twice with ethyl acetate, then the aqueous phase is acidified with 2N hydrochloric acid and shaken again with ethyl acetate. The organic phase is washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with 5 ml of ethyl acetate, 50 ml of diethyl ether and 50 ml of petroleum ether and the crystalline product formed is isolated by suction filtration. 21 g (62.5% of theory) of 1- (5-chloro-2-nitro-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) are obtained. ) -pyrimidine with a melting point of 214 ° C. Example (IV-2) 8.4 g (0.05 mole) of 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1, 2,4-triazol-3-one are dissolved in 50 ml of dimethylsulfoxide and combined with 6. , 9 g (0.05 mole) of potassium carbonate (powder) and 7.0 g (0.05 mole) of 2-fluoro-nitrobenzene. The reaction mixture is then heated under stirring for 16 hours at 80 ° C and, after cooling, it is poured into 200 ml of water. It is extracted twice with methylene chloride, the combined organic phases are washed with water, dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with diethyl ether and the crystalline product formed is isolated by suction filtration. 12.7 g (88% of theory) of 4-methyl-2- (2-nitro-phenyl) -5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazole-3- is obtained. ona with a melting point of 83 ° C. Analogously to the preparation examples (IV-1) and (IV-2), it is also possible, for example, to prepare the compounds of the formula (IV) indicated in the following tables (3a and 3b).

A large part of the starting products according to the invention can be represented by the following general formula (IVa): Table 3a; Examples of compounds of the formula (IVa) Another part of the starting materials according to the invention can be represented by the following general formula (IVb): Table 3b; Examples of compounds of the formula (IVb) Application examples; Example A. Pre-bud 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 of the test plants are sown in normal soil. Approximately after 24 hours, the soil is irrigated with the preparation of active product, in such a way that the quantity of active product desired per unit area is applied respectively. The concentration of the sprayable broths will be chosen in such a way that the quantities of active compound desired in each case are applied in 1000 1 of water / ha. After three weeks, the degree of damage of the plants compared with the development of the untreated control is evaluated in%. They mean: 0% = no effect (same as untreated controls) 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 18, 19, 20, 23, 24 and 102, with an application amount comprised between 250 and 750 g / ha, with a good compatibility with the plants of cultivation, such as for example wheat (0%), a potent effect against weeds, such as Avena fatua (100%), Cyperus (70-100%), Setaria (90-100%), Abutilón (70-100) %), Amaranthus (90-100%), Galium (90-100%), Sinapis (95-100%), Lolium (100%), Ipomoea (95-100%), Matricaria (100%) and Solanum (100%) %). 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 the 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. With the preparation of active product, test plants are sprayed, having a height of 5 -15 cm, so that in each case, the desired amounts of active product per unit area are applied. The concentration of the sprayable broths is selected in such a way that the desired quantities of active product are applied in each case in 1000 1 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 untreated controls) 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 18, 19, 20, 23, 24 and 102, with an application amount comprised of 15-750 g / ha, with a good compatibility with the crop plants, such as for example wheat (5-10%), a potent effect against weeds, such such as Avena fatua (85-95%), Cyperus (90-95%), Setaria (95-100%), Abutilon (100%), Amaranthus (95-100%), Galium (100%), Sinapis (100%) ), Chenopodium (95-100%), Matricaria (95-100%), polygonum (95-100%) and Viola (90-100%). 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.

Claims (9)

CLAIMS Having described the invention as above, the property claimed in the following claims is claimed as:

1. Aromatic amino compounds of the general formula (I), characterized in that R 1 signifies hydrogen, hydroxy, amino, alkyl, alkoxy, alkylamino or dialkylamino or means one of the following groupings, -COYR5, -CQ1-Q2-R6, -S (0) n-R7, R means one of the following groupings, -COYR5, -COYOYR6, -S (0) n-R7, R3 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl respectively substituted, or means one of the following groupings, -S02 -NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), R4 means hydrogen, hydroxy, amino, carboxy, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, means alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl respectively substituted, or means one of the following groupings, -S02-NH-R5, -NH-S02-R7, -N (S02-R7) 2, -N (S02-R7) (CO-R5), n means 0, 1 or 2, Q1 means O or S, and Q2 means 0, S, NH or N-alkyl, R5 means hydrogen or means alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl substituted respectively where appropriate R6 means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl substituted respectively where appropriate, R7 signifies alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl substituted, respectively, if appropriate, and Z means one of the heterocyclic groups if - guidelines: (Zl) (Z2) (z3) (Z) < zs > (Z6) (z10) < Z "> < Z" > (Z1d) < Z ") (z18) (Z (z23) (z24) (Z2S) (Z26) (Z27) (Z28) (z29) (z30) ) (z34) (z35) (z36) where, respectively Q1 and Q2 have the meaning indicated above, R8 means hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or means alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, cycloalkyl or cycloalkylalkyl respectively substituted, and R9 signifies hydrogen, hydroxy, amino, cyano, or means alkyl, alkenyl, alkynyl, alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl substituted respectively where appropriate, where appropriate to denote two contiguous residues -R8 and R8, R9 and R9 or R8 and R9- together alkanediyl (algenylene) or oxaalkanediyl, and the individual residues R8 and R9 may have -in as long as they are contained more than once in the same heterocyclic grouping, the same meanings or meanings differ in the scope of the definition terior, with the exception of the compounds N- [5-chloro-2- (2,5-dihydro-3,4-dimethyl-2,4-dioxo-lH-pyrrol-1-yl) -phenyl] -acetamide, N - [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) -5-trifluoromethyl-phenyl] -2,2-dimethyl-propanoamide and N- [2- (5-diethylamino-3-t-butyl-lH-1, 2,4-triazol-1-yl) -5-trifluoromethyl-phenyl] -acetamide.

2. - Process for obtaining the aromatic amino compounds of the general formula (I) wherein R1, R2, R3, R4 and Z have the meanings indicated in claim 1, characterized in that aromatic amino compounds of the general formula (II) are reacted wherein R3, R4 and Z have the meaning indicated above and A1 means hydrogen, hydroxy, amino, alkyl, alkoxy, alkylamino, or dialkylamino, with electrophilic compounds of the general formula (III), XHET in which R2 has the meaning indicated above and X means halogen, and the compounds thus obtained of the general formula (I) are optionally converted, according to customary methods, to other compounds of the general formula (I) according to the definition indicated above.

3. - Aromatic amino compounds of the general formula (II), characterized in that R3, R4 and Z have the meanings indicated in claim 1 and A1 means hydrogen, hydroxy, amino, alkyl, alkoxy, alkylamino or dialkylamino.

4. - Aromatic nitro compounds of the general formula (IVa), characterized in that R3, R4 and Z have the meanings indicated in claim 1.

5.- Aromatic nitro compounds of the general formula (IVb), characterized in that R3, R4 and Z have the meanings indicated in claim 1.

6.- Herbicidal agents, characterized in that they have a content in at least one aromatic amino acid of the formula (I) according to claim 1.

7. - Process for the fight against undesirable plants, characterized in that aromatic amino compounds of the formula (I) according to claim 1 are allowed to act on the undesirable plants and / or on their environment.

8. Use of aromatic amino compounds of the formula (I) according to claim 1, for the control of undesirable plants.

9. - Method for obtaining herbicidal agents, characterized in that aromatic amino compounds of the formula (I) according to claim 1 are mixed with extenders and / or surfactants.