MXPA01000267A - Substituted phenyl uracils - Google Patents

Abstract

The invention relates to novel substituted phenyl uracils of general formula (I) wherein n, Q, R1, R2, R3, R4, R5 and X have the meanings given in the description, to methods and novel intermediate products for producing said substituted phenyl uracils and to their use as herbicides.

Description

SUBSTITUTE FENILURACILS FIELD OF THE INVENTION The invention relates to new substituted phenyluracils, to processes for their preparation and to their use as herbicides.

Background of the Invention Certain substituted aryluracils are already known from the literature (of patents) (see EP-A-255047, EP-A-260621, EP-A-408382, EP-A-438209, EP-A-473551, EP-A-517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, WO-A-98/41093, US-A-4979982, US-A-508 08, US-A-5127935 , US-A-5154755, US-A-5169430, US-A-5486610, US-A-5356863). However, these compounds have not acquired any special significance up to the present.

DETAILED DESCRIPTION OF THE INVENTION New substituted phenyluracils of the general formula (I) have now been found REF. : 126564 wherein n means the numbers 0, 1, 2, 3, 4 or 5, means 0 (oxygen), S (sulfur), SO, S02, NH or N (alkyl), means hydrogen, amino or alkyl, if appropriate substituted, R 'means carboxy, cyano, carbamoyl, thiocarbamoyl or means substituted alkyl or alkoxycarbonyl, if appropriate, means hydrogen, halogen or optionally substituted alkyl, R4 means hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, R- means cyano , carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy substituted respectively, and X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl respectively substituted, if appropriate - having X, in the case where n is greater than 1, in the individual possible compounds also meanings different from those indicated. In the definitions the hydrocarbon chains, such as alkyl - even in combination with heteroatoms, as in alkoxy - are respectively straight-chain or branched chain. Insofar as the compounds according to the invention of the general formula (I) contain substituents with asymmetric carbon atoms, the invention relates respectively to the R enantiomers and S enantiomers, as well as arbitrary mixtures of these enantiomers, especially the racemates. Preferably, 5 A means alkanediyl (alkylene) having 1 to 6 carbon atoms or cycloalkanediyl having 3 to 6 carbon atoms, each optionally substituted by halogen or -in the case where n means 1- also means a single bond or is linked to Ar through an alkane group with 1 to 3 carbon atoms. Preferably, n means the numbers 0, 1, 2, 3 or 4, preferably, Q means 0 (oxygen), S (sulfur), SO, S02 / NH or N (alkyl having 1 to 4 carbon atoms), preferably R1 means hydrogen, amino or alkyl having 1 to 20 carbon atoms, optionally substituted by cyano, carboxy, fluorine, chlorine, by alkoxy with 1 to 4 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms; preferably, ^ ¡^ Y ^^^^ x ^^^^^^^^^^^^^^ .Ife, ^ R 'means carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl of 1 to 4 carbon atoms or alkoxy- carbonyl having 1 to 4 carbon atoms substituted, where appropriate, by cyano, fluorine, chlorine or alkoxy with 1 to 4 carbon atoms, preferably R represents hydrogen, fluorine, chlorine, bromine or means alkyl with 1 to 4 carbon atoms carbon atoms substituted, if appropriate, by fluorine or chlorine; preferably, R 'signifies hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, preferably R- means cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms or alkoxy with respectively 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine and / or by chlorine; preferably, X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylamino with 1 to 6 carbon atoms, each optionally substituted by hydroxy, by cyano, by carboxy, by carbamoyl, by fluorine, by chlorine, by alkoxy 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, by alkyl carbonyl with 1 to 4 carbon atoms, by alkoxy-carbonyl with 1 to 4 carbon atoms, by alkenyl-oxycarbonyl with 2 to 4 carbon atoms, by alkynyl-oxycarbonyl with 2 to 4 carbon atoms, alkylamino-carbonyl with 1 to 4 carbon atoms , by di- (C 1 -C 4 -alkyl) -aminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, means dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, means alkylamino; lcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, by fluorine, by chlorine, by bromine or by alkoxy with 1 to 4 carbon atoms means dialkylaminocarbonyl or dialkylaminocarbonyloxy with respectively 1 to 6 carbon atoms in the alkyl groups, means phenylcarbonyloxy, means alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino respectively substituted, if appropriate by fluorine, by chlorine or by bromine, or means alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl having, respectively, up to 6 carbon atoms, substituted respectively by cyano, carboxy, fluorine, chlorine, bromine or alkoxycarbonyl having 1 to 4 carbon atoms; particularly preferably, n means the numbers 1, 2 or 3; more preferably, Q means O (oxygen), S (sulfur), SO, S02, NH or N (CH3); R1 is particularly preferably hydrogen, amino or methyl or ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, more preferably R represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, where appropriate, by cyano, by fluorine, chlorine, methoxy or ethoxy, particularly preferably R; means hydrogen, fluorine, chlorine, bromine or methyl, ethyl substituted respectively by fluorine and / or by chlorine; more preferably, it means hydrogen, fluorine or chlorine; more preferably, R5 means cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, or trifluoromethyl; more preferably, X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, 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, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, etiululium, methylsulfonyl, ethylsul fonyl , methylamino, ethylamino, n- or i- propyl-amino, n-, i-, s- or t-butylamino substituted respectively by cyano, by carboxy, by carbamoyl, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy, by methyl, by ethylthio, by n- or i-propylthio, by methylsulphonyl, by etulous fonyl, by methylsulphonyl, by ethyl sulphonyl, by acetyl, by propionyl, by n - or i-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by allyloxycarbonyl, by l-buten-3-yl-oxy- - * -. carbonyl, by 2-buten-4-yl-oxycarbonyl, by propargyloxycarbonyl, by l-butyn-3-yl-oxycarbonyl, by 2-butyn-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyl-oxycarbonyl, by phenylaminocarbonyl or by Benzylaminocarbonyl, means dimethylamino or diethylamino, means acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or -propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i- propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i- 20 propylaminocarbonyloxy, respectively substituted, if appropriate, by cyano , by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy, means dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, means phenylcarbonyloxy, means acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i- propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i- propylsulphonylamino, n- i-, s- or t-butylsulfonylamino substituted respectively by fluorine or by chlorine, respectively, or means ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl respectively substituted, where appropriate, by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or by ethoxycarbonyl. Preferred according to the invention are the compounds of the formula (I), in which a combination of the meanings indicated above is preferentially presented. Particularly preferred according to the invention are the compounds of the formula (I), in which a combination of the meanings indicated above is presented in a manner .?? jB &JaS M * m - m? SaSj & S tVÍÍÍbbbbt.mMlS? m < mfm -mmítf -. 3-Mtfl, go Jfmm * 2¡)? M. L, "especially preferred. A very especially preferred group are the compounds of the formula (IA), wherein R1 means hydrogen, amino or methyl means trifluoromethyl, chlorodi-fluorine ethyl, difluoromethyl or pentafluoroethyl, R; means hydrogen, chlorine or methyl, R < means hydrogen, fluorine or chlorine, R- means cyano or thiocarbamoyl, and X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, methoxy, ethoxy, methylthio , ethylthio, methoxycarbonyl or ethoxycarbonyl respectively substituted, where appropriate, by cyano, carboxy, carbamoyl, fluorine, . - "- n? Fte3 chlorine, by methoxy, by ethoxy, by n- or i- propoxy, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by allyloxycarbonyl, by propargyloxycarbonyl, by l-buten-3- il-oxycarbonyl, by 2-buten-4-yl-oxycarbonyl, by propargyloxycarbonyl, by l-butyn-3-yl-oxycarbonyl, by 2-butyn-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or means ethenyl substituted by methoxycarbonyl or by ethoxycarbonyl. Another very especially preferred group is constituted by those compounds of the formula (IA), in which * -afe * ^ - * ± > X & amp; & amp;, £ & * r-Arv & r & r < R < R < Rl < R < R > stands for methyl, R stands for trifluoromethyl, chlorodi-fluoromethyl, difluoromethyl, or pentafluoroethyl, R stands for hydrogen, chloro, or methyl, R stands for hydrogen, fluorine or chlorine R "means fluorine, chlorine, bromine or trifluoromethyl and X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl substituted, where appropriate, by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl , by allyloxycarbonyl, by propargyloxycarbonyl, by l-buten-3-yloxycarbonyl, by 2-buten-4-yl-oxy-carbonyl, by propargyloxycarbonyl, by l-butyn-3-yloxycarbonyl, by butyne-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i- propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or means ethenyl substituted by methoxycarbonyl or by ethoxycarbonyl. Another very especially preferred group is constituted by those compounds of the Formula (IA), in which R 1 signifies hydrogen, amino or methyl, R 'means carboxy, cyano, carbamoyl, thiocarbamoyl, methoxycarbonyl or ethoxycarbonyl, R- signifies hydrogen, chlorine or methyl, means hydrogen, fluorine or chlorine, R - means cyano, thiocarbamoyl, fluorine, chlorine, bromine or trifluoromethyl, X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, methoxy, ethoxy, methylthio , ethylthio, methoxycarbonyl or ethoxycarbonyl substituted, where appropriate, by cyano, carboxy, by carbamoyl, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i- propoxy, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, 5 by allyloxycarbonyl, by propargyloxycarbonyl, by l-buten -3-yl-oxycarbonyl, by 2-buten-4-yl-oxy-carbonyl, by propargyloxycarbonyl, by l-butyn-3-yl-oxycarbonyl, by 2-butyn-4-yl-oxy-10-carbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or means ethenyl substituted by methoxycarbonyl or by ethoxycarbonyl. 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 materials or the necessary intermediates é¿? a ^^^^^^^ »^ * ^^^^ ^ ^^^^^^ * MS ^^^ respectively for 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 general formula (I) have been indicated in the following groups. Group 1.

In this case Xn has the meanings indicated in the following enumeration: 2-hydroxy, 3-hydroxy, 4-hydroxy, 2-cyano, 3-cyano, 4-cyano, 2-carhoxy, 3-carboxy, 4-carboxy, 2 -fluorine, 3-fluorine, 4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2-chloro , 3-chloro, 4-chloro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2-bromo, 3 -bromine, 4-bromo, 2-methyl, 3-methyl, 4- Vt * 8? b methyl, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2-trifluoromethyl, 3-tri fluoromethyl, 4- trifluoromethyl, 2-methoxy, 3-methoxy, 4-methoxy, 2,4-dimethoxy, 2,5-dimethoxy, 2,6-dimethoxy, 3,4-dimethoxy, 2-difluoromethoxy, 4-difluoromethoxy, 2-trifluoromethoxy, 4-trifluoromethoxy, 4-ethoxy, 4-methylthio, 4-ethylthio, 4-methoxycarbonyl, 4-ethoxycarbonyl, 4-carboxymethoxy, 4-methoxycarbonylmethoxy, 4-ethoxycarbonylmethoxy, 4-n-propoxycarbonylmethoxy, 4-i-propoxycarbonylmethoxy, 4- (1-carboxy-ethoxy), 4- (1- (methoxycarbonyl) ethoxy), 4- (l - (ethoxycarbonyl) ethoxy), 4- (1- (n-propoxycarbonyl) -ethoxy), 4 - (1- ( i-propoxycarbonyl) -ethoxy), 4- (allyloxycarbonylmethoxy), 4- (1- (allyloxycarbonyl) -ethoxy), 4- (propargyloxycarbonylmethoxy), 4- (l - (benzyloxycarbonyl) ethoxy), 4- (benzyloxycarbonyl-ethoxy), 4- (1- (benzyloxycarbonyl) ethoxy), 4- (aminocarbonylmethoxy), 4- (methylaminocarbonylmethoxy), 4- (ethylaminocarbo-nylmethoxy), 4- ( n-propylaminocarbonyl lmetoxy), 4- (i-propyl-aminocarbonylmethoxy), 4- (dimethylamino-carbonylmethoxy), 4- (1- (methylaminocarbonyl) ethoxy), 4- (1- (ethylaminocarbonyl) -ethoxy), 4- (1- (n- propylaminocarbonyl) -ethoxy), 4- (1- (i-propylaminocarbonyl) -ethoxy), 4- (1- (dimethylaminocarbonyl) -ethoxy), 4- (2-methoxycarbonyl-ethenyl), 4- (2 -ethoxycarbonyl-ethenyl). ' • Group 2.

Xn has in this case the meanings indicated above in group 1. Group 3.

Xn has in this case the meanings indicated above in group 1.

Group 4 Xn has in this case the meanings indicated above in group 1. Group 5.

Xn has in this case the meanings indicated above in group 1.

M¡? I »? Jj *» á »í» attáaMi, mkAA ^, Group 6 Xn has in this case the meanings indicated above in group 1. Group 7. fifteen twenty Xn has in this case the meanings indicated above in group 1.

Group 8 Xn has in this case the meanings indicated above in group 1. Group 9. fifteen Xn has in this case the meanings indicated above in group 1.

Group 10 Xn has in this case the meanings indicated above in group 1. Group 11.

Xn has in this case the meanings indicated above in group 1.

Group 12 Xn has in this case the meanings indicated above in group 1. Group 13.

Xn has in this case the meanings indicated above in group 1.

»Jj to $ 8 &x * ~ ^ a ^ -.

Group 14 Xn has in this case the meanings indicated above in group 1. Group 15.

Xn has in this case the meanings indicated above in group 1.

The new substituted phenyluracils of the general ula (I) have interesting biological properties. These are characterized especially by a powerful herbicidal activity. The new substituted phenyluracils of the general ula (I) are obtained, if (a) halogen phenyluracils of the general ula (II) are reacted wherein R1, R2, R3, R4 and R5 have the meaning indicated above and X1 means halogen, with aryl compounds of the general ula (III) wherein n, Q and X have the meaning indicated above, or with metal salts of the compounds of the general ula (III) -, optionally in the presence of an auxiliary agent of the reaction, and optionally, in the presence of a diluent, or if (b: esters of ammoalkenoic acids of the general ula (IV) are reacted wherein R2 and R3 have the meaning indicated above and R means alkyl, aryl or arylalkyl, with aryl isocyanates of the general ula (V) wherein n, Q, R4, R5 and X have the meaning indicated above, or with aryl urethanes (arylcarbamates) of the general ula (VI), wherein n, Q, R5, R6 and X have the meaning indicated above and R means alkyl, aryl or arylalkyl, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent , or if (c) N-aryl-1-alkoxycarbonylamino-maleimides of the general ula (VII) are reacted, l¡ ^ tó ^ ß í ^^ ¿^ £ wherein n, Q, R3, R4, R5 and X have the meaning indicated above, and R 'means alkyl, with metal hydroxide in the presence of water and, if appropriate, in the presence of an organic solvent, or if (d) ) substituted phenyluracils of the general ula (Ia) are reacted wherein n, Q, R2, R3, R4 R5 and X have the meaning indicated above, with l-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general ula (VIII) X2-A? (VIII) wherein A1 means optionally substituted alkyl and X2 means halogen or the grouping -0-SO? -O-A1, optionally in the presence of a reaction auxiliary, and optionally, in the presence of a diluent and, if appropriate, electrophilic or nucleophilic reactions or oxidation or reduction reactions are usually carried out in the context of the definition of the substituents. The compounds of the general ula (I) can be converted, according to customary methods, into other compounds of the general ula (I) according to the above definition, example by esterification or hydrolysis (example X: OCH 2 COOH? OCH 2 COOC 2 H 5, OCH (CH 3 ) COOCH3? OCH (CH3) COOH), reaction with dicyano or with bisulfite (example R5: Br-CN, CN-CSNH2), transation of carboxycompounds into other carboxylic acid derivatives according to customary methods (example R2: COOH? CN, CN? CSNH2, COOH COOCH3, COOCH3 - >; CONH2); see the obtaining examples). If, for example, l- (4-cyano-2, 5-difluorophenyl) -4-chlorodifluoromethyl-3,6-dihydro-2,6-dihydro-2,6-dioxo-l (2H) -pyrimidine is used, for example. and the ethyl l- (4-hydroxy-phenoxy) -propionate, as starting materials, the development of the reaction in the case of process (a) according to the invention can be schematized by means of the following formula scheme: If, for example, methyl 3-amino-4, 4, -trifluoro-crotonate and 4-cyano-2-fluoro-5-phenoxy-phenylisocyanate are used as starting materials, the development of the reaction in the case of process (b) according to the invention by means of the following formula scheme: If, for example, methyl [l- (2,4-dichloro-5-phenylthio-phenyl) -2,5-dioxo-2, 5-dihydro-1H-pyrrol-3-yl] -carbamidate is used as starting product can be schematized the development of the reaction in the case of the procedure according to the ii x & £ * £ & * »invention by means of the following formula scheme: If, for example, l- [2-chloro-4-tri-fluoromethyl-5- (4-methoxycarbonyl-methoxy-phenoxy) -phenyl] -4-difluoromethyl-3,6-dihydro-2,6 is used -dioxo-l (2H) -pyrimidine and methyl bromide as starting products, the development of the The reaction in the case of the process (d) according to the invention is carried out by means of the following formula scheme: The halogen phenyluracils to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R 1, R 2, R 3, R 4 and R 5 have especially those meanings which have been mentioned above in a preferred manner, more preferably or very particularly preferably for R 1, R 2, R 3, R 4 and R 5 in relation to the description of the compounds of the RUBETHYJJ ^ A *? * - * R * »., Formula (I) according to the invention; preferably X1 means fluorine or chlorine, especially fluorine. The starting materials of the general formula (II) are known and / or can be prepared according to processes known per se (cf. EP-A-648749). The aryl compounds, to be used as starting materials in the process according to the invention, are generally defined by means of formula (III). In formula (III), n, Q and X have especially those meanings which have already been mentioned above in a preferred manner, more preferably, very particularly preferably and very particularly preferably for n, Q and X in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (III) are chemical products for known syntheses. The esters of the aminoalkenoic acids to be used as starting materials in the process (b) according to the invention for the & * & & * & amp; amp; amp; & amp; & amp; The compounds of the general formula (I) are generally defined by the formula (IV). In the general formula (IV), R2 and R3 have especially those meanings which have already been mentioned above in a preferred manner, particularly preferably and very particularly preferably for R2 and R3 in relation to the description of the compounds of the formula General (I) according to the invention; preferably R means alkyl with 1 to 4 carbon atoms, phenyl or benzyl, especially means methyl or ethyl. The starting materials of the general formula (IV) are known and / or can be prepared according to known processes (cf. J. Heterocycl, Chem. 9 (1972), 513-522). The arylisocyanates, to be used as starting materials in the process (b) according to the invention, are generally defined by the formula (V). In the general formula (V), n, Q, R4, R5 and X have especially those meanings which have already been mentioned above in a preferred manner, particularly preferably and very particularly preferably for n, Q, R4, R5 and X in relation to the description of the compounds of the »» - .- ^. S-S-MM »general formula (I) according to the invention. The starting materials of the general formula (V) are not yet known from the literature; they constitute, as new products, also an object of the present application. The new arylisocyanates of the general formula (V) are obtained if the aniline derivatives of the general formula (IX) are reacted. wherein n, Q, R4, R5 and X have e-1 meaning as indicated above, with phosgene in the presence of a diluent, such as for example chlorobenzene, at temperatures ranging from -20 ° C to + 150 ° C (see also EP-A-648749). The aryl urethanes, to be used as starting materials if necessary in the process (b) ading to the invention, are generally defined by means of formula (VI). In the general formula (VI), n, Q, R4, R5 and X have especially those meanings that have already been mentioned above, preferably, particularly preferably or very particularly preferably for n, Q, R4, R5 and X in relation to the description of the compounds of the general formula (I) ading to the invention; preferably R means alkyl with 1 to 4 carbon atoms, phenyl or benzyl, especially means methyl or ethyl. The starting materials of the general formula (VI) are not yet known from the literature; they constitute, as new products, also an object of the present application. The new aryl urethanes of the general formula (VI) are obtained, if they are reacted derivatives of the aniline of the formula (IX) where n, Q, R 'and X have the meaning above ÍfiJ ** JlitáW% - * ¿& ttiS?? R 2 indicated, with chlorocarbonyl compounds of the general formula (X) RO-CO-C1 (X) wherein R has the abovementioned meaning, if appropriate in the presence of an acid acceptor, such as, for example, pyridine and, if appropriate, The presence of a diluent, such as for example methylene chloride, at temperatures between -20 ° C and + 100 ° C (see the preparation examples). The aniline derivatives, necessary as starting materials of the general formula (I) are known and / or can be prepared ading to known processes (see the publications Justus Liebigs Ann. Chem. 740 (1970), 169-179, US-A-3715395; US-A-391 418; DE-A-2748554; DE 3736089). It is not yet known, and constitute, as a new product, an object of the present application, the aniline derivatives of the general formula (IXa) wherein n, R4 and X have the meaning indicated above and Y means cyano, thiocarbamoyl or trifluoromethyl. The new aniline derivatives of the general formula (IXa) are obtained if they are reacted anilines of the general formula (XI) wherein R4, X1 and Y have the meaning indicated above, with aryl compounds of the general formula (III), "° t> (III) wherein n, Q and x have the meaning indicated above, - or with metal salts of compounds of the general formula (III) - optionally in the presence of an auxiliary reaction agent such as, for example, sodium hydride, and in the case of a diluent, such as for example n-methyl-pyrrolidone, at temperatures between 0 ° C and 150 ° C (see the preparation examples). The N-aryl-1-alkoxycarbonylamino-maleimides, to be used as starting materials, in carrying out the process (c) ading to the invention, for the preparation of the compounds of the general formula (I), are generally defined by middle of the formula (VII). In the general formula (VII), n, Q, R3, R4, R5 and X have especially those meanings that have already been mentioned above as being preferred, especially preferred or very particularly preferred for n, Q, R3, R4, R5 and X in relation to the description of the compounds of the general formula (I) ading to the invention; preferably R4 means alkyl with 1 to 4 carbon atoms, especially means methyl or ethyl. The novel N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) are obtained, if they are reacted (alkyl 2,5-dioxo-2, 5-dihydro-furan-3-yl) -carbamidates of the general formula (XII) wherein R 3 has the above-indicated meaning and R 'means alkyl (especially means methyl or ethyl), with aniline derivatives of the general formula (IX) wherein n, Q, R4, R5 and X have the meaning indicated above, if appropriate in the presence of a diluent, such as for example acetic acid, at temperatures between 0 ° C and 200 ° C, preferably between 50 ° C C and 150 ° C. The starting materials of the general formula (XII) are known and / or can be prepared according to known processes (cf. DE 19604229). The substituted phenyluracils, to be used as starting materials in the process (d) according to the invention for the preparation of the compounds of the formula (I), are generally defined by the formula (la). In formula (la) n, Q, R2, R3, R4, R5 and X have especially those meanings which have already been mentioned above especially, particularly preferably or very particularly preferably for n, Q, R2, R3, R4, R5 and X in relation to the description of the compounds of the formula (I) according to the invention. , • > "if fif The starting materials of the general formula (la) for process (b) constitute, as new products, also an object of the present application, these can be prepared according to the procedures (a), (b), and (c) according to the invention. The alkylating agents to be further employed as starting materials in process (d) according to the invention are generally defined by means of formula (VIII). In the formula (VIII), A110 means preferably alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms and X2 means chlorine, bromine, iodine, methylsulfonyloxy or ethanol. ilsulfonyloxy; especially A1 means methyl, ethyl, n- or i-propyl substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy and X2 means chlorine, bromine, iodine, methylsulfonyloxy, ethyl sulphonyloxy. The starting materials of the formula 20 (VIII) are organic chemical products for known syntheses. The processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out the processes (a), (b) (c) and (d) according to the invention come into consideration, in addition to water, first and foremost, 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, carbon tetrachloride, ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl-ketone; nitriles, such as acetonitrile, propionitrile or but ironitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl fos forotriamide; esters such as methyl acetate or ethyl acetate, Sulfoxides, such as dimethylsulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylenealkylmonomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

Sanate »fca Sk» ..

Suitable reaction aids for processes (a), (b), (c) and (d) according to the invention are generally the bases or acceptors of customary inorganic or organic acids. These include, for example, 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 calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate , n-, i-, s- or sodium or potassium t-butanolate, n-or i-propanolate, ethanolate, n-or i-propanolate; also basic organic nitrogenous compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldisopropylamine, N, N-dimethyl-cyclohexylamino, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-2-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-di -methyl-pyridine, 5-yl-2-methyl-pyridine, 4- x: - &., < > and Xi:? ^,% < 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). Other phase-transfer catalysts are also suitable as process auxiliaries for the processes according to the invention. Examples of such catalysts include: tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogensulfate, methyltrichloroammonium chloride, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, benzyltrimethylammonium chloride. , benzyltriethylammonium chloride, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyl tributylammonium chloride, benzyltributyl ammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecyl phosphonium bromide, butyltriphenyl phosphonium chloride , ethyltrioctylphosphonium bromide, tetraphenyl phosphonium bromide. The reaction temperatures in the carrying out of processes (a), (b), (c), (d) 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 processes according to the invention are 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 processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of an auxiliary agent of the reaction and the reaction mixture is stirred, in general, for several hours at the necessary temperature. The preparation is 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 plants Next 10: Bad dicotyledonous herbs of the following types: 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, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Cultures of dicotyledonous species: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

»V» -a3fc j-ttMí-i - i- »- 5 * an < «Z- * ~ + ?? riák £ &mA + .m ~. < -. - -. > -. -.,. x ", **., j • iftiHIÉBBwMififi fi c. - -, c. JUi-.t«. «J5g -.-. ft t Bad monocotyledonous herbs of the classes: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleochaps, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active products according to the invention, however, is not limited in any way to these classes, but they extend in the same way also over 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, compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sporting paths and on meadows and to selectively control weeds in mono-annual crops. The compounds of the formula (I) according to the invention exhibit a potent herbicidal activity and a broad spectrum of activity when used on the soil and on the aerial parts of the plants. plants. They are suitable in a certain proportion also for the selective fight against monocotyledonous and dicotyledonous weeds in monocotyledonous cultures both in the pre-shoot procedure and in the post-emergence procedure. The active products can be transformed into the 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 products with spreader materials, that is, with liquid solvents and / or solid diluents, if necessary, 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. As liquid solvents enter Especially in consideration: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or chloride of methylene, the aliphatic hydrocarbons, such as cyclohexane, or the paraffins, for example, the fractions of crude petroleum, the alcohols such as butanol, or glycol, as well as their esters and ethers, the ketones, such as acetone, Methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, as well as water.

Suitable solid excipients are: for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorilloni ta or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed, aluminum oxide and silicates, as solid excipients for granulates can be used broken and fractionated natural minerals such such as calcite, marble, pumice stone, 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; As emulsifiers and / or foam generators, non-ionic and anionic emulsifiers, such as polyoxyethylated fatty acid esters, polyoxyethylated fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as albumin hydrolysis products; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose.

In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and phospholipids can be used. synthetic Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace nutrients, such as iron salts, 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 mixtures of Suitable mixtures for the mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Car fentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosul furon, Clethodim, Clodinafop (- propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl) , Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2, 4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-me t ilo}, Diclosulam, Diethatyl (ethyl), Difenzoquat, Diflufenican, Di flufenzopyr, Dimefuron, Dimepiperat e, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), 5 Ethofumesate, Ethoxyfen, Ethoxysul furon, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (- isopropyl), Flamprop (-isopropyl-L), Flamprop (- methyl), Flazasulfuron, Fluazi fop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyrsul furon (-meti lo, -sodium), Flurenol (- butyl), Fluridone, Fluroxypyr (-meti) lo), Flurprimidol, Flurtamone, Fluthiacet (-met i lo), Fluthiamide, Fo esafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (- ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosul furon (ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-sodium), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sul fosul furon, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thi fensulfuron (-met ilo), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-metyl), Triclopyr, Tridiphane, ^^ ¡^^^^ ^^^^^^^^^^^^^^ Trifluralin and Triflusulfuron. A mixture with other known active ingredients is also possible, 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 verified in a usual manner, for example by irrigated, atomized, sprayed, scattered. 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 hectare. The preparation and use of the active compounds according to the invention are illustrated by means of the following examples.

Preparation examples Example 1.

(Procedure (a)) 2.5 g (10 mmol) of 4-methoxyphenol are placed in 50 ml of dimethylsulfoxide and combined with 1.6 g of sodium hydride (60% strength). The mixture is stirred for 30 minutes at room temperature (about 20 ° C). Then 3.2 g (10 mmol of 4- (3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidin-1-yl) -2,5-difluorobenzonitrile are added. The reaction mixture is stirred for 18 hours at 60 ° C and then poured on an approximately equal volume amount of hydrochloric acid IN. The crystalline product formed is isolated by suction filtration, stirred with the mixture of 30 ml of ethyl acetate and 300 ml of diethyl ether and filtered off by suction to dryness. The organic mother liquors are concentrated by evaporation in a vacuum of the water pump and the residue is worked up by column chromatography (silica gel, chloroform / ethyl acetate, volume: 2: 1). The first fraction, obtained in this case, is concentrated by vacuum evaporation of the water pump, the residue is dissolved in boiling methylene chloride, after cooling it is separated by After decanting the supernatant, the residue is stirred with diethyl ether / diisopropyl ether and the crystalline product is isolated by suction filtration. 0.90 g (21% of theory 9 of 4- (3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimid-20-din-1-yl) -5-fluoro-2 is obtained. - (4-methoxy-phenoxy) -benzonitrile with a melting point of 84 ° C. *** »*** -, **» * & "< -1. üti > > »-MI > Example 2 (Procedure (b)) A mixture consisting of 0.50 g (1.2 mmol) of 4- (3,6-d-hydroxy-1,6-dioxo-4-trifluoromethyl-1 (2H) - is heated at reflux for 15 hours. pyrimidin-1-yl) -5-fluoro-2- (4-methoxy-phenoxy) -benzoni tryl, 0.20 g (1.8 mmol) of dimethyl sulfate, 0.30 g (2.4 mmol) of potassium carbonate and 100 ml of acetone and then concentrated by vacuum evaporation of the water pump. The residue is shaken with 50 ml of 1N hydrochloric acid / 50 ml of ethyl acetate, the organic phase is separated, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation to the water pump vacuum, dissolved in ethyl acetate, washed with 5% aqueous solution of disodium hydrogen phosphate, dried over sodium sulfate and filtered. The filtrate is Concentrate by evaporation to the vacuum of the water pump, the residue is stirred with petroleum ether and the solvent is carefully removed by vacuum distillation of the water pump. 0.3 g (57% of theory) of 4- (3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidin-1-yl) -5-fluoro are obtained. -2 (4-methoxy-phenoxy) -benzonitrile with a melting point of 62 ° C. Analogously to the examples of Obtaining 1 and 2 as well as according to the general description of the preparation processes according to the invention, for example, also compounds of the formula (I) indicated in Table 1 below can be prepared. fifteen Table 1: Examples of compounds of the formula (I) 15 20 ^^^^^^^^^^ g ^^. ^^^^^^. ^^ g ^^^^^ ^^^^^^^^^^^^^ - £ t ^^ ^? ^^^ _ ^ ggg ^ 'H? F &? Z? Z £, .-? «Fcy- .- *, 10 fifteen twenty It-Vt & A ^ ¡¡^ - - * • ~ '- ^^^^ g ^^ ^ Hí ^^^^ 10 fifteen Starting materials of the formula (VI) Example (VI-1). twenty 2.8 g (11 mmol of l-amino-4-cyano-2-fluoro-5- (-methoxy-phenoxy) -benzene in 100 ml of methylene chloride are added with 1.7 g of pyridine and are combined at room temperature ( about 20 ° C), with 1.25 g (12 mmol) of ethyl chloroformate The mixture is stirred for 2 hours at room temperature and then shaken with IN hydrochloric acid The organic phase is concentrated by vacuum evaporation of the tube of water, the The residue is crystallized from diethyl ether / diisopropyl ether and the solid product isolated by suction filtration. 1.2 g (34% of theory) of N- (4-cyano-2-fluoro-5- (4-methoxyphenoxy) -phenyl) -O-ethyl-15-carbamate are obtained. XH-NMR (D6-DMSO, d): 7.85 and T.89 ppm. Starting materials of the formula (IX): Example (IX-1). twenty 1.3 g (10 mmol) of 4-methoxy-phenol are combined in 100 ml of N-methyl-pyrrolidone at room temperature with 0.50 g of sodium hydride (60% strength) and, after a short period of time, with 1.5 g of 4-cyano-2, 5-difluoro-aniline. The reaction mixture is then stirred for 20 hours at 100 ° C. After cooling, it is diluted with water and then with IN hydrochloric acid and, after 2 hours of stirring, the solid product is isolated by suction filtration and dried on clay. 1.9 g (73% of the theory) of 1- amino-4-cyano-2-fluoro-5- (4-methoxy-phenoxy) -benzene are obtained with a melting point of 135 ° C. Analogously to example (IX-1), it is also possible, for example, to prepare compounds of the general formula (I) indicated in the following table 2: Table 2: Examples of compounds of the formula (IX) Application examples: Example A. Pre-bud test. 15 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 solvent amount, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. ^^^^^^^^^^^^^ í Á ^^^^^^^^^^^ j ^^^^^ ^^^ seeds of the test plants were sown in normal soil. After 24 hours, the soil is irrigated with the preparation of active product, so that the desired amount of active product per unit area is applied respectively. The concentration of the sprayable broths will be chosen in such a way that the quantities of active product desired in each case are applied in 1000 liters of water per hectare. 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, for example, the compound according to the preparation examples 4 and 6 shows a very potent effect against weeds.

Example B.

Post-emergence trial. Solvent: 5 parts by weight of acetone ^^^ gj ^^ gj ^^^^^^^^^ 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. 15 cm, so that in each case, the desired amounts of active compound applied per unit area - 10 The preparation of active compound Test plants which have a height of 5 pulverized. The concentration of sprayable broths are chosen in such a way that the desired quantities of active product are applied in each case in 1000 liters of water / ha. After three weeks the degree of damage of the plants is evaluated in% damage compared with the development of untreated controls. They mean: 0% = no effect (same as untreated controls) 100% = total destruction.

^ Mbat ^ a ^. * & * * *** & *, ^ ttam? tíli a ^ tA? i-ám In this test shows, for example, the compound according to the obtaining examples 4 and 6 a very potent effect against weeds . 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 (17)

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

1. Substituted phenyluracils of the general formula (I) characterized because n means the numbers 0, 1, 2, 3, 4 or 5, Q means O (oxygen), S (sulfur), SO, S02, NH or N (alkyl), R 1 signifies hydrogen, amino or optionally substituted alkyl, R 2 means carboxy, cyano, carbamoyl, thiocarbamoyl or means alkyl or alkoxycarbonyl substituted respectively where appropriate, R 3 signifies hydrogen, halogen or alkyl in ^^ > • *** * substituted case given, R4 means hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, R5 means cyano, carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy substituted respectively, and X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, diakinolaminocarbonylloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl, respectively substituted if appropriate, may have X, in the case where n is greater than 1, in the possible individual compounds also meanings different from those indicated.

2. Substituted phenyluracils according to claim 1, characterized in that n means the numbers 0, 1, 2, 3 or 4, ? &amp?? ftgm? * YES., MLJ (! bM »Q means O (oxygen), S (sulfur), SO, S02, NH or N (alkyl with 1 to 4 carbon atoms), R1 means hydrogen, amino or C 1 -alkyl optionally substituted by cyano, by carboxy, by fluorine, by chlorine, by alkoxy with 1 to 4 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms, R 2 means carboxy, cyano , carbamoyl, thiocarbamoyl or alkyl of 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms substituted, where appropriate, by cyano, fluorine, chlorine or alkoxy with 1 to 4 carbon atoms, R3 is hydrogen , fluorine, chlorine, bromine or means alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine or chlorine, R 4 is hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, R 5 is cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 respectively carbon atoms, respectively replaced, if necessary, by fluorine and / or chlorine; means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylamino with 1 to 6 carbon atoms, each substituted respectively given by hydroxy, by cyano, by carboxy, by carbamoyl, by fluorine, by chlorine, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, for alkylcarbonyl with 1 to 4 carbon atoms, for alkoxycarbonyl with 1 to 4 carbon atoms, for alkenyl-oxycarbonyl with 2 to 4 carbon atoms, for alkynyloxycarbonyl with 2 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms, for di- (alkyl with 1 to 4 carbon atoms) -aminocarbonyl, for phenoxycarbonyl, for benzyloxycarbonyl, for phenylaminocarbonyl or for ^^? i ^ A? ii ^^^ benzylaminocarbonyl, means dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, means alkylcarbonyl, alkoxycarbonyl, 5-alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy having 1 to 6 carbon atoms in the alkyl groups, each substituted, where appropriate, by cyano, Fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms means dialkylaminocarbonyl or dialkylaminocarbonyloxy with 1 to 6 carbon atoms in each group Alkyl, means phenylcarbonyloxy, means alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino substituted respectively by fluorine, chlorine or bromine, or Alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl with respectively up to 6 carbon atoms, respectively substituted in each case by cyano, by carboxy, by fluorine, by chlorine, by bromine or by alkoxycarbonyl with 1 to 4 carbon atoms.

3. Substituted phenyluracaccording to claim 1, characterized in that n denotes the numbers 1, 2 or 3; Q means 0 (oxygen), S (sulfur), SO, S02, NH or N (CH3); R1 means hydrogen, amino or methyl or ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, if appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, R2 means carboxy , cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i- propyl, methoxycarbonyl or ethoxycarbonyl, n- or i-propoxycarbonyl substituted in each case optionally cyano-, fluorine, chlorine, methoxy or ethoxy, R3 means hydrogen, fluorine, chlorine, bromine or methyl, ethyl substituted respectively by fluorine and / or by chlorine; R4 means hydrogen, fluorine or chlorine; R5 means cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, or trifluoromethyl; X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, 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, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i - propyl-amino, n-, i-, s- or t-butylamino substituted, where appropriate, by cyano, by carboxy, by carbamoyl, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy , methyl, ethylthio, n- or i-propylthio, by metl finilo by etl fonilo, methylsulfonyl, by etl fonilo, acetyl, propionyl by, n- or i- butyroyl by, methoxycarbonyl, ethoxycarbonyl, by n- or i-propoxycarbonyl, by allyloxycarbonyl, by l-buten-3-yl-oxycarbonyl, by 2-buten-4-yl-oxycarbonyl, .- * * * * * * * M ^ SS ^ s by propargyloxycarbonyl, by l-butyn-3-yloxycarbonyl, by 2-butyn-1-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyl-oxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, means dimethylamino 10 or diethylamino, it means acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, 15 propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i- propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i- propylaminocarbonyloxy, substituted In each case, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, means dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or ^ fe ^^^^^^^^^^^^^^^^^^^^ fe ^^^^^^^^^. diethyl inocarboniloxi means phenylcarbonyloxy, it means acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, etoxicarbonilammo, n- or i- propoxycarbonylamino, fonilamino, ethylsulfonylamino, n- or í- metl propylsulfonylamino, n- i-, s- or t - butylsulfonylamino substituted in each case optionally fluorine- or 10 chlorine, or represents ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl substituted respectively optionally cyano-, carboxyl, fluorine, chlorine, 15 methoxycarbonyl or by ethoxycarbonyl.

4. Substituted phenyluracaccording to claim 1, characterized by means of the general formula (IA) wherein R1 signifies hydrogen, amino or methyl R2 means trifluoromethyl, chlorodi fl uoromethyl, difluoromethyl or pentafluoroethyl, R3 signifies hydrogen, chlorine or methyl, R4 signifies hydrogen, fluorine or chlorine, R5 signifies cyano or thiocarbamoyl, and X signifies hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, or means methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl respectively substituted by cyano, by carboxy, by carbamoyl, by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl, propargyloxycarbonyl, l-buten-3-yloxycarbonyl, by 2-buten-4-yl-oxycarbonyl, by propargyloxycarbonyl, by l-butyn-3-yl-oxycarbonyl, by 2-butyn-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or means ethenyl substituted by methoxycarbonyl or by ethoxycarbonyl.

5. Substituted phenyluracils according to claim 4, characterized in that R1 signifies methyl, R1 signifies trifluoromethyl, chlorodi fl uoromethyl, difluoromethyl or pentafluoroethyl, means hydrogen, chlorine or methyl, R4 signifies hydrogen, fluorine or chlorine, R- signifies fluorine, chlorine, bromine or trifluoromethyl and X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, or means methyl, '^ "^ - ^ - *. * M-Í HSa. £ ethyl, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl respectively substituted, where appropriate, by cyano, by carboxy, by carbamoyl, by fluorine, by 5 chlorine, by methoxy, by ethoxy, by n- or i- propoxy, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by allyloxycarbonyl, by propargyloxycarbonyl, by l-buten-3-yl-10-oxycarbonyl, by 2-buten 4-yl-oxy-carbonyl, by propargyloxycarbonyl, by l-butyn-3-yl-oxycarbonyl, by 2-butyn-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i- 15-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or by ethenyl 20 substituted by methoxycarbonyl or by ethoxycarbonyl. < *. * - »f --- ^ t ^ |« ¡ga ^ ^^^ ...: ..- SM »» ... ^ fa - ^ ..... .Im? I j & m. '^ .i ..

6. Substituted phenyluracils according to claim 4, characterized in that R 1 signifies hydrogen, amino or methyl, R 2 signifies carboxy, cyano, carbamoyl, thiocarbamoyl, methoxycarbonyl or ethoxycarbonyl, R 3 signifies hydrogen, chlorine or methyl, R 4 signifies hydrogen, fluorine or chlorine, R 5 means cyano, thiocarbamoyl, fluorine, chlorine, bromine or trifluoromethyl, X means hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio 15 methoxycarbonyl or ethoxycarbonyl respectively substituted, where appropriate, by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, by allyloxycarbonyl, by propargyloxycarbonyl, by l-buten-3-yloxycarbonyl, by 2-buten-4-yl-oxy-carbonyl, by propargyloxycarbonyl, by 1-butyn-3-yl- oxycarbonyl, by 2-butin-4-yl-oxycarbonyl, by methylaminocarbonyl, by ethylaminocarbonyl, by n- or i-propylaminocarbonyl, by dimethylaminocarbonyl, by diethylaminocarbonyl, by phenoxycarbonyl, by benzyloxycarbonyl, by phenylaminocarbonyl or by benzylaminocarbonyl, or means ethenyl substituted by methoxycarbonyl or by ethoxycarbonyl.

7. Substituted phenyluracils according to one of claims 1 to 6, characterized in that n means 1.

8. Substituted phenyluracils according to one of claims 1 to 7, characterized in that R2 means trifluoromethyl.

9. Substituted phenyluracils according to one of claims 1 to 8, characterized in that R4 means fluorine.

10. Substituted phenyluracils according to one of claims 1 to 9, characterized in that R5 is cyano or thiocarbamoyl.

11. Procedure for obtaining the substituted phenyluracils according to one of thetfi'ftiV-ifrlirfil "claims 1 to 10, characterized in that (a) halogen phenyluracils of the general formula (II) are reacted wherein R1, R2, R3, R4 and R5 have the meaning indicated above in one of claims 1 to 10 and X1 means halogen, with aryl compounds of the general formula (III), A. ^^^^^ X >; , wherein n, Q and X have the meaning indicated in one of claims 1 to 10, or with metal salts of the compounds of the general formula (III) -, optionally in the presence of an auxiliary agent of the reaction, and if necessary, in the presence of a diluent, or because (b) aminoalkenoic acid esters of the general formula (IV) are reacted wherein R2 and R3 have the meaning indicated above in one of claims 1 to 10 and R means alkyl, aryl or arylalkyl, with aryl isocyanates of the general formula (V) afaJI > ^ J ~. - wherein n, Q, R4, R5 and X have the meaning indicated above in one of claims 1 to 10, or with aryl urethanes (arylcarbamates) of the general formula (VI), wherein n, Q, R5, R6 and X have the meaning indicated in one of claims 1 to 10 and R means alkyl, aryl or arylalkyl, optionally in the presence of an auxiliary reaction agent and, if appropriate , in the presence of a diluent, or because (c) N-aryl-1-alkoxycarbonylamino-maleinimides of the general formula (VII) are reacted, wherein n, Q, R3, R4, R5 and X have the meaning indicated in one of claims 1 to 10, and R 'means alkyl, with metal hydroxide in the presence of water and, if appropriate, in the presence of a organic solvent, or because (d) substituted phenyluracils of the general formula (Ia) are reacted ^ -aa¿fggaiftáa-tekil Ü ^ ÉaiMÉl in which n, Q, R2, R3, R4 R5 and X have the meaning indicated in one of claims 1 to 10, with l-aminooxy-2,4-dinitro- benzene or with alkylating agents of the general formula (VIII) X2-AX (VIII) wherein A1 means optionally substituted alkyl and X2 signifies halogen or the group -O-SO2-O-A1, if appropriate in the presence of an auxiliary reaction agent, and optionally, in the presence of a diluent and, if appropriate, electrophilic or nucleophilic reactions or oxidation or reduction reactions are usually carried out in the context of the definition of the substituents.

12. Aryl isocyanates of the general formula (V) characterized in that n, Q, R4, R5 and X have the meaning indicated in one of claims 1 to 7, 9 and 10.

13. Arryl urethanes (arylcarbamates) of the general formula (VI) characterized in that n, Q, R5, R6 and X have the meaning indicated in one of claims 1 to 7 and 10 and R means alkyl, aryl or arylalkyl.

14. Aniline derivatives of the general formula (IXa) characterized because n, R 4 and X have the meaning indicated in one of claims 1 to 7 and 9 and Y means cyano, thiocarbamate or trifluoromethyl.

15. Substituted phenyluracils of the general formula (la) characterized in that n, Q, R2, R3, R4, R5 and X have the meaning indicated in one of claims 1 to 10.

16. Use of at least one substituted phenyluracil according to one of claims 1 to 10, for the fight against undesirable plants.

17. Herbicidal agents, characterized in that they have a content in at least one substituted phenyluracil according to one of claims 1 to 10. ____ át -,