Herbicidal 3-arylamino-6-trifluoromethyluracils

Abstract

There are described novel substituted 3-arylamino-6-trifluoromethyluracils of the formula I, processes for their preparation, and methods of controlling monocotyledonous and dicotyledonous harmful plants in agricultural and silvicultural crops. ##STR1## In formula I, the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are not only hydrogen, alkyl and haloalkyl, but can also have further meanings, R.sup.5 is alkyl or amino, and X is CH or N.

Description

DESCRIPTION

Herbicidal 3-arylamino-6-trifluoromethyluracils

The invention relates to novel substituted 3-arylamino-6-trifluoromethyluracils, to their preparation, and to methods of controlling monocotyledonous and dicotyledonous harmful plants in agricultural and silvicultural crops.

Uracils having herbicidal properties and their use in the control of undesirable plant growth have been disclosed in a variety of publications.

U.S. Pat. No. 4,448,961 discloses uracils, which have an arylamino radical attached to them in the 1 position, as both fungicidally and herbicidally active compounds.

U.S. Pat. No. 3,580,913 and WO 95/04461 describe 3-benzyl-6-trifluoromethyluracils having herbicidal properties, the former document disclosing uracils which are unsubstituted in the 1 position, while the second document discloses 1-methyl-substituted uracils.

However, the desired herbicidal activity of the known compounds is frequently insufficient, or else a suitably high herbicidal activity may result in undesirable damage to the agricultural or silvicultural crops.

It is an object of the present invention to provide novel substituted 3-arylamino-6-trifluoromethyluracils which do not have these disadvantages and whose biological properties are superior to the compounds known to date.

It has now been found that substituted 3-arylamino-6-trifluoromethyluracils of the formula I ##STR2## in which R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.10 -alkylcarbonyl or C.sub.1 -C.sub.10 -alkoxycarbonyl, it being possible for the two last-mentioned radicals to be optionally substituted by one or more identical or different halogen atoms,

R.sup.2 is hydrogen, halogen, nitro, amino, cyano, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halo-C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di-C.sub.1 -C.sub.4 -alkylaminocarbonyl or C.sub.1 -C.sub.4 -alkyl-sulfonyl, R.sup.3 and R.sup.4 independently of each other are hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halo-C.sub.1 -C.sub.4 alkoxy, R.sup.5 is C.sub.1 -C.sub.4 -alkyl or amino, R.sup.6 is C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl which is optionally substituted by one or more identical or different halogen atoms and X is CH or N, have a better herbicidal activity and a better crop plant tolerance in comparison with the known compounds.

Substituted 3-arylamino-6-trifluoromethyluracils of the formula I which have proved especially effective are those where

R.sup.1 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine, chlorine or bromine, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkyl, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.6 -alkyl-carbonyl or C.sub.1 -C.sub.6 -alkoxy-carbonyl, it being possible for the two last-mentioned radicals to be optionally substituted by one or more identical or different halogen atoms, R.sup.2 is hydrogen, halogen, nitro, amino, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine, chlorine or bromine, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.3 -alkoxy which is mono- or polysubstituted by fluorine, chlorine or bromine, C.sub.2 -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.3 -alkylaminocarbonyl, di-C.sub.1 -C.sub.3 -alkylaminocarbonyl or C.sub.1 -C.sub.2 -alkylsulfonyl, R.sup.3 and R.sup.4 independently of one another are hydrogen, halogen, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.3 -alkoxy which is mono- or polysubstituted by fluorine, chlorine or bromine, R.sup.5 is methyl, ethyl or amino, R.sup.6 is C.sub.1 -C.sub.4 -alkyl or C.sub.2 -C.sub.4 -alkenyl which is optionally substituted by one or more identical or different halogen atoms, and X is CH or N.

Substituted 3-arylamino-6-trifluoromethyluracils of the formula I which have proved very especially effective are those where

R.sup.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine or chlorine, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.4 -alkyl-carbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, the two last-mentioned radicals optionally being substituted by one or more identical or different halogen atoms, R.sup.2 is hydrogen, halogen, nitro, amino, cyano, C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.2 -alkyl which is mono- or polysubstituted by fluorine or chlorine, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.2 -alkoxy which is mono- or polysubstituted by fluorine or chlorine, C.sub.2 -C.sub.3 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.3 -alkoxy-carbonyl, C.sub.1 -C.sub.2 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.2 -alkylaminocarbonyl, di-C.sub.1 -C.sub.2 -alkyl-aminocarbonyl or C.sub.1 -C.sub.2 -alkylsulfonyl, R.sup.3 and R.sup.4 independently of one another are hydrogen, halogen, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, methoxy which is mono- or polysubstituted by fluorine or chlorine, R.sup.5 is methyl, ethyl or amino, R.sup.6 is C.sub.1 -C.sub.4 -alkyl or C.sub.2 -C.sub.4 -alkenyl which is optionally mono- or polysubstituted by identical or different halogen atoms from the group consisting of chlorine and fluorine, and X is CH or N.

The term "halogen" encompasses fluorine, chlorine, bromine and iodine.

The terms `alkyl`, `alkenyl` and `alkynyl` mean that the carbon chain can be branched or unbranched. The two last-mentioned terms are to be understood in such a way that the multiple bond can be in any position of the unsaturated radical in question.

The terms `halo-C.sub.1 -C.sub.4 -alkyl` and `halo-C.sub.1 -C.sub.4 -alkoxy` are to be understood as meaning that one or more hydrogen atoms of the hydrocarbon radical are replaced by identical or different halogen.

The terms di-C.sub.1 -C.sub.4 -alkylaminocarbonyl, di-C.sub.1 -C.sub.3 -alkylaminocarbonyl and di-C.sub.1 -C.sub.2 -alkylaminocarbonyl mean that the two alkyl radicals located on the nitrogen can be identical or different.

In formula I, and in the subsequent formulae II, IlI and IV, the radicals R.sup.2, R.sup.3 and R.sup.4 and the uracilylamino radical can be positioned on any carbon atom of the benzene or pyridine ring.

The present invention also relates to the 3-arylamino-6-trifluoromethyluracils of the formula II ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X have the meanings given under formula I.

These compounds of the formula II are suitable as intermediates for the preparation of the compounds of the formula I.

In the event that R.sup.5 is C.sub.1 -C.sub.4 -alkyl, the compounds of the formula I according to the invention can be prepared by reacting a compound of the formula II with an alkylating reagent in an inert solvent in the presence of a base at a suitable temperature.

In the event that R.sup.5 is amino, the compounds of the formula I according to the invention can be prepared, for example, by reacting a compound of the formula II with a nitrozation reagent and subsequently reducing the resulting N-nitrosamine, or by base-catalyzed reaction with 2,4-dinitrophenoxyamine.

Depending on the nitrosation reagent used, the nitrosation reaction can be carried out at a suitable temperature in water, dilute hydrochloric acid, dilute sulfuric acid, glacial acetic acid or in an inert solvent.

The reduction is carried out in an inert solvent at a suitable temperature.

The reaction with 2,4-dinitrophenoxyamine is carried out in inert solvents, for example in dimethylformamide using bases such as, for example, sodium hydride, sodium carbonate or potassium carbonate.

Substances which are suitable as alkylation reagents for the preparation of the compounds of the formula I according to the invention are the corresponding alkyl halides, in particular the alkyl bromides and alkyl iodides, and also dialkyl sulfates.

Substances which are suitable from amongst the group of the inert solvents are aliphatic, cycloaliphatic and aromatic hydrocarbons, each of which can optionally be chlorinated, for example hexane, ligroin, petroleum ether, cyclohexane, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethylene and chlorobenzene, ethers, for example diethyl ether, methyl ethyl ether, methyl-t-butyl ether, diisopropyl ether, dibutyl ether, 1,4-dioxane and tetrahydrofuran, ketones, for example acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, nitriles, for example acetonitrile and propionitrile, carboxylic esters, for example ethyl acetate and amyl acetate, carboxamides, for example dimethylformamide and dimethylacetamide, sulfoxides, for example dimethylsulfoxide, and sulfones, for example sulfolane.

Suitable bases are organic and inorganic bases, for example potassium carbonate, sodium carbonate, sodium hydride, potassium hydroxide, sodium hydroxide, sodium ethoxide, sodium methoxide, potassium t-butoxide, triethylamine, dimethylaminopyridine and pyridine.

The nitrosation can be carried out with customary nitrosation reagents such as alkali metal nitrites, nitrous acid or alkyl nitrites, for example t-butyl nitrite and amyl nitrite.

The subsequent reduction of the N-nitrosamines to give the compounds of the formula I according to the invention in which R.sup.5 is amino can be carried out with complex hydrides, for example lithium aluminum hydride, lithium alkoxyaluminum hydride, lithium borohydride, sodium borohydride and sodium alkoxyborohydride.

The reaction temperature is expediently selected as a function of the boiling point of the solvent and as a function of the reactivity of the reactors and is in a range from -20 to 150.degree. C., preferably between 0 and 70.degree. C.

The resulting compounds according to the invention can be isolated from the reaction mixture by customary methods, for example by distilling off the solvent employed under atmospheric or reduced pressure, by precipitation with a suitable diluent or by extraction.

If purification should be necessary, this can be effected by customary methods, for example by crystallization or by chromatographic purification processes.

The intermediates of the formula II can be prepared by reacting, in an absolute solvent, ethyl 3-amino-4,4,4-trifluoromethylcrotonate, first of all with one of the abovementioned bases and subsequently with a phenyl carbazate of the formula III, ##STR4## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X have the meanings given in the formula I.

For example, the reaction is carried out in such a manner that ethyl 3-amino-4,4,4-trifluoromethylcrotonate is introduced into absolute dimethylformamide at 0 to 5.degree. C., with sodium hydride as the base. After adding a phenyl carbazate of the formula III, the mixture is heated to 100 to 130.degree. C. The reaction mixture is hydrolyzed, acidified and extracted with an organic solvent.

Separating the intermediates of the formula II from the phenol formed during the reaction by treatment with soda solution and reliberating it by acidification has proved advantageous.

Further purification can be effected by crystallization or chromatographic purification methods.

The compounds of the formula III are either known or can be prepared by known processes from the correspondingly substituted arylhydrazines of the formula IV ##STR5## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 and X have the meanings given under the formula I, using phenyl chloroformate in the presence of one of the abovementioned bases.

The compounds of the formula IV are commercially available or can be prepared by known processes.

The compounds of the formula I according to the invention, also termed "active ingredients according to the invention" hereinbelow, have a good herbicidal activity against broad-leaved weeds and also against grasses. Due to their good crop plant tolerance, they may also be employed in a variety of agricultural crops, for example in oilseed rape, sugar beet, soybeans, cotton, rice, maize, barley, wheat and other cereal species. Individual compounds are especially suitable for use as selective herbicides in sugar beet, soybeans, cotton, maize and cereals. Equally, the compounds can be used for controlling undesirable harmful plants in perennial crops, for example afforestations, stands of ornamental trees, orchards, vineyards, citrus orchards, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit fields and hop fields.

The active ingredients according to the invention can be used for example for controlling the following genera of plants:

dicotyledonous plants from the genera: Abutilon, Amaranthus, Ambrosia, Anthemis, Brassica, Centaurea, Chenopodium, Chrysanthemum, Cirsium, Convolvulus, Datura, Galeopsis, Galinsoga, Galium, Ipomoea, Lamium, Lepidium, Matricaria, Papaver, Pharbitis, Polygonum, Portulaca, Senecio, Sinapis, Sesbania, Solanum, Sonchus, Stellaria, Urtica, Veronica, Viola and Xanthium.

Monocotyledonous plants from the genera: Alopecurus, Apera, Avena, Brachiaria, Bromus, Cyperus, Digitaria, Echinochloa, Eleocharis, Eleusine, Elymus, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Poa, Sagittaria, Setaria and Sorghum.

The active ingredients according to the invention can be employed at a rate of application of between 0.001 and 5 kg/ha, both pre- and post-emergence.

In addition, they are also used as defoliants, desiccants and haulm killers.

The active ingredients according to the invention can be applied either alone, as a mixture with each other or in combination with other active ingredients. If appropriate, other crop protection products or pesticides may be added, depending on the intended aim. If it is desired to widen the spectrum of action, other herbicidally active ingredients may also be added. Active ingredients which are suitable for this purpose are, for example, those described in `Weed Abstracts, Vol. 48, No. 2, 1994` under the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators".

Intensity and rate of action can be promoted for example by adding organic solvents, wetters and oils. Such additions may therefore permit a reduction in the dosage of the active ingredient.

The active ingredients according to the invention or their mixtures are expediently applied in the form of preparations such as powders, materials for spreading, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or diluents and, if appropriate, surfactants such as tackifying, wetting, emulsifying and/or dispersing auxiliaries.

Examples of suitable liquid carriers are aliphatic and aromatic hydrocarbons such as cyclohexane, toluene and xylene, ketones such as cyclohexanone and isophorone, other solvents such as dimethylformamide and dimethyl sulfoxide, and furthermore mineral oil fractions and vegetable oils.

Solid carriers which are suitable are minerals, for example attapulgite, bentonite, limestone, kaolin, silica gel and talc, and products of vegetable origin, for example meals.

Examples of surfactants to be mentioned are substituted benzenesulfonic acids and their salts, calcium lignosulfonate, fatty alcohol sulfates, formaldehyde condensates, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, and polyethylene alkylphenyl ethers.

The amount of active ingredient, or active ingredients, in the various products can vary within wide limits. For example, the herbicidally active compositions comprise approximately 10 to 90 percent by weight of active ingredient, approximately 90 to 10 percent by weight of liquid or solid carriers and, if appropriate, up to 20 percent by weight of surfactants.

The herbicidally active compositions can be applied in the customary manner, for example using water as the carrier, the rates of spray mixture amounting to approximately 100 to 1000 l/ha. Application of the compositions by the so-called low-volume and ultra-low-volume methods is equally possible, as is the application in the form of so-called microgranules.

The products can be prepared in a manner known per se, for example by grinding or mixing processes. If desired, products of the individual components may also be mixed only just prior to their use, as is carried out, for example, under practice conditions when using the so-called tank mix method.

To prepare the various products, for example the following components are employed:

A) wettable powder 20 percent by weight of active ingredient 35 percent by weight of attapulgite 8 percent by weight of calcium lignosulfonate 2 percent by weight of sodium N-methyl-N-oleyl-taurinate 35 percent by weight of silica gel

B) emulsion concentrate

20 percent by weight of active ingredient 75 percent by weight of isophorone 5 percent by weight of a mixture based on calcium lignosulfonate and sodium N-methyl-N-oleyltaurinate

The examples which follow illustrate the preparation of the compounds according to the invention in greater detail.

EXAMPLE 1

3-(2,3-Dichloroanilino)-1-methyl-6-trifluoromethyluracil

52.5 g (0.154 mol) of 3-(2,3-dichloroanilino)-6-trifluoromethyluracil and 42.67 g (0.309 mol) of potassium carbonate are introduced into 700 ml of acetone. 27.74 g (0.22 mol) of dimethyl sulfate are added, with stirring, at room temperature. The mixture is subsequently refluxed for one hour. After cooling, the solids are filtered off with suction, and the filtrate is concentrated in vacuo. The pale brown crystalline residue is stirred with 500 ml of diisopropyl ether and filtered off with suction. This gives 49.5 g (91% of theory) of 3-(2,3-dichloroanilino)-1-methyl-6-trifluoromethyluracil with a melting point of 179.degree. C. and a retention value of 0.49 (silica gel, hexane/ethyl acetate 1:1).

EXAMPLE 1a

3-(2,3-Dichloroanilino)-6-trifluoromethyluracil

7.5 g (0.25 mol) of sodium hydride (80% dispersion in mineral oil) are introduced into 200 ml of absolute dimethylformamide. 45.7 g (0.25 mol) of ethyl 3-amino-4,4,4-trifluoromethylcrotonate, dissolved in 100 ml of absolute dimethylformamide, are added dropwise in the course of 15 minutes at 0 to 5.degree. C., with stirring and cooling, and stirring is continued for a further 30 minutes without cooling. 63 g (0.212 mol) of phenyl 3-(2,3-dichlorophenyl)carbazate, dissolved in 500 ml of absolute dimethylformamide, are subsequently added dropwise in the course of 10 minutes. Thereupon, the mixture is stirred for 3 hours at 130.degree. C. After the reaction mixture has been left to stand overnight, it is substantially concentrated in vacuo, the residue is taken up in 2 l of water, and the mixture is washed twice using in each case 1 l of diethyl ether. The aqueous phase is brought to pH 4 to 5 using 20 ml of concentrated hydrochloric acid and extracted twice using in each case 1 l of diethyl ether. The combined diethyl ether extracts are extracted twice using in each case 250 ml of soda solution. The combined soda extracts are washed with 1 l of diethyl ether, brought to pH 4 to 5 using 70 ml of concentrated hydrochloric acid, and extracted twice using in each case 1 l of diethyl ether. The combined diethyl ether phases are dried with magnesium sulfate, filtered and evaporated fully in vacuo. The pale brown crystalline residue is stirred with 1 l of a 1:1 mixture of diisopropyl ether and hexane. After the solid has been filtered off with suction and dried, 52.9 g (73.3% of theory) of 3-(2,3-dichloroanilino)-6-trifluoro-methyluracil with a melting point of 250.degree. C. are obtained.

The compounds of the formula I according to the invention which are listed in Table 1 can be prepared analogously to Example I: ##STR6##

TABLE 1__________________________________________________________________________Ex. No. X R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 M.p. �.degree. C.!__________________________________________________________________________2 CH CH.sub.3 2-Cl 3-Cl H CH.sub.3 175.53 CH H 2-Cl 3-Cl 5-Cl NH.sub.24 CH H 2-Cl 3-Cl 5-I CH.sub.35 CH CH.sub.3 2-Cl 3-Cl 5-OCF.sub.2 H CH.sub.36 CH H 2-Cl 3-O-i-C.sub.3 H.sub.7 4-Cl CH.sub.37 CH H 2-Cl 3-OCH.sub.3 4-Cl CH.sub.38 CH H 2-Cl 3-I H CH.sub.39 CH H 2-Cl H H CH.sub.3 15910 CH H 2-Cl 3-Cl 4-I CH.sub.311 CH H 2-Cl 3-OCF.sub.3 H CH.sub.312 CH H 2-Cl 5-Cl H CH.sub.3 21813 CH H 2-Cl 4-Cl 5-Cl CH.sub.3 192.514 CH H 2-Cl 4-Cl H CH.sub.3 12415 CH H 2-Cl 3-Cl 4-Cl CH.sub.3 18316 CH H 3-Cl 4-Cl 5-Cl CH.sub.317 2-N H 3-Cl H H CH.sub.318 CH H 3-Cl 4-Cl H CH.sub.3 14319 3-N H 3-Cl 4-Cl H CH.sub.320 CH H 3-Cl 5-Cl H CH.sub.3 14821 CH H 3-Cl H H CH.sub.3 11522 CH H 4-Cl H H CH.sub.3 13723 CH H 3-Br H 5-F CH.sub.324 CH H 3-Br 4-OCF.sub.2 H H NH.sub.225 CH H 3-Br H H CH.sub.3 16126 CH CO.sub.2 C.sub.2 H.sub.5 2-I H 5-F CH.sub.327 CH H 3-I H 5-I CH.sub.328 3-N CH.sub.3 4-I H 5-Cl CH.sub.329 CH H 2-F H H CH.sub.3 13830 CH H 3-F H H CH.sub.3 12731 CH H 2-CN 3-CH.sub.3 4-CF.sub.3 CH.sub.332 3-N H 2-CN H H CH.sub.333 3-N CH.sub.3 2-CN H H CH.sub.334 2-N H 4-CN H H CH.sub.335 CH H 2-NO.sub.2 4-Cl H CH.sub.336 CH C.sub.2 H.sub.5 2-NO.sub.2 H H CH.sub.337 CH (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 2-CH.sub.3 3-I H CH.sub.338 CH H 2-C.sub.2 H.sub.5 3-Cl 5-Cl CH.sub.339 CH COCH.sub.3 2-i-C.sub.3 H.sub.7 3-F H CH.sub.340 CH H 2-CF.sub.3 H H CH.sub.3 13741 CH CHO 2-CF.sub.3 3-OCH.sub.3 H CH.sub.342 CH CH.sub.3 2-OCF.sub.2 H H H NH.sub.243 4-N H 3-OCF.sub.2 H H H CH.sub.344 4-N H 2-OCH.sub.3 H H CH.sub.345 CH H 2-O-i-C.sub.3 H.sub.7 H 5-Br NH.sub.246 CH H 2-OCH.sub.2 CH.dbd.CH.sub.2 3-F H CH.sub.347 CH CH.sub.3 2-OCH.sub.2 C.tbd.CH 3-Cl 4-Cl CH.sub.348 CH H 5-O-CH.dbd.CH.sub.3 4-Cl 3-Cl CH.sub.349 CH H 2-O(CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H 4-F CH.sub.350 CH H 5-CONHC.sub.2 H.sub.5 3-Cl H CH.sub.351 4-N CH.sub.3 2-CO-N(CH.sub.3).sub.2 H H CH.sub.352 3-N H 2-CONH.sub.2 H H CH.sub.353 CH COCH.sub.3 3-CONH.sub. 5-Cl H CH.sub.354 CH (CH.sub.2).sub.2 OCH.sub.3 3-COOH 4-Br 5-Cl CH.sub.355 2-N H 4-COOH H H CH.sub.356 CH H 5-CO.sub.2 C.sub.2 H.sub.5 3-Cl H CH.sub.357 2-N H 4-CONH-i-C.sub.3 H.sub.7 H H CH.sub.358 CH COOCH.sub.3 4-SO.sub.2 CH.sub.3 3-Cl H CH.sub.359 CH H 2-Cl 4-Cl 6-Cl CH.sub.3 116-12060 CH H 2-Cl H 6-Cl CH.sub.3 12561 CH H 2-F H 5-F CH.sub.3 147-15262 CH H H 4-CF.sub.3 H CH.sub.3 9063 CH H 2-CH.sub.3 4-Cl H CH.sub.3 144-14864 CH H 3-Cl 4-CH.sub.3 H CH.sub.3 114-11865 CH H 2-F 4-F H CH.sub.3 11066 CH H 4-CH.sub.3 H H CH.sub.3 8967 CH H 2-CH.sub.3 H H CH.sub.3 12768 CH H 2-CH.sub.3 5-CH.sub.3 H CH.sub.3 133-13669 CH H 2-CH.sub.3 3-CH.sub.3 H CH.sub.3 151-15570 CH H 2-Cl 5-CF.sub.3 H CH.sub.3 16571 CH H 3-OCH.sub.3 5-OCH.sub.3 H CH.sub.3 9372 CH H 2-F 3-Cl 4-F CH.sub.3 14873 CH H 5-CONHC.sub.2 H.sub.5 2-Cl H CH.sub.3 92-10674 CH H 5-CONH-i-C.sub.3 H.sub.7 2-Cl H CH.sub.3 111-11875 CH H 5-CO--NH-t-C.sub.4 H.sub.9 2-Cl H CH.sub.3 174-17776 CH H 2-Cl 3-CN 4-Cl CH.sub.3 195-20577 CH H 2-F 3-F H CH.sub.3 10178 CH H 2-Br 4-Br H CH.sub.3 13679 CH H 2-Br 3-F H CH.sub.3 14480 CH H 2-CN 3-F H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.40 (m.sub.c, 1H, 5'-H), 7.18 (s, 1H, NH), 6.74 (dd, 1H, 4'-H, J = 7 Hz), 6.46 (d, 1H, 6'-H, J = 7 Hz), 6.38 (s, 1H, 5-H), 3.58 (s, 3H, N--CH.sub.3).81 CH H 2-CN 3-Cl H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.35 (t, 1H, 5'-H J = 7 Hz), 7.07 (s, 1H, NH), 7.05 (d, 1H, 4'-H, J = 7 Hz), 6.54 (d, 1H, 6'-H, J = 7 Hz), 6.38 (s, 1H, 5-H), 3.58 (s, 3H, N--CH.sub.3).82 CH H 2-Br 3-F 4-Br CH.sub.3 9083 CH H 2-CN 3-CN H CH.sub.384 CH H 2-CN 3-OCH.sub.3 H CH.sub.385 CH H 2-Br 3-Br H CH.sub.386 CH H 2-Br 3-Br 4-Br CH.sub.387 CH H 2-Br 3-Cl H CH.sub.388 CH H 2-Br 3-Cl 4-Br CH.sub.389 CH H 3-Br 4-Br H CH.sub.390 CH H 2-F 3-F 4-F CH.sub.391 CH H 4-F H H CH.sub.3 12492 CH H 4-F H H CH.sub.3 11093 CH H 2-NO.sub.2 4-NO.sub.2 H CH.sub.3 199-20394 CH H 2-NO.sub.2 4-CF.sub.3 H CH.sub.3 142-14595 CH H 2-NO.sub.2 4-CF.sub.3 6-NO.sub.2 CH.sub.3 21196 CH H 2-Cl 4-NO.sub.2 6-Cl CH.sub.3 50-5597 CH H 2-Cl 4-NO.sub.2 5-CF.sub.3 CH.sub.3 162-16898 CH H 2-Cl 3-Cl 4-Br CH.sub.3 17499 CH H 2-Cl 3-Cl 4-NO.sub.2 CH.sub.3 188100 CH H 2-NO.sub.2 4-NO.sub.2 H CH.sub.3 108101 CH H 4-NO.sub.2 H H CH.sub.3 128-132102 CH H 2-Cl 4-Cl 6-Cl NH.sub.2 175103 CH H 2-Cl 6-Cl H NH.sub.2 153104 CH H 2-F 4-F H NH.sub.2 138105 CH H 2-F 5-F H NH.sub.2 155106 CH H 4-CF.sub.3 H H NH.sub.2 68107 CH H 2-Cl 5-CF.sub.3 H NH.sub.2 170108 CH H 2-F 3-Cl 4-F NH.sub.2 50109 CH H 3-OCH.sub.3 5-OCH.sub.3 H NH.sub.2 181110 CH H 2-CH.sub.3 H H NH.sub.2 160111 CH H 4-CH.sub.3 H H NH.sub.2 150112 CH H 2-CH.sub.3 3-CH.sub.3 H NH.sub.2 212113 CH H 2-CH.sub.3 5-CH.sub.3 H NH.sub.2 217-221114 CH H 2-CH.sub.3 4-Cl H NH.sub.2 198115 CH H 2-Cl 3-CN 4-Cl NH.sub.2 81-86116 CH H 5-CONHC.sub.2 H.sub.5 2-Cl H NH.sub.2 229117 CH H 5-CONH-i-C.sub.3 H.sub.7 2-Cl H NH.sub.2 96-102118 CH H 5-CONH-t-C.sub.4 H.sub.9 2-Cl H NH.sub.2 112119 CH H H H H NH.sub.2 155-159120 CH H 2-NO.sub.2 4-NO.sub.2 H NH.sub.2 220121 CH H 3-Cl 4-CH.sub.3 H NH.sub.2 200 Mhz-.sup.1 H NMR (D.sub.6 -DMSO): .delta. = 8.72 (s, 1H, NH), 7.12 (d, 1H, 5'-H, J = 8 Hz), 6.79 (d, 1H, 2'-H, J = 2 Hz), 6.61 (dd, 1H, 6'-H, J = 2 Hz, J = 8 Hz), 6.31 (s, 1H, 5-H), 5.52 (s, 2H, NH.sub.2), 2.20 (s, 3H, CH.sub.3).122 CH H 2-F 3-F H NH.sub.2 127123 CH H 2-Br 4-Br H NH.sub.2 185124 CH H 2-Br 3-F H NH.sub.2125 CH H 2-CN 3-F H NH.sub.2126 CH H 2-CN 3-Cl H NH.sub.2127 CH H 2-Br 3-F 4-Br NH.sub.2128 CH H 2-CN 3-CN H NH.sub.2129 CH H 2-CN 3-OCH.sub.3 H NH.sub.2130 CH H 2-Br 3-Br H NH.sub.2131 CH H 2-Br 3-Br 4-Br NH.sub.2132 CH H 2-Br 3-Cl H NH.sub.2133 CH H 2-Br 3-Cl 4-Br NH.sub.2134 CH H 3-Br 4-Br H NH.sub.2135 CH H 2-F 3-F 4-F NH.sub.2 --136 CH H 4-F H H NH.sub.2 --137 CH CH.sub.3 2-Cl 3-Cl H NH.sub.2 160-163138 CH CH.sub.3 2-F 5-F H NH.sub.2 181139 CH CH.sub.3 2-F 3-Cl 4-F CH.sub.3 155140 CH CH.sub.3 2-Cl 3-Cl 4-Br CH.sub.3 168141 CH CH.sub.3 2-Cl 3-Cl 4-NO.sub.2 CH.sub.3 188142 CH CH.sub.3 2-Br 4-Br H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.61 (d, 1H, 3'-H, J = 1 Hz), 7.43 (dd, 1H, 5'-H, J = 7 Hz, J = 1 Hz), 7.18 (d, 1H, 6'-H, J = 7 Hz), 6.25 (s, 1H, 5-H), 3.48 (s, 3H, N--CH.sub.3), 3.30 (s, 3H, N--CH.sub.3).143 CH H 2-Cl 4-Cl 6-Cl C.sub.2 H.sub.5 108144 CH H 2-Cl 3-Cl H C.sub.2 H.sub.5 138145 CH H 2-Cl 3-Cl H i-C.sub.3 H.sub.7 200 Mhz-.sup.1 H NMR (D.sub.6 -DMSO): .delta. = 8.63 (s, 1H, NH), 7.20-7.04 (m, 2H, 4'-H, 5'-H), 6.80 (s, 1H, 5-H), 6.58 (dd, 1H, 6'-H, J = 2 Hz, J = 8 Hz), 5.26 (sept., 1H, CH, J = 7 Hz), 1.24 (d, 6H, 2x CH.sub.3, J = 7 Hz).146 CH H 2-Cl 3-Cl H n-C.sub.3 H.sub.7 150147 CH H 2-Cl 3-Cl H n-C.sub.4 H.sub.9 95-100148 CH COCH.sub.3 4-CF.sub.3 H H CH.sub.3 125149 CH COCH.sub.3 2-Cl 3-Cl H CH.sub.3 195150 CH COC.sub.2 H.sub.5 2-Cl 3-Cl H CH.sub.3 62151 CH CO-i-C.sub.3 H.sub.7 2-Cl 3-Cl H CH.sub.3 72-76152 CH CO-cyclo-C.sub.3 H.sub.5 2-Cl 3-Cl H CH.sub.3 90153 CH COCH.sub.3 2-CH.sub.3 3-CH.sub.3 H CH.sub.3 300 Mhz-.sup.1 H (D.sub.6 -DMSO): .delta. = 7.44- 7.02 (m, 3H, 4'-H, 5'-H, 6'-H), 6.61 (6.46)* (s, 1H, 5-H), 3.30 (s, 3H, N--CH.sub.3), 2.42*-1.90* (6x s, 9H, 3x CH.sub.3). *: double signal set due to E/Z-amide isomerism154 CH COCH.sub.3 3-OCH.sub.3 5-OCH.sub.3 H CH.sub.3 110-113155 CH COCH.sub.3 2-Cl 6-Cl H CH.sub.3 70156 CH COCH.sub.3 2-Cl 4-Cl 6-Cl CH.sub.3 67157 CH COCH.sub.3 2-F 5-F H CH.sub.3 158158 CH COCH.sub.3 2-F 4-F H CH.sub.3 51-54159 CH COCH.sub.3 2-F 3-Cl 4-F CH.sub.3 52160 CH COCH.sub.3 2-Cl 5-CF.sub.3 H CH.sub.3 50161 CH COCH.sub.3 2-CH.sub.3 4-Cl H CH.sub.3 300 Mhz-.sup.1 H NMR (D.sub.6 -DMSO): .delta. = 7.6- 7.0 (m, 3H, 3'-H, 5'-H, 6'-H), 6.61 (s, 1H, 5-H), 3.40 (s, 3H, N--CH.sub.3), 2.38*- 1.94* (4x s, 6H, 2x CH.sub.3). *: double signal set due to E/Z-amide isomerism162 CH COCH.sub.3 5-CONHC.sub.2 H.sub.5 2-Cl H CH.sub.3 200 Mhz-.sup.1 H (D.sub.6 -DMSO): .delta. = 8.70- 7.57 (m, 4H, NH, 3'-H, 4'-H, 6'-H), 6.67 (s, 1H, 5-H), 4.02 (q, 2H, CH.sub.2, J = 7 Hz), 3.40 (s, 3H, N--CH.sub.3), 2.04 (1.99)* (s, 3H, COCH.sub.3), 1.18 (t, 3H, CH.sub.3, J = 7 Hz). *: double signal set due to E/Z-amide isomerism163 CH COCH.sub.3 5-CONH-i-C.sub.3 H.sub.7 2-Cl H CH.sub.3 200 Mhz-.sup.1 H NMR (D.sub.6 -DMSO): .delta. = 8.63- 7.58 (m, 4H, NH, 3'-H, 4'-H, 6'-H), 6.68 (s, 1H, 5-H), 4.02 (m.sub.c, 1H, CH), 3.32 (s, 3H, N--CH.sub.3), 2.02 (s, 3H, COCH.sub.3), 1.2-1.0 (m, 6H, 2x CH.sub.3).164 CH COCH.sub.3 5-CONH-t-C.sub.4 H.sub.9 2-Cl H CH.sub.3 200 Mhz-.sup.1 H NMR (D.sub.6 -DMSO): .delta. = 8.24- 7.28 (m, 4H, NH, 3'-H, 4'-H, 6'-H), 6.70 (s, 1H, 5-H), 3.30 (s, 3H, N--CH.sub.3), 2.05 (s, 3H, COCH.sub.3), 1.38 (1.36)* (s, 9H, C(CH.sub.3).sub.3). *: double signal set due to E/Z-amide isomerism165 CH CO-i-C.sub.3 H.sub.7 2-Br 4-Br H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.87 (d, 1H, 3'-H, J = 0.5 Hz), 7.4-7.6 (br m, 2H, 5'-H, 6'-H), 6.30 (6.22)* (s, 1H, 5-H), 3.49 (3.53)* (s, 3H, N--CH.sub.3), 2.65 (sept., 1H, COCH, J = 6 Hz), 1.13 (d, 3H, CH.sub.3, J = 6 Hz), 1.07 (d, 3H, CH.sub.3, J = 6 Hz). *: double signal set due to E/Z-amide isomerism166 CH CO-cyclo-C.sub.3 H.sub.5 2-Br 4-Br H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.90 d, 1H, 3'-H, J = 0.5 Hz), 7.4-7.8 (br m, 2H, 5'-H, 6'-H), 6.32 (6.24) (s, 1H, 5-H), 3.50 (3.54) (s, 3H, N--CH.sub.3), 09.-1.6 (br m, 5H, cyclopropyl-H). *: double signal set due to E/Z-amide isomerism167 CH COCF.sub.3 2-Cl 3-Cl H CH.sub.3 135168 CH COCClF.sub.2 2-Cl 3-Cl H CH.sub.3169 CH COCCl.sub.3 2-Cl 3-Cl H CH.sub.3170 CH COCBr.sub.3 2-Cl 3-Cl H CH.sub.3171 CH COC.sub.2 F.sub.5 2-Cl 3-Cl H CH.sub.3172 CH CO-n-C.sub.3 F.sub.7 2-Cl 3-Cl H CH.sub.3173 CH CO-n-C.sub.4 F.sub.9 2-Cl 3-Cl H CH.sub.3174 CH COCF.sub.3 2-Br 4-Br H CH.sub.3 49175 CH COCF.sub.3 2-Br 3-F H CH.sub.3176 CH COCF.sub.3 2-Br 3-F 4-Br CH.sub.3177 CH COCF.sub.3 2-Cl 3-Cl 4-Cl CH.sub.3178 CH COCF.sub.3 2-Cl 3-Cl 4-Br CH.sub.3179 CH COCF.sub.3 2-Cl 3-Cl 4-NO.sub.2 CH.sub.3180 CH COCF.sub.3 2-Cl 3-CN 4-Cl CH.sub.3181 CH COCF.sub.3 2-F 3-F H CH.sub.3182 CH COCF.sub.3 2-CN 3-Cl H CH.sub.3183 CH SO.sub.2 CH.sub.3 2-Cl 3-Cl H CH.sub.3 121184 CH SO.sub.2 C.sub.2 H.sub.5 2-Cl 3-Cl H CH.sub.3 157185 CH SO.sub.2 CH.sub.2 Cl 2-Cl 3-Cl H CH.sub.3 62-66186 CH SO.sub.2 CH.dbd.CH.sub.2 2-Cl 3-Cl H CH.sub.3 120187 CH SO.sub.2 CH.sub.3 2-Br 4-Br H CH.sub.3 300 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 8.26 (d, 1H, 6'-H, J = 8 Hz), 7.83 (d, 1H, 3'-H, J = 1 Hz), 7.52 (dd, 1H, 5'-H, J = 1 Hz, J = 8 Hz), 6.26 (s, 1H, 5-H), 3.51 (s, 3H, N--CH.sub.3), 3.40 (s, 3H, SO.sub.2 --CH.sub.3).188 2-N H 4-NO.sub.2 H H CH.sub.3 163-166189 2-N H 4-CF.sub.3 H H CH.sub.3 200 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 8.42 (d, 1H, 6'-H, J = 1 Hz), 8.18 (s, 1H, NH), 7.70 (dd, 1H, 4'-H, J = 1 Hz, J = 8 Hz), 6.75 (d, 1H, 3'-H, J = 8 Hz), 6.40 (s, 1H, 5-H), 3.58 (s, 3H, N--CH.sub.3).190 2-N H 3-F H H CH.sub.3 139-143191 2-N H 3-Cl H H CH.sub.3 200 Mhz-.sup.1 H NMR (CDCl.sub.3): .delta. = 7.50 (t, 1H, 4'-H, J = 7 Hz), 7.26 (s, 1H, NH), 6.90 (d, 1H, 5'-H, J = 7 Hz), 6.59 (d, 1H, 3'-H, J = 7 Hz), 6.39 (s, 1H, 5-H), 3.58 (s, 3H, N--CH.sub.3).192 2-N CO--CF.sub.3 3-Cl H H CH.sub.3193 2-N H 3-Cl H H NH.sub.2194 3-N H 2-Cl H H CH.sub.3195 3-N H 2-Cl 4-Cl H CH.sub.3196 3-N H 4-Cl H H CH.sub.3197 3-N H 4-Cl H H NH.sub.2198 3-N COCF.sub.3 2-Cl 4-Cl H CH.sub.3199 4-N H 2-Cl 3-Cl H CH.sub.3200 4-N H 2-F 3-F H CH.sub.3__________________________________________________________________________

The compounds of the formula II listed in Table 2 can be prepared analogously to Example 1a: ##STR7##

TABLE 2__________________________________________________________________________Ex. No. X R.sup.1 R.sup.2 R.sup.3 R.sup.4 M.p. �.degree. C.!__________________________________________________________________________ 2a CH CH.sub.3 2-Cl 3-Cl H 203 3a CH H 2-Cl 3-Cl 5-Cl 4a CH H 2-Cl 3-Cl 5-I 5a CH CH.sub.3 2-Cl 3-Cl 5-OCF.sub.2 H 6a CH H 2-Cl 3-O-i-C.sub.3 H.sub.7 4-Cl 7a CH H 2-Cl 3-OCH.sub.3 4-Cl 8a CH H 2-Cl 3-I H 9a CH H 2-Cl H H 21710a CH H 2-Cl 3-Cl 4-I11a CH H 2-Cl 3-OCF.sub.3 H12a CH H 2-Cl 5-Cl H 224-22513a CH H 2-Cl 4-Cl 5-Cl 28014a CH H 2-Cl 4-Cl H 248-25015a CH H 2-Cl 3-Cl 4-Cl 23816a CH H 3-Cl 4-Cl 5-Cl17a 2-N H 3-Cl H H18a CH H 3-Cl 4-Cl H 18819a 3-N H 3-Cl 4-Cl H20a CH H 3-Cl 5-Cl H 25521a CH H 3-Cl H H 23522a CH H 4-Cl H H 190-19123a CH H 3-Br H 5-F24a CH H 3-Br 4-OCF.sub.2 H H25a CH H 3-Br H H 22726a CH CO.sub.2 C.sub.2 H.sub.5 2-I H 5-F27a CH H 3-I H 5-I28a 3-N CH.sub.3 4-I H 5-Cl29a CH H 2-F H H 22030a CH H 3-F H H 20531a CH H 2-CN 3-CH.sub.3 4-CF.sub.332a 3-N H 2-CN H H33a 3-N CH.sub.3 2-CN H H34a 2-N H 4-CN H H35a CH H 2-NO.sub.2 4-Cl H36a CH C.sub.2 H.sub.5 2-NO.sub.2 H H37a CH (CH.sub.2).sub.2 CO.sub.2 CH.sub.3 2-CH.sub.3 3-I H38a CH H 2-C.sub.2 H.sub.5 3-Cl 5-Cl39a CH COCH.sub.3 2-i-C.sub.3 H.sub.7 3-F H40a CH H 2-CF.sub.3 H H 180-18241a CH CHO 2-CF.sub.3 3-OCH.sub.3 H42a CH CH.sub.3 2-OCF.sub.2 H H H43a 4-N H 3-OCF.sub.2 H H H44a 4-N H 2-OCH.sub.3 H H45a CH H 2-O-i-C.sub.3 H.sub.7 H 5-Br46a CH H 2-OCH.sub.2 CH.dbd.CH.sub.2 3-F H47a CH CH.sub.3 2-OCH.sub.2 C.tbd.CH 3-Cl 4-Cl48a CH H 5-OCH.dbd.CH.sub.2 4-Cl 3-Cl49a CH H 2-O-(CH.sub.2).sub.2 CO.sub.2 CH.sub.3 H 4-F50a CH H 5-CONHC.sub.2 H.sub.5 3-Cl H51a 4-N CH.sub.3 2-CON(CH.sub.3).sub.2 H H52a 3-N H 2-CONH.sub.2 H H53a CH COCH.sub.3 3-CONH.sub.2 5-Cl H54a CH (CH.sub.2).sub.2 OCH.sub.3 3-COOH 4-Br 5-Cl55a 2-N H 4-COOH H H56a CH H 5-CO.sub.2 C.sub.2 H.sub.5 3-Cl H57a 2-N H 4-CONH-i-C.sub.3 H.sub.7 H H58a CH CO.sub.2 CH.sub.3 4-SO.sub.2 CH.sub.3 3-Cl H59a CH H 2-Cl 4-Cl 6-Cl 217-22060a CH H 2-Cl H 6-Cl 21161a CH H 2-F H 5-F 148-15562a CH H H 4-CF.sub.3 H 19963a CH H 2-CH.sub.3 4-Cl H 222-22664a CH H 3-Cl 4-CH.sub.3 H 148-15165a CH H 2-F 4-F H 187-19266a CH H 4-CH.sub.3 H H 22667a CH H 2-CH.sub.3 H H 21068a CH H 2-CH.sub.3 5-CH.sub.3 H 24669a CH H 2-CH.sub.3 3-CH.sub.3 H 13270a CH H 2-Cl 5-CF.sub.3 H 18871a CH H 3-OCH.sub.3 5-OCH.sub.3 H 18772a CH H 2-F 3-Cl 4-F 19373a CH H 5-CONHC.sub.2 H.sub.5 2-Cl H 29474a CH H 5-CONH-i-C.sub.3 H.sub.7 2-Cl H 25075a CH H 5-CONH-t-C.sub.4 H.sub.9 2-Cl H 17076a CH H 2-Cl 3-CN 4-Cl 226-23177a CH H 2-F 3-F H 156-16178a CH H 2-Br 4-Br H 26179a CH H 2-Br 3-F H 24980 3-N H 4-Cl H H__________________________________________________________________________

In Tables 1 and 2, the position indicated for R.sup.1, R.sup.2, R.sup.3, R.sup.4 and, in the event of X equals N, also the position indicated for N, is to be understood as meaning such that the reference position 1 is attributed to the carbon atom in the benzene or pyridine ring on which linkage with the uracilylamino group takes place. The position of substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4 and of N is then determined in accordance with the general numeration of known nomenclature rules.

The following comparison examples illustrate the possible uses of the compounds according to the invention.

In these examples, the abbreviations used denote:

Harmful Plants

______________________________________ABUTH Abutilon theophrasti PHBPU Pharbitis purpureaAGRRE Elymus repens POLPE Polygonum sp.ALOMY Alopecurus myosuroides SETVI Setaria viridisGALAP Galium aparine SORHA Sorghum halepenseMATCH Matricaria chamomilla VERPE Veronica persicaPANSS Panicum sp.______________________________________

Crop Plant

______________________________________ZEAMX Zea mays______________________________________ 0=no damage 1=1-24% damage 2=25-74% damage 3=75-89% damage 4=90-100% damage

Use Example A

In the greenhouse, the plant species listed are treated post-emergence with the compound according to the invention at a rate of application of 0.03 kg of active ingredient/ha. To this end, the compound is sprayed uniformly over the plants in the form of an emulsion with 500 l of water/ha. After 2 weeks, it shows a very good activity against the harmful plants and better activity than the agent disclosed in WO 95/04461 and tested under the same conditions for the purpose of comparison.

__________________________________________________________________________Test compounds ALOMY AGRRE SETVI PANSS SORHA ABUTH GALAP MATCH POLPE VERPE__________________________________________________________________________1 3 2 3 4 3 4 3 4 4 42 2 1 2 3 2 4 3 3 4 3Untreated 0 0 0 0 0 0 0 0 0 0__________________________________________________________________________

Use Example B

In the greenhouse, the plant species listed are treated pre-emergence with the compound according to the invention at a rate of application of 0.3 kg of active ingredient/ha. To this end, the compound is sprayed uniformly onto the soil which contains the seeds of the test plants in the form of an emulsion with 500 l of water/ha. 2 weeks after the treatment, it shows a very good activity against the harmful plants and a markedly better tolerance by maize than the agent disclosed in WO 95/04461 and tested under the same conditions for the purpose of comparison.

__________________________________________________________________________Test compounds ZEAMX AGRRE PHBPU POLPE__________________________________________________________________________3 0 4 4 44 3 4 4 4Untreated 0 0 0 0__________________________________________________________________________

Claims

1. A substituted 3-arylamino-6-trifluoromethyluracil of the formula I ##STR10## in which R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.10 -alkylcarbonyl or C.sub.1 -C.sub.10 -alkoxycarbonyl, it being possible for the two last-mentioned radicals to be optionally substituted by one or more identical or different halogen atoms,

R.sup.2 is hydrogen, halogen, nitro, amino, cyano, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halo-C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl-C.sub.1 -C.sub.4 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyl, di-C.sub.1 -C.sub.4 -alkylaminocarbonyl or C.sub.1 -C.sub.4 -alkyl-sulfonyl,

R.sup.3 and R.sup.4 independently of each other are hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halo-C.sub.1 -C.sub.4 -alkoxy,

R.sup.5 is C.sub.1 -C.sub.4 -alkyl or amino,

R.sup.6 is C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl which is optionally substituted by one or more identical or different halogen atoms and

X is CH or N.

2. A substituted 3-arylamino-6-trifluoromethyluracil of the formula I as claimed in claim 1, wherein

R.sup.1 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine, chlorine or bromine, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkyl, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.6 -alkylcarbonyl or C.sub.1 -C.sub.6 -alkoxycarbonyl, it being possible for the two last-mentioned radicals to be optionally substituted by one or more identical or different halogen atoms,

R.sup.2 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine, chlorine or bromine, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.3 -alkoxy which is mono- or polysubstituted by fluorine, chlorine or bromine, C.sub.2 -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.3 -alkoxy-carbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.3 -alkylaminocarbonyl, di-C.sub.1 -C.sub.3 -alkylaminocarbonyl or C.sub.1 -C.sub.2 -alkylsulfonyl,

R.sup.3 and R.sup.4 independently of one another are hydrogen, halogen, nitro, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.3 -alkoxy which is mono- or polysubstituted by fluorine, chlorine or bromine,

R.sup.5 is methyl, ethyl or amino,

R.sup.6 is C.sub.1 -C.sub.4 -alkyl or C.sub.2 -C.sub.4 -alkenyl which is optionally substituted by one or more identical or different halogen atoms, and

X is CH or N.

3. A substituted 3-arylamino-6-trifluoromethyluracil of the formula I as claimed in claim 1, wherein

R.sup.1 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl which is mono- or polysubstituted by fluorine or chlorine, formyl, SO.sub.2 R.sup.6, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, the two last-mentioned radicals optionally being substituted by one or more identical or different halogen atoms,

R.sup.2 is hydrogen, halogen, nitro, amino, cyano, C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.2 -alkyl which is mono- or polysubstituted by fluorine or chlorine, methoxy, ethoxy, propoxy, isopropoxy, C.sub.1 -C.sub.2 -alkoxy which is mono- or polysubstituted by fluorine or chlorine, C.sub.2 -C.sub.3 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.2 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkoxy, carboxyl, aminocarbonyl, C.sub.1 -C.sub.2 -alkylaminocarbonyl, di-C.sub.1 -C.sub.2 -alkyl-aminocarbonyl or C.sub.1 -C.sub.2 -alkylsulfonyl,

R.sup.3 and R.sup.4 independently of one another are hydrogen, halogen, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, methoxy which is mono- or polysubstituted by fluorine or chlorine,

R.sup.5 is methyl, ethyl or amino,

R.sup.6 is C.sub.1 -C.sub.4 -alkyl or C.sub.2 -C.sub.4 -alkenyl which is optionally mono- or polysubstituted by identical or different halogen atoms from the group consisting of chlorine and fluorine, and

X is CH or N.

4. A substituted 3-arylamino-6-trifluoromethyluracil of the formula II ##STR11## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X have the meanings given under formula I as intermediates for the preparation of a compound of the formula I as claimed in claim 1.

5. A process for the preparation of a compound of the formula I as claimed in claim 1, which comprises, in the event that R.sup.5 in formula I is C.sub.1 -C.sub.4 -alkyl,

A) reacting a compound of the formula II as claimed in claim 4 with an alkylating reagent or,

in the event that R.sup.5 in formula I is amino,

B) reacting a compound of the formula II as claimed in claim 4, first of all, with a nitrosation reagent and then reacting the resulting N-nitrosamine with a complex hydride, or reacting a compound of the formula II as claimed in claim 4 with 2,4-dinitrophenoxyamine with base catalysis.

6. A process for the preparation of a compound of the formula II as claimed in claim 4, which comprises introducing ethyl 3-amino-4,4,4-trifluoromethyl-crotonate together with a base into an inert solvent and subsequently reacting it with a compound of the formula Ill ##STR12## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X have the meanings given under formula I as set forth in claim 1.

7. A herbicidally active composition, which comprises at least one compound as claimed in claim 1.

8. A herbicidally active composition as claimed in claim 7 in the form of a mixture with carriers and/or surfactants.

9. A method of controlling monocotyledonous and dicotyledonous harmful plants in agricultural and silvicultural crops, which comprises applying at least one of the compounds as claimed in claim 1 to the location of the undesirable plant growth.

10. The method as claimed in claim 9, wherein the compounds are employed in the form of a mixture with carriers and/or surfactants.