IL45635A - 3-(trifluoromethylcyclohexyl)-uracils,their production and herbicidal compositions containing them - Google Patents

Abstract

1474704 Trifluoromethylcyclohexyl uracils BASF AG 11 Oct 1974 [13 Oct 1973] 44083/74 Heading C2C Trifluoromethylcyclohexyl uracils of the general formula wherein R 1 is halogen; R<SP>2</SP> is C 1-3 alkyl or R<SP>1</SP> and R<SP>2</SP> together denote -(CH 2 ) n - in which n is 3, 4 or 5 and R<SP>3</SP> is H or acyl of up to 8C atoms, are prepared by reacting a trifluoromethyl cyclohexyl urea with a #-keto ester of formula or by reacting a trifluoromethylcyclohexyl isocyanate with a #-amino-ester of formula to give, in either case, a compound of formula and cyclizing the product in the presence of a base the said product or corresponding halocompound in which H has been replaced by halogen as R<SP>1</SP>. Amongst the examples the compounds 3 - (3 - trifluoromethyl) cyclohexyl- 5-bromo-6-methyl uracil and the 5,6-trimethyl lene derivative are prepared. Herbicidal compositions comprise as active ingredient a uracil of Formula I together with a solid or liquid carrier and optionally with an emulsifying, wetting or dispersing agent, a fertilizer, fungicide, nematocide, insecticide, antidote and/or plant growth regulator. [GB1474704A]

Description

3-(Trifluoromethylcyclohexyl)-uracile, their production and herbicidal compositions containing them BASF Aktiengesellschaft C. 43662 The present invention relates to new and valuable uracils having a good erbicidal action, herbicides containing these compounds, and a process for controlling the growth of unwanted plants with these compounds.

It is known (Israel Patent Specification No. 14261) to use substituted uracils, e.g. 3-cyclohexyl-5»6-trimethylene uracil, as herbicides. However, their action - particularly their compatibility with crop plants - is poor.

We have now found that 3-( trifluoromethylcyclohexyl)-uracils of the formula where R denotes halogen (chloro or bromo), R denotes alk l ■5 of 1 to 3 carbon atoms - preferably methyl and Br denotes 1 2 hydrogen and R may be linked to R by a methylene chain of the formula -(CH )_-, have an excellent herbicidal action. - la - o.z. 30,1 3 The new compounds have, compared with prior art active ingredients, a much better crop plant compatibility combined^ with the same, or superior, herbicidal action.

The compounds may be prepared by condensing mono-substituted ureas with β-keto esters with the elimination of water to 3- (3' -substituted ureido)-2,3-unsaturated esters and cyclizing the latter by adding a base. The 3- (3' -substituted ureido)-2,3-unsaturated esters may also be obtained by adding substituted cyclohexyl isocyanates to 3-amino-2,3-unsaturated esters. The halogen radical may be subsequently introduced by known methods.

The mono- substituted ureas which are novel may be prepared by the following route: known trifluoromethylaniline are hydrogenated to give correspondingly substituted cyclo-hexylamines. These are then reacted by known methods with phosgene to form isocyanates, which yield the desired ureas upon reaction with ammonia.

The following reaction scheme and examples demonstrate the preparation ofe the compounds of the invention: H EXAMPLE 1 3-trifluorometh,ylcyclohex.yl-5-bromo-6-meth.yl uracil 3- (trifluoromethyl)-cyclohexylurea 99 parts of 3-trifluoromethylcyclohexylamine is dissolved in 250 parts of toluene. While cooling with ice, a weak stream of dry hydrogen chloride is introduced into the solution for 15 minutes. A fairly strong stream of phosgene is subsequently passed into the suspension which has formed and the reaction temperature simultaneously raised to 110° to 120°C and kept at this temperature until the reaction solution is clear again. Excess phosgene is removed with a strong nitrogen stream and the remaining solution is fractionally distilled. There is thus obtained 79 parts of isocyanate, which is dissolved in benzene. While cooling, a dry NH-j stream is gassed in. Upon concentration of the opaque reaction solution to ^ of its original volume j5-(trifluoro-methyl)-cyclohexylurea crystallizes out and is filtered off and dried.

Melting point: 117° to 119°C. 3- (3-trifluoromethyl)-cyclohexyl-6-meth l uracil 20 parts of dried J-trifluoromethylcyclohexylurea is, together with 126 parts of acetoacetic ester and 85Ο parts of toluene, heated under reflux in a water separator until 15 parts of water has been removed. The reaction solution is concentrated, a yellow oil being obtained as residue. This Ο.Ζ. 30,143 yellow oil is dissolved In 250 parts of absolute methanol and boiled under reflux for 10 minutes with 52 parts of sodium methylate. This reaction solution is introduced into 500 parts of IN HCl, the desired product crystallizing out. After filtration and drying, 3- (3-trifluoromethyl)-cyclohexyl-6-methyl uracil is obtained.

Melting point: 191° to 193°C 3- (3-tri luoromethyl)-cyclohexyl-5~bromo-6-methyl uracil 207 parts of 3- (3-trifluoromethyl)-cyclohexyl-6-methyl uracil is dissolved in 900 parts of glacial acetic acid. At room temperature 100 parts of bromine is dripped in. Upon completion of the reaction, the reaction mixture is poured into water and the 3- (3-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil isolated therefrom by filtration.

Melting point: 125° to 127°C. One of the two isomers having a melting point of 205° to 206°C may be separated by recrystallization.

EXAMPLE ^ 3- (3-trifluoromethyl)~cyclohexyl-^, 6-trimethylene uracil 46.8 parts of ethyl cyclopentanone-2-carboxylate, together with 63 parts of 3-trifluoromethylcyclohexylurea, 120 parts of dioxane and 120 parts of benzene, is heated under reflux in a water separator until 4.3 parts of water has been removed. When this reaction solution is concentrated a yellow oil is obtained. This oil is boiled under reflux for 10 minutes with 23.2 parts of sodium methylate and 200 parts of absolute methanol. When this solution is poured into 250 parts of IN HCl the desired product crystallizes out and is filtered and dried.

O.Z. 50,1 ^ Melting point: I960 to 198°C.

The following ureas and uracils, for instance, are .^N obtained in the same way: 2-trifluoromethylcyclohexylurea, m.p. 191° to 193°C 4-trifluoromethylcyclohexylurea 3- ( 2-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil, m.p. 200°C 3- (4-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil 3- (2-trifluoromethyl)-cyclohexyl-5, 6~trimethylene uracil, m.p. 230° to 2 1°C 3- ( - 1rifluorome h 1) -eyelohexyl- 5 , 6- 1rimethylene uracil.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine distribution of the active ingredient.

For the preparation of solutions, emulsions, -pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaph-thalene, alkylated naphthalenes and their derivatives suoh as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, ehlor©benzene, isophorone, etc, and strongly polar solvents suoh as dimethyl- o.z. 30,1 3 formamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable. __^\ Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, poly-oxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol, and ethoxylated nonylphenol, alkyl-phenol polyglycol ethers, tributylphenyl ;polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, o.z. 30,1 3 lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers^ such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95* and preferably 0.5 to 90, % by weight of active ingredient.

There may be added to the compositions or individual active ingredients (if desired, immediately before use (tank-mix) ) oils of various types, herbicides, fungicides, nemato-cides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g., silicones), growth regulators, antidotes and other herbicidally effective compounds such as substituted anilines substituted aryloxycarboxylic acids and salts, esters and amides thereof, substituted ethers substituted arsonic acids and their salts, esters and amides O.Z. 30,1 substituted benzimidazoles substituted benzisothiazoles substituted benzothiadiazinone dioxides substituted benzoxazines substituted benzoxazinones substituted benzothiadiazoles substituted biurets substituted quinolines substituted carbamates substituted aliphatic carboxylic acids and their salts, esters and amides substituted aromatic carboxylic acids and their salts, esters and amides substituted carbamoylalkylthiol- or -dithiophosphates substituted quinazolines substituted cycloalkylamidocarbothlolic acids and their salts, esters and amides substituted cycloalkylcarbonamidothiazoles substituted dicarboxylic acids and their salts, esters and amides substituted dihydrobenzofuranyl sulfonates substituted disulfides substituted dipyridylium salts substituted dithiocarbamates substituted dithiophosphoric acids and their salts, esters and amides substituted ureas substituted hexahydro-lH-carbothioates substituted hydantoins O.Z. _30,l 3 substituted hydrazides substituted hydrazonium salts substituted isoxazole pyriraidones substituted imidazoles substituted isothiazole pyrimidones substituted ketones substituted naphthoquinones substituted aliphatic nitriles substituted aromatic nitriles substituted oxadiazoles substituted oxadiazinones substituted oxadiazolidine diones substituted oxadiazine diones substituted phenols and their salts and esters substituted phosphonic acids and their salts, esters and amides substituted phosphonium chlorides substituted phosphonalkyl glycines substituted phosphites substituted phosphoric acids and their salts, esters and amides substituted piperidines substituted pyrazoles substituted pyrazole alkylcarboxylic acids and their salts,; esters and amides substituted pyrazolium salts substituted pyrazolium alkyl sulfates substituted pyridazines substituted pyridazones O.Z. 30,1 3 substituted pyridine carboxylic acids and their salts, esters and amides substituted pyridines substituted pyridine carboxylases substituted pyridinones substituted pyrimidines substituted pyrimidones substituted pyrrolidine carboxylic acid and its salts, esters and amides substituted pyrrolidines substituted pyrrolidones substituted arylsulfonic acids and their salts, esters and amides substituted styrenes substituted tetrahydrooxadiazine diones substituted tetrahydroxadiazole diones substituted tetrahydromethanoinderes substituted tetrahydroxadiazole thiones substituted tetrahydrothiadiazine thiones substituted tetrahydrothiadiazole diones substituted aromatic thiocarbonylamides substituted thiocarboxylic acids and their salts, esters and amides substituted thiol carbamates substituted thioureas substituted thiophosphoric acids and their salts, esters and amides substituted triazines substituted triazoles o.z. 30,1 3 substituted uracils, and substituted uretidine diones.

The last-mentioned herbicidal compounds may also be applied before or after the active ingredients or compositions thereof according to the invention.

These agents may be added to the herbicides according to the invention in a ratio by weight of from 1 : 10 to 10 : 1. The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

The amount used of the agents according to the invention may vary and depends in essence on the type of effect to be achieved; it is generally from 0.1 to 15 (and more), preferably from 0.2 to 6, kg per hectare of active ingredient. The agents according to the invention may be used once or several times before or after planting, before sowing, and before, during or after emergence of the crop plants and unwanted plants.

The new compositions have a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth of unwanted plants. Whether the new active ingredients are used as total or selective agents depends in essence on the amount of ingredient used per unit area.

By weeds and unwanted plant growth are meant all mono-cotyledonous and dicotyledonous plants which grow in loci where they are not desired.

The agents according to the invention may therefore be used for controlling for instance Gramineae, such as Cynodon spp. Dactylis spp.

O.Z. 50,1 5 Digitaria spp. Avena spp.

Echinochloa spp. Bromus spp.

Setaria spp. Uniola spp.

Panicum spp. Poa spp.

Alopecurus spp. Leptochloa spp.

Lolium spp. Brachiaria spp.

Sorghum sppe Eleusine spp.

Agropyron spp. Cenchrus spp.

Phalaris spp. Eragrostis spp.

Apera spp. Phragmites communis etc . j Cyperaceae, such as Carex spp. Eleocharis spp.

Cyperus spp. Scirpus spp. etc.; dicotyledonous weeds, such as Malvaceae, e.g.

Abuti on theoprasti Hibiscus spp.

Slda spp. Mal a spp. etc.; Compositae, such as Ambrosia spp. Centaurea spp.

Lactuca spp. Tussilago spp.

Senecio spp. communis Sonchus spp. Tagetes spp.

Xanthium spp. Erigeron spp.

Iva spp. Anthemis spp.

Galinsoga spp. Matricaria spp.

Taraxacum spp. Artemisia spp.

O.Z. 50,1 3 Chrysanthemum spp. Bidens spp.

Cirsium spp. βtc _j Convolvulaceae, such as Convolvulus. spp . Cuscuta spp.

Ipomoea spp. Jaquemontia tamnifolla etc. ; Cruclferae, such as Barbai*ea vulgaris Arabidopsis thaliana Brassica spp. Descurainia spp.

Capsella spp. Draba spp.

Sisymbrium spp. Coronopus didymus Thlaspi spp. Lepidium spp.

Sinapis arvensis Raphanus spp. etc. ; Geraniaceae, such as Erodium spp. Geranium spp.

Portulacaceae, such as Portiilaca spp. etc.; Primulaceae, such as Anagallis arvensis Lysimaohia spp. etc.; Rubiaceae, such as Richardia spp. Diodia spp.

Galium spp. etc.; Scrophulariaceae, such as Linaria spp. Digitalis spp.

Veronica spp. etc.; Solanaceae, such as O.Z. 30,1 3 Physalis spp. Nicandra spp.

Solarium spp. Datura spp. etc . ; Urticaceae, such as Urtica spp.

Violaceae, such as Viola spp. etc. ; Zygophyllaceae, such as Tribulus terrestris etc.; Euphorbiaceae, such as Mercurialis annua Euphorbia spp, Umbelli erae, such as Daucus carota Ammi majus Aethusa cynapiutn etc.; Commelinaceae, such as Commelina spp. etc. ; Labiatae, such as Lamium spp. Galeopsis spp, etc . ; Leguminosae, such as Medicago spp. Sesbania exaltata Trifolium spp. Cassia spp.

Vicia spp. Lath rus spp. etc.; Plantaglnaceae, such as Plantago spp. etc.; Polygonaceae, such as Polygonum spp. Pagopyrum spp.

Rumex spp. etc.; O.Z. 30, Aizoaceae, such as Mollugo verticillata Amaranthaceae, such as Amaranthus spp. etc. ; Boraginaceae, such as Amsinckia spp. Anchusa spp.

Myostis spp. Lithospermum spp. etc. ; Caryophyllaceae, such as Stellaria spp. Silene spp.

Spergula spp. Cerastium spp.

Saponaria spp. Agrostemma githago Scleranthus annuus etc. ; Chenopodiaceae, such as Chenopodium spp. Atriplex spp. ochia spp. Monolepsis nuttalliana Salsola Kali etc.; Lythraceae, such as Cuphea spp. etc.; Oxalidaceae, such as Oxalis spp.

Ranunculaceae, such as Ranunculus spp. Adonis spp.

Delphinium spp. etc.; Papaveraceae, such as Papaver spp. Pumaria officinalis etc. ; Onagraceae, such as Jussiaea spp. etc. ; O.Z. 30,1 3 Rosaceae, such as Alchemillia spp. Potentilla spp, etc. ; Potamogetonaceae, such as Potamogeton spp. etc.; Najadaceae, such as Najas spp„ etc; Equisetaceae, such as Equisetum spp. etc. ; Marsileaceae, such as Marsilea quadrifolia etc.; Polypodiaceae, such as Pteridium quilinum Alismataceae, such as Alisma spp. Saglttaria sagittifolia etc , The agents according to the invention may be used in cereal crops such as Avena spp. Sorghum Triticum spp. Zea mays Hordeum spp. Panicum miliaceum Secale spp. Oryza spp.

Saccharum officinarum and in dicotyledon crops such as Cruciferae, e.g.

Brassica spp. Raphanus spp.

Sinapis spp. Lepidium spp.

Compositae, e.g.

Lactuca spp. Carthamus spp.

O.Z. 50,1 Helianthus spp. Scorzonera spp, Malvaceae, e.g. ί Gossypium hirsutum Leguminosae, e.g.

Medicago spp. Phaseolus spp.

Trifolium spp. Arachis spp.

Pisum spp. Glycine max.

Chenopodiaceae, e.g.

Beta vulgaris Spinacia spp.

Solanaeeae, e.g.

Solanum spp. Capsicum annuum Nicotiania spp.

Linaceae, e.g.

Linum spp.

Umbelliferae, e.g.

Petroselinum spp. Apium graveolens Daucus carota Rosaceae, e.g. Fragaria Cuourbitaceae, e.g.

Cucumis spp. Cucurbita spp, Liliaceae, e.g.

Allium spp.

Vitaceae, e.g.

Vitis vinifera Bromeliaceae, e.g.

Ananas sativus.

EXAMPLE 3 In the greenhouse, loamy sandy soil was filled into pots and sown with the seeds of various plants. The soil prepared O.Z. 30, in this manner was then immediately treated with 1 kg per hectare of each of the following active ingredients, each L being dispersed or emulsified in 500 liters of water per hectare; I 3- (2-trifluoromethyl)-cyclohexyl-5, 6-trimethylene uracil II 3- (3-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil III 3- (3-trifluoromethyl)-cyclohexyl-5, 6-trimethylene uracil IV 3- (2-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil and, for comparison, V 3-cyelohexyl-5, 6-trimethylene uracil.

After 3 to 4 weeks it was ascertained that active ingredients I to IV had better crop plant compatibility and a better herbicidal action than active ingredient V.

The results are given belows Active ingredient I II III IV V kg/ha 1 1 1 1 1 Crop plants: Pyrus communis 0 0 0 0 10 Malus domestica 0 0 0 0 15 Saccharum officinarum 0 0 0 0 15 Unwanted plants; Sinapis arvensis 100 100 90 85 90 Raphanus raphanistrum 100 100 90 90 90 Chenopodium album 95 95 90 85 90 Poa annua 80 100 85 90 85 Poa trivialis 80 100 85 90 . 85 Lolium perenne 85 100 85 80 80 Lolium multiflorum 80 100 85 80 80 O.Z. 30,1 Active ingredient II III IV V Echinochloa crus-galli 50 βθ 60 60 35 Avena fatua 50 50 40 50 15 0 = no damage, 100 = complete destruction.

EXAMPLE 4 In the greenhouse, various plants were treated with 1 kg per hectare of each of the following active ingredients, each being dispersed or emulsified in 500 liters of water per hectare: 1 3- ( 2-trifluoromethyl)-cyclohexyl-5i 6-trimethylene uracil II 3- (3-trifluoromethyl)-cyclohexyl-5°bromo-6-methyl uracil III 3- (3-trifluoromethyl)-cyclohexyl-5, 6-trimethylene uracil IV 3- (2-trifluoromethyl)-cyclohexyl-5~bromo-6-methyl uracil and, for comparison, V 3-cyclohexyl-5, 6-trimethylene uracil.

After 3 to 4 weeks it was ascertained that active ingredients I to IV had better crop plant compatibility and a better herbicidal action than active ingredient V.

The results are given below: Active ingredient I II III IV V kg/ha 1 1 1 1 1 Crop plants: Pyrus communis 0 0 0 0 10 Malus domestica 0 0 0 0 15 Saccharum of icinarum 0 0 0 0 15 Unwanted plantss Sinapis arvensis 100 100 80 75 75 Chenopodium album 80 85 70 70 65 O.Z. 30, 1 ? Active ingredient I II III IV V Poa annua 80 100 85 8o 75 Poa trivialis 80 100 80 80 70 Lolium perenne 65 100 80 75 60 Lolium multiflorum 60 100 8o 70 55 Echinochloa crus-galli 70 100 65 65 65 Avena fatua 50 100 50 55 20 0 = no damage 100 = complete destruction.

EXAMPLE 5 90 parts by weight of compound I is mixed with 10 parts by weight of N-methyl-a-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops EXAMPLE 6 20 parts by weight of compound II is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 paifts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of O moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein an aqueous dispersion is obtained containing 0.02$ by weight of the active ingredient.

EXAMPLE 7 20 parts by weight of compound I is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, O.Z. 30,143 0 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctyl-phenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100, 000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02$ by weight of the active ingredient.

EXAMPLE 8 20 parts by weight of compound III is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280°C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100, 000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0 , 02$ by weight of the active ingredient.

EXAMPLE 9 20 parts by weight of compound I is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-Oi- sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0. 1^ by weight of the active ingredient.

EXAMPLE 10 3 parts by weight of compound II is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained O.Z. 30,1 3 containing by weight of the active ingredient.

EXAMPLE 11 0 parts by weight of compound III is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

Claims (1)

1. 45635/2 CLAIMS: 1. 3-( Trifluoromethylcyclohexyl)- uracils of the formula 1 2 where R denotes halogen, R denotes alkyl of 1 to 3 carbon atoms, and R denotes hydrogen, and R1 may be linked to R2 by a methylene chain of the formula -(ΟΗ^)^-· 2. 3-(3-trifluoromethyl)-cyclohexyl-5-bromo-6-methyl uracil. . 2-( 2-trifluoromethyl)-cyclohexyl-5-bromo-6-methy1 uracil. 4. 3-( 3-trifluorometh 1)-cyclohexy1-5 , 6-trimethylene uracil. . 3-(2-trifluoromethy1)-cyclohexy1-5 ,6-trimethylene uracil. 6. Uracils of formula I in Claim 1, substantially as described herein with reference to the Examples. 7. A process for producing a substituted uracil of the formula I in Claim 1, wherein a mono-substituted urea of the formula s reacted with a β-keto ester of the formula alkyl - ^ ^R2 1 2 wherein R and R having the same meanings as in Claim 1, i i n with a ba e « 45635/2 8. A herbicidal composition comprising a substituted uracil of the formula I in Claim 1. 9. A herbicidal composition comprising a solid or liquid carrier and a substituted uracil of the formula I in Claim 1. 10. A process for producing a herbicidal composition of Claim 9 wherein a solid or liquid carrier is mixed with a substituted uracil of the formula I in Claim 1. 11. A process for controlling the growth of unwanted plants wherein the soil or the plants are treated with a substituted uracil of the formula I in Claim

1. H£:dn