NO137029B - AUTOMATIC SWITCH, SPECIAL PROTECTION SWITCH. - Google Patents

Abstract

Automatic switch, especially safety switch.

Description

Herbicidal preparations.

It is known to use 1,2-dihydro-pyridazine-3,6-dione as a means to re-

yellower plant growth and as a phytocidal agent.

It is further known that diazines, such as pyri-

midines, which may be substituted with halogen atoms, with low molecular weight alkyl radicals

dikals, amino-, alkyl-, amino-, dialkyl-

amino-, alkenylamino-, alkenylalkyl-

amino-, dialkenylamino-, alkoxy-, alkenyl-

oxy-, alkylmercapto-, alkenylmercapto-, polymethyleneimino- or morpholine radical-

ler, has an inhibitory effect on plant growth. It is also known that thiouracil, 4-, 5- and 6-mehtyl-thiouracil and uracil affect plant growth.

It was now found that preparations containing certain substituted uracils are particularly suitable for combating

weed species and the present invention

nelse concerns such preparations.

The characteristic main feature of the herbicidal preparations according to the invention is that they contain as active ingredient one or more substituted uracils with mole-

cooling weight up to 500, and which corresponds to the ge-

nerelle formula:

(in which R, denotes a radical with molecular weight from 15 to 250, namely a cyanoradi-

cal, an alkyl, alkenyl or alkynyl radical which may optionally be substituted with one or more fluorine, chlorine or bromine atoms, hydroxy-, alkoxy-, alkoxycarbonyl-, cyano-

or carboxy radicals, or an aryl or aralkyl radical which may optionally be substituted with one or more fluorine, bromine

or chlorine atoms, hydroxy-, alkoxy-, cyano-, alkylmercapto-, alkyl-, chloroalkyl-, nitro-

or trifluoromethyl radicals, or a cyclo-

alkyl or cycloalkenyl radical as even

can optionally be substituted with one or more fluorine, bromine or chlorine atoms,

or alkyl radicals, R2 denotes a radical with molecular weight from 1 to 250, namely an alkylmercapto-, alkoxy-, alkylmercapto-

alkyl, alkenyl, cyano-thiocyano or nitro radical, or a halogen or hydrogen atom, or an alkyl radical which eventually

elt can be substituted with one or more fluorine, bromine or chlorine atoms, cyan-, mer-

capto- or hydroxy radicals, R:! is a ra-

dikal with molecular weight from 1 to 200, namely an alkyl, alkoxy or haloalkyl radical or a hydrogen, chlorine or bromine atom,

or R2 and R;! can be tied to each

dre forming a divalent alkylene-

bridge with the formula (CH2)M, in which n is equal to 3, 4 or 5, Rj denotes a radical with molecular weight from 1 to 250, namely a dialkylphosphoryl, alkenyl, alkynyl or cyanra-

dical, a hydrogen atom or an alkyl radical

cal which may optionally be substituted with one or more bromine, chlorine or fluorine

atoms, hydroxy, alkoxy, alkoxycarbonyl, cyan or carboxy radicals, or a carbamyl or thiocarbamyl radical which may optionally be substituted with one or more alkyl, phenyl or chlorophenyl radicals, or a phenyl mercapto radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms, alkyl or alkoxy radicals, or an alkyl mercapto radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms or an optionally halogenated acyl radical which may be substituted with one or more phenyl radicals, which may optionally contain one or more bromine or chlorine atoms, or with one or more phenoxy radicals which may contain one or more chlorine or bromine atoms, and X denotes an oxygen atom or a sulfur atom, where-in the event that both R2 and R4 are hydrogen atoms — either R3 denotes an alkyl radical with from 1 to 6 carbon atoms, and R, denotes an alkyl radical with from 3 to 6 carbon atoms, an allyl or pro pynyl radical or a cycloalkyl or cycloalkenyl radical of from 5 to 8 carbon atoms, or R:! denotes a hydrogen atom, while R denotes a cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms, and where in the case that R2 is a hydrogen atom and R4 is a methyl radical, R is an optionally substituted cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms), and/or metal salts of such compounds.

According to the invention, particularly preferred herbicidal agents are those which contain one or more compounds in which R, in the general formula stated above, is a group corresponding to the general formula:

(in which R3 denotes a hydrogen atom or a methyl radical, R(i denotes a me-

ethyl radical or an ethyl radical and R7 denotes an alkyl radical with from 1 to 6 carbon atoms), R, is a chlorine atom or a bromine atom, R:! is a methyl radical and R is a hydrogen atom or an optionally halogenated acyl radical which may be substituted with one or more phenyl radicals which may optionally contain one or more bromine or chlorine atoms or a perchloromethylmercapto radical and/or metal salts of such compounds.

Furthermore, according to the invention, compounds are preferred in which the symbols in the above general formula have the following meanings: (a) R 1 : a cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms, R 2 : a chlorine atom or bromine atom, R ! : a methyl radical, R4 : the above-mentioned radicals with the exception of hydrogen and X: an oxygen atom or a sulfur atom. (b) R 1 : a cyclopentyl, cyclohexyl or cyclopenten-(2)-yl radical having from 5 to 8 carbon atoms, R 2 and R 4 : hydrogen atoms,

R;! : an alkyl radical with from 1 to 6, in particular from 1 to 4 carbon atoms, preferably a methyl radical and X: an oxygen atom or sulfur atom. (c) R, : the above-mentioned radicals, but preferably an alkyl radical or alkenyl radical with from 1 to 6 carbon atoms or an optional partially unsaturated cycloalkyl radical with from 5 to 8 carbon atoms, R 2 and R , : a divalent alkylene bridge with the formula (CH 2 ) n, in which n is 3 to 5, R4: the above-mentioned radicals, but preferably a hydrogen atom and X: an oxygen atom or sulfur atom. (d) R,: an alkyl radical with from 1 to 6 carbon atoms, an alkenyl radical or an optionally partially unsaturated cycloalkyl radical with from 5 to 8 carbon atoms, and X: a hydrogen atom.

When R4 in the above-mentioned general formula is a hydrogen atom, the compounds can exist in two modifications, namely:

The knowledge available now does not enable any unequivocal conclusion about whether the R4 substituent is in the 1- or 2-position.

The substituents on the alkyl, aryl, cycloalkyl, cycloalkenyl and aralkyl radicals can e.g. be fluorine, bromine, chlorine, nitro, sulfo, alkylsulfonyl, carbaloxy, cyano, mercapto, alkoxy, oxy or dialkylamino groups. Special examples of radicals for symbols R are alkyl groups with from 1 to 12 carbon atoms, phenyl-, hexyl-, p-phenethyl-, cyclohexyl-, cyclopentyl-,

cyclopenten-2-yl radicals and phenyl radicals which are substituted with halogen, ni-

tro groups, alkyl groups with from 1 to 4 carbon atoms and alkoxy groups with from 1 to 4 carbon atoms.

The metal salts of the compounds mentioned above can, e.g. be salts with alkali metals or alkaline earth metals such as sodium, potassium, lithium, calcium, magnesium, barium and strontium or with other metals such as divalent or trivalent iron, manganese and zinc.

Among the active substances that can be used according to the invention are, e.g. following and similarly substituted uracils:

The uracil derivatives used according to the invention are suitable for the control of weeds in general, as sterilizing agents for the soil, with application to the soil and on the leaves of plants, as selective herbicides and for the control of weeds before or after germination of weed species and useful plants . The compounds are active both against annual and perennial broad-leaved weed species and against grass species. They can be selectively applied to weeds that grow among beneficial plants such as e.g. asparagus, sugar cane, gladiolus, onions, potatoes, pineapple and safflower.

The quantity ratio in which the herbicides according to the invention are used depends on the state of the vegetation, the desired results, the preparation used, the application method, the climate, the season, the amount of rain and other variable conditions. In general, surprisingly small amounts of the active substance are required to combat weed plants before germination, generally from 56 g per acres. However, up to 225, 338, 450 or 564 g per acres or larger quantities. For application to the soil and leaves, it is generally necessary to use relatively large quantities. In general, at least 225 g should be used per hectare, preferably from 1.13 to 2.8 or 3.95 kg per acres. In some cases, larger quantities should be used, e.g. up to 9 kg per acres.

The alkali metal salts of the uracil derivatives are particularly advantageous for use as herbicidal agents because they are soluble in water and can be applied as aqueous solutions.

Herbicidal preparations containing uracil derivatives according to the invention can be prepared using conventional additives for parasiticides, such as modifiers and/or diluents (hereinafter collectively referred to as "inert carriers"). The herbicidal preparations can be in the form of powdery, solid substances, granules, pellets or liquids.

The liquid preparations can be solutions or suspensions. Like wettable powders, they preferably contain one or more surfactants in quantities sufficient to make the preparations easily dispersible in water or oils.

The term "surfactants" is considered here to include wetting agents, dispersing agents, agents for suspending solid substances in liquids and emulsifiers. Suitable surfactants are specified, e.g. in the U.S. Patents Nos. 2,426,417, 2,655,447, 2,412,510 and 2,139,276, "Soap and Chemical Specialties", 31, No. 7, pages 60-61, No. 8, pages 48-61, No. 9, pp. 52-67 and No. 10, pp. 38-67 (1955), McCutcheon: "Soap and Chemical Specialties," December 1957; January, February, March, 1958, and "Bulletin E-607" of the "Bureau of Entomology and Plant Quarantine of the U.S. Department of Agriculture".

In general, less than 10 wt. surfactants present in herbicidal preparations according to the invention, and the amount of surfactant in such preparations can be 1 wt. or less.

Powdery preparations or dusty preparations according to the invention can be prepared by mixing the active compound or compounds with finely divided, inert, solid carriers which preferably consist of talc, natural clay species, pyrophyllite, diatomaceous earth, synthetically produced finely divided silicic acid, calcium silicate and vegetable flour such as walnut shell flour, wood flour, wheat flour, soya bean flour and cottonseed flour. The carriers can also include magnesium carbonate and calcium carbonate, calcium phosphate, calcium silicate, sulfur and limestone, in the form of powders or granules.

The concentration of active compounds in preparations according to the invention varies according to the method of use of the preparation, and. is generally from 0.5 to 95% by weight. calculated on the total weight of the preparation.

Preparations in the form of pellets or granules can be prepared by mixing the active compounds in a finely divided state with a type of clay (with or without a water-soluble binder), moistening the mixture with from 15 to 20 percent water, extruding the resulting mass under pressure through an opening and cutting up the extruded material into pellets of the desired thickness before drying, or by first drying and then granulating into granules. Alternatively, granules, but generally not pellets, can be prepared by atomizing solutions or suspensions of the active material onto granules which have been formed in advance and which may consist of clay, vermiculite or other suitable material. When the active material is soluble in the liquid used so that it can penetrate the granules' pores, it is not necessary to use a binder. If, on the other hand, it is insoluble so that the liquid that is atomized is a suspension, it is necessary to add a binder to bring the active material to adhere to the surface of the granules. The binder can be a soluble substance such as "goulac" or dextrin or a substance that forms colloidal liquids such as swollen starch, glue or polyvinyl alcohol. In any case, the final step consists in removing the used liquid.

Herbicidal preparations according to the invention can also be prepared by suspending the active material in inert, non-aqueous carriers. As such carriers, it is preferred to use aliphatic and aromatic hydrocarbons such as e.g. coal water substances of mineral origin. The suspensions can be prepared by grinding the active material with dispersants and/or. suspending agents and inert carriers, e.g. in ball mills. The concentration of herbicide compound 1 in the suspensions can be from 10 percent or less and up to 48-50 percent calculated on the weight of the suspension.

Preferably, the particle size in such suspensions is from approx. 1 to 50 microns, with the majority of the particles having diameters from approx. 5 to 20 microns. As mentioned, the oils used are generally aliphatic and aromatic hydrocarbons or mixtures of such, particularly mineral hydrocarbons with a boiling point in the range from 125 to 400°C. Hydrocarbon oils with a boiling point lower than 125°C should not be used because they tend to volatilize excessively when atomized from nozzles. Furthermore, the use of low-boiling coal water substances is associated with a serious fire hazard.

Herbicidal preparations according to the invention may contain one or more substituted uracils and may, in addition to these, also contain known herbicidal substances. Among such known herbicidal compounds are the following: 2,3,6-trichlorobenzoic acid and salts of this acid

2,3,5,6-tetrachlorobenzoic acid and salts of this acid

2-chloro-N,N-diallylacetamide N,N-dipropylthiolcarbamic acid ethyl ester 2,2-dichloropropionic acid and salts of this acid

methylarsonic acid and salts of this acid borates chlorates ammonium sulfamate 2,4-dichlorophenoxyacetic acid

2.4.5- trichlorophenoxyacetic acid N-phenylcarbamic acid isopropyl ester

N-(m-chlorophenyl)-carbamic acid isopropyl ester tri-chloroacetic acid maleic hydrazide

1,1-dimethyl-3-(3,4-dichlorophenyl)furin)substance 1,1-dimethyl-3-(p-chlorophenyl)urea 1,1-dimethyl 1-3-phenylurinstof l-n-butyl-l-methyl-3-(3,4-dichlorophenyl)-urea l-methoxy-l-methyl-3 (3,4-dichlorophenyl)-urea

1- methoxy-1-methyl-3-(p-chlorophenyl)-urea 1,1,3-trimethyl-3-(3,4-dichlorophenyl)-urea 2- chloro-4,6-bis-(ethylamino) -s-triazine 2-chloro-4-ethylamino-6-isopropylamino-s-triazine

2-chloro-4,6-bis-(methoxypropylamino)-s-triazine

2-methoxy-4,6-bis-(isopropylamino)-s-triazine 2,4-bis-(isopropylamino)-6-methoxy-s-triazine dinitro-sec.-butylphenol 2.3.6- trichlorophenylacetic acid 5,6-dihydro -(4A,6A)-dipyrido-(1,2-A,2',

1'-C) pyrazinium dibromide 2,6-dichlorobenzonitrile

In herbicidal preparations according to the invention, adhesives such as gelatin, blood albumin and resins can optionally also be used, e.g. softwood resin and alkyd resins. Such substances can be used in certain preparations to increase the retention or duration of deposits of the preparations after application.

The active substances in the herbicidal preparations according to the invention can be prepared in one of the following ways, for which protection is not required here: A mono-substituted urea derivative or thiourine derivative is reacted in the presence of an acidic catalyst with an fS-keto acid ester in a in an essentially anhydrous environment while rapidly removing the water thus formed and then heating the formed <x,(3-unsaturated 3-(3'-substituted-ureido)-ester with a strong base. The metal salt thus obtained can be transferred to the free uracil derivative by reaction with an acid.

Suitable for this method are α,|3-unsaturated keto acid esters which are inert towards an essentially anhydrous acidic environment.

For the production of active compounds in which the symbols R2 and R4 are hydrogen atoms and R3 is an optionally substituted alkyl radical with from 1 to 6 carbon atoms, one can react an α,(3-unsaturated (3-amino acid residue) with an isocyanate or isothiocyanate and heating the thus formed α,(3-unsaturated 3-(3'-substituted-ureido)-acid ester with a strong base. From the metal salt thus obtained, the substituted uracil is obtained by adding acid. For related compounds, this reaction described in "Annalen d.Chemie", Vol. 314 (1901), page 219 and in "Berichte d. chem. Ges.", Vol. 33 (1900), page 622.

6-chlorouracil which is produced by acid hydrolysis of 2,4-dimethoxy-6-chloropyrimidine (see British patent no. 677 342) can be used as starting material for the production of e.g. 3-methyl-5,6-dichlorouracil and 3-methyl-5-bromo-6-methoxyuracil.

Uracil which is substituted in the 3- and 5-position can be prepared by reacting a uracil substituted in the 3-position with electrophilic reagents according to the equation:

In this equation, R2 denotes e.g. bromine, chlorine, CH2C1, CH2OH, -SCN or NO,. Methods for preparing analogous compounds are described in the following publications: JACS 61, 1015 (1939), Ann. 305, 314, Ann. 352, 252, Ann. 441, 192 and JACS 81, 2674

(1959) for halogen groups. Ann. 385, 293

(1911) for chloromethyl groups which can be reacted with alcohols, water or hydrocarbyl mercaptides to form alkoxymethyl, oxymethyl or hydrocarbyl mercaptomethyl groups. JACS 63, 2323 (1941), Org. Syntheses, Coll., Vol. II, 574 (1943) and Heiv. Chim. Acta, 19, 1411 (1936) for thiocyano groups,

JACS 30, 1150 (1908) for nitro groups.

The compounds in which R, is a hydrogen atom can be transferred to compounds in which R4 is another radical, by a substitution reaction of a known kind, e.g. using one of the following reaction components:

A general description of methods for producing some of the active substances that are substituted in the 1-position with alkyl, perchloromethyl, mereapto, aryl, aroyl, oxymethyl, arylsulfenyl, carbamyl and co-carboxylic acid alkane can be found in the following literature places:

US Patent 2,553,770

JOC 14, 1099 (1949) JACS, 52, 2006 (1930)

JACS 54, 2436 (1952)

Shirley: "Preparation of Organic Intermediates", 1951, page 59.

As mentioned above, the metal salts of the uracil derivatives used according to the invention can be prepared directly or by means of known methods such as dissolving the free uracil derivative in an aqueous or non-aqueous solution of at least an equimolecular amount of a base or a basic salt which contains the desired cation. Thus, one can e.g. prepare sodium salts by dissolving the uracil derivative in water containing an equimolecular amount of sodium hydroxide. The salt can be isolated by removing the water from the solution. The salts of the uracil derivatives which are not soluble in water can be prepared by treating an aqueous solution of the alkali metal salt of the uracil derivative with an aqueous solution of a water-soluble salt of the metal.

Table I below lists the results of some tests regarding herbicidal activity. In these experiments, the herbicidal activity of uracil, 2-thiouracil, 6-methyl-2-thiouracil and 2,4,6-trichloropyrimidine was compared with 22 active substances used according to the invention.

For the experiments after the germination of the weed species, the seeds were sown in the same soil and at a depth of 1.3 cm, calculated from the surface of the soil. About. 3 weeks after germination, the leaves and the soil were sprayed with the amounts of the tested compounds indicated in the table. 3 weeks after spraying, the degree of eradication of weed plants was determined. In the experiments before the germination of the weed plants, the seeds were sown on the same soil at a depth of 0.64 cm, calculated from the soil surface. Within 24 hours and before the seeds germinated, the areas were sprayed with the amounts of the compounds to be tested as indicated in the table. The degree of eradication of the weed plants was determined 3 weeks after spraying.

This table shows that the previously known compounds (experiments 1 to 4) are completely inactive, while with the compounds used according to the invention, a very good control of weed plants is achieved.

In a further series of experiments, the results of which are listed in Table II below, five of the active compounds in the preparations according to the invention were compared with 2-thiouracil. In this way, the compounds to be tested were applied before the weed plants germinated. The seeds were sown in the same soil at a depth of 0.64 cm, calculated from the surface of the soil. Immediately after the seeds were sown, the soil surface was sprayed with the amounts of the compounds to be tested as indicated in Table II. The degree of eradication of the weed plants was determined 21 days after spraying.

In the following examples, some herbicidal preparations according to the invention are shown as well as the results obtained with these.

Example 1 — Vandia susvension

The above-mentioned ingredients are mixed and ground in a ball mill or sand mill until the average particle size of the active ingredient is substantially less than 5 microns. The stable thixotropic suspension thus obtained does not form cakes and can easily be diluted with water to dilute suspensions in which the solids settle to the bottom very slowly so that they do not require stirring. the application.

Such aqueous suspensions can be used for local spraying in quantities

from 113 to 337 g per hectare of active substance in 114 liters of water and then provides effective control before germination of Echinochloa crusgallis, field mustard and Exhmochloa colonum 1 sugar cane plantations.

When using 3-isopropyl-5,6-tetramethyleneuracil in the same preparation form with 220 g of active substance per decares in 28 liters of water, good control is achieved before germination of Digitaria sp., mustard species, Chenopodium album and Enchinochloa in areas where sugar cane is grown.

When 3-cyclohexyl-6-methyluracil is used in the same preparation form to control weeds on railway bodies, long-term control of mixed vegetation such as Agropyron repens, Digitaria sp., Cynodon dactylon, Bromus tectorum, Ambrosia artemisiifolia, Xanthium sp., Chenopodium is achieved album and Erigeron canadensis.

When you use 5-bromo-3-cyclohexyl-1,6-dimethyluracil in the same preparation form as a spray liquid with from 110 to 120 g of active substance in 28 liters of water, good control is achieved before the germination of Digitaria sp., Avena fatua , Chenopodium album, Stellaria sp., Setaria sp., Ipomoea and of field mustard in areas where sugarcane, maize, Sorghum and Daucus carota are grown.

Example 2 -— Emulsifiable suspension in oil. 3-cyclohexyl-5-bromo-6-methyluracil 25% Mixture of polyalcohol-carboxylic acid esters and oil-soluble petroleum sulphonates 6% Diesel oil 69%

The above-mentioned ingredients are mixed and ground in a roller mill, ball mill or sand mill until the particles of the active ingredient are essentially all below a size of 10 microns. The suspension thus obtained can be emulsified in water or diluted with oils used in herbicidal preparations for use in spraying.

Preparations can be diluted with 748 liters of "Lion Herbicidal Oil-No. 6" and applied in a quantity ratio of 1.35 kg/acre of active ingredient for combating plants of the species Ipomea sp. and Achillea, Ambrosia artemisiifolia, Daurus carota, Agropyron repens, Panicum capillare, Digitaria sp. as well as sprouts of oak and maple growing along railway bodies. You get a very good eradication of the plants.

Example 3 — Emulsifiable oil 3-isopropyl-5-bromo-6-methyluracil 20.0% alkyl-aryl-polyether alcohol 2.5% Oil-soluble petroleum sulfonate 2.5% Methyl isobutyl ketone 65.0%

This emulsifiable oil is prepared by mixing the above-mentioned ingredients until a homogeneous solution is obtained. This can be emulsified with water before use.

This emulsifiable oil is beneficial for controlling weeds along railway bodies, on railway plots and sidings. When the preparation is diluted with water and sprayed on from a railway spray truck in a quantity ratio corresponding to 1.13 to 2.25 kg of active ingredient and 93.5 liters of water per decares, mixed vegetation such as Agropyron repens, Digitaria sp., Cynodon dactylon, Bromus tectorum, Ambrosia artemisiifolia, Xanthium sp., ChenopOdium album and Erigeron canadiensis is eradicated for long periods of time.

The following compounds can be processed into preparations and used in the same way as described in example 3: 3-sec.-butyl-5-fluoro-6-methyluracil

3-isopropyl-5-bromouracil 3-sec-butyl-5-bromo-6-methyluracil Example 4 — Pellets

The ingredients are mixed and micropulverized, after which they are moistened with 18-20 percent water and extruded through nozzles. The extruded strands are cut as they are formed to obtain pellets that are dried.

These pellets are beneficial for fighting weeds along well fences, around bridges and cyclone screens as well as posts with guides. They are applied appropriately by hand in a ratio of 11.3 to 2.7 kg per acres of active ingredient. You achieve a very good eradication of plants such as oak, maple, willow and. Liquidambar styraciflua.

From the following compounds, preparations can be prepared in the same form as in example 4 and which can be used in the manner described in this example: 3-tert.-amyl-5-bromo-6-methyluracil 3-butyl-6-methyluracil and 3- tert-butyl-5-bromouracil

Other compounds that can be processed into preparations and used as indicated above are the following: 3-cyclohexyl-1,6-dimethyluracil and 3-isopropyl-5-bromo-1-dimethylcarbamyl- 6-methyluracil.

Example 5 — Wettable powder.

The ingredients are mixed and finely ground to a particle size substantially below 50 microns. It is then micropulverized until essentially all particles have a particle size below 10 microns.

The preparation obtained can be used before germination on fields for the cultivation of useful plants such as sugar cane, asparagus and safflower. The powder is suspended in 37 liters of water per acres and applied with a pressure sprayer. When using 56 to 225 active ingredient per decares achieves very good control of Amaranthus sp., chenoopodium album, Portulaca olera-cea, field mustard, Digitaria sp., Setaria sp. and Echinochloa sp.

The calcium salt is used in the same preparation form as a general weed control agent on industrial sites and railway sites. 1.12 to 2.24 kg of active substance per acres in 94 liters of water gives a very good control of Solidago sp., Oenothera, Phytolacca americana, Chrysanthemum leucanthemum, Xanthium sp., Potentilla anserina, Digitaria sp. and Eragrostis pecti-nacea. 2.24 kg of active substance per acres in 47 liters of water gives a very good control of Gyperus.

With 3.4 kg of active substance per decares, with local treatment you get very good control of weeds with deep roots such as Convolvulus and Cirsium arvense.

The following compounds can be processed into preparations and used in the manner indicated above:

3-phenyl-5-bromo-6-methyluracil,

, 3-sec-butyl-5-chloro-6-ethyluracil, 3-sec-amyl-5-bromo-6-methyluracil,

3-(p-chlorophenyl)-5-6-methyluracil, 3-isopropyl-5-thiocyan-6-methyluracil and 3-benzyl-5-chloro-6-methyluracil.

Example 6 — Granulate.

These granules are produced by dissolving the active substance in water and spraying the solution onto the granules of vermiculite while they are in motion. The product is then dried.

This granulate is used for local treatment in areas where Centaurea repens, Convolvulus and perennial weeds with deep roots grow. Application takes place using a specially designed spreading device in. a quantity of 14.6 kg per acres.

Example 7 — Soluble powder.

These substances are mixed and micropulverized, resulting in a flowable powder that does not form cakes. When water is added, the active ingredient dissolves quickly while the silicic acid is suspended.

This preparation can be used to control mixtures of annual and perennial weed plants that grow around buildings in farms. When applying 1.7 kg of active ingredient per decares in 56 liters of water achieves very good control of Lepidium, field mustard, Arctium, Agropyron repens and Digitaria sp.

Example 8 — Suspension in oil.

This suspension is prepared by grinding the active substance in advance and mixing it with the other ingredients while stirring, or by mixing all the ingredients together, with subsequent grinding in ball mills or sand mills, so that the particle size of the active ingredient is reduced. The product is suitable to be diluted into spraying liquids with oil for use in herbicidal preparations.

The preparation can be diluted with 75 liters of an oil of the aforementioned type, such as e.g. "Lion Herbicidal Oil No. 6" is applied in a quantity of 1.35 kg of active ingredient per acres for general weed control along fences and railway tracks. A strong eradication of the plants is achieved for long periods of time. Good control of Agropyron repens, Bromus secalinus, Panicum capillare, Diodia teres and Datura stramonium is achieved.

Other compounds which have been shown to be equally effective when processed into preparations and used in the manner indicated above are the following: l-acetyl-3-cyclohexyl-5-bromo-6-methyl-uracil, l-acetyl-3-rsek .-butyl-5-chloro-6-methyl-uracil, 3-isopropyl-5-chloro-6-methyl-1-trichloro- acetyluracil and

3-tert-butyl-5-chloro-6-methyl-propionyl-uracil.

Example 9 — Pellets.

The following substances are mixed and micropulverized, after which they are moistened with 18-20 per cent water and extruded through nozzles with a small opening. The extruded material is cut as it is formed, so that you get small pellets which are then dried.

With these pellets, weeds can be eradicated along road fences, around bridges, under windscreens and road markings. The preparation is applied by hand in quantities from 1.7 to 3.4 kg of active ingredient per acres. A very good eradication of the sprouts Solidago sp., Oenothera, Phytolacca americana, Andropogon virginicus and Panicum is achieved.

Example 10 — Aqueous concentrate.

This aqueous concentrate is prepared

by dissolving the two solid ingredients listed below in water. The preparation can be easily diluted to application concentrations and sprayed.

This aqueous concentrate is applied with

a hand syringe that works under pressure.

170 to 340 g of active ingredient per decares in 151 liters of water gives a very good control before germination of Setaria sp., Echinochloa sp. and sprouts of Sorghum halepense.

Claims (2)

1. Herbicidal preparations, charac- characterized by the fact that they contain as an active ingredient one or more substituted uracils with a molecular weight up to 500, and which correspond to the general formula: (in which R, denotes a radical with a molecular weight from 15 to 250, namely a cyan radical, an alkyl-, alkenyl - or alkynyl radical which may optionally be substituted with one or more fluorine, chlorine or bromine atoms, hydroxy, alkoxy, alkoxycarbonyl, cyan or carboxy radicals, or an aryl or aralkyl radical which may optionally be substituted with one or more fluorine, bromine or chlorine atoms, hydroxy, alkoxy, cyano, alkyl mercapto, alkyl, chloroalkyl, nitro or trifluoromethyl radicals, or a cycloalkyl or cycloalkenyl radical which may optionally be substituted with one or several fluorine, bromine or chlorine atoms, alkoxy or alkyl radicals, R2 denotes a radical with molecular weight from 1 to 250, namely an alkylmercapto-, alkoxy-, alkylmercaptoalkyl-, alkenyl-, cyano-, thiocyano- or nitro radical, or a halogen or hydrogen atom, or an alkyl radical which may optionally be substituted with one or more fluorine, bromine or chlorine atoms, cyan, mercapto or hydroxy radicals, R3 is a radical with molecular weight from 1 to 200, namely a alkyl, ' alkoxy or haloalkyl radical or a hydrogen, chlorine or bromine atom, or R0 and R3 can be bonded to each other forming a divalent alkylene bridge of the formula (CH2)n, in which n is equal to 3/4 or 5, R4 denotes a radical with molecular weight from 1 to 250, namely a dialkylphosphoryl- , alkenyl, alkynyl or cyano radical, a hydrogen atom or a alkyl radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms, hydroxy, alkoxy, alkoxycarbonyl, cyan or carboxy radicals, or a carbamyl or thiocarbamyl radical which may optionally be substituted with one or more alkyl, phenyl or chloro-phenyl radicals, or a phenyl mercapto radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms, alkyl or alkoxy radicals, or an alkyl mercapto radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms or an optionally halogenated acyl radical which may be substituted with one or more phenyl radicals, which may optionally contain one or more bromine or chlorine atoms, or with one or more phenoxy radicals which may contain one or more chlorine or bromine atoms, and X denotes an oxygen atom or a sulfur atom, where — in the event that both R 2 and R , are hydrogen atoms — either R 3 denotes an alkyl radical of from 1 to 6 carbon atoms, and R , denotes an alkyl radical of from 3 to 6 carbon atoms, a allyl or propynyl radical or a cycloalkyl or cycloalkenyl radical of from 5 to 8 carbon atoms, or R3 denotes a hydrogen atom, while R, denotes a cycloalkyl or cycloalkenyl radical of from 5 to 8 carbon atoms, and where in the case that R2 is a hydrogen atom and R4 is a methyl radical, R is an optionally substituted cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms), and/or metal salts of such compounds. 2. Herbicidal preparations according to claim 1, characterized in that they contain one or more compounds in which, in the general formula stated in proposition 1, Rt denotes a group corresponding to the general formula: - (in which R5 denotes a hydrogen atom or a methyl radical, RG denotes a methyl radical or an ethyl radical and R7 denotes an alkyl radical with from 1 to 6 carbon atoms), while R2 denotes a chlorine atom or a bromine atom, R3 denotes a methyl radical and R, denotes a hydrogen atom, or an optionally halogenated acyl radical which may be substituted with one or more phenyl radicals which may optionally contain one or more bromine or chlorine atoms, or a perchloro-methylmercapto radical, or salts of such compounds.