NO152166B - DEVICE FOR WATERING OF Aqueous Suspensions and Sludge - Google Patents

Description

Herbicides.

The present invention relates to herbicidal agents containing as active ingredient new heterocyclic compounds with an oxygen atom and a nitrogen atom in the heteroring, and which can be described as oxazinones.

Many heterocyclic compounds with one nitrogen atom and one oxygen atom in the heteroring are known. Such compounds are described e.g. in US Patent Nos. 2,832,680, 2,911,294, 2,329,619, 2,297,217 and 2,447,822. The heterocyclic compounds used as herbicides according to the present invention clearly differ from the compounds disclosed in these US patents in that, as described in more detail below, they show a prominent herbicidal activity against a large number of unwanted plants, while are there any indications that the compounds described in the aforementioned US patents are herbicidal in application quantities that are applicable in practice.

The active compounds in the herbicidal agents according to the invention correspond to the following general formula:

In this general formula, R^ denotes an alkyl radical with from 1 to 10 carbon atoms, or an optional alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl, cycloalkylalkyl, cycloalkenylalkyl or bicycloalkylalkyl radical with 5-12 carbon atoms, a phenyl radical, or an optional alkyl substituted aralkyl radical with 7-10 carbon atoms,

R 2 denotes a hydrogen, chlorine or bromine atom, or an alkyl radical

with 1-4 carbon atoms, whereas

R3 denotes an alkyl radical with 1-5 carbon atoms.

In the above definition of R^, "cycloalkyl", "cycloalkenyl", "bicycloalkyl", "cycloalkylalkyl", "cycloalkenylalkyl" and "bicycloalkylalkyl" are intended to include radicals such as:

cyclohexyl

cyclohexenyl

cyclohexylalkyl'

cyclohexenylalkyl

cyclopentyl

cyclopentenyl

cyclopentylalkyl

cyclopentenylalkyl

norbornyl

norbornenyl

norbornylalkyl

norbornenylalkyl

bicyclo-(2,2,2)-oethyl

bicyclo-(2,2,2)-octenyl

bicyclo-(2,2,2)-octylalkyl

bicyclo-(2,2,2)-octenylalkyl

cyclobutylalkyl

cyclobutenylalkyl

hexahydroindanyl

tetrahydroindanyl

hexahydroindenyl

hexahydroindenyl-alkyl

tetrahydroindanyl-alkyl

hexahydroindanyl-alkyl

decahydronaphthyl

decahydronaphthyl alkyl

tetrahydronaphthyl and

tetrahydronaphthyl alkyl.

The non-alkyl-substituted of these cyclic substituents may optionally be substituted with alkyl groups containing from 1 to 4 carbon atoms.

"Aralkyl" and "alkyl substituted aralkyl" likewise under the definition of R^ are intended to include radicals such as:

benzyl

The compounds corresponding to the above general formula I can suitably be used in the form of salts with organic or inorganic acids. The free bases are highly unstable and it is therefore generally preferred to use the salts. Some examples of such salts are salts of acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, sulfamic acid, benzoic acid, acetic acid, phosphoric acid, phthalic acid, citric acid, succinic acid, maleic acid, tartaric acid, propionic acid, dichloroacetic acid, trichloroacetic acid, α,α-dichloropropionic acid and the like.

Compounds corresponding to the above general formula I can be prepared in a simple and advantageous manner by a two-step process as follows:

Step 1:

A substituted acetoacetamide is reacted with ammonia, whereby a substituted p-aminocrotonic acid amide is formed.

Step 2:

The p-aminocrotonic acid amide thus obtained is reacted with phosgene, whereby the corresponding oxazin-2-one hydrochloride is formed.

This procedure takes place according to the following reaction equations:

Step 1:

Step 2:

In this reaction scheme, R^, R^ and R^ have the meanings given in the general formula I.

The acetacetamides used in step 1f are produced either by reacting an amine with a diketone, as described below, or by reacting a (J-ketoester with an excess of an amine and subsequent treatment with an aqueous acid.

The acetamide used as starting material can be prepared by reacting the diket with an amine in accordance with the reaction equation:

This method is described in more detail in US patent no. 2,615,917.

As an example of how salts of the oxazinones can be obtained, the following describes the preparation of 6-imino-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one hydrochloride from a p-aminocrotonic acid amide and phosgene.

A solution of phosgene is prepared in a suitable, inert, organic solvent such as tetrahydrofuran, dioxane, acetonitrile, 1,1,2-trichloroethylene or the like. A solution or suspension of the p-aminocrotonic acid amide, preferably in the same solvent as the phosgene, is mixed with the solution of the phosgene.

Equimolecular amounts of p-aminocrotonic acid amide and phosgene can be used, but it is preferred to use a small excess of phosgene to achieve improved efficiency and for economic reasons. In general, the amount of phosgene used does not exceed 5 mol, and preferably not 2 mol per mol of p-aminocrotonic acid amide.

It is advantageous to add the solution or suspension of this amide to the solution of phosgene and continue the addition of phosgene so that this is kept in excess and that the solution is saturated with phosgene. Pressures higher than atmospheric pressure can advantageously be used there.

This reaction is highly exothermic, as a large amount of heat is developed during the mixing of the (3-aminocrotonic acid amide and the phosgene. It is desirable to carry out the mixing operation at a moderate temperature, e.g. at 25 - 50° C , to make the evaporation of the phosgene as little as possible.External cooling can be used when this is necessary to keep the temperature within the above-mentioned range.

When the operation consisting of mixing the p-aminocrotonic acid amide and phosgene is complete, the mixture, which now contains a solid substance as another phase, is heated to a temperature of approx. 40°C to approx. 100°C for a period of time from approx. 30 minutes to approx. 6 hours to complete the reaction. The desired hydrochloride of 6-amino-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one is then formed there. This compound can be collected by any suitable means such as filtration or decantation of the supernatant.

This hydrochloride can be transferred to other salts of the oxazinone by means of conventional reactions or by neutralization of the hydrochloride, e.g. by using solvoxide suspended in an inert solvent such as methylene chloride with subsequent filtration of the solv chloride and addition of the acid required to form the desired salt. Salts of acids weaker than hydrochloric acid can be prepared by suspending or dissolving the oxazinone hydrochloride in an inert solvent (or more easily in the weaker acid if this is a liquid), adding the appropriate amount of the weaker acid and a salt of that acid , e.g. the sodium salt and filter off or otherwise remove the aqueous chloride.

The oxazinone salts in which there is chlorine or bromine can be prepared by conventional halogenation methods, e.g. by reaction with the halogen in glacial acetic acid or another solvent.

The oxazinone salts generally do not have distinct melting points. When heated, they lose hydrogen chloride and change to the corresponding uracil.

The oxazinone salts are soluble in water and somewhat soluble in highly polar organic solvents such as acetic acid and alcohols, but are insoluble in less polar organic solvents.

The oxazinone salts show a distinct absorption in the infrared region of the spectrum. Characteristic features are (a) the lack of absorption in the N-H stretching frequency, (b) an intense absorption at 1770-1910 cm"^ attributable to the group

in the molecule corresponding to the above general formula I, (c) multiple absorption in the range 1570 to 1660 cm \ probably due to absorption of the groups

and (d) adsorption of agents

intensity in the range 1510 - 1515 cm<-1>, which is characteristic of monosubstituted amides. Nuclear magnetic resonance studies and absorption in the ultraviolet region of the spectrum are consistent with the oxazinone ring system attributed to the compound.

The oxazinones used according to the invention can exist in three tautomeric structures, namely the following:

A particularly prominent herbicidal activity has salts of oxazinones in which R2 is hydrogen, chlorine or bromine and R3 is a methyl group in the foregoing general formula I.

Illustrative of preferred herbicidal compounds are salts, especially the hydrochlorides and hydrobromides of the following oxazinones: 6-sec-butylimino-5-chloro-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-sec -butylimino-5-bromo-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-norbornylimino-3,6-dihydro-4-methyl-2H-1,3-oxazin- 2-Mon

6-norbornylmethylimino-5-bromo-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-(1-ethylpropylimino)-5-bromo-3,6-dihydro-4-methyl -2H-1,3-oxazin-2-one 6-(1,3-dimethylbutylimino)-5-chloro-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-i sopropylimino-5-bromo-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-tert-butylimino-5-bromo-3,6-dihydro-4-methyl-2H-1 ,3-oxazin-2-one 6-phenylimino-5-bromo-3,6-dihydro-4-methyl-2H-1,3-oxazin-2-one 6-cyclohexylimino-5-bromo-3,6-dihydro -4-methyl-2H-1,3-oxazin-2-one

As illustrative of the activity of the oxazinones' salts, mention is made of 6-tert-butylimino-3,6-dihydro-4-methy1-2H-1,3-oxazin-2-one hydrochloride, 6-(2-norbornylmethylimino)-3,6 -dihydro-4-methyl-2H-1,3-oxazin-2-one hydrochloride, 6-(p-methylbenzylimino)-3,6-dihydro-5-bromo-4-methyl-2H-1,3-oxazine -2-one hydrobromide and 5-bromo-4-methyl-6-phenyl-imino-6H-1,3-oxazin-2(3H)one hydrobromide by pre-emergent application in quantities of 224 g per acres, each effectively combats Digitaria sp., Avena fatua (flood oats), Brassica sp., Tagetes sp. and Phaséolus vulgaris (bean plants).

The compounds which correspond to the above general formula have herbicidal action both against broad-leaved plants and harmful grass species, are effective against weeds which are difficult to eradicate such as Cyperus, and perennial grass species such as Agropyron repens, Sorghum halepense and Cynodon dactylon. They are also effective when used on highly absorbent substrates such as railway bodies, soil consisting of heavy clay and soil with a high content of organic substances.

This combination of properties makes the use of these compounds advantageous in any case where a general extermination of weeds is required such as in industrial areas, on railway sites and areas adjacent to areas where useful plants are grown.

Some of the compounds also show a selective herbicidal action among beneficial plants. With the correct selection of the oxazinones used according to the invention, of quantities and time of application, sprouts of annual grass species and broad-leaved plants can be combated in areas where useful plants such as asparagus, maize, flax, sugar beet, pineapple, safflower are grown. , peanuts, citrus fruits, alfalfa grass, strawberries, gladiolus, stone fruit trees and pumpkins.

With the correct selection of quantities and time of application, certain of these oxazinones can also be used to combat weeds that grow in areas where useful plants are grown that have not yet germinated.

The exact amounts of the oxazinones used according to the invention that must be applied in any specific situation, of course, vary in accordance with the desired result, the target of application, the plants and the soil that are prepared, the preparation used, the prevailing climatic conditions , density of leaf growth and similar factors. As so many variable conditions come into play, it is not possible to specify amounts that are suitable for every situation. In very general terms, however, the compounds can be used in amounts from approx. 28 g per acres to approx. 2.8 kg per acres. For the selective eradication of weeds among useful plants, amounts from 56 to 902 g per acres. Larger quantities of the active substances can be used to eradicate species which are difficult to combat and which grow under difficult conditions. Economic factors such as inaccessibility in the area to be treated, such as e.g. fire plots in forests, may also require the use of larger quantities during less frequent treatments.

In the following tables 1 and 2 are listed the results of some trials regarding the herbicidal activity of oxazinones used according to the invention.

In these experiments, the herbicidal activity was judged according to a scale with numerical values from 0 to 10, where 0 denotes no damage to the plants used in the experiments, and the numbers from 1 upwards denote a gradually decreasing activity to 0, which means complete eradication of the plant in question. The herbicidal effect consisted in all cases of chlorosis-necrosis effects.

The herbicidal compounds used according to the invention can be processed into herbicidal preparations in stick form, or into wettable or soluble powders. When preparing such preparations, care must be taken that diluents, surfactants as well as other parasiticides that may be added have a neutral pH value and are completely free of alkalinity. It is also important that the components of the preparations are dry and that water is strictly excluded during the processing of the components, the preparation of the preparations and their storage. As far as possible, the diluents and surface-active agents, such as other additives, should also be chemically inert as well as

reasonably free of active OH groups.

Particularly advantageous results are achieved by using practically water-free preparations with a composition within the following ranges: Active ingredient (oxazinone salt) 30 - 60% by weight Non-ionic surfactant 0.1 - IO "

The rest inert diluent to 100% by weight

By "practically anhydrous" is meant here that the amount of water that is present is a maximum of 1% by weight calculated on the weight of the oxazinone salt present.

Suitable diluents for the production of stbv preparations and wettable powders are finely divided, powder-like solids with a neutral or slightly acidic surface reaction, such as synthetically produced finely divided silicic acid, diatomaceous earth and acidic kaolin clay species. Examples of such are "Hi-Sil", "Celite" 209, "Continental clay", "Barnet clay" and "Pike's Peak clay 9T66". Other diluents that can be used in some cases include other inert vegetable flours, such as rbdtree (Wellingtonia) flour, walnut flour and the like.

When using such diluents for the production of solid-form preparations, the active ingredient is preferably present in amounts from 0.5 to 15%, the remainder being mainly one or more of the above-mentioned diluents. In the production of wettable powders, the active ingredient can be present in amounts from 10 to 85%, the remainder being the diluent and from 0.1 to 5% or 10% of one or more of the surfactants specified below.

Surfactants for use in these preparations can be of anionic, cationic or non-ionic types, anionic surfactants being preferred and particularly non-ionic ones. It is important that anionic surfactants are not strongly alkaline. With this limitation, such surfactants as salts of alkylarylsulphonic acids and petroleum sulphonates and salts of fatty alcohol sulphates can be used. A list of such surfactants is provided in "Detergents and Emulsifiers Up-to-date, 1962" by John W. McCutcheon, Inc. Other anionic surfactants which may be used are salts of the dialkyl esters of sulfosuccinates and of the fatty acid esters of isethionic acids. In some cases, free acids can be used instead of the salts.

Among the particularly preferred nonionic surfactants are polyethylene glycol fatty acid esters and polyoxyethylene ethers as well as -thioethers. Other non-ionic compounds that can be used are alkylphenoxypolyethyleneoxyethanols, such as nonylphenyl adducts with ethylene oxide, trimethylnonyl polyethylene glycol ether, polyethylene oxide adducts of fatty acids and kdlofonium acids, polyethylene oxide adducts of sorbitan esters of fatty acids and rosin acids and alkyl mercaptan adducts with ethylene oxide, with a long chain. Particularly preferred are polyglycol ethers in which both alcohol end groups are esterified with fatty acids such as lauric acid, oleic acid, palmitic acid or stearic acid e.

Other surface-active dispersants such as low-viscosity methyl cellulose or practically neutral sodium lignosulphonates are also advantageous, particularly in wettable preparations according to the invention.

In many cases it is desirable to process the compounds used according to the invention into soluble solid herbicidal preparations. Such preparations can consist of from 75 to 95% of the active ingredient, while the rest is one or more of the above-mentioned surfactants. For the preparation of such preparations, the diluent and/or the surface-active agent is mixed with the active ingredient in a conventional manner, after which the mixture is ground. As mentioned above, care must be taken to ensure that moisture is excluded.

The herbicidal agents according to the invention may contain

two or more compounds corresponding to the foregoing general formula I, and/or salts of such compounds. They may also contain other known herbicidal compounds, whereby preparations are obtained which have advantageous properties over the properties of the individual components.

Among the known herbicidal agents which can be combined with compounds corresponding to the preceding general formula I are: Substituted urea derivatives

3-(3,4-dichlorophenyl)-1,1-dimethylurea

3-(4-chlorophenyl)-1,1-dimethylurea

3-phenyl-1,1-dimethylurea

3-(3,4-dichlorophenyl)-3-methoxy-1,1-dimethylurea 3-(4-chlorophenyl)-3-methoxy-1,1-dimethylurea 3-(3,4-dichlorophenyl)-1-n- butyl-1-methylurea 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea 3-(4-chlorophenyl)-1-methoxy-1-methylurea 3-(3,4-dichlorophenyl)-1,1 ,3-trimethylurea 3-(3,4-dichlorophenyl)-1,1-diethylurea

3-(n-chlorophenoxyphenyl)-1,1-dimethylurea

These urea derivatives can be mixed with the oxazinones according to the invention in a quantity ratio of from 1:4 to 4:1, the preferred ratio being from 1:2 to 2:1.

Substituted triazines

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 -diethylamino-4-isopropylacetamido-6-mathoxy-s-triazine 2-isopropylamino-4-methoxyethylamino-6-methyl-mercapto-s-triazine 2-methylmercapto-4,6-bi s-(isopropylamino)-s- triazine 2-methylmercapto-4,6-bis-(ethylamino)-s-triazine 2-methylmercapto-4-ethylamino-6-isopropylamino-s-triazine 2-methoxy-4,6-bis-(ethylamino)-s -triazine 2-methoxy-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis-(isopropylamino)-s-triazine

These triazines can be mixed with the compounds according to the invention in a quantity ratio of from 1:4 to 4:1, the preferred quantity ratio being from 1:2 to 2:1.

Phenols

Dinitro-o-sec-butylphenol and the salts of this compound Pentachlorophenol and the salts of this compound

These phenols can be mixed with the compounds according to the invention in proportions from 1:10 to 20:1 respectively, preferably from 1:5 to 5:1.

Carboxylic acids and derivatives thereof

The following carboxylic acids and carboxylic acid derivatives can be mixed with the compounds according to the present invention in the proportions stated below: A. 2,3,6-trichlorobenzoic acid and its salts

2,3,5,6-tetrachlorobenzoic acid and its salts

2-Methoxy-3,5,6-trichlorobenzoic acid and its salts 2-Methoxy-3,6-dichlorobenzoic acid and its salts 3-amino-2,5-dichlorobenzoic acid and its salts

3-nitro-2,5-dichlorobenzoic acid and its salts

2-methyl-3,6-dichlorobenzoic acid and its salts 2,4-dichlorophenoxyacetic acid salts and esters of this 2.4.5-trichlorophenoxyacetic acid and its salts and esters (2-methyl-4-chlorophenoxy)-acetic acid, its salts and esters 2-(2,4,5-trichlorophenoxy)-propionic acid, the salts and esters thereof 2-(2,4,5-trichlorophenoxy)-ethyl-2,2-dichloropropionate 4-(2,4-dichlorophenoxy)-butyric acid, the salts and esters of this 4-(2-methyl-4-chlorophenoxy)-succinic acid, the salts and esters of this 2.3.6-trichlorobenzyloxypropanol

mixed in the proportions 1:16 to 8:1, preferably from 1:4 to 4:1.

B. 2,6-Dichlorobenzonitrile

mixed in the proportions 1:4 to 4:1, preferably from 1:3 to 3:1.

C. Trichloroacetic acid and its salts

are mixed in proportions from 1:2 to 25:1, preferably from 1:1 to 8:1.

D. 2,2-dichloropropionic acid and its salts

are mixed in proportions from 1:4 to 8:1, preferably from 1:2 to 4:1.

E. N,N-di-(n-propyl)-thiolcarbamic acid ethyl ester N,N-di-(n-propyl)-thiolcarbamic acid n-propyl ester N-ethyl-N-(n-butyl)-thiolcarbamic acid ethyl ester N-ethyl -N-(n-butyl)-thiolcarbamic acid-N-propyl ester

are mixed in proportions from 1:2 to 24:1, preferably from 1:1 to 12:1.

F. N-phenylcarbamic acid isopropyl ester

N-(m-chlorophenyl)-carbamic acid isopropyl ester

N-(m-chlorophenyl)-carbamic acid 4-chloro-2-butynyl ester

are mixed in proportions from 1:2 to 24:1, preferably from 1:1 to 12:1.

G. 2,3,6-trichlorophenylacetic acid and its salts are mixed in proportions from 1:12 to 8:1, preferably from 1:4 to 4:1.

H. 2-Chloro-N,N-diallylacetamide

maleic hydrazide

are mixed in proportions from 1:2 to 10:1, preferably from 1:1 to 5:1.

Inorganic salts and mixtures of inorganic and organic salts

The following salts can be mixed with the oxazinones according to the invention in the quantities specified below:

A. Calcium propyl arspnate

Disodium monomethylarsonate

Octyl-dodecylammonium methylarsonate

Dimethylarsinic acid

are mixed in proportions from 1:4 to 4:1, preferably from 1:2 to 2:1.

B. Sodium arsenite

are mixed in proportions from 1:5 to 40:1, preferably from 1:4 to 25:1.

C. Lead arsenate and calcium arsenate

are mixed in proportions from 150:1 to 600:1, preferably from 100:1 to 400:1.

D. Sodium tetraborate-hydrated, granulated

Sodium metaborate

sodium pentaborate

Polyboron chlorate

Unrefined borate ore, such as "borascu"

are mixed in proportions from 3:1 to 1500:1, preferably from 6:1 to 1000:1.

E. Ammonium thiocyanate

are mixed in proportions from 1:10 to 20:1, preferably from 1:5 to 5:1.

F. Sodium chlorate

are mixed in proportions from 1:1 to 40:1, preferably from 2:1 to 20:1.

G. Ammonium sulfamate

are mixed in proportions from 1:1 to 100:1, preferably from 1:1 to 50:1.

Other organic herbicides

The following organic herbicidal agents can be mixed with the oxazinone salts according to the invention in the quantities specified below:

A. 5,6-dihydro-(4A,6A)-dipyrido-(1,2-A,2',1'-C)

pyrazinium dibromide

are mixed in proportions from 1:20 to 16:1, preferably from 1:5 to 5:1.

B. 3-Amino-1,2,4-triazole

are mixed in proportions from 1:SO to 20:1, preferably from 1:5 to 5:1.

C. 3,6-endoxohexahydrophthalic acid

are mixed in proportions from 1:3 to 20:1, preferably from 1:2 to 10:1.

D. Hexachloroacetone

are mixed in proportions from 1:2 to 16:1, preferably from 1:1 to 8:1.

E. Diphenylacetonitrile1

N,N-dimethyl-α,α-diphenylacetamide

N,N-din-n-propyl-2,6-dinitro-4-trifluoroethylaniline N,N-di-n-propyl-2, 6-dinitro-4-tnethylaniline

are mixed in proportions from 1:10 to 30:1, preferably from 1:5 to 20:1.

F. O-(2,4-dichlorophenyl)-O-methylisopropylphosphoramidothiate

2,3,5,6-tetrachloroterephthalic acid dimethyl ester

are mixed in proportions from 1:4 to 20:1, preferably from 1:3 to 15:1.

G. 2,4-dichloro-4'-nitrodiphenyl ether

are mixed in proportions from 1:10 to 30:1, preferably from 1:5 to 20:1.

Substituted uracils

The oxazinone salts can be mixed with substituted uracils

in the quantity ratios listed below. These are all weight ratios.

A. 3-cyclohexyl-6-methyluracil

3-cyclohexyl-6-ethyluracil

3-cyclohexyl-6-sec-butyluracil

3-norborny1-6-methyluracil

3-cyclopentyl-6-methyluracil

3-cyclohexyl-6-isopropyluracil

are mixed in proportions from 1:4 to 4:1, preferably from 1:2 to 2:1.

B. 3-cyclohexy1-5,6-trimethyleneuracil

3-sec-butyl-5,6-trimethyleneuracil

3-isopropyl-5,6-trimethyluracil

3-isopropyl-5,6-tetramethyleneuracil

3-isopropyl-5,6-pentamethyleneuracil

are mixed in proportions from 1:6 to 6:1, preferably from 1:4 to 4:1.

C. 3-cyclohexyl-5-bromouracil 3-cyclohexyl-5-chlorouracil

3-isopropyl-5-bromouracil

3-sec-butyl-5-bromouracil

3-sec-butyl-5-chlorouracil

mixed in proportions from 1:6 to 6:1, preferably from 1:2 to 2:1.

D. 3-isopropyl-1-trichloromethylthio-5-bromo-6-methyluracil 3-cyclohexyl-1-trichloromethylthio-5-bromo-6-methyluracil

3-sec-butyl-1-acetyl-5-bromo-6-methyluracil

3-isopropyl-1-acetyl-5-bromo-6-methyluracil

3-isopropyl-1-trichloromethylthio-5-chloro-6-methyluracil

are mixed in proportions from 1:4 to 4:1, preferably from 1:2 to 2:1.

E. 3-sec-butyl-5-bromo-6-methyluracil

3-i isopropyl-5-bromo-6-methyluracil

3-sec-butyl-5-chloro-6-methyluracil

3-phenyl-5-bromo-6-methyluracil

3-(1,3-dimethylbutyl)-5-bromo-6-methyluracil

3-(1-ethylpropyl)-5-chloro-6-methyluracil

3-cyclohexyl-5-bromo-6-methyluracil

are mixed in proportions from 1:4 to 4:1, preferably from 1:2 to 2:1.

To further illustrate the herbicidal effect of the compounds used according to the invention, examples of preparations containing these compounds are given in the following with information regarding the herbicidal effect of the preparations.

Example 1

These substances are mixed and ground in a hammer mill until the particle size of practically all components is below 50 microns.

The wettable powder thus obtained can be used to combat annual, broad-leaved plants and grass species that grow around telephone poles and road signs. Application of 560 g of active substance per acres in approx. 150 liters of water gives a very good control of Digitaria sp., Echinochloa sp., Rudbeckia, Mollugo verticillate and Stellaria sp.

Example 2

A wettable powder is produced by mixing these substances and micropulverizing the mixture until practically all particles have a particle size below 50 microns.

This preparation can be used in a quantity of 2.24 kg per acres in 378 liters of water for weed control around oil tank facilities and on railway bodies.

A very good control of Agropyron repens, Digitaria sp., Potentilla anserina, Sorghum halepense, Hymenoxys, Chrystanthemum leucanthemum, Erigeron canadensis, Acer, Quercus and Salix is achieved.

When using 3.38 kg per decares of active ingredient for local treatment achieves very good control of such weed plants with deep rots such as Convolvulus and Cirsium arvense.

Example 3

These substances are mixed, and the mixture is micropulverized until the solids practically have a particle size below 50 microns. The mixture is then mixed again until it is homogeneous.

The thus obtained wettable powder can be used as a herbicide with a general effect on industrial sites and railway bodies. From 1.12 to 2.24 kg of active substance per acres in 378 liters of water gives a very good control of Solidago sp., Oenothera, Phytolacca americana, Chrystanthemum leucanthemum, Xanthium sp., Potentilla anserina, Digitaria sp. and Eragrostis pectinacea.

2.24 kg of active ingredient per acres in 190 liters of water gives a very good control of Cyperus.

Example 4

These ingredients are mixed, and the mixture is ground, after which it can be mixed with water for application in topical application in the form of a solution.

The preparation obtained can be used in an amount from 112 to 224 g per decares of active ingredient in 113 liters of water for post-germination control of one-year weed plants in sugar beet plantations. Crop exchange on germinating Digitaria sp., Echinochloa sp., Amaranthus sp.

(species) and Chenopodium album provide very good control of these weeds.

Example 5

This suspension in the oil is prepared by first grinding the active substance and then mixing it with the other ingredients while stirring, or by mixing all the ingredients, and then finely grinding the mixture so that the particle melting of the active ingredient is reduced. The preparation obtained is suitable for dilution with oil for spray exchange fluids. It can thus be diluted with a herbicidal oil such as e.g. "Lion Herbicidal Oil No. 6" and is applied in a quantity of 1.35 kg/acre of active ingredient for the control of weeds in general along fences around cyclones and on railway bodies.

Good control is achieved with a duration of several months. Agropyron repens, Bromus secalinus, Panicum capillare, Diodia teres and Datura stramonium are eradicated.

Example 6

These substances are mixed, and the mixture is micropulverized until the particle size of the uracil is reduced to approx. 10 microns in diameter, after which it is mixed again.

The preparation obtained gives a very good control of weed plants such as Digitaria sp., Avena fatua, Brassica kaber, wild-growing alfalfa grass, Setaria and Chenopodium album when it is applied before or after the germination of these plants in a quantity of 450 g/acre.

Example 7

The active substance and the "Celite" component are mixed and ground in a hammer mill until the mixture is uniform and the particle size of the entire material is practically below 50 microns. The obtained starch-like concentrate is mixed with the kaolinite, and the mixture is freed from agglomerates in a device such as an "Entoleter" cloth, whereby a uniform, highly flowable starch preparation is obtained.

This preparation is used to combat annual and perennial weed plants that grow in the same areas, e.g. around farm buildings. Application of approx. 1.7 kg of active material per decares provides a very good eradication of Lepidium, Brassica kaber, Arctium, Agropyron repens and Digitaria sp.

Example 8

This granulated preparation is prepared by suspending the active ingredient in acetone and spraying the obtained solution on the attapulgite granulate, while this is tumbled, after which the obtained product is filtered.

The granules can be applied by hand for "spot" treatment of unwanted grass species growing in agricultural areas. When using from 2.24 to 3.36 kg of active substance per decares, good control of Paspalum dilatatum is achieved.

Claims (1)

Herbicides, characterized in that they contain as active ingredient one or more compounds with the general formula: or salts of such compounds, in which general formula denotes an alkyl radical of 1-10 carbon atoms, or an even tually alkyl-substituted cycloalkyl-, cycloalkenyl-, bicycloalkyl-, cycloalkylalkyl-, cycloalkenylalkyl or bicycloalkylalkyl radical with 5-12 carbon atoms, a phenyl radical, or an optionally alkyl-substituted aralkyl radical with 7-10 carbon atoms, R^ denotes a hydrogen, chlorine or bromine atom , or an alkyl radical with 1-4 carbon atoms, while R 1 denotes an alkyl radical with 1-5 carbon atoms.