Stabilized liquid herbicidal composition and process for its preparation

Abstract: A stabilized liquid herbicidal composition comprising, as active ingredient, a herbicidally effective amount of phenmedipham and/or desmedipham, in which the active ingredient in a finely ground state is dispersed in an acidic liquid phase which comprises at least one oily component in an amount of 5-75% by weight, and at least one surfactant in an amount of 5-60% by weight, and optionally water. The stabilized liquid herbicidal composition will, when it is diluted with water before the final use, form an oil-in-water emulsion or a microemulsion. The herbicidal composition may be prepared directly from moist phenmedipham and/or desmedipham. The compositions are especially preferred for use in beet fields.

Description: FIELD OF THE INVENTION The present invention relates to stabilized liquid herbicidal compositions comprising phenmedipham and/or desmedipham (hereinafter called "the phenyl carbamates") and optionally metamitron, chloridazon and ethofumesate. TECHNICAL BACKGROUND British patent specification No. 1,127,050 (claiming priority from German Patent Application No. Sch. 36854 IVb/12o dated 9th April, 1965) (to Schering) discloses substituted phenylcarbamates of the general formula A in which R₁ represents an alkyl group, a cycloalkyl group or an aryl group, which aryl group may be substituted by a halogen atom and/or an alkyl group and/or a trifluoromethyl group, R₂ represents a hydrogen atom or an alkyl group, or R₁ and R₂ together with the nitrogen atom may form a heterocyclic ring that may contain further nitrogen and/or oxygen atoms and R₃ represents an alkyl, alkenyl or alkynyl group that may be substituted by a terminal halogen atom, which compounds are useful for selectively combating weeds in crop areas. The herbicidal activity is observed in both pre-emergence and post-emergence treatments, thus allowing preparations containing said compounds A to be applied by whichever method is desired. The herbicidal activity is also observed when compounds A are applied on the leaves of established weeds, and the compounds are especially useful in combating weeds in best fields, especially as post-emergence herbicides in sugar beet fields. An especially preferred compound of the general formula A is methyl (3-(3-tolyl-carbamoyloxy)phenyl)carbamate which has later been given the common name phenmedipham. Another especially preferred compound is ethyl (3-phenyl-carbamoyloxyphenyl)carbamate which has later been given the common name desmedipham. Methyl (3-(3-tolyl-carbamoyloxy)phenyl)carbamate is commercially available under the trade mark Betanal and is used especially as post-emergence herbicide for the weeding of beet crops, in particular sugar beet, at an application rate of 1 kg a.i./200-300 liters/ha. It has been reported ( Pesticide Manual , A World Compendium, The British Crop Protection Council, 6th Edition, 1979) that the compound acts through the leaves with little action via the soil and roots. In the soil there was, in three months, a 71-86% degradation of the a.i. (active ingredient) detected one day after treatment. Phenmedipham and desmedipham may be prepared by reacting the corresponding N-hydroxyphenyl carbamate and isocyanate, either in a solvent, as described in the above-mentioned British patent specification, or in water, as described in Applicant's co-pending European Application No. 84 111 244.4. After the completion of the reaction, the reaction product, which is very heavily soluble in water, may either be isolated and purified in a conventional manner, e.g., by filtration and washing with water, optionally followed by drying, or be removed from the aqueous phase by extraction with an organic solvent (or solvent mixture) which is substantially water-immiscible or miscible with water to only a minor extent. The substituted phenyl carbamates may be used either alone or in admixture with one another and/or other herbicides and/or other substances, for example fertilizers, for combating weeds. They may be used in the form or concentrated compositions for dilution with water at the site of use. In the formulation of known commercial liquid herbicidal concentrates of the substituted phenyl carbamates, it is customary to include a solvent which is capable of dissolving the phenyl carbamate and which facilitates later dilution of the composition on the location in which the composition is to be used. As already indicated above, isophorone is normally used as the solvent in the formulation of such compositions, as isophorone is a fairly good solvent for the phenyl carbamates and the phenyl carbamates are chemically relatively stable in solution in isophorone, in particular when the phenyl carbamates have been washed or treated with acid at a pH of about 2-4 prior to dissolving them in isophorone. Another advantage of the use of isophorone is that it is only slightly soluble in water (if a water-soluble solvent were used in the concentrate, it would tend to dissolve in the aqueous phase when the liquid preparation ready for application is prepared on location by addition of water, which would cause the phenyl carbamate to precipitate with a consequent decrease in its biological activity and blocking of the spraying equipment). It is customary to include ionic emulsifiers such as calcium dodecyl benzene sulfonate in commercial solutions of phenmedipham in isophorone. It has also been suggested to use salts of phosphoric acid esters as emulsifiers. As an interesting alternative to the solutions of the phenyl carbamates (phenmedipham and/or desmedipham) in isophorone, it has been found, according to the invention, that the biological activity of the substituted phenyl carbamates is advantageously high when the phenyl carbamates are "activated" by being presented in the form of suspensions of the compounds in finely ground state in liquid phases comprising one or several oily components and one or several surfactants, the liquid phase being able to form an oil-in-water emulsion or a microemulsion when mixed with water at the site of use for making the final preparation ready for use. Numerous patent specifications and literature citations constitute a mosaic which fall into two categories, i.e. (1) citations describing active compounds dissolved in an organic solvent and thereafter emulsified by means of a large variety of surfactants with water to make ready-to-use formulations to be spread on fields, and (2) citations describing active compounds dispersed in water by means of surfactants of various types. DE 33 25 444 A1 discloses stable herbicide compositions comprising phenmedipham and desmedipham dissolved in organic solvents such as cyclohexanon, isophorone, xylol. EP 0 102 003 discloses stabilized herbicide compositions based on meta-biscarbamates formulated as fluid aqueous suspensions comprising stabilizers which also serve as emulsifying and suspending agents, thickening agents and anti-bacterial or anti-fungal compounds. The mixture is ground to form a fluid suspension of fine solid particles or when a concentrated aqueous emulsion by mixing with water is prepared, stabilizing solvents are added. None of the formulations disclosed in the reference contain mineral or vegetable oil. US 4,452,630 discloses stable, heat-resistant solutions of pesticidal carbamates dissolved in organic solvents such as xylene, xylol and dimethylformamid. DE 30 40 299 A1 discloses stabilized fluid herbicidal compositions comprising desmedipham and organic solvents such as cyclohexanon, xylol, isophorone and Shellsol R. The invention relates to a stabilised liquid herbicidal composition comprising phenmedipham or desmedipham characterised in that the composition is an emulsion comprising phenmedipham and/or desmedipham dispersed in a continuous phase of an oily component, and comprises a) 5-40% by weight of phenmedipham and/or desmedipham of particle size less than 10 microns, b) 15-65% by weight of an oily component consisting of one or more mineral and/or vegetable oils, c) 10-40% by weight of a surfactant component comprising one or more surfactants, and d) up to 40% water, the composition being adapted to form a stable ready-for-use oil-in-water emulsion or micro-emulsion on dilution with water at a rate of one part of composition to 1-10 parts by volume of water. As examples of mineral oils may be mentioned spindle oil, aromatic compounds such as propylbenzene and dodecylbenzene, parafinic oils, etc., as examples of vegetable oils may be mentioned soy oil, rape seed oil, olive oil, etc. Oily components are furthermore compounds which fulfil each of the conditions that they should be liquid at normal temperatures, be immiscible with water in a ratio of 1:10-10:1 by weight, comprise at least 67% by weight of hydrocarbyl or hydrocarbylene and optionally halogen, calculated on the total chemical composition thereof, and be one in which the solubility of the substituted phenyl carbamates is less than 1% by weight. The suspensions of the phenyl carbamates in oily components and surfactants may have a content of oily substance of about 15-65% by weight, calculated on the composition. The surfactant or surfactants, which may be selected from the group consisting of non-ionic, anionic, ampholytic and cationic surfactants and mixtures thereof, will normally be present in 10-40% by weight, calculated on the composition. The amount of the phenyl carbamates may be from 5 to 40% by weight, calculated on the composition. In addition to the active compound, the oily component and the surfactant, the liquid phase of these concentrated compositions may contain one or several constituents selected from the group consisting of glycols, glycol ethers and combinations thereof, normally in concentrations of 0.1-15%, in particular 2-10%, calculated on the weight of the composition. Furthermore, water in an amount of up to 40% by weight may be incorporated. In practice, it will be considerations concerning the chemical stability of the phenyl carbamate in the individual composition which will dictate the maximum amount of water which can be added. If water is incorporated in the oil/detergent mixture, pH should be controlled into the acidic range, preferably in the optimum range of 2-4, in order to secure optimum chemical stability of the phenyl carbamate. The oily component and the surfactant may be so selected that they are mutually soluble to form a stable solution which is capable of effectively suspending finely divided phenyl carbamates and so that the surfactant will effectively emulsify the oil when water is added to form the final preparation ready for use. The surfactant may also contribute to effectively wet the sprayed surface with the preparation. The oily component and the detergent and the relative amounts thereof may also be so selected that they are capable of forming a microemulsion when mixed with an equal amount of water or up to a ten times as high amount of water (a microemulsion is characterized by comprising oil, emulsifier (surfactant) and water in a finely divided state and by being clear and translucent). A microemulsion is stable and cannot normally be separated by centrifugation). The advantage of selecting the oily component and the surfactant in such a manner that they form a microemulsion is, i.a., that the phenyl carbamates may be added to the oily component/surfactant in wet state, i.e. it is not necessary to completely dry the phenyl carbamate obtained in the synthesis process carried cut in water before it is combined with the oily component/surfactant. Another advantage of selecting the oily component and the surfactant in such a manner that they are capable of forming a microemulsion is that the microemulsion, due to its inherent stability, tends to keep the suspension of the phenyl carbamate stable during transportation and handling of the composition, thus avoiding sedimentation problems. A further advantage connected to compositions in microemulsion form is that the dilution with water for the preparation of solutions ready for use takes place without problems such as lump-forming, etc. Usable surfactants are non-ionic compounds such as polyethoxylated alkylphenoles, polyethoxylated higher alkanoles, polyethoxylated fatty acids, polyethoxylated amines and amides, monoglycerides and derivatives thereof. Alkylarylsulphonic acids and phosphoric acid esters and salts thereof will also be usable surfactants. Phosphoric acid esters may be mono- and diesters of polyethoxylated higher alkanoles, polyethoxylated alkylphenoles, polyethoxylated distyryl- and tristyrylphenoles and non-ethoxylated alcohols. Furthermore, ampholytes will be usable surfactants. Other surfactants are e.g. as described in McCutcheons publication. Detergent & Emulsifiers, International Edition, 1983, Glen Rock, New Jersey 07452, USA. Corresponding surfactants from other suppliers are, of course, also applicable. It is believed to be advantageous to use mixtures of ethoxylated surfactants and anionic surfactants, preferably a non-ionic/anionic mixture when the non-ionic components constitute a mixture of surfactants with HLB-values of about 9 (emulsifier) and about 12-13 (wetting agent and dispersing agent), respectively. In the preparation of the substituted phenyl carbamate composition, the surfactants may be mixed with the oily component yielding a translucent solution. In this solution, coarsely ground dry substituted phenyl carbamate is slurried. The mixture may be ground further, e.g. in a ball mill, yielding at least 99% of the substituted phenyl carbamate with a particle size of less than 10 micron and 50% with a particle size of less than 3-5 micron. When the substituted phenyl carbamate prepared in aqueous solution is isolated as a wet paste, the content of dry material will normally be about 65-70% after centrifugation. It is possible to use this material slurried in the oil/detergent mixture whereby the water becomes incorporated in the mixture so that the liquid phase comprises a stable microemulsion which can be further ground in the ball mill. In another embodiment, the herbicidally active compound or compounds in the form of an aqueous slurry may be ground to comminute the compound or compounds to a size suitable for being incorporated in the final composition, optionally with addition of a surfactant, whereafter the liquid comprising one or more oily components and one or more surfactants is added, or the components which when mixed would constitute said liquid are added separately. In either case, the resulting liquid phase will thereby form an emulsion or microemulsion. This is considered to be an advantageous method of utilizing the aqueous slurry obtained in the water phase synthesis described above. Minor amounts of glycol ethers, e.g. butylglycol, will presumably have an advantageous effect on the viscosity and at the same time offer the possibility of a broader mixture ratio between the microemulsion and water when the composition is to be diluted on the location in which the composition is to be used. Small amounts of water in the composition will often show a viscosity-controlling effect, and glycols such as propylene glycol will stabilize mixtures containing limited amounts of water. The dispersion must show an adequate viscosity. On the one hand, it must be so easy-running that the mixing process with the water used in the dilution proceeds quickly, but on the other hand, it must be sufficiently high-viscous to prevent sedimentation of the active ingredients. Oil-containing phenmedipham dispersions show a biological effect comparable with preparations made up with isophorone. Ranges of application of the order of about 0.3 kg of active substance per hectare have been found to be adequate for the selective combating of weeds when two or more applications are performed in the growth season, or when the active substance is sprayed via a band spraying equipment. In other instances, an application rate of about 1 kg of active substance per hectare is normally adequate. The above-described method for preparing oil-based compositions does not only apply to compositions comprising the substituted phenyl carbamates, but may also be used in the preparation of compositions also comprising other types of herbicides such as 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one (metamitron). Thus, compositions comprising both the phenyl carbamates and metamitron are advantageous in that the content of active ingredient may be kept at a lower level as the preferred phenyl carbamates are more active per weight unit than the other herbicidally active component mentioned above. The above-mentioned compound metamitron is used as a herbicide for beets, normally in a dosis of about 3-4 kg/ha. When metamitron in some cases is preferred instead of the phenyl carbamates which are used in a dosis of about 1 kg/ha only, this is due to the fact that metamitron has a better biological effect against cleavers goosegrass ( Galium aparine ), nippelwort ( Lapsana communis ) and black nightshade ( Solanum nigrum ). A much better biological effect is obtained in the combating of corn marigold ( Chrysanthemum segetum ), wild chamomile ( Matricaria chamomilla ), small nettle ( Urtica urens ) and anual meadow grass ( Poa annua ). The other 15-20 weed species in beets which are common in Denmark are combated equally well with phenmedipham and metamitron. To this should be added that metamitron in a dosage of 3-4 kg/ha is less aggressive (phytotoxic) to the beet plants than phenmedipham used in a dosis of 1 kg/ha. Farmers often prefer to use a mixture of metamitron and phenmedipham in which each of the preparations is used in a dosage which is half of the usual dosage. In this way, a biological effect which is fully up to what may be obtained when using metamitron alone is obtained. Nor is the herbicidal mixture more phytotoxic than when metamitron is used alone. Metamitron is normally commercially available as a 70% wettable powder and phenmedipham as a 16% emulsion composition containing isophorone. Up till now, the farmers have themselves mixed the compositions in connection with the spraying. It is, however, not practical for the user to mix two types of compositions which are so different. The mixing is best performed by diluting each composition separately in part of the dilution water and then performing the mixing. In order to activate the metamitron biologically, mineral oil is often added which oil is emulgated into the spraying solution. Thus, there will be a risk of spraying problems (nozzle stops) if the mixing is not performed carefully. When using several products, there will be a larger risk of wrongly apportioning the products. Finally, when using the present product which is characterized in that both phenmedipham and metamitron are dispersed in an oil/surfactant mixture, it is achieved that the user - contrary to the practice existing up till now - totally avoids dust from the wettable powder, and that isophorone is not used as the solvent. Thus, an interesting aspect of the invention is a composition comprising phenmedipham or desmedipham in an amount of about 6% by weight, metamitron in an amount of 5-40%, preferably 10-30%, e.g. about 17% by weight, formulated with an oily component such as mineral oil, e.g. spindle oil, in an amount of about 30% by weight, a surfactant or surfactant mixture comprising ethoxylated nonyl phenol (3-9 ethylene oxide units per molecule) and optionally a phosphoric acid ester salt such as Berol™ 724, monoethanolamine salt, and/or an alkyl or aryl or alkylaryl sulphonic acid salt, such as dodecyl benzene sulphonic acid triethanolamine salt or a linear alkyl (C₁₀-C₂₂) sulphonic acid salt (LAS), the total amount of surfactant or surfactant mixture being about 40% by weight, butyl glycol in an amount of 0-10%, e.g. about 7.5% by weight, and optionally water, all amounts calculated on the total composition. A mixed composition may be prepared by mixing a dispersion comprising phenmedipham and a dispersion comprising metamitron, which dispersion may be prepared individually in liquid phases comprising an oily component such as spindle oil in an amount or about 30-35%, a surfactant mixture consisting or an alkyl or aryl or alkylaryl sulphonic acid salt such as dodecyl benzene sulphonic acid - triethanolamine salt, ethoxylated nonyl phenol and butyl glycol. The solubility of phenmedipham and metamitron in mineral oil is about 0.1%, depending on the content of aromatics in the oil. In the above-described water-emulsifiable liquids which are solutions comprising oil and surfactant, the solubility of phenmedipham and metamitron is about 3% when the content of surfactant in the liquid is of the same order as the content of oil. However, at such a high solubility, there may be a tendency of slow crystal growth of phenmedipham and/or metamitron in the dispersions during storage under varying temperature conditions, which means that the compositions will be less stable under such conditions. In microemulsions with a content of about 25% of water, the solubility of phenmedipham is reduced by a factor of 10 to about 0.3%. A similar reduction does not take place for metamitron. In addition, it tends to be more time-consuming to dilute metamitron dispersions in water than phenmedipham dispersions, probably because of the dissolved proportion of metamitron. However, once emulsions or microemulsions have been formed in the dilution, they are very stable. To lower the solubility of phenmedipham and metamitron in the liquid and to counteract the tendency for metamitron compositions to be more time-consuming to dilute with water, the proportion of oil in the liquid may be kept high and the proportion of surfactant correspondingly low, and an oil may be used which has a limited content of aromatics, that is, a content of less than 30% by weight, preferably less than 10% by weight. (As an example of a preferred oil for this purpose may be mentioned a mineral oil having a boiling point above 200°C and a viscosity of less than 100 cSt at 40°C and, as mentioned above, a content of aromatics or less than 30% by weight, preferably less than 10% by weight.) However, it has been found that if the amount of oil is increased to about 60% and the amount of surfactant is reduced to about 10-15%, there will be a pronounced tendency for the composition to separate sticky sediments of oil and fine-grained herbicide when the composition is diluted with water. Also, the proportion of oil which is emulsified into the water phase will tend to separate again as an upper phase. Thus, in compositions with a high amount of oil which has a low content of aromatics, there is a pronounced necessity for the use of a highly efficient emulsifier (surfactant) system. A sufficiently efficient emulsifier (surfactant) which will secure a satisfactory emulsifiability of the mineral oils with relatively low content of aromatics may for example be obtained by replacing part of the above-mentioned ethoxylated nonylphenols with ethoxylated dinonylphenols and combining them with either phosphoric acid ester salts such as Berol™ 724 monoethanolamine salt and/or an alkyl or aryl or alkylaryl sulphonic acid ester salt such as dodecyl benzene sulfonic acid triethanolamine salt, the total amount of surfactant being about 10-15%, calculated on the composition, and the count of mineral oil of low aromatics content, e.g. solvent-refined paraffinic mineral oil in an amount of about 60% by weight. Part of the oil may be replaced with a lower boiling petroleum fraction such as kerosene. Thus, interesting compositions according to the invention comprise 15-40, preferably 20-30% by weight of either phenmedipham or a combination of phenmedipham and metamitron dispersed in a liquid phase which contains a mineral oil in an amount of about 60% by weight, a surfactant or surfactant mixture comprising ethoxylated alkylphenol (containing 3-9 ethylene oxide units) in which the alkyl group contains 4-15, in particular 6-12 carbon atoms, and/or ethoxylated dialkylphenol (containing 4-14 ethylene oxide units) in which the alkyl group contains 4-15, in particular 6-12 carbon atoms, and optionally a phosphoric acid ester salt and/or an alkyl or aryl or alkylaryl sulphonic acid salt, the total amount of surfactant or surfactant mixture being 10-15%, by weight. The mineral oil may, e.g., be solvent-refined mineral oil in an amount of about 50% combined with aromatics-free kerosene (boiling point 190-240°C) in an amount of about 10%, the ethoxylated dinonylphenol (containing 9 ethylene oxide units) may, e.g., be present in an amount of about 5%, the ethoxylated nonylphenol (containing 4 ethylene oxide units) may, e.g., be present in an amount of about 3% and phosphoric acid ester (Berol™ 724) monoethanolamine salt may, e.g., be present in an amount of about 5%. The amount of dispersed phenmedipham should preferably constitute 20-40%, more preferably 25-35% of the composition, and the amount of dispersed metamitron should preferably constitute 15-35%, more preferably 20-30% of the composition. Combined compositions may be prepared by mixing phenmedipham and metamitron dispersions. The dispersions prepared in this manner are easy to dilute with water. Both phenmedipham and metamitron are dispersed satisfactorily, and the oily phase forms sufficiently stable emulsions in the water. In these oil-detergent mixtures, the solubility of phenmedipham and metamitron is about 0.2%. The compositions are preferably substantially free from water which increases the chemical stability of the active substances. EXAMPLE 1 Phenmedipham dispersions comprising an oil-based microemulsion or solution as the liquid phase Microemulsions I and III and a solution II were prepared without phenmedipham by mixing the constituents. Then, one part by weight of phenmedipham (technical grade, 96%) was incorporated into 3 parts by weight of the liquid phase in each of I, II and III, and each of the resulting mixtures was ground in a ball mill charged with glass balls ( 1 mm). Turbidity temperatures for the microemulsions I and III and the solution II and the appearance of microemulsions formed therefrom upon addition of tap water are stated in Table 1. It will be noted that they all appear as homogeneous liquids which do not separate into their components. After standing for 3 weeks at 45-50°C, all of the phenmedipham-containing dispersions were uniform after moderate shaking. EXAMPLE 2 Phenmedipham and metamitron dispersions comprising an oil-based solutton as the liquid phase Dispersions I and II with the contents as stated below were prepared in the same manner as described in Example 1. Ingredients Dispersion I Dispersion II Triethanolamine 2.6% 2.5% Sulfosoft™ 5.9% 5.7% Spindle oil 29.3% 28.4% Marlophen™ 88H 19.1% 18.5% Berol™ 26 13.2% 12.8% Butyl glycol 7.4% 7.1% 77.5% 75.0% Metamitron, Tech. grade, 98% 22.5% Phenmedipham, Tech. grade, 96% 25.0% pH of dispersion (in a 1:10 dilution with water) 3-4 3-4 A combined composition consisting of 75% by weight of dispersion I and 25% by weight of dispersion II was prepared by mixing the dispersions. The composition formed was a viscous composition containing about 6% of phenmedipham and about 17% of metamitron which could be diluted with water by somewhat prolonged mixing and resulted in stable dispersions. EXAMPLE 3 Metamitron dispersion comprising an oil-based solution as the liquid phase Solutions I and II were prepared by mixing, and one part by weight of metamitron (technical grade, 98%) was incorporated into 3 parts by weight of the liquid phase in each of I and II, and each of the resulting mixtures was ground in a ball mill charged with glass balls ( 1 mm). Turbidity temperatures for the resulting solutions I and II and the appearance of the microemulsions formed upon addition of tap water to the solutions are stated in Table 2. It will be noted that they all appear as homogeneous liquids which do not separate into their components. EXAMPLE 4 Metamitron and phenmedipham dispersions comprising an oil-based solution as the liquid phase Dispersions I and II with the contents as stated in Table 3 were prepared in the same manner us described in Example 1. When mixed with water, the oil-containing liquid phases do not form stable transparent microemulsions as described in the preceding examples, but rather form conventional emulsions which, however, precipitate oil only very slowly. The tendency to separate sediments of oil which contain fine-grained metamitron or phenmedipham, respectively, is negligible. A combined composition of 77.5% by weight of dispersion I and 22.5% by weight of dispersion II was prepared by mixing the dispersions. The composition contained about 19% of metamitron and 6.5% of phenmedipham. Dispersion I (metamitron) and the mixed dispersion mentioned above are both thixotropic. Although they seem somewhat viscous, they are easily mixed (emulsified and dispersed) in 98-95% of water. The mixing is made easier because the density of the dispersions are less than that of water.

Claims: Claims for the following Contracting States : BE, DE, FR, GB, IT, NL, SE A stabilised liquid herbicidal composition comprising phenmedipham or desmedipham characterised in that the composition is an emulsion comprising phenmedipham and/or desmedipham dispersed in a continuous phase of an oily component, and comprises a) 5-40% by weight of phenmedipham and/or desmedipham of particle size less than 10 µm, b) 15-65% by weight of an oily component consisting of one or more mineral and/or vegetable oils, c) 10-40% by weight of a surfactant component comprising one or more surfactants, and d) up to 40% water, the composition being adapted to form a stable ready-for-use oil-in-water emulsion or micro-emulsion on dilution with water at a rate of one part of composition to 1-10 parts by volume of water. A herbicidal composition according to claim 1 wherein at least 50% of the phenmedipham and/or desmedipham is of a particle size of 3 to 5 µm. A herbicidal composition according to either of claims 1 or 2 containing water wherein the liquid phase is acidic. A composition according to claim 3 wherein the liquid phase has pH of 2-4. A composition according to any of claims 1 to 4 further comprising one or more further herbicides selected from metamitron, chloridazon and ethofumesate. A process for the preparation of a herbicidal composition according to any of claims 1-5 in which phenmedipham and/or desmedipham is mixed with the other components of the composition, and the mixture subjected to grinding or milling to disperse the phenmedipham and/or desmedipham into a continuous phase of the oily component. A process for the preparation of a herbicidal composition according to any of claims 1-5 wherein the phenmedipham and/or desmedipham in the form of an aqueous slurry is comminuted such that the phenmedipham and/or desmedipham has a particle size of less than 10 µm, and the slurry is mixed with the other components to form an emulsion. A method for combating weeds which comprises applying a composition according to any of claims 1-5 to a locus where weeds are growing or are anticipated to grow. A method for controlling weeds in beet according to claim 8. Claims for the following Contracting State : AT A process for the preparation of a stabilised liquid herbicidal composition comprising phenmedipham or desmedipham characterised in that the composition is an emulsion comprising phenmedipham and/or desmedipham dispersed in a continuous phase of an oily component, and comprises a) 5-40% by weight of phenmedipham and/or desmedipham of particle size less than 10 µm , b) 15-65% by weight of an oily component consisting of one or more mineral and/or vegetable oils, c) 10-40% by weight of a surfactant component comprising one or more surfactants, and d) up to 40% water, the composition being adapted to form a stable ready-for-use oil-in-water emulsion or micro-emulsion on dilution with water at a rate of one part of composition to 1-10 parts by volume of water. A process according to claim 1 wherein at least 50% of the phenmedipham and/or desmedipham is of a particle size of 3 to 5 µm. A process according to either of claims 1 or 2 containing water wherein the liquid phase is acidic. A process according to claim 3 wherein the liquid phase has pH of 2-4. A process according to any of claims 1 to 4 further comprising one or more further herbicides selected from metamitron, chloridazon and ethofumesate. A process for the preparation of a herbicidal composition according to any of claims 1-5 in which phenmedipham and/or desmedipham is mixed with the other components of the composition, and the mixture subjected to grinding or milling to disperse the phenmedipham and/or desmedipham into a continuous phase of the oily component. A process for the preparation of a herbicidal composition according to any of claims 1-5 wherein the phenmedipham and/or desmedipham in the form of an aqueous slurry is comminuted such that the phenmedipham and/or desmedipham has a particle size of less than 10 µm, and the slurry is mixed with the other components to form an emulsion. A method for combating weeds which comprises applying a composition according to any of claims 1-5 to a locus where weeds are growing or are anticipated to grow. A method for controlling weeds in beet according to claim 8.

Inventors: NIELSEN ERIK, NIELSEN, ERIK
Applicants: BEROL NOBEL SUISSE, BEROL NOBEL (SUISSE) S.A.
Application year: 1987
Main classification: A01N25
IPC codes: A01N43, A01N47, C07C269, A01N37