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WO2025061719A1 - Emulsion in water concentrate comprising glufosinate, vlcfa inhibitor and specific surfactants - Google Patents

Emulsion in water concentrate comprising glufosinate, vlcfa inhibitor and specific surfactants Download PDF

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Publication number
WO2025061719A1
WO2025061719A1 PCT/EP2024/076014 EP2024076014W WO2025061719A1 WO 2025061719 A1 WO2025061719 A1 WO 2025061719A1 EP 2024076014 W EP2024076014 W EP 2024076014W WO 2025061719 A1 WO2025061719 A1 WO 2025061719A1
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Prior art keywords
preferentially
glufosinate
composition
chosen
weight
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PCT/EP2024/076014
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French (fr)
Inventor
Monique Adamy
Mélanie MUGNIER
David Thomas
Claude Taranta
Marcel Patrik KIENLE
Katja Marxer
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BASF SE
Specialty Operations France SAS
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BASF SE
Specialty Operations France SAS
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Publication of WO2025061719A1 publication Critical patent/WO2025061719A1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

Definitions

  • the present invention relates to a composition, preferably for agricultural use, in the form of an emulsion in water concentrate (EW), comprising glufosinate or L- glufosinate, a VLCFA inhibitor and a combination of specific surfactants.
  • EW emulsion in water concentrate
  • the invention also relates to a method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition onto 10 soils or plants.
  • Pesticides are widely employed in agricultural pest management. Given their extensive use, there is a constant need to develop methods that can enhance the effectiveness of pesticides.
  • Agrochemical formulations can be developed in various ways, primarily based on the physical and chemical characteristics of the active ingredients.
  • Such formulations include aqueous solutions, emulsifiable concentrates, encapsulated 25 suspensions, wettable powders, oil-in-water or water-in-oil emulsions, suspoemulsions, suspo-solutions, microemulsions, emulsions, ZC formulations, and granules.
  • Herbicide formulations based on glufosinate are well known. Glufosinate is a non-selective foliage application type contact herbicide which kills or controls many 30 species of weeds.
  • glufosinate is used in burn-down segments, and for control of a wide range of broad-leaved weeds and grasses and sedges in cereals, cotton, corn and soy, fruit orchards, vineyards, rubber and oil palm plantations, ornamental trees and bushes, non-crop land, and pre-emergence in vegetables.
  • Glufosinate being a water-soluble active ingredient, it is preferably formulated as 35 aqueous solutions along with incorporation of water-soluble ingredients/adjuvants.
  • the use of one or more specific adjuvants in glufosinate-based formulation is known.
  • pesticide formulations in the form of emulsions do not give complete satisfaction in terms of stability and viscosity.
  • the aqueous continuous phase does not exhibit high ionic strength characteristics, with significant content of salts or ionic ingredients such as glufosinate ammonium salt. It is particularly challenging to stabilize an emulsion displaying high ionic strength, electrolyte-rich characteristics in its continuous phase.
  • glufosinate-based 30 compositions for agricultural needs, in particular glufosinate-based compositions with good intrinsic properties, in particular good physicochemical properties such as a good stability on storage and an adequate viscosity profile (good pourability).
  • Such compositions should generate good performances at dilution including a good homogeneity of the emulsion and/or dispersion of possible water-insoluble agricultural 35 materials, even for high loading formulations.
  • a subject-matter of which is a composition, preferably for agricultural use, in the form of an oil-in-water emulsion (EW) comprising: 5 (i) at least one first herbicide chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof, (ii) at least one second herbicide chosen from dimethenamid, dimethenamid-P, or mixtures thereof, (iii) at least one anionic surfactant, and 10 (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b.
  • EW oil-in-water emulsion
  • M surfactant mixture
  • compositions according to the invention present good intrinsic physicochemical properties.
  • compositions according to the invention 20 advantageously guarantee good performances at dilution including a good homogeneity of the emulsion and/or dispersion of water-insoluble agricultural materials when present in the composition, generally even for high loading formulations.
  • the compositions according to the invention have 25 an adequate viscosity profile and a good pourability, which allows easier application onto soils or plants.
  • compositions according to the invention advantageously show: 30 - a good stability upon storage, in particular at room temperature (20°C), or even at high temperature such as during 2 weeks at 54°C; - suitable characteristics upon dilution in water at the targeted use rate; - an adequate viscosity profile and a good pourability; - satisfying tank mix compatibility properties; and/or 35 - excellent biological efficacy.
  • a stable composition may be defined as a composition showing no sign of destabilization such as phase separation, syneresis, flocculation, sedimentation, creaming, presence of macroscopic oil droplets at the surface of the sample.
  • a stable composition is advantageously a formulation that do not show any 5 sign of destabilization as described above after the considered period of storage at the considered temperature. It has been challenging to achieve a concentrated pesticide formulation in the form of an oil-in-water emulsion, having suitable rheological characteristics. In order to achieve a good storage stability of such concentrated oil-in-water emulsion, the use 10 of a rheological agent bringing suspension properties is frequently used, such as xanthan gum or precipitated or precipitated or fumed silica.
  • the compositions according to the invention can preferably guarantee good performances at dilution, even for high loading formulations, and avoid/retard the appearance of crystals, even under rigorous conditions.
  • the composition is an agrochemical formulation with a high concentration of agricultural material(s).
  • the use of concentrated formulations is in particular advantageous for economic reasons (indeed such compositions making it possible to reduce the total weight of the formulations, and consequently their transport costs), the concentrated formulation 30 then being generally diluted to the desired concentration before application in the field.
  • a subject-matter of the invention is also a method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition onto soils and/or plants.
  • alkylaryl means an aryl group substituted with one or more alkyl 20 groups, preferably with one or more (C1-C6)alkyl groups, such as, for example, phenylmethyl or phenylethyl.
  • arylalkylaryl means an aryl group linked to at least one alkyl group of an alkylaryl group, such as a tristyrylphenyl group.
  • the aryl group is linked to at least one (C1-C6)alkyl group of an alkylaryl group.
  • oxyalkylenated compound polyoxyalkylene compound or “alkoxylated compound” is meant a compound comprising ethylene oxide groups and/or propylene oxide groups and/or glycerol groups; preferably the number of ethylene oxide and/or propylene oxide groups may range from 1 to 150, and the number of glycerol groups may range from 0 to 30; more preferentially the oxyalkylenated 30 compound does not comprise any glycerol group; - the term "plants” as used herein also includes the plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait; - the term “agronomically acceptable salts” refers to salts prepared from 35 agronomically acceptable non-toxic bases or acids including inorganic or organic bases and inorganic or organic acids.
  • Typical agronomically acceptable salts the compound referred to herein comprise an anion derived from the compound, for example, by deprotonation of a hydroxy or hydroxyalkyl substituent, and one or more positively charged counterions.
  • Suitable positively charged counterions include inorganic cations 5 and organic cations, such as for example, sodium cations, potassium cations, calcium cations, magnesium cations, isopropylamine cations, triethanolamine cations, ammonium cations, and tetraalkylammonium cations.
  • First herbicide 10 The composition according to the invention comprises at least one first herbicide (i) chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof.
  • Glufosinate (CAS Reg. No.51276-47-2), with IUPAC-Name (2RS)-2-amino-15 4-[hydroxy(methyl)phosphinoyl]butyric acid, or 4-[hydroxy(methyl)phosphinoyl]- DL-homoalanine) or DL-4-[hydroxyl(methyl)phosphinoyl]-DL-homoalaninate, is known, as well as agronomically acceptable salts thereof, in particular glufosinate- ammonium (IUPAC-Name: ammonium (2RS)-2-amino-4- (methylphosphinato)butyric acid, CAS Reg. No.77182-82-2).
  • Glufosinate is represented by the following structure (I): 30
  • the compound of formula (I) is a racemate.
  • Glufosinate is a racemate of two enantiomers, out of which only one shows sufficient herbicidal activity (see e.g. US 4265654 and JP92448/83).
  • the mixtures known in the art do not point at the stereochemistry, meaning that the 5 racemate is present (e.g. WO 2003024221, WO2011104213, WO 2016113334, WO 2009141367).
  • glucose typically comprises, in one embodiment of the invention, about 50% by weight of the L-enantiomer and 10 about 50% by weight of the D-enantiomer; and in another embodiment of the invention, more than 70% by weight of the L-enantiomer; preferably more than 80% by weight of the L-enantiomer; more preferably more than 90% of the L-enantiomer, most preferably more than 95% of the L-enantiomer.
  • the L-enantiomer of glufosinate is also referred to as glufosinate-P. 15 Glufosinate in the form of its racemate, and its salts as well as formulations thereof, are commercially available, e.g.
  • the first herbicide compound is selected from racemic 20 glufosinate mixtures as described above, wherein the glufosinate comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer.
  • the first herbicide compound is glufosinate, wherein at least 70% by weight of the glufosinate is L-glufosinate or a salt thereof. 25 L-glufosinate, with IUPAC-Name (2S)-2-amino-4- [hydroxy(methyl)phosphinoyl]butyric acid (CAS Reg. No.
  • L-Glufosinate as used in the present invention comprises more than 70% by weight of the L-enantiomer; preferably more than 80% by weight of the L-enantiomer; more preferably more than 90% of the L-enantiomer, most preferably more than 95% of the L-enantiomer and can be prepared as referred to above.
  • the salts of glufosinate or L-glufosinate are the sodium, potassium or ammonium (NH4 + ) salts of glufosinate or L-glufosinate, in particular glufosinate-P- ammonium (IUPAC-Name: ammonium (2S)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.73777-50-1), glufosinate-P-sodium (IUPAC-Name: sodium (2S)- 2-amino-4-(methylphosphinato)butyric acid; CAS Reg. No.
  • the first herbicide compound comprises a glufosinate salt, which is selected from the group consisting of the sodium, potassium or ammonium (NH4 + ) salts of glufosinate.
  • the first herbicide compound preferably comprises or is L-glufosinate- ammonium or L-glufosinate-sodium or L-glufosinate-potassium and L-glufosinate as free acid.
  • L-glufosinate-ammonium i.e. the ammonium (NH4 + ) salt of glufosinate.
  • the first herbicide compound is a L- glufosinate salt, which is in particular selected from the group consisting of the sodium, potassium and ammonium (NH4 + ) salts of L-glufosinate.
  • the first herbicide compound is a L-glufosinate salt, which is selected from the group consisting of glufosinate-P-ammonium, glufosinate-P-sodium and glufosinate-P- potassium.
  • the first herbicide compound is an ammonium salt of L- glufosinate.
  • suitable compounds of formula (I) I.1: enantiopure L-glufosinate I.1.a: enantiopure L-glufosinate-ammonium I.1.b: enantiopure L-glufosinate-sodium I.1.c: enantiopure L-glufosinate-potassium
  • I.2 mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ⁇ 95 and Y ⁇ 5 % and wherein X + Y are 100.
  • I.2.a mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ⁇ 95 and Y ⁇ 5 and wherein X + Y are 100.
  • I.2.b mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ⁇ 95 and Y ⁇ 5 and wherein X + Y are 100.
  • I.2.c mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ⁇ 95 and Y ⁇ 5 and wherein X + Y are 100.
  • I.3 mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ⁇ 90 and Y ⁇ 10 and wherein X + Y are 100.
  • I.3.a mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- 10 glufosinate-ammonium, wherein X ⁇ 90 and Y ⁇ 10 and wherein X + Y are 100.
  • I.3.b mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ⁇ 90 and Y ⁇ 10 and wherein X + Y are 100.
  • I.3.c mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ⁇ 90 and Y ⁇ 10 and wherein X + Y are 100.
  • I.4 mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ⁇ 80 and Y ⁇ 20 and wherein X + Y are 100.
  • I.4.a mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ⁇ 80 and Y ⁇ 20 and wherein X + Y are 100.
  • I.4.b mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- 20 sodium, wherein X ⁇ 80 and Y ⁇ 20 and wherein X + Y are 100.
  • I.4.c mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ⁇ 80 and Y ⁇ 20 and wherein X + Y are 100.
  • I.5 mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ⁇ 70 and Y ⁇ 30 and wherein X + Y are 100.
  • I.5.a mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ⁇ 70 and Y ⁇ 30 and wherein X + Y are 100.
  • I.5.b mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ⁇ 70 and Y ⁇ 30 and wherein X + Y are 100.
  • the first herbicide(s) (i) are chosen from L-glufosinate or an agronomically acceptable salt thereof.
  • the first herbicide(s) (i) is water-soluble, and/or comprised in the aqueous phase of the composition according to the invention.
  • the total amount of the first herbicide(s) (i) is from 10 to 600 g/L 5 (gram of first herbicide(s) (i) per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 200 g/L, relative to the total amount of the composition.
  • the total amount of glufosinate is from 10 to 600 g/L (gram of glufosinate per liter of composition), more preferentially from 50 to 500 g/L, even 10 more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 200 g/L, relative to the total amount of the composition.
  • the total amount of L-glufosinate is from 10 to 600 g/L (gram of glufosinate per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better 15 from 100 to 200 g/L, relative to the total amount of the composition.
  • the total content of the first herbicide(s) (i) ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the 20 total weight of the composition.
  • the total content of glufosinate ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the total weight of the composition.
  • the total content of L-glufosinate ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises at least one second herbicide (ii) chosen from dimethenamid, dimethenamid-P, or mixtures thereof.
  • the second herbicide(s) (ii) are Very-Long-Chain Fatty Acids (VLCFA) inhibitors.
  • VLCFA Very-Long-Chain Fatty Acids
  • Herbicides that act by inhibiting the biosynthesis of very-long-chain fatty acids have been used to control grass weeds in major crops throughout the world for the past 60 years.
  • VLCFA-inhibiting herbicides are generally highly selective in crops, 5 induce similar symptoms in susceptible grasses and can be found within the herbicide groups classified by the HRAC as K3 and N. Dimethenamid (CAS Reg. No. 87674-68-8), with IUPAC-Name (RS)-2- chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide is known.
  • dimethenamid has been described by J. Harr et al., Proc. Br. Crop Prot. Conf. – Weeds 1991, 87-92 and A. Rahman, T. K. James, Proc.45th N. Z. Plant Prot. Conf.1992, 84-88. Dimethenamid in the form of its racemate, is commercially available, e.g. under the trade-names Pestanal ® by Merck. 15 Dimethenamid is represented by the following structure (II): The compound of formula (II) is a racemate. Dimethenamid-P (CAS Reg.
  • Dimethenamid-P has been described by T. Guillet et al., Phytom 546, 50-53 (2002). Dimethenamid-P is commercially available, e.g. under the trade-names Isard ® or Outlook ® by BASF. 25 Dimethenamid-P is represented by the following structure (III): Preferably, the composition comprises dimethenamid-P.
  • the second herbicide(s) (ii) is water-insoluble, and/or comprised in the oily phase of the composition according to the invention.
  • the total amount of second herbicide(s) (ii) is from 10 to 600 g/L (gram of second herbicide(s) (ii) per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 10 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition.
  • the total amount of dimethenamid is from 10 to 600 g/L (gram of dimethenamid per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition.
  • the total amount of dimethenamid-P is from 10 to 600 g/L (gram of dimethenamid-P per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition.
  • the total content of second herbicide(s) (ii) ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition.
  • the total content of dimethenamid ranges from 1% to 50% by 25 weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition.
  • the total content of dimethenamid-P ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 30 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition.
  • the weight ratio of the total amount of first herbicide(s) (i) to the total amount of second herbicide(s) (ii) ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1.
  • the weight ratio of the total amount of glufosinate to the total amount of dimethenamid ranges from 0.1 to 5; more preferably from 0.125 to 4; more 5 preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1.
  • the weight ratio of the total amount of glufosinate to the total amount of dimethenamid-P ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 10 1.5, and even better from 0.5 to 1.
  • the weight ratio of the total amount of L-glufosinate to the total amount of dimethenamid ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1.
  • the weight ratio of the total amount of L-glufosinate to the total amount of dimethenamid-P ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1.
  • the anionic surfactant (iii) comprises at least one anionic surfactant (iii).
  • anionic surfactant is understood to mean a surfactant comprising, 25 as ionic or ionizable groups, only anionic groups.
  • an entity is described as being "anionic" when it possesses at least one permanent negative charge or when it can be ionized to give a negatively charged entity, under the conditions of use of the composition of the invention (medium or pH, for example), and not comprising a cationic charge.
  • the anionic surfactants (iii) are adjuvants, which can be chosen from sulfate, sulfonate and carboxylic (or carboxylate) surfactants. Very obviously, a mixture of these surfactants can be employed.
  • the carboxylate anionic surfactants comprise at least one carboxyl or carboxylate (-COOH or -COO-) functional group and can optionally additionally comprise one or more sulfate and/or sulfonate functional groups;
  • - the sulfonate anionic surfactants comprise at least one sulfonate (-SO3H or - SO3 – ) functional group and can optionally additionally comprise one or more sulfate functional groups, but do not comprise a carboxylate functional group;
  • - the sulfate anionic surfactants comprise at least one sulfate functional group but do not comprise a carboxylate or sulfonate functional group.
  • anionic surfactants By way of examples of anionic surfactants, mention may be made without any intended limitation thereto, of: - alkylsulfonic acids, arylsulfonic acids, optionally substituted with one or more hydrocarbon groups, and the acid function of which is partly or totally salified, like C8-C50 alkylsulfonic acids, more particularly C8-C30, preferably C10-C22 alkylsulfonic acids, benzenesulfonic acids, naphthalenesulfonic acids, substituted with one to three C1-C30, preferably C4-C16 alkyl and/or C2-C30, preferably C4-C16 alkenyl groups, - mono- or di-esters of alkylsulfosuccinic acids, of which the linear or branched alkyl portion is optionally substituted with one or more linear or branched C2-C4 hydroxylated and/or oxyalkylenated (preferably ethoxylated,
  • phosphate ester groups comprise at least one phosphate ester group, mono- or di-esterified such that it is possible to have one or two free or partly or totally salified groups.
  • the preferred phosphate esters are of the type of the mono- and di-esters of phosphoric acid and of oxyalkylenated (ethoxylated and/or propoxylated) mono-, di- or tri- styrylphenol, or oxyalkylenated (ethoxylated and/or propoxylated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; of phosphoric acid and of an oxyalkylenated (ethoxylated or ethopropoxylated) C8-C30, preferably C10-C22 alcohol; of phosphoric acid and of a non-oxyalkylenated C8-C22, preferably C10- C22 alcohol, - sulfate esters obtained from saturated or aromatic alcohols optionally substituted with
  • sulfate esters more particularly obtained from saturated or unsaturated C8-C20 alcohols, which may comprise 1 to 8 oxyalkylenated (ethoxylated, propoxylated, ethopropoxylated) units ; sulfate esters obtained from oxyalkylenated phenol, substituted with 1 to 3 saturated or unsaturated C2-C30 hydroxycarbon groups, and in which the number of oxyalkylenated units is comprised between 2 and 40 ; the sulfate esters obtained from oxyalkylenated mono-, di- or tri-styrylphenol in which the number of oxyalkylenated units varies from 2 to 40.
  • the anionic surfactants may be in the acid form (they are potentially anionic), or in a partly or totally salified form with one counter-ion.
  • the counter-ion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or moreover even an ammonium ion of formula N(R)4 + in which the R groups, either identical or different, represent a hydrogen atom or a C1-C4 alkyl group optionally substituted with an oxygen atom.
  • the anionic surfactant(s) (iii) are chosen from sulfate anionic surfactants.
  • the sulfate anionic surfactants that may be used comprise at least one sulfate (-OSO3H or -OSO3-) functional group.
  • the sulfate anionic surfactants can be chosen from the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates; and also the salts of these compounds.
  • the alkyl groups of these compounds comprising from 6 to 30 carbon atoms, in particular from 8 to 28, better still from 10 to 24, indeed even from 12 to 22, carbon atoms; the aryl group preferably denoting a phenyl or benzyl group.
  • anionic surfactant(s) (iii) are chosen from alkyl ether sulfates.
  • the anionic surfactant(s) (iii) are chosen from those of formula (IV): [R-O-(A-O)n-SO3]- M + (IV) in + which M is a cation;
  • A is C2-C3 alkandiyl;
  • R is selected from linear or branched C 10 -C 20 alkyl, preferably C 12 -C 14 alkyl, and mixtures thereof; and
  • n is a natural positive number of 1 to 12 where the number average of n is in the range of 1 to 10.
  • the compound of formula (IV) is an alkyl ether sulfate salt having C 10 -C 20 - alkyl as alkyl rest, a linker -(A-O) n - formed by 1 to 12, on average 1 to 10, C 2 -C 3 - alkylene oxide unit(s) A-O between C 10 -C 20 -alkyl and sulfate group, and a cation M + as counterion.
  • C 10 -C 20 -alkyl refers to linear or branched saturated alkyl radicals generally having from 10 to 20 carbon atoms (C 10 - C 20 -alkyl), in particular 12 to 18 carbon atoms (C 12 -C 18 -alkyl).
  • C 10 -C 20 -alkyl examples include, but are not limited to decanyl, isodecyl, 2-propylheptyl, undecanyl, dodecyl, tridecyl, isotridecyl, tetramethylnonyl, ethyldimethylnonyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, including the linear isomers, such as n-decanyl, n-undecyl, n- dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- octadecyl, n-nonade
  • R is C12-C14.
  • C2-C3-alkylene and C2-C3-alkandiyl are used synonymously 5 and refer to linear or branched divalent alkyl radicals having from 2 or 3 carbon atoms, such as 1,2-ethanediyl and 1,2-propanediyl. Preferred is 1,2-ethanediyl.
  • the variable n in the formula (IV) is natural positive number of 1 to 10, in particular in the range of 1 to 8, especially in the range of 1 to 7, i. e. n is 1, 2, 3, 4, 5, 6 or 7.
  • the compound of the formula (IV) is typically a mixture of compounds with 10 different n.
  • n is typically in the range of 1 to 10, in particular in the range of 1 to 8, preferably in the range of 1 to 7, more preferably in the range of 1 to 6, even more preferably in the range of 1 to 5, still more preferably in the range of 1.5 to 5.
  • Any reference to average of n refers to the number average of the repeating units A-O per molecule, i. e. to the relative molar amounts of repeating units A-O with 15 respect to R, i. e. the average is the number average.
  • the radicals R may be identical, i. e. all molecules or at least 95 mol-% of the molecules of the formula (IV) have the same group R.
  • the radicals R may be different, i.e. the compounds of the formula (IV) are mixtures of compounds having different radicals 20 R.
  • the difference of R may result from different isomers of the respective radical R having the same number of carbon atoms or from differences in the number of carbon atoms in the radical R or from both.
  • the radical R comprises at least 40% by weight, more particularly at least 50% by weight, or up to 100% by weight, based on the total weight 25 alkyl radicals R present in the compounds of the formula (IV), of alkyl radicals R having 12 to 14 carbon atoms (C12-C14-alkyl).
  • the cation M + may be any cation suitable for agricultural purposes.
  • the cation may be monovalent, i.e. it bears a single cationic charge, or polyvalent, i.e. it bears more than one cationic charge.
  • M + refers 30 to the cation equivalent of the cation.
  • Suitable cations include alkali metal cations, such as sodium or potassium ions, alkaline earth metal cations, such as calcium ion, ammonium (NH4 + ), and cations based on organic amines.
  • M + refers to monovalent cation.
  • Suitable examples of the cation M + are, but not limited to alkali metal cations 35 such as sodium, potassium and lithium cations, and substituted or unsubstituted ammonium cations, for example NH4 + (ammonium), hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium cations, 2- hydroxypropylammonium, di(2-hydroxypropyl)ammonium and tri(2- hydroxypropyl)ammonium cations.
  • alkali metal cations 35 such as sodium, potassium and lithium cations
  • substituted or unsubstituted ammonium cations for example NH4 + (ammonium), hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium cations, 2- hydroxypropylammonium, di(2-hydroxypropyl)ammonium and tri(2- hydroxypropyl)
  • the cation M + is H4-mNR 1 m + , where R 1 is selected from the group consisting of alkyl radicals having preferably 1 to 4 carbon atoms, OH substituted alkyl radicals having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3.
  • the cation M + is selected from the group consisting of hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium cations, 2-hydroxypropylammonium, di(2-hydroxypropyl)ammonium and tri(2- hydroxypropyl)ammonium cations.
  • compound of formula (IV) is sodium C12-C14 ether sulfate.
  • compound of formula (IV) is sodium lauryl ether sulfate.
  • compound of formula (IV) is hydroxyethylammonium lauryl ether sulfate.
  • the anionic surfactant(s) (iii) are chosen from salts of (C12-C14)alkyl ether sulfate; even better from sodium lauryl ether sulfate, hydroxyethylammonium lauryl ether sulfate, and mixtures thereof.
  • the anionic surfactant(s) (iii) are comprised in the aqueous phase of the composition.
  • the total amount of anionic surfactant(s) (iii) is from 1 to 300 g/L (gram of anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount of the composition.
  • the total amount of sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of sulfate anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount of the composition.
  • the total amount of alkyl ether sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of alkyl ether sulfate anionic surfactant (s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to 5 the total amount of the composition.
  • the total amount of anionic surfactant(s) of formula (IV) is from 1 to 300 g/L (gram of anionic surfactant(s) (iii) of formula (IV) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount 10 of the composition.
  • the total amount of (C12-C14)alkyl ether sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of (C12-C14)alkyl ether sulfate anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better 15 from 120 to 180 g/L, relative to the total amount of the composition.
  • the total content of anionic surfactant(s) (iii) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better 20 from 11% to 16% by weight, relative to the total weight of the composition.
  • the total content of sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition.
  • the total content of alkyl ether sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition.
  • the total content of anionic surfactant(s) of formula (IV) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition.
  • the total content of (C12-C14)alkyl ether sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the 5 total weight of the composition.
  • the surfactant mixture (M) The composition according to the invention comprises a surfactant mixture 10 (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates of ethylene oxide and of propylene oxide, and c.
  • the surfactant mixture (M) is in the oily phase of the composition.
  • the anionic surfactant(s) (iii) are not part of said surfactant mixture (M). More preferentially, the anionic surfactant(s) (iii) is in the aqueous phase of 20 the composition, and/or the surfactant mixture (M) is in the oily phase.
  • the surfactant mixture (M) comprises at least one non-ionic surfactant a) chosen from oxyalkylenated fatty alcohols, preferably from oxyethylenated fatty alcohols.
  • the oxyalkylenated fatty alcohols that may be used comprise: - a linear or branched hydrocarbon chain having from 8 to 30, better from 10 to 20, even better from 10 to 14 carbon atoms, and - from 1 to 50, better from 2 to 15, even better from 5 to 10 alkylene oxide groups, for instance ethylene and/or propylene oxide groups, 30 more preferentially ethylene oxide groups.
  • Useful non-ionic surfactants a) are in particular the following products, all marketed by Solvay: - Rhodasurf ® BC 610: ethoxylated tridecyl alcohol, 6EO - Rhodasurf ® 860/P: ethoxylated isodecyl alcohol, 6 EO - Rhodasurf ® TDA 8.5: ethoxylated isotridecyl alcohol, 8.5 EO - Rhodasurf ® BC 630: ethoxylated tridecyl alcohol, 7 EO - Rhodasurf ® BC 720: ethoxylated tridecyl alcohol, 10 EO 5 - Rhodasurf ® BC 840: ethoxylated tridecyl alcohol, 15 EO.
  • the Hydrophilic-Lipophilic Balance (HLB) of the oxyalkylenated fatty alcohols a) ranges from 8 to 16; more preferentially from 9 to 15; better from 10 to 14; or even better from 11 to 13. 10
  • the HLB being the ratio of the hydrophilic part to the lipophilic part in the surfactant.
  • HLB is well known to a person skilled in the art and is described, for example, in “The HLB system. A time-saving guide to Emulsifier Selection” (published by ICI Americas Inc., 1984).
  • the HLB of the ionic surfactants is preferably determined by Davies’ method, and the HLB of 15 the non-ionic surfactants is preferably determined by Griffin’s method.
  • the non-ionic surfactants a) are chosen from oxyethylenated fatty alcohols. More preferentially, the non-ionic surfactants a) are chosen from oxyethylenated fatty alcohols comprising 20 from 8 to 30, better from 10 to 20, even better from 10 to 14 carbon atoms and from 1 to 50, preferentially from 1 to 30, better from 2 to 15, even better from 5 to 10, and still better from 5 to 7 ethylene oxide groups.
  • the total amount of oxyalkylenated fatty alcohol(s) a) is from 1 to 25 60 g/L (gram of oxyalkylenated fatty alcohol(s) per liter of composition), preferentially from 2 to 50 g/L, more preferentially from 5 to 40 g/L, even more preferentially from 10 to 30 g/L, better from 12 to 25 g/L, and even better from 13 to 20 g/L, relative to the total amount of the composition.
  • the total amount of oxyethylenated fatty alcohol(s) a) is from 1 to 30 60 g/L (gram of oxyethylenated fatty alcohol(s) per liter of composition), preferentially from 2 to 50 g/L, more preferentially from 5 to 40 g/L, even more preferentially from 10 to 30 g/L, better from 12 to 25 g/L, and even better from 13 to 20 g/L, relative to the total amount of the composition.
  • the total content of oxyalkylenated fatty alcohol(s) a) ranges from 0.1% to 10% by weight, more preferentially from 0.5% to 5% by weight, even more preferentially from 1% to 4% by weight, even better from 1% to 3% by weight, relative to the total weight of the composition.
  • the total content of oxyethylenated fatty alcohol(s) a) ranges from 0.1% to 10% by weight, more preferentially from 0.5% to 5% by weight, even more preferentially from 1% to 4% by weight, even better from 1% to 3% by weight, relative to the total weight of the composition.
  • the surfactant mixture (M) comprises at least one non-ionic surfactant b) chosen from polycondensates of ethylene oxide and of propylene oxide.
  • the non-ionic surfactants b) are chosen from di- or tri-block 15 polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide.
  • non-ionic surfactants are block polymers, of the A-B type, the A-B-A type or the B-A-B type comprising blocks of polyethylene oxide (unit A) and propylene oxide (unit B), or of the A-B-C type, the A-B-A-C type, the B-A-B-C 20 type, the C-A-B-A-C type or the C-B-A-B-C type comprising polyethylene oxide, polypropylene oxide and (C1-C8)alkanol or hydroxy(alkyl)aryl group(s) (unit C).
  • the mean molar mass is advantageously at least 950g/mol, preferably at least 2000g/mol, typically between 2000 g/mol and 7000g/mol, more preferentially between 2000 g/mol and 4000g/mol.
  • the polyethylene oxide content is advantageously at least 25 10% by weight, preferably at least 20% by weight, even more preferably at least 40% by weight of the polycondensate of ethylene oxide and of propylene oxide.
  • the polycondensates of ethylene oxide and propylene oxide that may be used in the composition according to the invention have a mean molar mass ranging from 850 to 15000, and more 30 preferably ranging from 1200 to 10000, more preferably ranging from 1500 to 6500, and still more preferably ranging from 1500 to 5000 g/mol.
  • the non-ionic surfactants b) are chosen from polycondensates of ethylene oxide and of propylene oxide of formula (V): 35 R-(O-CH2-CH2)a–(O-CH(CH3)-CH2)b–(O-CH2-CH2)a’–(O-CH(CH3)-CH2)b’–O–R’ (V) in which: 5 R and R’ are each independently H, alkyl, aryl, alkylaryl or arylalkylaryl; wherein R and/or R’ may comprise a carbonyl to form an ester function with the rest of the polymer, preferably R and R’ are H; a is an integer between 0 and 150, a’ is an integer between 2 and 150, 10 b is an integer between 1 and 100, b’ is an integer between 0 and 100, and when a is not equal to 0, then b’ is 0 and a is preferably between 2 and 150, and when b’ is not equal to 0, then a is 0 and 0 and
  • a in formula (V) is 0.
  • b’ in formula (V) is 0.
  • both a and b’ in formula (V) are 0.
  • R and R’ both denote an hydrogen atom and b’ is 0.
  • the polycondensates of ethylene oxide and of propylene oxide b) are chosen from poloxamers.
  • a “poloxamer” is a non-ionic triblock copolymer comprising a central hydrophobic chain of polyoxypropylene (i.e.
  • the composition comprises, as non-ionic surfactant b), at least one poloxamer having a mean molar 5 mass between 2500 and 3000 g/mol, and a polyethylene oxide content between 20% and 50% by weight, for example Poloxamer 184 such as Antarox ® L64 marketed by Solvay.
  • the Hydrophilic-Lipophilic Balance (HLB) of the oxyalkylenated 10 fatty alcohols a) ranges from 4 to 20; more preferentially from 8 to 18; even better from 12 to 18; for instance 15.
  • the total amount of polycondensate(s) of ethylene oxide and propylene oxide b) is from 5 to 200 g/L (gram of polycondensate(s) per liter of 15 composition), more preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition.
  • the total amount of di- or tri-block polymer(s), wherein the polymeric moiety being composed of ethylene oxide and propylene oxide is from 5 to 200 g/L (gram of said di- or tri-block polymer(s) per liter of composition), more 20 preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition.
  • the total amount of polycondensate(s) of ethylene oxide and propylene oxide of formula (V) is from 5 to 200 g/L (gram of polycondensate(s) per liter of composition), more preferentially from 7 to 100 g/L, even more preferentially 25 from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition.
  • the total amount of poloxamer(s) is from 5 to 200 g/L (gram of poloxamer(s) per liter of composition), more preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the 30 total amount of the composition.
  • the total content of polycondensate(s) of ethylene oxide and propylene oxide b) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better 35 from 1% to 4% by weight, relative to the total weight of the composition.
  • the total content of di- or tri-block polymer(s), wherein the polymeric moiety being composed of ethylene oxide and propylene oxide ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, 5 relative to the total weight of the composition.
  • the total content of polycondensate(s) of ethylene oxide and propylene oxide of formula (V) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, relative to the total weight of the 10 composition.
  • the total content of poloxamer(s) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, relative to the total weight of the composition.
  • the surfactant mixture (M) comprises at least one surfactant c) chosen from phosphate ester surfactants.
  • the phosphate ester surfactant(s) c) are different 20 from selected anionic surfactants (iii) and non-ionic surfactants a) described above.
  • Phosphate ester surfactants are generally known.
  • the phosphate esters as surfactants c) can be more particularly selected from among those comprising: 1) at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group, comprising 8 to 70 carbon atoms, preferably 10 to 40, optionally substituted with at 25 least one oxyalkylenated group (ethoxylated, propoxylated, ethopropoxylated group), and 2) at least one phosphate ester group, mono- or di-esterified such that it is possible to have one or two free or partly or totally salified groups.
  • Suitable phosphate ester surfactants that may be cited are, for example, butyl phosphate, ethoxylate butyl phosphate, dibutyl phosphate, ethoxylated dibutyl30 phosphate, hexyl phosphate, dihexyl phosphate, 2-ethylhexylphosphate, di-2- ethylhexyl phosphate, octyl phosphate, ethoxylated octyl phosphate dioctyl phosphate, ethoxylated dioctyl phosphate, decyl phosphate, didecyl phosphate, stearyl phosphate, ethoxylated stearyl phosphate, distearyl phosphate, ethoxylated distearyl phosphate and mixtures thereof.
  • the phosphate ester surfactant(s) may be chosen from those of formula (VI) above or an agronomically acceptable salt thereof: wherein: * R1 and R2 are each independently H, alkyl, alkenyl, aryl, alkylaryl or arylalkylaryl; provided that at least one of R1 and R2 is alkyl, alkenyl, aryl, alkylaryl or arylalkylaryl, * m and m′ are each independently 2, 3, or 4; provided, if n is greater than 1, that m may differ independently for each (CmH2mO) repeat unit, and if n′ is greater than 1, that m′ may differ independently for each (Cm′H2m′O) repeat unit, and * n and n′ are each independently 0 or an integer of from 1 to about 25.
  • R1 and R2 are each independently H, (C4- C22)alkyl, (C4-C22)alkenyl, (C1-C6)alkylaryl or aryl(C1-C6)alkylaryl.
  • R1 and R2 are each independently H, (C8-C18)alkyl, or aryl(C1-C6)alkylaryl. More preferentially, at least R1 is aryl(C1-C6)alkylaryl such as a tristyrylphenyl group.
  • n and n′ are each independently 0 or an integer of from 10 to 22, preferably n and n′ are an integer of from 14 to 22, more preferentially from 14 to 18.
  • the phosphate ester surfactant(s) c) are chosen from: - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol; - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) C8-C30 (preferentially C10-C22, better C10-C18) aliphatic alcohol; - the
  • the phosphate ester surfactant(s) c) are chosen from: - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol; - the mono- and di-esters of phosphoric acid and of oxyalkylenated 10 (preferentially oxyethylenated) C8-C30 (preferentially C10-C22, better C10-C18) aliphatic alcohol; - salts thereof, and - mixtures thereof. 15 More preferentially, the phosphate ester surfactant(s) c) are in salt form.
  • the phosphate ester surfactant(s) c) are salified with a suitable base.
  • suitable bases include sodium, potassium, lithium, ammonium hydroxides and amines; preferably alkanolamines such as triethanolamine, diethanolisopropanolamine and diglycoldiisopropanolamine.
  • the salts of the phosphate esters may be of any suitable 20 base:acid molar ratio salts, such as those ranging from 0.7 to 1.7, as dictated by the properties of the salt.
  • the phosphate ester surfactant(s) c) are chosen from the mono- and di-esters of phosphoric acid and of 25 oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, neutralized with triethanolamine salt.
  • the phosphate ester surfactant(s) c) are chosen from ethoxylated tri-styrylphenol phosphates, acidic form, such as for example Soprophor ® 3D33, Dispersogen ® LFH.
  • the phosphate ester surfactant(s) c) are chosen from ethoxylated tri-styrylphenol phosphates neutralized with triethanolamine salt, such as Soprophor ® FL, Dispersogen ® LFS.
  • the total amount of phosphate ester surfactant(s) c) is from 5 to 150 g/L (gram of phosphate ester surfactant(s) c) per liter of composition), more preferentially from 10 to 100 g/L, even more preferentially from 15 to 50 g/L, even better from 20 to 30 g/L, relative to the total amount of the composition.
  • the total amount of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, preferably neutralized with triethanolamine salt is from 5 to 150 g/L (gram of ester(s) per liter of composition), more preferentially from 10 to 100 g/L, even more preferentially from 15 to 50 g/L, even better from 20 to 30 g/L, relative to the total 10 amount of the composition.
  • the total content of phosphate ester surfactant(s) c) ranges from 0.4% to 15% by weight, more preferentially from 0.9% to 10% by weight, even more preferentially from 1.2% to 5% by weight, even better from 1.5% to 3.5% by weight, 15 relative to the total weight of the composition.
  • the total content of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, preferably neutralized with triethanolamine salt ranges from 0.4% to 15% by weight, more preferentially from 0.9% to 10% by weight, even more preferentially from 1.2% 20 to 5% by weight, even better from 1.5% to 3.5% by weight, relative to the total weight of the composition.
  • the surfactant mixture (M) is comprised in the oily phase of the composition according to the invention.
  • the composition according to the invention does not contain any rheological agent nor suspension agent nor thickener agent, such as xanthan gum, precipitated or fumed silica, or clay such as attapulgite.
  • the composition is preferably for agricultural use.
  • the composition according to the invention may further comprise at least one additional agricultural material, other than dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof.
  • Agriculture uses many agricultural materials. They are also referred to as active plant-protection products or active materials or active substances.
  • the term “agricultural material” means an active ingredient used in particular to the practice of farming, including cultivation of the soil for the growing of crops.
  • agricultural materials are not limited to application to crops. Agricultural materials may be applied to any surface, e.g., for the purpose of cleaning or aiding or inhibiting growth of a living organism. Other non- crop applications include, but are not limited to, application to an animal, e.g. livestock, application to turf and ornamentals, and application to railroad weed. Agricultural materials are generally products in pure or highly concentrated form, generally not soluble in water and known to the person skilled in the art. Depending on the water solubility of the agricultural materials and their loading in the targeted formulation, it can be very challenging to identify suitable solvents to obtain a chemically and physically stable formulation. For agricultural materials with a low or relatively low water solubility, the use of appropriate solvents is therefore interesting to prepare concentrated liquid formulations.
  • Such concentrated formulations of agricultural materials are generally diluted prior to agricultural use.
  • the dilution effected by the farmer is generally performed by mixing the agrochemical formulation with water.
  • the additional agricultural materials are water-insoluble agricultural materials, at 25°C and at atmospheric pressure (i.e., 1.013x10 5 Pa).
  • the water solubility of the additional agricultural material is strictly less than 100 g/L, even more preferentially strictly less than 20 g/L, in particular strictly less than 5 g/L, for instance strictly less than 1 g/L and even strictly less than 0.2 g/L, at 25°C and at atmospheric pressure (i.e., 1.013x10 5 Pa).
  • the additional agricultural materials are water-soluble agricultural materials, at 25°C and at atmospheric pressure (i.e., 1.013x10 5 Pa). More preferentially according to this embodiment, the water solubility of the additional agricultural material is advantageously greater than or equal to 20 g/L, preferably greater than or equal to 50 g/L, more preferentially greater than or equal to 100 g/L, at 25°C and at atmospheric pressure (i.e., 1.013x10 5 Pa).
  • the additional agricultural materials are chosen from pesticides, nutrients, biostimulants, plant growth regulators, and mixtures thereof.
  • these pesticides may be chosen from herbicides, other than dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof, 5 fungicides, insecticides, acaricides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides.
  • herbicides other than dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof, 5 fungicides, insecticides, acaricides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides.
  • the person skilled in the art is familiar with such pesticides.
  • Specific examples of pesticides can be found in the book “Sittig’s handbook of Pesticides and Agricultural Chemicals”, 2 nd edition, William Andrew Publishing, 2015. 10 Nutrients refer to chemical elements and compounds
  • Nutrients generally are described as macronutrients or micronutrients. Suitable nutrients for use in the composition according to the invention may be micronutrient compounds, preferably those which are solid at room temperature 15 (20°C) or are partially soluble. Micronutrients typically refer to trace metals or trace elements, and are often applied in lower doses. Suitable micronutrients include trace elements selected from zinc, boron, chlorine, copper, iron, molybdenum, and manganese. The micronutrients may be in a soluble form or included as insoluble solids, 20 and may be in the form of salts or chelates. Preferably, the micronutrient is in the form of a carbonate or oxide.
  • the micronutrients may be selected from zinc, calcium, molybdenum or manganese, or magnesium. More preferentially micronutrients for use in the agrochemical formulation according to the invention may be selected from zinc 25 oxide, manganese carbonate, manganese oxide, or calcium carbonate.
  • Macronutrients typically refer to those comprising nitrogen, phosphorus, and potassium, and include fertilisers such as ammonium sulphate, and water conditioning agents.
  • Suitable macronutrients include fertilisers and other nitrogen, phosphorus, or sulphur containing compounds, and water conditioning agents.
  • Suitable fertilisers include inorganic fertilisers that provide nutrients such as nitrogen, phosphorus, potassium or sulphur.
  • Such fertilisers include: for nitrogen as the nutrient: nitrates and or ammonium salts such as ammonium nitrate, including in combination with urea e.g. as urean type materials, calcium ammonium nitrate, ammonium sulphate nitrate, ammonium phosphates, 35 particularly mono-ammonium phosphate, di-ammonium phosphate and ammonium polyphosphate, ammonium sulphate, and the less commonly used calcium nitrate, sodium nitrate, potassium nitrate and ammonium chloride; for phosphorus as the nutrient: acidic forms of phosphorus such as phosphoric, pyrophosphoric or polyphosphoric acids, but more usually salt forms such as 5 ammonium phosphates, particularly mono-ammonium phosphate, di-ammonium phosphate, and ammonium polyphosphate, potassium phosphates, particularly potassium dihydrogen phosphate and potassium polyphosphate; for sulphur as the ure
  • biostimulant is preferably intended to mean a compound which may enhance metabolic or physiological processes such as respiration, photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or a combination thereof. Generally, this is a substance or microorganism that, when applied to seeds, plants or on the rhizosphere, can stimulate natural processes to enhance or benefit 15 nutrient uptake, nutrient use efficiency, tolerance to abiotic stress, or crop quality and yield.
  • biostimulants include seaweed extracts (e.g., ascophyllum nodosum), humic acids (e.g., potassium humate), fulvic acids, myoinositol, glycine, and combinations thereof.
  • Plant growth regulators mean active ingredients used to influence the growth characteristics of plants.
  • plant growth regulators which may be used in the present invention include, but are not limited to: 1-naphthaleneacetic acid, 1- naphthaleneacetic acid -salt, 1-napthol, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4- DB, 2,4-DEP, 2,3,5-triiodobenzoic acid, 2,4,5-trichlorophenoxyacetic acid, 2-25 naphthoxyacetic acid, 2-naphthoxyacetic acid sodium salt, 3-chloro-4- hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4- chlorophenoxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6- benzylaminopurine, auxindole, a-naphthaleneacetic acid K-salt, ß-naphfhoxyacetic acid, p-chlorophenoxyacetic acid, dicamba, dichlorprop, feno
  • the amount of agricultural material(s) in the composition, 10 including dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof ranges from 0.01 to 90% by weight, more preferentially from 0.1 to 80% by weight; even more preferentially from 0.5 to 70% by weight; better from 1 to 65% by weight, in particular from 5 to 60% by weight, and for instance from 10 to 40% by weight, relative to the total weight of the composition.
  • the composition according to the invention is an emulsion in water concentrate (EW).
  • EW formulation consists of a concentrated oil-in-water emulsion, intended to 20 be diluted with a carrier, usually water when preparing the spray mixture, in the form of a more diluted emulsion for application in the field.
  • the oil-in-water emulsion according to the invention advantageously comprises an aqueous phase as the continuous phase and an oil phase as the discontinuous phase.
  • the oil phase usually forms droplets in the aqueous phase. 25
  • the average droplet size can be determined by particle size measurement by laser diffraction, e.g. with a Malvern Mastersizer 2000 or 3000. More details can be found in the examples.
  • the median droplet size value for volumic particle size distribution dv(50) is usually in the range from 0.1 to 3 ⁇ m, more preferentially from 0.2 to 2.5 ⁇ m, 30 even more preferentially from 0.4 to 2.0 ⁇ m and even better from 0.7 to 1.5 ⁇ m.
  • the Span index ranges from 0.4 to 15; more preferentially from 0.5 to 10; even more preferentially from 0.8 to 5 and even better from 1 to 3.
  • the composition according to the invention may advantageously comprise at 35 least 5% by weight, preferably at least 10% by weight and more preferably at least 15% by weight of water, based on the total weight of the emulsion.
  • composition according to the invention may advantageously comprise from 5 to 60% by weight, preferably from 10 to 50% by weight and more preferably from 15 to 40% by weight of water, based on the total weight of the composition.
  • the composition according to the invention may further comprise at least one organic solvent, different from the surfactants (iii), a), b) and c) above; more preferentially at least one non-oxyalkylenated organic solvent.
  • the organic solvents that may be used in the emulsion according to the 10 invention are preferably chosen from: - linear or branched, saturated or unsaturated, aliphatic hydrocarbons, possibly containing a halogen -, phosphorus -, sulfur - and/or nitrogen atom and/or a functional group, - carbocyclic or heterocyclic hydrocarbons, whether saturated, unsaturated or 15 aromatic, possibly containing a halogen -, phosphorus -, sulfur - and/or nitrogen atom and/or a functional group, More preferentially, the solvents are chosen from: - alkanes, cycloalkanes and aromatic derivatives, for example paraffins with a branched chain or straight chain such as "white oil” or decalin; mono-, di- 20 or tri alkyl benzenes or naphthalenes, the compounds sold under the trade name Solvesso ® 100, 150, 200 standard and ND grades; - aliphatic, cycl
  • the composition further comprises at least one aliphatic, cycloaliphatic or aromatic alcohols, different from the surfactants (iii), a), b) and c) above; even better the composition further comprises at least one aliphatic (C1- 20 C8)alcohol such as glycerin and/or n-octanol.
  • the total amount of organic solvent(s), different from the surfactants (iii), a), b) and c) above is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, 25 relative to the total amount of the composition.
  • the total amount of glycerin is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition.
  • the total content of organic solvent(s), different from the surfactants (iii), a), b) and c) above ranges from 0.1% to 20% by weight, more preferentially from 0.1% to 14% by weight, even more preferentially from 1% to 10% by weight, even better from 3% to 8% by weight, relative to the total weight of the composition.
  • the total content of glycerin ranges from 0.1% to 20% by weight, more preferentially from 0.1% to 14% by weight, even more preferentially from 1% to 10% by weight, even better from 3% to 8% by weight, relative to the total weight of the composition.
  • the aqueous-phase of the composition further comprises at least one solvent chosen from aliphatic, cycloaliphatic or aromatic alcohols, different from the surfactants (iii), a), b) and c) above; preferably from aliphatic (C1-C8) alcohols such as glycerine or n-octanol.
  • the total amount of aqueous-phase solvent(s), different from the surfactants (iii), a), b) and c) above is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition.
  • the oily phase of the composition further comprises at least one non-water miscible organic solvent, more preferably chosen from aromatic solvents such as paraffins, mono-, di- or tri alkyl benzenes or naphthalenes and aromatic ketones such as acetophenone, amides such as alkyldimethylamides, and mixtures thereof.
  • the total amount of oily-phase solvent(s) is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition.
  • a “non-water miscible organic solvent” is an organic solvent having a water solubility, at 25°C and at atmospheric pressure (i.e., 25 1.013x10 5 Pa), advantageously strictly less than 2 g/L (gram of solvent per litre of water), strictly less than 1.5 g/L, more preferentially strictly less than 1 g/L, even more preferentially strictly less than 0.5 g/L, and even better strictly less than 0.1 g/L.
  • Crystallisation inhibitors may also be present in the composition according to the invention. Crystallisation inhibitors may be the solvents mentioned here above.
  • Crystallisation inhibitors may also be non-oxyalkylenated fatty alcohols or fatty acids, for example mention may be made of the product Alkamuls ® OL700 marketed by Solvay, alkanolamides, polymers etc.
  • the composition according to the invention may further contain one or more additives different from the ingredients described previously, and which are preferably chosen from viscosity modifying agents, suspending agents, antifoam agents and defoamers, in particular silicone antifoams and defoamers, anti-rebound agents, anti- 5 leaching agents, penetration adjuvants, inert fillers, in particular mineral fillers, binders, diluents, anti-freeze agents, stabilisers, dyes, emetic agents, stickers (adhesion promoters), dispersants, preservatives and/or anti-microbials.
  • Each additive can be present in the composition according to the invention in an amount ranging from 0% to 20% by weight, more preferably from 0% to 10% by 10 weight, relative to the total weight of the composition.
  • Each additive can be for instance present in the composition according to the invention in an amount ranging from 0.1% to 20% by weight, in particular from 0.1% to 10% by weight, relative to the total weight of the composition.
  • Each additive can be present in the composition according to the invention in an amount preferably ranging from 0% to 5% by weight, notably from 15 0.1% to 5% by weight, relative to the total weight of the composition.
  • a person skilled in the art will be able to choose these optional additives and their amounts so that they do not harm the properties of the compositions of the present invention.
  • the weight ratio of the total amount of aqueous phase of the 20 composition to the total amount of the oily phase ranges from 1 to 5; more preferentially from 1.1 to 4; even more preferentially from 1.5 to 3.5; even better from 2 to 3. 25
  • the composition according to the invention may exhibit a non-Newtonian "shear thinning" viscosity, that is, a viscosity that, within a given range of shear stress, decreases with increasing shear stress.
  • the two generally recognized categories of flow behavior are plastic flow behavior and pseudoplastic flow behavior, each include shear thinning flow behavior. 30
  • the composition of the invention exhibits plastic flow behavior.
  • plastic in reference to flow behavior of a composition means the composition that exhibits a characteristic "yield stress", that is, a minimum shear stress required to initiate flow of the composition, and exhibits shear thinning behavior over some range of shear stress above the yield stress.
  • the composition 20 is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an agronomically acceptable salt thereof, (ii) dimethenamid-P, (iii) at least one sulfate anionic surfactant, preferably at least one alkyl 25 ether sulfate surfactant, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, preferably from oxyethylenated fatty alcohols, b.
  • EW oil-in-water emulsion
  • At least one non-ionic surfactant chosen from oxyethylenated fatty alcohols comprising a linear or branched hydrocarbon chain having from 8 to 30, preferably from 10 to 20, even better from 10 to 14 carbon atoms and from 1 to 50, preferentially 15 from 1 to 30, better from 2 to 15, even better from 5 to 10, and still better from 5 to 7 ethylene oxide groups, b. at least one non-ionic surfactant chosen from di- or tri-block polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide such as poloxamers, and 20 c.
  • the composition is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an agronomically acceptable salt thereof, (ii) dimethenamid-P, 30 (iii) at least one alkyl ether sulfate surfactant, preferably chosen from alkyl ether sulfate surfactants of formula (IV) as described above, and (iv) a surfactant mixture (M) comprising: a.
  • EW oil-in-water emulsion
  • composition according to the invention may be used to kill or inhibit pests and/or clean and/or inhibit growth of undesired plants.
  • the composition according to the invention can be diluted and applied to at least one plant, area adjacent to a plant, soil adapted to support growth of a plant, root of a plant and/or foliage of a plant, in a customary manner; for example, by watering (drenching), drip irrigation, spraying, and/or atomizing.
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical mixture according to the invention is thus obtained.
  • 20 to 25 2000 litres, preferably 50 to 400 litres, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • the invention also relates to the use of a composition as defined herein for controlling undesirable vegetation in burndown programs, in industrial vegetation 30 management and forestry, in vegetable and perennial crops and in turf and lawn, wherein the inventive composition can be applied pre- or post-emergence, i.e., before, during and/or after emergence of the undesirable plants.
  • the inventive compositions are applied to a locus where crops will be planted 35 before planting or emergence of the crop. Therefore, the present invention also relates to a method for burndown treatment of undesirable vegetation in crops, comprising applying an inventive composition to a locus where crops will be planted before planting (or seeding) or 5 emergence of the crop.
  • present invention therefore relates to a method for controlling undesirable vegetation, which method comprises applying an inventive composition to 10 a locus where undesirable vegetation is present or is expected to be present, wherein application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable vegetation.
  • controlling and “combating” are synonyms. 15
  • undesirable vegetation are synonyms.
  • locus means the area in which the vegetation or plants are growing or will grow, typically a field. 20
  • the inventive composition can be applied prior to seeding (planting) or after seeding (or planting) of the crop plants but before the emergence of the crop plants, in particular prior to seeding.
  • the inventive compositions are preferably applied prior to seeding of the crop plants.
  • the inventive 25 composition will generally be applied a date up to 9 months, frequently up to 6 months, preferably up to 4 months prior to planting the crop.
  • the burndown application can be done at a date up to 1 day prior to emergence of the crop plant and is preferably done at a date prior to seeding/planting of the crop plant, preferably at a date of at least one day, preferably at least 2 days and in particular at least one 4 days prior to planting or 30 from 6 months to 1 day prior emergence, in particular from 4 months to 2 days prior emergence and more preferably from 4 month to 4 days prior emergence. It is, of course, possible to repeat the burndown application once or more, e.g., once, twice, three times, four times or five times within that time frame.
  • inventive compositions have a very good post-emergence herbicide activity, i.e., they show a good herbicidal activity against emerged undesirable plants.
  • inventive compositions are applied post-emergence, i.e., during and/or after, the 5 emergence of the undesirable plants. It is particularly advantageous to apply the inventive compositions post emergent when the undesirable plant starts with leaf development up to flowering.
  • inventive compositions are particularly useful for controlling undesirable vegetation which has already developed to a state, which is difficult to control with conventional burndown mixtures, i.e., when the individual 10 weed is taller than 10 cm (4 inches) or even taller than 15 cm (6 inches) and/or for heavy weed populations.
  • the inventive compositions are preferably applied by foliar application. 15
  • application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active 20 compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • spray shields may be used.
  • Application may be affected, for example, by usual spraying techniques with water as the carrier, using amounts of spray mixture of usually from 10 to 2000 L/ha, 25 in particular 50 to 1000 L/ha.
  • the required application rate of the composition comprising active compounds depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the composition is 30 used and on the application method.
  • the application rate of the composition is from 55 to 6000 g/ha, preferably from 100 to 5000 g/ha, from 200 to 4000 g/ha, and more preferably from 300 to 3000 g/ha of active ingredient (a.i.).
  • the inventive compositions show a persistent herbicidal activity, 35 even under difficult weathering conditions, which allows a more flexible application in burndown applications and minimizes the risk of weeds escaping.
  • inventive compositions show superior crop compatibility with certain conventional crop plants and with herbicide tolerant crop plants, i.e., their use in these crops leads to a reduced damage of the crop plants and/or does not result in increased damage of 5 the crop plants.
  • inventive compositions can also be applied after the emergence of the crop plants.
  • the inventive compositions may also show an accelerated action on harmful plants, i.e. they may affect damage of the harmful plants more quickly if compared to individual components.
  • the inventive compositions are suitable for controlling a large number of harmful plants in agricultural crops, including monocotyledonous weeds, in particular annual weeds such as gramineous weeds (grasses) including Echinochloa species such as barnyardgrass (Echinochloa crusgalli var.
  • Echinchloa walteri Pulursh 15 Heller, jungle rice (Echinochloa colona), Echinochloa cruspavonis, Echinochloa oryzicola, Digitaria species such as crabgrass (Digitaria sanguinalis), Digitaria horizontalis, sourgrass (Digitaria insularis) or naked crabgrass (Digitaria nuda), Setaria species such as green foxtail (Setaria viridis), giant foxtail (Setaria faberii), yellow foxtail (Setaria glauca or Setaria pumila) or Setaria verticillata, Sorghum species such 20 as johnsongrass (Sorghum halepense Pers.), Avena species such as wild oats (Avena fatua), Avena sterillis or Avena strigosa, Cenchrus species such as Cenchrus species such as field sandbur (Cenchrus pauciflorus) or Cenchrus e
  • Poa species such as Poa annua or Poa trivialis L., Puccinellia distans, Rottboellia cochinchinensis, Sclerochloa kengiana (Ohwi) Tzvel., Trichloris crinita, Urochloa or Brachiaria species such as Brachiaria decumbens, Brachiaria plantaginea, Brachiaria platyphylla, Urochloa panicoides, Urochloa ramosa and the 10 like.
  • Both L-glufosinate alone as well as the inventive mixtures are also suitable for controlling a large number of dicotyledonous weeds, in particular broad leaf weeds including Polygonum species such as wild buckwheat (Polygonum convolvolus), 15 Polygonum pensilvanicum, Polygonum persicaria or prostrate knotweed (Polygonum aviculare), Amaranthus species such as pigweed (Amaranthus retroflexus), Palmer amaranth (Amaranthus palmeri), tall waterhemp (Amaranthus tuberculatus or Amaranthus rudis), redroot pigweed (Amaranthus retroflexus), green amaranth (Amaranthus hybridus), purple amaranth (Amaranthus lividus), prickly amaranth 20 (Amaranthus spinosus) or Amaranthus quitensis, Chenopodium species such as common lambsquarters (Chenopodium album L.), Chenopodium serotin
  • Both L-glufosinate alone as well as the inventive compositions are also suitable for controlling a large number of annual and perennial sedge weeds including Cyperus species such as purple nutsedge (Cyperus rotundus L.), yellow nutsedge 15 (Cyperus esculentus L.), himekugu (Cyperus brevifolius H.), sedge weed (Cyperus microiria Steud), rice flatsedge (Cyperus iria L.), Cyperus difformis, Cyperus difformis L., Cyperus esculentus, Cyperus ferax, Cyperus flavus, Cyperus iria, Cyperus lanceolatus, Cyperus odoratus, Cyperus rotundus, Cyperus serotinus Rottb., Eleo- charis acicularis, Eleocharis kuroguwai, Fimbristylis dichotoma, Fimbristyl
  • Both L-glufosinate alone as well as the inventive compositions are also 25 suitable for controlling weeds that are resistant to commonly used herbicides such as, for example, weeds that are resistant to glyphosate, weeds that are resistant to auxin inhibitor herbicides such as e. g. 2,4-D or dicamba, weeds that are resistant to photosynthesis inhibitors such as e. g. atrazine, weeds that are resistant to ALS inhibitors such as e. g. sulfonylureas, imidazolinones or triazolopyrimidines, weeds 30 that are resistant to ACCase inhibitors such as e. g.
  • clodinafop clethodim or pinoxaden or weeds that are resistant to protoporphyrinogen-IX-oxidase inhibitors such as e. g. sulfentrazone, flumioxazine, fomesafen or acifluorfen, for example the weeds that are listed in the International Sur-vey of Resistant Weeds (http://www.weedscience.org/Summary/SpeciesbySOATable.aspx).
  • mice Micranthos, Cirsium arvense, Commelina 30 diffusa, Echinochloa cruspavonis, Soliva sessilis and Sphenoclea zeylanica, HPPD inhibitor resistant Amaranthus palmeri and Amaranthus rudis, PPO inhibitor resistant Acalypha australis, Amaranthus hybridus, Amaranthus palmeri, Amaranthus retroflexus, Amaranthus rudis, Ambrosia artemisifolia, Avena fatua, Conyza sumatrensis, Descurainia sophia, Euphorbia heterophylla and Senecio vernalis, 35 carotenoid biosynthesis inhibitor resistant Hydrilla verticillata, Raphanus raphanistrum, Senecio vernalis and Sisymbrium orientale, VLCFA inhibitor resistant Alopecurus myosuroides, Avena fatua and Echinochloa crus galli.
  • inventive compositions are suitable for combating/controlling common 5 harmful plants in fields, where useful plants shall be planted (i.e. in crops) or have been planted (i. e. post-emergence to the crop).
  • inventive compositions are generally suitable for control of undesired vegetation, both before emergence of the crop (i. e. burndown) or after emergence of the crop (i. e. post-emergence treatment, ‘over-the- top’, ‘OTT’) in fields of the following crops: 10 - Grain crops, including e.g. - cereals (small grain crops) such as wheat (Triticum aestivum) and wheat like crops such as durum (T. durum), einkorn (T. monococcum), emmer (T.
  • dicoccon and spelt T. spelta
  • rye Secale cereale
  • triticale Tritiosecale
  • barley Hordeum vulgare
  • 15 - maize corn; Zea mays
  • - sorghum e.g. Sorghum bicolour
  • - rice Oryza spp. such as Oryza sativa and Oryza glaberrima
  • sugar cane - Legumes (Fabaceae), including e.g.
  • soybeans (Glycine max.), peanuts 20 (Arachis hypogaea and pulse crops such as peas including Pisum sativum, pigeon pea and cowpea, beans including broad beans (Vicia faba), Vigna spp., and Phaseolus spp. and lentils (lens culinaris var.); - brassicaceae, including e.g. canola (Brassica napus), oilseed rape (OSR, Brassica napus), cabbage (B. oleracea var.), mustard such as B. juncea, B. campestris, 25 B. narinosa, B. nigra and B.
  • canola Brassica napus
  • OSR oilseed rape
  • cabbage B. oleracea var.
  • mustard such as B. juncea, B. campestris, 25 B. narinosa, B. nigra and B.
  • TNV-crops TNV: trees, nuts and vine
  • grapes citrus, pomefruit, e.g. apple and pear
  • coffee pistachio and oilpalm
  • stonefruit e.g.
  • peach 30 almond, walnut, olive, cherry, plum and apricot
  • turf pasture and rangeland
  • - bulb ornamentals such as tulips and narcissus
  • - conifers and deciduous trees such as pinus, fir, oak, maple, dogwood, 35 hawthorne, crabapple, and rhamnus (buckthorn)
  • - garden ornamentals such as roses, petunia, marigold and snapdragon.
  • the inventive compositions are in particular suitable for burndown of undesired vegetation in fields of the following crop plants: small grain crops such as 5 wheat, barley, rye, triticale and durum, rice, maize (corn), sugarcane, sorghum, soybean, pulse crops such as pea, bean and lentils, peanut, sunflower, sugarbeet, potato, cotton, brassica crops, such as oilseed rape, canola, mustard, cabbage and turnip, turf, pasture, rangeland, grapes, pomefruit, such as apple and pear, stonefruit, such as peach, almond, walnut, pecans, olive, cherry, plum and apricot, citrus, coffee, 10 pistachio, garden ornamentals, such as roses, petunia, marigold, snap dragon, bulb ornamentals such as tulips and narcissus, conifers and deciduous trees such as pinus, fir, oak, maple, dogwood, hawthorne, crabapple and rhamnus.
  • small grain crops
  • the invention furthermore relates to the use of a compositions as defined 15 herein for controlling undesirable vegetation in crops in a burndown or post-emergence or OTT program, wherein the crop is produced by genetic engineering or by breeding, are resistant to one or more herbicides and/or pathogens such as plant-pathogenous fungi, and/or to attack by insects; preferably resistant to glufosinate.
  • crops as used herein 20 includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create 25 mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create 30 modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait.
  • transgenic plants These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant 35 transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name.
  • Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, 5 insect resistance, in-creased yield and tolerance to abiotic conditions, like drought. Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering.
  • Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield ® . However, 10 most of the herbicide tolerance traits have been created via the use of transgenes.
  • inventive compositions on crops may result in effects which are specific to a crop com-prising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors.
  • Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • glufosinate tolerant crop plant is preferably selected from the group consisting of rice, canola, soybean, corn and cotton plants.
  • inventive compositions can be applied in conventional manner by using 30 techniques as skilled person is familiar with. Suitable techniques include spraying, atomizing, dusting, spreading or watering. The type of application depends on the intended purpose in a well-known manner; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the inventive compositions are applied to locus mainly by spraying, in particular foliar spraying of an aqueous dilution of the active ingredients of the mixture.
  • Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 5 to 2000 L/ha or 50 to 1000 L/ha (for example from 100 to 500 L/ha).
  • inventive compositions by the low-volume and the ultra-low-volume method is possible, as is their application in the form of microgranules.
  • the required application rate of the mixture of the pure active compounds 10 depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the mixture is used and on the application method.
  • the rate of application of L-glufosinate is usually from 100 g/ha to 15 1500 g/ha, preferably in the range from 200 g/ha to 1000 g/ha or from 300 g/ha to 1000 g/ha and most preferably in the range of 300 g/ha to 800 g/ha or 300 g/ha to 700 g/ha of active substance (a.i.), and the rate of application of Dimethenamid-P is from 100 g/ha to 2000 g/ha and preferably in the range from 200 g/ha to 1500 g/ha, more preferably from 300 g/ha to 1000 g/ha and most preferably in the range from 400 g/ha 20 to 1000 g/ha of active substance (a.i.).
  • L-glufosinate ammonium To 28 mg of L-glufosinate ammonium, 25 mL diluent A (0.05 mol/L 25 potassium phosphate monobasic in water/acetonitrile 90/10 (v/v)) was added. To 240 mg of test sample (formulations in Table A), 25 mL diluent A (0.05 mol/L potassium phosphate monobasic in water/acetonitrile 90/10 (v/v)) is added.
  • DMTA-p 30 To 30 mg of DMTA-p was added 90 mL acetonitrile and 10 mL water.
  • test sample (formulations in Table A) was added 90 mL acetonitrile and 10 ml water.
  • 35 the mean of the calibration factors is formed from at least two consecutive calibration runs and thus the intervening sample runs are evaluated (bracketing calibration).
  • Preparation and ingredients of the emulsions The following emulsions in water concentrate (EW) A1 to A14 (invention) 5 and A15 to A22 (comparative) were prepared according to Method 1, Method 2 or Method 3 described below.
  • Method 1 Organic phase is prepared in a beaker by addition of dimethenamid-P in solvent, followed by addition of surfactant a), b) and/or c), with gentle stirring.
  • the aqueous phase is prepared by addition of antifoam (if any), glycerine or water-soluble solvent, deionized water, glufosinate ammonium (racemic or L-enantiomer) then by anionic surfactant such as sodium lauryl ether sulfate.
  • High shear mixing IKA Ultraturrax T25 at 7000 rpm during 2 minutes
  • IKA Ultraturrax T25 at 3000 rpm during 30 seconds proceeds the same way with the second quarter, 3rd one and 4th one.
  • Method 2 Organic phase is prepared in a standard vessel with counter-blades, equipped with a high shear impeller (for example Rushton impeller or a dissolver blade): addition of dimethenamid-P is done in solvent, followed by addition of surfactant a), b) and/or c), with gentle stirring.
  • a high shear impeller for example Rushton impeller or a dissolver blade
  • the aqueous phase is prepared by addition of an antifoam (if any), glycerine25 or water-soluble solvent, deionized water, glufosinate ammonium (racemic or L- enantiomer) then by anionic surfactant such as sodium lauryl ether sulfate.
  • An antifoam if any
  • glycerine25 or water-soluble solvent deionized water
  • glufosinate ammonium racemic or L- enantiomer
  • anionic surfactant such as sodium lauryl ether sulfate.
  • High shear mixing IKA Ultraturrax T25 at 7000 rpm during 2 minutes
  • For emulsion preparation add one quarter of the aqueous phase in organic phase with high shear mixing (600 rpm) using Rushton 30 impeller or dissolver blade. Proceed the same way with the second quarter, 3rd one and 4th one.
  • Method 3 Organic phase is prepared in a beaker by addition of dimethenamid-P in 35 solvent with gentle stirring.
  • the aqueous phase is prepared by addition of antifoam, glycerine, deionized water, glufosinate ammonium (racemic or L-enantiomer) then by anionic surfactants such as sodium lauryl ether sulfate and sodium 2-ethylhexyl sulfate.
  • High shear mixing IKA Ultraturrax T25 at 9000 rpm during 2 minutes) is done for 5 homogenization of aqueous phase.
  • a stable formulation is a formulation that do not show any sign of destabilization as described above after the considered period of storage at the considered temperature.
  • a controlled stress rheometer ARG2 (TA Instruments, Surrey, Great Britain), equipped with a geometry of rotor cylinder (diameter: 14mm; cylinder 35 immersed height: 42mm) / stator type having a diameter of 15mm with a gap of 4 mm was used. Shear rate sweep has been done, between 10 -3 sec -1 and 200 sec -1 at 20°C, 10 points per decade and 1 minute stabilization time has been carried out. The static yield stress value is determined as the value of the applied shear stress beyond which the viscosity starts decreasing. 5 ⁇ Measurement of droplets size distribution: The droplets size distribution has been determined by particle-size measurement by means of laser diffraction.
  • the EW emulsion was diluted in deionised water at 1 wt% and stirred with a 10 magnetic stirrer during 1 minute.
  • the preparation was then transferred to the measurement cell of Malvern Mastersizer 2000 or 3000.
  • the quantity of preparation was adjusted to target an obscuration of 10%, with a tolerance for values of 8 and 15%.
  • the analysis may be carried out with the following parameters: Measurement Parameters: duration of the sample measurement: 10 sec; duration of 15 blank measurement: 10 sec; 3 cycles per measurement. Fraunhofer theory was used for the calculations: optical model: [Fraunhofer]; standard analysis, normal sensibility.
  • dv(50) is the median droplet size value (in microns) for volumic particle size distribution, ie the droplet size value (in microns) that splits the distribution in volume 20 with half above and half below. Similarly 90% of the volumic particles distribution lies below dv(90), and 10% of the volumic particle size distribution lies below dv(10).
  • Table 10 C ompositions (C A o 1 m 9 A20 A21 A22 p ) (Comp) (Comp) (Comp) At 20°C, up to 24h after the preparation Phase Weissenberg High effect / High viscosit Phase Appearance separation into y / viscosity / Whit separation into 2 layers e White emulsion emulsion 2 layers 19.
  • compositions according to the invention comprising the specific combination of the surfactants a), b) and c) as claimed, have a good viscosity profile and pourability, as well as a better stability upon storage at room temperature (20°C), or even at 2 weeks at 54°C, than the comparative compositions A15 to A22 which do not comprise the specific combination of the surfactants a), b) and c) as claimed.
  • Example 3 Products: Liberty ® : 280 g/l racemic glufosinate-ammonium 5 Liberty ® Ultra (BAS 101005 H): 211 g/l L-glufosinate ammonium Outlook ® : 720 g/l DMTA-p Roundup PowerMAX ® II: 540 g/l Glyphosate
  • assessment was either after 9 to 17 days 10 after treatment (DAT) or 45 to 50 days after treatment (DAT).
  • Table 11 Post emergence control (9 - 17 DAT) in Soybean and Cotton Compound/formulation Application rate in g Herbicidal activity against ai/ha Pigweed Broadleaf Grass Liberty ® 655 93 93 85 Liberty ® + Outlook ® 655 + 630 92 96 90 Liberty ® Ultra 370 95 94 82 Liberty ® Ultra + Outlook ® 370 + 630 96 97 92 Formulation No. A5 1000 95 98 93 Formulation No. A2 1000 95 96 92 Formulation No.
  • compositions according to the invention comprising the specific combination of the 5 surfactants a), b) and c) as claimed, are not only storage stable, as is evident from data in Tables 6-8 but also retain a good control of wide variety of weeds as seen from the data in Tables 11 and 12.

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Abstract

The present invention relates to a composition, preferably for agricultural use, in the form of an emulsion in water concentrate (EW), comprising glufosinate or L-glufosinate, a VLCFA inhibitor and a combination of specific surfactants. The invention also relates to a method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition onto soils or plants.

Description

EMULSION IN WATER CONCENTRATE COMPRISING GLUFOSINATE, VLCFA INHIBITOR AND SPECIFIC SURFACTANTS 5 The present invention relates to a composition, preferably for agricultural use, in the form of an emulsion in water concentrate (EW), comprising glufosinate or L- glufosinate, a VLCFA inhibitor and a combination of specific surfactants. The invention also relates to a method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition onto 10 soils or plants. Pesticides are widely employed in agricultural pest management. Given their extensive use, there is a constant need to develop methods that can enhance the effectiveness of pesticides. One common approach to increase the potency of an active ingredient is to combine it with one or more other active ingredients that possess 15 desired activity profiles. Such combinations can result in highly efficient synergistic products with broad coverage, potentially allowing for a reduced application rate of active ingredients. As a result, modern agrochemical practices tend to favor combination products containing active ingredients with specific activity profiles. Additionally, appropriate adjuvants can be utilized to improve the performance of 20 active ingredients and/or enhance the physical properties of the formulation. Typically, active ingredients are formulated with various formulation auxiliaries to enhance their activity. Agrochemical formulations can be developed in various ways, primarily based on the physical and chemical characteristics of the active ingredients. Examples of such formulations include aqueous solutions, emulsifiable concentrates, encapsulated 25 suspensions, wettable powders, oil-in-water or water-in-oil emulsions, suspoemulsions, suspo-solutions, microemulsions, emulsions, ZC formulations, and granules. Herbicide formulations based on glufosinate are well known. Glufosinate is a non-selective foliage application type contact herbicide which kills or controls many 30 species of weeds. Generally, glufosinate is used in burn-down segments, and for control of a wide range of broad-leaved weeds and grasses and sedges in cereals, cotton, corn and soy, fruit orchards, vineyards, rubber and oil palm plantations, ornamental trees and bushes, non-crop land, and pre-emergence in vegetables. Glufosinate being a water-soluble active ingredient, it is preferably formulated as 35 aqueous solutions along with incorporation of water-soluble ingredients/adjuvants. In order to favor an optimal biological efficacy of glufosinate, the use of one or more specific adjuvants in glufosinate-based formulation is known. However, some of these adjuvants present drawbacks in the ready-to-use formulation containing glufosinate. 5 One other common practice to increase the activity of glufosinate is to combine it with one or more other active ingredients having desired activity profile. Such combinations can lead to highly effective synergistic products having a broad spectrum coverage which may also enable lowering of application rate of active ingredients. Nevertheless, when water-insoluble active ingredients are to be combined 10 with glufosinate, for example in the form of an emulsion or a dispersion, physical and chemical stability of the formulation needs to be taken care of. Further, pesticide formulations in the form of emulsions, for example described in the applications WO 2002/43488, WO 2007/057028 or DE 69012487, do not give complete satisfaction in terms of stability and viscosity. 15 More particularly, the aqueous continuous phase does not exhibit high ionic strength characteristics, with significant content of salts or ionic ingredients such as glufosinate ammonium salt. It is particularly challenging to stabilize an emulsion displaying high ionic strength, electrolyte-rich characteristics in its continuous phase. It is especially difficult to identify an adequate association of adjuvants and 20 co-formulants that enables a good stability of a concentrated high ionic strength emulsion upon storage (low, high temperature), but also that permits to maintain suitable emulsion characteristics upon dilution in the final carrier, usually water (lower ionic strength character) before application in the field. For such reasons, pesticide emulsions may lead to physical instability issues. 25 In particular, pesticide emulsions may on storage especially under various temperature conditions lead to creaming/oil layer separation, syneresis and/or sedimentation. In addition to such physical compatibility issues, decomposition or antagonism of the considered active substances and/or biological incompatibility are often encountered. Thus, there is a continuous need for providing improved glufosinate-based 30 compositions for agricultural needs, in particular glufosinate-based compositions with good intrinsic properties, in particular good physicochemical properties such as a good stability on storage and an adequate viscosity profile (good pourability). Such compositions should generate good performances at dilution including a good homogeneity of the emulsion and/or dispersion of possible water-insoluble agricultural 35 materials, even for high loading formulations. These objectives are achieved with the present invention, a subject-matter of which is a composition, preferably for agricultural use, in the form of an oil-in-water emulsion (EW) comprising: 5 (i) at least one first herbicide chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof, (ii) at least one second herbicide chosen from dimethenamid, dimethenamid-P, or mixtures thereof, (iii) at least one anionic surfactant, and 10 (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates of ethylene oxide and of propylene oxide, and 15 c. at least one phosphate ester surfactant. The compositions according to the invention present good intrinsic physicochemical properties. In addition, it has been noted that the compositions according to the invention 20 advantageously guarantee good performances at dilution including a good homogeneity of the emulsion and/or dispersion of water-insoluble agricultural materials when present in the composition, generally even for high loading formulations. It has been also noted that the compositions according to the invention have 25 an adequate viscosity profile and a good pourability, which allows easier application onto soils or plants. Surprisingly no additional rheological agent, in addition to the surfactant mixture (M), is necessary to stabilize the composition. More particularly, the compositions according to the invention advantageously show: 30 - a good stability upon storage, in particular at room temperature (20°C), or even at high temperature such as during 2 weeks at 54°C; - suitable characteristics upon dilution in water at the targeted use rate; - an adequate viscosity profile and a good pourability; - satisfying tank mix compatibility properties; and/or 35 - excellent biological efficacy. As used herein, a stable composition may be defined as a composition showing no sign of destabilization such as phase separation, syneresis, flocculation, sedimentation, creaming, presence of macroscopic oil droplets at the surface of the sample. A stable composition is advantageously a formulation that do not show any 5 sign of destabilization as described above after the considered period of storage at the considered temperature. It has been challenging to achieve a concentrated pesticide formulation in the form of an oil-in-water emulsion, having suitable rheological characteristics. In order to achieve a good storage stability of such concentrated oil-in-water emulsion, the use 10 of a rheological agent bringing suspension properties is frequently used, such as xanthan gum or precipitated or precipitated or fumed silica. However, there are often compatibility issues upon tank mixing with other agrochemicals or fertilizers in presence of xanthan gum or other polysaccharide gum types. Dilution characteristics of concentrated formulations are often not satisfying, related to the presence of certain 15 rheological agents with the presence of sediments or flocs that can cause handling issues such as nozzles blocking. In addition, the use of such rheological agents to achieve good stabilization of the concentrated oil-in-water emulsions, contributes to an increase of the viscosity response generating handling issues. The composition according to the invention succeeded in obtaining suitable rheological characteristics 20 even in the form of an oil-in-water emulsion. Further, it has been noted that the compositions according to the invention can preferably guarantee good performances at dilution, even for high loading formulations, and avoid/retard the appearance of crystals, even under rigorous conditions. 25 According to a preferred embodiment of the invention, the composition is an agrochemical formulation with a high concentration of agricultural material(s). The use of concentrated formulations is in particular advantageous for economic reasons (indeed such compositions making it possible to reduce the total weight of the formulations, and consequently their transport costs), the concentrated formulation 30 then being generally diluted to the desired concentration before application in the field. A subject-matter of the invention is also a method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition onto soils and/or plants. Other characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description and the example that follows. In the present description, and unless otherwise indicated: - the expression "at least one" is equivalent to the expression "one or more" 5 and can be replaced therewith; - the expression "between" is equivalent to the expression "ranging from" and can be replaced therewith, and implies that the limits are included; - for the purposes of the present invention, the expression “greater than” and respectively the expression “less than” are intended to mean an open range which is 10 strictly greater, respectively strictly less, and therefore that the limits are not included; - the expression “alkyl” refers to an acyclic, linear or branched alkyl with a general formula of CnH2n+1; - the term “aryl” means an unsaturated hydrocarbon radical containing one or more 5- or 6-membered carbon rings, preferably 6-membered, optionally substituted 15 by one or more groups chosen from hydroxy, alkyl, alkenyl, halogen, haloalkyl, or amino; for example, phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl, and tristyrylphenyl. - the term “alkylaryl” means an aryl group substituted with one or more alkyl 20 groups, preferably with one or more (C1-C6)alkyl groups, such as, for example, phenylmethyl or phenylethyl. - the term “arylalkylaryl” means an aryl group linked to at least one alkyl group of an alkylaryl group, such as a tristyrylphenyl group. Preferably, the aryl group is linked to at least one (C1-C6)alkyl group of an alkylaryl group. 25 - by “oxyalkylenated compound”, “polyoxyalkylene compound” or “alkoxylated compound”, is meant a compound comprising ethylene oxide groups and/or propylene oxide groups and/or glycerol groups; preferably the number of ethylene oxide and/or propylene oxide groups may range from 1 to 150, and the number of glycerol groups may range from 0 to 30; more preferentially the oxyalkylenated 30 compound does not comprise any glycerol group; - the term "plants" as used herein also includes the plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait; - the term “agronomically acceptable salts” refers to salts prepared from 35 agronomically acceptable non-toxic bases or acids including inorganic or organic bases and inorganic or organic acids. Typical agronomically acceptable salts the compound referred to herein comprise an anion derived from the compound, for example, by deprotonation of a hydroxy or hydroxyalkyl substituent, and one or more positively charged counterions. Suitable positively charged counterions include inorganic cations 5 and organic cations, such as for example, sodium cations, potassium cations, calcium cations, magnesium cations, isopropylamine cations, triethanolamine cations, ammonium cations, and tetraalkylammonium cations. First herbicide 10 The composition according to the invention comprises at least one first herbicide (i) chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof. Glufosinate (CAS Reg. No.51276-47-2), with IUPAC-Name (2RS)-2-amino-15 4-[hydroxy(methyl)phosphinoyl]butyric acid, or 4-[hydroxy(methyl)phosphinoyl]- DL-homoalanine) or DL-4-[hydroxyl(methyl)phosphinoyl]-DL-homoalaninate, is known, as well as agronomically acceptable salts thereof, in particular glufosinate- ammonium (IUPAC-Name: ammonium (2RS)-2-amino-4- (methylphosphinato)butyric acid, CAS Reg. No.77182-82-2). 20 US 4,168,963 describes phosphorus-containing compounds with herbicidal activity, of which, in particular, phosphinothricin (2-amino-4- [hydroxy(methyl)phosphinoyl]butanoic acid; common name: glufosinate) and its salts have acquired commercial importance in the agrochemistry (agricultural chemistry) sector. 25 For example, glufosinate and its salts, such as glufosinate ammonium, and its herbicidal activity have been described e.g. by F. Schwerdtle et al. Z. Pflanzenkr. Pflanzenschutz, 1981, Sonderheft IX, pp.431-440. Glufosinate is represented by the following structure (I): 30 The compound of formula (I) is a racemate. Glufosinate is a racemate of two enantiomers, out of which only one shows sufficient herbicidal activity (see e.g. US 4265654 and JP92448/83). Even though various methods to prepare L-glufosinate (and respective salts) are known, the mixtures known in the art do not point at the stereochemistry, meaning that the 5 racemate is present (e.g. WO 2003024221, WO2011104213, WO 2016113334, WO 2009141367). The term “glufosinate” as used in the present invention typically comprises, in one embodiment of the invention, about 50% by weight of the L-enantiomer and 10 about 50% by weight of the D-enantiomer; and in another embodiment of the invention, more than 70% by weight of the L-enantiomer; preferably more than 80% by weight of the L-enantiomer; more preferably more than 90% of the L-enantiomer, most preferably more than 95% of the L-enantiomer. The L-enantiomer of glufosinate is also referred to as glufosinate-P. 15 Glufosinate in the form of its racemate, and its salts as well as formulations thereof, are commercially available, e.g. under the trade-names BastaTM and LibertyTM. In one embodiment, the first herbicide compound is selected from racemic 20 glufosinate mixtures as described above, wherein the glufosinate comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer. In another embodiment, the first herbicide compound is glufosinate, wherein at least 70% by weight of the glufosinate is L-glufosinate or a salt thereof. 25 L-glufosinate, with IUPAC-Name (2S)-2-amino-4- [hydroxy(methyl)phosphinoyl]butyric acid (CAS Reg. No. 35597-44-5) and also called glufosinate-P, can be obtained commercially or may be prepared for example as described in WO2006/104120, US5530142, EP0248357A2, EP0249188A2, 30 EP0344683A2, EP0367145A2, EP0477902A2, EP0127429 and J. Chem. Soc. Perkin Trans.1, 1992, 1525-1529. L-Glufosinate as used in the present invention comprises more than 70% by weight of the L-enantiomer; preferably more than 80% by weight of the L-enantiomer; more preferably more than 90% of the L-enantiomer, most preferably more than 95% of the L-enantiomer and can be prepared as referred to above. Preferably, the salts of glufosinate or L-glufosinate are the sodium, potassium or ammonium (NH4+) salts of glufosinate or L-glufosinate, in particular glufosinate-P- ammonium (IUPAC-Name: ammonium (2S)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.73777-50-1), glufosinate-P-sodium (IUPAC-Name: sodium (2S)- 2-amino-4-(methylphosphinato)butyric acid; CAS Reg. No. 70033-13-5) and glufosinate-P-potassium (IUPAC-Name: potassium (2S)-2-amino-4- (methylphosphinato)butyric acid) for L-glufosinate. In a particular group of embodiments, the first herbicide compound comprises a glufosinate salt, which is selected from the group consisting of the sodium, potassium or ammonium (NH4+) salts of glufosinate. Hence, the first herbicide compound preferably comprises or is L-glufosinate- ammonium or L-glufosinate-sodium or L-glufosinate-potassium and L-glufosinate as free acid. Especially preferred is L-glufosinate-ammonium, i.e. the ammonium (NH4+) salt of glufosinate. In a particular group of embodiments, the first herbicide compound is a L- glufosinate salt, which is in particular selected from the group consisting of the sodium, potassium and ammonium (NH4+) salts of L-glufosinate. Even more preferably, the first herbicide compound is a L-glufosinate salt, which is selected from the group consisting of glufosinate-P-ammonium, glufosinate-P-sodium and glufosinate-P- potassium. Especially, the first herbicide compound is an ammonium salt of L- glufosinate. The following are examples of suitable compounds of formula (I): I.1: enantiopure L-glufosinate I.1.a: enantiopure L-glufosinate-ammonium I.1.b: enantiopure L-glufosinate-sodium I.1.c: enantiopure L-glufosinate-potassium I.2: mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ≥ 95 and Y ≤ 5 % and wherein X + Y are 100. I.2.a: mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ≥ 95 and Y ≤ 5 and wherein X + Y are 100. I.2.b: mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ≥ 95 and Y ≤ 5 and wherein X + Y are 100. 5 I.2.c: mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ≥ 95 and Y ≤ 5 and wherein X + Y are 100. I.3: mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ≥ 90 and Y ≤ 10 and wherein X + Y are 100. I.3.a: mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- 10 glufosinate-ammonium, wherein X ≥ 90 and Y ≤ 10 and wherein X + Y are 100. I.3.b: mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ≥ 90 and Y ≤ 10 and wherein X + Y are 100. I.3.c: mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ≥ 90 and Y ≤ 10 and wherein X + Y are 100. 15 I.4: mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ≥ 80 and Y ≤ 20 and wherein X + Y are 100. I.4.a: mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ≥ 80 and Y ≤ 20 and wherein X + Y are 100. I.4.b: mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- 20 sodium, wherein X ≥ 80 and Y ≤ 20 and wherein X + Y are 100. I.4.c: mixture of X% w/w L-glufosinate-potassium and Y% w/w D- glufosinate-potassium, wherein X ≥ 80 and Y ≤ 20 and wherein X + Y are 100. I.5: mixture of X% w/w L-glufosinate and Y% w/w D-glufosinate, wherein X ≥ 70 and Y ≤ 30 and wherein X + Y are 100. 25 I.5.a: mixture of X% w/w L-glufosinate-ammonium and Y% w/w D- glufosinate-ammonium, wherein X ≥ 70 and Y ≤ 30 and wherein X + Y are 100. I.5.b: mixture of X% w/w L-glufosinate-sodium and Y% w/w D-glufosinate- sodium, wherein X ≥ 70 and Y ≤ 30 and wherein X + Y are 100. I.5.c: mixture of X% w/w L-glufosinate-potassium and Y% w/w D- 30 glufosinate-potassium, wherein X ≥ 70 and Y ≤ 30 and wherein X + Y are 100. More preferentially, the first herbicide(s) (i) are chosen from L-glufosinate or an agronomically acceptable salt thereof. Advantageously, the first herbicide(s) (i) is water-soluble, and/or comprised in the aqueous phase of the composition according to the invention. Preferably, the total amount of the first herbicide(s) (i) is from 10 to 600 g/L 5 (gram of first herbicide(s) (i) per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 200 g/L, relative to the total amount of the composition. Preferably, the total amount of glufosinate is from 10 to 600 g/L (gram of glufosinate per liter of composition), more preferentially from 50 to 500 g/L, even 10 more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 200 g/L, relative to the total amount of the composition. Preferably, the total amount of L-glufosinate is from 10 to 600 g/L (gram of glufosinate per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better 15 from 100 to 200 g/L, relative to the total amount of the composition. Preferably, the total content of the first herbicide(s) (i) ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the 20 total weight of the composition. Preferably, the total content of glufosinate ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the total weight of the composition. 25 Preferably, the total content of L-glufosinate ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 10% to 25% by weight, relative to the total weight of the composition. 30 Second herbicide The composition according to the invention comprises at least one second herbicide (ii) chosen from dimethenamid, dimethenamid-P, or mixtures thereof. The second herbicide(s) (ii) are Very-Long-Chain Fatty Acids (VLCFA) inhibitors. Herbicides that act by inhibiting the biosynthesis of very-long-chain fatty acids have been used to control grass weeds in major crops throughout the world for the past 60 years. VLCFA-inhibiting herbicides are generally highly selective in crops, 5 induce similar symptoms in susceptible grasses and can be found within the herbicide groups classified by the HRAC as K3 and N. Dimethenamid (CAS Reg. No. 87674-68-8), with IUPAC-Name (RS)-2- chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide is known. 10 For example, dimethenamid has been described by J. Harr et al., Proc. Br. Crop Prot. Conf. – Weeds 1991, 87-92 and A. Rahman, T. K. James, Proc.45th N. Z. Plant Prot. Conf.1992, 84-88. Dimethenamid in the form of its racemate, is commercially available, e.g. under the trade-names Pestanal® by Merck. 15 Dimethenamid is represented by the following structure (II):
Figure imgf000012_0001
The compound of formula (II) is a racemate. Dimethenamid-P (CAS Reg. No.163515-14-8), with IUPAC-Name (S)-2- 20 Chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide is known. For example, dimethenamid-P has been described by T. Guillet et al., Phytom 546, 50-53 (2002). Dimethenamid-P is commercially available, e.g. under the trade-names Isard® or Outlook® by BASF. 25 Dimethenamid-P is represented by the following structure (III):
Figure imgf000012_0002
Preferably, the composition comprises dimethenamid-P. Advantageously, the second herbicide(s) (ii) is water-insoluble, and/or comprised in the oily phase of the composition according to the invention. 5 Preferably, the total amount of second herbicide(s) (ii) is from 10 to 600 g/L (gram of second herbicide(s) (ii) per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 10 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition. Preferably, the total amount of dimethenamid is from 10 to 600 g/L (gram of dimethenamid per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition. 15 Preferably, the total amount of dimethenamid-P is from 10 to 600 g/L (gram of dimethenamid-P per liter of composition), more preferentially from 50 to 500 g/L, even more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition. 20 Preferably, the total content of second herbicide(s) (ii)ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition. Preferably, the total content of dimethenamid ranges from 1% to 50% by 25 weight, more preferentially from 5% to 40% by weight, even more preferentially from 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition. Preferably, the total content of dimethenamid-P ranges from 1% to 50% by weight, more preferentially from 5% to 40% by weight, even more preferentially from 30 10% to 30% by weight, even better from 15% to 25% by weight, relative to the total weight of the composition. Preferably, the weight ratio of the total amount of first herbicide(s) (i) to the total amount of second herbicide(s) (ii) ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1. Preferably, the weight ratio of the total amount of glufosinate to the total amount of dimethenamid ranges from 0.1 to 5; more preferably from 0.125 to 4; more 5 preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1. Preferably, the weight ratio of the total amount of glufosinate to the total amount of dimethenamid-P ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 10 1.5, and even better from 0.5 to 1. Preferably, the weight ratio of the total amount of L-glufosinate to the total amount of dimethenamid ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1. 15 Preferably, the weight ratio of the total amount of L-glufosinate to the total amount of dimethenamid-P ranges from 0.1 to 5; more preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1. 20 The anionic surfactant (iii) The composition according to the invention comprises at least one anionic surfactant (iii). The term "anionic surfactant" is understood to mean a surfactant comprising, 25 as ionic or ionizable groups, only anionic groups. In the present description, an entity is described as being "anionic" when it possesses at least one permanent negative charge or when it can be ionized to give a negatively charged entity, under the conditions of use of the composition of the invention (medium or pH, for example), and not comprising a cationic charge. 30 The anionic surfactants (iii) are adjuvants, which can be chosen from sulfate, sulfonate and carboxylic (or carboxylate) surfactants. Very obviously, a mixture of these surfactants can be employed. It is understood, in the present description, that: - the carboxylate anionic surfactants comprise at least one carboxyl or carboxylate (-COOH or -COO-) functional group and can optionally additionally comprise one or more sulfate and/or sulfonate functional groups; - the sulfonate anionic surfactants comprise at least one sulfonate (-SO3H or - SO3–) functional group and can optionally additionally comprise one or more sulfate functional groups, but do not comprise a carboxylate functional group; and - the sulfate anionic surfactants comprise at least one sulfate functional group but do not comprise a carboxylate or sulfonate functional group. By way of examples of anionic surfactants, mention may be made without any intended limitation thereto, of: - alkylsulfonic acids, arylsulfonic acids, optionally substituted with one or more hydrocarbon groups, and the acid function of which is partly or totally salified, like C8-C50 alkylsulfonic acids, more particularly C8-C30, preferably C10-C22 alkylsulfonic acids, benzenesulfonic acids, naphthalenesulfonic acids, substituted with one to three C1-C30, preferably C4-C16 alkyl and/or C2-C30, preferably C4-C16 alkenyl groups, - mono- or di-esters of alkylsulfosuccinic acids, of which the linear or branched alkyl portion is optionally substituted with one or more linear or branched C2-C4 hydroxylated and/or oxyalkylenated (preferably ethoxylated, propyxylated, ethopropoxylated) groups, - phosphate esters more particularly selected from among those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group, comprising 8 to 40 carbon atoms, preferably 10 to 30, optionally substituted with at least one oxyalkylenated (ethoxylated, propoxylated, ethopropoxylated) group. In addition, they comprise at least one phosphate ester group, mono- or di-esterified such that it is possible to have one or two free or partly or totally salified groups. The preferred phosphate esters are of the type of the mono- and di-esters of phosphoric acid and of oxyalkylenated (ethoxylated and/or propoxylated) mono-, di- or tri- styrylphenol, or oxyalkylenated (ethoxylated and/or propoxylated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; of phosphoric acid and of an oxyalkylenated (ethoxylated or ethopropoxylated) C8-C30, preferably C10-C22 alcohol; of phosphoric acid and of a non-oxyalkylenated C8-C22, preferably C10- C22 alcohol, - sulfate esters obtained from saturated or aromatic alcohols optionally substituted with one or more oxyalkylenated (ethoxylated, propoxylated, ethopropoxylated) groups, and for which the sulfate functions appear in the free acid form, or are partly or totally neutralised. As an example, mention may be made of sulfate esters more particularly obtained from saturated or unsaturated C8-C20 alcohols, which may comprise 1 to 8 oxyalkylenated (ethoxylated, propoxylated, ethopropoxylated) units ; sulfate esters obtained from oxyalkylenated phenol, substituted with 1 to 3 saturated or unsaturated C2-C30 hydroxycarbon groups, and in which the number of oxyalkylenated units is comprised between 2 and 40 ; the sulfate esters obtained from oxyalkylenated mono-, di- or tri-styrylphenol in which the number of oxyalkylenated units varies from 2 to 40. The anionic surfactants may be in the acid form (they are potentially anionic), or in a partly or totally salified form with one counter-ion. The counter-ion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or moreover even an ammonium ion of formula N(R)4+ in which the R groups, either identical or different, represent a hydrogen atom or a C1-C4 alkyl group optionally substituted with an oxygen atom. Advantageously, the anionic surfactant(s) (iii) are chosen from sulfate anionic surfactants. The sulfate anionic surfactants that may be used comprise at least one sulfate (-OSO3H or -OSO3-) functional group. The sulfate anionic surfactants can be chosen from the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates; and also the salts of these compounds. The alkyl groups of these compounds comprising from 6 to 30 carbon atoms, in particular from 8 to 28, better still from 10 to 24, indeed even from 12 to 22, carbon atoms; the aryl group preferably denoting a phenyl or benzyl group. It being possible for these compounds to be oxyalkylenated, in particular oxyethylenated, and then preferably comprising from 1 to 50 ethylene oxide units, better still from 1 to 10 ethylene oxide units. Preferably, the anionic surfactant(s) (iii) are chosen from alkyl ether sulfates. More preferentially, the anionic surfactant(s) (iii) are chosen from those of formula (IV): [R-O-(A-O)n-SO3]- M+ (IV) in + which M is a cation; A is C2-C3 alkandiyl; R is selected from linear or branched C10-C20 alkyl, preferably C12-C14 alkyl, and mixtures thereof; and n is a natural positive number of 1 to 12 where the number average of n is in the range of 1 to 10. The compound of formula (IV) is an alkyl ether sulfate salt having C10-C20- alkyl as alkyl rest, a linker -(A-O)n- formed by 1 to 12, on average 1 to 10, C2-C3- alkylene oxide unit(s) A-O between C10-C20-alkyl and sulfate group, and a cation M+ as counterion. In this context of formula (IV), the term “C10-C20-alkyl” refers to linear or branched saturated alkyl radicals generally having from 10 to 20 carbon atoms (C10- C20-alkyl), in particular 12 to 18 carbon atoms (C12-C18-alkyl). Suitable examples of C10-C20-alkyl include, but are not limited to decanyl, isodecyl, 2-propylheptyl, undecanyl, dodecyl, tridecyl, isotridecyl, tetramethylnonyl, ethyldimethylnonyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, including the linear isomers, such as n-decanyl, n-undecyl, n- dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- octadecyl, n-nonadecyl and n-eicosyl, and the branched isomers thereof, also termed iso-isomers, such as isodecyl, e. g. 2-methyl-1-nonyl, 8-methyl-1-nonyl, 3,5- dimethyloctyl, 5,7-dimethyloctyl, 2,4,6-trimethylheptyl, 2-propylheptyl, isoundecyl, e. g. 2-methyldecyl, 9-methyldecyl, the dimethylnonyl isomers, the trimethyloctyl isomers, the tetramethylheptyl isomers and the ethyldimethylnonyl isomers; iso- dodecyl, e. g. 2-methylundecyl, 10-methylundecyl, 2-butyloctyl, the dimethyldecyl isomers, the trimethylnonyl isomers and the tetramethyloctyl isomers; isotridecyl, e. g. 2-methyldodecyl, 11-methyldodecyl, the dimethylundecyl isomers, the trimethyldecyl isomers, the tetramethylnonyl isomers, such as 2,4,6,8-tetramethyl-1-nonyl, 3,4,6,8- tetramethyl-1-nonyl, the pentamethyloctyl isomers and 5-ethyl-4,7-dimethyl-1-nonyl; isotetradecyl, e. g. 2-methyltridecyl, 12-methyltridecyl, 2-pentylnonyl, the dimethyldodecyl isomers, the trimethylundecyl isomers, the tetramethyldecyl isomers and the pentamethylnonyl isomers; isopentadecyl; isohexadecyl; isoheptadecyl; isooctadecyl such as 2-octyldecyl; isononadecyl; and isoeicosyl. In a preferred embodiment, R is C12-C14. The terms “C2-C3-alkylene” and “C2-C3-alkandiyl” are used synonymously 5 and refer to linear or branched divalent alkyl radicals having from 2 or 3 carbon atoms, such as 1,2-ethanediyl and 1,2-propanediyl. Preferred is 1,2-ethanediyl. The variable n in the formula (IV) is natural positive number of 1 to 10, in particular in the range of 1 to 8, especially in the range of 1 to 7, i. e. n is 1, 2, 3, 4, 5, 6 or 7. The compound of the formula (IV) is typically a mixture of compounds with 10 different n. The average of n is typically in the range of 1 to 10, in particular in the range of 1 to 8, preferably in the range of 1 to 7, more preferably in the range of 1 to 6, even more preferably in the range of 1 to 5, still more preferably in the range of 1.5 to 5. Any reference to average of n refers to the number average of the repeating units A-O per molecule, i. e. to the relative molar amounts of repeating units A-O with 15 respect to R, i. e. the average is the number average. In the compounds of the formula (IV) the radicals R may be identical, i. e. all molecules or at least 95 mol-% of the molecules of the formula (IV) have the same group R. In the compounds of the formula (IV) the radicals R may be different, i.e. the compounds of the formula (IV) are mixtures of compounds having different radicals 20 R. The difference of R may result from different isomers of the respective radical R having the same number of carbon atoms or from differences in the number of carbon atoms in the radical R or from both. In particular, the radical R comprises at least 40% by weight, more particularly at least 50% by weight, or up to 100% by weight, based on the total weight 25 alkyl radicals R present in the compounds of the formula (IV), of alkyl radicals R having 12 to 14 carbon atoms (C12-C14-alkyl). In the compounds of formula (IV) the cation M+ may be any cation suitable for agricultural purposes. The cation may be monovalent, i.e. it bears a single cationic charge, or polyvalent, i.e. it bears more than one cationic charge. In this case, M+ refers 30 to the cation equivalent of the cation. Suitable cations include alkali metal cations, such as sodium or potassium ions, alkaline earth metal cations, such as calcium ion, ammonium (NH4+), and cations based on organic amines. Preferably, M+ refers to monovalent cation. Suitable examples of the cation M+ are, but not limited to alkali metal cations 35 such as sodium, potassium and lithium cations, and substituted or unsubstituted ammonium cations, for example NH4+ (ammonium), hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium cations, 2- hydroxypropylammonium, di(2-hydroxypropyl)ammonium and tri(2- hydroxypropyl)ammonium cations. In an embodiment, the cation M+ is H4-mNR1m+, where R1 is selected from the group consisting of alkyl radicals having preferably 1 to 4 carbon atoms, OH substituted alkyl radicals having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3. In an embodiment, the cation M+ is selected from the group consisting of hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium cations, 2-hydroxypropylammonium, di(2-hydroxypropyl)ammonium and tri(2- hydroxypropyl)ammonium cations. In a particularly preferred embodiment, compound of formula (IV) is sodium C12-C14 ether sulfate. In another particularly preferred embodiment, compound of formula (IV) is sodium lauryl ether sulfate. In another particularly preferred embodiment, compound of formula (IV) is hydroxyethylammonium lauryl ether sulfate. Even more preferentially, the anionic surfactant(s) (iii) are chosen from salts of (C12-C14)alkyl ether sulfate; even better from sodium lauryl ether sulfate, hydroxyethylammonium lauryl ether sulfate, and mixtures thereof. Preferably, the anionic surfactant(s) (iii) are comprised in the aqueous phase of the composition. Preferably, the total amount of anionic surfactant(s) (iii) is from 1 to 300 g/L (gram of anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount of the composition. Preferably, the total amount of sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of sulfate anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount of the composition. Preferably, the total amount of alkyl ether sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of alkyl ether sulfate anionic surfactant (s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to 5 the total amount of the composition. Preferably, the total amount of anionic surfactant(s) of formula (IV) is from 1 to 300 g/L (gram of anionic surfactant(s) (iii) of formula (IV) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better from 120 to 180 g/L, relative to the total amount 10 of the composition. Preferably, the total amount of (C12-C14)alkyl ether sulfate anionic surfactant(s) is from 1 to 300 g/L (gram of (C12-C14)alkyl ether sulfate anionic surfactant(s) (iii) per liter of composition), more preferentially from 30 to 250 g/L, even more preferentially from 80 to 220 g/L, better from 100 to 200 g/L, even better 15 from 120 to 180 g/L, relative to the total amount of the composition. Preferably, the total content of anionic surfactant(s) (iii) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better 20 from 11% to 16% by weight, relative to the total weight of the composition. Preferably, the total content of sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition. 25 Preferably, the total content of alkyl ether sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition. 30 Preferably, the total content of anionic surfactant(s) of formula (IV) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the total weight of the composition. Preferably, the total content of (C12-C14)alkyl ether sulfate anionic surfactant(s) ranges from to 1% to 30% by weight, more preferably from 3% to 30% by weight, more preferentially from 7% to 20% by weight, even more preferentially from 9% to 18% by weight, even better from 11% to 16% by weight, relative to the 5 total weight of the composition. The surfactant mixture (M) The composition according to the invention comprises a surfactant mixture 10 (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates of ethylene oxide and of propylene oxide, and c. at least one phosphate ester surfactant. 15 Preferably, the surfactant mixture (M) is in the oily phase of the composition. According to the invention, the anionic surfactant(s) (iii) are not part of said surfactant mixture (M). More preferentially, the anionic surfactant(s) (iii) is in the aqueous phase of 20 the composition, and/or the surfactant mixture (M) is in the oily phase. The surfactant mixture (M) comprises at least one non-ionic surfactant a) chosen from oxyalkylenated fatty alcohols, preferably from oxyethylenated fatty alcohols. 25 Preferentially, the oxyalkylenated fatty alcohols that may be used comprise: - a linear or branched hydrocarbon chain having from 8 to 30, better from 10 to 20, even better from 10 to 14 carbon atoms, and - from 1 to 50, better from 2 to 15, even better from 5 to 10 alkylene oxide groups, for instance ethylene and/or propylene oxide groups, 30 more preferentially ethylene oxide groups. Useful non-ionic surfactants a) are in particular the following products, all marketed by Solvay: - Rhodasurf® BC 610: ethoxylated tridecyl alcohol, 6EO - Rhodasurf® 860/P: ethoxylated isodecyl alcohol, 6 EO - Rhodasurf® TDA 8.5: ethoxylated isotridecyl alcohol, 8.5 EO - Rhodasurf® BC 630: ethoxylated tridecyl alcohol, 7 EO - Rhodasurf® BC 720: ethoxylated tridecyl alcohol, 10 EO 5 - Rhodasurf® BC 840: ethoxylated tridecyl alcohol, 15 EO. Preferably, the Hydrophilic-Lipophilic Balance (HLB) of the oxyalkylenated fatty alcohols a) ranges from 8 to 16; more preferentially from 9 to 15; better from 10 to 14; or even better from 11 to 13. 10 The HLB being the ratio of the hydrophilic part to the lipophilic part in the surfactant. The term “HLB” is well known to a person skilled in the art and is described, for example, in “The HLB system. A time-saving guide to Emulsifier Selection” (published by ICI Americas Inc., 1984). For the present invention, the HLB of the ionic surfactants is preferably determined by Davies’ method, and the HLB of 15 the non-ionic surfactants is preferably determined by Griffin’s method. According to a preferred embodiment of the invention, the non-ionic surfactants a) are chosen from oxyethylenated fatty alcohols. More preferentially, the non-ionic surfactants a) are chosen from oxyethylenated fatty alcohols comprising 20 from 8 to 30, better from 10 to 20, even better from 10 to 14 carbon atoms and from 1 to 50, preferentially from 1 to 30, better from 2 to 15, even better from 5 to 10, and still better from 5 to 7 ethylene oxide groups. Preferably, the total amount of oxyalkylenated fatty alcohol(s) a) is from 1 to 25 60 g/L (gram of oxyalkylenated fatty alcohol(s) per liter of composition), preferentially from 2 to 50 g/L, more preferentially from 5 to 40 g/L, even more preferentially from 10 to 30 g/L, better from 12 to 25 g/L, and even better from 13 to 20 g/L, relative to the total amount of the composition. Preferably, the total amount of oxyethylenated fatty alcohol(s) a) is from 1 to 30 60 g/L (gram of oxyethylenated fatty alcohol(s) per liter of composition), preferentially from 2 to 50 g/L, more preferentially from 5 to 40 g/L, even more preferentially from 10 to 30 g/L, better from 12 to 25 g/L, and even better from 13 to 20 g/L, relative to the total amount of the composition. Preferably, the total content of oxyalkylenated fatty alcohol(s) a) ranges from 0.1% to 10% by weight, more preferentially from 0.5% to 5% by weight, even more preferentially from 1% to 4% by weight, even better from 1% to 3% by weight, relative to the total weight of the composition. 5 Preferably, the total content of oxyethylenated fatty alcohol(s) a) ranges from 0.1% to 10% by weight, more preferentially from 0.5% to 5% by weight, even more preferentially from 1% to 4% by weight, even better from 1% to 3% by weight, relative to the total weight of the composition. 10 The surfactant mixture (M) comprises at least one non-ionic surfactant b) chosen from polycondensates of ethylene oxide and of propylene oxide. Preferably, the non-ionic surfactants b) are chosen from di- or tri-block 15 polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide. For example the non-ionic surfactants are block polymers, of the A-B type, the A-B-A type or the B-A-B type comprising blocks of polyethylene oxide (unit A) and propylene oxide (unit B), or of the A-B-C type, the A-B-A-C type, the B-A-B-C 20 type, the C-A-B-A-C type or the C-B-A-B-C type comprising polyethylene oxide, polypropylene oxide and (C1-C8)alkanol or hydroxy(alkyl)aryl group(s) (unit C). The mean molar mass is advantageously at least 950g/mol, preferably at least 2000g/mol, typically between 2000 g/mol and 7000g/mol, more preferentially between 2000 g/mol and 4000g/mol. The polyethylene oxide content is advantageously at least 25 10% by weight, preferably at least 20% by weight, even more preferably at least 40% by weight of the polycondensate of ethylene oxide and of propylene oxide. According to a preferred embodiment of the invention, the polycondensates of ethylene oxide and propylene oxide that may be used in the composition according to the invention have a mean molar mass ranging from 850 to 15000, and more 30 preferably ranging from 1200 to 10000, more preferably ranging from 1500 to 6500, and still more preferably ranging from 1500 to 5000 g/mol. Preferably, the non-ionic surfactants b) are chosen from polycondensates of ethylene oxide and of propylene oxide of formula (V): 35 R-(O-CH2-CH2)a–(O-CH(CH3)-CH2)b–(O-CH2-CH2)a’–(O-CH(CH3)-CH2)b’–O–R’ (V) in which: 5 R and R’ are each independently H, alkyl, aryl, alkylaryl or arylalkylaryl; wherein R and/or R’ may comprise a carbonyl to form an ester function with the rest of the polymer, preferably R and R’ are H; a is an integer between 0 and 150, a’ is an integer between 2 and 150, 10 b is an integer between 1 and 100, b’ is an integer between 0 and 100, and when a is not equal to 0, then b’ is 0 and a is preferably between 2 and 150, and when b’ is not equal to 0, then a is 0 and b’ is preferably between 2 and 100. 15 According to one embodiment of the invention, a in formula (V) is 0. According to another embodiment of the invention, b’ in formula (V) is 0. According to a particular embodiment of the invention, both a and b’ in formula (V) are 0. 20 According to a preferred embodiment of the invention, in formula (V), R and R’ both denote an hydrogen atom and b’ is 0. More preferentially, the polycondensates of ethylene oxide and of propylene oxide b) are chosen from poloxamers. 25 As used herein, a “poloxamer” is a non-ionic triblock copolymer comprising a central hydrophobic chain of polyoxypropylene (i.e. poly(propylene oxide)) flanked by two hydrophilic chains of polyoxyethylene (i.e. poly(ethylene oxide)). According to a preferred embodiment of the invention, the non-ionic surfactant(s) b) are poloxamers chosen from Poloxamer 101, Poloxamer 105, 30 Poloxamer 108, Poloxamer 122, Poloxamer 123, Poloxamer 124, Poloxamer 181, Poloxamer182, Poloxamer 183, Poloxamer 184, Poloxamer 185, Poloxamer 188, Poloxamer 212, Poloxamer 215, Poloxamer 217, Poloxamer 231, Poloxamer 234, Poloxamer 235, Poloxamer 237, Poloxamer 238, Poloxamer 282, Poloxamer 284, Poloxamer 288, Poloxamer 331, Poloxamer 333, Poloxamer 334, Poloxamer 335, Poloxamer 338, Poloxamer 401, Poloxamer 402, Poloxamer 403, Poloxamer 407, Poloxamer 105 benzoate, Poloxamer 182 dibenzoate, and mixtures thereof. According to a more preferred embodiment of the invention, the composition comprises, as non-ionic surfactant b), at least one poloxamer having a mean molar 5 mass between 2500 and 3000 g/mol, and a polyethylene oxide content between 20% and 50% by weight, for example Poloxamer 184 such as Antarox® L64 marketed by Solvay. Preferably, the Hydrophilic-Lipophilic Balance (HLB) of the oxyalkylenated 10 fatty alcohols a) ranges from 4 to 20; more preferentially from 8 to 18; even better from 12 to 18; for instance 15. Preferably, the total amount of polycondensate(s) of ethylene oxide and propylene oxide b) is from 5 to 200 g/L (gram of polycondensate(s) per liter of 15 composition), more preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition. Preferably, the total amount of di- or tri-block polymer(s), wherein the polymeric moiety being composed of ethylene oxide and propylene oxide, is from 5 to 200 g/L (gram of said di- or tri-block polymer(s) per liter of composition), more 20 preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition. Preferably, the total amount of polycondensate(s) of ethylene oxide and propylene oxide of formula (V) is from 5 to 200 g/L (gram of polycondensate(s) per liter of composition), more preferentially from 7 to 100 g/L, even more preferentially 25 from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the total amount of the composition. Preferably, the total amount of poloxamer(s) is from 5 to 200 g/L (gram of poloxamer(s) per liter of composition), more preferentially from 7 to 100 g/L, even more preferentially from 10 to 50 g/L, even better from 15 to 35 g/L, relative to the 30 total amount of the composition. Preferably, the total content of polycondensate(s) of ethylene oxide and propylene oxide b) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better 35 from 1% to 4% by weight, relative to the total weight of the composition. Preferably, the total content of di- or tri-block polymer(s), wherein the polymeric moiety being composed of ethylene oxide and propylene oxide, ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, 5 relative to the total weight of the composition. Preferably, the total content of polycondensate(s) of ethylene oxide and propylene oxide of formula (V) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, relative to the total weight of the 10 composition. Preferably, the total content of poloxamer(s) ranges from 0.4% to 20% by weight, more preferentially from 0.6% to 9% by weight, even more preferentially from 0.8% to 5% by weight, even better from 1% to 4% by weight, relative to the total weight of the composition. 15 The surfactant mixture (M) comprises at least one surfactant c) chosen from phosphate ester surfactants. According to the invention, the phosphate ester surfactant(s) c) are different 20 from selected anionic surfactants (iii) and non-ionic surfactants a) described above. Phosphate ester surfactants are generally known. The phosphate esters as surfactants c) can be more particularly selected from among those comprising: 1) at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group, comprising 8 to 70 carbon atoms, preferably 10 to 40, optionally substituted with at 25 least one oxyalkylenated group (ethoxylated, propoxylated, ethopropoxylated group), and 2) at least one phosphate ester group, mono- or di-esterified such that it is possible to have one or two free or partly or totally salified groups. Suitable phosphate ester surfactants that may be cited are, for example, butyl phosphate, ethoxylate butyl phosphate, dibutyl phosphate, ethoxylated dibutyl30 phosphate, hexyl phosphate, dihexyl phosphate, 2-ethylhexylphosphate, di-2- ethylhexyl phosphate, octyl phosphate, ethoxylated octyl phosphate dioctyl phosphate, ethoxylated dioctyl phosphate, decyl phosphate, didecyl phosphate, stearyl phosphate, ethoxylated stearyl phosphate, distearyl phosphate, ethoxylated distearyl phosphate and mixtures thereof. 35 Preferably, the phosphate ester surfactant(s) may be chosen from those of formula (VI) above or an agronomically acceptable salt thereof:
Figure imgf000027_0001
wherein: * R1 and R2 are each independently H, alkyl, alkenyl, aryl, alkylaryl or arylalkylaryl; provided that at least one of R1 and R2 is alkyl, alkenyl, aryl, alkylaryl or arylalkylaryl, * m and m′ are each independently 2, 3, or 4; provided, if n is greater than 1, that m may differ independently for each (CmH2mO) repeat unit, and if n′ is greater than 1, that m′ may differ independently for each (Cm′H2m′O) repeat unit, and * n and n′ are each independently 0 or an integer of from 1 to about 25. In one particular embodiment, R1 and R2 are each independently H, (C4- C22)alkyl, (C4-C22)alkenyl, (C1-C6)alkylaryl or aryl(C1-C6)alkylaryl. According to a preferred embodiment of the invention, R1 and R2 are each independently H, (C8-C18)alkyl, or aryl(C1-C6)alkylaryl. More preferentially, at least R1 is aryl(C1-C6)alkylaryl such as a tristyrylphenyl group. In another embodiment, n and n′ are each independently 0 or an integer of from 10 to 22, preferably n and n′ are an integer of from 14 to 22, more preferentially from 14 to 18. More preferentially, the phosphate ester surfactant(s) c) are chosen from: - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol; - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) C8-C30 (preferentially C10-C22, better C10-C18) aliphatic alcohol; - the mono- and di-esters of phosphoric acid and of non-oxyalkylenated C8-C30 (preferentially C10-C22, better C10-C18) aliphatic alcohol; - salts thereof, and - mixtures thereof. 5 Even more preferentially, the phosphate ester surfactant(s) c) are chosen from: - the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol; - the mono- and di-esters of phosphoric acid and of oxyalkylenated 10 (preferentially oxyethylenated) C8-C30 (preferentially C10-C22, better C10-C18) aliphatic alcohol; - salts thereof, and - mixtures thereof. 15 More preferentially, the phosphate ester surfactant(s) c) are in salt form. More particularly, the phosphate ester surfactant(s) c) are salified with a suitable base. Suitable bases include sodium, potassium, lithium, ammonium hydroxides and amines; preferably alkanolamines such as triethanolamine, diethanolisopropanolamine and diglycoldiisopropanolamine. The salts of the phosphate esters may be of any suitable 20 base:acid molar ratio salts, such as those ranging from 0.7 to 1.7, as dictated by the properties of the salt. According to a preferred embodiment of the invention, the phosphate ester surfactant(s) c) are chosen from the mono- and di-esters of phosphoric acid and of 25 oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, neutralized with triethanolamine salt. According to another preferred embodiment of the invention, the phosphate ester surfactant(s) c) are chosen from ethoxylated tri-styrylphenol phosphates, acidic form, such as for example Soprophor® 3D33, Dispersogen® LFH. 30 According to a particularly preferred embodiment of the invention, the phosphate ester surfactant(s) c) are chosen from ethoxylated tri-styrylphenol phosphates neutralized with triethanolamine salt, such as Soprophor® FL, Dispersogen® LFS. Preferably, the total amount of phosphate ester surfactant(s) c) is from 5 to 150 g/L (gram of phosphate ester surfactant(s) c) per liter of composition), more preferentially from 10 to 100 g/L, even more preferentially from 15 to 50 g/L, even better from 20 to 30 g/L, relative to the total amount of the composition. 5 Preferably, the total amount of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, preferably neutralized with triethanolamine salt, is from 5 to 150 g/L (gram of ester(s) per liter of composition), more preferentially from 10 to 100 g/L, even more preferentially from 15 to 50 g/L, even better from 20 to 30 g/L, relative to the total 10 amount of the composition. Preferably, the total content of phosphate ester surfactant(s) c) ranges from 0.4% to 15% by weight, more preferentially from 0.9% to 10% by weight, even more preferentially from 1.2% to 5% by weight, even better from 1.5% to 3.5% by weight, 15 relative to the total weight of the composition. Preferably, the total content of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol, preferably neutralized with triethanolamine salt, ranges from 0.4% to 15% by weight, more preferentially from 0.9% to 10% by weight, even more preferentially from 1.2% 20 to 5% by weight, even better from 1.5% to 3.5% by weight, relative to the total weight of the composition. Advantageously, the surfactant mixture (M) is comprised in the oily phase of the composition according to the invention. 25 According to a particular embodiment, the composition according to the invention does not contain any rheological agent nor suspension agent nor thickener agent, such as xanthan gum, precipitated or fumed silica, or clay such as attapulgite. 30 According to the invention, the composition is preferably for agricultural use. The composition according to the invention may further comprise at least one additional agricultural material, other than dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof. Agriculture uses many agricultural materials. They are also referred to as active plant-protection products or active materials or active substances. As used herein, the term “agricultural material” means an active ingredient used in particular to the practice of farming, including cultivation of the soil for the growing of crops. However, the use of agricultural materials is not limited to application to crops. Agricultural materials may be applied to any surface, e.g., for the purpose of cleaning or aiding or inhibiting growth of a living organism. Other non- crop applications include, but are not limited to, application to an animal, e.g. livestock, application to turf and ornamentals, and application to railroad weed. Agricultural materials are generally products in pure or highly concentrated form, generally not soluble in water and known to the person skilled in the art. Depending on the water solubility of the agricultural materials and their loading in the targeted formulation, it can be very challenging to identify suitable solvents to obtain a chemically and physically stable formulation. For agricultural materials with a low or relatively low water solubility, the use of appropriate solvents is therefore interesting to prepare concentrated liquid formulations. Such concentrated formulations of agricultural materials are generally diluted prior to agricultural use. The dilution effected by the farmer is generally performed by mixing the agrochemical formulation with water. Preferably, the additional agricultural materials are water-insoluble agricultural materials, at 25°C and at atmospheric pressure (i.e., 1.013x105 Pa). More preferentially, the water solubility of the additional agricultural material is strictly less than 100 g/L, even more preferentially strictly less than 20 g/L, in particular strictly less than 5 g/L, for instance strictly less than 1 g/L and even strictly less than 0.2 g/L, at 25°C and at atmospheric pressure (i.e., 1.013x105 Pa). According to one particular embodiment of the invention, the additional agricultural materials are water-soluble agricultural materials, at 25°C and at atmospheric pressure (i.e., 1.013x105 Pa). More preferentially according to this embodiment, the water solubility of the additional agricultural material is advantageously greater than or equal to 20 g/L, preferably greater than or equal to 50 g/L, more preferentially greater than or equal to 100 g/L, at 25°C and at atmospheric pressure (i.e., 1.013x105 Pa). Preferably, the additional agricultural materials are chosen from pesticides, nutrients, biostimulants, plant growth regulators, and mixtures thereof. For example, these pesticides may be chosen from herbicides, other than dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof, 5 fungicides, insecticides, acaricides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides. The person skilled in the art is familiar with such pesticides. Specific examples of pesticides can be found in the book “Sittig’s handbook of Pesticides and Agricultural Chemicals”, 2nd edition, William Andrew Publishing, 2015. 10 Nutrients refer to chemical elements and compounds which are desired or necessary to promote or improve plant growth. Nutrients generally are described as macronutrients or micronutrients. Suitable nutrients for use in the composition according to the invention may be micronutrient compounds, preferably those which are solid at room temperature 15 (20°C) or are partially soluble. Micronutrients typically refer to trace metals or trace elements, and are often applied in lower doses. Suitable micronutrients include trace elements selected from zinc, boron, chlorine, copper, iron, molybdenum, and manganese. The micronutrients may be in a soluble form or included as insoluble solids, 20 and may be in the form of salts or chelates. Preferably, the micronutrient is in the form of a carbonate or oxide. Preferably, the micronutrients may be selected from zinc, calcium, molybdenum or manganese, or magnesium. More preferentially micronutrients for use in the agrochemical formulation according to the invention may be selected from zinc 25 oxide, manganese carbonate, manganese oxide, or calcium carbonate. Macronutrients typically refer to those comprising nitrogen, phosphorus, and potassium, and include fertilisers such as ammonium sulphate, and water conditioning agents. Suitable macronutrients include fertilisers and other nitrogen, phosphorus, or sulphur containing compounds, and water conditioning agents. 30 Suitable fertilisers include inorganic fertilisers that provide nutrients such as nitrogen, phosphorus, potassium or sulphur. Examples of such fertilisers include: for nitrogen as the nutrient: nitrates and or ammonium salts such as ammonium nitrate, including in combination with urea e.g. as urean type materials, calcium ammonium nitrate, ammonium sulphate nitrate, ammonium phosphates, 35 particularly mono-ammonium phosphate, di-ammonium phosphate and ammonium polyphosphate, ammonium sulphate, and the less commonly used calcium nitrate, sodium nitrate, potassium nitrate and ammonium chloride; for phosphorus as the nutrient: acidic forms of phosphorus such as phosphoric, pyrophosphoric or polyphosphoric acids, but more usually salt forms such as 5 ammonium phosphates, particularly mono-ammonium phosphate, di-ammonium phosphate, and ammonium polyphosphate, potassium phosphates, particularly potassium dihydrogen phosphate and potassium polyphosphate; for sulphur as the nutrient: ammonium sulphate and potassium sulphate, e.g. the mixed sulphate with magnesium. 10 The term “biostimulant” is preferably intended to mean a compound which may enhance metabolic or physiological processes such as respiration, photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or a combination thereof. Generally, this is a substance or microorganism that, when applied to seeds, plants or on the rhizosphere, can stimulate natural processes to enhance or benefit 15 nutrient uptake, nutrient use efficiency, tolerance to abiotic stress, or crop quality and yield. Non-limiting examples of biostimulants include seaweed extracts (e.g., ascophyllum nodosum), humic acids (e.g., potassium humate), fulvic acids, myoinositol, glycine, and combinations thereof. 20 Plant growth regulators mean active ingredients used to influence the growth characteristics of plants. Examples of plant growth regulators which may be used in the present invention include, but are not limited to: 1-naphthaleneacetic acid, 1- naphthaleneacetic acid -salt, 1-napthol, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4- DB, 2,4-DEP, 2,3,5-triiodobenzoic acid, 2,4,5-trichlorophenoxyacetic acid, 2-25 naphthoxyacetic acid, 2-naphthoxyacetic acid sodium salt, 3-chloro-4- hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4- chlorophenoxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6- benzylaminopurine, auxindole, a-naphthaleneacetic acid K-salt, ß-naphfhoxyacetic acid, p-chlorophenoxyacetic acid, dicamba, dichlorprop, fenoprop, indole-3 -acetic 30 acid (IAA), indole-3 -acetyl-DL-aspartic acid, indole-3 -acetyl-DL-tryptophan, indole- 3-acetyl-L-alanine, indole-3 -acetyl-L-valine, indole-3 -butyric acid (IBA), indole-3- butyric acid K-salt, indole-3 -propionic acid; a-naphthaleneacetic acid, methyl indole- 3 -acetate, naphthaleneacetamide, naphthaleneacetic acid (NAA), phenylacetic acid, picloram, potassium naphthenate, sodium naphthenate, 4-hydroxyphenethyl alcohol, 35 4-CPPU, 6-benzylaminopurine (BA), 6-(Y,Y-dimethylallylamino)purine (2iP), 2-iP- 2HC1, adenine, adenine hemisulfate, benzyladenine, kinetin, meta-topolin, N6- benzoyladenine, N- benzyl-9-(2-tetrahydropyranyl) adenine (BP A), N-(2-chloro-4- pyridyl)-N-phenylurea, gibberellic acid (GA3), gibberellins, gibberellins A4 + A7 (GA n), ethylene and abscisic acid. 5 It is possible to combine several additional agricultural materials in one composition according to the invention. Preferably, the amount of agricultural material(s) in the composition, 10 including dimethenamid, dimethenamid-P, glufosinate, L-glufosinate and salts thereof, ranges from 0.01 to 90% by weight, more preferentially from 0.1 to 80% by weight; even more preferentially from 0.5 to 70% by weight; better from 1 to 65% by weight, in particular from 5 to 60% by weight, and for instance from 10 to 40% by weight, relative to the total weight of the composition. 15 The composition according to the invention is an emulsion in water concentrate (EW). EW formulation consists of a concentrated oil-in-water emulsion, intended to 20 be diluted with a carrier, usually water when preparing the spray mixture, in the form of a more diluted emulsion for application in the field. The oil-in-water emulsion according to the invention advantageously comprises an aqueous phase as the continuous phase and an oil phase as the discontinuous phase. The oil phase usually forms droplets in the aqueous phase. 25 The average droplet size can be determined by particle size measurement by laser diffraction, e.g. with a Malvern Mastersizer 2000 or 3000. More details can be found in the examples. Preferably, the median droplet size value for volumic particle size distribution dv(50) is usually in the range from 0.1 to 3 μm, more preferentially from 0.2 to 2.5 μm, 30 even more preferentially from 0.4 to 2.0 µm and even better from 0.7 to 1.5 μm. Preferably, the Span index ranges from 0.4 to 15; more preferentially from 0.5 to 10; even more preferentially from 0.8 to 5 and even better from 1 to 3. The composition according to the invention may advantageously comprise at 35 least 5% by weight, preferably at least 10% by weight and more preferably at least 15% by weight of water, based on the total weight of the emulsion. The composition according to the invention may advantageously comprise from 5 to 60% by weight, preferably from 10 to 50% by weight and more preferably from 15 to 40% by weight of water, based on the total weight of the composition. 5 The composition according to the invention may further comprise at least one organic solvent, different from the surfactants (iii), a), b) and c) above; more preferentially at least one non-oxyalkylenated organic solvent. The organic solvents that may be used in the emulsion according to the 10 invention are preferably chosen from: - linear or branched, saturated or unsaturated, aliphatic hydrocarbons, possibly containing a halogen -, phosphorus -, sulfur - and/or nitrogen atom and/or a functional group, - carbocyclic or heterocyclic hydrocarbons, whether saturated, unsaturated or 15 aromatic, possibly containing a halogen -, phosphorus -, sulfur - and/or nitrogen atom and/or a functional group, More preferentially, the solvents are chosen from: - alkanes, cycloalkanes and aromatic derivatives, for example paraffins with a branched chain or straight chain such as "white oil" or decalin; mono-, di- 20 or tri alkyl benzenes or naphthalenes, the compounds sold under the trade name Solvesso® 100, 150, 200 standard and ND grades; - aliphatic, cycloaliphatic or aromatic mono-, di- or tri-esters, for example alkyl alkanoates such as methyl oleate ; benzyl alkanoates; alkyl benzoates; gamma butyrolactone; caprolactone ; esters of glycerol and citric acid ; alkyl 25 salicylates; phthalates; dibenzoates; acetoacetates; glycol ether acetates, dipropylene glycol diacetate; - alkyl mono-, di-, or tri-phosphates such as for example triethyl phosphate; tributyl phosphate; or tri-2-ethylhexylphosphate; - aliphatic, cycloaliphatic or aromatic ketones such as for example dialkyl 30 ketones; benzyl ketones; fenchone; acetophenone; cyclohexanone; alkyl cyclohexanones; - aliphatic, cycloaliphatic or aromatic alcohols such as for example glycerin; glycols; 2-ethylhexanol; cyclohexanol; benzyl alcohols; tetrahydrofurfuryl alcohol; - aliphatic, cycloaliphatic or aromatic ethers such as for example ethers of glycol, notably ethylene and propylene glycol, and their polymers; diphenyl ether, dipropylene glycol ; monomethyl or monobutyl ether, monobutyl ether of tripropylene glycol; alkoxyalkanols; dimethyl isosorbide; 5 - fatty acids such as for example linoleic acid, linolenic acid, oleic acid; - carbonates such as for example propylene or butylene carbonate; lactates; fumarates, succinates, adipates, maleates; - amides such as for example alkyldimethylamides, dimethyl-decanoamide; - alkyl ureas; 10 - amines such as for example alkanolamines, morpholine ; N-alkyl- pyrrolidones; - tetramethyl sulfone; - dimethyl sulfoxide; - halogenoalkanes or halogenated aromatic solvents such as for example 15 chloroalkanes or chlorobenzene. Even more preferentially, the composition further comprises at least one aliphatic, cycloaliphatic or aromatic alcohols, different from the surfactants (iii), a), b) and c) above; even better the composition further comprises at least one aliphatic (C1- 20 C8)alcohol such as glycerin and/or n-octanol. Preferably, the total amount of organic solvent(s), different from the surfactants (iii), a), b) and c) above, is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, 25 relative to the total amount of the composition. Preferably, the total amount of glycerin is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition. 30 Preferably, the total content of organic solvent(s), different from the surfactants (iii), a), b) and c) above, ranges from 0.1% to 20% by weight, more preferentially from 0.1% to 14% by weight, even more preferentially from 1% to 10% by weight, even better from 3% to 8% by weight, relative to the total weight of the composition. Preferably, the total content of glycerin ranges from 0.1% to 20% by weight, more preferentially from 0.1% to 14% by weight, even more preferentially from 1% to 10% by weight, even better from 3% to 8% by weight, relative to the total weight of the composition. 5 According to a preferred embodiment of the invention, the aqueous-phase of the composition further comprises at least one solvent chosen from aliphatic, cycloaliphatic or aromatic alcohols, different from the surfactants (iii), a), b) and c) above; preferably from aliphatic (C1-C8) alcohols such as glycerine or n-octanol. 10 Preferably, the total amount of aqueous-phase solvent(s), different from the surfactants (iii), a), b) and c) above, is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition. 15 According to another preferred embodiment of the invention, the oily phase of the composition further comprises at least one non-water miscible organic solvent, more preferably chosen from aromatic solvents such as paraffins, mono-, di- or tri alkyl benzenes or naphthalenes and aromatic ketones such as acetophenone, amides such as alkyldimethylamides, and mixtures thereof. 20 Preferably, the total amount of oily-phase solvent(s) is from 1 to 150 g/L (gram of solvent(s) per liter of composition), more preferentially from 10 to 100 g/L, better from 40 to 90 g/L, relative to the total amount of the composition. According to the present invention, a “non-water miscible organic solvent” is an organic solvent having a water solubility, at 25°C and at atmospheric pressure (i.e., 25 1.013x105 Pa), advantageously strictly less than 2 g/L (gram of solvent per litre of water), strictly less than 1.5 g/L, more preferentially strictly less than 1 g/L, even more preferentially strictly less than 0.5 g/L, and even better strictly less than 0.1 g/L. 30 Crystallisation inhibitors may also be present in the composition according to the invention. Crystallisation inhibitors may be the solvents mentioned here above. Crystallisation inhibitors may also be non-oxyalkylenated fatty alcohols or fatty acids, for example mention may be made of the product Alkamuls® OL700 marketed by Solvay, alkanolamides, polymers etc. The composition according to the invention may further contain one or more additives different from the ingredients described previously, and which are preferably chosen from viscosity modifying agents, suspending agents, antifoam agents and defoamers, in particular silicone antifoams and defoamers, anti-rebound agents, anti- 5 leaching agents, penetration adjuvants, inert fillers, in particular mineral fillers, binders, diluents, anti-freeze agents, stabilisers, dyes, emetic agents, stickers (adhesion promoters), dispersants, preservatives and/or anti-microbials. Each additive can be present in the composition according to the invention in an amount ranging from 0% to 20% by weight, more preferably from 0% to 10% by 10 weight, relative to the total weight of the composition. Each additive can be for instance present in the composition according to the invention in an amount ranging from 0.1% to 20% by weight, in particular from 0.1% to 10% by weight, relative to the total weight of the composition. Each additive can be present in the composition according to the invention in an amount preferably ranging from 0% to 5% by weight, notably from 15 0.1% to 5% by weight, relative to the total weight of the composition. A person skilled in the art will be able to choose these optional additives and their amounts so that they do not harm the properties of the compositions of the present invention. Preferably, the weight ratio of the total amount of aqueous phase of the 20 composition to the total amount of the oily phase ranges from 1 to 5; more preferentially from 1.1 to 4; even more preferentially from 1.5 to 3.5; even better from 2 to 3. 25 The composition according to the invention may exhibit a non-Newtonian "shear thinning" viscosity, that is, a viscosity that, within a given range of shear stress, decreases with increasing shear stress. The two generally recognized categories of flow behavior are plastic flow behavior and pseudoplastic flow behavior, each include shear thinning flow behavior. 30 In one embodiment, the composition of the invention exhibits plastic flow behavior. As used herein, the term "plastic" in reference to flow behavior of a composition means the composition that exhibits a characteristic "yield stress", that is, a minimum shear stress required to initiate flow of the composition, and exhibits shear thinning behavior over some range of shear stress above the yield stress. A plastic 35 composition exhibits no flow when subjected to shear stress below its yield stress, and flows when subjected to shear stress above its yield stress, wherein, over an intermediate range of shear stress above its yield stress, the composition typically exhibits a non-Newtonian viscosity that decreases with increasing shear stress, that is, shear thinning behavior, and, at shear stresses above the intermediate range of shear stress, the composition may exhibit a viscosity that does not vary with shear stress, that is, Newtonian flow behavior. In another embodiment, the composition of the invention exhibits pseudoplastic flow behavior. As used herein, the term "pseudoplastic" in reference to the flow behavior of a composition means that the composition exhibits a viscosity that decreases with increasing shear stress, that is, shear thinning behavior. In each case, a composition having plastic or pseudoplastic rheological properties resists flow at low shear stress, but that when subjected to an elevated shear stress, such as being shaken in a bottle or squeezed through an orifice, the composition flows and can be easily pumped, poured, or otherwise dispensed from a container. In general, sedimentation or storage condition is a low shear process, having a shear rate in the range of from about 10-6 reciprocal seconds (1/s or, equivalently, s-1) to about 0.01 s-1 and pumping or pouring is a relatively high shear process with a shear rate in the range of greater than or equal to about 1 s-1, more typically from 100s-1 to 1,000 s-1. The viscosity of the composition may be, for example, measured at 20°C using a Brookfield RV Viscosimeter (Ametek) equipped with a spindle 2, 3 or 4 at 20 revolutions per minute ("rpm"), after 1 minute. Preferably, the composition according to the invention in the form of an emulsion in water concentrate (EW) has a viscosity ranging from 300 mPa.s to 4500 mPa.s, more preferentially from 450 to 3500 mPa.s, even more preferentially from 600 to 3000 mPa.s, in particular from 800 to 2500 mPa.s, for instance from 1000 to 2000 mPa.s, measured at 20 rpm using a Brookfield RV viscometer at 20°C and at atmospheric pressure (1.013x105 Pa), enabling a good pourability. The viscosity may also be measured with a standard controlled-stress rheometer, for example a controlled stress rheometer ARG2 (TA Instruments, Surrey, Great Britain), equipped with a geometry of rotor cylinder (diameter: 14mm; cylinder immersed height: 42mm) / stator type having a diameter of 15mm with a gap of 4 mm. Shear rate sweep may be done, between 10-3 s-1 and 200 s-1 at 20°C, 10 points per decade and 1 minute stabilization time may be carried out. The static yield stress value is determined as the value of the applied shear stress beyond which the viscosity starts decreasing. Preferably, the composition of the invention exhibits a viscosity at 10 s-1, using a standard controlled-stress rheometer, of ranging from 300 to 4500 mPa.s, preferably from 450 to 4000 mPa.s, more preferably from 600 to 3500 mPa.s, even more preferably from 800 to 3000 mPa.s, and in particular from 1000 to 2500 mPa.s, advantageously enabling a good pourability. Preferably, the composition of the invention exhibits a viscosity at 100 s-1, using a standard controlled-stress rheometer, ranging from 400 to 2 000 mPa.s, preferably from 450 to 1800 mPa.s, more preferably from 500 to 1600 mPa.s, even more preferably from 550 to 1400 mPa.s, and in particular from 600 to 1200 mPa.s , advantageously enabling a good pourability and/or pumpability at high shear rate. Preferably, the composition of the invention exhibits a yield stress value between 0.5 to 5 Pa, more preferentially from 0.6 to 4 Pa, even more preferentially from 0.7 to 3 Pa, better from 0.8 to 2.5 and even better from 0.9 to 2 Pa. According to a particular embodiment of the invention, once the composition according to the invention diluted to the desired concentration by the final user, the viscosity of the diluted composition is preferably less than 300 mPa.s; more preferentially less than 200 mPa.s; and even better less than 100 mPa.s; measured at 20 rpm using a Brookfield RV viscometer at 20°C and at atmospheric pressure (1.013x105 Pa), advantageously enabling a good viscosity upon dilution. The term “good viscosity upon dilution” is intended to denote compositions that upon dilution in water to the targeted use rate for application exhibits good flowability and good sprayability, that is to say compositions of suitable viscosity upon dilution to the targeted use rate of application, preferably of viscosity less than 300 cP (i.e.300 mPa.s), measured at 20 rpm using a Brookfield RV viscometer at 20°C and at atmospheric pressure (1.013x105 Pa), more preferentially less than 200 cP; and even better less than 100 cP. Advantageously, the composition according to the invention is in the form of an emulsion in water concentrate (EW) that displays a satisfying stability under accelerated storage test conditions, such as after two weeks storage at 54°C, as described in standard CIPAC MT46.3. The composition of the invention especially shows no sign of destabilization such as phase separation, syneresis, flocculation, sedimentation, creaming, presence of macroscopic oil droplets at the surface of the sample. 5 Advantageously, the composition according to the invention is in the form of an emulsion in water concentrate (EW) that displays, upon dilution in water at the targeted use rate, satisfying emulsifiability, emulsion characteristics including emulsion stability, as described in CIPAC MT 36.3. In particular the diluted EW composition at the targeted use rate should not exhibit more than 2ml cream, and 10 should be free of oil or with a trace of oil, after 30 min or 2 hours rest at 30°C or 20°C, for example in water of controlled hardness CIPAC D or CIPAC C, or CIPAC A. In one embodiment, the first herbicide and the second herbicide, also referred to as active ingredient or a.i. or actives, are chemically stable. By chemical stability it is 15 meant that the active ingredients do not degrade substantially when stored for longer time duration and/or at higher temperature conditions (accelerated conditions). “Not degrade substantially” herein refers to degradation of less than 10%, preferably less than 5%, upon 2 weeks storage at 54 °C. 20 In one embodiment, the composition of the present invention is tank mix compatible. Advantageously, the composition is in the form of an oil-in-water emulsion (EW) comprising: 25 - an aqueous phase containing: (i) at least one first herbicide chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof, and (iii) at least one anionic surfactant, - an oily phase containing: 30 (ii) at least one second herbicide chosen from dimethenamid, dimethenamid-P, or mixtures thereof, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates of ethylene oxide and of propylene oxide, and c. at least one phosphate ester surfactant. 5 According to a preferred embodiment of the invention, the composition is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an agronomically acceptable salt thereof, (ii) dimethenamid-P, 10 (iii) at least one anionic surfactant, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates 15 of ethylene oxide and of propylene oxide, and c. at least one phosphate ester surfactant, preferably of formula (VI). According to second preferred embodiment of the invention, the composition 20 is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an agronomically acceptable salt thereof, (ii) dimethenamid-P, (iii) at least one sulfate anionic surfactant, preferably at least one alkyl 25 ether sulfate surfactant, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, preferably from oxyethylenated fatty alcohols, b. at least one non-ionic surfactant chosen from di- or tri-block 30 polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide such as poloxamers, and c. at least one phosphate ester surfactant chosen from the acidic form or the salts of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, 35 di- or tri-styrylphenol. According to another preferred embodiment of the invention, the composition is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an 5 agronomically acceptable salt thereof, (ii) dimethenamid-P, (iii) at least one alkyl ether sulfate surfactant, preferably chosen from alkyl ether sulfate surfactants of formula (IV) as described above, and 10 (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyethylenated fatty alcohols comprising a linear or branched hydrocarbon chain having from 8 to 30, preferably from 10 to 20, even better from 10 to 14 carbon atoms and from 1 to 50, preferentially 15 from 1 to 30, better from 2 to 15, even better from 5 to 10, and still better from 5 to 7 ethylene oxide groups, b. at least one non-ionic surfactant chosen from di- or tri-block polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide such as poloxamers, and 20 c. at least one phosphate ester surfactant chosen from the triethanolamine salt of the mono- and di-esters of phosphoric acid and of oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol. 25 According to one embodiment of the invention, the composition is in the form of an oil-in-water emulsion (EW) and comprises: (i) at least one first herbicide chosen from L-glufosinate or an agronomically acceptable salt thereof, (ii) dimethenamid-P, 30 (iii) at least one alkyl ether sulfate surfactant, preferably chosen from alkyl ether sulfate surfactants of formula (IV) as described above, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyethylenated 35 fatty alcohols comprising a linear or branched hydrocarbon chain having from 8 to 30, preferably from 10 to 20, even better from 10 to 14 carbon atoms and from 1 to 50, preferentially from 1 to 30, better from 2 to 15, even better from 5 to 10, and still better from 5 to 7 ethylene oxide groups, 5 b. at least one non-ionic surfactant chosen from di- or tri-block polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide such as poloxamers, and c. at least one phosphate ester surfactant chosen from the acidic form of the mono- and di-esters of phosphoric acid and of 10 oxyalkylenated (preferentially oxyethylenated) mono-, di- or tri-styrylphenol. The composition according to the invention may be used to kill or inhibit pests and/or clean and/or inhibit growth of undesired plants. 15 The composition according to the invention can be diluted and applied to at least one plant, area adjacent to a plant, soil adapted to support growth of a plant, root of a plant and/or foliage of a plant, in a customary manner; for example, by watering (drenching), drip irrigation, spraying, and/or atomizing. 20 The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical mixture according to the invention is thus obtained. Usually, 20 to 25 2000 litres, preferably 50 to 400 litres, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. The invention also relates to the use of a composition as defined herein for controlling undesirable vegetation in burndown programs, in industrial vegetation 30 management and forestry, in vegetable and perennial crops and in turf and lawn, wherein the inventive composition can be applied pre- or post-emergence, i.e., before, during and/or after emergence of the undesirable plants. Preferred is the application as post-emergence treatment, i.e., during and/or after emergence of the undesirable plants. Herein, the inventive compositions are applied to a locus where crops will be planted 35 before planting or emergence of the crop. Therefore, the present invention also relates to a method for burndown treatment of undesirable vegetation in crops, comprising applying an inventive composition to a locus where crops will be planted before planting (or seeding) or 5 emergence of the crop. Herein, the inventive composition is applied undesirable vegetation or the locus thereof. Thus, present invention therefore relates to a method for controlling undesirable vegetation, which method comprises applying an inventive composition to 10 a locus where undesirable vegetation is present or is expected to be present, wherein application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable vegetation. As used herein, the terms "controlling" and "combating" are synonyms. 15 As used herein, the terms "undesirable vegetation", "undesirable species", "undesirable plants", "harmful plants", "undesirable weeds", or "harmful weeds" are synonyms. The term "locus", as used herein, means the area in which the vegetation or plants are growing or will grow, typically a field. 20 In such burndown programs, the inventive composition can be applied prior to seeding (planting) or after seeding (or planting) of the crop plants but before the emergence of the crop plants, in particular prior to seeding. The inventive compositions are preferably applied prior to seeding of the crop plants. For burndown, the inventive 25 composition will generally be applied a date up to 9 months, frequently up to 6 months, preferably up to 4 months prior to planting the crop. The burndown application can be done at a date up to 1 day prior to emergence of the crop plant and is preferably done at a date prior to seeding/planting of the crop plant, preferably at a date of at least one day, preferably at least 2 days and in particular at least one 4 days prior to planting or 30 from 6 months to 1 day prior emergence, in particular from 4 months to 2 days prior emergence and more preferably from 4 month to 4 days prior emergence. It is, of course, possible to repeat the burndown application once or more, e.g., once, twice, three times, four times or five times within that time frame. It is a particular benefit of the inventive compositions that they have a very good post-emergence herbicide activity, i.e., they show a good herbicidal activity against emerged undesirable plants. Thus, in a preferred embodiment of invention, the inventive compositions are applied post-emergence, i.e., during and/or after, the 5 emergence of the undesirable plants. It is particularly advantageous to apply the inventive compositions post emergent when the undesirable plant starts with leaf development up to flowering. The inventive compositions are particularly useful for controlling undesirable vegetation which has already developed to a state, which is difficult to control with conventional burndown mixtures, i.e., when the individual 10 weed is taller than 10 cm (4 inches) or even taller than 15 cm (6 inches) and/or for heavy weed populations. In the case of a post-emergence treatment of the plants, the inventive compositions are preferably applied by foliar application. 15 If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active 20 compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by). In addition, spray shields may be used. Application may be affected, for example, by usual spraying techniques with water as the carrier, using amounts of spray mixture of usually from 10 to 2000 L/ha, 25 in particular 50 to 1000 L/ha. The required application rate of the composition comprising active compounds depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the composition is 30 used and on the application method. In general, the application rate of the composition is from 55 to 6000 g/ha, preferably from 100 to 5000 g/ha, from 200 to 4000 g/ha, and more preferably from 300 to 3000 g/ha of active ingredient (a.i.). Moreover, the inventive compositions show a persistent herbicidal activity, 35 even under difficult weathering conditions, which allows a more flexible application in burndown applications and minimizes the risk of weeds escaping. Apart from that, the inventive compositions show superior crop compatibility with certain conventional crop plants and with herbicide tolerant crop plants, i.e., their use in these crops leads to a reduced damage of the crop plants and/or does not result in increased damage of 5 the crop plants. Thus, the inventive compositions can also be applied after the emergence of the crop plants. The inventive compositions may also show an accelerated action on harmful plants, i.e. they may affect damage of the harmful plants more quickly if compared to individual components. 10 Both L-glufosinate alone as well as, in the methods of the present invention, the inventive compositions are suitable for controlling a large number of harmful plants in agricultural crops, including monocotyledonous weeds, in particular annual weeds such as gramineous weeds (grasses) including Echinochloa species such as barnyardgrass (Echinochloa crusgalli var. crus-galli), Echinchloa walteri (Pursh) 15 Heller, jungle rice (Echinochloa colona), Echinochloa cruspavonis, Echinochloa oryzicola, Digitaria species such as crabgrass (Digitaria sanguinalis), Digitaria horizontalis, sourgrass (Digitaria insularis) or naked crabgrass (Digitaria nuda), Setaria species such as green foxtail (Setaria viridis), giant foxtail (Setaria faberii), yellow foxtail (Setaria glauca or Setaria pumila) or Setaria verticillata, Sorghum species such 20 as johnsongrass (Sorghum halepense Pers.), Avena species such as wild oats (Avena fatua), Avena sterillis or Avena strigosa, Cenchrus species such as Cenchrus species such as field sandbur (Cenchrus pauciflorus) or Cenchrus echinatus, Bromus species such as Bromus japonicus Thunb, Bromus sterilis or Bromus tectorum, Lolium species, Phalaris species such as Phalaris brachystachys, Phalaris minor or Phalaris persicaria, 25 Eriochloa species, Panicum species such as fall panicum (Panicum dichotomiflorum), Panicum fasciculatum or Panicum maximum, Brachiaria species, annual bluegrass (Poa annua), Alopecurus species such as blackgrass (Alopecurus myosuroides), Alopecurus aequalis Sobol or Alopecurus japonicus Steud, Aegilops species such as Aegilops cylindrica or Aegylops tauschii, Apera spicaventi, Eleusine indica, Cynodon 30 dactylon, couch grass (Agropyron repens or Elymus repens), Agrostis alba, Beckmannia syzigachne (Steud.) Fernald, Chloris species such as Chloris virgata, Commelina species such as Commelina benghalensis, Commelina communis, Commelina diffusa or Commelina erecta, Dactyloctenium aegyptium, Hordeum jubatum, Hordeum leporinum, Imperata cylindrica, Ischaemum rogusum, Ixophorus 35 unisetus, Leerisa hexandra, Leersia japonica, Leptochloa species such as Leptochloa chinensis, Leptochloa fascicularis, Leptochloa filiformis or Leptochloa panicoides, Lolium species such as Lolium multiflorum, Lolium perenne, Lolium persicum or rigid ryegrass (Lolium rigidum), Luziola subintegra, Murdannia nudiflora (L.) Brenan, Oryza latifolia, Oryza rufipogon, Paspalum dis-tichum, Paspalum species, Pennisetum 5 americanum, Pennisetum purpureum, Phleum paniculatum, Phragmites australia, Ploypogon fugax. N., Poa species such as Poa annua or Poa trivialis L., Puccinellia distans, Rottboellia cochinchinensis, Sclerochloa kengiana (Ohwi) Tzvel., Trichloris crinita, Urochloa or Brachiaria species such as Brachiaria decumbens, Brachiaria plantaginea, Brachiaria platyphylla, Urochloa panicoides, Urochloa ramosa and the 10 like. Both L-glufosinate alone as well as the inventive mixtures are also suitable for controlling a large number of dicotyledonous weeds, in particular broad leaf weeds including Polygonum species such as wild buckwheat (Polygonum convolvolus), 15 Polygonum pensilvanicum, Polygonum persicaria or prostrate knotweed (Polygonum aviculare), Amaranthus species such as pigweed (Amaranthus retroflexus), Palmer amaranth (Amaranthus palmeri), tall waterhemp (Amaranthus tuberculatus or Amaranthus rudis), redroot pigweed (Amaranthus retroflexus), green amaranth (Amaranthus hybridus), purple amaranth (Amaranthus lividus), prickly amaranth 20 (Amaranthus spinosus) or Amaranthus quitensis, Chenopodium species such as common lambsquarters (Chenopodium album L.), Chenopodium serotinum or Quinoa (Chenopodium quinoa), Sida species such as prickly sida (Sida spinosa L.), Ambrosia species such as common ragweed (Ambrosia artemisiifolia) or giant ragweed (Ambrosia trifida), Acanthospermum species, Anthemis species such as Anthemis 25 arvensis or Anthemis cotula, Atriplex species, Cirsium species such as Cirsium arvense, Convolvulus species such as field bindweed (Convolvulus arvensis), Conyza species such as horseweed (Conyza canadensis, Erigeron canadensis) or hairy fleabane (Conyza bonariensis, Erigeron bonariensis), Cassia species, Datura species such as jimsonweed (Datura stramonium), Euphorbia species such as toothed spurge 30 (Euphorbia dentata), Euphorbia hirta, Euphorbia helioscopia or fireplant (Euphorbia heterophylla), Geranium species such as Geranium donianum or Geranium pusillum, Galinsoga species, morning glory (Ipomoea species), Lamium species such as henbit dead-nettle (Lamium amplexicaule), Malva species such as dwarf mallow (Malva neglecta) or cheeseweed (Malwa parviflora), Matricaria species such as chamomile 35 (Matricaria chamomilla) or Matricaria inodora, Sysimbrium species, Solanum species such as black nightshade (Solanum nigrum), Xanthium species, Veronica species such as Veronica polita, Viola species, common chickweed (Stellaria media), velvetleaf (Abutilon theophrasti), Sesbania species such as Sesbania exaltata, Sesbania herbacea or hemp sesbania (Sesbania exaltata Cory), Anoda cristata, Bidens species such as 5 Bidens frondosa or Bidens pilosa, Brassica kaber, Capsella species such as Capsella media or Capsella bursa-pastoris, Centaurea cyanus, Galeopsis tetrahit, Galium aparine, Helianthus annuus, Desmodium tortuosum, Kochia scoparia, Mercurialis annua, Myosotis arvensis, Papaver rhoeas, Raphanus species such as wild radish (Raphanus raphanistrum), Salsola species such as Salsola tragus or Salsola kali, 10 Sinapis arvensis, Sonchus species sucha Sonchus asper, Sonchus arvensis or Sonchus oleraceus, Thlaspi arvense, Tagetes minuta, Richardia species such as Richardia scabra or Richardia brasiliensis, Aeschynomeme species such as Aeschynomene denticulata, Aeschynomene indica or Aeschynomene rudis, Alisma species such as Alisma canaliculatum or Alisma plantagoaquatica, Borreria species such as Borreria 15 verticillata, Brassica rapa, Car-duus acanthoides, Parietaria debilis, Portulaca oleracea, Ipomoea species such as Ipomoea grandifolia, Ipomoea hederacea, Ipomoea indivisa, Ipomoea lacunose, Ipomoea lonchophylla or Ipomoea wrightii, Senna obtusifolia, Sida species such as arrowleaf sida (Sida rhombifolia) or prickly sida (Sida spinosa), Spermacoce latifolia, Tridax procumbens, Trianthema portulac-astrum, Parthenium 20 hysterophorus, Portulaca oleracea, Acalypha australis, Ammi majus, Atriplex species, Orobanche species, Mercurialis annua, Cirsium arvense, Calystegia sepium, Stellaria media, Lamium species, Viola species, Celosia argentea, Melampodium divaricatum, Cleome viscosa, Molugo verticilatus, Borhevia erecta, Gomphrena species, Nicandra physalodes, Ricinus communis, Geranium dissectum, Alternanthera species such as 25 Althernanthera philoxe-roides or Alternanthera tenella, Ammannia species such as Ammania coccinea, Anacamtodon fortunei Mitt., Anagallis arvensis, Aneilema keisak, Arenaria serpyllifolia, Argemone mexicana, Asphodelus tenuifolius, Atriplex patula, Bacopa rotundifolia, Brassica napus, Caperonia species sucha as Caperonia castaneifolia or Caperonia palustris, Cephalanoplos segetum, Corynopus didymus, 30 Crepis capillaris, Crepis tectorum, Croton lobatus, Descuminia sophia (L.), Descurainia pinnata, Echinodorus grandiflorus, Eclipta alba, Eclipta prostrata, Eichhornia crassipes, Eleocharis species, Equisetum arvense, Fallopia convolvulus, Fallopia convolvulus, Heteranthera limosa, Jussiaea species, Kallstroemia maxima, Lactuca serriola, Lathyrus aphaca, Launea mudicaulis, Leucas chinensis, Limnocharis 35 flava, Lindernia dubia, Lindernia pyxidaria, Litosper-mum arvense, Ludwigia species such as Ludwigia octovallis, Macroptilium lathyroides, Malachium aquaticum (L.), Melilotus species, Merremia aegyptia, Momordica charantia, Monochoria hastate, Monochoria vaginalis, Mucuna species, Murdannia nudiflora, Oxalis neaei, Phylanthus species, Physalis species, Pistia stratiotes, Potamogeton distinctus, Rorippa 5 islandica, Rotala indica, Rotala ramosior, Rumex dentatus, Rumex obtusifolius, Sagittaria montevidensis, Sagittaria pygmaea Miq., Sagittaria sagittifolia, Sagittaria trifolia L., Senecio vulgaris, Sicyos polyacanthus, Silene gallica, chenopod Sisymbrium species such as Sisymbrium oficinale, Solanum species, Spergula arvensis, Sphenoclea zeylanica, Trianthema spp., Tripleurospermum inodorum, 10 Veronica species such as Veronica persica or Veronica polita Vicia sativa and the like. Both L-glufosinate alone as well as the inventive compositions are also suitable for controlling a large number of annual and perennial sedge weeds including Cyperus species such as purple nutsedge (Cyperus rotundus L.), yellow nutsedge 15 (Cyperus esculentus L.), himekugu (Cyperus brevifolius H.), sedge weed (Cyperus microiria Steud), rice flatsedge (Cyperus iria L.), Cyperus difformis, Cyperus difformis L., Cyperus esculentus, Cyperus ferax, Cyperus flavus, Cyperus iria, Cyperus lanceolatus, Cyperus odoratus, Cyperus rotundus, Cyperus serotinus Rottb., Eleo- charis acicularis, Eleocharis kuroguwai, Fimbristylis dichotoma, Fimbristylis miliacea, 20 Scirpus grossus, Scirpus juncoides, Scirpus juncoides Roxb, Scirpus or Bolboschoenus maritimus, Scirpus or Schoenoplectus mucronatus, Scirpus planiculmis Fr. Schmidt and the like. Both L-glufosinate alone as well as the inventive compositions are also 25 suitable for controlling weeds that are resistant to commonly used herbicides such as, for example, weeds that are resistant to glyphosate, weeds that are resistant to auxin inhibitor herbicides such as e. g. 2,4-D or dicamba, weeds that are resistant to photosynthesis inhibitors such as e. g. atrazine, weeds that are resistant to ALS inhibitors such as e. g. sulfonylureas, imidazolinones or triazolopyrimidines, weeds 30 that are resistant to ACCase inhibitors such as e. g. clodinafop, clethodim or pinoxaden or weeds that are resistant to protoporphyrinogen-IX-oxidase inhibitors such as e. g. sulfentrazone, flumioxazine, fomesafen or acifluorfen, for example the weeds that are listed in the International Sur-vey of Resistant Weeds (http://www.weedscience.org/Summary/SpeciesbySOATable.aspx). In particular, 35 they are suitable for controlling the resistant weeds that are listed in the International Survey of Resistant Weeds, for example ACCase resistant Echinochloa crus-galli, Avena fatua, Alopecurus myosuroides, Echinochloa colona, Alopecurus japonicus, Bromus tectorum, Horde-um murinum, Ischaemum rugosum, Setaria viridis, Sorghum halepense, Alopecurus aequalis, Apera spicaventi, Avena sterilis, Beckmannia 5 szygachne, Bromus diandrus, Digitaria sangui-nalis, Echinocloa oryzoides, Echinochloa phyllopogon, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Brachypodium distachyon, Bromus diandrus, Bromus sterilis, Cynosurus echinatus, Digitaria insularis, Digitaria ischaemum, Leptochloa chinensis, Phalaris brachystachis, Rotboellia cochinchinensis, Digitaria ciliaris, Ehrharta longiflora, 10 Eriochloa punctata, Leptochloa panicoides, Lolium persicum, Polypogon fugax, Sclerochloa kengiana, Snowdenia polystacha, Sorghum sudanese and Brachiaria plantaginea, ALS inhibitor resistant Echinochloa crus-galli, Poa annua, Avena fatua, Alopecurus myosuroides, Echinochloa colona, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Amaranthus retroflexus, Ambrosia 15 artemisifolia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Senecio vernalis, Alopecurus japonicus, Bidens pilosa, Bromus tectorum, Chenopodium album, Conyza bonariensis, Hordeum murinum, Ischaemum rugosum, Senecio vulgaris, Setaria viridis, Sisymbrium orientale, Sorghum halepense, Alopecurus aequalis, Amaranthus blitum, Amaranthus powellii, Apera spica-venti, Avena sterilis, 20 Brassica rapa, Bromus diandrus, Descurainia sophia, Digitaria sanguinalis, Echinochloa oryzoides, Echinochloa phyllopogon, Euphorbia heterophylla, Lactuca serriola, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Sinapis arvensis, Solanum ptycanthum, Sonchus oleraceus, Stellaria media, Amaranthus blitoides, Amaranthus spinosus, Amaranthus viridis, Ambrosia trifida, Bidens 25 subalternans, Bromus diandrus, Bromus sterilis, Capsella bursa-pastoris, Centaurea cyanus, Cynosurus echinatus, Cyperus difformis, Fimbristilis miliacea, Galeopsis tetrahit, Galium aparine, Galium spurium, Helianthus annuus, Hirschfeldia incana, Limnocharis flava, Limnophila erecta, Papaver rhoeas, Parthenium hysterophorus, Phalaris brachystachis, Polygonum convolvulus, Polygonum lapathifolium, 30 Polygonum persicar-ia, Ranunculus acris, Rottboellia cochinchinensis, Sagittaria montevidensis, Salsola tragus, Schoenoplectus mucronatus, Setaria pumila, Sonchus asper, Xanthium strumarium, Ageratum conyzoides, Alisma canaliculatum, Alisma plantagoaquatica, Ammannia auriculata, Ammannia coccinea, Ammannia arvensis, Anthemis cotula, Bacopa rotundifolia, Bifora radians, Blyxa aubertii, Brassica 35 tournefortii, Bromus japonicus, Bromus secalinus, Lithospermum arvense, Camelina microcarpa, Chamaesyce maculata, Chrysanthemum coronarium, Clidemia hirta, Crepis tectorum, Cuscuta pentagona, Cyperus brevifolis, Cyperus compressus, Cyperus esculentus, Cyperus iria, Cyperus odoratus, Damasonium minus, Diplotaxis erucoides, Diplotaxis tenuifolia, Dopatrum junceum, Echium plantagineum, Elatine 5 triandra, Eleocharis acicularis, Erucaria hispanica, Erysimum repandum, Galium tricornutum, Iva xanthifolia, Ixophorus unisetus, Lamium amplexicaule, Limnophilia sessiliflora, Lindernia dubia, Lindernia micrantha, Lindernia procumbens, Ludwigia prostrata, Matricaria recutita, Mesembryanthemum crystallinum, Monochoria korsakowii, Monochoria vaginalis, Myosoton aquaticum, Neslia paniculata, Oryza 10 sativa var. sylvatica, Pentzia suffruticosa, Picris hieracioides, Raphanus sativus, Rapistrum rugosum, Rorippa indica, Rotala indica, Rotala pusilla, Rumex dentatus, Sagittaria guayensis, Sag-ittaria pygmaea, Sagittaria trifolia, Schoenoplectus fluviatilis, Schoenoplectus juncoides, Schoenoplectus wallichii, Sida spinosa, Silene gallica, Sinapis alba, Sisymbrium thellungii, Sorghum bicolor, Spergula arvensis, 15 Thlaspi arvense, Tripleurospermum perforatum, Vaccaria hispanica and Vicia sativa, photosynthesis inhibitor resistant Echinochloa crus-galli, Poa annua, Alopecurus myosuroides, Echinochloa colona, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Amaranthus retroflexus, Ambrosia artemisifolia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Senecio 20 vernalis, Alopecurus japonicus, Bidens pilosa, Bromus tectorum, Chenopodium album, Conyza bonariensis, Ischaemum rugosum, Senecio vulgaris, Setaria viridis, Sisymbrium orientale, Amaranthus blitum, Amaranthus powellii, Apera spicaventi, Beckmannia syzigachne, Brassica rapa, Digitaria sanguinalis, Euphorbia heterophylla, Phalaris minor, Phalaris paradoxa, Setaria faberi, Setaria viridis, Sinapis arvensis, So- 25 lanum ptycanthum, Stellaria media, Amaranthus blitoides, Amaranthus viridis, Bidens subalternans, Brachypodium distachyon, Capsella bursapastoris, Chloris barbata, Cyperus difformis, Echinochloa erecta, Epilobium ciliatum, Polygonum aviculare, Polygonum convolvulus, Polygo-num lapathifolium, Polygonum persicaria, Portulaca oleracea, Schoenoplectus mucronatus, Setaria pumila, Solanum nigrum, Sonchus 30 asper, Urochloa panicoides, Vulpia bromoides, Abutilon theophrasti, Amaranthus albus, Amaranthus cruentus, Arabidopsis thaliana, Arenaria serpyllifolia, Bidens tripartita, Chenopodium album, Chenopodium ficifolium, Chenopodium polyspermum, Crypsis schoenoides, Datura stramonium, Epilobium tetragonum, Galinsoga ciliata, Matricaria discoidea, Panicum capillare, Panicum dichotomiflorum, 35 Plantago lagopus, Polygonum hydopiper, Polygonum pensylvanicum, Polygonum monspeliensis, Rostraria, smyrnacea, Rumex acetosella, Setaria verticillata and Urtica urens, PS-I-electron diversion inhibitor resistant Poa annua, Conyza sumatrensis, Conyza canadensis, Alopecurus japonicus, Bidens pilosa, Conyza bonariensis, Hordeum murinum, Ischaemum rugosum, Amaranthus blitum, Solanum ptycanthum, 5 Arctotheca calendula, Epilobium ciliatum, Hedyotis verticillata, Solanum nigrum, Vulpia bromoides, Convolvulus arvensis, Crassocephalum crepidioides, Cuphea carthagensis, Erigeron philadelphicus, Gamochaeta pensylvanica, Landoltia punctata, Lepidium virginicum, Mazus fauriei, Mazus pumilus, Mitracarpus hirtus, Sclerochloa dura, Solanum americanum and Youngia japonica, glyphosate resistant Poa annua, 10 Echinochloa colona, Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis, Ambrosia artemisifolia, Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Bidens pilosa, Conyza bonariensis, Hordeum murinum, Sorghum halepense, Brassica rapa, Bromus diandrus, Lactuca serriola, Sonchus oleraceus, Amaranthus spinosus, Ambrosia trifida, Digitaria insularis, Hedyotis 15 verticil-lata, Helianthus annuus, Parthenium hysterophorus, Plantago lanceolata, Salsola tragus, Urochloa panicoides, Brachiaria eruciformis, Bromus rubens, Chloris elata, Chloris truncata, Chloris virgata, Cynodon hirsutus, Lactuca saligna, Leptochloa virgata, Paspalum paniculatum and Tridax procumbens, microtubule assembly inhibitor resistant Echinochloa crus-galli, Poa annua, Avena fatua, Alopecurus 20 myosuroides, Amaranthus palmeri, Setaria viridis, Sorghum halepense, Alopecurus aequalis, Beckmannia syzigachne and Fumaria densifloria, auxin herbicide resistant Echinochloa crus-galli, Echinochloa colona, Amaranthus hybridus, Amaranthus rudis, Conyza sumatrensis, Kochia scoparia, Raphanus raphanistrum, Chenopodim album, Sisymbrium orientale, Descurainia sophia, Lactuca serriola, Sinapis arvensis, Sonchus 25 oleraceus, Stellaria media, Arctotheca calendula, Centaurea cyanus, Digitaria ischaemum, Fimbristylis mil-iacea, Galeopsis tetrahit, Galium aparine, Galium spurium, Hirschfeldia incana, Limnocharis flava, Limnocharis erecta, Papaver rhoeas, Plantago lanceolata, Ranunculus acris, Carduus nutans, Carduus pycnocephalus, Centaurea soltitialis, Centaurea stoebe ssp. Micranthos, Cirsium arvense, Commelina 30 diffusa, Echinochloa cruspavonis, Soliva sessilis and Sphenoclea zeylanica, HPPD inhibitor resistant Amaranthus palmeri and Amaranthus rudis, PPO inhibitor resistant Acalypha australis, Amaranthus hybridus, Amaranthus palmeri, Amaranthus retroflexus, Amaranthus rudis, Ambrosia artemisifolia, Avena fatua, Conyza sumatrensis, Descurainia sophia, Euphorbia heterophylla and Senecio vernalis, 35 carotenoid biosynthesis inhibitor resistant Hydrilla verticillata, Raphanus raphanistrum, Senecio vernalis and Sisymbrium orientale, VLCFA inhibitor resistant Alopecurus myosuroides, Avena fatua and Echinochloa crus galli. The inventive compositions are suitable for combating/controlling common 5 harmful plants in fields, where useful plants shall be planted (i.e. in crops) or have been planted (i. e. post-emergence to the crop). The inventive compositions are generally suitable for control of undesired vegetation, both before emergence of the crop (i. e. burndown) or after emergence of the crop (i. e. post-emergence treatment, ‘over-the- top’, ‘OTT’) in fields of the following crops: 10 - Grain crops, including e.g. - cereals (small grain crops) such as wheat (Triticum aestivum) and wheat like crops such as durum (T. durum), einkorn (T. monococcum), emmer (T. dicoccon) and spelt (T. spelta), rye (Secale cereale), triticale (Tritiosecale), barley (Hordeum vulgare); 15 - maize (corn; Zea mays); - sorghum (e.g. Sorghum bicolour); - rice (Oryza spp. such as Oryza sativa and Oryza glaberrima); and - sugar cane; - Legumes (Fabaceae), including e.g. soybeans (Glycine max.), peanuts 20 (Arachis hypogaea and pulse crops such as peas including Pisum sativum, pigeon pea and cowpea, beans including broad beans (Vicia faba), Vigna spp., and Phaseolus spp. and lentils (lens culinaris var.); - brassicaceae, including e.g. canola (Brassica napus), oilseed rape (OSR, Brassica napus), cabbage (B. oleracea var.), mustard such as B. juncea, B. campestris, 25 B. narinosa, B. nigra and B. tournefortii; and turnip (Brassica rapa var.); - other broadleaf crops including e.g. sunflower, cotton, flax, linseed, sugarbeet, potato and tomato; - TNV-crops (TNV: trees, nuts and vine) including e.g. grapes, citrus, pomefruit, e.g. apple and pear, coffee, pistachio and oilpalm, stonefruit, e.g. peach, 30 almond, walnut, olive, cherry, plum and apricot; - turf, pasture and rangeland; - onion and garlic; - bulb ornamentals such as tulips and narcissus; - conifers and deciduous trees such as pinus, fir, oak, maple, dogwood, 35 hawthorne, crabapple, and rhamnus (buckthorn); and - garden ornamentals such as roses, petunia, marigold and snapdragon. The inventive compositions are in particular suitable for burndown of undesired vegetation in fields of the following crop plants: small grain crops such as 5 wheat, barley, rye, triticale and durum, rice, maize (corn), sugarcane, sorghum, soybean, pulse crops such as pea, bean and lentils, peanut, sunflower, sugarbeet, potato, cotton, brassica crops, such as oilseed rape, canola, mustard, cabbage and turnip, turf, pasture, rangeland, grapes, pomefruit, such as apple and pear, stonefruit, such as peach, almond, walnut, pecans, olive, cherry, plum and apricot, citrus, coffee, 10 pistachio, garden ornamentals, such as roses, petunia, marigold, snap dragon, bulb ornamentals such as tulips and narcissus, conifers and deciduous trees such as pinus, fir, oak, maple, dogwood, hawthorne, crabapple and rhamnus. The invention furthermore relates to the use of a compositions as defined 15 herein for controlling undesirable vegetation in crops in a burndown or post-emergence or OTT program, wherein the crop is produced by genetic engineering or by breeding, are resistant to one or more herbicides and/or pathogens such as plant-pathogenous fungi, and/or to attack by insects; preferably resistant to glufosinate. Thus, in as used in the present invention, the term "crops" as used herein 20 includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait. Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create 25 mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create 30 modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant 35 transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, 5 insect resistance, in-creased yield and tolerance to abiotic conditions, like drought. Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, 10 most of the herbicide tolerance traits have been created via the use of transgenes. The use of inventive compositions on crops may result in effects which are specific to a crop com-prising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. 15 Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content. 20 Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany). 25 Preferred are crops, which are tolerant to glufosinate, wherein the glufosinate tolerant crop plant is preferably selected from the group consisting of rice, canola, soybean, corn and cotton plants. The inventive compositions can be applied in conventional manner by using 30 techniques as skilled person is familiar with. Suitable techniques include spraying, atomizing, dusting, spreading or watering. The type of application depends on the intended purpose in a well-known manner; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention. In one embodiment, the inventive compositions are applied to locus mainly by spraying, in particular foliar spraying of an aqueous dilution of the active ingredients of the mixture. Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 5 to 2000 L/ha or 50 to 1000 L/ha (for example from 100 to 500 L/ha). Application of the inventive compositions by the low-volume and the ultra-low-volume method is possible, as is their application in the form of microgranules. The required application rate of the mixture of the pure active compounds 10 depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the mixture is used and on the application method. In general, the rate of application of L-glufosinate is usually from 100 g/ha to 15 1500 g/ha, preferably in the range from 200 g/ha to 1000 g/ha or from 300 g/ha to 1000 g/ha and most preferably in the range of 300 g/ha to 800 g/ha or 300 g/ha to 700 g/ha of active substance (a.i.), and the rate of application of Dimethenamid-P is from 100 g/ha to 2000 g/ha and preferably in the range from 200 g/ha to 1500 g/ha, more preferably from 300 g/ha to 1000 g/ha and most preferably in the range from 400 g/ha 20 to 1000 g/ha of active substance (a.i.). In the above description, all the preferred embodiments with regard to the components may be used individually or in combination. The examples that follow serve to illustrate the invention. 25 Examples 1: Evaluation of the chemical stability of active
Figure imgf000056_0001
30 ^ Viscosity measurement The viscosity (Rotational, shear rate 100 s-1 steady state) of each formulation in Table-A was measured according to the method CIPAC MT 192. 35 ^ Measurement of Particle Size Distribution (PSD) and emulsion test The particle size distribution (PSD) was measured according to the method CIPAC MT 187 using Malvern Mastersizer 3000. 5 The emulsion test is carried out according to the CIPAC MT 36 method, in 100mL glass measuring cylinder. The volume of cream or oil formed after standing 30 minutes, 2 hours and 24 hours (re-emulsification) is then recorded. ^ pH measurement 10 pH (neat) was measured according to the method CIPAC MT 75.3. ^ Measurement of the amount of L-glufosinate ammonium and DMTA-p The amount of L-glufosinate ammonium and DMTA-p was determined according to the following procedure: 15 The method is based on high-pressure liquid chromatography with UV- detection using external calibration for quantification. The determination of the content of L-glufosinate ammonium and DMTA-p in the formulations listed in Table-A was performed by UV-detection using external calibration for quantification. The identity of the analytical substance was confirmed 20 by comparing retention times and UV spectrum recorded for the reference standard against the test item. L-glufosinate ammonium: To 28 mg of L-glufosinate ammonium, 25 mL diluent A (0.05 mol/L 25 potassium phosphate monobasic in water/acetonitrile 90/10 (v/v)) was added. To 240 mg of test sample (formulations in Table A), 25 mL diluent A (0.05 mol/L potassium phosphate monobasic in water/acetonitrile 90/10 (v/v)) is added. DMTA-p: 30 To 30 mg of DMTA-p was added 90 mL acetonitrile and 10 mL water. To 150 mg of test sample (formulations in Table A) was added 90 mL acetonitrile and 10 ml water. In order to determine the content of the active ingredients in the test sample, 35 the mean of the calibration factors is formed from at least two consecutive calibration runs and thus the intervening sample runs are evaluated (bracketing calibration). The content of the active ingredients in the formulation is calculated as follows:
Figure imgf000058_0001
Aactive ingredient = peak area of the active ingredient in the sample solution 5 Wsample = weight quantity of test item in the sample solution F = calibration factor Table-A Ingredients Conc Conc Conc [g/L] [g/L] [g/L] Formulation No. I II III DMTA-p 201.02 201.02 201.02 L-glufosinate ammonium 216.98 216.98 216.98 (at 53% wt.) Glycerine 80 80 80 Genapol LRO 220 220 220 Rhodasurf BC 610 18 18 18 Soprophor FL 25 25 25 Antarox L/64 34 34 34 Antifoam agent 10 10 10 Solvesso 200 ND 60 60 60 Deionized water 135 135 135 Mixed with Mixed with stirrer Mixed with stirrer, (600rpm, stirrer, sheared with Process 2min), 1 pass stirrer sheared Siefer mill 800rpm, with stirrer (3000rpm, 45s+900rpm, (2000rpm, gap 0.5) 60s+900rpm 2min) Visual after White Light grey White preparation emulsion emulsion emulsion Viscosity [mPas] (after 1 day) 815 731 795 PSD D(10) [µm] 0.725 0.613 0.467 PSD D(50) [µm] 1.23 1.22 0.867 PSD D(90) [µm] 2.02 2.37 1.52 pH direct 7.63 7.68 7.81 Tapered cylinder < 0.05 ml < 0.05 ml 2%, after 2h Bs Bs < 0.05 ml Bs L-glufosinate ammonium [g/L] 119.96 117.97 118.59 DMTA-p [g/L] 201.07 195.13 196.18 Density (measured) [g/ml] 1.125 1.115 1.117 Storage 2 weeks at 54°C Fine oïl Fine oïl droplet Fine oïl Visual s in droplets in droplets in (direct after the sample, the sample, n the sample, removing from o no sediment, sediment, no sediment, storage) more beige more beige more beige than white than white than white Reversibility reversible reversible reversible after 2h RT after strong after strong after strong shaking shaking shaking Viscosity [mPas] 805 849 873 PSD D(10) [µm] 0.354 0.484 0.505 PSD D(50) [µm] 0.673 0.842 0.86 PSD D(90) [µm] 1.18 1.39 1.39 pH direct 6.85 6.87 6.73 L-glufosinate 117.45 120.83 120.75 ammonium [g/L] (97.91%) (100%) (100%) DMTA-p [g/L] 197.61 190.78 188.92 (98.28%) (97.77%) (96.30%) Tapered cylinder < 0.05 ml < 0.05 ml 2%, after 2h Bs Bs < 0.05 ml Bs storage 8 weeks at 40°C Fine oïl Fine oïl droplets in droplets in Fine oïl the sample, the sample, droplets in no no the sample, sediment, sediment, no sediment, Visual more beige more beige more beige than white, than white, than white, after after after cooling cooling cooling more white, more white, more white, reversible reversible reversible Viscosity [mPas] 603 766 831 PSD D(10) [µm] 0.743 0.767 0.652 PSD D(50) [µm] 1.32 1.15 1.03 PSD D(90) [µm] 2.3 1.69 1.59 pH direct 6.81 7 6.91 L-glufosinate 121.73 120.72 121.08 ammonium [g/L] (100%) (100%) (100%) DMTA-p [g/L] 191.25 183.36 187.60 (95.11%) (93.97%) (95.63%) Tapered cylinder <0.05 ml <0.05 ml 2%, after 2h Bs Bs <0.05 ml Bs Storage 2 weeks at -5°C/+30°C (repeated cycle: -5°C for 12h then +30°C for 12h - for a period of two weeks) 2% oïl on no sual directly bottom, sed no sediment, Vi iment, no oil, solid after removing solid (take no oil, solid (take out at - out at -5°C) (take out at -5°C) 5°C) Reversibility Reversible Reversible Reversible after 2h RT after strong after strong after strong shaking shaking shaking Viscosity [mPas] 715 902 868 PSD D(10) [µm] 0.813 0.52 0.564 PSD D(50) [µm] 1.49 0.914 0.948 PSD D(90) [µm] 2.48 1.54 1.53 Tapered cylinder < 0.05 ml < 0.05 ml 2%, after 2h Bs Bs < 0.05 ml Bs 5 10
Figure imgf000061_0001
The results above show the good storage stability of the compositions I, II and III according to the invention. 15
Figure imgf000062_0001
Preparation and ingredients of the emulsions: The following emulsions in water concentrate (EW) A1 to A14 (invention) 5 and A15 to A22 (comparative) were prepared according to Method 1, Method 2 or Method 3 described below. Method 1: Organic phase is prepared in a beaker by addition of dimethenamid-P in solvent, followed by addition of surfactant a), b) and/or c), with gentle stirring. 10 In another beaker, the aqueous phase is prepared by addition of antifoam (if any), glycerine or water-soluble solvent, deionized water, glufosinate ammonium (racemic or L-enantiomer) then by anionic surfactant such as sodium lauryl ether sulfate. High shear mixing (IKA Ultraturrax T25 at 7000 rpm during 2 minutes) is done for homogenization of aqueous phase. For emulsion preparation, add one quarter of the 15 aqueous phase in organic phase with high shear mixing (IKA Ultraturrax T25 at 3000 rpm during 30 seconds). Proceed the same way with the second quarter, 3rd one and 4th one. After the total introduction of the aqueous phase in oily phase, a high shear mixing (IKA Ultraturrax T25 at 3000 rpm during 2 minutes) is applied. 20 Method 2: Organic phase is prepared in a standard vessel with counter-blades, equipped with a high shear impeller (for example Rushton impeller or a dissolver blade): addition of dimethenamid-P is done in solvent, followed by addition of surfactant a), b) and/or c), with gentle stirring. In a beaker, the aqueous phase is prepared by addition of an antifoam (if any), glycerine25 or water-soluble solvent, deionized water, glufosinate ammonium (racemic or L- enantiomer) then by anionic surfactant such as sodium lauryl ether sulfate. High shear mixing (IKA Ultraturrax T25 at 7000 rpm during 2 minutes) is done for homogenization of aqueous phase. For emulsion preparation, add one quarter of the aqueous phase in organic phase with high shear mixing (600 rpm) using Rushton 30 impeller or dissolver blade. Proceed the same way with the second quarter, 3rd one and 4th one. After the total introduction of the aqueous phase in oily phase, a high shear mixing is applied until the targeted particles sizes distribution is achieved. Method 3: Organic phase is prepared in a beaker by addition of dimethenamid-P in 35 solvent with gentle stirring. In another beaker, the aqueous phase is prepared by addition of antifoam, glycerine, deionized water, glufosinate ammonium (racemic or L-enantiomer) then by anionic surfactants such as sodium lauryl ether sulfate and sodium 2-ethylhexyl sulfate. High shear mixing (IKA Ultraturrax T25 at 9000 rpm during 2 minutes) is done for 5 homogenization of aqueous phase. For emulsion preparation, add one quarter of the aqueous phase in organic phase with high shear mixing ( using Rushton impeller or dissolver blade at 600 rpm during 30 seconds). Proceed the same way with the 2nd quarter and 3rd one. Then, add the 4th quarter of the aqueous phase in organic phase with high shear mixing (using Rushton impeller or dissolver blade at 900 rpm during 10 2 minutes).
In Tables 1 to 5 are detailed the formulations studied. In the tables below, the amounts of ingredients are in gram of raw material.
Figure imgf000064_0001
Table 1: 5 A1 A2 A3 A4 A5 A6 Compositions (Inv) (Inv) (Inv) (Inv) (Inv) (Inv) Method 1 2 2 1 2 2 Dimethenamid-P 201 201 201 201 219.3 201 (at 98.5%wt) Solvesso 200 ND 60 60 60 60 60 60 Rhodasurf BC 610 25 15 15 - 18 18 Rhodasurf BC 720 - - - 10 - -
Figure imgf000064_0004
Soprophor FL 30 25 25 25 25 25 Antarox L/64 15 25 25 25 30 34 L-Glufosinate- Ammonium 230 230 230 230 250 230 (at 50%wt) Glycerine 85 85 85 85 85 80 Antifoam agent 4 4 4 4 4 - Genapol LRO 220 220 220 220 240 220
Figure imgf000064_0002
Figure imgf000064_0003
n-Octanol - - - - - 10 Deionized water 243 248 248 248 140.7 235 10 Table 2:
Figure imgf000065_0005
A7 A8 A9 A10 Compositions (Inv) (Inv) (Inv) (Inv) Method 1 1 1 1 Dimethenamid-P 183 183 183 183 (at 98.5%wt) Solvesso 200 ND 60 60 60 60 Rhodasurf TR/6 15 15 - 15 Rhodasurf BC 610 - - - - Rhodasurf 860P - - 15 - Soprophor FL 15 25 25 25
Figure imgf000065_0001
Figure imgf000065_0002
Figure imgf000065_0003
Figure imgf000065_0004
Soprophor FLK - - - -
Figure imgf000065_0010
Antarox 25R2 25 - - - Antarox L/64 - 25 25 25 L-Glufosinate- Ammonium 360 360 360 360 (at 50%wt) Glycerine 85 85 85 85 Antifoam agent 4 4 4 4 Genapol LRO 200 200 200 200
Figure imgf000065_0006
Figure imgf000065_0007
Figure imgf000065_0008
Figure imgf000065_0009
Deionized water 198 148 142 148 5 Table 3:
Figure imgf000066_0001
A11 A12 A13 A14 Compositions (Inv) (Inv) (Inv) (Inv) Method 1 1 2 1 Dimethenamid-P 183 183 183 183 (at 98.5%wt) Solvesso 200 ND 60 60 60 60 Rhodasurf TR/6 - - - - Rhodasurf BC 610 15 15 15 15 Rhodasurf 860P - - - - Soprophor FL 25 - 20 20 Soprophor FLK - 35 - -
Figure imgf000066_0002
Antarox 25R2 - - - - Antarox L/64 25 25 15 15 L-Glufosinate- Ammonium 360 360 360 360 (at 50%wt) Glycerine 85 85 85 85 Antifoam agent 4 4 4 4 Genapol LRO 200 200 220 220 Deionized water 148 138 143 143
Table 4: A15 A16 A17 A18 Compositions (Comp) (Comp) (Comp) (Comp) Method 2 2 1 2 Dimethenamid-P 201 201 201 201 (at 98.5%wt) Solvesso 200 ND 60 60 60 60 Rhodasurf 25 - 65 - BC 610
Figure imgf000067_0001
Soprophor FL - 65 - - Antarox L/64 40 - - 65 L-Glufosinate- Ammonium 230 230 230 230 (at 50%wt) Glycerine 80 80 80 80 Genapol LRO 220 220 220 220 Deionized water 257 257 257 257 5
Figure imgf000068_0001
Table 5: Compositions A19 A20 A21 A22 (Comp) (Comp) (Comp) (Comp) Method 1 1 1 3 Dimethenamid-P 183 183 183 201 (at 98.5%wt) Solvesso 200 ND 60 60 60 60 Rhodasurf TR/6 10 15 15 - Soprophor 4D384 10 - - - Mackam OIP 40 - - 15 - Antarox 25R2 15 - - -
Figure imgf000068_0002
Antarox L/64 - 25 25 - L-Glufosinate- Ammonium 360 360 360 230 (at 50%wt) Glycerine 85 85 85 85 Antifoam agent 2 4 4 4 Genapol LRO 200 200 200 124 Rhodapon BOS - - - 410 STD Deionized water 220 173 158 0 5 * Rhodasurf 860P: Ethoxylated isodecyl alcohol 6EO * Soprophor FL: Ethoxylated tristyrylphenol phosphate, neutralized with Triethanolamine 5 10
Figure imgf000069_0001
Evaluation of the emulsion stability 15 ^ Test of storage stability: The stability of each emulsion has been evaluated by allowing a sample of the emulsion to sit undisturbed in a glass vial, typically 100ml, under hot conditions at 2 weeks 54°C, or room temperature (20°C) during 3 months, or -5°C during 1 week. 20 Visual observation has been done to detect any sign of destabilization such as phase separation, syneresis, flocculation, sedimentation, creaming, presence of macroscopic oil droplets at the surface of the sample. A stable formulation is a formulation that do not show any sign of destabilization as described above after the considered period of storage at the considered temperature. 25 ^ Viscosity measurement: The viscosity of each emulsion has been measured according to the two following procedures. 30 (1) The viscosity of each emulsion A1 to A21 was measured at 20°C using a Brookfield RV Viscosimeter (Ametek) equipped with a spindle 2, 3 or 4 at 20 revolutions per minute ("rpm"), after 1 minute. (2) A controlled stress rheometer ARG2 (TA Instruments, Surrey, Great Britain), equipped with a geometry of rotor cylinder (diameter: 14mm; cylinder 35 immersed height: 42mm) / stator type having a diameter of 15mm with a gap of 4 mm was used. Shear rate sweep has been done, between 10-3 sec-1 and 200 sec-1 at 20°C, 10 points per decade and 1 minute stabilization time has been carried out. The static yield stress value is determined as the value of the applied shear stress beyond which the viscosity starts decreasing. 5 ^ Measurement of droplets size distribution: The droplets size distribution has been determined by particle-size measurement by means of laser diffraction. The EW emulsion was diluted in deionised water at 1 wt% and stirred with a 10 magnetic stirrer during 1 minute. The preparation was then transferred to the measurement cell of Malvern Mastersizer 2000 or 3000. The quantity of preparation was adjusted to target an obscuration of 10%, with a tolerance for values of 8 and 15%. The analysis may be carried out with the following parameters: Measurement Parameters: duration of the sample measurement: 10 sec; duration of 15 blank measurement: 10 sec; 3 cycles per measurement. Fraunhofer theory was used for the calculations: optical model: [Fraunhofer]; standard analysis, normal sensibility. dv(50) is the median droplet size value (in microns) for volumic particle size distribution, ie the droplet size value (in microns) that splits the distribution in volume 20 with half above and half below. Similarly 90% of the volumic particles distribution lies below dv(90), and 10% of the volumic particle size distribution lies below dv(10). The Span index, representative of the distribution width is defined as: Span Index = (dv(90) - dv(10))/ dv(50). 25 The results are summarized in Tables 6 to 10 hereafter.
Table 6: Compositions (I A n1 A2 A3 A4 A5 A6 v) (Inv) (Inv) (Inv) (Inv) (Inv) At 20°C, up to 24h after the preparation Appearance e W mh Whitish Whitish Whitish Whitish White ui lt si is oh n emulsion emulsion emulsion emulsion emulsion Particle size dv(50) in µm 0.92 1.10 0.75 1.45 0.95 1.20 Viscosity Brookfield (in mPa.s) 3180 2425 1880 1910 4625 1755 Yield stress (in Pa) 1.59 1.59 1.46 0.55 2.51 0.49 Viscosity rheometer ARG2 at 10 s-1 2296 2296 1651 88 4794 1375 (in mPa.s) Viscosity rheometer ARG2 at 100s-1 998 997 925 681 1997 890 (in mPa.s) CIPAC MT36.3 Emulsion stability, 0 (30min) 0 (30min) 0 (30min) 0/t* (30min) 0/t (30min) 30°C, 0 (2 h) 0 (2 h) 0 (2 h) - t (2 h) t (2 h) Water Cipac D, 2% 0.1 (24 h) 0.1 (24 h) 0.1/0.2 (24 h) 0.2 (24 h) t (24 h) (mL) After 2 weeks storage at 54°C Light brown Light brown Whitish Whitish Light brown Light emulsion – emulsion emulsion emulsion emulsion - no brown Appearance no sign of - no sign of - no sign of - no sign of sign of emulsion - destabili- destabili- destabili- destabili- destabili- no sign of zation zation zation zation zation destabili- zation Particle size dv(50) in µm 1.29 1.12 1.11 1.35 3.18 1.07 Viscosity Brookfield (in mPa.s) 3260 2515 2310 - 3610 4045 CIPAC MT36.3 Emulsion stability, 0 (30min) 0 (30min) 0 (30min) 0 (30min) 0.1 (30min) 30°C, 0 (2 h) 0 (2 h) 0/t (2 h) 0/t (2 h) 0.2 (2 h) - Water Cipac D, 2% t (24 h) t (24 h) 0.1 (24 h) 0.1/0.2 (24 h) 0.3 (24 h) (mL) After 3 months storage at 20°C no sign of no sign of no sign of no sign of no sign of no sign of Appearance destabili- destabili- destabili- destabili- destabili- destabili- zation zation zation zation zation zation * in the table above, t means traces (i.e. <0.1mL). Table 7: Compositions A8 A9 A10 A1 (I A7 1 nv) (Inv) (Inv) (Inv) (Inv) At 20°C, up to 24h after the preparation Appearance Whitish Whitish Whitish Whitish White emulsion emulsion emulsion emulsion emulsion Particle size dv(50) in µm 1.45 1.37 1.68 1.57 1.83 Viscosity Brookfield 3270 1345 1110 1095 1040 (in mPa.s) CIPAC MT36.3 Emulsion stability, 0 (3 *0min) 0 (3 *0min) 0 (30min) 0/t (30min) 0 (30min) 30°C, 0/t (2 h) 0/t (2 h) <0.1 (2 h) 0.1 (2 h) t (2 h) Water Cipac D, 2% 0.1/0.2 (24 h) 0.1 (24 h) 0 (24 h) 0 (24 h) 0.1 (24 h) (mL) After 2 weeks storage at 54°C Light brown Light brown Light brown Light brown emulsion – no emulsion – no emulsion – no emulsion – no Appearance - sign of sign of sign of sign of destabili- destabili- destabili- destabili- zation zation zation zation Particle size dv(50) in µm - 1.54 1.53 1.28 1.68 Viscosity Brookfield - - 1460 1800 1770 (in mPa.s) CIPAC MT36.3 Emulsion stability, 0 (30min) 0 (30min) 0 (30min) 0/t (30min) 30°C, - 0/t (2 h) 0 (2 h) 0/t (2 h) t (2 h) Water Cipac D, 2% 0.1 (24 h) < 0.1 (24 h) < 0.1 (24 h) 0.2 (24 h) (mL) After 3 months storage at 20°C no sign of no sign of no sign of no sign of no sign of Appearance destabili- destabili- destabili- destabili- destabili- zation zation zation zation zation * in the table above, t means traces (i.e. <0.1mL). Table 8: Compositions ( A In 1 v2 A13 A14 ) (Inv) (Inv) At 20°C, up to 24h after the preparation Appearance White emulsion Whitish emulsion Whitish emulsion Particle size dv(50) in µm 2.40 0.98 0.90 Viscosity Brookfield (in mPa.s) 2985 2320 2205 Yield stress (in Pa) - 0.86 0.96 Viscosity rheometer ARG2 at 10 s-1 (in - 1284 1275 mPa.s) Viscosity rheometer ARG2 at 100 s-1 (in mPa.s) - 699 694 CIPAC MT36.3 0 (3 *0min) 0 (30min) 0 (30min) Emulsion stability, 30°C, 0/t (2 h) 0/t (2 h) 0/t (2 h) Water Cipac D, 2% (mL) 0.1 (24 h) 0.1 (24 h) 0.1 (24 h) After 2 weeks storage at 54°C Light brown emulsion Light brown Light brown Appearance – no sign of emulsion – no sign emulsion – no sign destabilization of destabilization of destabilization Particle size dv(50) in µm 1.37 1.51 1.39 Viscosity Brookfield (in mPa.s) 2800 1800 1800 CIPAC MT36.3 0 (30min) 0 (30min) 0 (30min) Emulsion stability, 30°C, 0/t (2 h) 0/t (2 h) t (2 h) Water Cipac D, 2% (mL) 0.1 (24 h) 0.1 (24 h) 0.1/0.2 (24 h) After 8 weeks storage at 40°C Light brown Light brown Appearance - emulsion – no sign emulsion – no sign of destabilization of destabilization Particle size dv(50) in µm - 1.55 1.83 Viscosity Brookfield (in mPa.s) - 2420 2480 CIPAC MT36.3 0 (30min) 0 (30min) Emulsion stability, 30°C, - 0/t (2 h) 0 (2 h) Water Cipac D, 2% (mL) 0.1 (24 h) 0.1 (24 h) After 3 months storage at 20°C Appearance no sign z o at f io d nestabili- no sign of destabili- no sign of zation destabilization * in the table above, t means traces (i.e. <0.1mL). Table 9: Compositions (C A o1 m5 A16 A17 A18 p) (Comp) (Comp) (Comp) At 20°C, up to 24h after the preparation Appearance em W uh ls it ie White White White on emulsion emulsion emulsion Particle size dv(50) in µm 2.05 1.44 3.32 - Viscosity Brookfield 1510 2935 8140 1 215 (in mPa.s) Yield stress (in Pa) 1.55 1.11 10.1 0.61 Viscosity rheometer ARG2 at 10 s-1 1110 3160 2710 529 (in mPa.s) Viscosity rheometer ARG2 at 100s-1 314 1180 619 142 (in mPa.s) CIPAC MT36.3 Emulsion stability, 30°C, 0 (30min) 0 (30min) 0 (30min) Water Cipac D, t* (2 h) 0 (2 h) t * (2 h) - 2% (mL) After 2 weeks storage at 20°C Non- homogeneous Appearance bottom phase em bottom phase bottom phase separation ulsion - macroscopic separation separation oil droplets After 2 weeks storage at 54°C Non- Non- Non- homogeneou Non- homogeneous homogeneous s ulsion - emulsion - emulsi homogeneous Appearance em on ic (3 emulsion - macroscopic macroscop phases)- macroscopic oil droplets oil droplets macroscopic oil droplets oil droplets * in the table above, t means traces (i.e. <0.1mL). Table 10: Compositions (C A o1 m9 A20 A21 A22 p) (Comp) (Comp) (Comp) At 20°C, up to 24h after the preparation Phase Weissenberg High effect / High viscosit Phase Appearance separation into y / viscosity / Whit separation into 2 layers e White emulsion emulsion 2 layers 19. * Particle size dv(50) * 40 Measurement in µm - 1.97 1.75 carried out a few minutes after the preparation of the emulsion Viscosity Brookfield - 4650 4785 - CIPAC MT36.3 Emulsion stability, 0/t* (30min) 0 (30min) 30°C, - t (2 h) 0/t (2 h) - Water Cipac D, 2% 0.1 (24 h) 0.1 (24 h) (mL) * in the table above, t means traces (i.e. <0.1mL). The above tests show that the compositions according to the invention comprising the specific combination of the surfactants a), b) and c) as claimed, have a good viscosity profile and pourability, as well as a better stability upon storage at room temperature (20°C), or even at 2 weeks at 54°C, than the comparative compositions A15 to A22 which do not comprise the specific combination of the surfactants a), b) and c) as claimed.
Example 3: Products: Liberty®: 280 g/l racemic glufosinate-ammonium 5 Liberty® Ultra (BAS 101005 H): 211 g/l L-glufosinate ammonium Outlook®: 720 g/l DMTA-p Roundup PowerMAX® II: 540 g/l Glyphosate As indicated in the respective examples below, assessment was either after 9 to 17 days 10 after treatment (DAT) or 45 to 50 days after treatment (DAT). Table 11: Post emergence control (9 - 17 DAT) in Soybean and Cotton Compound/formulation Application rate in g Herbicidal activity against ai/ha Pigweed Broadleaf Grass Liberty ® 655 93 93 85 Liberty® + Outlook® 655 + 630 92 96 90 Liberty® Ultra 370 95 94 82 Liberty® Ultra + Outlook® 370 + 630 96 97 92 Formulation No. A5 1000 95 98 93 Formulation No. A2 1000 95 96 92 Formulation No. A13 1310 95 97 93 Roundup PowerMAX® II 1260 74 98 97 Roundup PowerMAX® II + Outlook® 1260 + 630 70 99 99 15 Table 12: Post emergence control (45 - 50 DAT) in Soybean and Cotton Application Compound/formulation rate in g Herbicidal activity against ai/ha Pigweed Broadleaf Grass Liberty® 655 71 91 54 Liberty® + Outlook® 655 + 630 75 98 71 Liberty® Ultra 370 79 96 49 Liberty® Ultra + Outlook® 370 + 630 81 97 82 Formulation No. A5 1000 81 97 81 Formulation No. A2 1000 81 97 79 Formulation No. A13 1310 79 99 76 Roundup PowerMAX® II 1260 61 93 79 Roundup PowerMAX® II + Outlook® 1260 + 630 63 98 97 The compositions according to the invention comprising the specific combination of the 5 surfactants a), b) and c) as claimed, are not only storage stable, as is evident from data in Tables 6-8 but also retain a good control of wide variety of weeds as seen from the data in Tables 11 and 12.

Claims

CLAIMS 5 1. A composition in the form of an oil-in-water emulsion (EW) comprising: (i) at least one first herbicide chosen from glufosinate, L-glufosinate, or an agronomically acceptable salt thereof, (ii) at least one second herbicide chosen from dimethenamid, dimethenamid-P, or mixtures thereof, 10 (iii) at least one anionic surfactant, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from polycondensates 15 of ethylene oxide and of propylene oxide, and c. at least one phosphate ester surfactant. 2. Composition according to claim 1, wherein the first herbicide(s) (i) are chosen from L-glufosinate or an agronomically acceptable salt thereof. 20 3. Composition according to any one of the preceding claims, wherein the total amount of first herbicide(s) (i) is from 10 to 600 g/L, preferably from 50 to 500 g/L, more preferentially from 100 to 450 g/L, even better from 100 to 400 g/L, still better from 100 to 200 g/L, relative to the total amount of the composition. 25 4. Composition according to any one of the preceding claims, wherein the second herbicide (ii) is dimethenamid-P. 5. Composition according to any one of the preceding claims, wherein the 30 total amount of second herbicide(s) (ii) is from 10 to 600 g/L, preferably from 50 to 500 g/L, more preferentially from 100 to 450 g/L, even more preferentially from 100 to 400 g/L, still better from 100 to 300 g/L, relative to the total amount of the composition. 6. Composition according to any one of the preceding claims, wherein the weight ratio of the total amount of first herbicide(s) (i) to the total amount of second herbicide(s) (ii) ranges from 0.1 to 5; preferably from 0.125 to 4; more preferentially from 0.2 to 3; even more preferentially 0.3 to 2; better from 0.4 to 1.5, and even better from 0.5 to 1. 7. Composition according to any one of the preceding claims, the anionic surfactant(s) (iii) are chosen from sulfate anionic surfactants; preferably from alkyl ether sulfates; more preferentially from those of formula (IV): [R-O-(A-O)n-SO3]- M+ (IV) in which M+ is a cation; A is C2-C3 alkandiyl; R is selected from linear or branched C10-C20 alkyl, preferably C12-C14 alkyl, and mixtures thereof; and n is a natural positive number of 1 to 12 where the number average of n is in the range of 1 to 10. 8. Composition according to any one of the preceding claims, wherein the non-ionic surfactants a) are chosen from oxyethylenated fatty alcohols; preferably comprising a linear or branched hydrocarbon chain having from 8 to 30, in particular from 10 to 20, better from 10 to 14, carbon atoms, and from 1 to 50, in particular from 2 to 15, even better from 5 to 10 alkylene oxide groups, preferentially ethylene oxide groups. 9. Composition according to any one of the preceding claims, wherein the non-ionic surfactants b) are chosen from di- or tri-block polymers wherein the polymeric moiety being composed of ethylene oxide and propylene oxide; more preferentially the non-ionic surfactants b) are chosen from poloxamers. 10. Composition according to any one of the preceding claims, wherein the phosphate ester surfactant(s) c) are chosen from: - the mono- and di-esters of phosphoric acid and of oxyalkylenated mono-, di- or tri-styrylphenol; - the mono- and di-esters of phosphoric acid and of oxyalkylenated C8- C30 aliphatic alcohol; - salts thereof; and - mixtures thereof. 11. Composition according to any one of the preceding claims, wherein: 5 - the anionic surfactant(s) (iii) is in the aqueous phase, and/or - the surfactant mixture (M) is in the oily phase. 12. Composition according to any one of the preceding claims, comprising: - an aqueous phase containing: 10 (i) at least one first herbicide chosen from glufosinate, L- glufosinate, or an agronomically acceptable salt thereof, and (iii) at least one anionic surfactant, and - an oily phase containing: (ii) at least one second herbicide chosen from dimethenamid, 15 dimethenamid-P, or mixtures thereof, and (iv) a surfactant mixture (M) comprising: a. at least one non-ionic surfactant chosen from oxyalkylenated fatty alcohols, b. at least one non-ionic surfactant chosen from 20 polycondensates of ethylene oxide and of propylene oxide, and c. at least one phosphate ester surfactant. 13. Composition according to any one of the preceding claims, further 25 comprising at least one organic solvent; preferably at least one non-oxyalkylenated organic solvent. 14. Method for controlling undesired plants or for influencing the growth of plants comprising the application of the composition as defined in any one of claims 1 30 to 13 onto soils and/or plants.
PCT/EP2024/076014 2023-09-21 2024-09-18 Emulsion in water concentrate comprising glufosinate, vlcfa inhibitor and specific surfactants Pending WO2025061719A1 (en)

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