EA045461B1 - COMPOSITIONS OF MICROPARTICLES CONTAINING SAFLUFENACIL - Google Patents

Description

The present invention relates to microparticle compositions containing saflufenacil, a method for their preparation and the use of these microparticle compositions for the control of unwanted vegetation.

Saflufenacil is the international nonproprietary name of the herbicidally active phenyluracil compound 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)pyrimidinyl]-4-fluoro- N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide.

Saflufenacil was first described in WO 01/083459.

Saflufenacil is a highly active herbicide that effectively suppresses the growth of unwanted vegetation at low application rates. Unfortunately, its selectivity is not always satisfactory and its use among crops is somewhat limited. Moreover, saflufenacil does not have sufficient residual activity and therefore regrowth may occur soon after its use.

Herbicides such as saflufenacil are typically applied as dilute aqueous spray solutions, which are prepared by diluting a concentrated herbicide formulation with water. For this purpose, pesticide compounds can be formulated in solid forms such as wettable powders (WP) and water-dispersible granules (WG), as well as in liquid forms such as emulsions, emulsion concentrates (EC), suspoemulsions (SE) or suspension concentrates (SC). For effective encapsulation, it is particularly important that the formulations can be easily diluted with water and that the solution remains stable over time without releasing the active substance, as this may cause clogging of the spray nozzles. From an environmental point of view, it is preferable that the formulation does not contain large amounts of organic solvents, which generally favors solid formulations and aqueous SC formulations.

Despite the above-mentioned advantages associated with the use of SC, there are a number of problems known to one skilled in the art that are sometimes encountered with SC as a result of sedimentation during long-term storage or storage at elevated temperatures related to the resistance of the deposited particles to reuse. formation of a suspension and with the formation of crystalline material during storage. As a result, the formulations may be difficult to handle and their biological effectiveness may be inconsistent.

When trying to formulate saflufenacil, several problems arise. Saflufenacil carries an N-amino-sulfonylcarboxamide side chain, which can undergo hydrolysis at basic pH values. In addition, saflufenacil can exist in various crystalline and non-crystalline forms, namely, in amorphous forms, in the form of crystalline hydrates and crystalline anhydrate, which can undergo uncontrolled transformation into another crystalline form. This transformation, in turn, can lead to the enlargement of saflufenacil particles, in particular when formulated as a suspension concentrate. These factors can lead to a decrease in the chemical and physical stability of the formulations, an effect that is particularly pronounced when the formulations are stored for extended periods of time and/or at elevated temperatures. These factors may also result in poor dilution properties, as large saflufenacil particles tend to be released from the diluted formulation.

To date, several stable aqueous agricultural formulations of saflufenacil have been described. WO 2011/023759 describes an aqueous suspension concentrate formulation containing saflufenacil anhydrate and a combination of certain anionic and nonionic surfactants. WO 2011/023758 describes the formulation of an aqueous suspension concentrate of saflufenacil, which further contains glyphosate as an additional herbicide.

Despite the fact that these formulations are stable, they do not solve the problems of low selectivity for crops and insufficient residual activity.

It is generally known to provide pesticidal active compounds in the form of microencapsulated formulations (see H. Mollet, A. Grubenmann Formulation Technology 1st ed., WileyVCH Verlag GmbH, Weinheim 2001, Chapter 6.4 and Chapter 14.2.2).

Microencapsulation can mainly be achieved through coacervation, spray drying, fluid bed coating, electrostatic microencapsulation or in situ polymerization techniques.

These methods provide particles of the active compound where the active compound is surrounded by a polymeric wall material.

WO 2017/037210 discloses saflufenacil microparticle compositions.

Although microencapsulation can improve the acute toxicity of a pesticide or reduce degradation, this is often difficult to achieve. In particular, the aggregation of pesticide particles during or after encapsulation is a major problem when one encapsulation method,

- 1 045461 which may work for a particular pesticide compound will not necessarily work for another pesticide compound. When attempting to encapsulate a solid material in an aqueous suspension of the solid material using an in situ polymerization method, the solid material tends to agglomerate, resulting in large particles of active ingredient particles that are enclosed in a polymer matrix. The suspension thus obtained is usually no longer suitable for agricultural use. Thus, it was not possible to effectively encapsulate pesticide solids by using small amounts of encapsulating polymer.

One of the challenges with respect to known formulations of saflufenacil is to increase miscibility with other pesticides.

Brief description of the invention

It is an object of the present invention to provide a formulation of saflufenacil that can be mixed with a wide range of other pesticides, in particular with other tank mix partners that are typically combined with saflufenacil, such as glyphosate, glufosinate, dicamba, etc. Moreover, it must demonstrate both high physical stability and high chemical stability over long periods of storage, while maintaining its biological effectiveness. Moreover, it must also be miscible with tank mix partners, which are usually combined with saflufenacil. When diluted with water, the formulation should yield a stable aqueous composition of saflufenacil without the formation of coarse material or supernatant.

Surprisingly, it has been discovered that this object can be achieved using solid saflufenacil microparticle compositions in which the solid saflufenacil is surrounded or embedded in an aminoplast polymer and which further contain at least one lignin-based sulfonic acid A, such as lignosulfonic acid, ethoxylated lignosulfonic acid or oxidized lignins, wherein said lignosulfonic acid A has an average molar mass MW of at least 10,000 Da.

In the microparticle compositions of the present invention, saflufenacil is less prone to degradation. Thus, the microparticle compositions of the present invention provide both high physical stability and high chemical stability over long shelf life while maintaining the biological effectiveness of saflufenacil. Moreover, microparticle compositions in accordance with the present invention can be easily formulated. Moreover, the microparticle compositions of the present invention in the form of aqueous suspensions provide improved miscibility of tank mix components, and therefore tank mix with other pesticide formulations can be easily prepared without them interacting with other formulations to adversely affect them. stability when diluted.

It has also surprisingly been discovered that solid saflufenacil can be effectively microencapsulated by using aminoplast precondensates and following the method described below. Therefore, the second aspect of the present invention relates to a method for producing microparticle compositions, which is described in this application, wherein said method includes the following steps:

I) providing an aqueous suspension of saflufenacil solid particles;

II) adding an aminoplast precondensate to the aqueous suspension of saflufenacil particles;

III) carrying out the polycondensation of the aminoplast precondensate, for example, by heating the aqueous suspension of stage II) at a pH value at which the polycondensation of the aminoplast precondensate will occur at the reaction temperature.

This method results in a stable aqueous suspension wherein saflufenacil is present in the form of microparticles that contain solid saflufenacil which is surrounded or embedded in an aminoplast polymer. Based on this, if necessary, microparticles can be isolated. Surprisingly, this method does not result in significant agglomeration of saflufenacil particles, as has been observed with other in situ polymerization methods.

Detailed Description of the Invention

In the microparticle composition according to the invention, saflufenacil is present in the form of microparticles that contain solid saflufenacil as a core material, said composition further containing at least one lignin-based sulfonic acid A, such as lignosulfonic acid, ethoxylated lignosulfonic acid or oxidized lignins, wherein said lignosulfonic acid A has an average molar mass MW of at least 10,000 Da. In microparticles, solid saflufenacil forms a core material that is surrounded by or embedded in at least one aminoplast polymer. In this context, it should be understood that aminoplast polymers can form a regular or irregularly shaped shell that surrounds or encloses the core material. Microparticles may have one solid core formed by saflufenacil and a shell or matrix formed by an aminoplast polymer. Of course, the microparticles can also have a domain structure that includes a certain number of saflufenacil solid particles, for example 3-1000 or

10-500, amorphous or crystalline saflufenacil, which is enclosed in an aminoplast polymer.

It is not necessary for the aminoplast polymer to form a completely closed shell.

However, often the shell will completely surround the core material, like a protective layer, resulting in a barrier between the core material and the surrounding material.

Aminoplast polymers, also called amino resins, amino condensation resins or amidosins, are the polycondensation products of one or more aldehydes, such as formaldehyde, acetaldehyde, propanal, glyoxal or glutaraldehyde, with one or more amino compounds, which usually have at least two primary amino groups such as urea, thiourea, melamine, which can be fully or partially esterified, cyanoguanamine (= dicyandiamide) and benzoguanamine. Examples of aminoplast polymers are melamine-formaldehyde polycondensates (melamine-formaldehyde resins or MF resins), including resins derived from fully or partially esterified melamine-formaldehyde condensates, urea-formaldehyde resins (UF resins), thiourea-formaldehyde resins (TUF resins), polycondensates melamine, urea and formaldehyde (MUF resins), including resins obtained from fully or partially esterified melamine, urea and formaldehyde condensates, polycondensates of melamine, thiourea and formaldehyde (MTUF resins), including resins obtained from fully or partially esterified melamine, thiourea condensates and formaldehyde, urea-glutaraldehyde resins, benzoguanamine-formaldehyde polycondensates, dicyandiamide-formaldehyde polycondensates and urea-glyoxal polycondensates. Suitable aminoplast polymers for microencapsulation are known and can be found, inter alia, in Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd edition, vol. 2, pp. 440-469, in the prior art cited in the introduction US 4918317, EP 26914, EP 218887, EP 319337, EP 383337, EP 415273, DE 19833347, DE 19835114 and WO 01/51197. In UF and TUF resins, the molar ratios of urea or thiourea to formaldehyde are generally in the range from 1:0.8 to 1:4, in particular from 1:1.5 to 1:4, in particular from 1:2 up to 1:3.5. If glutaraldehyde is used instead of formaldehyde, the molar ratios of urea or thiourea to glutaraldehyde can in particular be in the range from 1:1.2 to 1:3, in particular in the range from 1:1.5 to 1: 2.5.

In MF and MUF resins, the molar ratios of melamine to formaldehyde are generally in the range from 1:1.5 to 1:10, in particular from 1:3 to 1:8, preferably from 1:4 to 1:6.

In MUF and MTUF resins, the molar ratios of melamine + urea or thiourea to formaldehyde are generally in the range of 1:0.8 to 1:9, in particular 1:2 to 1:8; preferably from 1:3 to 1:6. The molar ratio of urea or thiourea to melamine can be in the range from 50:1 to 1:100 and in particular from 30:1 to 1:30.

During the preparation of the above-mentioned aminoplast resins, the precondensates can be used in the form of esterified precondensates of an amino compound and an aldehyde. In these esterified precondensates, the methylol groups are formed by the reaction of the amino groups of formaldehyde with an alkanol or alkanediol, in particular with a C1- _C4 alkanol, such as methanol, ethanol, npropanol or n-butanol, in particular with methanol, or _C2 -C ₄ -alkanediol such as ethylene glycol. The degree of esterification of these resins can be controlled by the molar ratio of amino groups to alkanol, which is typically in the range of 10:1 to 1:10, preferably in the range of 2:1 to 1:5.

The aminoplast polymer material that surrounds or encloses the solid saflufenacil is most preferably selected from the group consisting of melamine-formaldehyde resins, including melamine-formaldehyde resins derived from fully or partially esterified melamine-formaldehyde condensates, as well as urea-formaldehyde resins and mixtures of them. In particular, the aminoplast polymer material that surrounds or encloses the solid saflufenacil is a melamine-formaldehyde resin, in particular a melamine-formaldehyde resin that is derived from fully or partially esterified melamine-formaldehyde condensates, which may contain a small amount of urea, for example 1- 20 mol.%, based on melamine.

In microparticle compositions according to the invention, the amount of aminoplast polymer material that surrounds or encloses the solid saflufenacil will generally not exceed the amount of saflufenacil contained in the composition, and is preferably no more than 40% by weight, in particular no more than than 35 wt.% and, in particular, not more than 30 wt.% or not more than 25 wt.%, based on the total amount of saflufenacil and aminoplast polymers. The amount of aminoplast polymer material which surrounds or encloses the solid saflufenacil is preferably from 0.5 to 40% by weight, in particular from 1 to 35% by weight and in particular from 5 to 25% by weight based on the total mass of capsules, that is, based on the total amount of saflufenacil and aminoplast polymers. The polymeric material of the microparticle composition according to the invention, which surrounds or encloses the solid saflufenacil, may contain additional water-insoluble polymers. However, the amount of such polymers will generally not exceed 20% of the total amount of encapsulating polymeric material, and preferably will not exceed 10% by weight of the total amount of polymeric material that surrounds or encloses the saflufenacil solid.

The solid saflufenacil that is surrounded by or embedded in at least one aminoplast polymer may be any known form of solid saflufenacil, including amorphous saflufenacil and, in particular, crystalline saflufenacil, for example, crystalline saflufenacil anhydrate, which is described in WO 08/043835. or crystalline saflufenacil hydrate, which is described in WO 08/043836.

In addition to solid saflufenacil, the microparticle core material may contain an oil, for example a hydrocarbon solvent such as an aromatic, paraffinic or isoparaffin hydrocarbon, preferably having a boiling point above 100°C, a vegetable oil such as corn oil, rapeseed oil, or an ester a fatty acid such as a C1-C ₁₀ alkyl ester of a C ₁₀ -C ₂₂ fatty acid, in particular methyl or ethyl esters of vegetable oils, such as rapeseed oil methyl ester or corn oil methyl ester. In a certain embodiment, the core material does not contain oil as defined herein, or the oil content is less than 10 wt.% based on the weight of the core material. In particular, the kernel does not contain oil.

In addition to solid saflufenacil, the microparticle core material may further contain an additional pesticidal compound, in particular a herbicidal compound or antidote, preferably having a reduced solubility in water, which generally does not exceed 10 g/l, in particular 5 g/l or even 1 g/l at 25°C (deionized water). In particular, solid saflufenacil constitutes at least 80%, in particular at least 90% of the pesticides contained in the microparticles.

Microparticles in accordance with the present invention are discrete particles that typically have a particle size of less than 50 microns. Preferably, the particle size of the microparticles, that is, their diameter, will generally not exceed 40 μm, preferably will not exceed 35 μm, and in particular will not exceed 30 μm. The particle size presented is the so-called d90 value, which should be understood as a value that does not exceed the diameters of at least 90% by weight of the microparticles. The microparticles have an average particle diameter, which in this application is also referred to as a d50 value, ranging from 1 to 25 μm, in particular from 1.5 to 20 μm, in particular from 2 to 10 μm. The d50 value is defined as the value that is above the diameters of 50 wt.% particles and below the diameters of 50 wt.% particles. The d90 value as well as the d50 value can be calculated based on the particle size distribution of the microparticles. Typically, the particle d10 value, that is, the value of the diameters that exceed at least 10 wt.% of the microparticles, will be at least 0.5 μm and, for example, may be in the range from 0.5 μm to 10 μm, in in particular from 1 to 5 microns. The particle size distribution (i.e., diameters) of the microparticles can be determined using conventional methods such as dynamic or static light scattering of an aqueous dispersion of the microparticle composition, for example, at a temperature of 25° C. and a concentration ranging from 0.1 to 1 wt. %.

The microparticle compositions according to the invention contain at least one anionic polymer surfactant A1, which is hereinafter also referred to as anionic polymer surfactant A1 or polymer surfactant A1, wherein said at least one anionic polymer surfactant substance A1 is a lignin-based sulfonic acid A, wherein said lignin-based sulfonic acid A1 has an average molar mass MW of at least 10,000 Da. Preferably, said lignin-based sulfonic acid A1 has an average molar mass MW of 10,000-100,000 Da.

Preferably, said lignin-based sulfonic acid A1 has a degree of sulfonation of from 1.0 to 2.5 mol per kilogram of said lignosulfonic acid.

The average molar mass MW of the lignin-based sulfonic acid used in this application is determined by gel permeation chromatography in accordance with DIN 55672-3.

The degree of sulfonation of said lignin-based sulfonic acid used in this application is calculated based on the sulfur content of said lignin-based sulfonic acid, which is determined by atomic emission spectroscopy, from which the sulfate content (which is determined in accordance with DIN 38405- D5-2).

Preferred lignin-based sulfonic acids A1 are lignosulfonic acid, ethoxylated lignosulfonic acid or oxidized lignins.

Preferred lignin-based sulfonic acids A1 are lignosulfonic acid, ethoxylated lignosulfonic acid or oxidized lignins.

In one embodiment, the microparticle compositions in accordance with the invention contain at least one anionic polymeric surfactant A2, wherein the surfactant A2 is homo- or copolymers of monoethylenically unsaturated monomers M1 that have a sulfonic acid group, optionally with one or several M2 comonomers that differ from the M1 monomers.

The anionic groups in these anionic polymeric surfactants may be partially or completely neutralized. Suitable counterions are alkali metal ions such as sodium, potassium, alkaline earth metal ions such as magnesium or calcium, and ammonium. In the case of anionic polymeric surfactants that have a sulfonate group, the anionic groups are preferably at least partially neutralized.

Preferably, the polymeric surfactant A2 is selected from homo- and copolymers obtained from:

I) at least one monoethylenically unsaturated monomer M1 having a sulfonic acid group, such as vinyl sulfonic acid, allyl sulfonic acid, styrene sulfonic acid, vinyl toluene sulfonic acid, (meth)acrylate monomers having a sulfonic acid group, such as 2-acryloxyethyl sulfonic acid, 2-acryloxypropyl sulfonic acid or 4-acryloxybutylsulfonic acid, and a (meth)acrylamide monomer having a sulfonic acid group, such as 2-acrylamidoethylsulfonic acid, 2-acrylamidopropylsulfonic acid or 2-acrylamido-2-methylpropanesulfonic acid;

II) and optionally one or more monoethylenically unsaturated comonomers M2, which differ from the monomers M1, such as styrene, C1-C ₄ alkyl acrylates, C1-C ₄ alkyl methacrylates, acrylamide, methacrylamide, acrylic acid, methacrylic acid, C1-C ₄ - alkyl acrylates, C1-C4 alkyl methacrylates.

In one embodiment, polymeric surfactant A2 is selected from homo- and copolymers derived from:

I) monomers M1, which are selected from (meth)acrylate monomers having a sulfonic acid group, such as 2-acryloxyethylsulfonic acid, 2-acryloxypropylsulfonic acid or 4-acryloxybutylsulfonic acid, and (meth)acrylamide monomer having a sulfonic acid group, such as 2-acrylamidoethylsulfonic acid acid, 2-acrylamidopropylsulfonic acid or 2-acrylamido-2-methylpropanesulfonic acid;

II) and optionally one or more monoethylenically unsaturated comonomers M2, which differ from the monomers M1, such as styrene, C1-C4 alkyl acrylates, C1-C4 alkyl methacrylates, acrylamide, methacrylamide, acrylic acid, methacrylic acid, C1-C4 alkyl acrylates, C1 -C4-alkyl methacrylates.

In particular, polymeric surfactant A2 contains, or is selected from homo and copolymers:

I) monomers M1, which are 2-acrylamido-2-methylpropanesulfonic acid;

II) and optionally one or more monoethylenically unsaturated comonomers M2, which differ from the monomers M1, such as styrene, C ₁ -C ₄ -alkyl acrylates, C ₁ -C _{4 -alkyl} methacrylates, acrylamide, methacrylamide, acrylic acid, methacrylic acid, C ₁ - C ₄ -alkyl acrylates, C ₁ -C ₄ -alkyl methacrylates.

In said preferred, particularly preferred or particularly preferred polymeric surfactants A.2, the amount of monomers M1 is preferably at least 50% by weight, based on the total amount of monomers forming the polymeric surfactant. Even more preferred are polymeric surfactants A that are homo- or copolymers of M1 monomers, wherein the amount of M1 monomers is at least 90% by weight based on the total amount of monomers forming the polymeric surfactant. Said polymers are known, for example, to be available on the market under the trade names Lupasol S and Lupasol PA 140.

In another specific group of embodiments, microparticle compositions in accordance with the invention contain group A3 surfactants, wherein the polymeric A3 surfactants are arylsulfonic acid-formaldehyde condensates, as well as arylsulfonic acid-formaldehyde-urea condensates, in particular condensates naphthalenesulfonic acid and formaldehyde.

Examples of polymer surfactants A3 include arylsulfonic acid-formaldehyde condensates and arylsulfonic acid-formaldehyde-urea condensates, such as naphthalene sulfonic acid-formaldehyde condensates, phenolsulfonic acid-formaldehyde condensates, cresol sulfonic acid-formaldehyde condensates, etc.;

In one embodiment, microparticle compositions in accordance with the invention contain at least one surfactant A1 and do not contain surfactant A2 or A3.

- 5 045461

In one embodiment, microparticle compositions in accordance with the invention contain at least one surfactant A1, at least one surfactant A2, and do not contain surfactant A3.

In one embodiment, microparticle compositions in accordance with the invention contain at least one surfactant A1, at least one surfactant A3, and do not contain surfactant A2.

In one embodiment, microparticle compositions in accordance with the invention contain at least one surfactant A1, at least one surfactant A2 and at least one surfactant A3.

The amount of anionic polymeric surfactants A1 to A3 in the composition is preferably from 0.1 to 50 wt.%, in particular from 2 to 40 wt.% and most preferably from 3 to 30 wt.% based on the total amount of saflufenacil and aminoplast polymer.

Polymer surfactants A1 to A3 are also referred to as polymer surfactants A in this application.

It has been found to be advantageous when the polymeric surfactants A1 to A3 are combined with one or more additional anionic surfactants B, which are different from them, which thereby provide stabilization of the aqueous microparticle formulation. Suitable anionic surfactant compounds B are surfactants that have one anionic group selected from phosphate or phosphonate groups and sulfate or sulfonate groups, the latter being preferred. Said surfactants B will typically be included in the microparticle composition in the form of their salts, in particular sodium, potassium or ammonium salts.

Examples of anionic surfactants B include salts of alkyl sulfonates, alkyl sulfate, alkyl phosphates, half-esters of alkoxylated alkanols with sulfuric acid or phosphoric acid, alkylaryl sulfonates, alkylaryl phosphates, half-esters of alkoxylated alkylphenols with sulfuric acid or phosphoric acid, and half-esters of alkoxylated mono-, di- or tristyrylphenols with sulfuric acid or phosphoric acid. Among these anionic surfactants B, the anionic surfactants of formula (I) are preferred.

R-(OA) _m -OX (I), where R is a hydrocarbon radical having from 8 to 40 carbon atoms and preferably from 12 to 30 carbon atoms, and optionally one oxygen atom;

And independently of each other is 1,2-ethylene, 1,2-propylene or 1,3-propylene, in particular 1,2-ethylene;

m is from 0 to 50, preferably from 0 to 30, and especially preferably from 0 to 20; And

X represents SO3M or PO ₃ M ₂ , wherein M is selected from H, alkali metal ions such as K and Na, alkaline earth metal ions such as % Ca and % Mg and ammonium.

Preferably, M is an alkali metal ion and in particular sodium.

Examples of suitable hydrocarbon radicals R having from 8 to 40 carbon atoms are alkyl having from 8 to 40 and preferably from 12 to 30 carbon atoms, phenyl, which may be substituted by one or two alkyl radicals having from 4 to 20 atoms carbon, phenyl, which is substituted with a phenoxy radical, wherein the phenyl and/or phenoxy may contain an alkyl radical having from 4 to 20 carbon atoms, a tristyrylphenyl radical, etc. In a preferred embodiment of the present invention, the radical R in formula I is a tristyrylphenyl radical.

Preference is given to anionic surfactants B, which are anionic surfactants of formula (I), with R, m and X having the following meanings:

R represents alkyl having from 8 to 30, in particular from 10 to 20 carbon atoms, m represents 0,

X is SO3M, wherein m is selected from alkali metal ions such as K and Na, alkaline earth metal ions such as % Ca and % Mg and ammonium. Preferably, M is an alkali metal and in particular sodium.

Particularly preferably, additional anionic surfactant B is an alkyl sulfate such as lauryl sulfate, in particular sodium lauryl sulfate.

In this case, the amount of anionic surfactant B, in particular the surfactant compound of formula (I), is preferably from 0.1 to 10% by weight, in particular from 0.3 to 7% by weight, and most preferably from 0.5 to 5 wt.%, based on the total amount of saflufenacil and aminoplast polymer. In this case, the amount of anionic surfactant B, in particular the surfactant compound of formula (I), is preferably

- 6 045461 is chosen such that the ratio of the mass of anionic polymeric surfactant A to the mass of anionic surfactant B is from 1:1 to 20:1, in particular from 2:1 to 10:1.

In one embodiment, the microparticle compositions of the invention contain at least one surfactant A1 and no surfactant A2 or A3, and the anionic surfactant B is sodium lauryl sulfate.

In one embodiment, the microparticle compositions of the invention contain at least one surfactant A1, at least one surfactant A2 and no surfactant A3, and the anionic surfactant B is sodium lauryl sulfate.

In one embodiment, microparticle compositions according to the invention contain at least one surfactant A1, at least one surfactant A3 and no surfactant A2, and the anionic surfactant B is sodium lauryl sulfate.

In one embodiment, the microparticle compositions in accordance with the invention contain at least one surfactant A1, at least one surfactant A2 and at least one surfactant A3, and the anionic surfactant B is lauryl sulfate sodium

The compositions according to the invention may also contain a non-ionic surfactant (non-ionic surfactant). Preferred nonionic surfactants include neutral surfactants of formula (II) R'-(O-B)n-OH (II) wherein R' is a hydrocarbon radical having from 8 to 40 and more preferably from 12 to 30 atoms carbon, and optionally one oxygen atom,

B is a C ₂ -C ₄ -alkane-1,2-diyl such as 1,2-ethylene, 1,2-propylene or 1,2-butylene or a combination thereof, and more preferably 1,2-ethylene or thereof combination with 1,2-propylene, and n is 3 to 100, preferably 4 to 50, and more preferably 5 to 40.

Preferred nonionic surfactants include block copolymers of ethylene oxide (EO) and propylene oxide (PO). Such block copolymers may, for example, have the structure R(EO)x-(PO)y-(EO)z, wherein R is H or a C ₄ -C ₃₀ alkyl moiety, and x, y, z are independently numbers from 2 to 100.

Examples of suitable hydrocarbon radicals R' include those mentioned for R. In a preferred embodiment of the invention, the radical R' is a phenyl radical substituted with one C ₄ -C ₁₈ alkyl group.

In this case, the amount of non-ionic surfactant, in particular the surfactant compound of formula (II), is preferably from 1 to 150 g/l, in particular from 2 to 60 g/l in the resulting formulation. In one particular embodiment of the invention, the composition does not contain a nonionic surfactant, or contains a nonionic surfactant in an amount of less than 1 wt.%, in particular less than 0.5 wt.%, based on the total amount of saflufenacil and aminoplast polymer.

In certain groups of embodiments, the microparticle composition is presented in the form of an aqueous suspension. Such a suspension contains microparticles of solid saflufenacil as a dispersed phase, and an aqueous medium as a dispersion medium.

The aqueous suspension can be prepared using the microparticle composition process described in this application. It can also be obtained by redispersing in an aqueous medium a solid microparticle composition as described in this application.

The term aqueous medium refers to the liquid phase of the composition and contains a water-based solvent and, optionally, compounds that are dissolved therein, for example surfactants as mentioned above, and in this case, usually one or more conventional formulation additives such as as thickeners or biocides. The water-based solvent in an aqueous suspension is either water or a mixture thereof with a water-miscible organic solvent such as C1- _C4 alkanols, e.g. methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol , isobutanol, or tert-butaiol, C ₂ -C ₅ -alkanediols and C ₃ -C ₈ -alcantriols, preferably selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, glycerol and 1, 4butanediol. Typically, the amount of water in the water-based solvent is at least 50% by weight, in particular at least 80% by weight or at least 90% by weight, based on the water-based solvent. The water-based solvent may consist primarily of water, that is, water constitutes at least 95% by weight of the total amount of solvent that is present in the suspension. The water-based solvent may also be a mixture of the above-mentioned water-miscible organic solvent and water. In the latter case, the ratio of the mass of water to the mass of water-miscible organic solvent in the water-based solvent is preferably

- 7 045461 range from 99:1 to 1:1; more preferably in the range of 50:1 to 3:1; and most preferably in the range of 20:1 to 4:1. In other words, the amount of the organic solvent may be from to 50% by weight, more preferably from 2 to 25% by weight, and most preferably from 5 to 20% by weight, based on the total weight of the water-based solvent.

The aqueous suspension will typically contain microparticles in an amount of at least 5 wt.%, and such amount may be up to 50 wt.% or even higher, in each case, based on the total weight of the aqueous suspension and in terms of the total amount of aminoplast polymer and saflufenacil. Often, the aqueous suspension will contain microparticles in an amount of from 10 to 45% by weight, in particular from 20 to 40% by weight, in each case based on the total weight of the aqueous suspension and based on the total amount of aminoplast polymer and saflufenacil. The concentration of saflufenacil in the aqueous suspension will often be in the range of 5 to 40% by weight, in particular 15 to 30% by weight, based on the total weight of the aqueous suspension.

In this case, the concentration of polymeric anionic surfactant A in the aqueous suspension will often be in the range of 0.1 to 15% by weight, in particular 0.2 to 6% by weight, based on the total weight of the aqueous suspension of microparticles.

In this case, the concentration of anionic surfactant B in the aqueous suspension will often be in the range of 0.1 to 15% by weight, in particular 0.2 to 6% by weight, based on the total weight of the aqueous suspension of microparticles.

The aqueous compositions according to the invention may also contain conventional formulation auxiliaries, such as viscosity modifying agents (thickeners), antifoams, preservatives, buffer solutions, inorganic dispersants, etc., which are commonly used in aqueous herbicide formulations . Such excipients can be added to the aqueous suspension after Step III) of the production process described in this application has been carried out. The amount of additives will generally not exceed 10% by weight, in particular 5% by weight, based on the total weight of the aqueous suspension. Suitable inorganic dispersants, also called anti-caking agents, which serve to prevent microparticles from sticking together are silica (eg, such as Sipemat® 22 from Degussa), alumina, calcium carbonate and the like. In the context of the present invention, the preferred inorganic dispersant is silica. The concentration of inorganic dispersants in the resulting suspension will generally not exceed 2 wt.%, based on the total mass of the resulting suspension, and in this case is preferably in the range from 0.01 to 2 wt.%, in particular from 0.02 up to 1.5 wt.% and, in particular, from 0.1 to 1 wt.%, based on the total weight of the resulting formulation.

Suitable thickeners are compounds that affect the fluidity of the suspension concentrate and can help stabilize the aqueous suspension of microparticles against caking. In this regard, mention may be made, for example, of commercially available polysaccharide-based thickeners such as methylcellulose, carboxymethylcellulose, hydroxypropylcellulose (Klucel® grades), xanthan gum (for example, commercially available as Kelzan® grades from Kelco, or form Rhodopol® grades from Rhodia), synthetic polymers such as acrylic acid based polymers (Carbopol® grades), polyvinyl alcohol (e.g. Mowiol® and Poval® grades from Kuraray) or polyvinyl pyrrolones, silicic acid or phyllosilicates such such as montmorillonite and bentonites, which can be hydrophobized (available on the market as Attaclay® grades and Attaflow® grades from BASF SE; or as Veegum® grades and Van Gel® grades from R.T. Vanderbilt). In the context of the present invention, the preferred thickener is xanthan gum. The concentration of thickeners in the aqueous suspension will generally not exceed 2 wt.%, based on the total weight of the aqueous suspension, and is preferably in the range from 0.01 to 2 wt.%, in particular from 0.02 to 1.5 wt. .% and, in particular, from 0.1 to 1 wt.%, based on the total weight of the aqueous suspension or the resulting formulation, respectively.

Antifoam agents suitable for the compositions according to the invention are, for example, silicone emulsions (such as, for example, Silicone SRE-PFL from Wacker or Rhodorsil® from Bluestar Silicones), polysiloxanes and modified polysiloxanes, including polysiloxane block- polymers such as the products FoamStar® SI and FoamStar® ST from BASF SE, long-chain alcohols, fatty acids, organofluorine compounds and mixtures thereof.

Suitable preservatives for preventing microbial damage to the compositions according to the invention include formaldehyde, alkyl esters of p-hydroxybenzoic acid, sodium benzoate, 2-bromo-2-nitropropane-1,3-diol, o-phenylphenol, thiazolinones such as benzisothiazolinone, 5 -chloro-2-methyl-4-isothiazolinone, pentachlorophenol, 2,4-dichlorobenzyl alcohol and mixtures thereof. Commercially available isothiazolinone preservatives are, for example, sold under the brand names Proxel® (Arch Chemical Company), Acticide® MBS (Thor Chemie Company) and Kathon® MK (Rohm & Haas Company).

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If necessary, the compositions according to the invention, in particular aqueous suspensions, may contain buffer solutions to adjust the pH level. Examples of buffer solutions are alkali metal salts of weak inorganic or organic acids, such as, for example, phosphoric acid, boric acid, acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid and succinic acid.

In addition, the compositions according to the invention, in particular aqueous suspensions, can be formulated using conventional binders, for example, aqueous polymer dispersions, water-soluble resins, for example water-soluble alkyd resins, or waxes.

The compositions according to the invention may also contain one or more adjuvants. Suitable adjuvants are known to those skilled in the art and include surfactants, vegetable oil concentrates, adhesives, wetting agents, and penetration agents. In other special groups of embodiments, the microparticle composition is in the form of a solid composition. Such a solid composition contains microparticles of solid saflufenacil, optionally one or more surfactants, in particular polymeric surfactant A and optionally anionic surfactant B, and optionally an inert solid carrier material.

Solid compositions, for example, may be redispersible powders, water-dispersible granules, wettable powders, and the like.

Solid carriers, for example, include natural minerals such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, ferruginous clay, loess, clay, dolomite, diatomite, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and plant products such as grain flour, bark flour, wood and nut shell flour, cellulose powders, or other solid carriers.

The solid compositions of the invention may also contain conventional formulation auxiliaries such as antifoams, preservatives, buffers, inorganic dispersants, etc., which are commonly used in solid herbicide formulations. Such excipients may be incorporated into the solid formulation at any conventional stage of the process for its manufacture. The amount of additives will generally not exceed 10% by weight, in particular 5% by weight, based on the total weight of the solid composition.

The solid composition can be prepared from an aqueous suspension that is first formed in the process of preparing the microparticle composition as described in this application by removing the aqueous phase from the aqueous suspension. Removal of the aqueous phase can be achieved either by separating the aqueous phase from the solid microparticles, for example by centrifugation or filtration. Preferably, the aqueous phase is removed using an evaporation process such as spray drying or freeze drying.

As stated above, the method for preparing the composition comprises a first step in which an aqueous suspension of saflufenacil particles is provided. For this purpose, solid saflufenacil is suspended in an aqueous solvent, in particular water. The water-based solvent may contain one or more surfactants, in particular at least one polymeric surfactant A1, which is expected to act as a protective colloid, and optionally one or more anionic surfactants B.

Preferably, the particle size of the saflufenacil particles in the aqueous suspension before encapsulation is less than 45 μm, in particular it will not exceed 40 μm, preferably will not exceed 30 μm, and in particular will not exceed 25 μm. The particle size shown is the so-called d90 value. Preferably, the active substance particles have an average particle diameter, which in this application is also referred to as a d50 value, ranging from 0.5 to 25 μm, in particular from 1 to 20 μm, in particular from 1.5 to 15 μm. The d50 value is defined as the value that is above the 50 wt.% particle diameters and below the 50 wt.% particle diameters. The d10 value is preferably at least 0.5 μm and, for example, can be in the range from 0.5 to 10 μm, in particular from 1 to 5 μm. The d90 value as well as the d50 value can be calculated from the particle size distribution of saflufenacil, which can be determined using traditional methods such as dynamic or static light scattering, at a temperature of 25°C and a concentration ranging from 0.1 up to 1 wt.%.

It has been found to be advantageous when the polycondensation is initiated or carried out in the presence of at least one anionic polymer surfactant A2. Polymer surfactant A2 will often be in the range of 0.1 to 10% by weight, in particular 1 to 6% by weight, based on the total weight of the aqueous suspension.

It has been found to be advantageous when the aqueous suspension of step I) also contains at least one anionic surfactant B, in particular an anionic surfactant which contains or is selected from the surfactants of formula (I). In this case, the concentration of anionic surfactant B in the aqueous suspension of step I) will often be in the range from 0.01 to 2 wt.%, in particular from 0.1 to 1 wt.%, based on total mass of the aqueous suspension.

An aqueous suspension of saflufenacil particles can be provided in analogy with known methods for preparing an aqueous suspension of saflufenacil, for example, those described in WO 2011/023759.

In one embodiment, stage I) includes stage I.a) and stage T.b). In step I.a), solid saflufenacil, in particular a crystalline form of saflufenacil, for example saflufenacil anhydrate, or one of the hydrate forms, and a water-based solvent and optionally at least a portion of the surfactant are mixed in any conventional mixing device, which able to provide sufficient shear forces to form the desired suspension. Suitable mixing devices include, but are not limited to, high shear mixers such as the Ultra-Turrax, static mixers such as mixing nozzle systems, bead mills, colloid mills, cone mills and other homogenizers. Generally, the order in which the individual components are combined does not matter. In this case, it may be advantageous to carry out step I.a), in particular by mixing a water-based solvent and at least part of a surfactant, for example a surfactant of group A and optionally a surfactant B, until a homogeneous mixture is obtained, and then adding solid saflufenacil with shear to said homogeneous mixture. The mixture resulting from step I.a), that is, the coarse suspension of saflufenacil in the water-based solvent of step I.6), is then subjected to a suitable agent to reduce the size of the saflufenacil particles present in the mixture, typically to less than 40 μm, preferably to less than 30 µm and in particular up to less than 20 µm (d90 value), for example up to a particle size (d90) in the range from 0.5 to 15 µm. Step I.6) may be carried out by any physical attrition method such as grinding, crushing or grinding, in particular by wet grinding or wet grinding, including, for example, bead milling, hammer milling, jet milling, grinding with air classification, pin grinding, cryogenic grinding methods and the like. Stages I.a) and T.b) are usually performed sequentially. However, it is also possible to perform these steps together.

In another embodiment of the invention, step I) includes providing saflufenacil in powder form, wherein the d90 value of the powder particles is less than 40 μm and, in particular, not more than 30 μm or not more than 20 μm, for example the particle size (d90) is in range from 1 to <40 µm, in particular 1-30 µm or 1-20 µm. The powder is typically prepared by grinding solid saflufenacil, such as an anhydrate or crystalline hydrate, through a conventional dry grinding method, such as air grinding, to a powder having the desired particle size. The powder thus obtained is then suspended in a water-based solvent or in an aqueous solution of surfactant group A and optionally surfactant B.

In one embodiment, polymeric surfactants A2 are added to the saflufenacil suspension provided in step I) before starting or initiating or carrying out polycondensation, in particular before adding the aminoplast precondensate thereto. In particular, it may be preferable to maintain the aqueous suspension of saflufenacil containing polymeric surfactant A2 for some time, for example, for 10-180 minutes, before starting polycondensation, while polymeric surfactant A1 is added only after stage I ). In Stage II), an aminoplast precondensate is added to the aqueous suspension of Stage I), which, when cured in Stage III), forms a solid, water-insoluble aminoplast polymer that encloses or surrounds the solid particles of saflufenacil, since polycondensation preferentially occurs on the surface of the solids. saflufenacil particles.

The amount of aminoplast precondensate added in step II) is selected to achieve the desired amount of aminoplast polymer in the resulting microparticle composition. In fact, the amount added corresponds to the amount of aminoplast resin in the microparticles, taking into account that the mass is reduced by the amount of water that is formed during polycondensation, and is usually in the range of 0.5-40 wt.%, in particular from 1 to 35 wt. .% and, in particular, from 5 to 25 wt.% based on saflufenacil and in terms of organic material.

Suitable precondensates that may be added in step II) include melamine-formaldehyde precondensates, including fully or partially esterified melamine-formaldehyde precondensates, urea-formaldehyde precondensates, thiourea-formaldehyde precondensates, melamine-urea-formaldehyde precondensates (MUF resins), including including mixtures of fully or partially esterified melamine and formaldehyde precondensates and urea and formaldehyde precondensates, urea and glutaraldehyde precondensates, benzoguanamine and formaldehyde precondensates, mixtures of dicyandiamide and formaldehyde and urea and glyoxal polycondensates. Suitable aminoplast precondensates for microencapsulation are known and can be found, among others, in Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd edition, vol. 2, pp. 440-469, in

- 10 045461 prior art cited in the introduction, US 4918317, EP 26914, EP 218887, EP 319337, EP 383337, EP 415273, DE 19833347, DE 19835114 and WO 01/51197. Suitable ones are available on the market, for example precondensates of the Cymel type, such as, but not limited to, Cymel®303, 327, 328 or 385 (esterified melamine-formaldehyde resins from Cytec), Maprenal® type, such as, but not limited to, Maprenal®MF 900w/95, MF 915/75IB, MF 920/75WA, MF 921w/85WA, (esterified melamine-formaldehyde resins from Ineos), such as Kauramin® from BASF SE, such as, but not limited to, Kauramin ® 783, Kauramin® 792 or Kauramin® 753 (melamine-formaldehyde resins), Kauramin® 620 or Kauramin® 621 (melamine-urea-formaldehyde resins), Kaurit® type from BASF SE, such as, but not limited to, Kaurit® 210 , 216, 217 or 220 (urea-formaldehyde resins), Luracoll® type, such as Luracoll® SD (esterified melamine-formaldehyde resins), Luwipal® type, such as, but not limited to, Luwipal® 063, Luwipal® 069 ( esterified melamine-formaldehyde resins), or Plastopal® type, such as, but not limited to, Plastopal® BTM, Plastopal® BTW (esterified urea-formaldehyde resins).

In suitable urea-formaldehyde or thiourea-formaldehyde precondensates, the molar ratios of urea or thiourea to formaldehyde are generally in the range of 1:0.8 to 1:4, in particular 1:1.5 to 1:4, in in particular from 1:2 to 1:3.5.

In suitable precondensates of melamine and formaldehyde or melamine, (thio)urea and formaldehyde, the molar ratios of melamine to formaldehyde are generally in the range from 1:1.5 to 1:10, in particular from 1:3 to 1:8 preferably from 1:4 to 1:6.

In suitable precondensates of melamine and formaldehyde or melamine, (thio)urea and formaldehyde, the molar ratios of melamine + urea or thiourea to formaldehyde are generally in the range of 1:0.8 to 1:9, in particular 1:2 to 1:8, preferably from 1:3 to 1:6. The molar ratio of urea or thiourea to melamine is usually in the range from 5:1 to 1:50 and in particular from 30:1 to 1:30.

Precondensates can be used in the form of esterified precondensates of an amino compound and an aldehyde. In said esterified precondensates, methylol groups formed by the reaction of amino groups with formaldehyde with an alkanol or alkanediol, in particular with a C1-C4 alkanol, such as methanol, ethanol, n-propanol or n-butanol, in particular methanol, or C ₂ - C ₄ alkanediol such as ethylene glycol. The degree of esterification of these resins can be controlled by the molar ratio of amino groups to alkanol, which is typically in the range of 10:1 to 1:10, preferably in the range of 2:1 to 1:5.

Most preferably, the precondensates are selected from the group consisting of melamine-formaldehyde resins, including fully or partially esterified melamine-formaldehyde precondensates, and urea-formaldehyde precondensates, and mixtures thereof. In particular, the pre-condensate is a fully or partially esterified condensate of melamine and formaldehyde, which may contain a small amount of urea, for example 1-20 mol%, based on the melamine.

The addition of the precondensate to the aqueous suspension is typically accomplished by adding the precondensate in the form of an aqueous or alcoholic solution of the precondensate to the aqueous suspension, or by mixing suitable amounts of the dissolved precondensate. Preferably, to achieve a uniform distribution of the precondensate in the aqueous suspension, suitable mixing devices such as stirrers or in-line mixers are used. It may be preferable to add the precondensate, preferably in the form of a solution, to the aqueous suspension of saflufenacil with stirring. Preferably, the addition of the precondensate is carried out under conditions in which the polycondensation reaction is slow or does not occur at all, for example, either in the case where the pH value of the aqueous suspension is at least 6, for example in the range of pH 6 to pH 10, or in the case when the temperature does not exceed 30°C, or in both cases.

Polycondensation of the aminoplast precondensate can be carried out or initiated in a well known manner, for example by heating the aqueous suspension to a certain reaction temperature, at a pH value at which polycondensation occurs at that reaction temperature.

During polycondensation, the aminoplast precondensate is converted to a water-insoluble aminoplast resin, which precipitates from the aqueous phase and preferentially deposits on the surface of the saflufenacil solids, thereby enclosing or surrounding the saflufenacil solids. As a result, it is possible to achieve effective encapsulation even with small amounts of aminoplast precondensate. Preferably, the polycondensation of the aminoplast is carried out at a pH value of less than 6, in particular at a pH value of no more than 5, for example in the pH range from 0 to 6, in particular in the pH range from 1 to 5, or pH values from 2 to 4.

The pH of the aqueous suspension is usually adjusted by adding suitable amounts of organic or inorganic acid such as sulfuric acid, hydrochloric acid, phosphoric acid, carboxylic acid including alkanoic acids, alkane dicarboxylic acids or hydroxy carboxylic acids such as formic acid, acetic acid , propionic acid, oxalic acid, malic acid or citric acid and alkyl or arylsulfonic acids such as methanesulfonic acid or toluenesulfonic acid. It is preferred if at least part, in particular most of the acid is present in the aqueous suspension before the aqueous suspension is heated to the reaction temperature.

Preferably, the polycondensation of the aminoplast precondensate is carried out at an elevated temperature, in particular at a temperature of at least 30°C, in particular at least 40°C or at least 50°C, for example at a temperature in the range from 30 to 100 °C, in particular in the range from 40 to 95°C or in the range from 50 to 90°C. It may be possible to start the polycondensation of the aminoplast at a relatively low temperature, for example at a temperature in the range of 30 to 65°C or 35-60°C, and then complete the polycondensation reaction at a higher temperature, for example in the range of 50-100°C or 60-90°C. The time required to complete the polycondensation may vary depending on the reactivity of the precondensate, the temperature and pH of the aqueous suspension, and may take from 1 to 24 hours, in particular from 2 to 12 hours. Preferably, the polycondensation reaction is at least partially carried out at temperatures of at least 50°C, in particular at least 60°C, for example for 1-8 hours, at a temperature in the range from 50 to 100°C, in particular 60-90°C.

The aqueous suspension of saflufenacil microparticles thus obtained can be neutralized by adding a base. Preferably, the pH of the suspension is adjusted to a pH value of at least 6, for example to a pH value in the range from 6 to 10, in particular in the range of pH values from 6.5 to 9.0. In one preferred embodiment, the base used is ammonia, in particular aqueous ammonia.

From the aqueous suspension thus obtained, the microparticles can be isolated, for example, by filtration or centrifugation, or the aqueous suspension can be spray-dried, granulated or lyophilized to obtain a solid composition in the form of a powder or granules. The solid composition can be redispersed or formulated using excipients as described above.

The aqueous suspension can also be used as such or formulated as a liquid formulation, for example, as a suspension, using suitable formulation auxiliaries as described above, such as, for example, thickeners, anionic surfactants B, non-ionic surfactants and/ or biocides.

The invention also relates to applications of the microparticle composition according to the invention for the protection of agricultural plants and to methods of controlling unwanted vegetation, which include the application of formulations, in diluted or undiluted form, to plants, their environment and/or seeds.

The compositions according to the invention provide very good vegetation control in non-crop areas, in particular at high application rates. However, generally higher application rates are not required than conventional non-encapsulated saflufenacil formulations to achieve similar control.

Among crops such as soybeans, cotton, oilseed rape, flax, lentils, rice, sugar beets, sunflowers, tobacco and cereals such as corn or wheat, the compositions according to the invention are active against broadleaf weeds and grass weeds, and cause less harm to agricultural plants compared to conventional formulations of non-encapsulated saflufenacil. This effect is especially noticeable at low application rates. Moreover, the compositions in accordance with the invention provide long-lasting residual activity, which in this case exceeds the residual activity of conventional formulations of non-encapsulated saflufenacil.

The compositions according to the invention have exceptional herbicidal activity against unwanted vegetation, in particular against a wide range of economically important noxious monocotyledonous and dicotyledonous weeds.

Mentioned below are some representatives of monocotyledonous and dicotyledonous weeds that can be controlled using compositions according to the invention, without limiting the listing to certain species.

In one embodiment, the compositions in accordance with the invention are used to control monocotyledonous weeds.

Examples of monocotyledonous weeds on which compositions according to the invention are effective are selected from the genus

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Hordeum spp.,

Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp. ., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..

Preferred examples of monocotyledonous weeds on which the compositions of the invention are effective are selected from:

Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum , Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.

Particularly preferred examples of monocotyledonous weeds on which the compositions according to the invention are effective are selected from the species

Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp.

In one embodiment, the compositions in accordance with the invention are used to control dicotyledonous weeds.

Examples of dicotyledonous weeds on which the compositions according to the invention are effective are selected from the genus Amaranthus spp.,

Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp.,

Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp. ., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sida spp., Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp., Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Pieris spp., Trifolium spp., Galinsoga spp. , Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp. Bidens spp., Veronica spp., and Hypochaeris spp..

Preferred examples of dicotyledonous weeds on which the compositions of the invention are effective are selected from:

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Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum officinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, La mium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, S ida spinosa Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L., Epilob Ium paniculatum, Cardamine spp, Pieris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria matriccarioides, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaeris radicata.

Particularly preferred examples of dicotyledonous weeds on which the compositions according to the invention are effective are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.

Depending on the method of application in question, the formulations according to the invention can also be used among other crop plants for the purpose of removing unwanted plants. Suitable crops are, for example, the following:

Allium sulfur, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. Silvestris, Brassica Oleracea, Brassica Nigra, Camellia Sinensis, Carthamus Tinctorius, Carya Illinoinse, Citrus Limon, Citrus Sinensis, Coffee Arabica (Coffee Canephora, Coffee L iberica), Cucumis sativus, Cynodon Dactylon, Daucus Carota, Elaeis Guineensis, Fragaria Vesca, Glycine Max , Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec. , Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca , Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes Sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In this case, the preferred crops are

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Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus,

Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis , Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Particularly preferred crops are cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or perennial crops.

In addition, the compositions in accordance with the invention can also be used among crops that, as a result of selection, including genetic engineering methods, tolerate the action of herbicides.

Moreover, the compositions in accordance with the invention can also be used among crops that, as a result of selection, including genetic engineering methods, suffer damage from insects or fungi.

The compositions in accordance with the invention can also be used among crops that have been modified by mutagenesis or genetic engineering in order to impart a new trait to the plant or modify an existing trait.

The term crops, as used in this application, also includes (crop) plants that have been modified by mutagenesis or genetic engineering in order to impart a new trait to the plant or modify an existing trait.

Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, as well as site-directed mutagenesis techniques to create mutations at a specific locus in the plant genome. Site-directed mutagenesis techniques often use oligonucleotides or proteins such as CRISPR/Cas, zinc finger nucleases, TALEN nucleases (transcription activator-like effector nucleases) or meganucleases to achieve targeted effects.

Genetic engineering typically uses recombinant DNA techniques to create modifications in a plant's genome that would not naturally be readily produced through crossbreeding, mutagenesis, or natural recombination. Typically, one or more genes are inserted into a plant's genome in order to add a trait or improve a trait. In the prior art, these integrated genes are also called transgenes, and plants containing such transgenes are called transgenic plants. The process of plant transformation usually causes several transformation events that differ by the genomic locus into which the transgene was integrated. Plants containing a specific transgene at a specific genomic locus are usually described as plants containing a specific event, which is designated by a specific event name. Traits that have been introduced into plants or modified include tolerance to certain herbicides, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

Tolerance to herbicides has been created through mutagenesis and also through genetic engineering. Plants that have been made tolerant to acetolactate synthase (ALS) inhibitor herbicides through traditional mutagenesis and selective breeding techniques include plant varieties commercially available under the name Clearfield®. However, most herbicide tolerance traits have been created through the use of transgenes.

Tolerance has been developed to a number of herbicides, such as glyphosate, glufosinate, 2,4-D, dicamba, oxynyl herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4hydroxyphenylpyruvate dioxygenase inhibitor herbicides ( HPPD), such as isoxaflutole and mesotrione.

Transgenes that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for glufosinate tolerance: pat and bar, for 2,4-tolerance D: aad-1 and aad-12, for dicamba tolerance: dmo, for oxynyl herbicide tolerance: bxn, for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA, for for tolerance to herbicides based on ALS inhibitors: csr1-2, for tolerance to herbicides based on HPPD inhibitors: hppdPF, W336 and avhppd-03.

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Maize transgenics containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832,

MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485,

VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3,

MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean objects containing herbicide tolerance genes, for example, but not excluding others, include GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

Transgenic objects of cotton containing herbicide tolerance genes, for example, are, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN1 0224 , MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

Canola transgenics containing herbicide tolerance genes include, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3 .

Insect resistance has largely been created by transferring bacterial genes for insecticidal proteins to plants. The most commonly used transgenes are Bacillus spec toxin genes and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, plant-derived genes have also been transferred to other plants, in particular genes encoding protease inhibitors such as CpTI and pinII. In another approach, transgenes have been used to produce double-stranded RNA in plants to target and negatively regulate insect genes. An example of such a transgene is dvsnf7.

Maize transgenics containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 411 4, 5307 , 59122, TS1507, TS6275, SVN-351, MIR162, DBT418 and MZIR098.

Soybean transgenics containing insecticidal protein genes include, but are not limited to, MON87701, MON87751, and DAS-81419.

Transgenic objects of cotton containing genes for insecticidal proteins, for example, are, but not excluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, SOT67B, SOT 102, T303-3, T304-40, GFM cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

Increased yield was created by increasing heading biomass through the use of the athb17 transgene present in the maize transgenic MON87403, or by increasing photosynthesis through the use of the bbx32 transgene present in the soybean transgenic MON87712.

Crop crops having modified oil content have been developed through the use of transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-lA and fatb1-A. Transgenic soybean entities containing at least one of these genes are: 260-05, MON87705 and MON87769.

Abiotic tolerance, particularly drought tolerance, was generated through the use of the cspB transgene contained in the maize transgenic MON87460 and through the use of the Hahb-4 transgene contained in the soybean transgenic IND-00410-5.

Traits are often combined by combining genes in a transformation event or by combining different events during the selection process. The preferred combination of traits is herbicide tolerance for different groups of herbicides, insect tolerance for different insect species, particularly lepidopteran and coleopteran insect tolerance, herbicide tolerance with one or more types of insect resistance, herbicide tolerance with increased yield, as well as a combination of herbicide tolerance and tolerance to abiotic conditions.

Plants containing single or packaged traits, as well as the genes and events that provide these traits, are well known in the art. For example, detailed information regarding mutagenized or integrated genes and related events is available on the websites of the International Service for the Acquisition of Agri-biotech Applications (ISAAA)'' (http://www.isaaa.org/gmapprovaldatabase) and Center for Environmental Risk Assessment (CERA) (http://ceragmc.org/GMCropDatabase), as well as in patent applications such as EP 3028573 and WO 2017/011288.

Application of compounds of formula (I) or formulations or combinations according to the invention containing them to crops can lead to effects specific to the crop that contains a particular gene or event. These effects may include changes in growth patterns or altered resistance to biotic or abiotic stressors. Such effects may include, but are not limited to, increased yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasmic, viral or viroid pathogens, as well as early plant vigor, early or delayed maturation, cold or heat tolerance, and also altered composition or content of amino acids or fatty acids.

Moreover, plants also include plants that, due to the use of recombinant DNA techniques, contain modified amounts of constituents or new constituents, in particular intended to improve the production of raw materials, for example potatoes that produce increased amounts of amylopectin (for example, Amflora potatoes, BASF SE , Germany).

Moreover, it has been found that the compositions according to the invention are also suitable for defoliation and/or desiccation of plant parts of agricultural crops such as cotton, potatoes, oilseed rape, sunflower, soybeans or broad beans, in particular cotton. In this regard, formulations and/or combinations for desiccation and/or defoliation of agricultural crops, methods for making said formulations and/or combinations, as well as methods for desiccation and/or defoliation of plants through the use of compositions in accordance with the invention have been provided.

As desiccants, the compositions according to the invention are particularly suitable for the desiccation of above-ground parts of agricultural plants such as potatoes, oilseed rape, sunflower and soybeans, as well as cereals. This makes fully mechanized harvesting of these important crops possible.

Also of economic interest is the ease of harvesting that becomes possible as a result of concentrating fruit cracking over a certain period of time, or reducing the adhesion to the tree of citrus fruits, olives and other types and varieties of scarce fruits, stone fruits and nuts. The same mechanism, that is, stimulating the development of separating tissue between the fruiting part or the leaf part and the cutting part of the plants, is also important for the controlled defoliation of useful plants, in particular cotton.

Moreover, reducing the time it takes individual cotton plants to mature results in improved fiber quality after harvest.

Moreover, it has been found that the compositions according to the invention are also suitable for the control of conifers, in particular conifer seedlings that grow naturally, and in particular for the control of pine seedlings that grow naturally.

In general, the compositions in accordance with the invention, which are described in this application, are suitable for the control of unwanted vegetation. For this purpose, the compositions can be used as such or they are preferably used after dilution with water. Preferably, for various end-user applications, a so-called aqueous spray solution is prepared by diluting the compositions according to the present invention with water, for example tap water. Spray solutions may also contain additional constituent components in dissolved, emulsified or suspended form, for example fertilizers, active ingredients of other groups of herbicidal or growth-regulating active ingredients, additional active ingredients, for example, active ingredients for the control of animal pests or phytopathogenic fungi or bacteria, in addition, mineral salts, which are used to reduce the lack of nutrients and microelements, as well as non-phytotoxic oils or oil concentrates. Typically, these constituent components are added to the spray mixture before, during or after dilution of the compositions in accordance with the invention.

The compositions according to the invention can be applied pre-emergence or post-emergence. If saflufenacil is less well tolerated by certain crop plants, application methods may be used in which the herbicidal compositions are sprayed using a sprayer so that the leaves of sensitive crop plants do not come into contact with them as much as possible, and the active substances reach the leaves of undesirable plants that grow below, or bare soil surface (soil-directed spraying, soil application).

Depending on the purpose of the control measures taken, the season, the target plants and the stage of growth, the compositions according to the invention are applied in such a way that the application rates of saflufenacil range from 0.001 to 3.0, preferably from 0.01 to 1.0 kg/ha of active substances (a.v.).

To broaden the spectrum of action and to obtain a synergistic effect, the compositions in accordance with the invention can be mixed with a number of representatives of other groups of herbicidal or growth-regulating active substances and used together with them.

Examples of suitable mixture partners are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2 -(getaro

- 17 045461 yl/aroyl)-1,3-cyclohexanediones, heteroarylaryl ketones, benzyl isoxazolidinones, metaCF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexene oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzo furans, dihydrofuran- 3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, complex aryloxy- and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxy amides and uracils .

It is also possible to use the compositions in accordance with the present invention as a tank mix partner with other formulations. Thus, the compositions according to the invention can be mixed and used together with a number of different formulations of pesticide compounds, for example, with formulations that contain active ingredients or adjuvants, such as atrazine, glyphosate, glufosinate, S-metolachlor, ester 2 ,4-D, isoxaflutole, diflufenzopyr, dicamba, mesotrione, dimethenamid-P, pendimethalin, imazethapyr, paraffin oils, fatty acid polyhydric alcohol esters, polyethoxylated fatty acid polyhydric alcohol esters, ethoxylated alkylaryl phosphates, methylated seed oils, emulsifying agents, ammonium sulfate and mixtures thereof.

Moreover, it may be advantageous to use saflufenacil-containing compositions according to the invention, alone or in combination with other herbicides, as a mixture together with other additional plant protection agents, for example with agents intended to control pests or phytopathogenic fungi or bacteria. Also of interest is miscibility with solutions of mineral salts, which are used to reduce the deficiency of nutrients and microelements.

In this case, non-phytotoxic oils and oil concentrates can also be added.

The present invention offers the following advantages:

It is easy and cost-effective to implement.

The compositions according to the invention can be mixed with a wide range of other pesticides and their formulations, in particular with herbicides having a water solubility of at least one g/l, such as auxins, bentazone, diquat and paraquat and their formulations. In particular, miscibility is achieved with dicamba, glyphosate, glufosinate, MCPA, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, bentazone, diquat and paraquat, and their formulations.

The compositions in accordance with the invention demonstrate both high physical stability and high chemical stability over long periods of storage, while maintaining their biological effectiveness.

When diluted with water, the compositions of the invention provide stable aqueous compositions of saflufenacil and produce little or no coarse material or supernatant.

The following examples are intended to further illustrate the present invention without limiting its scope in any way.

Examples

I. Analytical methods.

Particle size distribution (PSD) was determined using statistical laser scattering using a Malvern Mastersizer 200 in accordance with the European standard ISO 13320 EN. Data were processed according to Mie theory using software provided by Malvern Instruments using a universal model. The important parameters are the dn values, where n = 10, 50 and 90, that is, the values d10, d50 and d90.

The solids content of the resulting dispersion was determined by evaporating the volatiles of a small sample of an aqueous suspension in a drying chamber at 105° C. for 2 hours. Each value reported for the examples represents the average of three parallel experiments.

II. Components.

Antifoaming agent 1: Silicone oil emulsion based antifoaming agent.

Antifoam 2: Antifoam emulsion containing polydimethylsiloxane.

Biocide 1: an aqueous biocide formulation containing methylisothiazolinone and chloromethylisothiazolinone.

Biocide 2: Glycol based biocidal formulation containing benzisothiazolinone. Biocide 3: biocidal formulation containing 2-bromo-2-nitropropane-1,3-diol.

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Xanthan gum.

Adjuvant 1: Methylated seed oil, alkylphenol ethoxylate.

Non-ionic surfactant 1: non-ionic surfactant containing tristyrylphenol alkoxylate.

Nonionic surfactant 2: PEO-PPO-PEO type nonionic surfactant, Mw of PPO is 3250 g/mol, the percentage of polyethylene glycol per molecule is 50 wt%.

Anionic surfactant A1-1: sodium lignosulfonate, see table. 1.

Anionic surfactant A1-2: sodium lignosulfonate, see table. 1.

Anionic surfactant A1-3: lignin, sulfomethylated, see table. 1.

Anionic surfactant A1-4: sodium lignosulfonate, see table. 1.

Anionic surfactant A1-5: sodium lignosulfonate, see table. 1.

Surfactant A2-1: 20% aqueous solution of sodium salt of poly(2-acrylamido-2-methylpropanesulfonic acid) with a pH value of 2.5-4; (CAS No. 55141-01-0 or 3564159-9).

Pre-condensate P1: 70% by weight aqueous solution of esterified pre-condensate of melamine and formaldehyde, CAS No. 68002-20-0.

Roundup® Powermax II Herbicide: A commercially available aqueous solution of glyphosate potassium containing 540 grams of glyphosate per liter (based on glyphosate acid).

Engenia® Herbicide: A commercially available aqueous solution of dicamba K,K,Bis-(3-aminopylamine)methylamine salt, containing 600 grams of glyphosate per liter (based on dicamba acid).

Roundup WeatherMAX Herbicide: A commercially available aqueous solution of glyphosate potassium containing 540 grams of glyphosate per liter (based on glyphosate acid).

Honcho® plus herbicide: a commercially available aqueous solution of isopropylammonium salt of glyphosate, containing 356 grams of glyphosate per liter (based on glyphosate acid).

III. Preparation of compositions in accordance with the invention:

a) Pre-prepared suspension mixture.

4.1 kg of saflufenacil tgai (Technical Grade of the Active Ingredient) (purity 97.5%) was ground in a bead mill in an aqueous phase containing 80 g of sodium lauryl sulfate, 8.0 g of Biocide 1, 16.0 g Biocide 2 and 6.4 g Biocide 3, respectively, 4.0 g Antifoam 1, 4.5 g citric acid and 3.78 kg water, until the particle size reaches a d50 value of 1.1 µm, in accordance with static laser scattering data. (Applicable hardware: Malvern 3000, software: V3.63, dispersion model: Fraunhofer model, analytical model: universal).

b) Pre-mixed capsules.

280 g of the above pre-prepared suspension mixture was mixed with 52 g of a 20% by weight solution of Surfactant A2-1, then 59 g of Precondensate P1 was added, and finally 32 g of a 10% by weight aqueous solution of citric acid. The specified pre-prepared mixture was heated to +80°C with stirring, kept at a temperature of +80°C for 2 hours, then cooled to room temperature. A suspension of microcapsules with a d50 value of 46 μm was obtained (Equipment used: Malvern 3000, software: V3.63, scattering model: Fraunhofer model, analytical model: universal).

c) Capsulated formulation.

To 10 g of the above premixed capsule mixture, 0.5 g of polymer surfactant was added according to the following table, and the suspension was equilibrated by stirring for 30 minutes. Five stabilized encapsulated formulations of CS1-CS5 were obtained.

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Table 1. Properties of anionic surfactants A1-1-A1-5

Example Dispersant Mw [g/mol] Degree of sulfonation [mol SO3/kg lignosulfonate] V compliance With invention / comparison CS1 Anionic surfactant A1-1 43,000 1.9 V compliance With invention CS2 Anionic surfactant A1-2 65,000 1.7 V compliance With invention CS3 Anionic surfactant A1-3 10 200 1.5 V compliance With invention CS4 Anionic surfactant A1-4 3 100 2.9 comparison CS5 Anionic surfactant A1-5 6 200 0.7 comparison

d) Miscibility tests.

To simulate tank mix preparation by a farm worker, 0.7 g of each of the above formulations CS1-CS5 was dispersed in 100 ml of CIPAC D standard water (CIPAC - International Cooperative Pesticide Analysis Council), then added 2.1 ml of Roundup Powermax II herbicide , shook and kept the mixture for 24 hours. After this, the liquid was poured onto a sieve with a mesh size of 150 µm and the residue remaining on the sieve was assessed visually.

Capsulated formulation Residues on the sieve Conclusion CS1 trace amounts mixable with glyphosate, suitable CS2 No mixable with glyphosate, suitable CS3 trace amounts mixable with glyphosate, suitable CS4 large balance immiscible with glyphosate, not suitable CS5 large balance immiscible with glyphosate, not suitable

e) Final confirmation of miscibility.

Capsulated formulation CS6.

To obtain the preparative form of saflufenacil CS6, 1.6 g of Biocide 2, 0.6 g of Biocide 3, 0.8 g of Biocide 1, 4.2 g of Antifoaming Agent 2 were added to 700 g of the pre-prepared capsule mixture described in point b). , 25 g Nonionic Surfactant 2, 50 g Anionic Surfactant A1-3, 2.5 g xanthan gum, 35 g ammonium acetate, 24 g 25% aqueous ammonia, and 260 g water.

The CS6 formulation was dispersed in 100 g of CIPAC D standard water and the test additives were added according to the table below, the aqueous suspensions were then allowed to stand for 2 hours and finally poured onto a 150 µm sieve. As in the previous example, the residue remaining on the sieve was assessed visually.

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Experience CS6 [g] Additive 1 [G] Additive 2 [G] Residue on sieve 1 0.7 Roundup Powermax II Herbicide 3.2 - - trace amounts 2 0.7 Roundup Powermax II Herbicide 3.2 Adjuvant 1 (NH4)2SO4 0.9 1.0 trace amounts 3 0.7 Herbicide Engenia 1.2 - - trace amounts 4 0.7 Herbicide Engenia 1.2 Adjuvant 1 (NH4)2SO4 0.9 1.0 No 5 1.0 Roundup WeatherMAX Herbicide 3.2 - - No 6 1.0 Roundup WeatherMAX Herbicide 3.2 Adjuvant 1 (NH4)2SO4 0.9 1.0 No 7 1.0 Herbicide Honcho plus 4.1 - - No 8 1.0 Herbicide Honcho plus 4.1 Adjuvant 1 (NH4)2SO4 0.9 1.0 No

e) Capsulated formulation of CS7.

To obtain the preparative form of saflufenacil CS7, 1.6 g of Biocide 2, 0.6 g of Biocide 3, 0.8 g of Biocide 1, 4.2 g of Antifoaming Agent 2 were added to 700 g of the pre-prepared capsule mixture described in point b). , 25 g Nonionic surfactant 1, 50 g Anionic surfactant A1-2, 2.5 g xanthan gum, 35 g ammonium acetate, 24 g 25% aqueous ammonia and 260 g water.

The CS7 formulation was dispersed in 100 g of CIPAC D standard water and the test additives were added according to the table below, the aqueous suspensions were then allowed to stand for 2 hours, and finally poured onto a 150 µm sieve. As in the previous example, the residue remaining on the sieve was assessed visually.______________________________

Experience CS7 [g] Additive 1 H Additive 2 [G] Residue on sieve 1 0.7 Roundup Herbicide Powermax II 3.2 - - No 2 0.7 Roundup Herbicide Powermax II 3.2 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts 3 0.7 Herbicide Engenia 1.2 - - trace amounts 4 0.7 Herbicide Engenia 1.2 Adjuvant 1 (NH4)2SO4 0.9 ι,ο No 5 1.0 Roundup WeatherMAX Herbicide 3.2 - - No 6 1.0 Roundup Herbicide 3.2 Adjuvant 1 0.9 No WeatherMAX (NH4)2SO4 ι,ο 7 1.0 Herbicide Honcho plus 4.1 - - trace amounts 8 1.0 Herbicide Honcho plus 4.1 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts

g) Capsulated formulation of CS8.

To obtain the preparative form of saflufenacil CS8, 1.6 g of Biocide 2, 0.6 g of Biocide 3, 0.8 g of Biocide 1, 4.2 g of Antifoaming Agent 2 were added to 700 g of the pre-prepared capsule mixture described in point b). , 25 g Nonionic Surfactant 2, 50 g Anionic Surfactant A1-1, 2.5 g xanthan gum, 35 g ammonium acetate, 24 g 25% aqueous ammonia and 260 g water.

The CS8 formulation was dispersed in 100 g of CIPAC D standard water and the test additives were added according to the table below, the aqueous suspensions were then allowed to stand for 2 hours and finally poured onto a 150 µm sieve. As in the previous example, the residue remaining on the sieve was assessed visually.

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Experience CS8 [g] Additive 1 H Additive 2 [G] Residue on sieve 1 0.7 Roundup Herbicide Powermax II 3.2 - - trace amounts 2 0.7 Roundup Herbicide Powermax II 3.2 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts 3 0.7 Herbicide Engenia 1.2 - - No 4 0.7 Herbicide Engenia 1.2 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts 5 1.0 Roundup WeatherMAX Herbicide 3.2 - - No 6 1.0 Roundup WeatherMAX Herbicide 3.2 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts 7 1.0 Herbicide Honcho plus 4.1 - - trace amounts 8 1.0 Herbicide Honcho plus 4.1 Adjuvant 1 (NH4)2SO4 0.9 ι,ο trace amounts

Claims (15)

1. A microparticle herbicidal composition containing saflufenacil, wherein saflufenacil is present in the form of microparticles that contain solid saflufenacil that is surrounded by or enclosed in an aminoplast polymer, wherein said aminoplast polymer is a polycondensation product of one or more amino compounds and one or more aldehydes, and additionally containing at least one lignin-based sulfonic acid A, wherein said lignosulfonic acid A has an average molar mass MW of at least 10,000 Da and a degree of sulfonation of from 1.0 to 2.5 moles per kilogram of said lignosulfonic acid A, and wherein the aminoplast polymer is selected from the group consisting of melamine-formaldehyde resins and urea-formaldehyde resins and mixtures thereof. 2. The composition according to claim 1, wherein said at least one lignin-based sulfonic acid A is selected from the group consisting of lignosulfonic acid and ethoxylated lignosulfonic acid. 3. The composition according to one of claims 1 or 2, further containing at least one anionic surfactant A2, wherein the anionic surfactant A2 is homo- or copolymers of monoethylenically unsaturated monomers Ml having a sulfonic acid group, optionally with one or several M2 comonomers that differ from the Ml monomers. 4. The composition according to one of claims 1 or 2, further containing an alkyl sulfate, such as lauryl sulfate. 5. Composition one by one from pi. 1-4, wherein the aminoplast polymer is a melamine-formaldehyde resin. 6. Composition one by one from pi. 1-5, where the amount of aminoplast polymer in the microparticle composition is from 0.5 to 40 wt.%, preferably from 1 to 35 wt.% and, in particular, from 5 to 25 wt.% based on the total weight of aminoplast polymer and saflufenacil . 7. Composition one by one from pi. 1-6, wherein the microparticles have a weighted average particle diameter d50 ranging from 1 to 25 μm, as determined by dynamic light scattering of an aqueous dispersion of the microcapsules. 8. Composition one by one from pi. 1-7, where the microparticles contain less than 10 wt.% particles that have a particle diameter of greater than 50 μm, as determined by dynamic light scattering of an aqueous dispersion of microcapsules. 9. Composition according to one of claims 1-8, which is an aqueous suspension of microparticles. 10. Composition one by one from pi. 1-8, which is a solid composition of microparticles. 11. Composition according to one of claims 1 to 10, which contains one or more auxiliary substances usually used for the formulation of plant protection compositions. 12. Method of obtaining a composition based on one of pi. 1-11, which includes the following stages: I) providing an aqueous suspension or dispersion of saflufenacil solid particles; ii) adding an aminoplast precondensate to the aqueous suspension, the aminoplast precondensate being selected from the group consisting of melamine-formaldehyde precondensates and urea-formaldehyde precondensates; III) carrying out the polycondensation of the aminoplast precondensate, which further includes the addition of lignosulfonic acid A having an average molar mass MW of at least 10,000 Da and a degree of sulfonation from 1.0 to 2.5 mol per kilogram, where the addition is carried out after step I) , after stage II) and/or after stage III). -22045461 13. The method of claim 12, wherein the saflufenacil particles in the aqueous suspension or dispersion have a weighted average particle diameter d50 ranging from 0.5 to 25 μm, as determined by dynamic light scattering. 14. Use of a composition of microparticles according to one of claims 1-11 to combat unwanted vegetation. 15. A method for controlling unwanted vegetation, comprising applying a microparticle composition according to one of claims 1 to 11 to plants, their environment and/or seeds and allowing the composition to act on said plants, their environment and/or seeds .