WO2015091642A1

WO2015091642A1 - Dilute aqueous compositions of saflufenacil

Info

Publication number: WO2015091642A1
Application number: PCT/EP2014/078213
Authority: WO
Inventors: Gerhard Schnabel; Paul Klingelhoefer; Marc Nolte; Mariano Ignacio ETCHEVERRY; Matthias Bratz; Steven Bowe; Kyle Keller
Original assignee: BASF Agro B.V.
Priority date: 2013-12-19
Filing date: 2014-12-17
Publication date: 2015-06-25
Also published as: AR098829A1

Abstract

The present invention relates to new dilute aqueous compositions of 2-chloro-5-[3,6dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, herein after also referred to with its common name "saflufenacil". The invention also relates to the use of the compositions for controlling undesired vegetation and to corresponding methods. The dilute aqueous compositions of the invention comprise the components: a) saflufenacil, i.e. 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 as component a); b) at least one adjuvant as component b), where component b) comprises at least one compound b1) or b2) or a mixture of b1) and b2), wherein compound b1) is selected from compounds having at least one poly-C₂-C₄-alkylene ether group and where compound b2) is selected from the group consisting of C₁-C₄-alkyl esters of fatty acids, N-C₁-C₄ -alkyl-amides of fatty acids and N,N-di-C₁-C₄-alkylamides of fatty acids; c) as component c) at least one inorganic salt selected from carbonates, hydrogencarbonates, phosphates, monohydrogenphosphates and dihydrogenphosphates of sodium or potassium and mixtures thereof; d) water; wherein the composition contains the inorganic salt in such an amount that the pH value of the composition, determined at 20°C, is in the range from above pH 5,5 to below pH 9, in particular in the range from above pH 6 to pH 8.5.

Description

Dilute aqueous compositions of saflufenacil Description

The present invention relates to new dilute aqueous compositions of 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, herein after also referred to with its common name "saflufenacil". The invention also relates to the use of the compositions for controlling undesired vegetation and to corresponding methods.

Saflufenacil is a herbicidal active substance from the group of PPO inhibitors having the following formula I,

Saflufenacil has been described in WO 01/083459. Further processes for its preparation are described in WO 03/097589, WO 05/054208, WO 06/097589 and WO 06/125746. Saflufenacil is particularly useful for preplant burndown and selective preemergence broadleaf weed control in multiple crops, including corn and soybean.

A crystalline and essentially solvent-free form of saflufenacil, herein after also referred to as the crystalline anhydrate form, is disclosed in WO 08/043835.

For the purpose of application by the end user, conventional formulations of saflufenacil, such as suspension concentrates and wettable powders, are diluted with water and these diluted compositions usually provide an easy-to-handle way of application. However, like many active ingredients that are used as herbicides, saflufenacil is only sparingly soluble in water and the aqueous dilution may become instable. Moreover, the aqueous dilutions sometimes show fluctuations in herbicidal efficiency. In order to increase the activity and selectivity of saflufenacil, it is principally known to co-apply saflufenacil with a suitable adjuvant. Suitable adjuvants include paraffin oils, methylated seed oils, mono- and diglycerids of fatty acid asters, polyalkoxylated fatty acids and polyoxylated fatty acid esters, polyalkoxylated alkanols and polyalkoxylated alkylamines as well as mixtures thereof. Such an adjuvant is normally added as a tank mix to the aqueous dilution of saflufenacil. However, the adjuvants are not always compatible with the dilution and the stability of the dilution may be impaired by addition of the adjuvant. In order to increase the activity and selectivity of saflufenacil, it is principally known to co-apply saflufenacil with a co-herbicide. Suitable co-herbicides have been described in WO 03/24221 and WO 2007/014759. A particular co-herbicide is glyphosate or a salt thereof. Usually, a formulation of the co-herbicide is added as a tank mix to the aqueous dilution of saflufenacil. However, the co-herbicide formulations are not always compatible with the dilution and the stability of the dilution may be impaired by the addition of the formulation of the co-herbicide.

WO 201 1/023759 describes an aqueous suspension concentrate of the crystalline anhydrate saflufenacil, which contains at least one non-ionic surfactant selected from ethylene oxide/C3-C4-alkylene oxide block copolymers and at least one an anionic surfactant from the group of arylsulfonate salts, which has an acidic pH, which is preferably in the range pH 4.5 to 5.5. Although, this formulation shows improved compatibility with adjuvants, the herbicidal activity is not always satisfactory. Moreover, the stability of the dilution may still be a problem.

It is therefore an object of the present invention to provide an aqueous dilution of saflufenacil, which overcomes the problems of prior art, and which in particular shows improved herbicidal activity and/or improved stability, in particular if it contains a co- herbicide, such as glyphosate, and/or and adjuvant.

It was surprisingly found that the dilute aqueous herbicide compositions of saflufenacil, as described herein and in the claims solve the above objects.

The dilute aqueous composition compositions of the invention comprise the

components: a) saflufenacil, i.e. 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 - (2H)pyrimidinyl]-4-fluoro-N-[[methyl(1 -methylethyl)amino]sulfonyl]benzam as component a);

b) at least one adjuvant as component b), where component b) comprises at least one compound b1 ) or b2) or a mixture of b1 ) and b2), wherein compound b1 ) is selected from compounds having at least one poly-C2-C4-alkylene ether group and where compound b2) is selected from the group consisting of Ci-C4-alkyl esters of fatty acids, N-Ci-C4-alkyl-amides of fatty acids and N,N-di-Ci-C4- alkylamides of fatty acids;

c) as component c) at least one inorganic salt selected from carbonates,

hydrogencarbonates, phosphates, monohydrogenphosphates and

dihydrogenphosphates of sodium or potassium and mixtures thereof;

d) water;

wherein the composition contains the inorganic salt in such an amount that the pH value of the composition, determined at 20°C, is in the range from above pH 5,5 to below pH 9, in particular in the range from above pH 6 to pH 8.5.

A pH value within the stated range in coaction with the components b) and c) unexpectedly improves herbicidal efficacy and imparts a good to excellent overall stability to the aqueous dilution both with regard to physical stability and chemical degradation of saflufenacil. In contrast to what has been taught in prior art and what a skilled person would expect, saflufenacil, in particular the anhydrate form thereof, remains stable against degradation, while the adjuvant does not impair stability of the dilution. Thus, by employing the combination of adjuvant b) and component c) and adjusting the pH value in the range given above it is surprisingly possible to balance the chemical stability of saflufenacil with the physical stability of the aqueous dilution and to improve herbicidal efficacy.

The present invention also relates to a method for preparing the aqueous dilute composition of the present invention. This method comprises mixing a conventional formulation of 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 with the at least one adjuvant of component b) and the at least one inorganic salt of component c) with water and optionally with further components of the aqueous dilute composition of the present invention. The present invention also relates to the use of the aqueous dilute composition of the present invention for controlling undesired vegetation. A dilute aqueous composition in terms of the present invention is understood as a composition which contains saflufenacil in such a concentration that it can be directly used for the desired purpose such as pre- or postemergence control, preplant burndown or desiccation/defoliation. Depending on the desired purpose, the concentration of saflufenacil will generally be in the range from 0.001 to 1 g/l, in particular from 0.01 to 0.8 g/l, especially from 0.015 to 0.7 g/l.

In the dilution of the present invention, saflufenacil may be present in an amorphous form or in one of its crystalline forms, e.g. in its hydrate forms or in the crystalline anhydrate form. Preferably, saflufenacil is at least partly present in the crystalline anhydrate form of saflufenacil. The crystalline anhydrate form of saflufenacil refers to the crystalline polymorph of saflufenacil that has been disclosed in WO 08/043835. Accordingly, the crystalline anhydrate form of saflufenacil is an essentially solvent-free crystalline form of saflufenacil. In this connection the term "essentially solvent-free" means that the crystalline anhydrate form comprises no detectable amounts of solvents incorporated into the crystal lattice, i.e. the amount of solvent in the crystal lattice is less than 10 mol%, in particular not more than 5 mol%, based on saflufenacil.

The anhydrate form of saflufenacil can be identified by means of X-ray powder diffractometry on the basis of its diffraction diagram. Thus, an X-ray powder diffractogram of the anhydrate form of saflufenacil, recorded at 25°C using Cu-K_a radiation (1.54178 A), shows at least 2, as a rule at least 4, frequently at least 6, in particular at least 8 and specifically all of the reflexes detailed in Table A hereinbelow as 2Θ values, or as interplanar spacings d:

Table A:

2Θ d [A ]

6.3 ± 0.2° 14.92 ± 0.3

9.4 ± 0.2° 9.37 ± 0.2

10.9 ± 0.2° 8.15 ± 0.1

1 1.9 ± 0.2° 7.45 ± 0.05

12.6 ± 0.2° 7.02 ± 0.05

15.0 ± 0.2° 5.90 ± 0.05 15.8 ± 0.2° 5.62 ± 0.04

17.1 ± 0.2° 5.19 ± 0.03

20.0 ± 0.2° 4.44 ± 0.02

20.4 ± 0.2° 4.36 ± 0.02

24.7 ± 0.2° 3.61 ± 0.02

25.2 ± 0.2° 3.53 ± 0.02

26.2 ± 0.2° 3.40 ± 0.02

The dilute aqueous compositions of the present invention comprise at least one adjuvant as component b). According to the invention, the adjuvant comprises at least one compound, which has at least one, e.g. 1 to 4, in particular 1 or 2 P0IV-C2-C4- alkylene ether groups. The concentration of the adjuvant b) in the compositions of the invention is generally in the range from 0.1 to 50 g/l, in particular from 0.2 to 20 g/l. The weight ratio of component a) to component b) is generally from 1 :10000 to 1 :1 and in particular from 1 :5000 to 1 :10. The concentration of the adjuvant as well as the relative amount of saflufenacil and adjuvant b) are calculated on the basis of the total weight of the non-aqueous constituents of the adjuvant.

The term "poly-C2-C4-alkylene ether group" is understood by a skilled person as an aliphatic polyether radical which is composed of C2-C₄-alkylene oxide repeating units, i.e. repeating units of the formula A-O, where A is C2-C₄-alkylene, such as

1 ,2-ethandiyl, 1 ,2-propandiyl, 1 ,2-butandiyl, 2,3-butandiyl, 1 -methyl-1 ,2-propandiyl or 1 ,4-butandiyl. Preferably, the poly-C2-C₄-alkylene ether group is composed of ethylene oxide and/or propylene oxide repeating units, i.e. A is 1 ,2-ethandily or 1 ,2-propanediyl.

Examples of compounds having one or more poly-C2-C₄-alkylene ether groups b1 ) include but are not limited to

poly-C2-C4-alkoxylat.es of aliphatic alcohols, in particular poly-C2-C4-alkoxylat.es of alkanols having 3 to 20 carbon atoms (=C3-C2o-alkanols), in particular 6 to 20 carbon atoms (C6-C2o-alkanols), in particular polyethoxylates and

polyethoxylates-co-propoxylates of linear or branched C3-C2o-alkanols, such as polyethoxylated or poly-ethoxy-co-propoxylated C6-C2o-fatty alcohols and poly- ethoxy-co-propoxylated C6-C2o-oxoalcohols. Examples of poly-C2-C4-alkoxylates of aliphatic alcohols are polyethoxylated lauryl alcohol, polyethoxylated isotridecanol, polyethoxylated cetyl alcohol, poly-ethoxylates-co-propoxylates of octanol, poly-ethoxylates-co-propoxylates of 2-ethyl-hexanol, poly-ethoxylates- co-propoxylates of heptanol, poly-ethoxylates-co-propoxylates of hexanol, poly- ethoxylates-co-propoxylates of 2-ethyl-propanol, poly-ethoxylates-co- propoxylates of butanol, poly-ethoxylates-co-propoxylates of iso-butanol, poly- ethoxylates-co-propoxylates of tert-butanol and poly-ethoxylates-co-propoxylates of propanol;

poly-C2-C4-alkoxylat.es, in particular polyethoxylates of polyol esters, wherein the polyols may be partially or completely esterified with saturated or unsaturated C6-C22-alkanoic acids, such as mono-, di- and triesters of glycerine and mono-, di-, tri-, tetra-, penta- and hexaesters of sorbitol. Examples of P0IV-C2-C4- alkoxylates of polyol esters are polyethoxylates of glycerine monostearate, polyethoxylates of sorbitol monooleat and polyethoxylates of sorbitol hexaoleat; poly-C2-C4-alkoxylat.es of aliphatic amines, in particular poly-C2-C4-alkoxylat.es of C6-C2o-alkylamines, especially polyethoxylates and polyethoxylate-co-propoxylate of C6-C2o-alkylamines, e.g. the polyethoxylates and polyethoxylate-co- propoxylates of 2-ethylhexylamine, the polyethoxylates and polyethoxylate-co- propoxylates of 2-propylheptylamine

poly-C2-C4-alkoxylates of fatty acids and hydroxyfatty acids, e.g. P0IV-C2-C4- alkoxylates of lauric acid, of palmitic, of oleic acid, of stearic acid, of rhizinoleic acid of 12-hydroxystearic acid or mixtures thereof;

- poly-C2-C4-alkoxylat.es of triglycerides containing hydroxyfatty acids such as rhicinoleic acid or 12-hydroxystearic acid, e.g. the poly-C2-C4-alkoxylat.es of castor oil.

Among the compounds b1 ), preference is given to those compounds, where in poly- C2-C4-alkylene ether groups the ethylene oxide units make up at least 50%, in particular at least 80% or all of the C2-C4-alkylene oxide repeating units of the poly- C2-C4-alkylene ether group.

Among the compounds b1 ), preference is given to those compounds, where in poly- C2-C4-alkylene ether groups the average number of the C2-C4-alkylene oxide repeating units in all of the poly-C2-C4-alkylene ether groups of the compound is within the range from 3 to 100, in particular from 3 to 50 and especially from 3 to 30. The average number of C2-C4-alkylene oxide repeating units is also termed degree of alkoxylation and relates to the average molar amount of C2-C4-alkylene oxide repeating units per one mole of the respective compound. In a preferred group of embodiments, the adjuvant comprises at last one compound b1 ). In this group of embodiments, the at least one compound b1 ) amounts to at least 30% of the adjuvant component b), e.g. from 30 to 100% of the adjuvant component b).

In this preferred group of embodiments, the compound b1 ) in particular comprises at least compound b1 ), which is selected from C6-C2o-alkylamine poly-C2-C4-alkoxylat.es, in particular the polyethoxylates and polyethoxylate-co-propoxylates of C6-C20- alkylamines and C6-C2o-alkanol poly-C2-C4-alkoxylat.es, in particular the polyethoxylates and polyethoxylate-co-propoxylates of C6-C2o-alkanols and mixtures thereof. In this preferred group of embodiments, the compound b1 ), which is selected from C6-C20- alkylamine poly-C2-C4-alkoxylat.es and C6-C2o-alkanol poly-C2-C4-alkoxylat.es amounts to at least 50% of the compounds having one or more poly-C2-C4-alkylene ether groups. In particular, in this preferred group of embodiments, the compound, which is selected from C6-C2o-alkylamine poly-C2-C4-alkoxylat.es and C6-C2o-alkanol P0IV-C2-C4- alkoxylates.

In a particular group of embodiments of the invention, the compound b1 ) comprises at least one C6-C2o-alkylamine poly-C2-C4-alkoxylate, in particular at least one

polyethoxylate or polyethoxylate-co-propoxylates of a C6-C2o-alkylamine, in particular polyethoxylate or polyethoxylate-co-propoxylates of a Cs-Cu alkylamine, which preferably has a degree of alkoxylation in the range from 3 to 30, especially in the range of 4 to 20. In a very particular group of embodiments of the invention, compound b1 ) comprises at least one polyethoxylate or polyethoxylate-co-propoxylate of a Cs-C-u alkylamine, e.g. of 2-propylheptylamine or of tallow amine, which preferably has a degree of alkoxylation in the range from 3 to 30, especially in the range of 4 to 20.

In a special group of embodiments of the invention, the compound b1 ) is selected from C6-C2o-alkylamine poly-C2-C4-alkoxylat.es, in particular from polyethoxylates or polyethoxylate-co-propoxylates of a C6-C2o-alkylamines, in particular from alkoxylated CS-CM alkylamines, which have a degree of alkoxylation in the range from 3 to 30, especially in the range of 4 to 20. In a very particular group of embodiments of the invention, compound b1 ) is selected from at least one polyethoxylate or polyethoxylate- co-propoxylate of a CS-CM alkylamine, e.g. of 2-propylheptylamine or of tallow amine, which preferably has a degree of alkoxylation in the range from 3 to 30, especially in the range of 4 to 20.

In a further preferred group of embodiments, the adjuvant comprises at last one compound b2). In this group of embodiments, the at least one compound b2) amounts to at least 30% of the adjuvant component b), e.g. from 30 to 100% of the adjuvant component b).

Suitable Ci-C4-alkyl esters of fatty acids include, in particular, the methyl or ethyl esters of fatty acids, in particular of fatty acids having 6 to 22 carbon atoms, especially of fatty acids having 12 to 20 carbon atoms. Suitable Ci-C4-alkyl esters of fatty acids also include, in particular, methylated or ethylated plant oils such as methylated rape seed oil, methylated soybean oil, ethylated rape seed oil or ethylated soybean oil. Suitable N-Ci-C4-alkyl- and N,N-di-Ci-C4-alkylamides of fatty acids, include N-methyl and N-ethyl amides of fatty acids and in particular Ν,Ν-dimethylamides of fatty acids, more particularly

The term "fatty acids" as used herein and in particular in context of component b2) refers to linear aliphatic carboxylic acids having from 6 to 22 carbon atoms, in particular from 12 to 20 carbon atoms, which are saturated or have 1 , 2 or 3 double bonds.

Examples of fatty acids include saturated carboxylic acids such as caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid or behenic acid, and mono- or polyunsaturated fatty acids, such as myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, linoelaidic acid, arachidonic acid or erucic acid, as well as mixtures of the aforementioned saturated fatty acids of different chain length, mixtures of the aforementioned unsaturated fatty acid acids and mixtures of the aforementioned saturated with one or more of the aforementioned unsaturated fatty acids.

In a particular group of embodiments of the invention, the compound b2) comprises at least one Ci-C4-alkylester of a fatty acid, in particular at least one methyl or ethylester of a fatty acid and especially at least one methylated plant oil. In a particular group of embodiments of the invention, the compound b2) is selected from at least one Ci-C4-alkylester of a fatty acid, in particular from at least one methyl or ethylester of a fatty acid and especially from at least one methylated plant oil. In a yet a further preferred group of embodiments, the adjuvant comprises at last one compound b1 ) and at least one compound b2). In this group of embodiments, the total amounts of compound b1 ) and b2) amounts to at least 30% of the adjuvant component b), e.g. from 30 to 100% of the adjuvant component b). Besides the compounds of groups b1 ) and b2), the adjuvant component b) may comprise one ore more further organic compounds conventionally used in adjuvants, in particular

b3) non-ionic surfactants different from component b1 ), e.g. alkylpolyglycosides or sorbitan fatty acid esters; and/or

b4) anionic surfactants

b5) water immiscible compounds different from compound b2), such as liquid

hydrocarbons such as paraffin oil, liquid fatty acid triglycerides such as plant oils

The term, water immiscible is clearly understood by a skilled person to mean that the miscibility with water is less than 1 g/l at 20°C, 1 bar and pH 7.

The term "liquid" is clearly understood by a skilled person to mean that the compound is liquid at ambient temperatures which generally means that it has a melting point below 25°C at normal pressure.

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of organic sulfonates, sulfates, phosphates, carboxylates, having at least one hydrocarbon radical, which has 6 to 22 carbon atoms, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of alkylphenols, of ethoxylated alkylphenols, of alkanols, of ethoxylated alkanols, or of fatty acid esters. Examples of phosphates are phosphate monoesters of alkylphenols, of ethoxylated alkylphenols, of alkanols, of ethoxylated alkanols. Examples of carboxylates are alkyl carboxylates, and carboxylated alkanols or alkylphenol ethoxylates. Generally, the total components b1 ) and b2), makes up from 30 to 100% by weight, in particular from 40 to 100% by weight, based on the total weight of the non-aqueous constituents of the adjuvant. In other words, the total amount of components b3) to b5) will generally not exceed 70% by weight, in particular 60% by weight of the total amount of component of the non-aqueous constituents of the adjuvant.

Generally, the total components b1 ) and b2), makes up from 80 to 100% by weight, in particular from 90 to 100% by weight, based on the total weight of the non-aqueous constituents of the adjuvant b), the remainder being preferably one or more of the components b3) to b4).

In particular group of embodiments, the adjuvant comprises at least one water- immiscible component b2). In this embodiment, the amount of component b2) is preferably in the range from 10 to 70% by weight, in particular from 20 to 60% by weight, based on the total weight of the non-aqueous constituents of the adjuvant. Consequently, the amount of component b1 ) and/or b3) to b5) is preferably in the range from 30 to 90% by weight, in particular form 40 to 80% by weight, based on the total weight of the non-aqueous constituents of the adjuvant.

The amount of component b3), if present, will generally not exceed 20% by weight, based on the total weight of the adjuvant, and, if present, is generally in the range from 1 to 20% by weight, based on the total weight of the non-aqueous constituents of the adjuvant.

The amount of component b4), if present, will generally not exceed 20% by weight, based on the total weight of the adjuvant, and, if present, is generally in the range from 1 to 20% by weight, based on the total weight of the non-aqueous constituents of the adjuvant.

The total amount of components b3) and b4) will generally not exceed 30% by weight, based on the total weight of the non-aqueous constituents of the adjuvant. In particular, the salt, which is used as component c) is a potassium salt, i.e. it is selected from potassium carbonate, potassium hydrogencarbonate, potassium phosphate, dipotassium monohydrogenphosphate and potassium

dihydrogenphosphate. The composition preferably comprises, as a component c) a salt, which is selected from hydrogencarbonates of sodium or potassium. More particularly, the inorganic salt of component c) is potassium hydrogen carbonate or a mixture thereof. The concentration of the component c) in the compositions of the invention is generally in the range from 0.1 to 50 g/l, in particular from 0.2 to 20 g/l. The weight ratio of component a) to component c) is generally from 1 :10000 to 1 :1 and in particular from 1 :5000 to 1 :10. The component c) may be formulated separately from the adjuvant b) or included into the adjuvant b).

If the component c) is formulated separately, it may be a solid formulation, e.g. a powder or granule formulation, or a liquid formulation, in particular an aqueous solution.

If component c) is formulated as a liquid, the liquid formulation will generally contain the component c) in a concentration of at least 20% by weight, preferably at least 30% by weight, and in particular at least 40% by weight and up to 70% by weight, based on the liquid formulation. The liquid formulation will usually contain at least at least 30% by weight, in particular at least 40% by weight of water, based on the liquid formulation. The amount of water in the liquid formulation of component c) may be up to 80% by weight, preferably up to 70% by weight, and in particular up to 60% by weight, based on the liquid formulation. The liquid formulation of component c) may additionally contain auxiliaries

conventionally used in liquid formulations, such as anti-freezing agents (e.g. glycerin), anti-foaming agents, (e.g. silicones), anti-drift agents, crystallization inhibitors (e.g. salts of polyacrylic acid) or binders. The liquid formulation of component c) may comprise up to 15% by weight, preferably up to 10% by weight, and in particular up to 5% by weight of auxiliaries, based on the liquid formulation. In another form the component c) is formulated as a particulate solid which preferably contains at least 50% by weight, preferably at least 80% by weight, and in particular at least 90% by weight of component c), based on the weight of the solid formulation. The particulate solid may have a particle size D90 of up to 10 mm, preferably up to 5 mm, and in particular up to 2 mm. The particle size may be determined by sieving. The particulate solid may contain less than 1 % by weight of dust. Dust means typically particles, which have a particle size of below 50 μηη. The particulate solid may comprise auxiliaries, conventionally used in solid

formulations, such as anticaking agents or separating agents. The amount of such auxiliaries may be up to 15% by weight, preferably not more than 10% by weight, and in particular not more than 5% by weight, based on the solid formulation. Suitable anticaking or separating agents are kaolinite, aluminum silicate, aluminum hydroxide, calcium carbonate, magnesium carbonate.

The aqueous dilute composition contains also water as a main constituent. The amount of water is generally above 95% by weight, in particular at least 97% by weight and especially at least 98% by weight, based on the total weight of the dilute composition. For example, the amount of water is from 97 to 99.99% by weight, in particular from 98 to 99.95% by weight, based on the total weight of the composition.

In addition to the aforementioned components a) to d), the dilute aqueous composition of the invention may contain a co-herbicide, which is known to be suitable for co- application with saflufenacil. Suitable co-herbicides for saflufenacil have been described in WO 03/24221 and WO 2007/014759, in particular in the examples of WO 03/24221 and WO 2007/014759, to which full reference is made.

Suitable co-herbicides are e.g. atrazine, chloroacetamides such as metolachlor, acetochlor, alachlor, dimethachlor, dimethenamide, metazachlor or pethoxamid, quinoline type carboxylic acid herbicides, such as quinchlorac or quinmerac, glyphosate, glufosinate, mesotrione, tembotrione, topramezone, isoxaflutole, pyroxasulfone, imidazolinone herbicides such as imazamox, impazapyr, imazapic, imazaquin, imazethapyr or imazamethabenz, dinitroaniline herbicides such as pendimethalin, benfluralin, prodiamin or trifluralin, dicamba, 2,4-D etc., and where applicable, the salts or esters thereof.

The concentration of the further herbicide compound, if present, will be generally in the range from 0.001 to 20 g/l, in particular from 0.01 to 10 g/l, depending on the activity of the further herbicide compound.

In a particular group of embodiments, the dilute aqueous composition comprises a water soluble salt of glyphosate, e.g. a sodium, sesquisodium, potassium,

monoammonium, diammonium, isopropylammonium, dimethylammonium or trimesium salt of glyphosate.

The aqueous dilute composition of the present invention may also contain one or more inorganic salts as a component f), which themselves no herbicidal activity and which are preferably a sodium, potassium or ammonium salt of a mineral acid, e.g. a salt selected from ammonium sulfate, potassium chloride, potassium sulfate and sodium sulphate and mixtures thereof. The inorganic salt may be incorporated in the formulation of saflufenacil, or in the formulation of the adjuvant or in the formulation of component c) or it may be separately formulated as a liquid or solid formulation, similar to the formulation described above.

If present, the concentration of the optional further component f) in the compositions of the invention is generally in the range from 0.1 to 50 g/l, in particular from 0.2 to 20 g/l. Apart from that, the aqueous dilute composition of the present invention may contain one or more further formulation auxiliaries or additives, which stem from the formulations of components a) to c) and optionally e) or f) used for preparing the aqueous dilution composition. Typical formulation auxiliaries are those, which are conventionally used for formulating herbicides.

They include solid or liquid carriers, which are different from water and from the aforementioned component b), as well as other formulation auxiliaries different from components b), c), e) and f), such as surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, compatibilizers, bactericides, anti-freezing agents,

crystallization inhibitors, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,

tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable crystallization inhibitors are polyacrylic acids and their salts, whereas the latter are preferred. The salts of polyacrylic acids may be ammonium, primary, secondary or tertiary ammonium derivatives, or alkali metal salts (e.g. sodium, potassium, lithium ions), wherein alkali metal salts such as sodium salts are preferred. The polyacrylic acids and their salts usually have a molecular weight (as determined by GPC, calibration with polystyrene sulphonates) of 1000 Da to 300 kDa, preferably of 1000 Da to 80 kDa, and in particular 1000 Da to 15 kDa. The crystallization inhibitors are usually water-soluble, e.g. at least 1 g/l, preferably at least 10 g/l, and in particular at least 100 g/l at 20°C. The tank mix usually contains from 0.0001 to 0.2 wt%, preferably from 0.005 to 0.05 wt% of the crystallization inhibitors (e.g. salts of polyacrylic acid). The tank mix adjuvant usually contains from 0.1 to 5.0 wt%, preferably from 0.25 to 2.5 wt% of the crystallization inhibitors (e.g. salts of polyacrylic acid).

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers such as urea; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, or protective colloid. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as

alkylisothiazolinones and benzisothiazolinones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Preferred anti-foaming agents are silicones, such as polydimethylsiloxan. Silicone based anti-foaming agents are commercially available, e.g. as KM 72 from Shin Etsu, SAG® 220 or SAG® 30 from Momentive, or Antifoam AF-30.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Suitable anti-drift agents are for example nonionic polymers (such as polyacrylamides, polyethylene glycols, or guar gum with a molecular weight of at least 20 kDa, preferably at least 50 kDa, and in particular at least 100 kDa. Such products are commercially available under the tradenames Guar DV27 from Rhodia, Companion® Gold, Border® EG, Direct®, Affect® GC. Further examples for anti-drift agents are oils, such as mineral oil, plant oils, methylated seed oil; lecithin; selfemulsifiably polyesters;

surfactants, such as those mentioned above. Such products are commercially available under the tradenames Termix® 5910, Wheather Guard Complete, Compadre®, Interlock®, Placement®, Silwett® L77, Hasten®, Premium® MSO, Transport® Plus, Point Blank® VM, Agridex®, Meth Oil®, Topcithin® UB, Topcithin® SB. Preferred auxiliaries are anti-freezing agents, crystallization inhibitors (e.g. salts of polyacrylic acid), and surfactants, as far as they do not belong to group b), such as alkylpolyglucosides and alkoxylates, e.g. amines, which have been alkoxylated. Preferably, the concentration of formulation auxiliaries, which are different from components a) to f) in the dilute composition of the invention does not exceed 2 g/l and is preferably below 1 g/l. In particular, the amount of formulation auxiliaries, which are different from components a) to f) does not exceed the amount of component b) contained in the aqueous dilute composition of the invention.

The aqueous dilute composition of the present invention is usually prepared by mixing a conventional formulation of 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 with the at least one adjuvant of component b) and the at least one inorganic salt of component c) or a formulation thereof, with water and optio with the components e) and/or f), if desired.

For this purpose, the components a), b) and c) and optionally e) or f) are added to water, which is also referred to as tank-mixing. As pointed out above, component b) and c) or components c) and f) or components a) and b) or components a), b) and e) or components a), b), c) and e) may be formulated together.

The water, which is used for tank-mixing, is usually untreated natural water, such as ground water, rain water collected in a water reservoir, river water, or lake water. The water, which is used for tank-mixing, may also be treated water such as tap water, which has passed a sewage plant. The water may be soft, medium or hard water. Frequently it is medium or hard water. Usually, the water has a hardness of at least 5°dH, or at least 10°dH, or at least 15°dH, or at least 20°dH (German degrees of hardness). In another form the water contains at least 0.1 mmol/l, or at least

1 .0 mmol/l, or at least 2.0 mmol/l, or preferably at least 3.0 mmol/l, or at least

3.5 mmol/l of the sum of calcium ions and magnesium ions.

As the dilute aqueous composition of the invention contains saflufenacil and optionally a coherbicide, it can be directly used for controlling undesired vegetation. It may also be used for dessication or defoliation of plants. The compositions of the invention affect a very good control of vegetation in non-crop areas, especially at high application rates. In crops such as soybean, cotton, oilseed rape, flax, lentils, rice, sugar beet, sunflower, tobacco and cereals, such as, for example maize or wheat, they are active against broad-leaved weeds and grass weeds without inflicting substantial damage to the crop plants. This effect is particularly observed at low application rates.

Depending on the application method in question, the compositions of the invention can additionally be employed in a further number of crop plants to remove undesired plants. Crops which are suitable are, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), 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, Pisum sativum, Prunus armeniaca, Prunus avium, Prunus cerasus, Prunus dulcis, Prunus domesticua, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. In addition, the compositions of the invention can also be used in crops which tolerate the effect of herbicides as the result of breeding, including genetic engineering methods.

Furthermore, the compositions of the invention can also be used in crops which tolerate attack by insects or fungi as the result of breeding, including genetic engineering methods.

Moreover, it has been found that the compositions of the invention are also suitable for the defoliation and desiccation of plant parts, for which crops plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. As desiccants, the compositions of the invention are particularly suitable for desiccating the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean. This makes possible the fully mechanical harvesting of these important crop plants. Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives or other species and varieties of pome fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton. Moreover, a shortening of the time interval within which the individual cotton plants mature leads to an increased fiber quality after harvesting.

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

In general, the aqueous compositions described herein are useful for combating undesired vegetation. For this purpose, the compositions may be applied as such. The aqueous compositions may also comprise further constituents in dissolved, emulsified or suspended form, for example fertilizers, active substances of other groups of herbicidal or growth-regulatory active substances, further active substances, for example active substances for controlling animal pests or phytopathogenic fungi or bacteria, furthermore mineral salts which are employed for alleviating nutritional and trace element deficiencies, and nonphytotoxic oils or oil concentrates.

The compositions of the invention can be applied by the pre-emergence or the post- emergence method. If saflufenacil and/or glyphosate are less well tolerated by certain crop plants, application techniques may be employed where the herbicidal

compositions are sprayed, with the aid of the spraying apparatus, in such a way that the leaves of the sensitive crop plants ideally do not come into contact with them, while the active substances reach the leaves of undesired plants which grow underneath, or the bare soil surface (post-directed, lay-by).

Depending on the aim of the control measures, the season, the target plants and the growth stage, the formulations of the invention are applied to such a degree that the application rates of saflufenacil are from 0.1 g to 100 g/ha, preferably from 10 to 100 g/ha active substance (a.s.). For burndown activity application rate will preferably be in the range from 10 to 60 g/ha, in particular from 15 to 50 g/ha and for achieving both burndown and residual activity application rates will preferably be in range from 20 to 100 g/ha, in particular form 30 to 70 g/ha.

Moreover, it may be useful to apply the compositions of the invention, separately or in combination with other herbicides, jointly as a mixture with yet further plant protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.

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

I. Analytics:

The pH values of the formulations were determined according to the test method of the Collaborative International Pesticides Analytical Council CIPAC MT 75.3.

Measurements were carried out as defined by CIPAC.

II. Used Materials

Amine ethoxylate AME1 Tallow amine ethoxylate with 10 EO

Amine ethoxylate AME2 Tallow amine ethoxylate with 5 EO

Amine ethoxylate AME3 2-Propylhepylamine ethoxylate with 10 EO

Amine ethoxylate AME4 2-Propylhepylamine ethoxylate with 5 EO

Alkanolalkoxylate AA: Ethoxylate-co-propoxylate of a Ci6/Ci8-alkanol having a total of 8 EO and 13 PO Anionic surfactant AS1 : C10-C13 linear alkyl benzene sulfonic acid

Anionic surfactant AS2: 60 % solution of the Ca salt of dodecylbenzene sulfonic acid in 2-ethylhexanol

Dimethylamid DAM: Mixture of Ν,Ν-dimethyldecanoylamide and

Ν,Ν-dimethyloctanoylamide (Hallcomide M 8-10 of Stepan

Company)

Nonionic surfactant NS1 Castol il ethoxylate with 48 EO (Wettol® EM31 of BASF

SE)

Nonionic surfactant NS2 Ethoxylate of isotridecanol with 8 EO;

Nonionic surfactant NS3 Cs-Cio-Alkylpolyglycoside (Agnique PG 8107-G, Cognis)

MSO: Methylated Seed Oil (Synative ES ME Ti 05, Cognis)

MO: Methyl oleate

TEOH: Triethanol amine

Potassium carbonate was used as a commercial liquid concentrate formulation containing about 50% of potassium carbonate (CLIMB® of Wilbur Ellis).

Saflufenacil was used as a commercial liquid suspension concentrate formulation containing about 34% by weight of saflufenacil (KIXOR ® of BASF SE).

The adjuvant compositions B1 to B12 summarized in tables 1 a and 1 b have been prepared by mixing the components in a suitable mixer.

Table 1 a: Adjuvant compositions B1 to B6:

Components B1 B2 B3 B4 B5 B6

[% bw] [% bw] [% bw] [% bw] [% bw] [% bw]

AME3 40 27 25 25 25 25

AS1 5 3 0 0 0 0

AA 25 30 0 0 0 0

AS2 0 0 10 3 10 3

NS1 0 0 0 7 0 7

DMA 0 0 15 15 25

MSO 0 0 50 50 40 40

MO 0 40 0 0 0 0

Water 30 0 0 0 0 0 Table 1 b: Adjuvant compositions B7 to B1 1 :

III. Preparation of the diluted compositions of the invention: General procedure:

A specified amount of the saflufenacil formulation, the adjuvant formulation and the potassium carbonate formulation were added to tab water resulting in the

concentrations and pH of the aqueous dilution given in table 2.

Table 2

Example Saflufenacil Adjuvant KHCOs K2CO3 pH

[g/350 I] Type [g/350 I] [g/350 I] [g/350 I]

V1 1 — 0 0 0 5

V2 2 — 0 0 0 5

V3 1 B12 1000 0 0 5

V4 2 B12 1000 0 0 5

1 1 B12 1000 250 0 8

2 2 B12 1000 250 0 8

3 1 B12 1000 500 0 8

4 2 B12 1000 500 0 8

V5 1 B12 1000 250 250 10

V6 1 B12 1000 500 500 10-1 1 IV. Herbicidal activity

The herbicidal activity of the aqueous dilutions according to the invention against various undesirable plants was demonstrated by the following pre- or post-emergence treatment field trials.

The test plants listed below were first grown, depending on the plant habit, to a height of 3 to 20 cm. The application rate was 350 l/ha, i.e. Application rates in g/ha of saflufenacil and adjuvant correspond to the values given in table 2. The test plants were sprayed using finely distributing nozzles.

The test period extended over 21 days. During this time, the plants were tended, and their response to the treatments with active compound was evaluated. The evaluation for the damage caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plants.

The plants used in the field trials belonged to the following species:

Table 3 relates to the herbicidal activity of saflufenacil assessed 21 days after treatment (DAT).

Table 3

Example Saflufenacil pH Herbicidal Activity (%)

[g/ioo I]

POLCO AMARE ERICA GERDI

V1 1 5 15 25 20 8

V2 2 5 25 33 18 8

V3 1 5 75 55 100 13

V4 2 5 83 70 100 35

1 1 8 — 60 — 35

2 2 8 88 83 100 45 Example Saflufenacil pH Herbicidal Activity (%)

[g/ioo I]

3 1 8 — 63 100 35

4 2 8 95 88 100 50

V5 1 10 48 45 68 8

V6 1 10-1 1 43 48 68 20

As can be seen from table 3 the compositions according to the invention, which contain potassium hydrogen carbonate and have a pH in the range of above pH 5.5 to pH 9 show higher herbicidal activities against a variety of weed targets than the

compositions containing no potassium hydrogen carbonate or potassium carbonate and having a pH below pH 5.5 or than compositions containing potassium hydrogen carbonate and potassium carbonate and having a pH above pH 9.

Claims

Claims:

An dilute aqueous herbicide composition, comprising the components:

a) 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 as component a);

b) at least one adjuvant as component b), where component b) comprises at least one compound b1 ) or b2) or a mixture of b1 ) and b2), wherein compound b1 ) is selected from compounds having at least one poly-C2-C₄- alkylene ether group and where compound b2) is selected from the group consisting of Ci-C₄-alkyl esters of fatty acids, N-Ci-C₄-alkyl-amides of fatty acids and N,N-di-Ci-C₄-alkylamides of fatty acids;

c) as component c) at least one inorganic salt selected from carbonates, hydrogencarbonates, phosphates, monohydrogenphosphates and dihydrogenphosphates of sodium or potassium and mixtures thereof; d) water;

wherein the composition contains the inorganic salt in such an amount that the pH value of the composition, determined at 20°C, is in the range of > pH 5.5 to pH 9.

The composition of claim 1 , wherein the pH value is in the range of > pH 6 to pH 8.

5.

The composition of any one of claims 1 or 2, wherein the inorganic salt is a potassium salt.

The composition of claim 3, where the inorganic salt is potassium hydrogen carbonate.

The composition of any one of the preceding claims, wherein the compound b1 ) having at least one poly-C2-C₄-alkylene ether group comprises a compound which is selected from C6-C2o-alkylamine poly-C2-C4-alkoxylat.es and C6-C20- alkanol poly-C2-C4-alkoxylat.es.

6. The composition of any one of the preceding claims, where in the compound b1 ) the ethylene oxide units make up at least 50 % of the C2-C4-alkylene oxide units of the poly-C2-C4-alkylene ether group.

7. The composition of any one of the preceding claims, wherein the adjuvant comprises a compound b2) selected from Ci-C₄-a Iky I esters of fatty acids, in particular from methylated plant oils.

The composition of any one of the preceding claims, wherein the compound b1 make up from 30 to 100% of component b).

The composition of any one of claims 1 to 7, wherein the compound b2) make up from 30 to 100% of component b).

The composition of any one of the preceding claims comprising:

component a) in a concentration from 0.001 to 1 g/l;

component b) in a concentration from 0.1 to 50 g/l;

component c) in a concentration from 0.1 to 50 g/l;

from 90 to 99.99% by weight, based on the total weight of the formulation, of water.

1 1 . The composition of any one of the preceding claims comprising at least one

further herbicidally active compound as a component e).

12. The composition of claim 1 1 , where the further herbicidally active compound is a water soluble salt of glyphosate.

13. The composition of claim 10 or 1 1 , where the concentration of the further

herbicide compound is from 0.001 to 20 g/l.

A method for preparing the composition of any one of the preceding claims which comprises mixing a conventional formulation of 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 with the at least one adjuvant of component b) and the at least one inorganic salt of component c) with water.

15. The use of the composition of any one of claims 1 to 13 for controlling undesired vegetation.

16. A method of controlling undesired vegetation, which comprises directly applying the composition of any one of claims 1 to 13 to plants, their environment and/or seeds.