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WO2015091642A1 - Compositions aqueuses diluées de saflufénacil - Google Patents

Compositions aqueuses diluées de saflufénacil Download PDF

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Publication number
WO2015091642A1
WO2015091642A1 PCT/EP2014/078213 EP2014078213W WO2015091642A1 WO 2015091642 A1 WO2015091642 A1 WO 2015091642A1 EP 2014078213 W EP2014078213 W EP 2014078213W WO 2015091642 A1 WO2015091642 A1 WO 2015091642A1
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WO
WIPO (PCT)
Prior art keywords
composition
component
compound
poly
adjuvant
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Application number
PCT/EP2014/078213
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English (en)
Inventor
Gerhard Schnabel
Paul Klingelhoefer
Marc Nolte
Mariano Ignacio ETCHEVERRY
Matthias Bratz
Steven Bowe
Kyle Keller
Original Assignee
BASF Agro B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by BASF Agro B.V. filed Critical BASF Agro B.V.
Publication of WO2015091642A1 publication Critical patent/WO2015091642A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • 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.
  • saflufenacil 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.
  • saflufenacil is only sparingly soluble in water and the aqueous dilution may become instable.
  • the aqueous dilutions sometimes show fluctuations in herbicidal efficiency.
  • 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.
  • the adjuvants are not always compatible with the dilution and the stability of the dilution may be impaired by addition of the adjuvant.
  • 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.
  • a formulation of the co-herbicide is added as a tank mix to the aqueous dilution of saflufenacil.
  • 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.
  • 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.
  • compositions of the invention comprise the
  • 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);
  • component 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;
  • component c) as component c) at least one inorganic salt selected from carbonates,
  • 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.
  • saflufenacil in particular the anhydrate form thereof, remains stable against degradation, while the adjuvant does not impair stability of the dilution.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 2 ⁇ values, or as interplanar spacings d:
  • the dilute aqueous compositions of the present invention comprise at least one adjuvant as component b).
  • 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.
  • 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.
  • poly-C2-C4-alkylene ether group is understood by a skilled person as an aliphatic polyether radical which is composed of C2-C 4 -alkylene oxide repeating units, i.e. repeating units of the formula A-O, where A is C2-C 4 -alkylene, such as
  • the poly-C2-C 4 -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-C 4 -alkylene ether groups b1 ) include but are not limited to
  • 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.
  • 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-
  • 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.
  • 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;
  • the adjuvant comprises at last one compound b1 ).
  • 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).
  • 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.
  • 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.
  • the compound which is selected from C6-C2o-alkylamine poly-C2-C4-alkoxylat.es and C6-C2o-alkanol P0IV-C2-C4- alkoxylates.
  • the compound b1 comprises at least one C6-C2o-alkylamine poly-C2-C4-alkoxylate, in particular at least one
  • 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.
  • 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.
  • 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.
  • the adjuvant comprises at last one compound b2).
  • 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).
  • 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 ⁇ , ⁇ -dimethylamides of fatty acids, more particularly
  • fatty acids 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.
  • 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.
  • saturated carboxylic acids such as caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid or be
  • 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.
  • 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.
  • the adjuvant comprises at last one compound b1 ) and at least one compound b2).
  • 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).
  • the adjuvant component b) may comprise one ore more further organic compounds conventionally used in adjuvants, in particular
  • non-ionic surfactants different from component b1 e.g. alkylpolyglycosides or sorbitan fatty acid esters; and/or
  • hydrocarbons such as paraffin oil, liquid fatty acid triglycerides such as plant oils
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • the adjuvant comprises at least one water- immiscible component b2).
  • 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 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
  • 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.
  • 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).
  • 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.
  • 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
  • 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.
  • 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 ⁇ .
  • the particulate solid may comprise auxiliaries, conventionally used in solid
  • anticaking agents or separating agents 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.
  • 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.
  • the dilute aqueous composition of the invention may contain a co-herbicide, which is known to be suitable for co- application with saflufenacil.
  • 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.
  • chloroacetamides such as metolachlor, acet
  • 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.
  • the dilute aqueous composition comprises a water soluble salt of glyphosate, e.g. a sodium, sesquisodium, potassium,
  • 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.
  • 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.
  • 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.
  • 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 for crystallization, 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.
  • 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.
  • 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,
  • 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 are 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 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.
  • 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,
  • 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.
  • 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.
  • 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.
  • the components a), b) and c) and optionally e) or f) are added to water, which is also referred to as tank-mixing.
  • 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.
  • 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).
  • the water contains at least 0.1 mmol/l, or at least
  • 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.
  • 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:
  • 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.
  • 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.
  • 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.
  • crops plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • 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.
  • 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.
  • the aqueous compositions described herein are useful for combating undesired vegetation.
  • 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.
  • 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).
  • 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.
  • compositions of the invention 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.
  • plant protection agents for example with agents for controlling pests or phytopathogenic fungi or bacteria.
  • 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 pH values of the formulations were determined according to the test method of the Collaborative International Pesticides Analytical Council CIPAC MT 75.3.
  • 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 ⁇ , ⁇ -dimethyldecanoylamide and
  • Nonionic surfactant NS1 Castol il ethoxylate with 48 EO (Wettol® EM31 of BASF
  • Nonionic surfactant NS3 Cs-Cio-Alkylpolyglycoside (Agnique PG 8107-G, Cognis)
  • 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.
  • 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.
  • 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.
  • Table 3 relates to the herbicidal activity of saflufenacil assessed 21 days after treatment (DAT).
  • 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

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Abstract

La présente invention concerne de nouvelles compositions aqueuses diluées de 2-chloro-5-[3,6-dihydro-3-méthyl-2,6-dioxo-4-(trifluorométhyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[méthyl(1-méthyléthyl)amino]sulfonyl]benzamide, désigné également ci-après par son nom commun « saflufénacil ». L'invention concerne également l'utilisation des compositions pour lutter contre la végétation indésirable et des procédés correspondants. Les compositions aqueuses diluées de l'invention comprennent les composants suivants : a) du saflufénacil, c'est-à-dire du 2-chloro-5-[3,6-dihydro-3-méthyl-2,6-dioxo-4-(trifluorométhyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[méthyl(1-méthyléthyl)amino]sulfonyl]benzamide en tant que composant a) ; b) au moins un adjuvant en tant que composant b), le composant b) comprenant au moins un composé b1) ou b2) ou un mélange de b1) et b2), le composé b1) étant choisi parmi des composés possédant au moins un groupe poly-alkylène en C2 à C4 éther et le composé b2) étant choisi dans le groupe constitué d'esters alkyliques en C1 à C4 d'acides gras, des N-alkyle en C1 à C4-amides d'acides gras et des N,N-di-alkylamides en C1 à C4 d'acides gras ; c) en tant que composant c) au moins un sel inorganique choisi parmi les carbonates, bicarbonates, phosphates, monohydrogénophosphates et dihydrogénophosphates de sodium ou potassium et leurs mélanges ; d) de l'eau ; la composition contenant le sel inorganique en une quantité telle que la valeur de pH de la composition, déterminée à 20 °C, est dans la plage de plus de pH 5,5 à moins de pH 9, en particulier dans la plage de plus de pH 6 à pH 8,5.
PCT/EP2014/078213 2013-12-19 2014-12-17 Compositions aqueuses diluées de saflufénacil WO2015091642A1 (fr)

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US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10695734B2 (en) 2015-11-23 2020-06-30 Basf Se Microcapsule comprising a polyester-urethane shell and a hydrophilic core material
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
WO2021038439A1 (fr) * 2019-08-26 2021-03-04 Adama Agan Ltd. Nouvelles compositions liquides solubles de saflufénacil, son procédé de préparation et son utilisation
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11206827B2 (en) 2015-07-10 2021-12-28 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US11116213B2 (en) 2015-07-10 2021-09-14 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pethoxamid
US11206827B2 (en) 2015-07-10 2021-12-28 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific quinolinecarboxylic acids
US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
US11517018B2 (en) 2015-07-10 2022-12-06 BASF Agro B.V. Herbicidal composition comprising cinmethylin and saflufenacil
US11077417B2 (en) 2015-11-23 2021-08-03 Basf Se Microcapsule comprising a polyester-urethane shell and a hydrophobic core material
US10695734B2 (en) 2015-11-23 2020-06-30 Basf Se Microcapsule comprising a polyester-urethane shell and a hydrophilic core material
WO2021038439A1 (fr) * 2019-08-26 2021-03-04 Adama Agan Ltd. Nouvelles compositions liquides solubles de saflufénacil, son procédé de préparation et son utilisation
CN114727603A (zh) * 2019-08-26 2022-07-08 安道麦阿甘有限公司 新型的苯嘧磺草胺的可溶性液体组合物，其制备方法及用途

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