WO2015197392A1 - Compositions herbicides comprenant de la cornexistine et/ou de l'hydroxycornexistine - Google Patents

Compositions herbicides comprenant de la cornexistine et/ou de l'hydroxycornexistine Download PDF

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WO2015197392A1
WO2015197392A1 PCT/EP2015/063268 EP2015063268W WO2015197392A1 WO 2015197392 A1 WO2015197392 A1 WO 2015197392A1 EP 2015063268 W EP2015063268 W EP 2015063268W WO 2015197392 A1 WO2015197392 A1 WO 2015197392A1
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composition
surfactant
esters
acid
surfactants
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PCT/EP2015/063268
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Ulrich Steinbrenner
Ruediger Reingruber
Florian Vogt
Anja Simon
Johannes Hutzler
Klaus Kreuz
Thomas Seitz
Richard Roger Evans
Hans-Christian Raths
Björn Thomas HAHN
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Basf Se
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    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids

Definitions

  • compositions comprising cornexistin and/or hydroxycornexistin
  • the present invention relates to compositions and agrochemical compositions comprising cornexistin and/or hydroxycornexistin.
  • the invention also relates to a process for preparation thereof and to the use of these compositions for controlling undesired vegetation as well as to corresponding methods.
  • an herbicide shall have a good compatibility with crops, high efficacy and reliability of action. Also desirable is a broad spectrum of activity of such an herbicide allowing the simultaneous control of multiple unwanted plants. Therefore, it is always desirable to improve at least one or even more of the above characteristics of herbicides.
  • Cornexistin (I.a1 ) and its corresponding dibasic acid (I.a2) are known from EP-A 0 290 193.
  • compositions that show enhanced herbicidal activity against unwanted plants.
  • the compositions should have good compatibility with useful plants.
  • the compositions should have a broad spectrum of activity.
  • a further object of the present invention is reducing the application rates of active ingredients.
  • the present invention provides for a herbicidal composition
  • a herbicidal composition comprising: A) a compound of formula I (herbicide A)
  • R 1 is CH 3 or CH 2 OH
  • R 2 and R 3 together with the neighboring carbon atoms form a dihydro-2,5-dioxofuran ring or
  • compositions according to the present invention demonstrate a better herbicidal activity against unwanted plants than would have been expected by the herbicidal activity of the active compounds alone. In other words, the herbicidal activity of the herbicides A) is increased when they are used together with the surfactants according to the present invention.
  • compositions of the invention show very good herbicidal activity, in particular at low application rates of active compounds, against a broad spectrum of weeds that have high economic impact. Further, compositions of the present invention demonstrate very good compatibility with useful plants, i.e. their use in crops does not result in increased damage when compared to the application of the individual components or mixtures thereof.
  • compositions according to the present invention are suitable as herbicides as such or as appropriately formulated compositions (agrochemical compositions).
  • agrochemical composition refers to a composition according to the present invention additionally comprising at least one inert liquid and/or solid carrier and, if appropriate, at least one auxiliary customary for agrochemical formulations.
  • the present invention also provides for agrochemical compositions comprising a herbicidally active amount of a composition according to the present invention and at least one inert liquid and/or solid carrier and, if appropriate, at least one auxiliary customary for herbicidal formulations.
  • the present invention further provides for ready to use herbicidal formulations obtainable by diluting compositions according to the present invention or agrochemical compositions according to the present invention with water.
  • compositions and agrochemical compositions according to the present invention for controlling undesired vegetation falls within this invention.
  • the invention provides for a process for preparation of the composition or the agrochemical composition according to the present invention, which comprises the steps of mixing the individual components of the composition, if appropriate, with agitation and/or heating.
  • the invention provides for a method for controlling undesirable vegetation, which method comprises allowing a herbicidally active amount of the composition or an agrochemical composition according to the present invention to act on plants, their environment or on seed.
  • cornexistin means the compound of formula (I.a1 ) as well as agriculturally acceptable salts thereof.
  • dibasic acid of cornexistin means the compound of formula (I.a2) as well as agriculturally acceptable salts thereof.
  • hydroxycornexistin means the compound of formula (I.a3) as well as agriculturally acceptable salts thereof.
  • dibasic acid of hydroxycornexistin means the compound of formula (I.a4) as well as agriculturally acceptable salts thereof.
  • the compounds of formulae (I.a1 ) to (I.a4) as described herein are capable of forming geometrical isomers, for example E/Z isomers. Accordingly, the terms "cornexistin”, “dibasic acid of cornexistin”, “hydroxycornexistin” and “dibasic acid of hydroxycornexistin” also encompass the pure E or Z isomers and mixtures thereof.
  • safeners means organic active compounds, some of which may also have herbicidal activity, which reduce or even prevent damage to the crop plants by herbicides.
  • the term "agriculturally acceptable salts” means the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of an active compound.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkali earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • esters means, for example, allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), methyl (1 -methylheptyl), heptyl, octyl or isooctyl (2- ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • hydrocarbon chains can be straight-chain or branched, the prefix C n -C m is denoting in each case the possible number of carbon atoms in the group.
  • poly(C2-Ce)alkoxylates refers to polyether moieties derived from ethyleneoxide (EO), propyleneoxide (PO), butyleneoxide (BO), pentylene oxide (PO), hexylene oxide (HO) or any mixtures thereof.
  • poly(C2-C4)alkoxylates refers to polyether moieties derived from ethyleneoxide, propyleneoxide, butyleneoxide or any mixtures thereof.
  • polyethoxylate refers to a polyether radical derived from ethyleneoxide.
  • polyalkoxylates also includes mixed polyether derived from at least two different alkylene oxides, e.g. polyethoxylates-co- propoxylates derived from a mixture of EO and PO.
  • the number of repeating units in the polyether moieties will preferably vary from 2 to 50, more preferably from 2 to 30, most preferably from 2 to 20.
  • composition of the present invention comprises a compound of formula I (herbicide A) as defined herein above.
  • Herbicide A is preferably selected from: a1 ) cornexistin (I.a1 ),
  • composition of the present invention further comprises a surfactant B selected from anionic and/or non-ionic surfactants having an unsubstituted OH group of an acid and/or alcohol function, preferably an unsubstituted anionizable OH group of an acid and/or alcohol function, more preferably an unsubstituted anionizable OH group of an acid and/or alcohol function that upon dilution (1 -10%) in water do not ionize completely, i.e. less than 99.9%, preferably less than 99%, more preferably less than 90%. From the aforementioned surfactants anionic surfactants are most preferred, anionic surfactants having an unsubstituted OH group of an acid function are particularly preferred.
  • anionizable OH group refers to an OH group of an acid and/or alcohol function that in aqueous solutions is able to donate a proton to water setting up equilibrium:— OH + H 2 0 3 ⁇ 4— O " + H 3 0 + .
  • At least 30% by weight, more preferably at least 50% by weight, most preferably at least 75% by weight and particularly preferred at least 85% by weight of the surfactant B according to the present invention are present in non-ionized (protonated) form in the formulation.
  • the surfactant B according to the present invention preferably has pKa in water at 25°C in the range from 0 to 12, more preferably in the range from 0 to 8, most preferably in the range from 0 to 5, and particularly preferably in the range from 0.5 to 4.
  • pKa can be determined, for example, by titration at 25 ⁇ 1 °C with 0.1 M sodium hydroxide using a METROHM 726 Titroprocessor (see Langmuir, 2003, 19, 2034-2038).
  • the surfactant B according to the present invention is selected from anionic surfactants having an unsubstituted OH group of an acid function, preferably an unsubstituted anionizable OH group of an acid function, more preferably an unsubstituted anionizable OH group of an acid function that upon dilution (1 -10%) in water do not ionize completely, i.e. less than 99.9%, preferably less than 99%, more preferably less than 90%.
  • Anionic surfactants B according to the present invention preferably have pKa in water at 25°C in the range from 0 to 5, more preferably in the range from 0.25 to 4.5, most preferably in the range from 0.5 to 4.
  • Preferred anionic surfactants B according to the present invention are phosphate esters, in particular mono-phosphate esters, di-phosphate esters, any mixtures of mono-phosphate esters and di-phosphate esters, carboxylated surfactants, as well as any mixtures thereof. More preferred anionic surfactants B according to the present invention are phosphate esters, in particular mono-phosphate esters, di-phosphate esters, and any mixtures thereof.
  • Examples of preferred anionic surfactants B according to the present invention are:
  • polycarboxylated polyoxyethylenes in particular homo- and copolymers of monoethylenically unsaturated mono- or dicarboxylic acids having from 3 to 8 carbon atoms, and the copolmyers also having polyethylene oxide side chains.
  • anionic surfactants B are the aforementioned anionic surfactants comprising at least one poly(C2-C6)alkoxylate moiety.
  • Examples of particularly preferred anionic surfactants B according to the present invention are:
  • Suitable salts of anionic surfactants B according to the present invention are alkaline metal salts, earth alkaline metal salts, zinc salts and/or ammonium salts, preferably alkaline metal salts, most preferably sodium and potassium salts.
  • the surfactant B according to the present invention is selected from non-ionic surfactants having an unsubstituted OH group of an alcohol function, preferably an unsubstituted anionizable OH group of an alcohol function, more preferably an unsubstituted anionizable OH group of an alcohol function that upon dilution (1 -10%) in water do not ionize completely, i.e. less than 99.9%, preferably less than 99%, more preferably less than 90%.
  • Preferable non-ionic surfactants B are alkoxylated fats or oils of animal or vegetable origin such as maize oil ethoxylates, castor oil ethoxylates, tallow fat ethoxylates, glycerol esters such as glycerol monostearate, fatty alcohol alkoxylates and oxoalcohol alkoxylates, fatty acid alkoxylates such as oleic acid ethoxylate, alkylphenyl alkoxylates such as isononyl-, isooctyl-, tributyl- and tristearylphenyl ethoxylates, fatty amine alkoxylates, fatty acid amide alkoxylates, sugar emulsifiers such as sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkylpolyglycosides,
  • Examples of preferred non-ionic surfactants B according to the present invention are:
  • Ci-Ci6-alkylaryl alkohols in particular polyethoxylates of C1-C16- alkylphenols, such as polyethoxylates of nonylphenol, decylphenol, isodecylphenol, dodecylphenol or isotridecylphenol,
  • - polyethoxylates of fatty acids and polyethoxylates of hydroxyl fatty acids - partial esters of polyols with C3-C22-alkanoic acids, in particular mono- and diesters of glycerine and mono-, di- and triesters of sorbitan, such as glycerine monostearate, sorbitanmonooleat, sorbitantristearat; and triglyceride polyalkoxylates;
  • polyethoxylates of mono- and diesters of glycerine and polyethoxylates of mono-, di- and triesters of sorbitan such as polyethoxylates of glycerine monostearate, polyethoxylates of sorbitanmonooleat, polyethoxylates of sorbitanmonostearat and polyethoxylates of sorbitantristearat;
  • polyethoxylates of vegetable oils such as soya oil, rapeseed oil, corn oil, sunflower oil, cotton seed oil, linseed oil, coconut oil, palm oil, safflower oil, walnut oil, peanut oil, olive oil or castor oil or animal fats, such as lard, tallow, milkfat, cod liver oil and whale oil; preferred are polyethoxylated vegetable oils; and
  • non-ionic surfactants B are the aforementioned non-ionic surfactants comprising at least one poly(C2-C6)alkoxylate moiety.
  • non-ionic surfactants B examples of most preferred non-ionic surfactants B according to the present invention are:
  • C4-Ci6-alkylphenols such as polyethoxylates of nonylphenol, decylphenol, isodecylphenol, dodecylphenol or isotridecylphenol,
  • polyethoxylates of vegetable oils such as soya oil, rapeseed oil, corn oil, sunflower oil, cotton seed oil, linseed oil, coconut oil, palm oil, safflower oil, walnut oil, peanut oil, olive oil or castor oil or animal fats, such as lard, tallow, milkfat, cod liver oil and whale oil; preferred are polyethoxylated vegetable oils.
  • Examples of particularly preferred non-ionic surfactants B according to the present invention are:
  • C6-Ci6-alkyl phenols such as polyethoxylates of nonylphenol, decylphenol, isodecylphenol, dodecylphenol or isotridecylphenol.
  • compositions according to the present invention comprising a non- ionic surfactants B as defined above additionally comprise an acid.
  • the acid is preferably selected from sulfuric, phosphoric, nitric, and/or carboxylic acids like e.g. formic, acetic, citric, propionic, glycolic, oxalic, tartaric, malic, maleic, fumaric acid. More preferred is phosphoric acid.
  • the surfactant B according to the present invention preferably has at least one mole of (C3- Ce)alkoxylate units per molecule, more preferably at least one mole of (C3-C4)alkoxylate units per molecule.
  • the surfactant B according to the present invention preferably has 2 to 15 ethoxylate units per molecule, more preferably 2 to 12 ethoxylate units per molecule, most preferably 2 to 10 ethoxylate units per molecule, particularly preferable 2 to 7 ethoxylate units per molecule.
  • the surfactant B according to the present invention has at least one mole of (C3-Ce)alkoxylate units per molecule, preferably at least one mole of (C3-C4)alkoxylate units per molecule and 2 to 15 ethoxylate units per molecule, more preferably 2 to 12 ethoxylate units per molecule, most preferably 2 to 10 ethoxylate units per molecule, particularly preferable 2 to 7 ethoxylate units per molecule.
  • the composition according to the present invention comprises at least one, preferably exactly one surfactant B.
  • composition according to the present invention comprises at least two, preferably two surfactants B different form each other.
  • anionic and non-ionic surfactants are known compounds or can be prepared by customary methods with which a skilled person is familiar and in apparatuses conventionally used for this purpose.
  • Particular examples of the aforementioned surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • the alcohol moieties of the surfactants B according to the present invention are obtainable both from natural sources, for example by obtaining and, if required or desired, by hydrolyzing, transesterifying, and/or hydrogenating glycerides and fatty acids, and by synthetic routes, for example by building up from starting materials having a smaller number of carbon atoms.
  • the SHOP process Shell Higher Olefin Process gives, starting from ethene, olefin fractions having a number of carbon atoms suitable for further processing to produce
  • the functionalization of the olefins to form the corresponding alcohols is carried out, for example, by hydroformylation and hydrogenation.
  • Olefins having a number of carbon atoms suitable for further processing to give suitable alcohols can also be obtained by oligomerization of C3-C6-alkenes, in particular propene, butene or mixtures of these.
  • lower olefins can be oligomerized by means of heterogeneous, acidic catalysts, e.g. supported phosphoric acid, and subsequently functionalized to give alcohols.
  • a general possibility of synthesizing to produce branched alcohols is, for example, the reaction of aldehydes or ketones with Grignard reagents (Grignard synthesis). Instead of Grignard reagents, it is also possible to employ aryllithium or alkyllithium compounds, which are distinguished by higher reactivity.
  • branched alcohols can be obtained by the Guerbet reaction, the skilled worker being familiar with the reaction conditions.
  • alkoxylation is the result of the reaction with suitable alkylene oxides which, as a rule, have 2 to 6, preferably 2 to 4, carbon atoms.
  • suitable alkylene oxides which, as a rule, have 2 to 6, preferably 2 to 4, carbon atoms.
  • the respective degree of alkoxylation is a function of the amounts of alkylene oxide(s) chosen for the reaction. It is, as a rule, a statistic mean since the number of alkylene oxide units of the alcohol alkoxylates resulting from the reaction varies.
  • the alcohols are reacted with the alkylene oxide(s) by customary methods with which the skilled worker is familiar and in apparatuses conventionally used for this purpose.
  • the alkoxylation may be catalyzed by strong bases such as alkali metal hydroxides and alkaline earth metal hydroxides, Bronsted acids or Lewis acids, such as AlC , BF3 and the like. Catalysts such as hydrotalcite or DMC (double metal cyanides) may be used for alcohol alkoxylates with a narrow distribution.
  • the alkoxylation is preferably carried out at temperatures in the range of from approximately 80 to 200°C, preferably approximately 100 to 180°C.
  • the pressure range is preferably between atmospheric pressure and 10 bar.
  • the alkylene oxide may comprise an admixture of inert gas, for example of from approximately 5 to 60%.
  • Alkyl phosphates and alkyl ether phosphates are made by treating alcohols or alcohol alkoxylate with a phosphorylating agent, e.g. di-, meta- or poly-phosphoric acids, PC or P4O4, preferred are phosphorus pentoxide P 4 Oio or polyphosphoric acid.
  • a phosphorylating agent e.g. di-, meta- or poly-phosphoric acids, PC or P4O4
  • P 4O4O4 preferred are phosphorus pentoxide P 4 Oio or polyphosphoric acid.
  • the reaction yields a mixture of mono- and di-esters of phosphoric acid which can be separated, if necessary.
  • the ratio between the two esters is determined by the ratio of the reactants.
  • composition of the present invention contains
  • composition of the present invention can also comprise an acid.
  • the acid is preferably selected from sulfuric, phosphoric, nitric, and/or carboxylic acids like e.g.
  • composition of the present invention can also comprise an agriculturally acceptable oil.
  • oils are paraffin oil, mineral oil, plant oil, aromatic oil, methyl oleate or fatty acid dialkylamides, more preferred oils are methyl oleate or fatty acid dialkylamides.
  • the oil preferably has a weight average number of carbon atoms between 12 and 25, preferably 14 to 20.
  • compositions of the invention can be mixed with a large number of further herbicidal or growth-regulatory active substances or applied together with these.
  • herbicides and plant growth regulators suitable for the compositions according to the present invention are lipid biosynthesis inhibitors:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicos
  • thifensulfuron thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron,
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,
  • penoxsulam pyrimisulfan and pyroxsulam
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8),
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; from the group of the photosynthesis inhibitors:
  • inhibitors of the photosystem II e.g. triazine herbicides, including of
  • chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin
  • aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham,
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone,
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone and bicyclopyrone, bleacher, unknown target: aclonifen, amitrole and flumeturon; from the group of the EPSP synthase inhibitors:
  • glyphosate glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate); from the group of the glutamine synthase inhibitors:
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium; from the group of the DHP synthase inhibitors:
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: chlorpropham, propham and carbetamide; from the group of the VLCFA inhibitors:
  • chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone,
  • 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters,
  • aminocyclopyrachlor and its salts and esters aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, qui
  • Preferred herbicides and plant growth regulators suitable for compositions according to the present invention are from the group of the lipid biosynthesis inhibitors:
  • ACC-herbicides such as clethodim, clodinafop, clodinafop-propargyl, cycloxydim, pinoxaden, and sethoxydim; and non ACC herbicides such as butylate, ethofumesate, flupropanate, molinate, thiobencarb, and vernolate; from the group of the ALS inhibitors:
  • sulfonylureas such as metsulfuron, metsulfuron-methyl, nicosulfuron, and tritosulfuron;
  • imidazolinones such as imazamox, imazapic, imazapyr, imazaquin and imazethapyr;
  • triazolopyrimidine herbicides and sulfonamides such as florasulam, metosulam, penoxsulam, and pyroxsulam; pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, and pyriftalid; sulfonylaminocarbonyl-triazolinone herbicides such as thiencarbazone and thiencarbazone-methyl; - from the group of the photosynthesis inhibitors:
  • amicarbazone inhibitors of the photosystem II, pyridazinones such as atrazine, cyanazine, metribuzin, prometryn, simazine, and terbuthylazin; aryl urea such as diuron, and linuron;
  • phenyl carbamates such as desmedipham; nitrile herbicides such as bromoxynil and its salts and esters; uraciles such as bromacil; and bentazon, bentazon-sodium, pyridate, and propanil and inhibitors of the photosystem I such as paraquat, paraquat-dichloride and paraquat- dimetilsulfate; from the group of the protoporphyrinogen-IX oxidase inhibitors:
  • PDS inhibitors diflufenican, norflurazon and picolinafen
  • HPPD inhibitors benzobicyclon, clomazone, isoxaflutole, mesotrione, sulcotrione, tembotrione, topramezone and bicyclopyrone
  • EPSP synthase inhibitors from the group of the EPSP synthase inhibitors:
  • glyphosate glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate); from the group of the glutamine synthase inhibitors:
  • bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium; - from the group of the mitosis inhibitors:
  • compounds of group K1 dinitroanilines such as pendimethalin, and trifluralin; phosphor- amidates such as butamiphos; pyridines such as dithiopyr; benzamides such as tebutam; compounds of group K2: carbetamide; from the group of the VLCFA inhibitors:
  • chloroacetamides such as acetochlor, alachlor, dimethenamid, dimethenamid-P, metolachlor, metolachlor-S, pretilachlor and propachlor; oxyacetanilides such as flufenacet and mefenacet; acetanilides such as diphenamid; tetrazolinones such as fentrazamide, and other herbicides such as cafenstrole, and pyroxasulfone; from the group of the cellulose biosynthesis inhibitors: isoxaben; from the group of the decoupler herbicides: dinoseb; from the group of the auxinic herbicides:
  • 2,4-D and its salts and esters such as clacyfos, dicamba and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, quinclorac and quinmerac; from the group of the auxin transport inhibitors: diflufenzopyr; - from the group of the other herbicides: indaziflam and pelargonic acid.
  • compositions according to the present invention can also comprise at least one safener.
  • safeners are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31 -4) and N-(2-Methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide (
  • More preferred safeners are benoxacor, cloquintocet, cyprosulfamide, dichlormid,
  • fenchlorazole fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1 -oxa-4- azaspiro->[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31 -4).
  • the safeners are known compounds, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine [CAS No.
  • the herbicides, plant growing regulators and/or safeners as described herein having a carboxyl, hydroxy and/or an amino group can be employed as such or in form of an agriculturally suitable salt as mentioned above or in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2- yl)methyl) esters and also as thioesters, for example as Ci-Cio-alkylthio esters.
  • an agriculturally suitable salt as mentioned above or in the form of an agriculturally acceptable derivative
  • esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl (
  • Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 - methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2- methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
  • the invention also relates to agrochemical compositions comprising the composition according to the present invention, at least one inert liquid and/or solid carrier and, if appropriate, at least one auxiliary customary for herbicidal formulations.
  • agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • suspensions e.g. SC, OD, FS
  • emulsifiable concentrates e.g. EC
  • emulsions e.g. EW, EO, ES, ME
  • capsules e.g.
  • agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Customary agitating (e.g. mixing) devices which, if appropriate, can be heated may be used for preparing the mixtures.
  • Suitable solvents and liquid carriers are water and 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 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; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; 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
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable auxiliaries are solvents, surfactants differing from the surfactant B according to the present invention, dispersants, emulsifiers, wetters, adjuvants, solubilizers, uptake enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • 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 emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant.
  • surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha- olefin sulfonates, lignine 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.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Suitable non-ionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic 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.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
  • 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 preservatives, colorants and perfumes are known to the skilled worker, for example from the literature mentioned above in connection with surfactants, and from Watkins,
  • the herbicidal compositions of the invention affect a very good control of vegetation in non-crop areas, especially at high application rates.
  • 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.
  • Suitable crops are, for example, the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • 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 described herein are useful for controlling undesired vegetation.
  • the compositions may be applied as such or are preferably applied after dilution with water.
  • a so-called aqueous spray-liquor is prepared by diluting the compositions of the present invention with water, e.g. tap water.
  • the spray-liquors 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 non-phytotoxic oils or oil concentrates.
  • these constituents are added to the spray mixture before, during or after dilution of the compositions according to the invention.
  • the compositions of the invention can be applied by the pre-emergence or the post-emergence method.
  • compositions to the present invention are less well tolerated by certain crop plants, application techniques may be employed where the 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, layby).
  • compositions of the invention are applied to such a degree that the application rates of component A) are from 0.001 to 3.0 kg/ha, preferably from 0.01 to 1.0 kg/ha, more preferably from 0.01 to 0.5 kg/ha active ingredient (a.i.).
  • compositions of the present invention as a tank-mix partner with other formulations.
  • 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.
  • the fatty alcohol was fed to a reactor, then 0.2 w% of a solution of KOH in water (50 w% KOH and 50 w% water) was added and the mixture stirred. Then the mixture was dried in dynamic vacuum for 1 hour at 80°C and ⁇ 30 mbar. The valve to the vacuum was closed, the mixture heated to 165°C and the respective amount of alkylene oxide added. During dosing the pressure was always kept below 5 bar. After the desired amount of alkylene oxide had been added, the mixture was post-reacted for 30 minutes at 165°C, then cooled to 60°C and neutralized with a solution of lactic acid (80% lactic acid and 20% water). Finally the stirring was stopped and the alkyl alkoxide discharged.
  • KOH in water 50 w% KOH and 50 w% water
  • Tetraphosphoric acid (1 equivalent, calculated as H6P4O13) was fed to a reactor, the latter flushed with nitrogen and heated to 40°C.
  • 2.5 equivalents of alcohol alkoxylate were added, at a speed that allowed the temperature of the mixture in the reactor to stay at max. 60°C.
  • the temperature was raised to 90°C, and the reaction mixture was post-reacted upon stirring for 6 hours at 90°C.
  • the reactor was discharged to yield the crude monophosphate of the alkoxylate, which was used in the subsequent trials without further purification.
  • Alcohol alkoxylate (6 equivalents) was fed to a reactor, the latter flushed with nitrogen and heated to 40°C. Upon stirring 1 equivalent of P4O10 was added, at a speed that allowed the temperature of the mixture in the reactor to stay at max. 60°C. After complete addition of the phosphorous oxide, the temperature was raised to 90°C, and the reaction mixture was post- reacted upon stirring for 2 hours at 90°C. The reactor was discharged to yield the crude mixture of mono- and diphosphate of the alkoxylate, which was used in the subsequent trials without further purification. 1.4. Preparation of sulfates
  • the fatty alcohol alkoxylate (1 equivalent) was mixed with the same amount of methylene chloride to yield a 50 w% solution, then charged into a reactor, flushed with nitrogen, stirred and cooled to +5°C. Then 1 equivalent chlorosulfonic acid was added at a speed that allowed the temperature of the mixture in the reactor to stay at max. 20°C. After complete addition of the HSO3CI the reaction mixture was post-reacted for 3 hours at room temperature.
  • the crude alkoxilate sulfate was added upon stirring to a solution of 1.6 equivalents of NaOH in 30 equivalents of water. Depending on the alkoxilate starting material, further water had to be added to prevent solidification of the system. Then the resulting mixture was adjusted to pH 7 by addition of 10 w% H2SO4 or 10 w% NaOH.
  • Ci3/i5-oxoalcohol 2 5 block first PO, then EO -OH 1.1.10 Ci3/i5-oxoalcohol 12 6 random -OH
  • Ci3/i5-oxoalcohol 2 5 block first PO, then EO -OSOsNa
  • Cio-oxoalcohol - prepared by hydrogenation of hydroformylated trimeric propene
  • Ci3/i5-oxoalcohol prepared by hydrogenation of hydroformylated Ci 2 -Ci4-a-olefin 2.
  • a phosphate of table 1 , section 1 .2 (71.4 % by weight) was mixed with alcohol alkoxylate 1 .1 .5 (28.6 % by weight) acting as retention enhancer and hydrotrope to get a clear viscous solution.
  • alcohol alkoxylate 1 .1 .5 28.6 % by weight
  • a phosphate of table 1 , section 1.2 (25 % by weight) and alcohol alkoxylate 1 .1 .5 (10 % by weight) were mixed with 50% by weight of a 20% by weight aqueous solution of ethanol and agitated.
  • the pH of the mixture was adjusted to 6.5 - 7.5 using potassium hydroxide in form of 50% aqueous solution.
  • the resulted mixture was filled up to 100% by weight with the aforesaid 20% by weight aqueous solution of ethanol to get a clear low viscous solution.
  • section 2.2 using mono-/di-phosphates of table 1 , section 1 .3.
  • a sulfate of table 1 , section 1.4 was mixed with alcohol alkoxylate 1 .1 .5 in a surfactant weight ratio of 2.5 parts sulfate to 1 part isotridecanol alkoxilate. The resulted mixture was 2-fold diluted with ethanol to yield a clear low viscous solution.
  • methyl oleate or b) paraffin oil 90% by weight of methyl oleate or paraffin oil, respectively, was mixed with 10% by weight of emulsifier (consisting of castor oil ethoxylate and calcium arylalkylsulfonate) to yield a clear emulsifiable oil.
  • emulsifier consisting of castor oil ethoxylate and calcium arylalkylsulfonate
  • fatty acid dimethyl amide 20 w% tristyryl phenol alkoxilate (Soprophor® 796 P) was mixed with 5 w% water and 75 w% decanoic acid ⁇ , ⁇ -dimethyl amide (Genagen® 4296) to yield a clear emulsifiable oil.
  • Cornexistin or hydroxycornexistin was added to a mixture of cyclohexanone (80% by weight of the mixture) and castor oil ethoxylate (20% by weight of the mixture) to get a soluble liquid comprising 200 g/l of an active ingredient.
  • a spray liquor comprising 133 mg/l of cornexistin or 100 mg/l hydroxycornexistin was prepared by tank mixing a formulation according to section 2.6 with water.
  • a spray liquor comprising 133 mg/l of cornexistin or 100 mg/l hydroxycornexistin and 0.36% by weight of a surfactant according to Table 1 was prepared by tank mixing a formulation according to section 2.6 with a formulation according to the sections 2.1 -2.4 and water.
  • Grass weeds (ALOMY, SETVI, SETFA, LOLRI, ECHCG, PANMI, DIGSA) and broadleaf weeds (ABUTH, AMBEL, ERICA, CHEAL, SOLNI) where treated with a spray liquor prepared according to section 3 (375 l/ha, corresponds to 50 g/ha of cornexistin and 38g/ha of hydroxycornexistin).
  • the plants used in the greenhouse experiments were of the following species:
  • the culture containers were plastic flower pots containing loamy sand with approximately 3.0% of humus as the substrate.
  • test plants were first grown to a height of 3 to 15 cm depending on the plant habit and only then treated with the active compounds suspended in water. They were either grown directly in the test containers or transplanted as seedlings into the test containers a few days prior to treatments.
  • the plants were kept at 10 to 25°C or 20 to 35°C.
  • the test period extended over three weeks. During this time the plants were tended and their response to the individual treatment was evaluated.
  • Damage by the herbicidal compositions was evaluated with reference to a scale of 0% to 100% in comparison with untreated control plots. 0 means no damage and 100 means complete destruction of the plants. The mean value was calculated for grass weeds and broadleaf weeds.

Abstract

La présente invention concerne des compositions herbicides comprenant un composé de formule I, dans laquelle R1, R2 et R3 sont tels que définis dans la description et un tensioactif sélectionné parmi des tensioactifs anioniques et/ou non ioniques non substitués ayant un groupe OH de fonction acide et/ou alcool, dans lequel au moins 50 % en poids du tensioactif B sont présents sous forme non ionisée. L'invention concerne également le procédé de préparation, d'utilisation et les procédés d'utilisation de ces concentrés.
PCT/EP2015/063268 2014-06-25 2015-06-15 Compositions herbicides comprenant de la cornexistine et/ou de l'hydroxycornexistine WO2015197392A1 (fr)

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US10238106B2 (en) 2014-03-12 2019-03-26 Basf Se Carbonates of alcohol alkoxylates as adjuvants for crop protection
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10765112B2 (en) 2015-06-19 2020-09-08 Basf Se Pesticidal microcapsules with a shell made of tetramethylxylylene diisocyanate, cycloaliphatic diisocyanate, and aliphatic diamine
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
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US11051510B2 (en) 2014-01-30 2021-07-06 Basf Se Asymmetric formales and acetales as adjuvants for crop protection
US11064701B2 (en) 2016-06-03 2021-07-20 Basf Se Benzoxaborole compounds
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US11219215B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific inhibitors of protoporphyrinogen oxidase
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US11247980B2 (en) 2016-05-24 2022-02-15 Basf Se Herbicidal uracilpyrid
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors
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US11051510B2 (en) 2014-01-30 2021-07-06 Basf Se Asymmetric formales and acetales as adjuvants for crop protection
US10238106B2 (en) 2014-03-12 2019-03-26 Basf Se Carbonates of alcohol alkoxylates as adjuvants for crop protection
US10827748B2 (en) 2014-03-12 2020-11-10 Basf Se Carbonates of alcohol alkoxylates as adjuvants for crop protection
US10167297B2 (en) 2014-10-24 2019-01-01 Basf Se Substituted pyridine compounds having herbicidal activity
US10375959B2 (en) 2015-01-22 2019-08-13 BASF Agro B.V. Ternary herbicidal combination comprising saflufenacil
US10765112B2 (en) 2015-06-19 2020-09-08 Basf Se Pesticidal microcapsules with a shell made of tetramethylxylylene diisocyanate, cycloaliphatic diisocyanate, and aliphatic diamine
US11089780B2 (en) 2015-06-19 2021-08-17 Basf Se Pendimethanlin microcapsules with a shell made of tetramethylxylylene diisocyanate and a polyamine with at least three amine groups
US10813356B2 (en) 2015-07-10 2020-10-27 BASF Agro B.V. Herbicidal composition comprising cinmethylin and dimethenamid
US10980232B2 (en) 2015-07-10 2021-04-20 BASF Agro B.V. Herbicidal composition comprising cinmethylin and pyroxasulfone
US10897898B2 (en) 2015-07-10 2021-01-26 BASF Agro B.V. Herbicidal composition comprising cinmethylin and acetochlor or pretilachlor
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
US11219212B2 (en) 2015-07-10 2022-01-11 BASF Agro B.V. Herbicidal composition comprising cinmethylin and imazamox
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
US11247980B2 (en) 2016-05-24 2022-02-15 Basf Se Herbicidal uracilpyrid
US11064701B2 (en) 2016-06-03 2021-07-20 Basf Se Benzoxaborole compounds

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