EP4340620A1 - Herbizidzusammensetzung und verfahren zu ihrer herstellung - Google Patents

Herbizidzusammensetzung und verfahren zu ihrer herstellung

Info

Publication number
EP4340620A1
EP4340620A1 EP22804216.4A EP22804216A EP4340620A1 EP 4340620 A1 EP4340620 A1 EP 4340620A1 EP 22804216 A EP22804216 A EP 22804216A EP 4340620 A1 EP4340620 A1 EP 4340620A1
Authority
EP
European Patent Office
Prior art keywords
methyl
sodium
clodinafop
propargyl
composition
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
EP22804216.4A
Other languages
English (en)
French (fr)
Inventor
Mallikarjunappa Siddappa
Kendappa GOWDRA NANJAPPA
Dinesh Sharma
Rupak PAUL
Vijay Kumar Reddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rallis India Ltd
Original Assignee
Rallis India Ltd
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.)
Filing date
Publication date
Application filed by Rallis India Ltd filed Critical Rallis India Ltd
Publication of EP4340620A1 publication Critical patent/EP4340620A1/de
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a herbicide composition and a process for preparing the same.
  • Metsulfuron-methyl, Clodinafop-propargyl, Metribuzin are compounds known to be herbicidally active and to be of use in the control of undesirable vegetation, for example in the protection of a range of crops.
  • the herbicides metsulfuron-methyl, clodinafop-propargyl, and metribuzin are independently known in the art for their herbicidal potency. They are disclosed in ‘The Pesticide Manual’ 15 th Edition, published 2009 by the British Crop Protection
  • metsulfuron-methyl, clodinafop-propargyl, and metribuzin are herbicidally active, in many cases they do not provide sufficient control of relevant harmful plants and the activities at low application rates are not always satisfactory.
  • the recommended level of herbicide that may be applied per unit of area is under pressure from governmental, as well as for economic and environmental reasons.
  • the present invention provides a herbicide composition comprising metsulfuron-methyl, clodinafop-propargyl and metribuzin.
  • the herbicide composition comprises metsulfuron-methyl in an amount of from 0.01% to 10 % w/w, clodinafop-propargyl in an amount of from 0.1% to 25% w/w and metribuzin in an amount of from 1.0% to 60% w/w.
  • the herbicide composition of the present invention is formulated in a number of ways for suitable application.
  • suitable formulations include water-dispersible granule (WDG), a water-soluble granule (SG), a wettable powder (WP), a water-dispersible powder (WDP), a water-soluble powder (SP), a granule (GR), an encapsulated granule (CG), a fine granule (FG), a macrogranule (GG), a microgranule (MG), a suspension concentrate (SC), a water-soluble concentrate (SL), an emulsifiable concentrate (EC), an emulsion (EW), a micro-emulsion (ME), a flowable suspension (FS), a suspoemulsion (SE), ZC formulation (ZC), soil applied granules (SAG), dustable powder (DP), a gel, a water-dispersible tablet (WT), a dispersible concentrate (DC), an oil-dispersion (OD) or a microencapsulated suspension (CS).
  • WDG water-dispersible gran
  • the herbicide composition of the present invention is preferably formulated as an oil-dispersion (OD), a wettable powder (WP) and a water- dispersible granule (WDG).
  • OD oil-dispersion
  • WP wettable powder
  • WDG water- dispersible granule
  • the present invention provides a process for preparing the herbicide composition.
  • the process comprises mixing metsulfuron-methyl, clodinafop- propargyl and metribuzin.
  • the present invention provides a process for preparing oil- dispersion (OD), a wettable powder (WP) and a water-dispersible granule (WDG) formulation.
  • OD oil- dispersion
  • WP wettable powder
  • WDG water-dispersible granule
  • the numbers expressing quantities of ingredients, properties such as concentration, process conditions, and so forth, used to describe and claim certain embodiments of the invention are to be understood as being modified in some instances by the term “about.” Accordingly, in some embodiments, the numerical parameters set forth in the written description are approximations that can vary depending upon the desired properties sought to be obtained by a particular embodiment. In some embodiments, the numerical parameters should be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of some embodiments of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as practicable.
  • inventive subject matter provides many example embodiments of the inventive subject matter. Although each embodiment represents a single combination of inventive elements, the inventive subject matter is considered to include all possible combinations of the disclosed elements. Thus, if one embodiment comprises elements A, B, and C, and a second embodiment comprises elements B and D, then the inventive subject matter is also considered to include other remaining combinations of A, B, C, or D, even if not explicitly disclosed.
  • locus includes not only areas where weeds may already be growing, but also areas where weeds are yet to emerge, and also areas under cultivation.
  • plant refers to all physical parts of a plant, including shoots, leaves, needles, stalks, stems, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • inactive excipients means excipients which are known and accepted in the art for formation of formulations for agricultural or horticultural use.
  • pre-emergence refers to application of the herbicide composition to a habitat, a weed, or soil, prior to emergence of weeds from a soil surface.
  • post-emergence refers to application of the herbicide composition to weeds that have already emerged from a soil surface.
  • undesirable vegetation denotes non crop plant species that otherwise tend to grow in areas where crops are planted, and includes both volunteer crops and weeds.
  • the weeds include broadleaf weeds and grassy weeds.
  • control of undesirable vegetation refers to interference with normal growth and development of undesired vegetation.
  • Examples of control of undesirable vegetation include, but not limited to, inhibition of root growth, inhibition of shoot growth, inhibition of shoot emergence, inhibition of seed production, or reduction of weed biomass.
  • the present invention does not use any ‘biological materials’ that is the materials which are capable of reproducing itself or being reproduced in a biological system.
  • the present disclosure provides a herbicide composition comprising combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin.
  • Metsulfuron-methyl chemically known as methyl 2-[[[[[(4-methoxy-6- methyl-l,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate is a triazinylsulfonylurea herbicide. It is a selective pre-emergence and post emergence herbicide used for the control of wide range of broad-leaved weeds in wheat, barley and rice. It acts by inhibiting acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS).
  • ALS acetolactate synthase
  • AHAS acetohydroxy acid synthase
  • Clodinafop-propargyl chemically known as 2-propynyl (2R)-2-[4-[(5- chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoate is a aryloxyphenoxypropionic herbicide. It is a selective systemic post emergence herbicide used for the control of grassy weeds in cereals mainly wheat. It acts by inhibition of acetyl CoA carboxylase.
  • Metribuzin chemically known as 4-amino-6-(l,l-dimethylethyl)-3- (methylthio)-l,2,4-triazin-5(4H)-one is a triazinone herbicide. It is a selective pre-emergence and post-emergence herbicide used for controlling broadleaved weeds and annual grasses in crops like sugarcane, wheat and soyabean. It acts by inhibiting photosynthesis by disrupting photosystem II in plants.
  • the present invention is based upon a surprising finding that metsulfuron-methyl, clodinafop-propargyl, and metribuzin display a synergistic herbicidal effect in the control of undesirable vegetation when applied in combination comprising all three compounds.
  • the synergistic effects allow a reduction in application rate of individual active ingredients, a faster onset of herbicidal action, a longer-lasting action, better control of undesirable vegetation with only one or a few applications, and a broadening of possible application period.
  • the synergistic effects of the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin will provide one or more of a number of advantages over the use of each active ingredient alone.
  • the rates of application of each active ingredient is markedly reduced, when the three compounds are used in combination, while maintaining a high level of herbicidal efficacy.
  • the use of the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin has the potential to control weed species at a low application rate, in particular at a rate of application at which the individual active ingredients alone are ineffective.
  • a treatment using the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin exhibit a considerably broader weed spectrum than the compounds when used alone.
  • the use of a composition comprising the three aforementioned active ingredients also has a speed of action which is faster than that which would have been predicted from the speed of each ingredient used individually and in combination of two ingredients.
  • the herbicide composition according to the present disclosure is advantageous in the protection of cereal crops, preferably wheat crop.
  • the herbicide composition of the present disclosure is useful for post emergence control of undesirable vegetation.
  • the undesirable vegetation whose control is of greatest interest in the practice of present invention are weeds, and primarily those weeds associated with wheat.
  • the control of undesirable vegetation in wheat is achieved by applying to the undesirable vegetation or to locus of the vegetation the combination of metsulfuron- methyl, clodinafop-propargyl and metribuzin in suitable amounts.
  • effective herbicidal effect is achieved with post-emergence application of the herbicide composition of the present disclosure.
  • Useful methods of application include broadcast or localized spraying, drip irrigation or other forms of irrigation, and any of these methods followed by soil tilling.
  • the application rates of the herbicide composition to soil vary over a wide range. The optimal application rates will depend on the crop to be protected, the stage of growth of the crop and of the weed, and the manner in which application is made, i.e., whether by spraying, irrigation, or other means.
  • the total application rate of metsulfuron-methyl, clodinafop- propargyl and metribuzin vary within a wide range, for example from 1 to 2000g per hectare (g/ha). Preferably, the application rate ranges from 20 to 1000 g/ha.
  • the herbicide composition disclosed herein is applied in a single treatment or in several treatments (sequential application), for example by one or more post-emergence applications or one or more early post-emergence applications, and/or followed by one or more applications at medium or late post-emergence.
  • the active ingredients metsulfuron-methyl, clodinafop-propargyl and metribuzin are present in the composition in a wide range of amounts.
  • the total amount of metsulfuron-methyl, clodinafop- propargyl and metribuzin in the composition range from 0.1% to 95% by weight of the composition.
  • the composition comprises, by weight, from 0.01-10% w/w of metsulfuron-methyl, from 0.1 - 25% of clodinafop-propargyl and from 1.0 - 60.0 % w/w of metribuzin.
  • the herbicide composition of the present disclosure is formulated in conventional manner, for example by mixing metsulfuron-methyl, clodinafop- propargyl and metribuzin with one or more inactive excipients. Suitable excipients will depend upon such factors as the type of formulation and the manner of the end use of the formulation, and will be known to a person skilled in the art.
  • the one or more inactive excipients are selected from anti-crystalline agent, an emulsifier, a wetting agent, a pH modifier, rheology modifier, a solvent, a spreading agent, a dispersing agent, an inert carrier, a stabilizing agent, an anti-caking agent, an anti-foaming agent, an antioxidant or an anti-freezing agent.
  • the anti-crystalline agent is selected from vinyl pyrrolidone polymer, calcium salts of (linear and branched) alkyl benzene sulfonic acid or sodium salt of lignosulfonate.
  • the anti -crystalline agent is present in an amount of from 0.1% to 5% by weight based on a total weight of the composition.
  • Suitable emulsifier for use in the composition include all substances which normally be used for this purpose in agrochemical compositions. Examples include substances which are non-ionic, cationic and/or anionic in nature.
  • Suitable emulsifiers include, but not limited to, salts of polyacrylic acids, salts of lignosulphonic acid, salts of phenylsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols, especially alkylphenols, sulphosuccinic ester salts, taurine derivatives, especially alkyl taurates, and phosphoric esters of polyethoxylated phenols or alcohols, ethoxylated ricinoleic acid triglycerides, castor oil ethoxylate, tristyryphenol ethoxylate or ethoxylated propoxylated polyarylphenol.
  • the emulsifier is present in an amount of from 1% to 12% by weight based on a total weight of the composition.
  • the wetting agent is selected from alkyl phenol ethoxylate, fatty oil ethoxylate, phenyl naphthalene sulphonates, alkyl naphthalene sulfonates, sodium alkyl naphthalene sulfonate, sodium salt of sulfonated alkyl carboxylate, dioctyl sulfosuccinate sodium salt, polyoxyalkylated ethyl phenols, polyoxyethoxylated fatty alcohols, polyoxyethoxylated fatty amines, lignin derivatives, alkane sulfonates, alpha olefin sulfonates, alkylbenzene sulfonates, salts of polycarboxylic acids, salts of esters of sulfosuccinic acid, octyl phenol ether sulphate, anionic phosphate esters, disodium laureth s
  • the pH modifier is selected from sodium silicate, potassium silicate, magnesium silicate, manganese silicate, sodium pyrophosphate, sodium acetate, sodium oxalate, sodium carbonate, sodium bicarbonate, sodium bentonite, sodium acetate, attapulgite, diatomaceous earth, sodium zeolite, trisodium phosphate, trisodium citrate, magnesium carbonate, magnesium sulphate, monoethanol amine, triethanol amine, triethylamine, dibasic esters selected from dimethyl succinate, dimethyl glutarate, dimethyl adipate and mixtures thereof.
  • the pH modifier is present in an amount of from 0.01% to 4% by weight based on a total weight of the composition.
  • the rheology modifier is selected from hydrophobic silica, fume silica, bentonite, diatomaceous earth, montmorillonite, attapulgites or hydroxymethyl cellulose, xanthan gum, polyvinyl alcohol, cellulose and its derivatives, hydrated clay minerals, magnesium aluminium silicates and mixtures thereof.
  • the rheology modifier is present in an amount of from 0.1% to 8% by weight based on a total weight of the composition.
  • Suitable solvents for use in the composition is selected from all customary organic solvents which dissolve one or more of the active ingredients employed.
  • Suitable organic solvents for the compounds metsulfuron-methyl, clodinafop-propargyl and metribuzin are known in the art.
  • Preferred solvents include, but not limited to, deionized (DI) water, vegetable oils, methylated vegetable oils, oil medium selected from the group comprising, esterified fatty acids selected from methyl ester of triglycerides containing Cn -Cn saturated and unsaturated fatty acids, ethyl ester of triglycerides containing Cn -C22 saturated and unsaturated fatty acids such as methyl soyate, ethyl soyate, rapeseed methyl ester, rapeseed ethyl ester, bio diesels, paraffinic oil or tall oil.
  • the solvent is present in an amount of from 10% to 90% by weight based on a total weight of the composition.
  • Suitable spreading agents are selected from the group comprising of polyoxyethylene alkyl ether, trisiloxane ethoxylate, polysorbates, ethoxylated tristyrylphenol phosphate, sodium lauryl sulphate or sodium methyl oleoyl taurate. Spreading agents is present in the composition in an amount ranging from 0.1 to 10 % w/w.
  • the dispersing agent is selected from lignosulphonates, phenyl naphthalene sulphonates, ethoxylated alkyl phenols, ethoxylated fatty acids, alkoxylated linear alcohols, polyaromatic sulfonates, sodium alkyl aryl sulfonates, maleic anhydride copolymers, phosphate esters, condensation products of aryl/alkyl sulphonic acids and formaldehyde, addition products of ethylene oxide and fatty acid esters, sulfonates of condensed naphthalene, lignin derivatives, naphthalene formaldehyde condensates, polycarboxylates, sodium alkyl benzene sulfonates, salts of sulfonated naphthalene, polystyrenated acrylated co- polymer, ammonium salts of sulfonated naphthalene, salt
  • Suitable inert carrier(s) for use in the composition include, but not limited to, natural ground minerals, such as kaolin or china clay, alumina, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminium oxide, silicates, and calcium phosphates and calcium hydrogen phosphates, crushed and fractionated natural minerals, such as calcite, marble, pumice, precipitated silica, sepiolite, bentonite, river sand, zeolites, starch, sand, talc, quartz and dolomite, or synthetic granules of inorganic and organic ground materials.
  • the inert carrier is present in an amount of from 1% to 99% by weight based on a total weight of the composition.
  • the stabilizing agent is selected from modified hydrophobic silica, colloidal silica, precipitated silica, hydrophobic silica powder and mixtures thereof.
  • the stabilizing agent is dimethyldichlorosilane -treated fumed silica.
  • the stabilizing agent is selected from epoxidized soybean oil, gamma butyrolactone, butylated hydroxyl toluene and its derivatives, epichlorhydrin, quinone derivatives, hydrazine hydrates and its derivatives, general class UV stabilizers, glycols and its derivatives and mixtures thereof.
  • the stabilizing agent is present in an amount of from 0 to 6% by weight based on a total weight of the composition.
  • the anti-caking agent is selected from kaolin clay, precipitate silica, colloidal silica, fumed silica, talc, gypsum, silicates, calcium carbonate, magnesium carbonate, magnesium sulfate, and mixtures thereof.
  • the anti caking agent is present in an amount of from 0 to 6% by weight based on a total weight of the composition.
  • Suitable anti-foaming agents for use in the composition include all substances which normally be used for this purpose in agrochemical compositions. Particularly preferred anti-foaming agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foaming agents available from GE or Compton. The anti-foaming agent is present in an amount of from 0 to 2% w/w by weight based on a total weight of the composition.
  • Suitable antioxidants are all substances which normally be used for this purpose in agrochemical compositions, as is known in the art.
  • Preferred antioxidant is butylated hydroxytoluene.
  • Antioxidant is present in an amount of from 0 to 5% w/w by weight based on a total weight of the composition.
  • Suitable anti-freezing agents include organic solvents which are completely miscible with water, such as ethylene glycol, propylene glycol, other glycols, glycerine or urea. Anti-freezing agent is present in the composition in an amount of from 0 to 5% w/w.
  • the herbicide composition additionally includes one or more agrochemical active compounds, such as insecticides, nematicides, fungicides, safeners such as cloquintocet methyl or mefenpyr-diethyl, growth factor enhancers or fertilizers, in addition to the components metsulfuron-methyl, clodinafop- propargyl and metribuzin.
  • agrochemical active compound is present in the composition in an amount ranging from 0 to 6.5% w/w.
  • the herbicide combination exists as mixed formulations of metsulfuron-methyl, clodinafop- propargyl and metribuzin, which is then be used in a conventional way by diluting with water or prepared as tank mixes by jointly diluting separately formulated or partially separately formulated active ingredients with water or with aqueous solutions.
  • the herbicide composition comprising the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin is formulated in liquid or solid form.
  • the disclosed herbicide composition is formulated as a water-dispersible granule (WDG), a water-soluble granule (SG), a wettable powder (WP), a water-dispersible powder (WDP), a water-soluble powder (SP), a granule (GR), an encapsulated granule (CG), a fine granule (FG), a macrogranule (GG), a microgranule (MG), a suspension concentrate (SC), a water-soluble concentrate (SL), an emulsifiable concentrate (EC), an emulsion (EW), a micro-emulsion (ME), a flowable suspension (FS), a suspoemulsion (SE), ZC formulation (ZC), Soil Applied Granules (SAG), dustable powder (DP), a gel, a water-dispersible tablet (WT), a dispersible concentrate (DC), an oil-dispersion (OD), or a microencapsulated suspension (CS)
  • the herbicide composition comprising the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin is formulated as an oil-dispersion (OD).
  • the herbicide composition comprising the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin is formulated as wettable powder (WP).
  • WP wettable powder
  • the herbicide composition comprising the combination of metsulfuron-methyl, clodinafop-propargyl and metribuzin is formulated as water-dispersible granule (WDG).
  • WDG water-dispersible granule
  • the herbicide composition comprising combination of metsulfuron- methyl, clodinafop-propargyl and metribuzin of the present disclosure is useful in controlling growth of undesirable vegetation by post-emergence application.
  • the herbicide composition is applied to undesirable vegetation and/or locus in a variety of ways, at various concentrations.
  • the herbicide composition is applied to the undesirable vegetation and/or locus by various methods, including coating, spraying, sprinkling, dipping, soaking, injection, irrigation, and the like.
  • the present disclosure further provides a process for preparing the herbicide composition described herein.
  • the herbicide composition is prepared by mixing the respective active compounds and, if appropriate, one or more inactive excipients.
  • the present disclosure is further explained in the form of following examples. However, it is to be understood that the foregoing examples are merely illustrative and are not to be taken as limitations upon the scope of the invention. Various changes and modifications to the disclosed embodiments will be apparent to those skilled in the art. Such changes and modifications may be made without departing from the scope of the invention.
  • Example 1 Herbicide composition of the present invention. Table A
  • Oil-dispersion (OD) formulation of the present invention Oil-dispersion (OD) formulation of the present invention.
  • Oil-dispersion (OD) formulation of the present invention Oil-dispersion (OD) formulation of the present invention.
  • the “accelerated storage test” is considered as an indicative of product stability. That is accelerated storage test data provides an indication that the product is stable for at least two years at ambient temperature. Further, the FAO/WHO manual indicates storage at 54°C ⁇ 2°C for 14 days as the default test conditions.
  • the ambient sample of the oil-dispersion (OD) formulation of the present invention was subjected to the accelerated storage test to find out the product stability.
  • Table 1 shows the physical and chemical properties of the oil- dispersion (OD) formulation, before and after the accelerated storage test.
  • the oil-dispersion (OD) formulation was prepared according to Example 5.
  • the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl was found to be 0.40% w/w, 6.00% w/w, 21.00% w/w, 1.50 % w/w respectively before subjecting the ambient sample to the accelerated storage test.
  • the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl was found to be almost same, that is 0.39%w/w, 5.98 %w/w, 20.89%w/w, 1.50 %w/w respectively. It indicates that the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl is not degraded.
  • the pH of the ambient sample of the OD formulation before subjecting it to the accelerated storage test was found to be 7.73. However, even after subjecting the ambient sample to the accelerated storage test the pH was found to be almost same, that is 7.74. It indicates that the oil-dispersion was adhering to the pH range of 7.0 -9.5 which indicates that the formulation is stable.
  • Dispersion stability test is performed to ensure that a sufficient proportion of active ingredient is homogeneously dispersed in the spray liquid to give a satisfactory and effective mixture throughout spraying.
  • the ambient sample and accelerated storage sample of the oil-dispersion (OD) formulation, subjected to dispersion stability test did not show any cream or sedimentation even after 0.5 hours of the dispersion or 24.5 hours of the re-dispersion test.
  • the ambient sample of the oil-dispersion (OD) formulation was diluted in water and was tested for its particle size by wet sieve passing test by using 75 m wet sieve.
  • the wet sieve passing test showed passing of 99.94%w/w and 99.92%w/w of particles of the formulation through the 75m wet sieve indicating the low particle size of the formulation and no crystal growth after the accelerated storage test.
  • oil-dispersion (OD) formulation of the present invention prepared in accordance with the above examples are extrapolated to be stable for 2 years.
  • Example 8 Herbicide composition of the present invention. Table D
  • WP Wettable powder
  • WDG Water-dispersible granule
  • the process for preparing the Wettable powder (WP) and Water- dispersible granule (WDG) formulation comprises the steps as below.
  • a blend of 0.4% w/w metsulfuron-methyl, 21% w/w metribuzin, 10% w/w polystyrenated acrylated co-polymer, 3% sodium alkyl naphthalene sulfonate, 1% w/w trisodium phosphate and 33.1 % w/w china clay was prepared by blending them for 1 hour.
  • the blend was passed through aiqet mill to prepare a milled material having a reduced particle size (D90 ⁇ 18m).
  • 6.0 %w/w clodinafop-propargyl and/or 1.5 w/w cloquintocet methyl was weighed into a clean vessel fitted with pressurised spray gun.
  • the 6.0 %w/w clodinafop-propargyl and/or 1.5 w/w cloquintocet methyl mixture was heated at 60°C-65°C to melt completely. 4.0% w/w ethoxylated tristyrylphenol phosphate was added into it and mixed well to obtain the melted form of clodinafop-propargyl. Melted form of clodinafop-propargyl mixture was uniformly sprayed on 20%w/w precipitated silica by a pressurised spray gun and continued to mix for lhr.
  • Table 2 shows the physical and chemical properties of the WP formulation, before and after the accelerated storage test.
  • the WP formulation was prepared according to Example 9.
  • the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl is found to be almost same, that is 0.38% w/w , 5.92 %w/w, 20.93% w/w, 1.48 %w/w respectively. It indicates that the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl is not degraded.
  • the pH of the ambient sample of the wettable powder (WP) before subjecting it to the accelerated storage test was found to be 7.8. However, even after subjecting the ambient sample to the accelerated storage test the pH was found to be almost same, that is 7.7. It indicates that the wettable powder (WP) was adhering to the pH range of 7.0 - 9.5 which indicates that the formulation is stable.
  • the suspensibility test was conducted for the ambient sample of the wettable powder (WP) formulation, before and after accelerated storage test. The results of the suspensibility test indicated that, 87% and 82 % of WP formulation are uniformly distributed in water after dilution.
  • Tests such as persistent foam and wettability were also conducted for the ambient sample of the wettable powder (WP), before and after accelerated storage test.
  • the wettability test showed that the time taken to wet the powder is only 90 and 81 seconds indicating the fast wetting of the powder upon water dilution.
  • the wet sieve passing test showed passing of 99.50%w/w and 99.30%w/w of particles of the formulation through the 75 m wet sieve indicating the low particle size of the formulation.
  • wettable powder (WP) of the present invention prepared in accordance with the above examples are extrapolated to be stable for 2 years.
  • WDG water-dispersible granule
  • Table 3 shows the physical and chemical properties of the WDG formulation, before and after the accelerated storage test.
  • the WDG formulation is prepared according to Example 9.
  • the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl was found to be 0.40% w/w, 6.00 %w/w, 21.00% w/w, 1.50 %w/w respectively before subjecting the ambient sample to the accelerated storage test. After subjecting the ambient sample to the accelerated storage test (that is storing at 54 ⁇ 2°C for 14 days in the HDPE containers) the content of metsulfuron-methyl, clodinafop-propargyl, metribuzin and cloquintocet methyl was found to be almost same, that is
  • Tests such as persistent foam, wettability and degree of dispersion and moisture content were also conducted for the ambient sample of the water dispersible granule (WDG), before and after accelerated storage test.
  • WDG water dispersible granule
  • Degree of dispersion test showed that 75% and 71% of granules were dispersed uniformly and formed homogeneous dispersion.
  • Moisture content test showed low moisture content of 1.72% and 1.69% indicating dried granules.
  • the wet sieve passing test showed passing of 99.60%w/w and 99.10%w/w of particles of the formulation through the 75m wet sieve indicating the low particle size of the formulation.
  • WDG water dispersible granule
  • compositions comprising metsulf iron- methyl, clodinafop-propargyl and metribuzin formulated into OD formulation resulted in more than 90 % reduction of weeds in comparison to the untreated check.
  • the percentage reduction of weeds by the present composition is higher than the individual compounds as well as conventional combinations.
  • Table 6 Effect of pre-mix metsulfuron-methyl 0.4% + clodinafop- propargyl 6% + metribuzin 21% wettable powder (WP) and water-dispersible granule (WDG) formulation against major weeds in wheat at the Chandigarh location in the Rabi season 2020.
  • compositions comprising metsulfuron- methyl, clodinafop-propargyl and metribuzin formulated into WP and WDG formulation resulted in higher weeds percent reduction of 77% and 69% respectively in comparison to the untreated check.
  • the percentage reduction of weeds by the composition is higher than the individual compounds as well as conventional combinations.
  • Table 8 Effect of pre-mix, metsulfuron-methyl 0.4% + clodinafop-propargyl 6% + metribuzin 21% oil-dispersion (OD) formulation and wettable powder (WP) formulation against major weeds in wheat variety HD 2967 at the Geong, Kaithal, Kamal and Chandigarh location in the Rabi season 2021.
  • OD oil-dispersion
  • WP wettable powder
  • the number of weeds were reduced to a greater extent (59.5 weeds/sq.mt area) that is at least 4 times in comparison to the untreated check (without herbicide treatment) (268.0weeds/sq.mt area).
  • compositions comprising metsulf iron- methyl, clodinafop-propargyl and metribuzin formulated into OD formulation resulted in more than 95% reduction of weeds in comparison to the untreated check.
  • the percentage reduction of weeds by the present composition is higher than the individual compounds as well as conventional combinations.
  • compositions comprising metsulfuron-methyl, clodinafop-propargyl and metribuzin formulated into WP formulation resulted in more than 87% reduction of weeds in comparison to the untreated check.
  • the percentage reduction of weeds by the composition is higher than the individual compounds as well as conventional combinations.
  • Table 10 Effect of pre-mix, metsulfuron-methyl 0.4% + clodinafop- propargyl 6% + metribuzin 21% oil-dispersion (OD) formulation and wettable powder (WP) formulation against major weeds in wheat variety HD 2967 at the Geong, Kaithal, Kamal and Chandigarh location in the Rabi season 2021.
  • Table 10 Effect of pre-mix, metsulfuron-methyl 0.4% + clodinafop- propargyl 6% + metribuzin 21% oil-dispersion (OD) formulation and wettable powder (WP) formulation against major weeds in wheat variety HD 2967 at the Geong, Kaithal, Kamal and Chandigarh location in the Rabi season 2021.
  • the number of weeds were reduced to a greater extent (50.83 weeds/sq.mt area) that is at least 6 times in comparison to the untreated check (without herbicide treatment) (315.17weeds/sq.mt area) .
  • compositions comprising metsulf iron- methyl, clodinafop-propargyl and metribuzin formulated into OD formulation resulted in more than 92% reduction of weeds in comparison to the untreated check.
  • the percentage reduction of weeds by the present composition is higher than the individual compounds as well as conventional combinations.
  • compositions comprising metsulfuron-methyl, clodinafop-propargyl and metribuzin formulated into WP formulation resulted in more than 89% reduction of weeds in comparison to the untreated check.
  • the percentage reduction of weeds by the composition is higher than the individual compounds as well as conventional combinations.
  • the present herbicide combination applied in a single treatment to the wheat crop kills substantially all of the weeds, thereby avoiding a need for successive treatments. It is also evident that the combination preparation in accordance with the present invention exhibits a superior herbicidal effect as compared to other known herbicidal products available in the market.

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  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
EP22804216.4A 2021-05-21 2022-05-20 Herbizidzusammensetzung und verfahren zu ihrer herstellung Pending EP4340620A1 (de)

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CA3029873A1 (en) * 2016-07-20 2018-01-25 Basf Se Herbicidal compositions comprising phenylpyrimidines
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