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EP3737232A1 - Compositions herbicides comportant une préparation de péthoxamide en suspension pour capsule - Google Patents

Compositions herbicides comportant une préparation de péthoxamide en suspension pour capsule

Info

Publication number
EP3737232A1
EP3737232A1 EP19702163.7A EP19702163A EP3737232A1 EP 3737232 A1 EP3737232 A1 EP 3737232A1 EP 19702163 A EP19702163 A EP 19702163A EP 3737232 A1 EP3737232 A1 EP 3737232A1
Authority
EP
European Patent Office
Prior art keywords
pethoxamid
herbicidal composition
safener
isocyanate
isoxadifen
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
EP19702163.7A
Other languages
German (de)
English (en)
Inventor
Paul Nicholson
Gurinderbir CHAHAL
Frank J. D'AMICO
Ubiratan F. DE SOUSA
Peter C. LAURSEN
Harald B. TEICHER
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.)
FMC Corp
Original Assignee
FMC Corp
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 FMC Corp filed Critical FMC Corp
Publication of EP3737232A1 publication Critical patent/EP3737232A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof

Definitions

  • This invention relates to herbicidal compositions comprising capsule suspensions of pethoxamid and optional safeners, and to methods for controlling weeds.
  • herbicidal compositions like herbicidal compositions, it is desirable in principle to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for herbicidal compositions to control harmful plants or weeds (commonly referred to herein as“weeds”) effectively, but at the same time not compromise crop safety. Also desirable is a broad spectrum of activity allowing the simultaneous control of weeds.
  • the herbicidal active compound pethoxamid is known from U.S. Patent 4,895,587 and is generally used to control grass and broad-leaved weeds such as foxtail species, crabgrass species, barnyardgrass, ladysthumb, bindweed, pigweed species, and common lambsquarters in various crops including corn, winter oil seed rape, soybeans, peas and beans, and tobacco.
  • pethoxamid has typically been formulated in emulsifiable concentrates, which have high levels of volatile organic compounds (VOCs) and may have undesirable crop injury due to higher uptake of herbicide by the useful plant.
  • VOCs volatile organic compounds
  • the emulsifiable concentrates also can exhibit poor performance on weeds when held for extended periods in a spray tank and may be difficult to reconstitute after exposure to cold temperatures.
  • US 2016/143281 Al discloses various formulations of pethoxamid and picloram, including capsule suspensions comprising pethoxamid in microcapsules prepared from a toluene diisocyanate/polymethylene -polyphenylisocyanate mixture and l,6-diaminohexane.
  • This invention relates to herbicidal compositions comprising a capsule suspension formulation of pethoxamid having reduced crop injury relative to conventional emulsifiable concentrate formulations of pethoxamid.
  • a herbicidal composition comprising a capsule suspension formulations of microencapsulated pethoxamid in which the pethoxamid is encapsulated in a shell of polyurea prepared from one or more amines selected from ethylenediamine, diethyl triamine, triethylenetetramine, l,6-hexanediamine, and mixtures thereof, and a polymeric isocyanate, such as polymethylene polyphenyl isocyanate, in the absence of toluene diisocyanate.
  • the capsule suspension formulations can be used to minimize injury ( ⁇ 10%) to desirable plants, while maintaining a satisfactory level of herbicidal activity against target weed species.
  • the polyurea is prepared in the absence of toluene diisocyanate, which forms a linear, more porous polymer structure for microcapsules.
  • herbicidal compositions with reduced oral toxicity and/or improved handler safety can be provided.
  • the invention also relates to herbicidal compositions in the form of a capsule suspension composition comprising a herbicidally effective amount of pethoxamid; and one or more safeners; and a liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for formulating crop protection agents.
  • the invention further relates to herbicidal compositions formulated as a capsule suspension composition comprising pethoxamid and one or more safeners wherein the pethoxamid and the safener(s) are combined in microcapsules, and a liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for formulating crop protection agents.
  • the invention still further relates to a product for preparing a herbicidal composition, comprising in a first container a capsule suspension formulation of pethoxamid, wherein pethoxamid is encapsulated in a shell of polyurea prepared from one or more amines selected from ethylenediamine, diethyl triamine, triethylenetetramine, l,6-hexanediamine, and mixtures thereof, and a polymeric isocyanate in the absence of toluene diisocyanate; and comprising in a second container a composition comprising one or more safeners and/or one or more second herbicides.
  • a product for preparing a herbicidal composition comprising in a first container a capsule suspension formulation of pethoxamid, wherein pethoxamid is encapsulated in a shell of polyurea prepared from one or more amines selected from ethylenediamine, diethyl triamine, triethylenetetramine, l,6-he
  • the capsule suspension formulations of pethoxamid are combined with one or more safeners, in particular wherein at least one safener (especially all safeners) are selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof.
  • at least one safener especially all safeners are selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof.
  • the invention further relates to a method for controlling weeds comprising exposing the weeds to a herbicidally effective amount of herbicidal composition as defined herein, or of a herbicidal composition prepared from the product defined herein.
  • the invention provides a method for controlling undesired plant growth comprises applying to the locus where such control is desired a herbicidally effective amount of herbicidal composition as defined herein, or of a herbicidal composition prepared from the product defined herein.
  • pethoxamid is used herein as an alternative or common name of 2-chloro- N-(2-ethoxyethyl)-N-(2-methyl-l-phenylprop-l-enyl)acetamide.
  • benoxacor is used herein as an alternative or common name of 4-(dichloroacetyl)-3,4-dihydro-3-methyl- 2H-l,4-benzoxazine.
  • diichlormid is used herein as an alternative or common name of N,N-diallyldichloroacetamide.
  • isoxadifen is used herein as an alternative or common name of 4,5-dihydro-5,5-diphenyl-l,2-oxazole-3-carboxylic acid or a salt thereof.
  • isoxadifen-ethyl is used herein as an alternative or common name of ethyl 4,5- dihydro-5, 5-diphenyl- l,2-oxazole-3-carboxylate.
  • weed means and includes any plant which grows where not wanted.
  • herbicide product refers to a compositional mixture that is produced, sold, or used in a field in order to kill or otherwise inhibit the growth of unwanted plants such as, but not limited to, deleterious or annoying weeds, broadleaf plants, grasses, and sedges; and can be used for crop protection, edifice protection or turf protection.
  • the term“herbicide product” includes the end-use herbicidal product. This composition can be a pure compound, a solution of chemical compounds, a mixture of chemical compounds, an emulsion, a suspension, a solid-liquid mixture, or a liquid- liquid mixture.
  • herbicide product also refers to the product that passes through the commercial channels from the manufacturer to the ultimate end user who can either apply the herbicide product to the affected field as sold, or suspend, dissolve or dilute the herbicide product, and/or mix it with other excipients and/or other herbicide products.
  • herbicidal composition refers to a herbicide product as defined above and in addition thereto to any composition that comprises one or more herbicidally active ingredients.
  • This composition can be a solution or a mixture like a suspension, dispersion, or powder.
  • the definition of the term“herbicidal composition” also refers to a product intended for use in manufacturing, or any product intended for formulation or repackaging into other herbicide products.
  • active ingredient refers to the specific compound or material that produces a biological effect, in particular a herbicidal effect against weeds, i.e. a“herbicide”, or that reduces or prevents plant damage from another active ingredient (e.g. a herbicide), i.e. a “safener”.
  • herbicidally effective amount denotes an amount of the herbicidal composition or of the combinations according to the invention, which is sufficient for providing one or more of the effects: (i) herbicidal activity, (ii) broader activity spectrum, or (iii) extended time frame, wherein a“herbicidal effect” on unwanted plant growth include one or more of the effects of necrosis, death, growth inhibition, reproduction inhibition, inhibition of proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity of unwanted plants.
  • the herbicidally effective amount is sufficient for to control weeds in the presence of useful plants while at the same time not resulting in unacceptable damage to the treated useful plants. Such an amount may be selected within a broad range and is dependent on various factors, such as the weed species to be controlled, the treated useful plant, the climatic conditions, soil conditions, and the specific combination used.
  • Control means to kill undesired plant(s), reduce or retard its growth or prevent or reduce its germination.
  • the plants to be controlled are weeds.
  • Weeds can also include plants which may be considered crop plants but which are growing outside a crop area (“escapes”), or which grow from seed left over from a previous planting of a different crop (“volunteers”). Such volunteers or escapes may be tolerant to certain other herbicides.
  • microcapsule refers to a generally spherical microparticle consisting of a polymeric shell comprising a wall-forming material and encapsulated active ingredient(s) located within the shell. This term is distinct from other spherical granules of the active substance dispersed in solvent or a polymer.
  • the microcapsules can comprise a single polymeric shell, wherein the active substance is located within the inner core or center of the microcapsule.
  • the microcapsules can also refer to a "multilayer microcapsule" comprising an inner core microcapsule and one or more outer polymeric shells.
  • the term“wall-forming polymer” refers to a polymer or polymerizable monomeric units or a combination of two or more different polymers or polymerizable monomeric units, which form a component of the polymeric shell of the microcapsules.
  • the term“polymer shell” refers to a layer containing the wall-forming polymer and, optionally, other components such as a plasticizer, oil, pore-forming components and/or a mineral.
  • pethoxamid and an additional active ingredient, such as a safener and/or a second herbicide, are contained in the same microcapsules.
  • a herbicidal composition comprising a capsule suspension formulation of pethoxamid, wherein pethoxamid is encapsulated in a shell of polyurea.
  • the polyurea is prepared from one or more amines selected from ethylenediamine, diethyltriamine, triethylenetetramine, l,6-hexanediamine, and mixtures thereof, and a polymeric isocyanate in the absence of toluene diisocyanate.
  • the herbicidal composition further comprises one or more safeners.
  • Suitable safeners may be those selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, cloquintocet-mexyl, cyometrinil, cyprosulfamide, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, mefenpyr-diethyl, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-l-oxa-4-azaspiro[4,5]decane (AD 67, CAS 71526-07-3), 4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid (CL 304,415, CAS 31541-57-8), 2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-
  • At least one safener is selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof, for example such that all safener(s) are selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof.
  • pethoxamid and the one or more safeners selected from benoxacor, dichlormid, isoxadifen and isoxadifen-ethyl, and combinations thereof are the sole active ingredients present in the herbicidal compositions, or in the products herein described and applied in the methods and uses herein described.
  • Pethoxamid is typically present in about 0.1% to about 60% by weight of the total herbicidal composition, such as from a lower limit of 0.1, 1, 5, 10, 20 or 30% by weight to an upper limit of 40, 45, 50 or 60% by weight of the total herbicidal composition.
  • the one or more safeners when present, are in total typically present in about 0.1 to about 10% by weight of the total herbicidal composition, such as from a lower limit of 0.1, 0.5, 1% by weight to an upper limit of 3, 5 or 10% by weight of the total herbicidal composition.
  • pethoxamid and the safener(s) are typically present in a weight ratio (pethoxamid:safener(s)) of in the range of 1:1 to 500:1, preferably 1:1 to 250:1, in particular 1: 1 to 150:1, particularly preferably 1:1 to 100:1, more preferably 2:1 to 70:1; even more preferably 10: 1 to 70:1 and most preferably 10:1 to 40:1, depending on the safener used.
  • the herbicidal compositions include those wherein the pethoxamid is encapsulated together with the safener(s) as described herein.
  • the herbicidal compositions include those wherein the pethoxamid is encapsulated as described herein, and the safener(s) is not encapsulated with the pethoxamid.
  • the herbicidal compositions comprise
  • pethoxamid as further described hereinabove
  • pethoxamid and at least one second herbicide are encapsulated together.
  • the second herbicide may be selected from isoxazolidinones such as clomazone, 2- (2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone or 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone; carotenoid biosynthesis inhibitors, for example beflubutamid (including optically enriched forms thereof), diflufenican, fluorochloridone, fluridone, isoxachlortole, ketospiradox, flurtamone, norflurazon or amitrole; auxin herbicides, for example pyridinecarboxylic acids, such as clopyralid, fluroxypyr, triclopyr or picloram; photosystem II inhibitors such as triazines such as atrazine, cyanazine, simazine, or terbuthylazine; HPPD inhibitors such as benzofenap, isoxaflutole,
  • the second herbicide comprises napropamide or napropamide-M. In another embodiment, the second herbicide comprises mesotrione. In another embodiment, the second herbicide comprises tembotrione. In still another embodiment, the second herbicide is beflubutamid.
  • the microcapsule may further comprise a safener, preferably selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof. For example, pethoxamid may be combined with triketones such as mesotrione, sulcotrione or tembotrione in the presence of isoxadifen or isoxadifen-ethyl.
  • the ratio of pethoxamid to the second herbicide in typically in the range of 1:50 to 50:1, preferably 1:10 to 10:1, or 1:5 to 5: 1, or 1:3 to 3:1, depending on the second herbicide used.
  • the weight ratio of pethoxamid and any safener is as otherwise described herein.
  • the herbicidal composition may further comprise at least one liquid carrier and/or one or more surfactants.
  • liquid carriers and/or surfactants are those being part of the capsule suspension formulation, e.g. those being included in the capsule suspension formulation upon the preparation of the microencapsulated pethoxamid as describe further below.
  • the herbicidal compositions typically comprise auxiliaries customary for formulating crop protection agents.
  • auxiliaries may include viscosity modifiers, preservatives, pH modifiers, antifreeze agents, colorants, and antifoam agents.
  • Viscosity modifiers are included to help prevent settling of the microcapsules and other suspended components.
  • Viscosity modifiers can include a wide variety of components including but not limited to glycerine, clays, gums, and modified cellulose derivatives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e.
  • high viscosity in the state of rest and low viscosity in motion include polysaccharides, such as carrageenan, xanthan gum, guar gum, gum Arabic, gum tragacanth, polyox, preferably xanthan gum such as Kelzan ® from Kelco or Rhodopol ® 23 (Rhone Poulenc), a magnesium aluminum silicate or smectite (bentonite and hectorite are members of the smectite group) such as Veegum ® (from R. T. Vanderbilt), or organic and inorganic sheet minerals, such as Attaclay ® (from Engelhardt).
  • the viscosity modifier may be present in about 0.01 to about 15% by weight of the total formulation preferably 0.1 to 5% by weight.
  • the viscosity of the final product may be adjusted to a measurement ranging from 200 and to 5000 Centipoises (mPas) with spindle #3, measured with Brookfield LVT Rotational Viscometer.
  • Suitable preservatives, biocides, bacteriocides and the like include but are not limited to C 12 to C 15 alkyl benzoates, alkyl p _ hydroxybenzoates, aloe vera extract, ascorbic acid, benzalkonium chloride, benzoic acid, benzoic acid esters of C 9 to C 15 alcohols, butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, castor oil, cetyl alcohols, chlorocresol, citric acid, cocoa butter, coconut oil, diazolidinyl urea, diisopropyl adipate, dimethyl polysiloxane, DMDM hydantoin, ethanol, ethylenediaminetetraacetic acid, fatty acids, fatty alcohols, hexadecyl alcohol, hydroxybenzoate esters, iodopropynyl
  • butylcarbamate isononyl iso-nonanoate, jojoba oil, lanolin oil, mineral oil, oleic acid, olive oil, parabens, poly ethers, polyoxypropylene butyl ether, polyoxypropylene cetyl ether, potassium sorbate, propyl gallate, silicone oils, sodium propionate, sodium benzoate, sodium bisulfite, sorbic acid, stearic fatty acid, sulfur dioxide, and derivatives, esters, salts and mixtures thereof.
  • bactericides examples include bactericides based on dichlorophen and benzyl alcohol hemiformal (Proxel ® from Lonza or Acticide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • Preservatives include sodium o-phenylphenate, 5-chloro-2-methyl-4-isothiazolin-3- one, 2-methyl-4-isothiazolin-3-one (Kathon ® ) and l,2-benzisothiazolin-3-one.
  • Suitable pH modifiers include acetic acid, hydrochloric acid, citric acid, phosphoric acid, buffers and the like.
  • antifreeze agents examples include ethylene glycol, propylene glycol, urea, glycerol, or water-soluble salts such as calcium chloride or sodium nitrate.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes.
  • examples include the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, and basic red 108.
  • the formulation of the invention may further contain an antifoam agent, and/or a pore-making agent.
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil ® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • the amounts of post-encapsulation additives to be added may be selected from one or more of 0.75 to 6.5% by weight of propylene glycol, 0.05 to 0.30% by weight of xanthan gum, 0.25 to 0.50% by weight of smectite clay, and 0.5 to 6.0% by weight of one or more surfactants, each weight percent relative to the weight of the formulation after addition of the stabilizers.
  • the herbicidal compositions according to the invention are also suitable for controlling vegetation on non-crop areas very efficiently, especially at high rates of application, and they act against broadleaf weeds and grass weeds (e.g. yellow nutsedge) in crops without causing any significant or unacceptable damage to the crop plants.
  • the herbicidal compositions further comprises one or more safeners and/or one or more second herbicides
  • one or more or all of such safener(s)/second herbicide(s) may be encapsulated together with pethoxamid, or one or more or all of such safener(s)/second herbicide(s) may be encapsulated separately by techniques described for the encapsulation of pethoxamid based on essentially the same materials, or one or more of all of such safener(s)/second herbicide(s) may be present in the herbicidal composition in non-encapsulated form, or in a separate composition in encapsulated or non-encapsulated form.
  • the polymer shell of the microcapsules comprising pethoxamid comprises an urea polymer made by isocyanate polymerization, wherein one or more isocyanates including a polymeric isocyanate react with one or more amines to form a polyurea.
  • the isocyanate molecules are usually contained within the oil phase in the processes described herein.
  • the amino groups may be generated in the oil phase or at the oil-water interface.
  • the polymerization is facilitated by a surface modifying compound that may react with the isocyanate moiety.
  • Suitable isocyanates include but are not limited to isomers and derivatives of biphenylene diisocyanates, polymeric isocyanates such as polymethylenepolyphenylene isocyanates (PMPPI), polymethylenepolyphenyl isocyanate containing 4,4'-methylene bisphenyl isocyanate, aliphatic acyclic isocyanates such as hexamethylene diisocyanate (HMDI), cyclic aliphatic isocyanates such as isophorone diisocyanate (IPDI) and trimers of HMDI, or mixtures thereof.
  • PMPPI polymethylenepolyphenylene isocyanates
  • HMDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • trimers of HMDI or mixtures thereof.
  • Amines that can react with the isocyanates to form polyureas may include ethylenediamine, diethyltriamine, triethylenetetramine, l,6-hexanediamine, or a mixture thereof.
  • the amine is l,6-hexanediamine (hexamethylene diamine).
  • polymers either biodegradable or non-biodegradable, may also be employed in the structure of the microcapsule shell. They include synthetic cellulose or other cellulose moieties such as cellulose acetate butyrate, cellulose acetate phthalate, carboxylethyl cellulose, cellulose triacetate, and cellulose sulfate sodium salt, polymers of acrylic acid, methacrylic acid or copolymers or derivatives thereof including esters, poly(methyl methacrylate), poly(ethyl methacrylate), poly (butylmethacry late), poly(isobutyl
  • non-biodegradable polymers examples include ethylene vinyl acetate,
  • biodegradable polymers include polymers of hydroxy acids such as lactic acid and glycolic acid polylactide, polyglycolide, polylactide co glycolide, and copolymers with PEG, poly anhydrides, poly(ortho)esters, polyurethanes, poly(butyric acid), poly(valeric acid), and poly(lactide-co-caprolactone).
  • the microcapsules of the invention are designed to may be sufficiently robust or to be dried and then re-dispersed.
  • the weight ratio of the wall material to the microcapsule is greater than 1% by weight.
  • the weight ratio of the wall material to the microcapsule will be from 1 % to 70%, such as from a lower limit of 1, 3, or 5% by weight to an upper limit of 10, 15, 20,
  • microcapsules comprising pethoxamid included in the herbicidal compositions according to this invention may be prepared by any of the known microencapsulation techniques.
  • a relatively water-insoluble (generally termed an "organic” or “oil”) liquid phase is prepared that contains pethoxamid and optionally one or more additional herbicides, and/or optionally one or more safeners, optionally dissolved or suspended in a solvent, optionally one or more surfactants and one or more monomers that will become polymerized to form a polymeric shell for the capsule.
  • the organic phase is then added to an aqueous phase with agitation, forming a dispersion or emulsion of organic (discontinuous) phase droplets in the aqueous (continuous) phase.
  • the aqueous phase may contain one or more surfactants, protective colloids, and other ingredients as known in the art.
  • the dispersion is then subjected to conditions (usually agitation and heating) so as to cause the monomer or monomers contained in the organic phase droplets to polymerize at the interface between the organic and aqueous phases, forming shells of polymer around the droplets.
  • the result is a suspension of microcapsules in the aqueous phase.
  • This suspension may be suitable for application to the locus to control undesirable vegetation, or it may be modified by additional agriculturally suitable formulants prior to application.
  • the reaction leading to the formation of the polymeric shell is initiated by heating the emulsion to an elevated temperature at which point some isocyanate groups are hydrolyzed at the interface to form amines, which in turn may react with unhydrolyzed isocyanate groups to form the polyurea microcapsules.
  • diamines and/or polyamines are added to the emulsion, which then react with the isocyanates to form the polyurea microcapsule.
  • the capsule suspension can be prepared by a process involving the following steps: (a) providing an aqueous phase containing an emulsifier, preferably a partially hydrolyzed polyvinyl alcohol; and optionally at least one of an antifoam agent, or a viscosity modifier/stabilizer such as xanthan gum, or other water soluble formulant; (b) providing a water immiscible phase comprising pethoxamid, polymerizable isocyanate such as polymeric isocyanates such as polymethylenepolyphenyleneisocyanates (PMPPI), polymethylene polyphenyl isocyanate containing 4,4' methylene bisphenyl isocyanate, and optionally a safener selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof, with or without a hydrocarbon solvent or water-insoluble carrier; (c) emulsifying the water immiscible phase in
  • the polyurea is prepared in the absence of toluene diisocyanate, which forms a linear, more porous polymer structure for
  • the suspension is cured by moderate heating, after which one or more stabilizing agents, such as propylene glycol, xanthan gum, smectite clay, or an ionic dispersing agent such as a sulfonate of an alkyl napthalene, may be added.
  • stabilizing agents such as propylene glycol, xanthan gum, smectite clay, or an ionic dispersing agent such as a sulfonate of an alkyl napthalene.
  • the shell wall of the microcapsules is a polyurea formed via the emulsion polymerization process.
  • the aqueous phase may contain 0.3 to 3.0%, preferably 0.8 to 2.0%, by weight of one or more emulsifiers, e.g., polyvinyl alcohol, 0.05 to 0.20%, preferably 0.06 to 0.15%, by weight of the xanthan gum viscosity modifier/stabilizer, if it is used, and 0.1 to 1.0%, preferably 0.4 to 0.9%, by weight of an antifoam agent, if it is used.
  • one or more emulsifiers e.g., polyvinyl alcohol
  • 0.05 to 0.20% preferably 0.06 to 0.15%
  • the xanthan gum viscosity modifier/stabilizer if it is used
  • 0.1 to 1.0% preferably 0.4 to 0.9%
  • the water-immiscible phase may comprise 60 to 85%, preferably 65 to 80%, by weight of pethoxamid, an amount of polymeric isocyanate such that the weight ratio of pethoxamid to isocyanate is in the range of 1: 1 to 20:1, preferably 3: 1 to 15:1, and optionally a solvent, such as an aromatic hydrocarbon solvent, for the two solutes.
  • a solvent such as an aromatic hydrocarbon solvent
  • Solvents or carriers include any non-aqueous solvents that are capable of suspending or dissolving pethoxamid, but not chemically react with pethoxamid.
  • liquid carriers or solvents examples include vegetable oils such as, soybean oil, epoxidized soybean oil, coconut oil, olive oil, safflower oil, cotton seed oil, corn oil, rape seed oil and the like, mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, or coal tar oils.
  • liquids include aliphatic, cycloaliphatic, or aromatic hydrocarbons such as dodecane, n-decane, n-hexane, cyclohexane, toluene, benzene, and the like for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives; aliphatic or aromatic alcohols such as heptanol, octanol, and the like, ketones such as cyclohexanone, or combinations of any two or more thereof.
  • suitable solvents include petroleum distillates, such as heavy aromatic naphthalene-depleted solvents (Aromatic 200, 100, 150) having a boiling point in the range of 100-400 °C.
  • the amine solution will ordinarily contain 10 to 100%, preferably 30 to 50%, by weight of ethylenediamine, diethylenetriamine, triethylenetetramine, l,6-hexanediamine, or optionally a mixture of the polyfunctional amines, with ethylenediamine being used only in a mixture.
  • a preferred amine is l,6-hexanediamine (hexamethylene diamine).
  • the polymerization reaction is allowed to proceed so as to form a microcapsule wall thickness that is suitable for the present intended purpose.
  • altering the concentration of the polymeric isocyanate in the oil phase and its respective ratio to the amine moiety can lead to different wall thickness.
  • the wall thickness of the resulting microcapsules is much less compared to a scenario wherein the isocyanate is present in amount of 7.5% in the oil phase, with the same aminedsocyanate ratio.
  • altering the aminedsocyanate ratio impacts the final wall thickness. Any such alterations unexpectedly lead to unique physical and physiochemical properties of such microcapsules that are customized towards active ingredients of choice.
  • the microcapsules are prepared in such manner to provide a microcapsule shell thickness ranging from 5 nanometers to 1000 nanometers.
  • the microcapsule has a shell wall thickness ranging from 10 to 200 nanometers, alternatively 15-100 nanometers resulting in microcapsules thereby reducing the amount of buildup on the treating equipment.
  • the microcapsules are prepared following the general steps of (1) making an organic phase by mixing pethoxamid and optionally an additional active ingredient (like safener(s) and/or second herbicide(s)) with the isocyanate monomers, optional solvents/oils, and other additives; (2) making an emulsion of the organic phase in an aqueous phase by using selected surfactants; (3) adding the amine monomers to activate interfacial polymerization; (4) and allowing interfacial polymerization for a sufficient amount of time, preferably between 5-24 hours at a preset temperature and pH 2-5.
  • interfacial polymerization occurs at a temperature ranging from 25 to 65 °C. In a more preferred embodiment, the interfacial polymerization occurs at a temperature ranging from 45 to 60 °C.
  • the emulsification step requires high shear mixing to give small droplets of the immiscible oil phase in the aqueous phase.
  • Factors that influence droplet size include speed and length of mixing, the type and amount of surfactant, solvent, temperature, and viscosity, as well as the xanthan gum when used. Selection of the appropriate microcapsule size to achieve the purposes of the invention requires a balance between competing factors. In general, increasing microcapsule size decreases volatility, but also decreases suspensibility of the particles, while decreasing size yields better suspensibility, but higher volatility.
  • the average size of the microcapsules is 5 to 50 microns, preferably 5 to 30 microns.
  • the operating conditions to yield microcapsules of a desired size will depend on the emulsifying equipment used, and the adjustment to determine the proper conditions is well within the skill of the art.
  • agitation during the amine addition should be gentle. Stirring is continued while the suspension is cured by heating to a temperature of 35 to 60, preferably 45 to 50 °C, for 3 to 10, or preferably 4 to 5, hours.
  • Emulsifiers include water-soluble polymers or surfactants.
  • water-soluble polymer in the process in which the microcapsules are formed, as polyvinyl alcohol and some other polymers are known to be useful, for instance, as protective colloids or co-surfactants to enhance the stability of the oil-in- water emulsion.
  • the amount of water-soluble polymer for this purpose should be kept relatively low, preferably about 5% by weight or less, more preferably no more than 2 to 3% by weight of the total formulation.
  • the water-soluble polymer may either be added to the suspension of microcapsules after the microcapsules have been formed, or may be initially added in the aqueous phase during the formation of the dispersion and the resulting microcapsules.
  • the amount of water-soluble polymer utilized is toward the higher end (from about 5 to about 15% by weight) or is a more viscous material, it must be added to an already prepared suspension of microcapsules, and should not be present in the microcapsule production process, as it may be too viscous for a good emulsion to form or may interfere with the production of the capsule shell walls.
  • the water-soluble polymers usable in this invention include both synthetic and natural polymers such as polyvinylpyrrolidone, polyvinyl alcohol, polyethylene oxides,
  • a preferred water- soluble polymer comprises polyvinyl alcohol.
  • Polyvinyl alcohols are obtained by hydrolysis of polyvinyl acetates and are usually sold in solid form, in a number of variations of molecular weight and degree of hydrolysis. In general, polyvinyl alcohol of lower molecular weight and/or lesser degree of hydrolysis tends to be more water-soluble. For instance, partially hydrolyzed polyvinyl alcohols (e.g., up to about 89-90% hydrolyzed) tend to be more water soluble and thus preferred for use in this invention.
  • the solid polyvinyl alcohols are used in this invention by dissolving them in water to form solutions.
  • surfactants such as dispersants, protective colloids, emulsifiers, wetting agents
  • surfactants can be used to emulsify the water-immiscible components in the aqueous phase.
  • Suitable surfactants include nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts.
  • Suitable surfactants include the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borresperse types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF AG), and of fatty acids, alkyl, aryl or alkylaryl sulfonates, alkyl, aryl or alkylaryl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde,
  • methylcellulose methylcellulose
  • hydrophobic ally modified starches polycarboxylates (BASF AG, Sokalan types), polyalkoxylates, polyvinylamine (BASF AG, Lupamine types), polyethyleneimine (BASF AG, Lupasol types), polyvinylpyrrolidone and copolymers thereof and mixtures thereof.
  • Notable surfactants include lignin sulfonates such as sodium lignosulfate, commercially available under the Reax ® , Polyfon ® or Kraftsperse ® tradenames.
  • the formulation of the invention contains pore-forming material that would facilitate permeation of the herbicide out of the microcapsules.
  • the polymeric shell may be crosslinked by inclusion of additional monomers capable of reacting with the isocyanates such as amines or alcohols with three or more functional groups.
  • Cross-linking may be accomplished by the inclusion of a cross-linker such as polyvinyl alcohol.
  • the microcapsules comprising pethoxamid typically have a diameter ranging from 0.1 micron to 500 microns.
  • the capsule suspension formulation comprises a plurality of microcapsules, wherein at least 90% of one population of microcapsules has an effective particle size ("D90") of less than about 500 microns; in another embodiment D90 is less than about 100 microns, and yet in another embodiment, D90 is up to or less than 20, 18, 15, or 10 microns.
  • the microcapsule population has a particle size defined by D90 of between about 1 and about 7 microns, preferably between 2-6 microns.
  • formulation process may include the addition and formulation by conventional techniques of safener(s), second herbicide(s), and one or more further auxiliaries customary for formulating crop protection agents so as to arrive at the herbicidal composition.
  • the invention also provides a product for preparing a herbicidal composition, comprising in a first container a capsule suspension formulation of pethoxamid, wherein pethoxamid is encapsulated in a shell of polyurea prepared from one or more amines selected from ethylenediamine, diethyl triamine, triethylenetetramine, 1,6 hexanediamine, and mixtures thereof, and a polymeric isocyanate in the absence of toluene diisocyanate; and comprising in a second container a composition comprising one or more safeners and/or one or more second herbicides.
  • the herbicidal composition may be presented as a product comprising two compositions which can be mixed, e.g. tank-mixed, to the ready-to-use herbicidal composition shortly before or immediately before use.
  • the components of the product according to the invention can be used individually or already partially or completely mixed with one another to prepare the herbicidal composition according to the invention. It is also possible for them to be packaged as a kit of two compositions and used later in time such as by combining the composition to form a herbicidal composition for application, or by applying the compositions separately and sequentially to the same locus.
  • the product may comprise - in the first container - the capsule suspension formulation comprising pethoxamid including a liquid carrier and/or one or more surfactants; and - in the second container - a composition comprising the safener(s) and/or second herbicide(s) and a solid or liquid carrier and/or one or more surfactants.
  • the product may comprise - in the first container - the capsule suspension formulation comprising pethoxamid and one or more safeners and including a liquid carrier and/or one or more surfactants, for example such that pethoxamid and the safener(s) are encapsulated together; and - in the second container - a composition comprising the one or more second herbicides and a solid or liquid carrier and/or one or more surfactants.
  • the product may comprise - in the first container - the capsule suspension formulation comprising pethoxamid and one or more second herbicides and including a liquid carrier and/or one or more surfactants for example such that pethoxamid and the second herbicide(s) are encapsulated together; and - in the second container - a composition comprising the one or more safeners and a solid or liquid carrier and/or one or more surfactants.
  • formulations/compositions may further comprise further auxiliaries customary for formulating crop protection agents, as described hereinabove for the herbicidal compositions.
  • the product may include one or more, including all, components that may be used to prepare a subject herbicidal composition.
  • kits may include encapsulated pethoxamid and optionally one or more herbicide component(s) and/or a formulant component and/or a safener component.
  • One or more of the components may already be combined together or pre-formulated.
  • the components may already be combined together and as such are packaged in a single container such as a vial, bottle, can, pouch, bag, or canister.
  • two or more components of a kit may be packaged separately, i.e. not pre-formulated.
  • kits may include one or more separate containers such as vials, cans, bottles, pouches, bags or canisters, each container containing a separate component for a herbicidal composition.
  • a component of the kit may be applied separately from or together with the further components or as a component of a combination according to the invention for preparing the herbicidal composition according to the invention.
  • the invention also relates to a method of controlling plants, in particular weeds, which comprises applying to the plants or to the locus thereof a herbicidal composition as defined herein.
  • “Locus” means the area in which the plants are growing or will grow.
  • the invention provides a method for controlling weeds comprising exposing the weeds to a herbicidally effective amount of herbicidal composition as defined herein, or of a herbicidal composition prepared from the product defined herein.
  • the invention in particular relates to a method for the selective control of weeds in areas where useful plants like crops are growing or will grow.
  • the invention provides a method for controlling undesired plant growth comprises applying to the locus where such control is desired a herbicidally effective amount of herbicidal composition as defined herein, or of a herbicidal composition prepared from the product defined herein.
  • the invention also relates to a method of inhibiting plant growth which comprises applying to the plants or to the locus thereof a herbicidal composition according to this invention.
  • the methods according to the invention are particularly interesting where the weed or weeds to be controlled are present together with useful plants.
  • the herbicidal composition to be applied preferably comprises one or more safeners to reduce injury to useful plants, e.g. as described hereinabove for the herbicidal compositions according to the invention.
  • at least one safener is selected from benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl, and combinations thereof.
  • the rates of application of the compounds contained in the herbicidal composition vary within wide limits and depend on the nature of the soil (for instance, texture, organic matter etc.), the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • Useful plants in which the herbicidal composition according to the invention can be used include crops such as cereals (for example barley, wheat, corn (maize) or rice), cotton, oilseed rape, soybeans, sugar beet, and sugar cane. Crop plants can also include trees, such as fruit trees, palm trees, coconut trees or other nuts, vines such as grapes, fruit bushes, fruit plants and vegetables.
  • crops such as cereals (for example barley, wheat, corn (maize) or rice), cotton, oilseed rape, soybeans, sugar beet, and sugar cane.
  • Crop plants can also include trees, such as fruit trees, palm trees, coconut trees or other nuts, vines such as grapes, fruit bushes, fruit plants and vegetables.
  • the method for controlling unwanted or undesired vegetation comprises application of a composition as herein described, in particular where crop plants are cultivated, for example in crops of the following crop plants: 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.
  • Theobroma cacao Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays, especially crops of cereals, com, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, sunflower or permanent crops, and also in crops which are resistant to one or more herbicides or to attack by insects owing to genetic engineering or breeding.
  • herbicidal compositions according to the invention may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.
  • the herbicidal compositions according to the invention can also be used in crops which tolerate insects or fungal attack as the result of breeding, including genetic engineering methods.
  • the application is generally made by spraying the herbicidal composition, typically by tractor mounted sprayer for large areas, but other methods such as drip or drench can also be used.
  • the user may also apply the herbicidal composition according to the invention usually from a pre-dosage device, a backpack sprayer, a spray tank, or a spray plane.
  • the herbicidal composition is made up with water and/or buffer to the desired application concentration, it being possible, if appropriate, to add further auxiliaries, and the ready-to-use spray liquor or the herbicidal composition according to the invention is thus obtained.
  • the pethoxamid and the safener(s) and/or second herbicides can be applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants i.e. both the useful plants and/or weeds.
  • pethoxamid is presented in a herbicidal composition as defined herein, whereas the safener(s) may be present in the herbicidal composition together with pethoxamid, or may be present in a separate composition.
  • any second herbicide(s) may be present in the herbicidal composition together with pethoxamid, or may be present in a separate herbicidal composition.
  • the order of the application of pethoxamid and the safener is of minor importance. The only thing that is important is that pethoxamid and the safener are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the useful plant to be controlled.
  • pethoxamid and the safener are included in the same composition or tank mix, they are applied jointly and simultaneously.
  • the required application rate of active compound composition i.e.
  • pethoxamid and the safener(s) depends on the composition of the plant stand, on the development stage of the plants, on the climatic conditions at the site of use and on the application technique.
  • the combined application rate of pethoxamid and the safener(s) is in the range of 0.05 to 5 kg/ha, or in the range of 0.05 to 3 kg/ha, preferably 0.06 to 3 kg/ha, and in particular 0.1 to 2.5 kg/ha, of active ingredients.
  • the required application rates of pethoxamid are generally in the range of 0.05 to 5 kg/ha, or 0.05 to 2.5 kg/ha, and preferably 0.1 to 2.5 kg/ha, of active ingredient (a.L).
  • the required application rates of safener e.g. benoxacor, dichlormid, isoxadifen, isoxadifen-ethyl or a combination thereof, are generally in the range of 0.001 to 1 kg/ha, or 0.001 to 0.5 kg/ha, preferably 0.005 to 0.3 kg/ha, and in particular 0.01 to 0.1 kg/ha.
  • pethoxamid and the safener(s), if present, are typically applied in a weight ratio (pethoxamid:safener(s)) of in the range of 1:1 to 500:1, preferably 1:1 to 250:1, in particular 1:1 to 150:1, particularly preferably 1:1 to 100: 1, more preferably 2:1 to 70: 1; even more preferably 10:1 to 70:1 and most preferably 10:1 to 40: 1, depending on the safener used.
  • pethoxamid and the safener(s) are typically applied in a weight ratio (pethoxamid:safener(s)) of in the range of 1:1 to 500:1, preferably 1:1 to 250:1, in particular 1:1 to 150:1, particularly preferably 1:1 to 100: 1, more preferably 2:1 to 70: 1; even more preferably 10:1 to 70:1 and most preferably 10:1 to 40: 1, depending on the safener used.
  • the herbicidal compositions are applied to the plants mainly by spraying the leaves of the plant or the locus of the plant, such as the soil surrounding the plant.
  • the application can be carried out using, for example, water as a carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 L/ha (for example from 300 to 400 L/ha).
  • the herbicidal compositions may also be applied by the low- volume or the ultra-low- volume method.
  • the herbicidal composition comprising pethoxamid and safener can be applied pre-, early post, or post-emergence.
  • the safener and agriculturally acceptable derivatives thereof are recommended to be applied post-emergence of the weeds to provide a herbicidal effect and pethoxamid recommended for pre-emergence of the weeds. This is advantageous since it broadens the time where the combination effectively controls emerging weeds.
  • the herbicidal compositions are applied early post-emergence.
  • Example 1 The formulations of the invention were prepared by the methods exemplified in the following Examples.
  • Example 1 The formulations of the invention were prepared by the methods exemplified in the following Examples.
  • Example 1 The formulations of the invention were prepared by the methods exemplified in the following Examples.
  • Example 1 The formulations of the invention were prepared by the methods exemplified in the following Examples.
  • Example 1 The formulations of the invention were prepared by the methods exemplified in the following Examples.
  • a microcapsule suspension was prepared using the materials summarized in Table 1 according to the general procedure below.
  • SolvessoTM Aromatic a mixture of C 9 -C 15 aromatic, naphthalene- solvent 45 200ND (ExxonMobil) depleted hydrocarbons, flash-point 200 °C
  • Naphthalene sulfonate condensate (BASF) dispersing agent Naphthalene sulfonate condensate (BASF) dispersing agent
  • TX 1520 Dow Coming 20% silicone emulsion antifoam agent 4 aqueous solution of 1, 2-benzisothiazolin-3
  • aqueous 24% polyvinyl alcohol solution (Celvol ® 24-203), antifoam agent and naphthalene sulfonate formaldehyde condensate and 250.0 grams of water.
  • a pre-blended solution of pethoxamid, PAPI ® 2027, and petroleum solvent (Aromatic 200 ND) was added, and the mixture was emulsified in the high shear mixer for 10 to 20 seconds. The shear rate was reduced and the aqueous solution of HMDA was added in a steady stream.
  • Example 2 was prepared as described in the following. In a one-liter stainless steel beaker were placed Reax ® 88B (sodium lignosulfonate) and 228.0 grams of water. After this mixture was mixed for 10-20 seconds at low speed in a high-shear mixer, a pre-blended solution of pethoxamid, PAPI ® 2027, and petroleum solvent (Aromatic 200 ND) was added, and the mixture was emulsified in the high shear mixer for 10-20 seconds. After a homogeneous emulsion was obtained, the shear rate was reduced and HMDA was added in a steady stream.
  • Reax ® 88B sodium lignosulfonate
  • Example 3 was prepared similarly to Example 1.
  • Examples 4 and 5 include either benoxacor or dichlormid as safeners and are summarized in Table 3. Table 3
  • Example 4 was prepared according to the following procedure.
  • Example 5 was prepared as in Example 4, except dichlormid was used instead of benoxacor.
  • the mixture was then placed in a one-liter jacketed resin flask with the jacket pre-heated to 50 °C.
  • the mixture was stirred at a moderate speed with an air-powered stirrer.
  • the mixture was then stirred at 50 °C for four hours.
  • sodium nitrate was added to the mixture and allowed to dissolve completely.
  • the formulation was then stirred for about one hour and stored for later use.
  • xanthan gum and a preservative were added after the microencapsulation process was complete to provide a stable matrix for the composition.
  • Capsule suspensions comprising isoxadifen or isoxadifen-ethyl coencapsulated with pethoxamid can be prepared similarly.
  • capsule suspensions of pethoxamid plus a second herbicide such as clomazone, 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone, mesotrione, tembotrione or napropamide may be prepared similarly.
  • a mixture of clomazone, 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone, mesotrione, tembotrione or napropamide may be prepared similarly.
  • pethoxamid and the selected second herbicide, PAPI ® 2027, and solvent (such as Aromatic 200 ND) is preblended, then added to a mixture of water, surfactant and polyvinyl alcohol.
  • the mixture is emulsified in the high shear mixer for a brief period, such as 10-20 seconds.
  • the shear rate is reduced and an aqueous solution of HMDA is added in a steady stream.
  • the mixture is then placed in a one-liter jacketed resin flask with the jacket pre -heated to 50 °C.
  • the mixture is stirred at a moderate speed with an air-powered stirrer until curing is complete, for example for four hours.
  • additional formulant(s) may be added such as an antifreeze component, xanthan gum and/or a preservative to the mixture.
  • the formulation is then stirred for about one hour and stored for later use.
  • Comparative Example Cl is a 60% emulsifiable concentrate of pethoxamid, available commercially under the tradename Successor ® .
  • Comparative Example C2 is an emulsifiable concentrate of 82.4% of S-metolachlor blended with benoxacor, available commercially under the tradename Dual II Magnum ® .
  • compositions of the Examples were tested for storage stability at temperatures of -10 °C, +40 °C and +50 °C for up to twelve weeks and demonstrated good thermal stability in those tests.
  • the capsule suspensions were treated under cold conditions, the microcapsules stayed in suspension and could be easily reconstituted by gentle shaking.
  • Comparative Example Cl is an emulsifiable concentrate containing S-metolachlor safened with benoxacor, which provided excellent weed control with low phytotoxicity on corn at 560 and 1120 g a.i./ha.
  • Example 4 provided very similar levels of phytotoxicity and weed control compared to C2.
  • Example 5 provided somewhat higher levels of phytotoxicity but similar weed control compared to C2.

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Abstract

La présente invention concerne des compositions herbicides qui comportent une préparation de péthoxamide micro-encapsulé en suspension pour capsule, le péthoxamide étant encapsulé dans une enveloppe de polyurée préparée à partir d'une ou de plusieurs amines sélectionnées parmi l'éthylènediamine, la diéthyltriamine, la triéthylènetétramine, la 1,6-hexanediamine et leurs mélanges, et un isocyanate polymère en l'absence de diisocyanate de toluène, éventuellement combiné avec un phytoprotecteur tel que le bénoxacor, le dichlormide, l'isoxadifène, l'isoxadifène-éthyle ou des combinaisons de ceux-ci. La présente invention concerne également des procédés de lutte contre la végétation indésirable telle que les plantes adventices.
EP19702163.7A 2018-01-12 2019-01-11 Compositions herbicides comportant une préparation de péthoxamide en suspension pour capsule Pending EP3737232A1 (fr)

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AR130626A1 (es) * 2022-09-30 2024-12-18 Fmc Corp Mezclas de bixlozona con petoxamida
WO2024243119A2 (fr) * 2023-05-19 2024-11-28 Spectrum Solutions L.L.C. Produits et méthodes de conservation et de détection de biomolécules dans des échantillons de salive humaine

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EP0206251A1 (fr) * 1985-06-21 1986-12-30 Tokuyama Soda Kabushiki Kaisha Composés haloacétamide, prodédé pour leur production et leur usage comme herbicide
EP2395843A2 (fr) * 2009-02-13 2011-12-21 Monsanto Technology LLC Encapsulation de desherbants permettant de reduire les dommages causes a des cultures
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MARK L BERNARDS ET AL: "Inbred Corn Response to Acetamide Herbicides as Affected by Safeners and Microencapsulation", WEED TECHNOLOGY, vol. 20, 1 April 2006 (2006-04-01), pages 458 - 465, XP055581068, DOI: 10.1614/WT-05-130R.1 *
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