WO2001087064A1 - Traitement de pulverisation agrochimique et preparations a pulveriser - Google Patents

Traitement de pulverisation agrochimique et preparations a pulveriser Download PDF

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Publication number
WO2001087064A1
WO2001087064A1 PCT/GB2001/002052 GB0102052W WO0187064A1 WO 2001087064 A1 WO2001087064 A1 WO 2001087064A1 GB 0102052 W GB0102052 W GB 0102052W WO 0187064 A1 WO0187064 A1 WO 0187064A1
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WIPO (PCT)
Prior art keywords
agrochemicai
concentrate
formulation
water
emulsion
Prior art date
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PCT/GB2001/002052
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English (en)
Inventor
Johan Camiel Gabrielle Rommens
Youry Den Tandt
Original Assignee
Imperial Chemical Industries Plc
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Filing date
Publication date
Priority claimed from GB0011605A external-priority patent/GB0011605D0/en
Application filed by Imperial Chemical Industries Plc filed Critical Imperial Chemical Industries Plc
Priority to EP01928095A priority Critical patent/EP1408748A1/fr
Priority to AU2001254961A priority patent/AU2001254961A1/en
Publication of WO2001087064A1 publication Critical patent/WO2001087064A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

Definitions

  • This invention relates to the treatment of plants, in particular to the treatment of plants with formulations including certain esters in combination with surfactants and especially to such treatment where the formulations also contain agrochemicals; to agrochemicai formulations in particularly to formulations in which an agrochemicai is dissolved in an ester as solvent or carrier fluid.
  • Carrier fluids or solvents are used in crop protection applications as solvents for formulation components, particularly agrochemicals, particularly in concentrate formulations (for dilution usually in water prior to use) and as adjuvants i.e. materials that are not themselves agrochemicaliy active, but enhance the activity of an agrochemicai, in particular as crop oils, tank mix additives or built into concentrate agrochemicai formulations.
  • carrier fluids or solvents include aromatic hydrocarbons such as xylene and mineral oils, particularly those containing aromatic hydrocarbons such as the “Solvesso” (Exxon Chemicals) and “Shellsol” (Shell Chemicals) ranges and aliphatic and paraffinic solvents such as the “Exxsol” and “Isopar” (Exxon Chemicals) ranges.
  • the present invention is based on the discovery that certain esters of aromatic carboxylic acids, particularly benzoic acid, can be used very effectively in the treatment of plants and in particular as carrier fluids and/or solvents for agrochemicals.
  • agrochemicai is used to refer to agrochemicaliy active compounds and materials.
  • carrier fluids and/or solvents are environmentally much less objectionable than the largely aromatic hydrocarbon materials used currently.
  • the present invention accordingly provides a method of treating plants, in which a composition including at least one compound of the formula (I):
  • R 1 is a C ⁇ to C20 alkyl or alkenyl group, particularly a C-j to C- ⁇ g, more particularly a C-] to Cg alkyl group, especially a C3 to C5 branched alkyl group;
  • AO is an alkyleneoxy group, particularly an ethyleneoxy or a propyleneoxy group, and may vary along the (poly)alkyleneoxy chain; n 0 or from 1 to 100, desirably 0; m is 0, 1 or 2, desirably 0; and Ph is a phenyl group, which may be substituted with groups (R 2 ) p ; where each R 2 is independently a C-( to C4 alkyl or alkoxy group; and p is 0, 1 or 2, desirably 0; together with at least one surfactant and/or an agrochemicai, is sprayed onto the plant or onto the immediate environment of the plant.
  • the method of the invention includes a method of treating plants, particularly fruit trees r .by spraying onto the plants a formulation of a carrier fluid including at least one compound of the formula (I) as defined above; at least one surfactant; and optionally also including at least one agrochemicai, particularly a pesticide, especially an insecticide, desirably dissolved in the carrier.
  • the method of the invention further includes a method of treating plants by spraying onto the plants a formulation which is an aqueous emulsion of a carrier fluid which includes at least one compound of the formula (I) as defined above; at least one agrochemicai; and at least one surfactant. Desirably one or more agrochemical(s) is(are) dissolved in the carrier fluid.
  • the invention includes an agrochemicai formulation which includes a carrier fluid including at least one compound of the formula (I); at least one agrochemicai; and at least one surfactant.
  • agrochemicai formulation of the invention desirably at least one of the agrochemical(s) and/or surfactant(s) is dissolved in the carrier fluid, although some materials, agrochemical(s) and/or surfactant(s) and/or other components, may be dispersed in the formulation (in the carrier fluid or other liquid phase components).
  • the carrier fluid may be the major liquid phase of the formulation or it may be emulsified in water.
  • the formulation may thus take the form of solutions, particularly solution concentrates, emulsions, including emulsion concentrates, emulsifiable concentrates, suspensions, oil based suspension concentrates, suspoemulsion concentrates, microemulsions, multiple emulsions, and spray formulations obtained by diluting concentrated formulations, particularly to give solutions, emulsions, suspensions (dispersions) , suspoemulsions, microemulsions or multiple emulsions.
  • solutions particularly solution concentrates, emulsions, including emulsion concentrates, emulsifiable concentrates, suspensions, oil based suspension concentrates, suspoemulsion concentrates, microemulsions, multiple emulsions, and spray formulations obtained by diluting concentrated formulations, particularly to give solutions, emulsions, suspensions (dispersions) , suspoemulsions, microemulsions or multiple emulsions.
  • the invention specifically includes agrochemicai formulations in the form of one of: a an oil in water emulsion of a solution of at least one agrochemicai in a water immiscible liquid which is or includes at least one compound of the formula (I); and b a water in oil emulsion in which the continuous phase is a solution of at least one agrochemicai in a water immiscible liquid which is or includes at least one compound of the formula (I).
  • the invention also includes: c an emulsifiable concentrate, which is typically diluted with water to form an oil in water emulsion before use, in which at least one agrochemicai is dissolved in a carrier fluid which is or includes at least one compound of the formula (I) and which further includes in solution or dispersion at least one emulsifier surfactant and desirably includes at least one adjuvant surfactant; d an oil based suspension concentrate, which is typically diluted with water to form a suspension (dispersion) of an agrochemicai when diluted in water before use, in which at least one agrochemicai is dispersed in a carrier fluid which is or includes at least one compound of the formula (I) and which further includes in solution or dispersion at least one dispersant surfactant and desirably includes at least one adjuvant surfactant; e a suspoemulsion concentrate (commonly in the art simply referred to as a "suspoemulsion”), which is typically
  • the invention further includes diluted versions of the above formulations, usually diluted with water.
  • the invention also includes a method of treating vegetation in which the vegetation is sprayed by a formulation of the invention, particularly a diluted formulation, particularly in the form of an oil in water emulsion or a water in oil emulsion, and/or particularly a diluted emulsifiable concentrate, a diluted suspension concentrate, a diluted suspoemulsion, a diluted microemulsion and/or a diluted multiple emulsion.
  • a formulation of the invention particularly a diluted formulation, particularly in the form of an oil in water emulsion or a water in oil emulsion, and/or particularly a diluted emulsifiable concentrate, a diluted suspension concentrate, a diluted suspoemulsion, a diluted microemulsion and/or a diluted multiple emulsion.
  • a further possible way of incorporating agrochemicai active materials in formulations of and used in this invention is as liquids or solutions of the active in a suitable, usually water immiscible, solvent in which are microencapsulated.
  • the water immiscible liquid which is or includes at least one compound of the formula (I) can be or be part of the fluid within which the microcapsules are dispersed and/or it may act as the solvent (when used) for the active within the microcapsules.
  • the microcapsules can be made by conventional methods from an emulsion of the liquid or dissolved active in a, normally aqueous, liquid for example by coacervation, particularly using proteinaceous polymers such as gelatin, in situ polymerisation of e.g.
  • the invention includes: h an agrochemicai formulation including an agrochemicai in microencapsulated form suspended in a liquid formulation including at least one compound of the formula (I); and i a microencapsulated agrochemicai which is a microencapsulated solution of an agrochemicai in a solvent including at least one compound of the formula (I), usually for spray application dispersed in water.
  • the invention further includes the use of compounds of the formula (I), as defined above, as carrier fluids or solvents for agrochemicals.
  • the carrier fluid is or includes iso-propyl benzoate.
  • R ⁇ is a is a C- ⁇ to C20 alkyl or alkenyl group, C- ⁇ to C-J Q alkyl group.
  • R 1 is a C ⁇ to CQ alkyl group, and is desirably branched e.g. it is an iso- propyl (prop-2-yl), sec-butyl (but-2-yl), /so-butyl (2-methyl-prop-1-yl) and/or terf-butyl group, to reduce the ease with which the ester can be hydrolysed.
  • esters with secondary alcohols are particularly useful in this regard and R 1 is thus especially a C3 to C5 secondary alkyl group and very desirably an /so-propyl group.
  • the alkyl group R 1 is a relatively short chain, particularly a C-j to Cg alkyl, group, it may be a longer chain group as in a C5 to C20 alkyl or alkenyl group, particularly a C ⁇ to C-J S alkyl or alkenyl group which may be straight chain e.g. as in mixed esters such as (mixed C-12/C13 alkyl) benzoate, or branched e.g.
  • Unsaturated longer chain groups include oleyl. Where longer chain length groups are used, particularly longer than C-j 2. i is desirable that are or include branching and/or unsaturation and/or that mixtures of such esters are used, as these tend to be more liquid than straight chain saturated esters.
  • the carboxylic acid used in the ester can be a dihydrocinnamic acid or a phenyiacetic acid, it is very desirably a benzoic acid i.e. desirably m is 0. Similarly, although the phenyl ring of the acid may be substituted, it is desirable that it is unsubstituted i.e. desirably p is 0.
  • the esters used in the invention may include a (poly)alkyleneoxy chain, (AO) n in formula (I), between the carboxyl group and the group R 1 .
  • the (poly)alkyleneoxy chain is desirably a (poly)ethyleneoxy, a (poly)propyleneoxy chain or a chain including both ethyleneoxy and propyleneoxy residues.
  • n is 0.
  • a particularly useful ester is /so-propyl benzoate and the invention specifically includes a method of treating vegetation, particularly by spraying and agrochemicai formulations and methods, in which /so-propyl benzoate is used as a solvent, carrier fluid or crop oil.
  • /so-propyl benzoate has a combination of properties that make it exceptionally useful in these roles.
  • the carrier fluid used in formulations of the invention is wholly of one or more compounds of the formula (I).
  • other solvents or carrier fluids may be used in admixture.
  • other such fluids include mineral oil, vegetable oil, propylene tetramer and ethyl lactate.
  • oils containing aromatic hydrocarbons can be included it is unlikely that they will be used as a major component of any such mixed carrier fluid, because of the likely adverse environmental impact.
  • the compound(s) of the formula (I) can be used as co-solvents, or solvency improvers, or as the principal solvent or carrier fluid in the formulation.
  • the proportion of the compound(s) of the formula (I) used in the solvent will usually be from 0.5 to 25%, more usually from 1 to 10%, and particularly from 1 to 5%, by weight of the solvent, with the remaining carrier fluid or solvent materials being from 99.5 to 75, more usually from 99 to 90% of the carrier fluid or solvent.
  • the proportion of the compound(s) of the formula (I) used in the solvent will typically be present as at least 25%, usually at least 40%, more usually at least 50%, desirably at least 60%, and particularly at least 75%, by weight of the total carrier fluid used with the other carrier fluid components or solvents (when present) typically from 1 to 75%, usually from 1 to 60%, more usually from 2 to 40%, desirably 3 to 25%, and particularly 5 to 15% by weight of the total carrier fluid used.
  • the compounds of the formula (I) can be used as or in crop oils either for crop oils in agrochemicai formulations where they can provide beneficial effects on the performance of the agrochemicals (somewhat similar overall effects to adjuvants) or for crop oil sprays where the oil itself functions to provide beneficial effects on crops, particularly fruit trees as in winter oil spraying, so treated.
  • the spray formulation will generally include at least one surfactant material, particularly to improve wetting and/or spreading of the crop oil on the crop plants sprayed.
  • the crop oil can be sprayed as a neat oil formulation or as an emulsion of the crop oil in water.
  • the compounds of the formula (I) can also be used as solvents for other components of agrochemicai formulations, particularly for water insoluble active agrochemicals.
  • the active agrochemicai can be of a wide range of materials.
  • the agrochemicaliy active component of the formulation may be one or more plant growth regulators, herbicides, and/or pesticides, for example insecticides, fungicides, acaricides, nematocides, miticides, rodenticides, bactericides, molluscicides and bird repellants.
  • esters of the formula (I) when water soluble actives are used the esters of the formula (I) will be included primarily as crop oils or adjuvants, and where water insoluble actives are used the esters of the formula (I) will b ⁇ included primarily as solvents or carrier fluids for the active.
  • Typical water soluble actives are water soluble herbicides, particularly non-selective, herbicides including phosphonomethyl glycines such as Glyphosate and Sulfosate ⁇ respectively the /so-propylamino and trimethylsulphonium salts of ⁇ /-phos- phonomethyl glycine ⁇ ; phosphinyl amino acids such as Glufosinate ⁇ 2-amino-4- (hydroxymethyl-phosphinyl) butanoic acid ⁇ particularly as the ammonium salt and bipyridinium compounds such as Paraquat ⁇ 1 ,1 '-dimethyl-4,4'-bipyridinium ⁇ .
  • water soluble active materials particularly suitable actives include, non-selective herbicides, particularly ⁇ /-(phosphono- methyl) glycine type herbicides, such as Glyphosate and Sulfosate and phosphinyl amino acids, such as Glufosinate, particularly as the ammonium salt.
  • non-selective herbicides particularly ⁇ /-(phosphono- methyl) glycine type herbicides, such as Glyphosate and Sulfosate and phosphinyl amino acids, such as Glufosinate, particularly as the ammonium salt.
  • Actives which can be used in this type of formulation include: ' Herbicides including: triazines such as atrazine ⁇ 6-chloro-A/-ethyl-N'-(1-methylethyl)-1 ,3,5-triazine-2,4-diamine, and prometryn ⁇ /, ⁇ -bis(1 -methylethyl)-6-(methylthio)-1 ,3,5-triazine)-2,4-diamine ⁇ ; substituted ureas such as diuron ⁇ W-(3,4-dichlorophenyl)-W, ⁇ /-dimethylurea ⁇ ; sulphonyl ureas such as metsulfuron-methyl ⁇ 2-[[[[[[(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl) amino]carbon
  • Fungicides including thiocarbamates, particularly alkylenebis(dithiocarbamate)s, such as maneb ⁇ [1 ,2-ethanediylbis- [carbamodithiato] (2-)] manganese ⁇ and mancozeb ⁇ [[1 ,2-ethanediyl- bis[carbamodithiato]j (2-)]manganese mixture with [[1 ,2-ethanediylbis[carbamodithiatoj] (2-)jzinc ⁇ ; strobilurins such as azoxystrobin ⁇ methyl (E)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxyj- a-(methoxymethylene)benzeneacetate ⁇ and kresoxim-methyl ⁇ (E)-a-(methoxyimino)- 2-[(2-methylphenoxy)methyl]benzeneacetic acid methyl ester ⁇ ; dicarboximi
  • Combinations of more than one active including more than one type of active may be used if desired.
  • water soluble actives may be dissolved in an aqueous phase in the formulation and a further active can be included in dispersed form or in solution in the carrier fluid.
  • formulations can be made up using a water soluble (non-specific) herbicide such as Glyphosate, Sulfosate and/or Glufosinate, with a selective herbicide, such as a sulphonyl urea e.g. metsulfuron-methyl, pyridine carboxylic acid e.g. clopyralid, aryloxy alkanoic acids e.g.
  • 2,4-D substituted ureas e.g. diuron, or 2-(4-aryloxyphenoxy)propionic acids e.g. clodinafoppropargyl, and/or with an insecticide and/or fungicide, in particular where the other active is dissolved in the carrier fluid.
  • 2-(4-aryloxyphenoxy)propionic acids e.g. clodinafoppropargyl
  • an insecticide and/or fungicide in particular where the other active is dissolved in the carrier fluid.
  • the surfactant(s) included in the composition of and used in the invention can serve a variety of purposes including as wetting agents, emulsifiers, dispersants and adjuvants.
  • Wetting agents can be nonionic surfactants such as alcohol ethoxylates e.g. of Cg to Ci 5, particularly primary, alcohols, which may be linear, branched or mixtures of linear and branched, particularly mono-branched, with from 5 to 30 moles of ethylene oxide; and alkoxylates of such alcohols particularly mixed ethoxylate/ propoxylates which may be block or random mixed alkoxylates, typically containing from 3 to 10 ethylene oxide residues and from 1 to 5 propylene oxide residues, particularly where the polyalkoxylate chain is terminated with propylene oxide unit(s); polyoxyethylene/polyoxypropylene copolymers, particularly block copolymers, such as the Synperonic PE series of copolymers available from Uniqema, and alkyl polysaccharides; silicone based surfactants; anionic surfactants e.g. isethionates, such as sodium cocoyl isethionate, naphthalene sulphate,
  • Emulsifiers can be anionic surfactants e.g. alkali metal or alkali earth metal salts of sulphonated hydrocarbons such as alkyl benzene sulphonates particularly Ca dodecylbenzene sulphonate; and/or non-ionic surfactants including alcohol alkoxylates such as those based on C3 to C22 > particularly C-12 to C-
  • alkali metal or alkali earth metal salts of sulphonated hydrocarbons such
  • non-ionic surfactants can encompass both water in oil and oil in water emulsifiers; generally the former have relatively long hydrophobes and/or small hydrophiles, particularly polyethylenoxy, chains and the latter have relatively shorter hydrophobes and/or larger hydrophiles.
  • Dispersants for dispersing solids in water include naphthalene sulphonate formaldehyde condenses e.g. as sodium and ammonium salts; sodium, lignosulphonates e.g. as calcium and ammonium salts; maleic anhydride copolymers e.g. as sodium and ammonium salts; condensed phenolsulphonic acid e.g.
  • condensed fatty acid surfactants such as polycondensed fatty acids and/or their quaternary ammonium and/or alkaline earth metal and/or amine derivatives and polyamine / fatty acid condensate solutions; polyoxyalkylene amine derivatives; polyester polyether block copolymers; and polyaikylene glycol ethers.
  • Adjuvants can be non-ionic surfactant adjuvants such as the so-called hydrocarbyl, particularly alkyl e.g. C5 to C-14, especially from 03 to C-12 alkyl, polysaccharides (generally more correctly described as oligosaccharides), typically having an average of from 1 to 3, more usually from 1.3 to 2 saccharide units in the oligosaccharide chain; hydrocarbyl, particularly alkyl, amine alkoxylates, particularly ethoxylates; linear or mono-branched (or mixed) alcohol alkoxylates, particularly ethoxylates; sorbitol and sorbitan fatty acid esters and their alkoxylated, particularly ethoxylated derivatives.
  • Further adjuvants include amphoteric surfactants such as betaines and cationic surfactants such as long chain alkyl e.g. C-
  • Coadjuvants such as ionic and/or inorganic materials, for example ammonium sulphate, may be included in adjuvant containing agrochemicai formulations of the invention, particularly with non-ionic surfactant adjuvants.
  • solvent and carrier fluid refer to an organic solvent or carrier fluid which includes at least one compound of formula (I), particularly /sopropyl benzoate and "emulsifiers", “dispersants”, “wetters” and “adjuvants are particularly materials as described above.
  • compositions include:
  • compositions can be applied neat or diluted (emulsified) in water.
  • neat typically they will be applied as so called “winter oil” sprays on e.g. fruit trees, typically at from 0.1 to 10 l-ha "1 , more usually from 1 to 3 I. ha "' ' .
  • the surfactant(s) will usually function as a wetters including to aid spreading and penetration of the oil over or into the bark of treated plants particularly trees.
  • rate of dilution is typically from 1 to 10000 times, more usually from 10 to 1000 times, by volume.
  • Such diluted formulations will typically be sprayed at from 10 to 500 l.ha “' ' , more usually from 50 to 300 l.ha” 1 .
  • the surfactant(s) will usually include emulsifier(s) and may also include wetter(s).
  • compositions will depend on the form of the formulation, particularly for concentrate formulations.
  • spray formulations including compounds of the formula (I) can be made up in situ in the spray tank from the individual components. However, this is generally not convenient as it requires the end user to have suitable (relatively high intensity) mixing equipment. More usually the agrochemicai and surfactant components will be incorporated in preformulated compositions which can be diluted with water at the point of use to form sprayable formulations requiring no or only moderate mixing.
  • Emulsifiable concentrates are oil based concentrates which on dilution with water spontaneously or very readily form oil in water emulsions, typically of an agrochemicai dissolved in an oil, in the water phase. They are also sometimes described as "built-in concentrates".
  • the surfactant(s) in emulsion concentrates act(s) to form a homogeneous concentrate that readily or spontaneously emulsifies on dilution into water.
  • the surfactant is often a combination of two or more surfactant compounds including emulsifiers to stabilise the emulsion formed on dilution and may also include adjuvant surfactants.
  • Typical ranges for the main components of emulsifiable concentrates are:
  • Oil based suspension concentrates are used to disperse oil insoluble active ingredients which are also water insoluble or are too water soluble to include in a water based flowable or are not chemically stable in water.
  • Such formulations will also usually include dispersant surfactant(s), particularly condensed fatty acid surfactants, and they also usually include emulsifier(s) to emulsify the carrier fluid phase on dilution into water.
  • Such formulations may also include adjuvants. On dilution into water a water insoluble solid active may become dispersed directly in water or may be a solid dispersed phase in the emulsified oil phase (this is very similar to suspoemulsions on dilution see also below).
  • Overall the composition of oil based concentrates is typically as set out below:
  • Agrochemicai suspoemulsion concentrates are formulations which on dilution (in water) give suspoemulsions i.e. which include at least one liquid (emulsion) disperse phase and at least one solid disperse phase, in a continuous aqueous phase.
  • the concentrate formulation can itself be a suspoemulsion, in effect just more concentrated (having less water) than the diluted (spray) formulation; or it may be a dispersion of a solid disperse phase in an emulsifyable concentrate, which on dilution forms an emulsion.
  • agrochemicai formulations which include an oil soluble active, present as a solution in the oil emulsion disperse phase, and a solid water insoluble (and usually also oil insoluble) active, i.e. the solid components usually include an agrochemicai active, present as dispersed particles, although other formulation components may also be present as dispersed solid particles.
  • the solid dispersed phase may be dispersed within the oil based emulsion droplets.
  • Suspoemulsions are typically based on an oil solution of one agrochemicai also including a solid water insoluble active or other solid component present as dispersed particles.
  • Suspoemulsion concentrates are typically diluted in water for spray application to form suspoemulsions. Overall the composition of suspoemulsion concentrates are typically as set out below:
  • Microemulsions are thermodynamically stable, transparent concentrate formulations which include a liquid dispersed emulsion phase with a droplet size fine enough not to scatter visible light e.g. less than 0.1 ⁇ m. They include surfactants to stabilise the microemulsion particularly emulsifiers and may also include adjuvants. Microemulsions are typically diluted into water usually to form microemulsion spray formulations (formulations that form emulsions are more usually designated as emulsifiable concentrates) before spraying. Overall typical microemulsion compositions are as set out below:
  • Agrochemicai multiple emulsion formulations are concentrate formulations in which a dispersed emulsion phase has within its droplets a dispersion of droplets of another liquid. There are thus two emulsions an outer emulsion and an inner emulsion and the phases can be described as outer and inner external and internal phases. There are two basic types of multiple emulsion: water in oil in water (W/O/W) and oil in water in oil (O/W/O), although W/O/W emulsions are more likely to be used in this invention.
  • a typical W/O/W multiple emulsion will have from 10 to 80%, more usually 20 to 60%, particularly 30 to 50%, by weight internal water in oil (W/O) emulsion and correspondingly 90 to 20%, more usually 80 to 40%, particularly 70 to 50%, by weight external water phase.
  • the internal W/O emulsion will typically include from 1 to 30% by weight water in oil emulsifier and from 20 to 90% by weight of oil phase including a compound of the formula (I) (as defined above).
  • the external water phase will typically include a further 1 to 10% oil in water emulsifier.
  • . typically at least on oil soluMe agrochemicai will be dissolved in the oil phase.
  • active materials can be water soluble actives dissolved in either the inner water internal phase or in the external water phase, or insoluble actives dispersed in the multiple emulsion.
  • Multiple emulsion formulations are typically diluted into water usually to before spraying. Overall the composition of agrochemicai multiple emulsions are typically as set out below:
  • the compounds of the formula (I) can be included in agrochemicai spray formulations by additions to the aqueous based tank mix, in effect immediately before spraying.
  • the addition will usually be as a crop oil that acts to improve the overall effectiveness of the agrochemicai spray.
  • the proportion of the crop oil used in this way is typically from 0.02 to 2 %, more usually from 0.2 to 1%, by weight of the overall spray formulation.
  • the formulation will usually include emulsifier surfactant to aid dispersion of the crop oil as an emulsion in the spray formulation.
  • the compounds of the formula (I) can be used alone or in combination with other crop oils, usually within the composition ranges set out above for oil mixtures.
  • the oil including the compounds of the formula (I), may also include some or all of the adjuvant surfactant added to the spray formulation and in this approach the oil acts as a carrier fluid (or solvent) for the adjuvant surfactant (as well as potentially as a crop oil).
  • the oil acts as a carrier fluid (or solvent) for the adjuvant surfactant (as well as potentially as a crop oil).
  • Concentrated forms of agrochemicai formulations are usually diluted with water to make sprayable diluted aqueous formulations.
  • the dilution rate is from 10 to 10000, particularly 30 to 1000, times by volume.
  • the dilution rate is chosen to match the required spray volume to the desired application rate of the agrochemicai formulation.
  • the invention includes a method of making a diluted agrochemicai formulation for spraying (spray tank mix) which includes diluting a concentrate containing at least'one active agrochemicai, particularly one or more emulsion concentrate, emulsifiable concentrate, suspension concentrate, suspoemulsion concentrate, microemulsion and/or multiple emulsion, which concentrate also includes at least one compound of the formula (I) with water.
  • the invention also includes a method of making a diluted agrochemicai formulation for spraying (spray tank mix) which includes mixing in any order: a a concentrate containing at least one active agrochemicai, particularly one or more emulsion concentrate, emulsifiable concentrate, suspension concentrate, suspoemulsion concentrate, microemulsion and/or multiple emulsion, which concentrate desirably also includes at least one compound of the formula (I); b a solution of an adjuvant surfactant in a carrier fluid including at least one compound of the formula (I); and c water, particularly in an amount of from 10 to 10000 times by volume of the combined volume of components a and b; to form the diluted agrochemicai formulation.
  • the application rate of diluted formulations is typically from 50 to 500, more usually from 50 to 400 and commonly about 300, l(spray formulation). ha "1 (crop treated).
  • the application rate may be significantly lower typically 0.5 to 50, more usually 1 to 10, l(spray formulation), ha "1 (crop treated).
  • the concentration of the active agrochemicai is typically from about 0.001 to about 3%, more usually from 0.1 to about 0.5 and particularly about 0.2% by weight of the spray formulation.
  • the typical concentration of adjuvant is from 0.02 to about 2%, more usually 0.2 to about 1% and particularly abo it 0.1 %.
  • the weight ratio of active agrochemicai to adjuvant is usually from 1 :100 to 10:1 , more usually from 1 :10 to about 4:1.
  • agrochemicai generally in the range 0.5 to 4000 g.ha “1 , more usually from 3 to about 2000 g.ha” 1 (the actual amount depending on the particular crop, agrochemicai and effect desired).
  • spray concentration generally higher spray concentrations will be used, but the ratio of agrochemicai to adjuvant will be within the ranges given above.
  • Other potential components of agrochemicai formulations of and used in this invention include: thickeners or rheology modifiers are commonly used in liquid concentrate formulations, to stabilise the concentrate against settling, flocculation or phase separation prior to dilution.
  • the amount of thickener used is typically from 0.01 to 5% by weight of the formulation, antifoams, particularly silicon based materials such as organopolysiloxanes, typically used in ' an amount from 0.1 to 10%, preferably 0.2 to 6% by weight of the surfactant; 0.01 to 5%, particularly 0.02 to 2% by weight of agrochemicai concentrate and 0.0001 to 0.1% preferably 0.001 to 0.05% by weight of a spray formulation at end use dilution; viscosity modifiers, particularly gums such as xanthan gums; cellulose derivatives, such as carboxyl-methyl, -ethyl, or -propyl cellulose, typically used at from 0.01 to 5 wt % of a concentrated formulation; and other non surfactant materials such as stabilisers and/or anti-microbials, typically used at from 0.01 to 5 wt % of a concentrated formulation, cold stabilisers, particularly mono propylene glycol, typically used at from 5 to 20 w
  • the actives as used were solids (assumed 95+% active).
  • the normal solvent and concentration used for making agrochemicai formulations is indicated above in brackets.
  • sopropyl benzoate can be used to replace a variety of aromatic solvents used conventionally as solvents for agrochemicai actives.
  • aromatic solvents used conventionally as solvents for agrochemicai actives.
  • acetochlor and propargite some impurities precipitated from solution at ambient temperature. Samples stored at lower temperatures gave no additional precipitation confirming that the active remained in solution.
  • the emulsions are suitable for spraying as a crop oil and with the inclusion of an oil soluble agrochemicai for agrochemicai spray application.
  • Emulsions of Soli were made up for evaluation using the following formulation:
  • the surfactant was melted and added to the solvent at ca 50°C.
  • the water was heated separately to ca 50°C and the IPB and surfactant added to the water with stirring (250 rpm; ca 4.2Hz).
  • the formulation was homogenised using a high energy stirrer (such as a Silverson or Ultra Turax homogeniser) and then allowed to cool to ambient temperature under stirring.
  • the solvent formulations were used to make emulsions and tested for emulsion stability as described in Example 2 above. The results are set out in Table 3 below:
  • Emulsions of various solvents were evaluated for phytotoxicity at solvent concentrations of 0 (blank), 1 , 10, and 50% solvent in the emulsion.
  • the formulations are set out in Table 4a below and the results of phytotoxicity testing in tomatoes and wheat are summarised in Table 4b below.
  • test emulsifiable concentrate was made up using Soli in the following formulation:
  • Emulsification and emulsion stability of this concentrate were tested under temperature conditions designed to highlight any crystal growth upon dilution.
  • the concentrate was mixed with 342 water at 0°C or at 30°C to give a 2% dilution - initial emulsification performance was good to excellent - the concentrate gave perfect self emulsification with no signs of separate droplets breaking away. After storage (1m 40°C) the emulsification performance was good - close to perfect self emulsification - only a few droplets tending to break away.
  • Emulsion stability was tested and the results set out in Table 5 below. No crystal growth was noted for any of the dilutions at 0° or at 30°C.
  • the surfactants were melted and added to the solvent at about 50°C.
  • the water was heated to about 50°C and the solvent/surfactant blend added to the water with stirring (250 rpm; ca 4.2 Hz).
  • the emulsion was subsequently homogenised with a high energy stirrer (Silverson or Ultra Turrax) and then allowed to cool to ambient temperature under stirring.
  • Spray oils were made up using the following formulation:

Abstract

L'invention concerne le traitement de plantes par pulvérisation d'une préparation contenant au moins un composé de formule (I): (R2)p-Ph(CH2)m-COO-(AO)n-R1 (I), dans laquelle R¿1?, AO, n, m, Ph, R?2¿ et p ont des significations définies, en particulier la pulvérisation des plantes ou de leur environnement immédiat avec des benzoates d'alkyle associés à au moins un tensioactif et/ou à un produit agrochimique. Les composés de formule (I) sont des solvants efficaces qui ont une faible incidence sur l'environnement. L'invention concerne le traitement par pulvérisation des plantes avec une préparation d'huile phytosanitaire dérivée des composés de formule (I), et/ou avec des préparations d'herbicides et/ou de pesticides comprenant les composés de formule (I).
PCT/GB2001/002052 2000-05-15 2001-05-10 Traitement de pulverisation agrochimique et preparations a pulveriser WO2001087064A1 (fr)

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US20130260996A1 (en) * 2012-04-02 2013-10-03 Dow Agrosciences Llc Aromatic esters for controlling agricultural spray drift
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TWI677285B (zh) * 2011-04-26 2019-11-21 先正達有限公司 配製物組分
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US10912298B2 (en) * 2005-09-01 2021-02-09 E. I. Du Pont De Nemours And Company Liquid sulfonylurea herbicide formulations
US20140005051A1 (en) * 2005-09-01 2014-01-02 E I Du Pont De Nemours And Company Liquid sulfonylurea herbicide formulations
WO2009032481A3 (fr) * 2007-08-30 2010-05-27 Dow Agrosciences Llc Formulation d'émulsion stable empêchant une interaction à travers l'interface eau-huile
CN101959403A (zh) * 2007-08-30 2011-01-26 陶氏益农公司 阻止跨水-油界面相互作用的稳定乳液制剂
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CN107006493B (zh) * 2007-08-30 2020-09-22 陶氏益农公司 阻止跨水-油界面相互作用的稳定乳液制剂
AU2008296737B2 (en) * 2007-08-30 2014-01-09 Corteva Agriscience Llc Stable emulsion formulation hindering interaction across the water-oil interface
US20140094370A1 (en) * 2011-04-26 2014-04-03 Syngenta Limited Formulation component
TWI684409B (zh) 2011-04-26 2020-02-11 英商先正達有限公司 配製物組分
TWI677285B (zh) * 2011-04-26 2019-11-21 先正達有限公司 配製物組分
CN103501602A (zh) * 2011-06-10 2014-01-08 胡茨曼澳大利亚股份有限公司 用于农业油基于配制剂的结构化剂和乳化剂
WO2012167322A1 (fr) * 2011-06-10 2012-12-13 Huntsman Corporation Australia Pty Limited Agents structurants et émulsifiants destinés à des formulations à base d'huile pour l'agriculture
CN103501602B (zh) * 2011-06-10 2016-08-17 胡茨曼澳大利亚股份有限公司 用于农业油基于配制剂的结构化剂和乳化剂
CN106900714A (zh) * 2012-04-02 2017-06-30 陶氏益农公司 用于控制农业喷雾漂移的芳族酯
EP2833715A4 (fr) * 2012-04-02 2016-01-06 Dow Agrosciences Llc Esters aromatiques pour le contrôle d'embruns de pulvérisations agricoles
US10039279B2 (en) * 2012-04-02 2018-08-07 Dow Agrosciences Llc Aromatic esters for controlling agricultural spray drift
JP2015512446A (ja) * 2012-04-02 2015-04-27 ダウ アグロサイエンシィズ エルエルシー 農業スプレードリフトを制御するための芳香族エステル
CN104334018A (zh) * 2012-04-02 2015-02-04 陶氏益农公司 用于控制农业喷雾漂移的芳族酯
US20130260996A1 (en) * 2012-04-02 2013-10-03 Dow Agrosciences Llc Aromatic esters for controlling agricultural spray drift
WO2014139805A1 (fr) * 2013-03-13 2014-09-18 Basf Se Concentré émulsionnable comprenant un pesticide, un benzoate d'alkyle et un amide d'acide gras
US11109588B2 (en) 2019-02-19 2021-09-07 Gowan Company, L.L.C. Stable liquid formulations and methods of using the same

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