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
  • A01N25/30—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 characterised by the surfactants
• • 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
  • A01N25/12—Powders or granules
  • A01N25/14—Powders or granules wettable
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
  • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
  • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom

Definitions

• the present invention relates generally to dispersants, for use in agricultural applications, in
• the present invention relates to methods for the dispersion of insoluble material with copolymeric dispersants which dispersions are formed with improved dispersibility and show
• the present invention also relates to methods of producing
• dispersible formulations the formulations per se and methods of treating substrates with dispersions produced from such formulations.
• the active principle is typically
• SC suspension concentrate
• WP wettable powder
• SC degree of agglomeration
• WP Wettable powder
• WG water dispersible granule
• copolymer surfactants based on an hydrophobic moiety plus ethyleneoxide. Also used are
• anionic surfactants used include sulphonated derivatives of arylformaldehyde condensates, polyacrylates and lignosulfonates.
• Dispersants for WP and WG formulations are usually limited by the requirement that the dispersant be solid at ambient temperatures, be non-gelling and not dissolve the active principle. For these reasons, conventional non-ionic surfactants are often unsuitable, and
• anionic dispersants are preferred.
• Known effective dispersants for WP and WG formulations are preferred.
• sulphonated alkylnaphthalene/formaldehyde condensate salts include sulphonated alkylnaphthalene/formaldehyde condensate salts and lignosulfonate salts.
• oj-Olefin-polycarboxylate copolymers are well known as dispersants in a wide range of
• EP 201417 describes the use of
• JP 62036302 describes
• copolymers having a molecular weight range of from 5000-20000 for use with granular
• French Patent No. 2,397,444 describes stable and concentrated dispersions of active materials which may be prepared from non-dusting powders or granular materials. It is necessary to separate the active material in the presence of a salt of an acidic resin, such as, for example,
• olefin monomers and ⁇ , ⁇ -unsaturated oxyacid monomers surprisingly provides improvements
• alternating copolymers for use as dispersants in agricultural compositions provide improved
• dispersant comprising a copolymer wherein said copolymer comprises a residue of a
• said first comonomer are selected from the group consisting of esters, amides,
• copolymer wherein said copolymer comprises a residue of a first comonomer and a
• said second comonomer is an olefin having at least one
• esters are selected from the group consisting of esters, amides, thioesters and functional
• the second comonomer are selected from the group consisting of epoxides
• copolymer wherein said copolymer comprises a residue of a first comonomer and a
• said second comonomer is an olefin having at least one
• esters are selected from the group consisting of esters, amides, thioesters and functional
• the second comonomer are selected from the group consisting of epoxides
• an agrochemical formulation comprising the steps of: (i) combining at least one insoluble material suitable for agricultural use with at least one
• dispersant comprising a copolymer wherein said copolymer comprises a residue of a
• said first comonomer are selected from the group consisting of esters, amides,
• aromatic and heteroaromatic groups wherein said optional substituents are selected from the group consisting of sulfonates, nitrates, phosphates and other substituents
• agrochemical formulation comprising the steps of:
• said first comonomer are selected from the group consisting of esters, amides,
• an agricultural formulation comprising at least one insoluble material and at least one dispersant comprising a copolymer wherein said copolymer comprises a residue of a first comonomer and a residue of a second comonomer, wherein said first comonomer is an , ⁇ -unsaturated oxyacid or
• said second comonomer is an olefin having at least one polymerizable double
• esters consisting of esters, amides, thioesters and functional groups derived from reaction with
• nucleophilic reagents and wherein the substituents for the second comonomer are selected
• dispersant comprising a copolymer wherein said copolymer comprises a residue of a
• first comonomer and a residue of a second comonomer, wherein said first comonomer is an , ⁇ -unsaturated oxyacid or anhydride and said second comonomer is an olefin
• said first comonomer are selected from the group consisting of esters, amides,
• solubility in water it may confer additional polarity or charge density to the dispersant such
• copolymer and therefore the copolymer is more readily soluble and may more readily align
• the first comonomer for use in the present invention may be any comonomer polymerizable
• suitable preferred first comonomers of the present invention include fumaric acid, maleic acid and anhydrides, and the esters, amides and imides
• the second comonomer for use in the present invention is an olefin having at least one
• alicyclic monomer an aliphatic cyclic monomer containing moieties such as
• a cyclic alkyl, cyclic alkenyl or heterocyclic groups and which may comprise one or more
• cyclic double bond may optionally be substituted.
• polymerizable exo-cyclic double bond of the present invention may include, for example, ⁇ -
• pinene 5-ethylidene-2-norbornene, methylene cyclohexane and methylene cyclopentane.
• alicyclic monomer having a polymerizable endo-cyclic double bond.
• alicyclic monomer is as hereinabove defined. It will be understood that by endo-cyclic is meant the
• polymerizable double bond has both ends (or termini) forming part of the cyclic structure of
• Alicyclic monomers having a polymerizable endocyclic may optionally be substituted.
• Alicyclic monomers having a polymerizable endocyclic may optionally be substituted.
• double bond may include substituted and unsubstituted norbornene, cyclopentadiene and
• benzene and substituted benzene include benzene and substituted benzene, cyclopentane, cyclohexane, and other
• suitable ⁇ -olefinic cyclic compounds include limonene and similar terpenes, vinyl
• the second comonomer of the second embodiment of the present invention may be an ⁇ - olefin having an alkyl group such as diisobutylene, isobutylene, n-octene, n-decene, allyglycidylether of vinylisobutylether.
• the second comonomer may also be an internal
• R is M a metal, quaternary ammonium, phosphonium or sulphonium residue, R 2
• R 5 is OR ⁇ , NR ⁇ , SR ⁇ , wherein Rg ,R 7 , are H, alkyl, O-alkyl, or alkyl groups with a hetero atom substituent.
• second comonomer may be alternatively described as a residue having formula III
• R 8 represents hydrogen, a straight or branched chain alkyl of from 1-4 carbon atoms
• Rg represents hydrogen, a branched chain alkylradical from 1-12 carbon atoms, or cycloalkyl
• R 10 is a straight or branched chain alkyl radical of from 1-4 carbons and R n is given
• R 12 represents one or more alkyl radicals or one or more of H,Cl,OR and SO 3 R,
• NO 2 , PO 3 R, and X is a hetero atom other than carbon; and/or an olefin shown by formula
• R 13 is Cl, or SO 3 R, , alkyl, O-alkyl, O-aryl and R 14 , represents from 4-20 carbon atoms such as to make H a cyclic or polycyclic alkane or polyalkenyl compound, R 15 , is an
• R 9 is the same or different and as hereinabove defined.
• the dispersant copolymers of the present invention may also include copolymers being the
• anhydride and another olefmic monomer not limited to being of -an alternating structure, that
• Such derivatisation includes that obtained from reaction of groups pendant to the copolymer
• nucleophilic reagents such as alcohols, amines and
• esters, amides and thioesters respectively.
• copolymers with pendant aryl or heteroaryl groups can be
• copolymers with hydroxyl groups can be esterified with acids including carboxylic, sulphuric and phosphoric acids.
• acids including carboxylic, sulphuric and phosphoric acids.
• repeating, units are preferably monomers but may also be dimers, trimers or small oligomers.
• the copolymer may contain additional comonomer residues.
• additional comonomer residues For example, the addition of
• the copolymer may contain residues of additional
• olefin comonomers whether derivatised or not.
• copolymers of three or more comonomers also include copolymers of three or more comonomers. Additional comonomers
• polymer backbone is provided in the presence of regularly spaced anionic charge or steric
• the preferred molecular weights of the copolymers of the present invention are in the range
• dispersants in agricultural compositions provide improved and consistent dispersant
• alkylnaphthalene formaldehyde condensate salts alkylnaphthalene formaldehyde condensate salts.
• copolymer derivatives resulted in a less stable and sometimes unstable dispersion. Further,
• copolymers of methylvinylether and maleic anhydride also afford an unstable dispersion.
• copolymers of this invention may give acceptable stability
• formulations typically show improved dispersibility. When compared to sulfonated alkyl
• insoluble materials such as active principals are delivered in aqueous suspension.
• Active principals such as those used in WP, WG and
• SC formulations are generally insoluble at ambient temperatures. Water insoluble materials
• insecticides fungicides, biocides, molluscicides, algaicides, plant growth regulators,
• anthelmintics rodenticides, nematocides, acaricides, amoebicides, protozoacides, crop safeners and adjuvants.
• Examples of such actives commonly granulated or made as powders
• triazine herbicides such as simazine, atrazine, terbuthylazine,
• terbutryn terbutryn, prometryn and ametryn, urea herbicides such as diuron and fluometron, sulphonyl
• urea herbicides such as chlorsulfuron, metsulfuron methyl, nicosulfuron and triasulfuron,
• sulphonanilide herbicides such as flumetsulam, organophosphate insecticides such as azinphos
• bendiocarb carbaryl and BPMC, synthetic pyrethroids such as bifenthrin, as well as various
• fungicides including dimethomo ⁇ h, benomyl, carbendazim, mancozeb, triazoles
• fertilizers and also water soluble active principles may use water dispersible formulations either by addition of inert carriers for convenience in handling or to aid in a
• fillers and carriers for example but not limited to, natural and synthetic silicates and silicate
• Such materials may be added as porous carriers, as moisture inhibition agents,
• fillers may include natural silicates such as
• diatomacious earth synthetic precipitated silicas, clays such as kaolin, attapulgites and
• hydroxides or organic materials such as bagasse, charcoal, or synthetic organic polymers.
• formulations is a surfactant wetting agent.
• formulations is to aid removal of air from particle surfaces during manufacture and to aid
• the role of the wetter may be to aid
• the dispersant may itself function as a suitable wetting agent while in others the dispersant may show an antagonistic effect on the wetter.
• alkylpolysaccharide di or mono alkyl sulphosuccinate
• surfactant delivered in the form of a urea surfactant complex is delivered in the form of a urea surfactant complex.
• the step of dispersing the formulation in an aqueous medium may be achieved by any one of the following steps:
• dispersion of the formulation in an aqueous solution may be conducted either by hand or with
• Mechanical agitation may include stirring, mixing,
• the suspension of insoluble material in aqueous medium will be typically used for the
• suspension onto the substrate may be achieved by any convenient means, including spraying,
• Granules are generally dispersed in water prior to being sprayed by the farmer.
• Farm sprays may be as a small back-pack handspray or a large boom spray or other
• Formulations of the present invention may also be applied to the substrate directly, prior to
• formulations provide a stable aqueous dispersion of finely milled insoluble hydrophobic
• dispersion can be measured by means of a suspensibility test as described by the CIPAC test MT 15 J . In this test the volume fraction of suspended material is compared to that which
• stability of the dispersion is the degree to which particles remain non aggregated. This may
• WP formulations are produced by milling the active principle either alone or in
• the milled material is then dry blended with a surfactant
• a formulation will desirably have a wettability of less than 1 minute and a
• fillers typically of particle size 5 to 15 ⁇ m, may be mixed with one or more surfactant wetters
• the agglomerates are typically granulated using one of many techniques including pan
• the wetter and dispersant may either be powder blended with the active ingredient or
• active ingredient fillers, wetter and dispersant may also be milled together in one operation
• a dispersion time of less than one minute is desirable
• the granules should also have good
• Suspensibility is typically tested using CIPAC MT 15J. Above 80% is a
• the granules should have low wet sieve retention.
• Wet sieve retention is typically
• a further desirable property of a WG formulation is that the granules should be non-dusty and
• resistance may be measured by subjecting granules to a set degree of agitation and measuring the level of smaller particles generated by means of passing through sieves of various sizes.
• Storage stability may be tested by storage at 50 degrees Celsius and tested as above at 1 month
• the granules should maintain these properties on storage. Su ⁇ risingly, it has
• surfactant wetting agents selected from
• alkylpolysaccharides dialkyl and monoalkylsulphosuccinate salts
• nonionic surfactants loaded onto porous silicate carriers and urea surfactant complexes of non-
• the wetting agent may be combined in .such formulations at a rate in excess
• alkylpolysaccharide class of wetting agents are alkylpolyglucosides derived from reaction with glucose and a primary hydrocarbon alcohol. Even more preferred are the highly crystalline derivatives such as obtained from ECOTERIC AS 20 and ECOTERIC AS 10 (Orica Australia Pty Ltd). Most preferred from the monoalkylsulphosuccinate class are sodium or potassium salts of
• dialkylsulphosuccinate class sodium or potassium salts of dicyclohexyl, diisooctyl and di-
• insoluble porous silicate carriers are ethoxylated surfactants loaded onto carriers such as
• complexes are urea adducts of alcohol ethoxylate surfactants such as TERWET 7050 (Orica
• a humectant may also be included.
• a dispersion is
• additives such as antifreeze, thickeners and antisettling agents, biocides and colouring agents may be added.
• additives such as antifreeze, thickeners and antisettling agents, biocides and colouring agents may be added.
• SC formulation to be acceptable it should not show a high degree of thickening, settling or growth of aggregates over time.
• SC's generally require good viscosity and storage stability. Storage stability is usually
• copolymers are suitable. When used alone, some dispersant copolymer derivatives give a
• the dispersant copolymers are used
• Example 1
• a Simazine 900g/kg WG formulation of the following composition was prepared.
• the dispersant used was an alkylnaphthalene formaldehyde condensate salt, SCS 2258 (ICI
• the granules were prepared by blending the solids with approximately 15 % by
• the resulting WG was tested for dispersibility by recording the time in seconds required for
• a simazine 900 g/Kg WG was prepared and tested as described in example 1 where the
• a Simazine 900g/kg WG formulation of the following composition was prepared :
• ATPLUS G73050 1.5 (now sold under the trademark TERWET 7050, Orica Australia Pty Ltd)
• the dispersant used was the sodium salt of an alternating copolymer of n-octene and maleic
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 3 with the dispersant being the sodium salt of a copolymer of n-decene and maleic
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 3 with the dispersant being the sodium salt of a copolymer of diisobutylene and
• a WG formulation was prepared and tested as described in Example 3 with the dispersant
• a WG formulation was prepared and tested as described in Example 3 with the dispersant
• a WG formulation was prepared and tested as described in Example 3 with the dispersant
• a Simazine 900g/kg WG formulation of the following composition was prepared :
• ATPLUS G73050 1.5 (now sold under the trade mark TERWET 7050, Orica Australia Pty Ltd)
• the dispersant used was the sodium salt of a copolymer of n-octene and maleic anhydride
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the mo ⁇ holine amide derivative of
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the mo ⁇ holine amide derivative of
• SMA 1000 (Atochem Inc), a 1: 1 molar ratio copolymer of styrene and maleic anhydride.
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the mo ⁇ holine amide derivative of
• SMA 3000 (Atochem Inc), a 3: 1 molar ratio copolymer of styrene and maleic anhydride.
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the aromatic sulphonated derivative
• SMA 1000 (Atochem Inc)
• a 1: 1 molar ratio copolymer of styrene and maleic anhydride (Atochem Inc)
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the co-polymer of alphamethylstyrene
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the copolymer of alphamethylstyrene
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the copolymer of alphamethylstyrene
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the copolymer of alphamethylstyrene
• Example 18 A Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the copolymer of dicyclopentadiene
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being a sulphonated derivative of the sodium salt of the copolymer of dicyclopentadiene and maleic anhydride. Results are shown in TABLE 2.
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in Example 9 with the dispersant being a sulphonated derivative of the sodium salt of the
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the copolymer of
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the mo ⁇ holine amide derivative of
• Gantrez AN119(Rhodia Co ⁇ .) a copolymer of methylvinyl ether and maleic anhydride
• a Simazine 900g/kg WG formulation was prepared and tested in the manner described in
• Example 9 with the dispersant being the sodium salt of the cyclohexyl amide derivative of Gantrez AN119(Rhodia Co ⁇ ), a copolymer of methylvinyl ether and maleic anhydride Results are shown in TABLE 2.
• Example 24
• Rhodopol 23 0.2 Rhodia Inc.
• the dispersant used was the sodium salt of a sulphonated copolymer of dicyclopentadiene
• the SC was prepared by dissolving the monoethylene glycol,
• the invention also includes all of the steps, features, compositions and

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Toxicology (AREA)
• Chemical & Material Sciences (AREA)
• Dispersion Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
• Fertilizers (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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• 1998
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