Pesticide dispersant

Abstract

The present disclosure provides a dispersant obtained from the reaction of styrene maleic anhydride with a monofunctional polyalkylene glycol. The dispersant may be combined with a pesticide and water to form an aqueous agricultural composition.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 62 / 684,885, filed June 14, 2018, the entire contents of which are expressly incorporated herein by reference.

[0002] STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT Not applicable.

[0003] The present disclosure relates generally to dispersants for use in various applications such as agricultural formulations. In particular, the dispersants of the present disclosure are products obtained from the reaction of styrene maleic anhydride copolymers with monofunctional polyalkylene glycols. [Background technology]

[0004] Active ingredients in many agricultural applications are often hydrophobic or water-insoluble in nature and, by necessity, are often administered as finely divided solids suspended in an aqueous medium. Most of these active ingredients are manufactured and sold in concentrated form, possibly with the addition of other insoluble inert fillers, which are then diluted before application. For example, active ingredients are typically available in the form of suspension concentrates (SCs), wettable powders (WPs), or water-dispersible granules (WGs). However, due to the generally hydrophobic nature of active ingredients, the addition of a suitable dispersant is essential to achieve a homogeneous dispersion with minimal mixing, which may be easily achieved by hand or with minimal mechanical mixing. Furthermore, once a homogeneous dispersion is achieved, the resulting suspension must remain stable for at least a sufficient time to allow application by conventional means, such as spraying. Settling, clumping, or flocculation of finely divided solids can result in inconsistent and ineffective application and clogging of spray equipment. Therefore, there is a need to provide dispersants that provide homogeneous dispersions and suspensions that maintain the stability of the aqueous dispersion during application.

[0005] Dispersants currently used for SC formulations include ethylene oxide / propylene oxide block copolymer surfactants based on a hydrophobic moiety and ethylene oxide. Nonionic surfactants, particularly ether phosphate derivatives of tristyrylphenol ethoxylate, are also used. Traditional anionic surfactants in use include sulfonated derivatives of aryl formaldehyde condensates, polyacrylates, and lignosulfonates.

[0006] Dispersants for WP and WG formulations are typically limited by the essential requirements that the dispersant be solid at ambient temperature, not gel, and not dissolve the active ingredient. For these reasons, traditional nonionic surfactants are often inappropriate, and anionic dispersants are preferred. Known effective dispersants for WP and WG formulations include sulfonated alkylnaphthalene / formaldehyde condensate salts and lignosulfonate salts.

[0007] U.S. Patent No. 5,999,623 discloses comb polymers that have been found to function well as dispersants in a variety of applications, including in compositions containing water-insoluble pesticide active agents. Such comb polymers may be produced from the reaction of succinic anhydride-containing resins with amines. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] U.S. Patent No. 8,247,353 Summary of the Invention [Means for solving the problem]

[0009] The present disclosure provides a dispersant obtained from the reaction of a styrene maleic anhydride copolymer with a monofunctional polyalkylene glycol of formula (1): R 1 O-(C p H 2p O) z -[(EO) b -(AO)c ]-H (1) In the formula, R 1 is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; H is hydrogen, and at least one of b or c is greater than 0. In a specific aspect, at least b is greater than 0.

[0010] Dispersants of the present disclosure may be used in a variety of applications, such as in aqueous agricultural compositions to disperse pesticide active ingredients, and in pigment, ink, or dye formulations to disperse particulate solids. DETAILED DESCRIPTION OF THE INVENTION

[0011] When appearing herein, the term "comprising" and its derivatives do not exclude the presence of any additional component, step, or procedure, whether or not it is disclosed herein. For the avoidance of any doubt, all compositions claimed herein by use of the term "comprising" may include any additional additive, adjuvant, or compound, unless stated to the contrary. In contrast, when appearing herein, the term "consisting essentially of" excludes from the scope of the succeeding recitation other components, steps, or procedures, except those that are not essential to operability, and the term "consisting of," when used, excludes any component, step, or procedure not specifically delineated or listed. The term "or," unless otherwise stated, refers to the listed members individually and in any combination.

[0012] As used herein, the articles "a" and "an" refer to one or more than one (i.e., at least one) of the grammatical object of the article. By way of example, "a monofunctional polyalkylene glycol" means one monofunctional polyalkylene glycol or more than one monofunctional polyalkylene glycol. The phrases "in one aspect," "according to one aspect," and the like generally mean that the particular feature, structure, or characteristic that follows the phrase is included in at least one embodiment of the present disclosure and may be included in more than one embodiment of the present disclosure. Importantly, such phrases do not necessarily refer to the same embodiment. When the specification states that a component or feature "may," "can," "could," or "might" be included or have a characteristic, the particular component or feature need not be included or have the characteristic.

[0013] The term "alkyl," as used herein, refers to a branched or unbranched saturated hydrocarbon group of 1 to 30 carbon atoms, such as methyl ("Me"), ethyl ("Et"), n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. In some aspects, alkyl groups herein contain 1 to 12 carbon atoms. The term "lower alkyl" refers to an alkyl group of 1 to 7 carbon atoms, or in some aspects, 1 to 4 carbon atoms. The term "higher alkyl" refers to an alkyl group having more than 7 carbon atoms.

[0014] The term "alkyleneoxy" refers to a divalent saturated aliphatic hydrocarbyl group attached to oxygen, where the aliphatic hydrocarbyl group can have 2 to 5 carbons, either straight or branched. In one aspect, alkyleneoxy is selected from propyleneoxy and butyleneoxy.

[0015] The term "cycloalkyl" refers to a saturated cyclic alkyl group having 3 to 12 carbon atoms, such as cyclopropyl, cyclohexyl, and cyclooctyl, which may have suitable substituents on the ring.

[0016] The term "alicyclic alkyl" refers to a saturated or unsaturated monocyclic, bicyclic, or tricyclic ring system, each cyclic ring consisting of from 3 to 10 carbon atoms, optionally bearing suitable substituents on the ring.

[0017] The term "aromatic" refers to a planar cyclic hydrocarbon moiety of conjugated double bonds, which may contain a single ring or multiple fused or covalently linked rings, e.g., 2, 3, or 4 fused rings. The term aromatic also includes alkylaryl.

[0018] The term "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur, and that the description includes both cases where the event or circumstance occurs and cases where it does not occur. For example, the phrase "optionally substituted alkyl" means that the alkyl group may or may not be substituted, and that the description includes both unsubstituted alkyl and alkyl where substitution is present.

[0019] The term "Ostwald ripening" refers to the coarsening of precipitates or solid particles dispersed in a medium, and is the final stage of phase separation in a solution, during which larger particles of the precipitate or solid particles grow at the expense of smaller particles, which disappear.

[0020] The term "suspension concentrate composition" or "SC" and derivatives refer to a composition comprising finely divided solid particles of an active ingredient, such as a pesticide, dispersed in a fluid medium, such as water, wherein the particles retain their identity and may be physically separated from the fluid medium.

[0021] The term "wettable powder" or "WP" is intended to refer to a formulation consisting of an active ingredient (e.g., a pesticide) in finely divided form combined with different adjuvants (e.g., wetting agents, stabilizers) and extenders. Dispersants may be used to facilitate the dispersion of the wettable powder in a fluid medium, such as water.

[0022] The term "water-dispersible granules" refers to active ingredient-containing formulations, such as agricultural pesticide formulations, that are in the granular phase and may be used after dilution with a fluid medium, such as water. A dispersant may be used to facilitate dispersion of the water-dispersible granules in the fluid medium.

[0023] The term "pesticide" refers to at least one pesticide selected from the group consisting of fungicides, insecticides, nematicides, herbicides, safeners, plant growth regulators, and mixtures thereof. In a particular aspect, the pesticide is selected from the group consisting of fungicides, insecticides, herbicides, and mixtures thereof. Those skilled in the art are familiar with such pesticides, which can be found, for example, in Pesticide Manual, 15th Ed. (2011), The British Crop Protection Council, London.

[0024] "Fungicide" means an active ingredient that kills, controls, or adversely modifies the growth of fungal pathogens. Examples of fungicides that may be used in this disclosure are: (3-ethoxypropyl)-mercuric bromide, 2-methoxyethylmercuric chloride, 2-phenylphenol, 8-hydroxyquinoline sulfate, 8-phenylmercuryoxyquinoline, acibenzolar, acibenzolar-S-methyl, acipetax, acipetax-copper, acipetax-zinc, aldimorph, allyl alcohol, and ametoctra. azin, amisulbrom, ampropylphos, anilazine, aureofungin, azaconazole, adithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentalon, benthiavalicarb, benthiavalicarb-isopropyl, benzalkonium chloride, benzamacryl, benzamacryl-isobutyl, benzamorph, benzohydroxamic acid, bethoxadin, binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin -S, Bordeaux mixture, boscalid, bromuconazole, bupirimate, Burgundy mixture, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, Cheshunt mixture, chinomethionate, clobenziazone, chloraniformethane, chloranil, chlorphenazole, chlorodinitronaphthalene, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlorozolinate , clivazol, clotrimazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper zinc chromate, cresol, khuflaneb, kuprovam, cuprous oxide, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, dazomet, dazomet-sodium, DBCP, debacarb, decafentin, dehydroacetic acid, dichlorofluanid, dichloron, dichlorophen, dichlorozoline, diclobutrazol, diclo Cymet, diclomedine, diclomedine-sodium, dicloran, diethofencarb, diethyl pyrocarboxylate, difenoconazole, diflumetrim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfone, dinotervon, diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, dodemorph,Dodemorph acetate, dodemorph benzoate, dodisin, dodisin sodium, dodine, drazoxolone, edifenphos, epoxiconazole, etaconazole, ethem, ethaboxam, ethirimol, ethoxyquin, ethylmercury 2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpic Ronil, fenpropidin, fenpropimorph, fentin, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetober, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxaproxad, folpet, formaldehyde, fucetyl, fucetyl-aluminum, fuberidazole, furalaxyl, furametpyr, fluka Irvanil, fluconazole, fluconazole-cis, furfural, flumecyclox, furofanate, gliodin, griseofulvin, guazatine, halacrynate, hexachlorobenzene, hexachlorobutadiene, hexaconazole, hexylthiophos, hydralgafen, hymexazole, imazalil, imazalil nitrate, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tribesylate, iodomethane, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiola phenanthrene, isopyrazam, isotianil, isovalerion, kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzide, mepanipyrim, mepronil, meptyldinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metazoxolone, metconazole, metasulfocarb, metofloxam, methyl bromide, methyl isothiocyanate, methylmercuric benzoate, methylmercuric dicyandiamide,Me, Mercury pentachlorophenoxide, metiram, metominostrobin, metrafenone, metulhobax, milneb, myclobutanil, myclozolin, N-(ethylmercury)-p-toluene-sulfonanilide, nabam, natamycin, nitrostyrene, nitrotar-isopropyl, nuarimol, OCH, octhilinone, ofrace, orysastrobin, oxadixyl, oxine-copper, oxypoconazole, oxypoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenoxide ol, penthiopyrad, phenylmercuric urea, phenylmercuric acetate, phenylmercuric chloride, phenylmercuric derivatives of pyrocatechol, phenylmercuric nitrate, phenylmercuric salicylate, phosdifen, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, polyoxorim-zinc, potassium azide, potassium polysulfide, potassium thiocyanate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazide, prothiocarb, prothiocarb hydrochloride, prothiocarb Tioconazole, pyracarbollide, pyraclastrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinnitrile, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, pyroxychlor, pyroxiflur, quinacetol, quinacetol sulfate, quinazamide, quinconazole, quinoxyfen, quintozene, labenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium azide, sodium orthophenylphenoxide, sodium pentachlorophenoxide Cid, sodium polysulfide, spiroxamine, streptomycin, sulfur, sultropene, TCMTB, tebuconazole, tebufloquine, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thithiofen, thifluzamide, thiochlorfenfim, thiomersal, thiophanate, thiophanate-methyl, thioquinox, thiram, tiadinil, thioximide, turkfos-methyl, trifluanid, tolylmercuric acetate, triadimefon, triadimenol, triamiphos, triarimol, triazbutyl,Including, but not limited to, triazoxide, tributyltin oxide, triclamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, uniconazole-P, validamycin, valifenalate, vinclozolin, zaliramide, zinc naphthenate, zineb, ziram, zoxamide and mixtures thereof.

[0025] "Insecticide" means an active ingredient that kills, controls, or adversely modifies the growth of insects. Examples of insecticides that may be used in this disclosure are: 1,2-dichloropropane, abamectin, acephate, acetamiprid, acetione, acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, alixycarb, α-cypermethrin, α-ecdysone, α-endosulfan, amidithione, aminocarb, amithroxane ... , amiton oxalate, amitraz, anabasine, atidathion, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azotoate, barium hexafluorosilicate, barthrin, bendiocarb, benfuracarb, bensultap, β-cyfluthrin, β-cypermethrin, bifenthrin, bioallethrin, bioethanomethrin, biopermethrin bistrifluoroone, borax, boric acid, bromfenvinphos, bromocyclen, bromo-DDT, bromophos, bromophos-ethyl, bufencarb, buprofezin, butacarb, butathiophos, butocarboxim, butonate, butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide, camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothione, carbosulfan, cartap, cartap hydrochloride, chlorantraniliprole, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform hydrochloride, chlorethoxyphos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroform, chloropicrin, chlorphoxim, chlorpyrazophos, chlorpyrifos Rifos, chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I, cinerin II, cinerins, cismethrin, cloetocarb, closantel, clothianidin, copper acetoarsenate, copper arsenate, copper naphthenate, copper oleate, coumaphos, coumitoate, crotamiton, crotoxyphos, crufomate, cryolite, cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyclethrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, chromazine, cythio ate, DDT, decarbofuran, deltamethrin, demefion, demefion-O, demefion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulfone, diafenthiuron, dialifos, diatomaceous earth, diazinon, dikapton, dichlorophenthion, dichlorvos, dicresyl, dicrotophos, dicyclanil, dieldrin, diflubenzuron, dilol, dimefluthrin, dimefox, dimethane, dimethoate, dimethrin, dimethylvinphos, di Methylan, Zinex, Zinex-diclexin, Dinoprop, Dinosam, Dinotefuran, Diofenolan, Dioxabenzophos, Dioxacarb, Dioxathion, Disulfoton, Dicyclophos, d-Limonene, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, Doramectin, Ecdysterone, Emamectin, Emamectin Benzoate, EMPC, Empenthrin, Endosulfan, Endothion, Endrin, EPN, Epofenonane, Eprinomectin, Esdepallethrin e), esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, ethoate-methyl, ethoprophos, ethyl formate, ethyl-DDD, ethylene dibromide, ethylene dichloride, ethylene oxide, etofenprox, etrimphos, EXD, famfar, fenamiphos, fenazaflor, fenchlorphos, fenetacarb, fenfluthrin, fenitrothion, fenobucarb, fenoxacrim, fenoxycarb, fenpyrithrin, fenpropathrin, fensulfothion, fenthion, fenthion-ethyl,Fenvalerate, fipronil, flonicamid, flubendiamide, flucofuron, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, fluvalinate, fonofos, formetanate, formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosmetilan, fospirate, fostietan, fufenozide, furathiocarb, frethrin, γ-cyhalothrin, γ-HCH, halfenprox, halofenozide, HCH, HEOD, heptachlor, heptenofos, heterophos s, hexaflumuron, HHDN, hydramethylnon, hydrogen cyanide, hydroprene, hikincarb, imidacloprid, imiprothrin, indoxacarb, indomethane, IPSP, isazophos, isobenzan, isocarbophos, isodrin, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane, isothioate, isoxathion, ivermectin, jasmolin I, jasmolin II, jodofenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, kereban, kinoprene, λ-cyhalothrin, lead arsenate, Pimectin, leptophos, lindane, lilimphos, lufenuron, ritidathion, malathion, malonoben, magidox, mecarbam, mecarfone, menazone, meperfluthrin, mefosoran, mercurous chloride, mesulfenphos, metaflumizone, methacrifos, methamidophos, methidathion, methiocarb, methoclotophos, methomyl, methoprene, methotrin, methoxychlor, methoxyfenozide, methyl bromide, methyl isothiocyanate, methylchloroform, methylene chloride, metofluthrin, metolcarb, metoxadiazone, mevinphos, Mexacarbate, milbemectin, milbemycin oxime, mipafox, mirex, morosultap, monocrotophos, monomehypo, monosultap, morphothion, moxidectin, naphthalophos, naled, naphthalene, nicotine, nifluridide, nitenpyram, nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeprophos, oxydisulfoton, para-dichlorobenzene, parathion, parathion-methyl, penfluoron, pentachlorophenol, permethrin,Fencaptone, Fenoto, Phosphorus, phenthoate, phorate, phosalone, phospholane, phosmet, phosnichlor, phosphamidon, phosphine, phoxim, phoxim-methyl, pyrimetaphos, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, primidophos, profenofos, profluralin, profluthrin, promacyl, promecarb, propafos, propetamfos, propoxar, prothidathion, prothiofos, prothoate, pro Trifenbut, pymetrozine, pyraclofos, pyrafluprole, pyrazophos, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins, pyridaben, pyridalyl, pyridaphenthion, pyrifluquinazon, pyrimidifen, pirimitate, pyriprole, pyriproxyfen, quasia, quinalphos, quinalphos-methyl, quinothione, lafoxanide, resmethrin, rotenone, riania, sabadila, shradan, selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride, hexaflu Sodium orosilicate, sodium thiocyanate, sofamid, spinetoram, spinosad, spiromesifen, spirotetramat, sulcofuron, sulcofuron-sodium, sulfuramide, sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, tau-fluvalinate, thazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, teralethrin, terbufos, tetrachloroethane, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, θ-citra Permethrin, thiacloprid, thiamethoxam, cyclofos, thiocarboxim, thiocyclam, thiocyclam oxalate, thiodicarb, thiofanox, thiometon, thiosultap, thiosultap-disodium, thiosultap-monosodium, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, triatene, triazamate, triazophos, trichlorfon, trichlormethaphos-3, trichloronat, tripenofos, triflumuron, trimethacarb, triplen, vamidothion,Including, but not limited to, vaniliprole, XMC, xylylcarb, zeta-cypermethrin, zolaprofos and mixtures thereof.

[0026] "Herbicide" means an active ingredient that kills, controls, or adversely alters the growth of plants. Examples of herbicides that can be used in this disclosure are: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, arorac, ametridione, ametryn, amivudine, amicarbazone. , amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprophos-methyl, amitrole, ammonium sulfamate, anilofos, anisrone, asulam, atraton, atrazine, azafenidine, azimsulfuron, aziprothrin, barban, BCPC, beflubutamid, benzoline, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulide, bentazon, benzadox, benzfendizone, benzipram , Benzobicyclon, Benzofenap, Benzofluor, Benzoylprop, Benzthiazuron, Bicyclopyrone, Bifenox, Viranafos, Bispyribac, Borax, Bromacil, Bromobonyl, Bromobutide, Bromofenoxime, Bromoxynil, Brompyrazone, Butachlor, Butafenacil, Butamifos, Butenachlor, Butidazole, Buthiuron, Butralin, Butroxydim, Buturon, Butyrate, Cacodylic Acid, Cafenstro ol, calcium chlorate, calcium cyanamide, cambenziclor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone, CDEA, CEPC, chlormethoxyfen, chloramben, chloranocryl, chlorradifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, Chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, chloransulam, CMA, copper sulfate, CPMF, CPPC, cledazine, cresol, cumyluron, cyanatrin, cyanazine, cycloate, cyclosulfamuron, cycloxamuron Shijim, Cycluron, Cyhalofop, Cyperquat, Cyprazine, Cyprazole, Cypromide, Dimron, Dalapon, Dazomet, Delaclor, Desmedipham, Desmetrin, Diallate, Dicamba, Dichlobenil, Dichloralurea, Dichlormate, Dichlorprop, Dichlorprop-P, Diclofop, Diclosulam, Diethamquat, Diethathyl, Difenopentene, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Dimefron, Dimepiperate, Dimethachlor, Dimethamethrin, Dimethenamid, Dime Tenamide-P, dimexano, dimidazon, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinadin, endothal, epronaz, EPTC, ervon, esprocarb, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethofumesate, ethoxyfen, ethoxysulfuron, ethinofen, etonipromide, etobenzanide, EXD, fenasulam, fenopro Fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropin, flumeturon, fluorodifen, fluoroglycofen,Fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, fluorochloridone, fluoroxypyr, flurtamone, fluthiacetate, fomesafen, foramsulfuron, fosamine, furiloxifene, glufosinate, glufosinate-P, glyphosate, halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazamethabenz Xapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobornyl, iodomethane, iodosulfuron, ioxinil, ipazine, ipfencarbazone, iprimidum, isocarbamide, isosyl, isomethiozine, isonoruron, isoporinate, isoproparin, isoproturon, isouron, isoxaben, isoxachlorthor, isoxaflutole, isoxapyrifop, carbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethionyl MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidid, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metofluran, methabenzthiazuron, methaproparin, methazole, methiobencarb, methiozoline, methiuron, methometon, metoprothrin, methyl bromide, methyl isothiocyanate, methyldimuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron Molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, naptalam, nebron, nicosulfuron, nipiraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, norlon, OCH, orbencarb, orthodichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefon, oxyfluorfen, parafluoron, paraquat, pebulate,pelargon, Acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, fenisofaam, phenmedipham, phenmedipham-ethyl, fenobenzuron, phenylmercuric acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazin, prodiamine, profluazole, profluralin, profoxydim, proglinadin, prometon, prometryn, propacrol, Propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfarin, prosulfocarb, prosulfuron, proxan, prinachlor, pidanone, pyraclonil, pyraflufen, pyrasulfotole, pyrazolinate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafor, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, quinclorac , quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P, rodetanil, rimsulfuron, saflufenacil, S-metolachlor, sebutylazine, secbumeton, sethoxydim, ciduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfurate, sulfentrazone, sulfometuron, sulfosulfuron, sulfate, sulglicapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terba Sil, terbucarb, terbuchlor, terbumeton, terbutylazine, terbutryn, tetrafluoroone, thenylchlor, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, thiocarbazil, thiochlorim, topramezone, tralkoxydim, tri-alate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, tridifen, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, triphop, trifopsim,Including, but not limited to, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylaclor and mixtures thereof.

[0027] "Safener" means an active ingredient that is applied together with a herbicide to protect crops from damage. Some safeners that can be used in the present disclosure include, but are not limited to: benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, dymron, dichlormid, dicyclonone, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148, N-phenylsulfonylbenzoic acid amide, and mixtures thereof.

[0028] "Nematicide" means an active ingredient that has an effect against agriculturally relevant nematodes, for example, reducing damage caused by agriculturally relevant nematodes. Examples of nematicides that may be used in the present disclosure include, but are not limited to, avermectins (e.g., abamectin), carbamate nematicides (e.g., aldicarb, thiadicarb, carbofuran, carbosulfan, oxamyl, aldoxycarb, ethoprop, methomyl, benomyl, alanycarb), organophosphate nematicides (e.g., fenamiphos (fenamiphos), fensulfothion, terbufos, fosthiazate, dimethoate, phosphocarb, diclofenthion, isamidophos, fosthietane, isazophos, ethoprophos, cadusafos, terbufos, chlorpyrifos, diclofenthion, heterophos, isamidophos, mecarfone, phorate, thionazine, triazophos, diamidaphos, fosthietane, phosphamidon, captan, and mixtures thereof.

[0029] "Plant growth regulator" means an active ingredient used to affect the growth characteristics of plants. Examples of plant growth regulators that may be used in the present disclosure are: 1-naphthaleneacetic acid, 1-naphthaleneacetic acid K-salt, 1-napthol, 2,4-dichlorophenyloxyacetic acid (2,4-D), 2,4-DB, 2,4-DEP, 2,3,5-triiodobenzoic acid, 2,4,5-trichlorophenyloxyacetic acid, 2-naphthoxyacetic acid, 2-naphthoxyacetic acid sodium salt, 3-chloro-4-hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4-chlorophenyloxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6-benzylaminopurine, Auxindole, α-naphthaleneacetic acid K-salt, β-naphthoxyacetic acid, p-chlorophenyloxyacetic acid, dicamba, dichlorprop, fenoprop, indole-3-acetic acid (IAA), indole-3-acetate, Indole-3-acetyl-DL-aspartic acid, indole-3-acetyl-DL-tryptophan, indole-3-acetyl-L-alanine, indole-3-acetyl-L-valine, indole-3-butyric acid (IBA), indole-3-butyric acid K-salt, indole-3-propionic acid; α-naphthaleneacetic acid, indole-3-methyl acetate, naphthaleneacetamide, naphthaleneacetic acid (NAA), phenylacetic acid, picloram, potassium naphthenate, sodium naphthenate, 4-hydroxyphenethyl alcohol, 4-CPPU, 6-benzylaminopurine (BA), 6-(Y,Y-dimethylallylamino)purine (2iP), 2-iP-2HCl, adenine, adenine hemisulfate, benzyladenine, kinetin, meta-topolin, N6-benzoyladenine, N-benzyl-9-(2-tetrahydropyranyl)adenine (BP) A), N-(2-chloro-4-pyridyl)-N-phenylurea, gibberellic acid (GA3), gibberellin, gibberellin A4 + A7 (GA 4 / 7 ), ethylene and abscisic acid.

[0030] The term "target substrate" refers to the locus beneath the leaves of a plant that is the intended destination of a pest control agent, including, but not limited to, natural surfaces such as soil, water (lakes, ponds, marshes, swamps, streams, puddles, etc.), and man-made surfaces such as paved roads; pests; or combinations thereof.

[0031] "Pests" generally include insects, mites, ticks and other arthropods; disease agents such as fungi, protozoa, bacteria and viruses; parasitic helminths, nematodes (nematodes), cestodes (tapeworms), platyhelminths (flatworms), trematodes (flukes) and other helminths; spore-forming parasites; slugs and snails; and vertebrates such as birds, rodents or other vertebrates that can directly or indirectly damage or cause disease or damage to any plant or part thereof, or any processed, manufactured or other plant product.

[0032] A "pesticidally effective amount" refers to the amount of pesticide that, after application, reduces the presence of a pest or increases the plant's resistance to the pest.

[0033] According to one aspect, the present disclosure provides a dispersant obtained from the reaction of a styrene maleic anhydride copolymer with a monofunctional polyalkylene glycol of formula (1): R 1 O-(C p H 2p O) z -(EO) b -(AO) c ]-H (1) In the formula, R 1is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; H is hydrogen, and at least one of b or c is greater than 0. In a specific aspect, at least b is greater than 0.

[0034] Styrene maleic anhydride copolymer is made using styrene and maleic anhydride monomers. In various aspects, the styrene maleic anhydride copolymer is a polymer formed according to the formula [ka] and a first building block of the formula [ka] wherein each of m and x is independently a real number representing the mole fraction of each constitutional unit in the styrene maleic anhydride copolymer, and each R is independently hydrogen, an aryl group, or an aliphatic group. As used herein, "constitutional unit" refers to the smallest constitutional unit (a group of atoms that constitutes part of the essential structure of a macromolecule), or monomer, the repeating units of which make up a macromolecule, e.g., a polymer.

[0035] In various aspects, the mole fraction m is in the range of about 0.5 to about 0.9, the mole fraction x is in the range of about 0.1 to about 0.5, and (m + x) = 1.00. In another aspect, the mole fraction m is in the range of about 0.8 to about 0.9, the mole fraction x is in the range of about 0.1 to about 0.2, and (m + x) = 1.00. In aspects of the present disclosure, m and x are each greater than 0. For each R group, examples of aromatic groups include, but are not limited to, phenyl, biphenyl, naphthyl, substituted phenyl or biphenyl, and naphthyl. Examples of aliphatic groups include, but are not limited to, alkyl and alicyclic alkyl.

[0036] The styrene-maleic anhydride copolymers that may be used in the present disclosure can be selected from one styrene-maleic anhydride copolymer or a mixture of styrene-maleic anhydride copolymers, and have a molar ratio of styrene to maleic anhydride of at least 4.0:1.0, or in another aspect at least 5.0:1.0, while in yet another aspect at least 6.0:1.0, and in yet a further aspect at least 7.0:1.0. In contrast to what is generally taught about state-of-the-art dispersants, applicant has unexpectedly discovered that a styrene to maleic anhydride ratio of at least 4.0:1.0 can be important for the ability of the dispersants of the present invention to enable grinding of pesticide suspension concentrate compositions, minimize the viscosity of concentrated particle suspensions at elevated temperatures while under constant shear, and reduce or prevent Ostwald ripening of slightly water-soluble pesticides.

[0037] According to another aspect, the styrene maleic anhydride copolymers that may be used in the present disclosure can be selected from one styrene maleic anhydride copolymer or a mixture of styrene maleic anhydride copolymers, and have a molar ratio of styrene to maleic anhydride in the range of 4.0:1.0 to 8.0:1.0, and in another aspect in the range of 6.0:1.0 to 8.0:1.0. Has.

[0038] According to another aspect, the styrene maleic anhydride copolymers that may be used in the present disclosure can be selected from a single styrene maleic anhydride copolymer or a mixture of styrene maleic anhydride copolymers and have a weight average molecular weight (Mw) of less than 50,000 grams per mole (g / mol), in another aspect less than 20,000 g / mol, and in yet a further aspect less than 15,000 g / mol. The weight average molecular weight can be determined by gel permeation chromatography (GPC).

[0039] According to another aspect, other monomers besides styrene may be incorporated into the backbone of the styrene-maleic anhydride copolymer. Generally, suitable monomers have a low molecular weight (e.g., less than 50,000 g / mol) so as to keep the total molecular weight of the final polymer relatively low, thereby maintaining the final polymer relatively water-soluble. Possible monomers that may be present in addition to styrene include olefins such as ethylene, conjugated dienes such as 1,3-butadiene and isoprene, acrylic acid, alkyl acrylates and methacrylates, particularly lower alkyl and ethylhexyl esters such as methyl, ethyl, and butyl, vinyl acetate, acrylonitrile, methacrylonitrile, acrylamide, methacrylamide, unsaturated ethers such as alkyl vinyl ethers, e.g., methyl and ethyl ethers, AMPS, α-methylstyrene, and hydroxyethyl methacrylate.

[0040] Commercially available styrene maleic anhydride resins that may be used include, but are not limited to, XIRAN® resins available from Polyscope Polymers, such as XIRAN® EF-40 resin and XIRAN® EF-60 resin.

[0041] In the monofunctional polyalkylene glycol of formula (I) reacted with the styrene maleic anhydride copolymer, R 1 Alcohol R 1 -OH represents an alkyl or aromatic radical, and the alcohol R 1 The -OH is used as a starter alcohol that reacts (alkoxylates) with ethylene oxide and / or alkylene oxide to produce the monofunctional polyalkylene glycol of formula (1).

[0042] According to one aspect, the starting alcohol R 1 OH is a short chain aliphatic alcohol, R 1is a lower chain alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 3-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl -1-methylpropyl, 1-ethyl-2-methylpropyl, 2-ethyl-1-methylpropyl, 2-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3,4-dimethylpentyl, 4,4-dimethylpentyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 4-ethylpentyl, 1,1,2-trimethylbutyl, 1,1,3-trimethylbutyl, 1,2,2-trimethylbutyl, 1,2,3-trimethylbutyl It may represent trimethylbutyl, 1,3,3-trimethylbutyl, 1-ethyl-1-methylbutyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-methylbutyl, 2-ethyl-2-methylbutyl, 2-ethyl-3-methylbutyl, 3-ethyl-1-methylbutyl, 3-ethyl-2-methylbutyl, 3-ethyl-3-methylbutyl, 1-propylbutyl, 2-propylbutyl, 3-propylbutyl, 1-butylpropyl, 2-butylpropyl, 1-propyl-1-methylpropyl, 1-propyl-2-methylpropyl, 2-propyl-1-methylpropyl, 2-propyl-2-methylpropyl, 1,1-diethylpropyl or 1,2-diethylpropyl.

[0043] According to yet another aspect, the starting alcohol R 1 -OH is a cycloaliphatic or aromatic alcohol, and R 1 may represent cyclohexanyl, phenyl, benzyl and cresyl isomers.

[0044] According to yet another aspect, the starting alcohol may be a mixture of any of the above starting alcohols (i.e., a mixture of any of short chain alcohols, long chain alcohols, cycloaliphatic alcohols, and aromatic alcohols).

[0045] Starting alcohol R 1 -OH may be linear (straight-chain), branched or cyclic. If branched, the main chain of the alcohol moiety may, according to certain aspects, have, as a rule, 1 to 4 branches. Each independent branch may have 1 to 10, or 1 to 6, or even 1 to 4 carbon atoms. Particular branches may contain methyl, ethyl, n-propyl or isopropyl groups.

[0046] According to one aspect, the starting alcohol R 1 -OH can be a linear short chain alcohol, such as methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol, or n-heptanol.1 -OH may be an aromatic alcohol, such as phenol, benzyl alcohol, or cresyl alcohol.

[0047] In one particular aspect, z represents 0 in the monofunctional polyalkylene glycol of formula (I).

[0048] In aspects where z represents 1, 2 or 3 in the monofunctional polyalkylene glycol of formula (1), such glycols may be, for example, those represented by formula (2): R 1 -O-(C p H 2p O) q -H (2) (In the formula, R 1 , p and z are as defined above with ethylene oxide and / or alkylene oxide.) The compounds of formula (2) may in particular be mono-C1-C7 alkyl ethers of ethylene glycol (p=2; z=1), propylene glycol (p=3; z=1), diethylene glycol glycol (p=2; z=2), dipropylene glycol (p=3; z=2), triethylene glycol (p=2; z=3) or tripropylene glycol (p=3; z=3), which are known per se.

[0049] Of particular importance, according to one aspect of the present disclosure, the starting alcohol has the formula (2a): R 1 -O-(CH2CH(CH3)O) z -H" (2a) (In the formula, R 1 represents C1-C7 alkyl, and z is as defined herein. are alkyl ethers of mono-, di-, and tripropylene glycol.

[0050] Another aspect is a mono-C1-C4 alkyl ether (i.e., R 1 particularly represents C1-C4 alkyl), and among these, particularly dipropylene glycol monoalkyl ether ( Emphasis is placed on dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether and dipropylene glycol mono-n-butyl ether, among others.

[0051] The alkoxylation is carried out by reacting the starting alcohol R 1 They are the result of the reaction of -OH with ethylene oxide (EO) and / or other alkylene oxides (AO), such as alkylene oxides having 3 to 6 carbon atoms. In this context, the following alkylene oxides may be mentioned in particular: 1,2-propylene oxide (PO), 1,2-butylene oxide (BO), 1,2-pentylene oxide (PeO) and 1,2-hexylene oxide (HO). A particularly preferred alkylene oxide is 1,2-propylene oxide (PO).

[0052] Each degree of alkoxylation is a result of the amount of ethylene oxide and / or other alkylene oxide charged and the reaction conditions selected for the reaction (alkoxylation), the former being, in principle, a statistical average since the number of ethylene oxide and / or alkylene oxide units in the monofunctional polyalkylene glycol is a result of reaction variability.

[0053] The degree of alkoxylation, i.e., the average chain length of the polyether chains of the polyalkylene glycols according to the present disclosure, and their composition (in other words, the values ​​of b and c) can be controlled by the molar ratio of the starting alcohol to EO and / or AO used in their preparation and the reaction conditions. In most aspects, the monofunctional polyalkylene glycol of formula (1) may have at least about 2, or at least about 4, particularly at least about 5, particularly at least about 6, 7, or 8, and particularly preferably at least about EO and AO units (b + c). According to a further aspect, the monofunctional polyalkylene glycol of formula (1) may have up to about 100, or up to about 80, particularly up to about 60, particularly up to about 40, and particularly up to about 30 EO and AO units (b + c). In aspects where c is 0, the monofunctional polyalkylene glycol of formula (1) may have at least about 2, or at least about 4, particularly at least about 5, particularly at least about 6, 7 or 8, and particularly preferably at least about 10 EO units, and according to a further aspect, the polyalkylene glycol of formula (1) may have up to about 100, or up to about 80, particularly up to about 60, particularly up to about 40, and particularly preferably up to about 30 EO units. Thus, the degree of alkoxylation (b+c) may range from about 2 to 100, or from about 4 to 80, or from about 5 to 60, or from about 6, 7 or 8 to 40, or from about 10 to 30.

[0054] In one aspect, the monofunctional polyalkylene glycol of formula (I) used to react with the styrene maleic anhydride copolymer has a value of b greater than the value of c. These are monofunctional polyalkylene glycols that contain more EO units than AO units. Thus, in some aspects, the monofunctional polyalkylene glycol of formula (1) may have a ratio of EO to AO units of at least 2:1, or at least 3:1, or at least 5:1, or at least 10:1, or at least 15:1, or at least 20:1, or even at least 30:1.

[0055] Starting alcohol R 1The reaction of --OH (or mixture of starting alcohols) with ethylene oxide and / or alkylene oxide is carried out by conventional methods known to those skilled in the art and in equipment conventionally used for this purpose.

[0056] Alkoxylation can be catalyzed by strong bases such as alkali and alkaline earth metal hydroxides, Bronsted acids, or Lewis acids such as AlCl, BF, etc. Catalysts such as hydrotalcite or DMC may be used for narrow distribution alcohol alkoxylates.

[0057] The alkoxylation is preferably carried out at a temperature in the range of about 80°C to 250°C, or about 100°C to 220°C. The pressure is preferably between ambient and 600 bar. If desired, the ethylene oxide and / or alkylene oxide may comprise an admixture of, for example, about 5-60% of an inert gas.

[0058] In formula (I), the ethylene oxide and alkylene oxide units can be arranged as desired. Thus, the structural unit [(EO) b -(AO) c ] may be a homopolymer, random copolymer, gradient copolymer, alternating copolymer, or block copolymer composed of ethylene oxide and / or alkylene oxide units. In a particular aspect, the block copolymer composed of ethylene oxide and alkylene oxide units comprises terminal ethylene oxide units. According to one aspect, the monofunctional polyalkylene glycol of formula (1) is preferably ethoxylated or comprises at least one ethylene oxide block. In a further aspect, the monofunctional polyalkylene glycol of formula (1) is propoxylated or has at least one propylene oxide block. In yet a further aspect, the monofunctional polyalkylene glycol of formula (1) is ethoxylated and propoxylated and comprises terminal ethylene oxide units.

[0059] In one aspect, the theoretical molecular weight of the monofunctional polyalkylene glycol of formula (1) may be 5000 g / mol or less, 4000 g / mol or less, or 3000 g / mol or less, or even 2500 g / mol or less. In certain aspects, the theoretical molecular weight of the monofunctional polyalkylene glycol of formula (1) is in the range of about 750 g / mol to about 5000 g / mol.

[0060] The reaction of the styrene-maleic anhydride copolymer with the monofunctional polyalkylene glycol of formula (1) can be carried out in the presence of a base. In one aspect, the base can be sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, silver hydroxide, zinc hydroxide, ammonium hydroxide, magnesium hydroxide, barium hydroxide, strontium hydroxide, cesium hydroxide, rubidium hydroxide, ammonium carbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, silver carbonate, lithium carbonate, lithium bicarbonate, barium bicarbonate, magnesium carbonate, cesium carbonate, hydrates thereof, and trialkylamines such as triethylamine and tributylamine.

[0061] The reaction of the styrene-maleic anhydride copolymer with the monofunctional polyalkylene glycol of formula (I) may also be carried out in the presence of a solvent. The solvent may be non-reactive with the copolymer resin and the monofunctional polyalkylene glycol. In some aspects, the solvent is aprotic. For example, the solvent may be an aromatic solvent such as benzene, an alkylbenzene such as toluene and xylene, an ether such as methyl t-butyl ether, a ketone such as methyl isobutyl ketone, an ester such as ethyl acetate and propyl acetate, a carbonate such as ethylene carbonate, propylene carbonate, and butylene carbonate, a halogenated aliphatic hydrocarbon such as dichloromethane, a lactone such as butyrolactone, and an aliphatic nitrile such as butyronitrile. Mixtures of solvents may also be used. Cosolvents may also be used to change the properties of the solvent or solvent mixture. The solvent may be used in an amount sufficient to dissolve the copolymer resin and, optionally, the reaction product of this disclosure. The amount of solvent used may vary widely, as will be apparent to those skilled in the art, and may be any amount appropriate for producing the reaction product.

[0062] In one aspect, the dispersant obtained from the reaction of a styrene maleic anhydride copolymer with a monofunctional polyalkylene glycol of formula (1) where b is greater than 0 and c is 0 has the formula (3): [ka] (In the formula, R 1 is as defined above, Z is hydrogen, a monovalent metal ion, or an amine, and Y and D vary depending on the reactant selected.

[0063] In some aspects, the dispersant comprises the reaction product in an anionic form, which may optionally be converted to the formed acid by the addition of an acid known to those skilled in the art. However, it has been found that the anionic form of the reaction product surprisingly works well and may not require an additional step of converting it to the acid form. Thus, according to one particular aspect, the dispersant consists essentially of the reaction product in its anionic form. In yet another aspect, the dispersant consists essentially of the reaction product in its acid form.

[0064] Dispersants may be made by dissolving a styrene-maleic anhydride copolymer in a non-reactive solvent, such as propylene carbonate, and reacting this mixture with the desired monofunctional polyalkylene glycol of formula (1) at a temperature ranging from about 35°C to about 150°C, optionally in the presence of a base. The resin and solvent may be heated to about 60°C before adding the monofunctional polyalkylene glycol of formula (1), thereby promoting a more rapid reaction. The order of addition is not believed to be important, and thus the anhydride resin may be added to the monofunctional polyalkylene glycol. In some aspects, the ratio of the amount of styrene-maleic anhydride copolymer to the amount of monofunctional polyalkylene glycol in the reaction mixture is greater than 1:1, for example, greater than 1.25:1, or even greater than 1.5:1. However, it is believed that excellent dispersants can be formed with amounts greater or less than the stoichiometric amounts noted above. The non-reactive solvent may act as a processing aid to simplify the synthesis of the dispersant product. A base may act as a catalyst to increase the reaction rate. In some aspects, the solvent may remain in the dispersant product, while in other aspects, the solvent may be removed from the dispersant product. As much solvent as desired can be used / removed. Finally, the reaction product can be isolated and purified as desired using techniques well known in the art.

[0065] In some aspects, the dispersants of the present disclosure will have a maximum viscosity of 800 mPa at 25° C. In another aspect, the dispersants of the present disclosure may have a total solids content (%) of less than about 60, or less than about 55, or even less than about 50. In yet another aspect, the dispersants of the present disclosure have a total solids content (%) of less than about It may have a % total solids content of greater than 35, or greater than about 40, or even greater than about 45.

[0066] The dispersants of the present disclosure offer advantages over state-of-the-art dispersants prepared from styrene-maleic anhydride copolymers having molar ratios of styrene to maleic anhydride that deviate from those of the present invention, as agricultural compositions containing the dispersants of the present disclosure exhibit lower viscosity and improved performance at high temperatures. The dispersants of the present disclosure can also reduce or prevent Ostwald ripening, enabling high-shear grinding of pesticide suspension concentrate compositions and improving their suspendability when diluted in water before application to a substrate. Finally, the dispersants of the present disclosure may generate less foam when mixed with water than state-of-the-art dispersants.

[0067] According to another aspect, there is provided an aqueous agricultural composition comprising the dispersant of the present disclosure and a pesticide.

[0068] In some embodiments, the pesticide is poorly soluble in water. In these embodiments, the pesticide is water soluble at 20°C to a concentration of at most 10 g / L, preferably at most 3 g / L, and particularly at most 0.5 g / L. The pesticide is typically solid at 20°C. In some embodiments, the pesticide has a melting point of at least 50°C, or at least 80°C, particularly at least 120°C.

[0069] According to one embodiment, the aqueous agricultural composition comprises at least about 0.1 wt. % of dispersant, or at least about 0.5 wt. % of dispersant, or at least about 1 wt. % of dispersant, or at least about 3 wt. % of dispersant, or even at least about 5 wt. % of dispersant, based on the total weight of the aqueous agricultural composition.

[0070] In another embodiment, the aqueous agricultural composition comprises less than about 7% by weight of dispersant, or less than about 6% by weight of dispersant, or less than about 5% by weight of dispersant, or less than about 4% by weight of dispersant, or even less than about 3% by weight of dispersant, based on the total weight of the aqueous agricultural composition.

[0071] In yet another embodiment, the aqueous agricultural composition comprises from about 0.05% to 7% by weight of the dispersant, or from about 0.5% to 6% by weight of the dispersant, or from about 1% to 5.5% by weight of the dispersant, or even from about 3% to 5% by weight of the dispersant, based on the total weight of the aqueous agricultural composition.

[0072] The aqueous agricultural composition may also comprise at least about 0.5% by weight of a pesticide, hi some embodiments, the aqueous agricultural composition comprises at least about 2% by weight, or even at least about 5% by weight, of a pesticide, based on the total weight of the aqueous agricultural composition.

[0073] In another embodiment, the aqueous agricultural composition may comprise up to about 70% by weight, or up to about 65% by weight, or up to about 60% by weight, or up to about 50% by weight, or even up to about 40% by weight of the pesticide, based on the total weight of the aqueous agricultural composition. When the aqueous agricultural composition comprises an additional pesticide, the aforementioned amounts apply to the total amount of the pesticide and the additional pesticide.

[0074] At least one pesticide is present in the aqueous agricultural composition in suspended form. The additional pesticide may be present in suspended, emulsified, or dissolved form, with emulsified form being preferred. The additional pesticide may be selected from fungicides, insecticides, nematicides, herbicides, safeners, plant growth regulators, and mixtures thereof. Thus, in another aspect, there is provided an agrochemical suspension concentrate composition comprising: a) a continuous aqueous phase; b) a partially water-soluble pesticide; and c) a dispersant of the present disclosure.

[0075] The aqueous agricultural composition may further comprise at least about 10% by weight of water, or at least about 30% by weight, particularly at least about 45% by weight of water, based on the total weight of the aqueous agricultural composition. In another embodiment, the aqueous agricultural composition may comprise up to about 90% by weight of water, or even up to about 75% by weight of water, based on the total weight of the aqueous agricultural composition.

[0076] The aqueous agricultural composition may also contain agrochemical formulation adjuvants. Suitable formulation adjuvants include dispersants other than those disclosed herein, solvents, liquid carriers, solid carriers or fillers, surfactants, emulsifiers, wetting agents, solubility enhancers, penetration enhancers, protective colloids, stickers, thickeners, water-retaining agents, repellents, attractants, feed stimulants, compatibilizers, bactericides, antifreeze agents, foam suppressants, colorants, adhesives, and binders.

[0077] Aqueous pesticide compositions may be useful for controlling phytopathogenic fungi and / or undesirable plant growth and / or undesirable insect or mite attacks, and / or for regulating plant growth; the compositions may act on specific pests, their habitats, or plants to be protected from each pest, soil, and / or on undesirable plants and / or useful plants and / or their habitats. Furthermore, the use of aqueous pesticide compositions may control undesirable insect or mite attacks on plants, and / or plant pathogens, and / or undesirable plant growth, in which case seed material of useful plants is treated with the composition. Finally, aqueous pesticide compositions and suspension concentrate compositions may exhibit reduced Ostwald ripening. Thus, in another particular aspect, there is provided a suspension concentrate composition comprising: a) a continuous aqueous phase; b) a partially water-soluble pesticide; and c) a dispersant of the present disclosure, wherein the dispersant is present in an amount sufficient to reduce or prevent Ostwald ripening of the pesticide (b) in the composition, for example, an amount of at least about 1 wt. % dispersant, or at least about 3 wt. % dispersant, or even at least about 5 wt. % dispersant, based on the total weight of the suspension concentrate composition.

[0078] According to another aspect, the aqueous pesticide composition of the present disclosure may be used in conventional agricultural methods. For example, the aqueous agricultural composition may be applied to the desired target substrate after emergence by any means, such as an airplane spray tank, a knapsack spray tank, a cattle dipping vat, agricultural equipment used for ground spraying (e.g., a boom sprayer, a hand sprayer), etc.

[0079] According to another aspect, the technology disclosed herein provides a method for killing, inhibiting, or repelling pests, comprising the steps of providing a pesticidally effective amount of a pesticide; providing an effective amount of a dispersant of the present disclosure; combining the pesticide and optionally a fertilizer with the dispersant and water to prepare an aqueous pesticide formulation; and contacting the aqueous pesticide formulation with the pest.

[0080] In another aspect, there is provided a method for reducing or preventing Ostwald ripening of an aqueous agricultural composition, comprising adding the above-described dispersant to the aqueous agricultural composition. In a particular aspect, the aqueous agricultural composition comprises a pesticidally effective amount of a pesticide.

[0081] The dispersants may also be used in other applications, including as pigment dispersants for paint, dye or ink formulations, and as flow enhancers for cement or wallboard. Accordingly, another aspect of the present disclosure includes a coating composition comprising the dispersant, a dye or ink formulation comprising the dispersant, and a cement or wallboard comprising the dispersant. [Example]

[0082] Example 1: Dispersant synthesis procedure The following procedure was used to prepare the dispersants used in the examples below.

[0083] In a suitable reaction vessel equipped with electrical heating, overhead stirring, and an inert atmosphere, styrene-maleic anhydride copolymer resin (in powder form), tetrahydrofuran (THF), monofunctional polyalkylene glycol of formula (1), and base were combined according to the amounts shown in Table 1 below. The mixture was heated to 60°C and vigorously stirred for 12-16 hours, during which time the resin dissolved and reacted with the glycol. After the reaction was complete, glycol ether solvent was added. The base was selectively removed by centrifugation, and the THF was selectively removed under vacuum at 70°C, leaving a clear glycol ether solution of dispersant. The dispersant concentration on a solids basis was 50%. [Table 1]

[0084] Styrene maleic anhydride resin was obtained from Polyscope Polymers: XIRAN® EF-40 resin has a 4:1 styrene:maleic ratio XIRAN® EF-60 resin has a styrene:maleic acid ratio of 6:1 XIRAN® EF-80 resin has a styrene:maleic acid ratio of 8:1 MPEG polyalkylene glycol was obtained from Huntsman Petrochemical LLC: Phenyl PEG 1500: Ph-O[EO] b -O-C2H4-OH and having the general structure where b is about 31 Me EO / PO 1200 is: CH3-O-[(EO) b -(PO) c -(EO) b1 ]-C2H4-OH and having the general structure where b is about 12, c is about 3, and b1 is about 11. base 1 and bases 2 were K2CO3 and CS2CO3, respectively. The THF and glycol ether solvents were tetrahydrofuran and dipropylene glycol methyl ether (DPM), respectively.

[0085] Example: Use of dispersants in formulations Fungicide SC: In a 400 ml mixing vessel, combine water (118.3 g), propylene glycol (19.2 g), SURFONIC® L24-7 surfactant (wetting agent) (4.8 g), Dispersant 2 (7.5 g), fludioxonil fungicide (technical active ingredient) (150 g), and SAG 1572 antifoam (Momentive) (0.3 g). The slurry was transferred to a high-shear bead mill (Eiger Mini-100, EMI Engineered Mills, Grayslake, IL) and milled at 2500 rpm for 6 minutes using 1 mm Zirconox media. The product was a smooth, thin, white suspension with a median particle size of 3.06 microns.

[0086] Fungicide SC: In a 400 ml mixing vessel, combine water (118.3 g), propylene glycol (19.2 g), SURFONIC® L24-7 surfactant (wetting agent) (4.8 g), Dispersant 1 (7.5 g), Fluoxastrobin fungicide (technical active ingredient) (150 g), and SAG 1572 antifoam (Momentive) (0.3 g). The slurry was transferred to a high-shear bead mill (Eiger Mini-100, EMI Engineered Mills, Grayslake, IL) and milled at 2500 rpm for 6 minutes using 1 mm Zirconox media. The product was a smooth, thin, white suspension with a median particle size of 2.6 microns.

[0087] Herbicide SC: In a 400 ml mixing vessel, water (118.3 g), propylene glycol (19.2 g), SURFONIC® L24-7 surfactant (wetting agent) (4.8 g), Dispersant 3 (7.5 g), metribuzin herbicide (technical active ingredient) (150 g), and SAG 1572 defoamer (Momentive) (0.3 g) were combined. The slurry was transferred to a high-shear bead mill (Eiger Mini-100, EMI Engineered Mills, Grayslake, IL) and milled at 2500 rpm for 6 minutes using 1 mm Zirconox media. The product was a smooth, thin, white suspension with a median particle size of 3.78 microns.

[0088] Herbicide SC: In a 400 ml mixing vessel, water (118.3 g), propylene glycol (19.2 g), SURFONIC® L24-7 surfactant (wetting agent) (4.8 g), Dispersant 11 (7.5 g), metribuzin herbicide (technical active ingredient) (150 g), and SAG 1572 defoamer (Momentive) (0.3 g) were combined. The slurry was transferred to a high shear bead mill (Eiger Mini-100, EMI Engineered Mills, Grayslake, IL) and milled at 2500 rpm for 6 minutes using 1 mm Zirconox media. The product had a median diameter of 4.28 microns. It was a smooth thin white suspension with a particle size of 1.5 mm.

[0089] Insecticide SC: In a 400 ml mixing vessel, water (118.3 g), propylene glycol (19.2 g), SURFONIC® L24-7 surfactant (wetting agent) (4.8 g), Dispersant 2 (7.5 g), clothianidin (technical active ingredient) (150 g), and SAG 1572 antifoam (Momentive) (0.3 g) were combined. The slurry was transferred to a high-shear bead mill (Eiger Mini-100, EMI Engineered Mills, Grayslake, IL) and milled at 2500 rpm for 6 minutes using 1 mm Zirconox media. The product was a smooth, pourable white suspension with a median particle size of 3.00 microns.

[0090] While the foregoing is directed to embodiments of the present disclosure, other and further embodiments of the disclosure may be devised without departing from the basic scope thereof, the scope of which is determined by the claims which follow.

Claims

1. An aqueous agricultural composition comprising finely divided solid particles of a pest control agent present in suspended form and a dispersant for dispersing said finely divided solid particles, The dispersant comprises a styrene-maleic anhydride copolymer having a molar ratio of styrene to maleic anhydride of at least 4.0:1.0 and a copolymer of Formula (1): 2 １ 9-(3) ｐ 8 ２ｐ 9) ｚ -(EQO) ｂ -(AO) ｃ )-2 (1) (In the formula, R １ is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; and at least one of b and c is greater than 0. with a monofunctional polyalkylene glycol.

2. 2. The aqueous agricultural composition according to claim 1, wherein z is 0 and b is greater than 0.

3. 3. The aqueous agricultural composition of claim 2, wherein the styrene maleic anhydride copolymer has a molar ratio of styrene to maleic anhydride of at least 5.0:1.

0.

4. 4. The aqueous agricultural composition of claim 3, wherein the styrene maleic anhydride copolymer has a molar ratio of styrene to maleic anhydride of at least 6.0:1.

0.

5. R １ The aqueous agricultural composition according to claim 1 , wherein is a lower alkyl group.

6. R １ The aqueous agricultural composition according to claim 1 , wherein is a phenyl group.

7. 2. The aqueous agricultural composition according to claim 1, wherein z is 0, b is greater than 0, c is greater than 0, and AO is propyleneoxy.

8. The group [(EO) ｂ - (AO) ｃ 8. The aqueous agricultural composition according to claim 7, wherein: ] contains a terminal ethyleneoxy group.

9. A styrene-maleic anhydride copolymer having a molar ratio of styrene to maleic anhydride of at least 4.0:1.0 is dissolved in a non-reactive solvent, and the resulting mixture is treated with a solvent of formula (1): 2 １ 9-(3) ｐ 8 ２ｐ 9) ｚ -(EQO) ｂ -(AO) ｃ )-2 (1) (In the formula, R １ is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; and at least one of b and c is greater than 0.

2. The method of claim 1, wherein the dispersant is obtained by reacting a monofunctional polyalkylene glycol of formula (I) with a monofunctional polyalkylene glycol of formula (II).

10. 10. The method of claim 9, wherein b is greater than 0.

11. 10. The method of claim 9, wherein the reaction occurs in the presence of a base.

12. 12. The method of claim 11, wherein the base is a carbonate base.

13. 2. The aqueous agricultural composition according to claim 1, wherein the dispersant is present in an amount of 1% to 5.5% by weight, based on the total weight of the aqueous agricultural composition.

14. 10. The aqueous agricultural composition according to claim 1, wherein the pesticide is present in an amount of up to 70% by weight, based on the total weight of the aqueous agricultural composition.

15. 1. A method for killing, inhibiting or repelling pests, comprising the steps of: providing a pesticidally effective amount of finely divided solid particles of a pesticide; providing an effective amount of a dispersant; combining the pesticide with the dispersant and water to prepare an aqueous pesticide formulation comprising the finely divided solid particles of the pesticide present in suspended form and the dispersant for dispersing the finely divided solid particles; and contacting the aqueous pesticide formulation with the pest, The dispersant comprises a styrene-maleic anhydride copolymer having a molar ratio of styrene to maleic anhydride of at least 4.0:1.0 and a copolymer of Formula (1): 2 １ 9-(3) ｐ 8 ２ｐ 9) ｚ -(EQO) ｂ -(AO) ｃ )-2 (1) (In the formula, R １ is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; and at least one of b and c is greater than 0. with a monofunctional polyalkylene glycol.

16. A pigment, ink or dye formulation comprising a dispersant for dispersing particulate solids in suspended form, comprising: The dispersant comprises a styrene-maleic anhydride copolymer having a molar ratio of styrene to maleic anhydride of at least 4.0:1.0 and a copolymer of Formula (1): 2 １ 9-(3) ｐ 8 ２ｐ 9) ｚ -(EQO) ｂ -(AO) ｃ )-2 (1) (In the formula, R １ is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; and at least one of b and c is greater than 0. with a monofunctional polyalkylene glycol.

17. 1. A method for reducing or preventing Ostwald ripening in an aqueous agricultural composition, comprising adding a dispersant for dispersing finely divided solid particles to the aqueous agricultural composition, the aqueous agricultural composition comprising a pesticidally effective amount of said finely divided solid particles of a pesticide in suspended form; The dispersant comprises a styrene-maleic anhydride copolymer having a molar ratio of styrene to maleic anhydride of at least 4.0:1.0 and a copolymer of Formula (1): 2 １ 9-(3) ｐ 8 ２ｐ 9) ｚ -(EQO) ｂ -(AO) ｃ )-2 (1) (In the formula, R １ is an alkyl group or an aromatic group; p is 2 or 3; z is 0, 1, 2, or 3; EO is ethyleneoxy; AO is alkyleneoxy; b is an integer ranging from 0 to 100; c is an integer ranging from 0 to 100; and at least one of b and c is greater than 0. with a monofunctional polyalkylene glycol.

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