WO2005115144A1 - Composition pesticide - Google Patents

Composition pesticide Download PDF

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Publication number
WO2005115144A1
WO2005115144A1 PCT/US2005/018483 US2005018483W WO2005115144A1 WO 2005115144 A1 WO2005115144 A1 WO 2005115144A1 US 2005018483 W US2005018483 W US 2005018483W WO 2005115144 A1 WO2005115144 A1 WO 2005115144A1
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Prior art keywords
herbicides
fungicides
examples
phosphite
acaricides
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PCT/US2005/018483
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English (en)
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William Stringfellow
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William Stringfellow
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Publication of WO2005115144A1 publication Critical patent/WO2005115144A1/fr

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    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/26—Phosphorus; Compounds thereof

Definitions

  • This invention relates to pesticide compositions, methods for their manufacture, and methods for their use.
  • Pesticides such as herbicides
  • aqueous compositions often include an adjuvant.
  • Adjuvants include non-pesticide materials that are added to improve the mixing or stability of the pesticide.
  • These compositions also include surfactants, which are chemicals that modify the surface tension of the pesticide. Surfactants can influence the wetting and spreading of liquids, and can modify the dispersion, suspension, or precipitation of a pesticide in water.
  • a pesticidal composition comprising the combination or reaction product of (a) a phosphite; (b) a non-phosphite pesticide; and (c) water.
  • An aqueous pesticide composition includes a mixture or reaction product of (a) a phosphite compound, (b) a non-phosphite pesticide, and (c) water.
  • the pesticide compositions may also include additional ingredients including those conventionally employed in the art.
  • Useful phosphite compounds include salts of phosphorous acid (i.e.,
  • Suitable phosphorous acid salts include inorganic or mineral salts and organic salts.
  • Useful inorganic salts include alkali or alkaline earth metal salts such as those including lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, and barium salts of phosphoric acid.
  • Heavier metal salts may also be used such as those including copper, iron, nickel, cobalt, manganese, zinc, and aluminum phosphorous acid salts.
  • the phosphorous acid salts include monopotassium phosphite (KH2PO3), dipotassium phosphite
  • K2HPO3 tripotassium phosphite
  • K3PO3 tripotassium phosphite
  • Useful organic phosphite salts include nitrogen-containing compounds that can accept a proton from phosphorous acid. These compounds include primary, secondary or tertiary, optionally substituted aliphatic, aromatic, alicyclic or heterocyclic amines or of other nitrogen-containing derivatives, including for example imidazoles, cyclohexylamines, anilines, and morpholines.
  • the aromatic and heterocyclic nitrogen containing compounds may be substituted, preferably with up to three alkyl groups, each containing from 1-4 carbon atoms.
  • inorganic or organic salts of substituted phosphorous acid compounds such as monoester phosphorous acids can be used.
  • Useful monoester salts of phosphorous acid include calcium ethyl phosphite, sodium ethyl phosphite, aluminum ethyl phosphite, magnesium isopropyl phosphite, calcium isopropyl phosphite, aluminum isopropyl phosphite, magnesium ethyl phosphite, magnesium isobutyl phosphite, magnesium sec-butyl phosphite, calcium isobutyl phosphite, aluminum N-butyl phosphite, aluminum sec-butyl phosphite, and aluminum isobutyl phosphite.
  • the phosphite compounds can be prepared by neutralization of or by double replacement reactions of phosphorous acid.
  • monopotassium phosphite can be prepared by reacting one equivalent of potassium hydroxide with one equivalent of phosphorous acid within an aqueous solution.
  • neutral potassium phosphite i.e. dipotassium phosphite
  • reacting two equivalents of potassium hydroxide with one equivalent of phosphorous acid within an aqueous solution can be prepared by reacting two equivalents of potassium hydroxide with one equivalent of phosphorous acid within an aqueous solution.
  • Aqueous solutions of potassium phosphite are commercially available including those products available under the tradename AgrifosTM (AgriChem; Australia); NutriPhiteTM, (BiAgro Western; California), MagallenTM (NuFarm); Phos ProTM (J.H.
  • Useful non-phosphite pesticides include herbicides, insecticides, fungicides, miticides, nematicides, and plant growth regulators.
  • Useful herbicides include water-soluble, oil-soluble, or solvent-based herbicides. These include compounds that have herbicidal activity against woody, brush or arborescent plants.
  • Types of herbicides include amide herbicides, anilide herbicides, arylalanine herbicides, chloroacetanilide herbicides, sulfonanilide herbicides, antibiotic herbicides, benzoic acid herbicides, pyrimidinyloxybenzoic acid herbicides, pyrimidinylthiobenzoic acid herbicides, phthalic acid herbicides, picolinic acid herbicides, quinolinecarboxylic acid herbicides, arsenical herbicides, benzoylcyclohexanedione herbicides, benzofuranyl alkylsulfonate herbicides, carbamate herbicides, carbanilate herbicides, cyclohexene oxime herbicides, cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides, nitrophenyl ether herbicides,
  • amide herbicides include allidochlor, beflubutamid, benzadox, benzipram, bromobutide, cafenstrole, CDEA, chlorthiamid, cyprazole, dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamid, isoxaben, napropamide, naptalam, penoxsulam, pethoxamid, propyzamide, quinonamid, and tebutam.
  • Examples of anilide herbicides include chloranocryl, cisanilide, clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinafen, and propanil.
  • Examples of arylalanine herbicides include benzoylprop, flamprop, and flamprop-M.
  • chloroacetanilide herbicides include acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor, and xylachlor.
  • Examples of sulfonanilide herbicides include benzofluor, cloransulam, diclosulam, florasulam, flumetsulam, metosulam, perfluidone, and profluazol.
  • Examples of antibiotic herbicides include bilanafos.
  • Examples of benzoic acid herbicides include chloramben, dicamba, and
  • pyrimidinyloxybenzoic acid herbicides include bispyribac and pyriminobac.
  • pyrimidinylthiobenzoic acid herbicides include pyrithiobac.
  • Examples of phthalic acid herbicides include chlorthal.
  • Examples of picolinic acid herbicides include aminopyralid, clopyralid, and picloram.
  • Examples of quinolinecarboxylic acid herbicides include quinclorac and quinmerac.
  • Examples of arsenical herbicides include cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite, and sodium arsenite.
  • Examples of benzoylcyclohexanedione herbicides include mesotrione and sulcotrione.
  • Examples of benzofuranyl alkylsulfonate herbicides include benfuresate, and ethofumesate.
  • Examples of carbamate herbicides include asulam, carboxazole, chlorprocarb, dichlormate, fenasulam, karbutilate, and terbucarb.
  • Examples of carbanilate herbicides include barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham-ethyl, propham, and swep.
  • Examples of cyclohexene oxime herbicides include alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim.
  • Examples of cyclopropylisoxazole herbicides include isoxachlortole, and isoxaflutole.
  • Examples of dicarboximide herbicides include benzfendizone, cinidon- ethyl, flumezin, flumiclorac, flumioxazin, and flumipropyn.
  • Examples of dinitroaniline herbicides include benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, and trifluraiin.
  • dinitrophenol herbicides examples include dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen, and medinoterb.
  • Examples of diphenyl ether herbicides include ethoxyfen.
  • Examples of nitrophenyl ether herbicides include acifluorfen, aclonifen, bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen, and oxyfluorfen.
  • Examples of dithiocarbamate herbicides include dazomet, and metam.
  • halogenated aliphatic herbicides include alorac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA, and TCA.
  • imidazolinone herbicides include imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, and imazethapyr.
  • nitrile herbicides include bromobonil, bromoxynil, chloroxynil, dichlobenil, iodobonil, ioxynil, and pyraclonil.
  • inorganic herbicides include ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, potassium cyanate, sodium azide, sodium chlorate, and sulfuric acid.
  • organophosphorus herbicides include amiprofos-methyl, anilofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glyphosate, and piperophos.
  • phenoxy herbicides include bromofenoxim, clomeprop, 2,4- DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol, and trifopsime.
  • phenoxyacetic herbicides examples include 4-CPA, 2,4 dichlorophenoxyacetic acid (2,4-D), 3,4-DA, MCPA, MCPA-thioethyl, and 2,4,5-T.
  • phenoxybutyric herbicides examples include 4-CPB, 2,4-DB, 3,4-DB, MCPB, and 2,4,5-TB.
  • phenoxypropionic herbicides include cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, and mecoprop-P.
  • Examples of aryloxyphenoxypropionic herbicides include chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, and quizalofop-P, and trifop.
  • Examples of phenylenediamine herbicides include dinitramine, and prodiamine.
  • Examples of pyrazolyloxyacetophenone herbicides include benzofenap, and pyrazoxyfen.
  • Examples of pyrazolylphenyl herbicides include fluazolate, and pyraflufen.
  • Examples of pyridazine herbicides include redazine, pyridafol, and pyridate.
  • Examples of pyridazinone herbicides include brompyrazon, chloridazon, dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazon, and pydanon.
  • pyridine herbicides include aminopyralid, cliodinate, clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram, picolinafen, pyriclor, thiazopyr, and triclopyr.
  • pyrimidinediamine herbicides include iprymidam, and tioclorim.
  • Examples of quaternary ammonium herbicides include cyperquat, diethamquat, difenzoquat, diquat, morfamquat, and paraquat.
  • Examples of thiocarbamate herbicides include butylate, cycloate, di- allate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, sulfallate, thiobencarb, tiocarbazil, tri-allate, and vernolate.
  • Examples of thiocarbonate herbicides include dimexano, EXD, and proxan. Examples of thiourea herbicides include methiuron. Examples of triazine herbicides include dipropetryn, triaziflam, and trihydroxytriazine.
  • Examples of chlorotriazine herbicides include atrazine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine, and trietazine.
  • Examples of methoxytriazine herbicides include atraton, methometon, prometon, secbumeton, simeton, and terbumeton.
  • Examples of methylthiotriazine herbicides include ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn, simetryn, and terbutryn.
  • Examples of triazinone herbicides include ametridione, amibuzin, hexazinone, isomethiozin, metamitron, and metribuzin.
  • Examples of triazole herbicides include amitrole, cafenstrole, and epronaz, flupoxam.
  • Examples of triazolone herbicides include amicarbazone, carfentrazone, flucarbazone, propoxycarbazone, and sulfentrazone.
  • Examples of triazolopyrimidine herbicides include cloransulam, diclosulam, florasulam, flumetsulam, metosulam, and penoxsulam.
  • uracil herbicides include butafenacil, bromacil, flupropacil, isocil, lenacil, and terbacil.
  • urea herbicides include benzthiazuron, cumyluron, cycluron, dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthiazuron, monisouron, and noruron.
  • phenylurea herbicides include anisuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron, methiuron, methyldymron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron, and thidiazuron.
  • Examples of pyrimidinylsulfonylurea herbicides include amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, mesosulfuron, nicosulfuron, oxasulfuron, primisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, and trifloxysulfuron.
  • Examples of triazinylsulfonylurea herbicides include chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, and tritosulfuron.
  • Examples of thiadiazolylurea herbicides include buthiuron, ethidimuron, tebuthiuron, thiazafluron, and thidiazuron.
  • Examples of other unclassified herbicides include acrolein, allyl alcohol, azafenidin, benazolin, bentazone, benzobicyclon, buthidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin, clomazone, CPMF, cresol, ortho-dichlorobenzene, dimepiperate, endothal, fluoromidine, fluridone, flurochloridone, flurtamone, fluthiacet, indanofan, methazole, methyl isothiocyanate, nipyraclofen, OCH, oxadiargyl, oxadiazon, oxaziclomefone, pentachlorophenol, pentoxazone, phenylmercury acetate, pinoxaden, prosulfalin, pyrazolynate, pyribenzoxim,
  • glyphosate Water-soluble salts of N-phosphonomethylglycine (glyphosate), analogs and homologs of glyphosate are preferred.
  • glyphosate encompasses glyphosate and herbicidal derivatives thereof, such as salts and other water-soluble compounds that are converted to glyphosate in plant tissues or that otherwise provide glyphosate ion.
  • Glyphosate salts include alkali metal salts, such as sodium and potassium salts; ammonium salt; C ⁇ s alkylammonium salts, such as dimethylammonium and isopropylammonium salts; Cj.jg alkanolammonium salts, such as monoethanolamine salts; C j . ⁇ alkylsulfonium salts, such as trimethylsulfonium salts; and mixtures thereof.
  • ammonium, alkylammonium, alkanolammonium, alkylsulfonium and alkali metal salts of glyphosate are highly water-soluble, thereby allowing for highly concentrated solutions that may be diluted at the site of use.
  • herbicidal compositions include ROUNDUP®,
  • ROUNDUP® ULTRA and ACCORD®, which contain the monoisopropylammonium (IPA) salt of N-phosphonomethylglycine (Monsanto); ROUNDUP® DRY and RIVAL®, which contain the ammonium salt of N-phosphonomethylglycine (Monsanto); ROUNDUP® GEOFORCE, which contains the sodium salt of N- phosphonomethylglycine (Monsanto); and TOUCHDOWN®, which contains the trimethylsulfonium salt of N-phosphonomethylglycine (Zeneca Limited).
  • IPA monoisopropylammonium
  • ROUNDUP® DRY and RIVAL® which contain the ammonium salt of N-phosphonomethylglycine
  • ROUNDUP® GEOFORCE which contains the sodium salt of N- phosphonomethylglycine (Monsanto)
  • TOUCHDOWN® which contains the trimethylsulfonium salt of N-phosphonomethylglycine (Zeneca
  • Useful systemic insecticidal compounds include nitroguanidine, acetamprid, imidaclorprid, spinosad, abamectin, pyriproxfen, pymetrozine, clofentezine, hexythiazox, diflubenzuron, chlorfenapyr, novaluron, diflubenzon, azadicrchtin, and fenpyroximate.
  • Useful fungicides include aliphatic nitrogen fungicides, amide fungicides, acylamino acid fungicides, furamide fungicides, phenylsulfamide fungicides, valinamide fungicides, anilide fungicides, benzanilide fungicides, furanilide fungicides, sulfonanilide fungicides, antibiotic fungicides, strobilurin fungicides, aromatic fungicides, benzimidazole fungicides, benzimidazole precursor fungicides, benzothiazole fungicides, bridged diphenyl fungicides, carbamate fungicides, benzimidazolylcarbamate fungicides, carbanilate fungicides, conazole fungicides such as imidazole and triazole conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithi
  • aliphatic nitrogen fungicides include butylamine, cymoxanil, dodicin, dodine, guazatine, and iminoctadine.
  • Amide fungicides include carpropamid, chloraniformethan, cyazofamid, cyflufenamid, diclocymet, ethaboxam, fenoxanil, flumetover, furametpyr, prochloraz, quinazamid, silthiofam, and triforine.
  • acylamino acid fungicides include benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, and pefurazoate.
  • Benzamide fungicides benzohydroxamic acid, tioxymid, trichlamide, zarilamid, zoxamide.
  • furamide fungicides include cyclafuramid, furmecyclox.
  • phenylsulfamide fungicides include dichlofluanid, tolylfluanid.
  • Valinamide fungicides include benthiavalicarb, iprovalicarb.
  • anilide fungicides include benalaxyl, benalaxyl-M boscalid, carboxin, fenhexamid, metalaxyl, metalaxyl-M, metsulfovax, ofurace, oxadixyl, oxycarboxin, pyracarbolid, thifluzamide, and tiadinil.
  • benzanilide fungicides include benodanil, flutolanil, mebenil, mepronil, salicylanilide, and tecloftalam.
  • Furanilide fungicides include fenfuram, furalaxyl, furcarbanil, and methfuroxam.
  • sulfonanalide fungicides include flusulfamide.
  • antibotic fungicides include aureofungin, blasticidin-S, cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxins, polyoxorim, streptomycin, and validamycin.
  • Strobilurin fungicides include azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin.
  • aromatic fungicides include biphenyl, chlorodinitronaphthalene, chloroneb, chlorothalonil, cresol, dicloran, hexachlorobenzene, pentachlorophenol, quintozene, sodium pentachlorophenoxide, and tecnazene.
  • Benzimidazole fungicides include benomyl, carbendazim, chlorfenazole, cypendazole, debacarb, fuberidazole, mecarbinzid, rabenzazole, and thiabendazole.
  • Examples of benzimidazole precursor fungicides include furophanate, thiophanate, and thiophanate-methyl.
  • benzothiazole fungicides include bentaluron, chlobenthiazone, and TCMTB.
  • bridged diphenyl fungicides include bithionol, dichlorophen, and diphenylamine.
  • carbamate fungicides include benthiavalicarb, furophanate, iprovalicarb, propamocarb, thiophanate, and thiophanate-methyl.
  • Benzimidazolylcarbamate fungicides include benomyl, carbendazim, cypendazole, debacarb, and mecarbinzid.
  • carbanilate fungicides include diethofencarb.
  • conazole imidazole fungicides include climbazole, clotrimazole, imazalil, oxpoconazole, prochloraz, and triflumizole.
  • conazole triazole fungicides include azaconazole, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, quinconazole, simeconazole, tebuconazole, tetraconazole,
  • Copper fungicides include Bordeaux mixture, Burgundy mixture,
  • dicarboximide fungicides include famoxadone, fluoroimide.
  • dichlorophenyl dicarboximide fungicides include chlozolinate, dichlozoline, iprodione, isovaledione, myclozolin, procymidone, and vinclozolin.
  • phthalimide fungicides include captafol, captan, ditalimfos, folpet, and thiochlorfenphim.
  • dinitrophenol fungicides include binapacryl, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfon, dinoterbon, and DNOC.
  • dithiocarbamate fungicides include azithiram, carbamorph, cufraneb, cuprobam, disulfiram, ferbam, metam, nabam, tecoram, thiram, and ziram.
  • cyclic dithiocarbamate fungicides include dazomet, etem, and milneb.
  • Polymeric dithiocarbamate fungicides include mancopper, mancozeb, maneb, metiram, polycarbamate, propineb, and zineb.
  • imidazole fungicides include cyazofamid, fenamidone, fenapani, glyodin, iprodione, isovaledione, pefurazoate, triazoxide.
  • inorganic fungicides include potassium azide, potassium thiocyanat, sodium azide, and sulfur.
  • inorganic mercury fungicides include mercuric chloride, mercuric oxide, and mercurous chloride.
  • organomercury fungicides include (3-ethoxypropyl)mercury bromide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury 2,3-dihydroxypropyl mercaptide, ethylmercury phosphate, N- (ethylmercury) -p-toluenesulphonanilide, hydrargaphen, 2-methoxyethylmercury chloride, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide, 8- phenylmercurioxyquinoline, phenylmercuriurea, phenylmercury acetate, phenylmercury
  • morpholine fungicides include aldimorph, benzamorf, carbamorph, dimethomorph, dodemorph, fenpropimorph, flumorph, and tridemorph.
  • organophosphorus fungicides include ampropylfos, ditalimfos, edifenphos, fosetyl, hexylthiofos, iprobenfos, phosdiphen, pyrazophos, tolclofos-methyl, and triamiphos.
  • organotin fungicides include decaf entin, fentin, and tributyltin oxide.
  • oxathiin fungicides include carboxin, and oxycarboxin.
  • Oxazole fungicides include chlozolinate, dichlozoline, drazoxolon, famoxadone, hymexazol, metazoxolon, myclozolin, oxadixyl, vinclozolin.
  • polysulfide fungicides include barium polysulfide, calcium polysulfide, potassium polysulfide, and sodium polysulfide.
  • Specific examples of pyridine fungicides include boscalid, buthiobate, dipyrithione, fluazinam, pyridinitril, pyrifenox, pyroxychlor, and pyroxyfur.
  • Pyrimidine fungicides include bupirimate, cyprodinil, diflumetorim, dimethirimol, ethirimol, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, and triarimol.
  • Examples of pyrrole fungicides include fenpiclonil, fludioxonil, and fluoroimide.
  • quinoline fungicides include ethoxyquin, halacrinate, 8-hydroxyquinoline sulfate, quinacetol, and quinoxyfen.
  • quinone fungicides include benquinox, chloranil, dichlone, and dithianon.
  • Quinoxaline fungicides include chinomethionat, chlorquinox, and thioquinox.
  • thiazole fungicides include ethaboxam, etridiazole, metsulfovax, octhilinone, thiabendazole thiadifluor, and thifluzamide.
  • Thiocarbamate fungicides include methasulfocarb and prothiocarb.
  • Examples of thiophene fungicides include ethaboxam, and silthiofam.
  • Specific examples of triazine fungicides include anilazine.
  • Triazole fungicides include bitertanol, fluotrimazole, and triazbutil. Examples of urea fungicides include bentaluron, pencycuron, and quinazamid.
  • fungicides include acibenzolar, acypetacs, allyl alcohol, benzalkonium chloride, benzamacril, bethoxazin, carvone, chloropicrin, DBCP, dehydroacetic acid, diclomezine, diethyl pyrocarbonate, fenaminosulf, fenitropan, fenpropidin, formaldehyde, furfural, hexachlorobutadiene, iodomethane, isoprothiolane, methyl bromide, methyl isothiocyanate, metrafenone, nitrostyrene, nitrothal-isopropyl, OCH, 2- phenylphenol, phthalide, piperalin, probenazole, proquinazid, pyroquilon, sodium orthophenylphenoxide, spiroxamine, sultropen, thicyofen, tricyclazole, and zinc
  • Suitable acaricides include antibiotic acaricides, macrocyclic lactone acaricides, avermectin acaricides, milbemycin acaricides, bridged diphenyl acaricides, carbamate acaricides, oxime carbamate acaricides, dinitrophenol acaricides, formamidine acaricides, organochlorine acaricides, organophosphorus acaricides such as organophosphate acaricides organothiophosphate acaricides, phosphonate acaricides, trichlorfon phosphoramidothioate acaricides, and phosphorodiamide acaricides, organotin acaricides, phenylsulfamide acaricides, phthalimide acaricides, pyrazole acaricides, pyrethroid acaricides such as pyrethroid ester acaricides
  • Antibiotic acaricides include nikkomycins and thuringiensin.
  • Macrocyclic lactone acaricides include tetranactin.
  • Avermectin acaricides include abamectin, doramectin, eprinomectin, ivermectin, and selamectin.
  • Milbemycin acaricides include milbemectin, milbemycin oxime, and moxidectin.
  • Bridged diphenyl acaricides include azobenzene, benzoximate, benzyl benzoate, bromopropylate, chlorbenside, chlorfenethol, chlorfenson, chlorfensulphide, chlorobenzilate, chloropropylate, DDT, dicofol, diphenyl sulfone, dofenapyn, fenson, fentrifanil, fluorbenside, proclonol, tetradifon, and tetrasul.
  • Carbamate acaricides include benomyl, carbanolate, carbaryl, carbofuran, methiocarb, metolcarb, promacyl, and propoxur.
  • Oxime carbamate acaricides include aldicarb, butocarboxim, oxamyl, thiocarboxime, and thiofanox,
  • Dinitrophenol acaricides include binapacryl, dinex, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfon, dinoterbon, and DNOC.
  • Formamidine acaricides include amitraz, chlordimeform, chloromebuform, formetanate, formparanate, mite growth regulators, clofentezine, dofenapyn, fluazuron, flubenzimine, flucycloxuron, flufenoxuron, and hexythiazox.
  • Organochlorine acaricides include bromocyclen, camphechlor, DDT, dienochlor, endosulfan, and lindane.
  • Organophosphate acaricides include chlorfenvinphos, crotoxyphos, dichlorvos, heptenophos, mevinphos, monocrotophos, naled, schradan, TEPP, and tetrachlorvinphos.
  • Organothiophosphate acaricides include amidithion, amiton, azinphos- ethyl, azinphos-methyl, azothoate, benoxafos, bromophos, bromophos-ethyl, carbophenothion, chlorpyrifos, chlorthiophos, coumaphos, cyanthoate, demeton, demeton-O, demeton-S, demeton-methyl, demeton-O-methyl, demeton- S-methyl, demeton- S-methylsulphon, dialifos, diazinon, dimethoate, dioxathion, disulfoton, endothion, ethion, ethoate-methyl, formothion, malathion, mecarbam, methacrifos, omethoate, oxydeprofos, oxydisulfoton, parathion, phenkapton, phor
  • Phosphonate acaricides include trichlorfon.
  • Phosphoramidothioate acaricides include isocarbophos, methamidophos, and propetamphos.
  • Phosphorodiamide acaricides include dimefox, and mipafox.
  • Organotin acaricides include azocyclotin, cyhexatin, and fenbutatin oxide.
  • Phenylsulfamide acaricides include dichlofluanid.
  • Phthalimide acaricides include dialifos, and phosmet.
  • Pyrazole acaricides include acetoprole, fipronil, tebufenpyrad, and vaniliprole.
  • Pyrethroid ester acaricides include acrinathrin, bifenthrin, cyhalothrin, cypermethrin, alpha-cypermethrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate, and permethrin.
  • Pyrethroid ether acaricides include halfenprox.
  • Pyrimidinamine acaricides include pyrimidifen.
  • Pyrrole acaricides include chlorfenapyr.
  • Quinoxaline acaricides include chinomethionat, and thioquinox.
  • Sulfite ester acaricides include propargite.
  • Tetronic acid acaricides include spirodiclofen.
  • Thiocarbamate acaricides include fenothiocarb.
  • Thiourea acaricides include chloromethiuron and diafenthiuron.
  • Unclassified acaricides include acequinocyl, amidoflumet, arsenous oxide, bifenazate, closantel, crotamiton, disulfiram, etoxazole, fenazaflor, fenazaquin, fenpyroximate, fluacrypyrim, fluenetil, mesulfen, MNAF, nifluridide, pyridaben, sulf ⁇ ram, sulfluramid, sulfur, and triarathene.
  • Useful nematicides include antibiotic nematicides, carbamate nematicides, oxime carbamate nematicides, organophosphorus nematicides such as organophosphate nematicides and organothiophosphate nematicides, and other unclassified nematicides.
  • Antibiotic nematicides include abamectin.
  • Carbamate nematicides include benomyl, carbofuran, carbosulfan, and cloethocarb.
  • Oxime carbamate nematicides include alanycarb, aldicarb, aldoxycarb, and oxamyl.
  • Organophosphate nematicides include diamidafos, fenamiphos, fosthietan, and phosphamidon.
  • Organothiophosphate nematicides include cadusafos, chlorpyrifos, dichlofenthion, dimethoate, ethoprophos, fensulfothion, fosthiazate, heterophos, isamidofos, isazofos, mecarphon, phorate, phosphocarb, terbufos, thionazin, and triazophos.
  • Unclassified nematicides include acetoprole, benclothiaz, chloropicrin, dazomet, DBCP, DCIP, 1,2-dichloropropane, 1,3-dichloropropene, furfural, iodomethane, metam, methyl bromide, methyl isothiocyanate, and xylenols.
  • Plant growth regulators include antiauxins, auxins, cytokinins, defoliants, ethylene inhibitors, ethylene releasers, gibberellins, growth inhibitors, growth retardants, growth stimulators, and unclassified plant growth regulators.
  • Antiauxins include clofibric acid and 2,3,5-tri-iodobenzoic acid.
  • Auxins include 4-CPA, 2,4-D, 2,4-DB, 2,4-DEP, dichlorprop, fenoprop, IAA, IBA, naphthaleneacetamide, ⁇ -naphthaleneacetic acid, 1-naphthol, naphthoxyacetic acid, potassium naphthenate, sodium naphthenate, and 2,4, 5-T.
  • Cytokinins include 2iP, benzyladenine, kinetin, and zeatin.
  • Defoliants include calcium cyanamide, dimethipin, endothal, ethephon, metoxuron, pentachlorophenol, thidiazuron, and tribufos.
  • Ethylene inhibitors include aviglycine, and 1-methylcyclopropene.
  • Ethylene releasers include ACC, et reviewingl, ethephon, and glyoxime.
  • Gibberellins include gibberellins, and gibberellic acid.
  • Growth inhibitors include abscisic acid, ancymidol, butralin, carbaryl, chlorphonium, chlorpropham, dikegulac, flumetralin, fluoridamid, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, piproctanyl, prohydrojasmon, propham, 2,3,5-tri-iodobenzoic acid, and morphactins such as chlorfluren, chlorflurenol, dichlorflurenol, and flurenol.
  • Growth retardants include chlormequat, daminozide, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, and uniconazole.
  • Growth stimulators include brassinolide, forchlorfenuron, and hymexazol.
  • Unclassified plant growth regulators include benzofluor, buminafos, carvone, ciobutide, clofencet, cloxyfonac, cyclanilide, cycloheximide, epocholeone, ethychlozate, ethylene, fenridazon, heptopargil, holosulf, inabenfide, karetazan, lead arsenate, methasulfocarb, prohexadione, pydanon, sintofen, triapenthenol, and trinexapac.
  • compositions of this invention may also optionally include a phosphate compound.
  • Useful phosphate compounds include salts of phosphoric acid (i.e., H3PO4).
  • Suitable phosphoric acid salts include inorganic or mineral salts and organic salts.
  • Useful inorganic salts include alkali or alkaline earth metal salts such as those including lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, and barium salts of phosphoric acid. Heavier metal salts may also be used such as those including copper, iron, nickel, cobalt, manganese, zinc, and aluminum phosphorous acid salts.
  • These phosphoric acid salts are disclosed in U.S. Patent Nos. 5,736,164, 5,800,837, 5,925,383, 5,997,910, 6,338,860, 6,509,041, and 6,139,879, which are incorporated herein by reference.
  • the phosphoric acid salts include monopotassium phosphate (KH2PO4), dipotassium phosphate (K2HPO4), tripotassium phosphate
  • K3PO4 mixtures of mono and di potassium phosphate, or mixtures of mono, di, and tri potassium phosphate.
  • compositions of this invention may also optionally include a solvent.
  • solvents useful as solvents provide a number of advantageous properties and are therefore generically described in different ways by those skilled in the art.
  • these solvents may also be referred to as coupling agents, emulsifiers, humectants, and pour point depressants.
  • Useful solvents include alcohols, glycols, glycol esters, and the like.
  • alcohols examples include methanol, ethanol, n-propanol, isopropanol, n- butanol, isobutanol, amyl alcohol, methyl amyl alcohol, cyclohexanol, 2- ethylhexanol, furfuryl alcohol, and d-limonene.
  • glycols and glycol esters include monoethylene glycol, diethylene glycol, propylene glycol or the methyl, ethyl, n-propyl, n-butyl or t-butyl ethers thereof, dipropylene glycol or the methyl, ethyl, n-propyl, n-butyl or t-butyl ethers thereof, tripropylene glycol, or the methyl, ethyl, n-propyl, n-butyl or t-butyl ethers thereof, 1,3-butanediol, 1,4- butanediol, 2-methyl-l,3-propanediol, 2,2-dimethyl-l,3-propanediol, 2-methyl-l,3- pentanediol, 2-methyl-2,4-pentanediol, 2-methyl-l,3-propanediol and 1,4- butaned
  • compositions of this invention may also optionally include an adjuvant.
  • adjuvants include surface-active agents (surfactants), stickers, spreaders (extenders), plant penetrants, compatibility agents, pH regulators, drift retardants, defoaming agents, and thickeners.
  • adjuvants include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, silicone-based surfactants, diols, N- alkyl pyrrolidones, alkyl polysaccharides, alkenyl succinic anhydride condensates, methylated vegetable oils, mineral oils, phospholipids, liquid crystals, and urea clathrates.
  • Nonionic surfactants include alkylphenol ethoxylates, long-chain alkanol ethoxylates, long-chain alkylamine ethoxylates, sorbitan esters and their ethoxylates, castor oil ethoxylates.
  • Stickers include vegetable gels, resins, mineral oils, vegetable oils, waxes, or latex polymers.
  • Spreaders include blends of surfactants, primarily nonionic.
  • Drift retardants are typically long chain polymers or gums that increase the viscosity of the pesticide composition. Examples include polyacrylamides, polysaccharides (hydroxypropyl guar), and polyethylene oxide.
  • Surface-active agents include those compounds defined by ASTM El 519-99, which are materials that when added to a liquid modify the properties of the medium at the surface or interface. These agents are generally known and described in U.S. Patent Application No. 20020107149, which is incorporated herein by reference.
  • Useful surface active agents include Methylated C6-C19 fatty acids, Methylated Tall oil fatty acids, Methylated Oleic acid, Methylated Linoleic acid, Methylated Linolenic acid, Methylated Stearic acid, Methylated Palmitic acid, Ethylated C6-C19 fatty acids, Ethylated Tall oil fatty acids, Ethylated Oleic acid, Ethylated Linoleic acid, Ethylated Linolenic acid, Ethylated Stearic acid, Ethylated Palmitic acid, Butylated C6-C19 fatty acids, Butylated Tall oil fatty acids, Butylated Oleic acid, Butylated Linoleic acid Butylated Linolenic acid, Butylated Stearic acid, Butylated Palmitic acid, Methylated soybean oil, Ethylated soybean oil, Butylated soybean oil, buty
  • adjuvants include KeniticTM, DynamicTM, InduceTM, LI 700TM, AgriwetTM, BallastTM, Indicate 5TM, pHyloTM, AdseeTM, ArmixTM, SpontoTM, B.S. 500TM, Nutra ZorbTM, Aero DynamicTM, Agri DexTM, OptimaTM, Penetrator PlusTM, QuestTM, RenegadeTM, Super spreadTM, Tri FolTM, Break thruTM, HyperactiveTM, and Silwet.TM
  • the pH of the aqueous compositions of this invention is maintained at a pH of about 2 to about 9, more preferably from about 5 to about 7, and even more preferably from about 5.5 to about 6.5.
  • the pH is maintained to prevent the phosphite compounds from being oxidized into phosphate compounds.
  • the amount of phosphite within the compositions of this invention may vary. As those skilled in the art will appreciate, the aqueous solutions of this invention can be formulated in concentrated form, which is useful for transportation and storage, and then diluted prior to use in the field. But, those skilled in the art that make or use the compositions of this invention will be able to readily formulate useful compositions based upon the usage rates for phosphite, which are provided hereinbelow.
  • compositions of this invention that are useful for applying to plants (as opposed to concentrate forms that can be prepared for shipping and transportation) can include from about 1 to about 1000 grams of phosphite per liter of solution, alternatively from about 5 to about 500 grams of phosphite per liter of solution, alternatively from about 8 to about 300 grams of phosphite per liter of solution, and alternatively from about 10 to about 200 grams of phosphite per liter of solution.
  • certain compositions of this invention may include from about 0.5% to about 100% by weight phosphite, in other embodiments from about 5% to about 50% by weight phosphite, and in other embodiments from about 10% to about 30% by weight phosphite.
  • the amount of pesticide within the compositions of this invention may likewise vary. This variance may not only result from the aqueous nature of the inventive compositions, but also from the large variance in usage or application rates or concentrations that are typically or conventionally employed for any given pesticide.
  • the amount of pesticide within the solutions of this invention is consistent with those amounts or concentrations that are conventional for the pesticide in question or employed. In other embodiments, because practice of this invention increases the efficacy or efficiency of the pesticides, the amount of pesticide within the solutions of this invention may be less than 95%, in other embodiments less than 90%, in other embodiments less than 85%, in other embodiments less than 80%, and in other embodiments less than 75% of that concentration that is conventional for the particular pesticide in employed and yet still provides sufficient potency to treat the acreage that would otherwise be treated by 100% of the conventional usage for the particular pesticide. [119] In other embodiments, the amount of pesticide within the composition can be described with reference to the phosphite compound.
  • the weight ratio of phosphite to glyphosate may be about 1:0.5 to about 1:500, in other embodiments from about 1:1 to about 1:100, in other embodiments from about 1:5 to about 1:50, in other embodiments from about 1:10 to about 1:35, and in other embodiments 1:15 to about 1:25.
  • the weight ratio of phosphite to imidazolinone can be about 50:1 to about 1:50, in other embodiments from about 40:1 to about 1:20, in other embodiments from about 30:1 to about 1:1, in other embodiments from about 20:1 to about 3:1, and in other embodiments 15:1 to about 5:1.
  • the weight ratio of phosphite to triazinylsulfonylurea may be about 100:1 to about 1:20, in other embodiments from about 60:1 to about 10:1, in other embodiments from about 50:1 to about 1:1, in other embodiments from about 40:1 to about 10:1, and in other embodiments 30:1 to about 15:1.
  • the pesticidal compositions of this invention may include from about 0.0001 to about 1.0 parts by weight, in other embodiments from about 0.001 to about 0.05 parts by weight, in other embodiments from about 0.005 to about 0.1 parts by weight, and in other embodiments from about 0.01 to about 0.05 parts by weight solvent per part of phosphite (pesticide).
  • the pesticidal compositions of this invention may include from about 0.0001 to about 3.0 parts by weight, in other embodiments from about 0.001 to about 1.0 parts by weight, in other embodiments from about 0.005 to about 0.1 parts by weight, and in other embodiments from about 0.01 to about 0.05 parts by weight adjuvant per part of phosphate.
  • the pesticidal compositions of this invention may include from about 0.0001 to about 3.0 parts by weight, in other embodiments from about 0.001 to about 1.0 parts by weight, in other embodiments from about 0.005 to about 0.1 parts by weight, and in other embodiments from about 0.01 to about 0.05 parts by weight surfactant per part of phosphite.
  • the compositions of this invention may include from about 0.0001 to about 2.0 parts by weight, in other embodiments from about 0.001 to about 1.0 parts by weight, in other embodiments from about 0.005 to about 0.1 parts by weight, and in other embodiments from about 0.01 to about 0.05 parts by weight phosphate per part of phosphite.
  • the pesticidal compositions of this invention may be manufactured and shipped as a concentrated aqueous composition and diluted (e.g. add water) prior to application.
  • the concentrated solutions may include from about 100 to about 0.0002 % by weight solids, in other embodiments from about 80 to about 1.0 % by weight solids, in other embodiments from about 60 to about 20 % by weight solids, and in other embodiments from about 50 to about 30 % by weight solids.
  • useful compositions may advantageously include from about 50 to about 0.0001% by weight solids, in other embodiments from about 40 to about 0.1 % by weight solids, in other embodiments from about 30 to about 0.1% by weight solids, in other embodiments from about 20 to about 1 %. by weight solids, and in other embodiments from about 10 to about 5 % by weight solids.
  • One of the advantageous features of this invention is the ability to prepare compositions by combining the pesticide and phosphite, optionally together with the other optional ingredients, at the location of manufacture, and then ship to the location of use in a concentrated form.
  • separate concentrated compositions of the phosphite and concentrated solutions of the pesticide can be shipped to the location of use, combined at that location, and diluted prior to use.
  • compositions of this invention can dilute the compositions of this invention to achieve a coverage concentration or rate that applies about 1 to about 1000 grams per acre, preferably about 50 to about 600 grams per acre, in other embodiments about 100 to about 500 grams per acre, in other embodiments about 150 to about 450 grams per acre, and in other embodiments about 200 to about 400 grams per acre of glyphosate.
  • imidazolinone is the herbicide employed
  • compositions of this invention can be applied to a plant by employing a variety of techniques.
  • compositions of this invention can be applied to any living or dead plant tissue by a number of methods including, but not limited to, a spray boom, a hand sprayer, low volume applicators, high and low volume field mounted equipment, aerial sprayers, controlled droplet applicators, CDA equipment, and combinations thereof.
  • a spray boom a hand sprayer
  • low volume applicators high and low volume field mounted equipment
  • aerial sprayers controlled droplet applicators
  • CDA equipment controlled droplet applicators
  • combinations thereof a number of methods including, but not limited to, a spray boom, a hand sprayer, low volume applicators, high and low volume field mounted equipment, aerial sprayers, controlled droplet applicators, CDA equipment, and combinations thereof.
  • aqueous as used in the specification, is not intended to exclude the presence of a small amount of non-aqueous solvent or dispersions or partial dispersions of the active ingredients disclosed herein.
  • the following examples have been prepared and tested. The examples should not, however, be viewed as limiting the scope of
  • Aqueous solutions containing various combinations and amounts of herbicide, adjuvant, and phosphite were applied to small plots of a target weed and the results were observed.
  • the target weed was Green Panic (panicum maximum, or trichoglume).
  • the plot was about 2 meters by 1.5 meters, with a 50 cm buffer strip between treatments.
  • the treatments were applied by using a 15- liter knapsack sprayer with a four-nozzle (flat fan nozzle) hand sprayer boom. The spray pressure was maintained at 2 bar.
  • inventive compositions employed in each formulation were prepared by combining and diluting glyphosate 360 with AgrifosTM 400 (except sample 7 employed AgrifosTM600).
  • Sample 2 included AgriwetTM 77, which is a monoethanol amine.
  • the surfactant employed was an ethoxylated tallow amine (TAE).
  • Table I provides the constituents of each formulation as well as the death rating that was attributed to each plot after observation on day six after treatment. A rating of 0 indicates that the treatment had no impact on the plant and a rating of 10 indicated complete plant mortality. TABLE I

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Abstract

L'invention concerne une composition pesticide comprenant: a) un composé de phosphite; b) un pesticide; et c) de l'eau.
PCT/US2005/018483 2004-05-25 2005-05-25 Composition pesticide WO2005115144A1 (fr)

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US20100113271A1 (en) * 2008-10-31 2010-05-06 Agro-K Corporation Compositions and methods for providing micronutrients in conjunction with plant growth regulation
US20140031226A1 (en) * 2008-08-26 2014-01-30 Agro-K Corporation Compositions and methods for providing micronutrients to crops
US20150230459A1 (en) * 2006-04-07 2015-08-20 Riken Pesticidal/ovicidal composition and pesticidal/ovicidal method
US10285404B2 (en) 2013-02-27 2019-05-14 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
US10334849B2 (en) 2011-10-26 2019-07-02 Monsanto Technology Llc Salts of carboxylic acid herbicides
US10499646B2 (en) 2004-03-10 2019-12-10 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US10736322B2 (en) 2012-06-04 2020-08-11 Monsanto Technology Llc Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts
US11503826B2 (en) 2009-08-10 2022-11-22 Monsanto Technology Llc Low volatility auxin herbicide formulations

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US6906005B2 (en) * 2000-12-01 2005-06-14 Huntsman Corporation Australia Pty Ltd Herbicidal compositions
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US6908882B1 (en) * 1999-09-09 2005-06-21 Monsanto Company Enhanced method of killing weeds with glyphosate herbicide
US6906005B2 (en) * 2000-12-01 2005-06-14 Huntsman Corporation Australia Pty Ltd Herbicidal compositions
US6881707B2 (en) * 2001-08-03 2005-04-19 Nufarm Limited Glyphosate composition
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US10499646B2 (en) 2004-03-10 2019-12-10 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US11864558B2 (en) 2004-03-10 2024-01-09 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US20150230459A1 (en) * 2006-04-07 2015-08-20 Riken Pesticidal/ovicidal composition and pesticidal/ovicidal method
US10130094B2 (en) * 2006-04-07 2018-11-20 Riken Pesticidal/ovicidal composition and pesticidal/ovicidal method
US8288437B2 (en) 2008-07-24 2012-10-16 Valent Biosciences Corporation Salts, aqueous liquid compositions containing salts of abscisic acid analogs and methods of their preparation
WO2010011802A1 (fr) * 2008-07-24 2010-01-28 Valent Biosciences Corporation Sels, compositions liquides aqueuses de sels d'analogues d'acide abscissique et procédés pour les préparer
US20140031226A1 (en) * 2008-08-26 2014-01-30 Agro-K Corporation Compositions and methods for providing micronutrients to crops
US10631542B2 (en) * 2008-10-31 2020-04-28 Agro-K Corporation Compositions and methods for providing micronutrients in conjunction with plant growth regulation
US20100113271A1 (en) * 2008-10-31 2010-05-06 Agro-K Corporation Compositions and methods for providing micronutrients in conjunction with plant growth regulation
US11503826B2 (en) 2009-08-10 2022-11-22 Monsanto Technology Llc Low volatility auxin herbicide formulations
US10334849B2 (en) 2011-10-26 2019-07-02 Monsanto Technology Llc Salts of carboxylic acid herbicides
US10736322B2 (en) 2012-06-04 2020-08-11 Monsanto Technology Llc Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts
US10285404B2 (en) 2013-02-27 2019-05-14 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
US11399544B2 (en) 2013-02-27 2022-08-02 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility

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