WO2014059125A1 - Alkylbenzene sulfonate surfactants for controlling herbicide spray drift - Google Patents
Alkylbenzene sulfonate surfactants for controlling herbicide spray drift Download PDFInfo
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- WO2014059125A1 WO2014059125A1 PCT/US2013/064307 US2013064307W WO2014059125A1 WO 2014059125 A1 WO2014059125 A1 WO 2014059125A1 US 2013064307 W US2013064307 W US 2013064307W WO 2014059125 A1 WO2014059125 A1 WO 2014059125A1
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- herbicide
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- glyphosate
- alkylbenzene sulfonate
- choline
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Definitions
- Spray drift during aqueous herbicide application can be reduced by incorporating one or more alkylbenzene sulfonate surfactants into an aqueous herbicidal spray mixture.
- the methods to reduce spray drift during the application of an aqueous herbicidal spray mixture containing a herbicide include incorporating into the aqueous herbicidal spray mixture from 0.01 to 10 weight percent of one or more alkylbenzene sulfonate surfactants.
- aqueous concentrate compositions include from about 0.1 to about 95 weight percent of a water soluble salt of at least one herbicide and from about 0.01 to about 20 weight percent of one or more alkylbenzene sulfonate surfactants.
- the methods and compositions reduce the amount of driftable fines of a herbicide spray in both aerial and ground spray applications.
- the methods include the use of aqueous herbicidal spray mixtures incorporating one or more alkylbenzene sulfonate surfactants and one or more herbicides.
- Herbicides useful with the methods and compositions described herein include auxinic herbicides such as, for example, triclopyr, 2,4-D, 2,4-DB, MCPA, MCPB, or mixtures thereof.
- the methods described herein are most particularly useful for the application of herbicides that are subject to restricted applications around sensitive crops such as spray mixtures containing glyphosate, 2,4-D, triclopyr, or mixtures thereof.
- alkylbenzene sulfonate surfactants useful with the methods and compositions described herein have the following general formula I:
- the R group can be in the ortho-, meta-, or para-position and is a linear or branched Cs-Cis alkyl group.
- the R group can be a linear dodecyl (C 12 ) alkyl chain or a branched C 12 alkyl chain.
- the R group can be attached to the benzene ring of the alkylbenzene sulfonate surfactant molecule at any position along the R group.
- suitable X + cations include isopropyl ammonium, dimethyl ammonium, triethyl ammonium, monoethanol ammonium, diethanol ammonium, triethanol ammonium, dimethylethanol ammonium, diethyleneglycol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium, choline, calcium, magnesium, potassium and sodium.
- an alkylbenzene sulfonate surfactant can include a mixture of linear and/or branched R groups with an array of different lengths (e.g., Cs-Cis) attached to the alkylbenzene sulfonate surfactant molecules at different positions along the R group.
- an alkylbenzene sulfonate surfactant can include a mixture of molecules with a uniform length R group (e.g., C 12 ) attached to alkylbenzene sulfonate surfactant molecules at different positions along the R group.
- R group e.g., C 12
- Biosoft ® N-411 (Stepan Company; Northfield, Illinois) is a commercially available example of a linear alkylbenzene sulfonate as an isopropyl amine salt (indicated to be >90 isopropylamine dodecylbenzenesulfonate).
- Ninate ® 411 (Stepan Company) is a commercially available example of a branched alkylbenzene sulfonate as an isopropyl amine salt (indicated to include a mixture of branched C9-C17 R groups).
- Ninate ® 60L (Stepan Company) is a commercially available example of a linear alkylbenzene sulfonate as the calcium salt (indicated to include a linear C 12 R group).
- the one or more alkylbenzene sulfonate surfactants can be incorporated into an aqueous herbicidal spray mixture, for example, by being tank-mixed directly with a diluted herbicidal formulation.
- the one or more alkylbenzene sulfonate surfactants may be incorporated into the aqueous herbicidal spray mixture at a concentration from 0.01 to 10 weight percent of the final spray mixture. Additional examples of concentrations for the one or more alkylbenzene sulfonate surfactants incorporated into the aqueous herbicidal spray mixture include, from 0.01 to 9 weight percent of the final spray mixture, from 0.01 to 8 weight percent of the final spray mixture, from 0.01 to 7 weight percent of the final spray mixture, from 0.01 to 6 weight percent of the final spray mixture, from 0.01 to 5 weight percent of the final spray mixture, from 0.01 to 4.5 weight percent of the final spray mixture, from 0.01 to 4 weight percent of the final spray mixture, from 0.01 to 3.5 weight percent of the final spray mixture, from 0.01 to 3 weight percent of the final spray mixture, from 0.01 to 2.5 weight percent of the final spray mixture, from 0.01 to 2 weight percent of the final spray mixture, from 0.01 to 1.5 weight percent of the final spray mixture, and from
- aqueous herbicidal spray mixtures disclosed herein may include insecticides, herbicide safeners, or fungicides, and the aqueous herbicidal spray mixtures may be applied for the control of unwanted plants, fungi, or insects at levels dependent upon the
- aqueous herbicidal spray mixtures as described herein may be applied in conjunction with one or more other active ingredients to control a wider variety of unwanted plants, fungi, or insects.
- the presently claimed compositions can be formulated with the other active ingredient or active ingredients as premix concentrates, tank-mixed with the other active ingredient or active ingredients for spray application, or applied sequentially with the other active ingredient or active ingredients in separate spray applications.
- An example of a composition as described herein that may be used in conjunction with another active ingredient comprises an aqueous pre-mix concentrate containing a mixture of glyphosate and an auxinic herbicide such as a water soluble salt of 2,4-D, a water soluble salt of triclopyr, or mixtures thereof.
- Such aqueous pre-mix herbicidal concentrates may be diluted from 1 to 2000 fold in water at the point of use depending upon the agricultural practices and used in spray applications to control weeds in crops.
- the aqueous herbicidal spray mixtures may contain one or more biocides.
- Biocides may be present in the composition from about 0.001 wt % to about 0.1 wt %.
- the one or more biocides may be present in the composition at 0.001 wt % to 0.1 wt , 0.005 wt % to 0.1 wt , 0.01 wt % to 0.1 wt , 0.02 wt % to 0.1 wt , 0.03 wt % to 0.1 wt , 0.04 wt % to 0.1 wt , 0.05 wt % to 0.1 wt , 0.06 wt % to 0.1 wt , 0.07 wt % to 0.1 wt , 0.08 wt % to 0.1 wt , or 0.09 wt % to 0.1 wt %.
- biocides include, but are not limited to, bactericides, viricides, fungicides, parasiticides, and the like.
- biocide active ingredients include, but are not limited to, phenol compounds (such as phenol, thymol, pentachlorophenol, cresol, and p-chloro-m-xylenol), aldehydic compounds (such as formaldehyde, glutaraldehyde, and paraformaldehyde), acid compounds (such as benzoic acid, sorbic acid, mucochloric acid, and mucobromic acid), esters of p-hydroxybenzoic acid (such as methyl-/?-hydroxybenzoate and butyl-/?- hydroxybenzoate), rare earth salts, amines, disulfides, heterocyclic compounds (such as thiazinium salts, thiazolinones, and benzimidazoles), quaternary ammonium salts, organic mercury compounds, hexamethylene
- Suitable active ingredients for use in the aqueous herbicidal spray mixtures described herein include herbicides such as, for example, auxinic herbicides (such as 2,4-D, 2,4-DB, fluroxypyr, MCPA, MCPB, or triclopyr), acetochlor, atrazine, benfluralin, cloransulam, cyhalofop, diclosulam, dithiopyr, ethalfluralin, florasulam, flumetsulam, glufosinate, glyphosate, haloxyfop, isoxaben, MSMA, oryzalin, oxyfluorfen, pendimethalin, penoxsulam, propanil, pyroxsulam, quizalofop, tebuthiuron, and trifluralin.
- auxinic herbicides such as 2,4-D, 2,4-DB, fluroxypyr, MCPA, MCPB, or tri
- Suitable active ingredients for use in the described compositions also include herbicide safeners such as, for example, cloquintocet, flurazole, mefenpyr, and TI-35.
- Suitable active ingredients for use in the described compositions also include insecticides such as, for example, chlorpyrifos, chlorpyrifos-methyl, gamma-cyhalothrin, cypermethrin, deltamethrin, halofenozide, methoxyfenozide, sulfoxaflor, spinosad, spinetoram, and tebufenozide.
- Suitable active ingredients for use in the described compositions also include fungicides such as, for example, fenbuconazole, mancozeb, myclobutanil, propiconazole, quinoxyfen, thifluzamide, and zoxamide.
- fungicides such as, for example, fenbuconazole, mancozeb, myclobutanil, propiconazole, quinoxyfen, thifluzamide, and zoxamide.
- aqueous herbicidal spray mixtures described herein contain water soluble salts of auxinic herbicides and/or the water soluble salt of glyphosate and/or the water soluble salt of glufosinate
- suitable cations contained in these salts include ammonium, isopropyl ammonium, dimethyl ammonium, triethyl ammonium, monoethanol ammonium, diethanol ammonium, triethanol ammonium, dimethylethanol ammonium, diethyleneglycol ammonium, triisopropanol ammonium, tetramethyl ammonium, tetraethyl ammonium, choline, and potassium.
- useful 2,4-D salts include the 2,4-D choline salt and the 2,4-D dimethyl ammonium salt
- useful glyphosate salts include the glyphosate dimethyl ammonium salt, the glyphosate isopropyl ammonium salt, and the glyphosate potassium salt
- useful glufosinate salts include glufosinate ammonium.
- the auxinic herbicide is 2,4-D choline salt or 2,4-D dimethyl ammonium salt and the glyphosate is glyphosate dimethyl ammonium salt, glyphosate isopropyl ammonium salt, or glyphosate potassium salt.
- the auxinic herbicide is 2,4-D choline salt or 2,4-D dimethyl ammonium salt
- the glyphosate is glyphosate dimethyl ammonium salt
- glyphosate isopropyl ammonium salt
- the one or more alkylbenzene sulfonate surfactants are alkyl amine salts of alkylbenzene sulfonic acids, e.g., branched alkylbenzene sulfonic acids.
- the auxinic herbicide is 2,4-D choline salt
- the glyphosate is glyphosate dimethyl ammonium salt
- the one or more alkylbenzene sulfonate surfactants are isopropyl amine salts of alkylbenzene sulfonate surfactants.
- the auxinic herbicide is 2,4-D choline salt or 2,4-D dimethyl ammonium salt and the glufosinate is glufosinate ammonium salt.
- the auxinic herbicide is 2,4- D choline salt or 2,4-D dimethyl ammonium salt
- the glufosinate is glufosinate ammonium salt
- the one or more alkylbenzene sulfonate surfactants are alkyl amine salts of alkylbenzene sulfonic acids, e.g., branched alkylbenzene sulfonic acids.
- the auxinic herbicide is 2,4-D choline salt
- the glufosinate is glufosinate ammonium salt
- the one or more alkylbenzene sulfonate surfactants are isopropyl amine salts of alkylbenzene sulfonate surfactants.
- the optimum spray droplet size depends on the application for which the herbicidal composition is used. If droplets are too large, there will be less coverage by the spray; i.e, large droplets will land in certain areas while areas in between will receive little or no spray coverage. The maximum acceptable droplet size may depend on the amount of composition being applied per unit area and the need for uniformity in spray coverage.
- spray droplet size may also depend upon the spray apparatus, e.g., nozzle size and configuration.
- the reduction in spray drift may result from a variety of factors including a reduction in the production of fine spray droplets ( ⁇ 150 ⁇ minimum diameter) and an increase in the volume median diameter (VMD) of the spray droplets.
- VMD volume median diameter
- the median diameter of the plurality of spray droplets created using the compositions and methods described herein is increased above that of a spray composition that does not include the one or more alkylbenzene sulfonate surfactants as described herein.
- aqueous concentrate compositions are solutions containing high concentrations of an aqueous herbicidal spray component described above, i.e., one or more water soluble auxinic herbicide salts and one or more alkylbenzene sulfonate surfactants.
- the aqueous concentrate compositions are intended to be diluted to provide aqueous herbicidal spray mixtures for use, for example, with the methods described herein.
- the aqueous concentrate compositions include from 0.1 to 95 weight percent of one or more water soluble salts of at least one herbicide and from 0.01 to 20 weight percent of one or more alkylbenzene sulfonate surfactants.
- the aqueous concentrate compositions can additionally include glyphosate.
- the aqueous concentrate compositions can contain about 10 to about 45 weight percent of the water soluble glyphosate salt; about 10 to about 45 weight percent of the one or more water soluble auxinic herbicide salts; and 0.1 to 18 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1 to 16 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1 to 14 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1 to 12 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1 to 10 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1 to 9 weight percent of the one or more alkylbenzene sulfonate surfactants, 0.1
- aqueous concentrate compositions can be stored in suitable containers as will be readily recognized by one of skill in the art and can be, for example, solutions, emulsions, or suspensions.
- the auxinic herbicide is 2,4-D choline salt or 2,4-D dimethyl ammonium salt and the glyphosate is glyphosate dimethyl ammonium salt, or glyphosate isopropyl ammonium salt.
- the auxinic herbicide is 2,4-D choline salt or 2,4-D dimethyl ammonium salt
- the glyphosate is glyphosate dimethyl ammonium salt
- glyphosate isopropyl ammonium salt
- the one or more alkylbenzene sulfonate surfactants are isopropyl amine salts of alkylbenzene sulfonic acids, e.g., branched alkylbenzene sulfonic acids.
- the auxinic herbicide is 2,4-D choline salt
- the glyphosate is glyphosate dimethyl ammonium salt
- the one or more alkylbenzene sulfonate surfactants are isopropyl amine salts of alkylbenzene sulfonic acids, e.g., branched alkylbenzene sulfonic acids.
- Aqueous solutions i.e., including both concentrates and spray solutions, containing 2,4-D and glyphosate are prone to incompatibility under certain conditions and
- compositions leading to product performance issues and difficulty in using the products i.e., difficulty with field applications of the products.
- Incompatibility in concentrate compositions is minimized by the use of very small amounts of 2,4-D, such as less than about 3 wt % ae (acid equivalent) relative to the total composition.
- High-strength aqueous compositions of certain organo ammonium salts of 2,4-D and glyphosate where the weight ratio (ae basis) of the 2,4-D salt to the glyphosate salt is from about 2.3:1 to about 1:2.3 and the compositions may contain up to or greater than 350 grams of acid equivalent per litre (g ae/L) of total active ingredients are described in U.S.
- compositions are generally, though not necessarily, homogeneous and free-flowing at temperatures ranging from 54 °C to about -10 °C.
- the compositions described herein may additionally contain surfactants.
- compositions as described that include glyphosate can optionally include an efficacy enhancing surfactant.
- the surfactants may be anionic, cationic, or nonionic in character.
- typical surfactants include alcohol- alky lene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; ethoxylated amines, such as
- betaine surfactants such as cocoamidopropyl betaine; fatty acid amidopropyl dimethylamine surfactants such as cocoamidopropyl dimethylamine; alky lpoly glycoside surfactants; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; and mixtures thereof.
- the additional surfactant or mixture of surfactants is usually present at a concentration of from about 0.5 to about 20 weight percent of the formulation.
- compositions optionally containing one or more additional compatible ingredients are provided herein.
- additional ingredients may include, for example, one or more pesticides or other ingredients, which may be dissolved or dispersed in the composition and may be selected from acaricides, bactericides, fungicides, insecticides, herbicides, herbicide safeners, insect attractants, insect repellents, plant activators, plant growth regulators, and synergists.
- any other additional ingredients providing functional utility such as, for example, dyes, stabilizers, fragrants, viscosity-lowering additives, compatibility agents, and freeze-point depressants may be included in these compositions.
- Aqueous concentrate compositions are also described that can be used as herbicide tank- mix additives to reduce spray drift during herbicide spray applications.
- These aqueous concentrate compositions can include from 0.01 to 90 weight percent of one or more alkylbenzene sulfonate surfactants as described above.
- Such aqueous concentrate compositions are combined at tank mixing with herbicides as described above to reduce spray drift during application of the tank mix.
- 2,4-D choline aqueous concentrates with built-in alkylbenzene sulfonate surfactants Aqueous herbicide concentrates containing 383 grams acid equivalent per kilogram (g ae/kg) of 2,4-D choline, 50 g/kg propylene glycol, 2.1 g/kg ethylenediaminetetraacetic acid choline salt (EDTA-choline; prepared by adding 1028.25 g of EDTA acid and 689.7 g of deionized (DI) water into 2310.0 g of choline hydroxide solution (45 wt ) and stirring until all solids are dissolved), and 40 g/kg of an alkylbenzene sulfonate surfactant selected from the following: 1. Ninate 411, isopropyl amine salt of branched dodecylbenzene sulfonic acid (88%)
- a 4-ounce (oz) vial was first charged with 86.00 g of a 44.5 wt % ae 2,4-D choline salt solution in water (prepared by dissolving 4171.0 g of 2,4-D acid flake (technical grade, 97.1 wt %) into 4789.4 g of choline hydroxide solution (45% aqueous solution) under low shear agitation to give a solution with a pH of 7.0 and a density of 1.21 grams per milliliter (g/mL)).
- the two aqueous 2,4-D choline concentrates containing the alkylbenzene sulfonate surfactants and the one aqueous concentrate containing only 2,4-D choline and EDTA- choline (control sample) were each tank-mixed with Roundup PowerMax ® herbicide containing 2 wt % ammonium sulfate (AMS).
- Spray solutions were prepared by combining 5.61 mL of each of the three 2, 4-D choline concentrates and 4.99 mL of Roundup
- PowerMax ® herbicide (540 g ae/L of glyphosate potassium; available from Monsanto, St.Louis, MO) with 289.40 mL of a 2% ammonium sulfate solution in water and then lightly shaking by hand until each spray sample was homogenous.
- the three samples were sprayed using a Teejet ® 8002 flat fan nozzle (Teejet Technologies; Wheaton, IL) at 40 pounds per square inch (psi; 276 kiloPascal) and the spray droplet size distribution was measured with a Sympatec Helos/KF high resolution laser diffraction particle sizer with an R7 lens (Sympatec GmbH; Clausthal-Zellerfeld, Germany).
- the tip of the nozzle was situated 12 inches (30.5 centimeters) above the path of the laser beam of the Sympatec particle sizer.
- the percentage of driftable fines was expressed as the volume percentage of spray droplets below 150 ⁇ volume mean diameter ( VMD) as shown in Table 1.
- Table 1 Spray Droplet Analysis of 2,4-D Herbicide Sprays
- Aqueous herbicide concentrates containing 383 g ae/kg 2,4-D choline, 50 g/kg propylene glycol, 2.1 g/kg ethylenediaminetetraacetic acid choline salt (EDTA-choline), 40 g/kg Ninate® 411, and 10 g/kg each of the following surfactants were prepared as described below:
- Rhodamox® LO N, N-dimethy ldodecan- 1 - amine oxide
- Rhodamox® LO is available from Rhodia-Novecare (Cranbury, NJ); Duomeen®,
- a 4-oz vial was first charged with 86.00 g of a 44.5 wt % ae basis 2,4-D choline salt solution in water. To the vial were added 5.00 g of propylene glycol and 0.84 g of an EDTA- choline aqueous solution (25 wt %), and the liquids were then blended by hand shaking the vial until a homogeneous solution was obtained. To the vial were then added 4.00 g of Ninate 411, 1.00 g of a surfactant from the list above and enough deionized water to make 100 g of a homogenous herbicide concentrate after blending. Five aqueous concentrates containing Ninate® 411 and one of the surfactants shown above, and one aqueous concentrate containing only 2,4-D choline and EDTA-choline (control sample) were prepared in this manner.
- the five aqueous 2,4-D choline concentrates containing Ninate® 411 and a surfactant from the list above, and the one aqueous concentrate containing only 2,4-D choline and EDTA-choline (control sample) were each tank-mixed with an aqueous solution of Roundup PowerMax ® herbicide diluted in either deionized water or 2 wt % AMS.
- Spray solutions were prepared by combining 5.61 mL of each of the six 2, 4-D choline concentrates and 4.99 mL of Roundup PowerMax ® herbicide (540 g ae/L of glyphosate potassium; available from Monsanto, St.Louis, MO) with 289.40 mL of either deionized water (Spray Solutions A) or a 2% AMS solution in water (Spray Solutions B). Each of the 12 samples was lightly shaken by hand until homogenous and then was sprayed using the same procedure and equipment described in Example 1. The percentage of driftable fines was expressed as the volume percentage of spray droplets below 150 ⁇ volume mean diameter (VMD) as shown in Table 2.
- VMD volume mean diameter
- Rhodamox® LO is available from Rhodia-Novecare (Cranbury, NJ);
- Control sample 2 contains Ninate® 411 and no other surfactants.
- Glyphosate aqueous concentrates with built-in alkylbenzene sulfonate surfactants are built-in alkylbenzene sulfonate surfactants.
- Aqueous herbicide concentrates containing 406 g ae kg of glyphosate potassium, 2.5 g kg ethylenediaminetetraacetic acid choline salt (EDTA-choline) and 40 g kg alkylbenzene sulfonate surfactant were prepared.
- a 4-oz vial was first charged with 90.00 g of commercial RoundUp PowerMax® herbicide solution (containing 540 g ae/L of glyphosate potassium; Monsanto; St. Louis, MO).
- the aqueous RoundUp PowerMax® herbicide concentrates containing Ninate® 411 or Ninate® 60L and the aqueous concentrate containing only RoundUp PowerMax® herbicide and EDTA-choline (control sample) were each diluted in either deionized water or a 2 wt % AMS solution in water.
- Spray solutions were prepared by diluting 10 mL of each of the 3 glyphosate concentrates with 490 mL of either deionized water (Spray Solutions A) or a 2% AMS solution in water (Spray Solutions B). Each of the 6 samples was lightly shaken by hand until homogenous and then was sprayed using the same procedure and equipment as described in Example 1. The percentage of driftable fines was expressed as the volume percentage of spray droplets below 150 ⁇ volume mean diameter (VMD) as shown in Table 3.
- VMD volume mean diameter
- Ninate ® 411 and Ninate ® 60L are available from Stepan Company (Northfield, IL)
- Aqueous herbicide concentrates containing 500 g ae/kg 2,4-D dimethylamine (DMA), 2.5 g/kg ethylenediaminetetraacetic acid choline salt (EDTA-choline), 40 g/kg Ninate® 411, and 10 g/kg of Duomeen® T (tallowalkyldiamine) surfactant were prepared.
- DMA 2,4-D dimethylamine
- EDTA-choline ethylenediaminetetraacetic acid choline salt
- Ninate® 411 40 g/kg Ninate® 411
- Duomeen® T tallowalkyldiamine
- aqueous 2,4-D DMA concentrate containing the Ninate® 411 and Duomeen® T and the aqueous concentrate containing only 2,4-D DMA and EDTA-choline (control sample) were each tank-mixed with an aqueous solution of Roundup PowerMax ® herbicide diluted in either deionized water or 2 wt % AMS in water.
- Spray solutions were prepared by combining 5.61 mL of the 2,4-D DMA concentrates and 4.99 mL of Roundup PowerMax ® herbicide (540 g ae/L of glyphosate potassium; available from Monsanto, St.Louis, MO) with 289.40 mL of either deionized water (Spray Solutions A) or a 2% AMS solution in water
- duomeen® products are available from AkzoNobel (Chicago, IL); 2 Control
- Glufosinate ammonium aqueous concentrates with built-in alkylbenzene sulfonate surfactants :
- Aqueous herbicide concentrates containing 274 g ae/kg of glufosinate ammonium, 2.5 g/kg ethylenediaminetetraacetic acid choline salt (EDTA-choline) and 40 g/kg Ninate® 411 (alkylbenzene sulfonate surfactant) were prepared.
- a 4-oz vial was first charged with 90.00 g of a 30 wt % glufosinate ammonium herbicide solution (prepared by dissolving 90 g of glufosinate ammonium salt in 210 g of water).
- EDTA- choline aqueous solution 25 wt %) and 4.00 g of Ninate ® 411 (IPA salt), and the liquids were then blended by hand shaking the vial until a homogeneous solution was obtained.
- Deionized water was added to the vial to make 100 g of a homogenous herbicide concentrate after blending.
- One aqueous glufosinate ammonium concentrate containing Ninate® 411 and one aqueous glufosinate ammonium concentrate containing no Ninate® 411 (control sample) were prepared in this manner.
- aqueous glufosinate ammonium concentrate containing alkylbenzene sulfonate surfactants and the aqueous concentrate containing only glufosinate ammonium and EDTA- choline were each diluted in either deionized water or a 2 wt % AMS solution in water.
- Spray solutions containing glufosinate ammonium were prepared by diluting 10 mL of each of the glufosinate concentrates with 490 mL of either deionized water (Spray Solutions A) or a 2% AMS solution in water (Spray Solutions B).
- Aqueous herbicide concentrates containing 350 g ae/kg triclopyr choline, 2.5 g/kg ethylenediaminetetraacetic acid choline salt (EDTA-choline) and 40 g/kg Ninate® 411 were prepared.
- a 4-oz vial was first charged with 90.00 g of a 39.0 wt % (ae basis) triclopyr choline salt solution in water.
- To the vial was added 1.0 g of an EDTA-choline aqueous solution (25 wt %), and the liquids were then blended by hand shaking the vial until a homogeneous solution was obtained.
- Ninate ® 411 To the vial was then added 4.00 g of Ninate ® 411 and enough deionized water to make 100 g of a homogenous herbicide concentrate after blending.
- One aqueous concentrate containing triclopyr choline, EDTA-choline and Ninate® 411 and one aqueous concentrate containing only triclopyr choline and EDTA-choline (control sample) were prepared in this manner.
- Triclopyr choline herbicide spray solutions and spray droplet analysis Triclopyr choline herbicide spray solutions and spray droplet analysis:
- aqueous triclopyr choline concentrate containing Ninate® 411 and the aqueous concentrate containing only triclopyr choline and EDTA-choline (control sample) were each tank-mixed with an aqueous solution of Roundup PowerMax ® herbicide diluted in either deionized water or a 2 wt % AMS solution in water.
- Spray solutions were prepared by combining 6.0 mL of each triclopyr choline concentrate and 4.99 mL of Roundup PowerMax herbicide (540 g ae/L of glyphosate potassium; available from Monsanto, St.Louis, MO) with 289.01 mL of either deionized water (Spray Solutions A) or a 2% AMS solution in water (Spray Solutions B). Each of the spray samples was lightly shaken by hand until homogenous and then was sprayed using the same procedure and equipment described in Example 1. The percentage of driftable fines was expressed as the volume percentage of spray droplets below 150 ⁇ volume mean diameter (VMD) as shown in Table 6.
- VMD volume mean diameter
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Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015536887A JP2015531409A (en) | 2012-10-12 | 2013-10-10 | Alkylbenzenesulfonate surfactants for controlling spray drift of herbicides |
MX2015004552A MX2015004552A (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift. |
IN3002DEN2015 IN2015DN03002A (en) | 2012-10-12 | 2013-10-10 | |
EP13845969.8A EP2906039A4 (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
CN201380064736.9A CN104853609A (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
RU2015117435A RU2015117435A (en) | 2012-10-12 | 2013-10-10 | ALKYLBENZENESULPHONATE SURFACE-ACTIVE SUBSTANCES FOR CONTROL OF DEMOCRACY OF HERBICIDES DURING SPRAYING |
CA 2887364 CA2887364A1 (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
AU2013329229A AU2013329229A1 (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
IL238154A IL238154A0 (en) | 2012-10-12 | 2015-04-02 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
HK16101199.9A HK1213145A1 (en) | 2012-10-12 | 2016-02-02 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
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US201261713053P | 2012-10-12 | 2012-10-12 | |
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PCT/US2013/064307 WO2014059125A1 (en) | 2012-10-12 | 2013-10-10 | Alkylbenzene sulfonate surfactants for controlling herbicide spray drift |
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US (1) | US20140106972A1 (en) |
EP (1) | EP2906039A4 (en) |
JP (1) | JP2015531409A (en) |
CN (1) | CN104853609A (en) |
AR (1) | AR093006A1 (en) |
AU (1) | AU2013329229A1 (en) |
BR (1) | BR102013026403A2 (en) |
CA (1) | CA2887364A1 (en) |
HK (1) | HK1213145A1 (en) |
IL (1) | IL238154A0 (en) |
IN (1) | IN2015DN03002A (en) |
MX (1) | MX2015004552A (en) |
RU (1) | RU2015117435A (en) |
UY (1) | UY35076A (en) |
WO (1) | WO2014059125A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105916377A (en) * | 2013-12-10 | 2016-08-31 | 美国陶氏益农公司 | Synergistic herbicidal weed control and improved crop tolerance from combinations of 2,4-D-choline and glufosinate in 2,4-D- and glufosinate-tolerant soybeans, corn, cotton |
EP3064062A1 (en) * | 2015-03-05 | 2016-09-07 | Clariant International Ltd | Use of a composition for reducing the drift when applying a plant treatment composition |
EP3331360A4 (en) * | 2015-08-07 | 2019-01-09 | Rhodia Operations | Choline salt and ammonium-free adjuvants for water conditioning and agricultural formulations |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112752507B (en) * | 2018-10-31 | 2022-07-29 | 花王株式会社 | Herbicidal composition |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681443A (en) * | 1969-05-21 | 1972-08-01 | Witco Chemical Corp | Retardation of formation of color-forming bodies in alkylaryl sulfonic acids |
WO2001089302A2 (en) * | 2000-05-19 | 2001-11-29 | Monsanto Technology, Llc | Aqueous pesticide formulations and novel surfactants |
WO2003096807A1 (en) * | 2002-05-14 | 2003-11-27 | Huntsman Petrochemical Corporation | Agricultural formulations containing enhanced surfactants |
US20100009937A1 (en) * | 2006-09-22 | 2010-01-14 | Huntsman Petrochemical Corporation | Pesticide formulation with streaming birefringence |
US20100105558A1 (en) * | 2008-10-29 | 2010-04-29 | Dow Agrosciences Llc | Stable emulsifiable concentrates containing a first herbicidal carboxylic acid salt and a second herbicidal carboxylic acid ester |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3869276A (en) * | 1972-05-01 | 1975-03-04 | Ciba Geigy Corp | Novel industrial weed control compositions |
DE2422954A1 (en) * | 1974-05-11 | 1975-11-13 | Bayer Ag | MEANS TO REDUCE THE DRIFT DURING THE APPLICATION OF AQUATIC SPRAY MIXTURES OF PLANT PROTECTION PRODUCTS |
US5707928A (en) * | 1993-09-28 | 1998-01-13 | American Cyanamid Company | Emulsifiable suspension concentrate compositions of imidazolinyl benzoic acids, esters and salts thereof, and dinitroaniline herbicides |
GB2306965B (en) * | 1995-11-06 | 1999-09-01 | American Cyanamid Co | Aqueous spray compositions |
US7651977B2 (en) * | 2004-10-28 | 2010-01-26 | Valent U.S.A. Corporation | Herbicidal compositions |
WO2007030886A1 (en) * | 2005-09-16 | 2007-03-22 | Nufarm Australia Limited | Herbicide mixtures and process for preparation thereof |
UA115965C2 (en) * | 2010-08-24 | 2018-01-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | COMPOSITION AND METHOD FOR IMPROVING THE COMPATIBILITY OF WATER-SOLUBLE HERBICIDE SALTS |
CN103209591B (en) * | 2010-09-15 | 2015-08-26 | 陶氏益农公司 | For controlling amine and the oxide surfactant of herbicide sprays drift |
EA022869B1 (en) * | 2011-02-28 | 2016-03-31 | Басф Се | Composition comprising a pesticide, a surfactant and an alkoxylate of 2-propylheptylamine |
US20130150241A1 (en) * | 2011-04-20 | 2013-06-13 | Huntsman Petrochemical Llc | Spray drift reduction agents comprising low hydrophilic-lipophilic balance surfactants |
-
2013
- 2013-10-10 CA CA 2887364 patent/CA2887364A1/en not_active Abandoned
- 2013-10-10 CN CN201380064736.9A patent/CN104853609A/en active Pending
- 2013-10-10 RU RU2015117435A patent/RU2015117435A/en not_active Application Discontinuation
- 2013-10-10 EP EP13845969.8A patent/EP2906039A4/en not_active Withdrawn
- 2013-10-10 JP JP2015536887A patent/JP2015531409A/en active Pending
- 2013-10-10 WO PCT/US2013/064307 patent/WO2014059125A1/en active Application Filing
- 2013-10-10 MX MX2015004552A patent/MX2015004552A/en unknown
- 2013-10-10 US US14/050,939 patent/US20140106972A1/en not_active Abandoned
- 2013-10-10 AU AU2013329229A patent/AU2013329229A1/en not_active Abandoned
- 2013-10-10 IN IN3002DEN2015 patent/IN2015DN03002A/en unknown
- 2013-10-11 UY UY0001035076A patent/UY35076A/en not_active Application Discontinuation
- 2013-10-11 AR ARP130103719A patent/AR093006A1/en unknown
- 2013-10-14 BR BR102013026403-2A patent/BR102013026403A2/en not_active Application Discontinuation
-
2015
- 2015-04-02 IL IL238154A patent/IL238154A0/en unknown
-
2016
- 2016-02-02 HK HK16101199.9A patent/HK1213145A1/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3681443A (en) * | 1969-05-21 | 1972-08-01 | Witco Chemical Corp | Retardation of formation of color-forming bodies in alkylaryl sulfonic acids |
WO2001089302A2 (en) * | 2000-05-19 | 2001-11-29 | Monsanto Technology, Llc | Aqueous pesticide formulations and novel surfactants |
WO2003096807A1 (en) * | 2002-05-14 | 2003-11-27 | Huntsman Petrochemical Corporation | Agricultural formulations containing enhanced surfactants |
US20100009937A1 (en) * | 2006-09-22 | 2010-01-14 | Huntsman Petrochemical Corporation | Pesticide formulation with streaming birefringence |
US20100105558A1 (en) * | 2008-10-29 | 2010-04-29 | Dow Agrosciences Llc | Stable emulsifiable concentrates containing a first herbicidal carboxylic acid salt and a second herbicidal carboxylic acid ester |
Non-Patent Citations (1)
Title |
---|
See also references of EP2906039A4 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105916377A (en) * | 2013-12-10 | 2016-08-31 | 美国陶氏益农公司 | Synergistic herbicidal weed control and improved crop tolerance from combinations of 2,4-D-choline and glufosinate in 2,4-D- and glufosinate-tolerant soybeans, corn, cotton |
CN105979778A (en) * | 2013-12-10 | 2016-09-28 | 美国陶氏益农公司 | Synergistic herbicidal weed control from combinations of 2,4-D-choline and glufosinate |
EP3079470A4 (en) * | 2013-12-10 | 2017-06-21 | Dow AgroSciences LLC | Synergistic herbicidal weed control from combinations of 2,4-d-choline and glufosinate |
EP3064062A1 (en) * | 2015-03-05 | 2016-09-07 | Clariant International Ltd | Use of a composition for reducing the drift when applying a plant treatment composition |
WO2016139358A1 (en) * | 2015-03-05 | 2016-09-09 | Clariant International Ltd | Use of a composition for reducing the drift when applying a plant treatment composition |
CN107426995A (en) * | 2015-03-05 | 2017-12-01 | 科莱恩国际有限公司 | Composition is used for the purposes that drift is reduced when applying plant treatment compositions |
EP3331360A4 (en) * | 2015-08-07 | 2019-01-09 | Rhodia Operations | Choline salt and ammonium-free adjuvants for water conditioning and agricultural formulations |
AU2021201043B2 (en) * | 2015-08-07 | 2022-06-16 | Specialty Operations France | Choline salt and ammonium-free adjuvants for water conditioning and agricultural formulations |
Also Published As
Publication number | Publication date |
---|---|
IN2015DN03002A (en) | 2015-09-25 |
HK1213145A1 (en) | 2016-06-30 |
US20140106972A1 (en) | 2014-04-17 |
IL238154A0 (en) | 2015-05-31 |
CN104853609A (en) | 2015-08-19 |
AU2013329229A1 (en) | 2015-04-23 |
EP2906039A4 (en) | 2016-04-20 |
JP2015531409A (en) | 2015-11-02 |
MX2015004552A (en) | 2015-07-14 |
BR102013026403A2 (en) | 2014-10-29 |
UY35076A (en) | 2014-05-30 |
AR093006A1 (en) | 2015-05-13 |
CA2887364A1 (en) | 2014-04-17 |
EP2906039A1 (en) | 2015-08-19 |
RU2015117435A (en) | 2016-12-10 |
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