WO1989012394A1 - Formulations ameliorees d'herbicides et leur emploi - Google Patents
Formulations ameliorees d'herbicides et leur emploi Download PDFInfo
- Publication number
- WO1989012394A1 WO1989012394A1 PCT/US1989/002570 US8902570W WO8912394A1 WO 1989012394 A1 WO1989012394 A1 WO 1989012394A1 US 8902570 W US8902570 W US 8902570W WO 8912394 A1 WO8912394 A1 WO 8912394A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- roundup
- effective amount
- killing
- plant
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- This invention relates to a method and composition for enhancing the efficacy of herbicides in particular herbicides selected from the group consisting of acifluorfen, its agriculturally acceptable salts, oxyfluorfen, lactofen, imazaquin acid and the agriculturally acceptable salts thereof, N-phosphonomethylglycine and its agriculturally acceptable salts thereof, mixtures thereof and the like.
- This invention also relates to a ready to use composition comprising an enhanced delivery system for herbicides.
- Herbicides may be applied to plants in a variety of methods including different formulations. Of these various methods, use of liquid and dry compositions are quite desirable. The particular formulation desired and resulting efficacy enhancement will greatly depend upon the weed species to be treated, environmental conditions, the geographical area and the climatology of the area at the time of treatment. In many areas of the world, it is highly desirable to apply a herbicide composition having rainfastness quality (adherence to foliage) in areas of high rainfall amounts or under conditions and timing where rainfall is highly likely following application of a herbicide. Further in some areas, it may be particularly desirable to apply herbicide compositions (typically a herbicidal composition) to vegetation which has a thick cuticle and therefore herbicide penetration may be somewhat inhibited.
- herbicide compositions typically a herbicidal composition
- compositions of this invention produced increased herbicide efficacy particularly in applications of a herbicide in accordance with this invention on rhizome johnsongrass, a narrowleaf perennial, and seedling johnsongrass, bamyardgrass and downy brome which are narrlowleaf annuals.
- Glyphosate N-phosphonomethylglycine
- glyphosate has low water solubility, and because of this, commercial formulations contain a water-soluble salt of glyphosate.
- glyphosate is formulated as the isopropylamine salt.
- humectants with certain herbicides is disclosed in "Additives in Herbicide Formulations", Andress G. Kanallopoulos, Sandos, Ltd. Agrochemical Department Switzerland Chemistry and Industry, 7 December 1974, which discloses on page 352 that humectants improve penetration of herbicides into plant leaves by preventing drying of spray deposit, thereby increasing the penetration time.
- This article discloses that glycerol has been used as a humectant with 2,4-D and other herbicides.
- Other glycols disclosed are ethylene and propylene glycol, and polyhdric alcohols in mixtures with free fatty acids and DMSO. Polymeric compounds are reported to be humectants which according to this article includes Carbowax, sucrose, molasses and polypropylenediol.
- compositions and use are also disclosed for glycerol and L-77 in this article.
- Monsanto sells Roundup herbicide EPA Registration No. 524-308-AA (label booklet 1987-4) which is a commercial formulation of the isopropylamine salt of N-phosphonomethylglycine also containing an ethoxylated amine surfactant, inert adjuvants and water.
- silica an organosilicone surfactant, such as Silwet L-77 in tank mixes with commercially purchased Roundup® herbicide at time improves the rainfastness of the resulting formulation of Roundup on some species of weeds.
- Silwet L-77 is antagonistic to Roundup herbicide in such tank mixes with Roundup herbicide when rainfall does not occur after a Roundup composition containing Silwet L-77 (without added humectant) has been applied to many plants, particularly on narrowleaf species.
- Monsanto sells "Pulse” penetrant (which is L-77) for use with Roundup herbicide and discloses on the Pulse label that the addition of Pulse can reduce the rainfree period for Roundup herbicide from 4-6 hours to 2 hours on perennial ryegrass when label recommended rates of Roundup herbicide and Pulse are sprayed on dry foliage.
- Stauffer Australian Patent Application AU-A-64552/86 published May 7, 1987 discloses herbicide compositions comprising (a) an herbicidally effective amount of an agriculturally acceptable salt of N-phosphonomethylglycine, (b) at least one humectant having a moisture capacity substantially equivalent to that of sorbitol; (c) inert adjuvants; and (d) water; wherein the ratio of (a) to (b) ranges from about 1:33 to about 5:1 by weight.
- a herbicidal method of use of such compositions is also disclosed.
- this published patent application discloses that suitable humectants can be employed to keep a salt of N-phosphonomethylglycine moist over a longer period of time on the foliage of plants, thereby enabling it to be absorbed into the foliage in a greater quantity and at a higher rate than would otherwise be possible.
- herbicide formulations retain a significant degree of activity when plants treated therewith are exposed to rain shortly after application, this being a definition of the degree of "rainfastness.” This is particularly important for water-soluble foliar-applied herbicides, such as glyphosate salts.
- It is still yet another object of the invention to provide a herbicidal composition comprising an efficacy increasing amount of a humectant and silicone surfactant.
- this invention provides a novel method and composition for enhancing the efficacy of herbicides, in particular foliar applied herbicides more in particular herbicides selected from the group consisting of acifluorfen (5-(2-chloro- ⁇ -trifluoro-p-tolyloxy)-2-nitrobenzoic acid and its agriculturally acceptable salts thereof, oxyfluorfen (2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene: -lactofen, (1'-(Carboethoxy)ethyl 5-'2-chloro-4-(trifluoromethyl) phenoxyl'-2-nitrobenzoate: imazaquin (2-'4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2--yl'-3-quinolinecarboxylic acid and the agriculturally acceptable salts thereof, N-phosphonomethylgly
- the invention herein comprises a herbicidal composition
- Herbicide compositions herein include both package and tank mix compositions.
- the term agriculturally acceptable as employed herein includes agricultural, industrial and residential uses.
- Herbicides which are useful in this invention include triazines, ureas, carbamates, acetamides, uracils, acetic acid or phenol derivatives, triazoles, benzoic acids, nitriles, diphenyl ethers and the like such as:
- Heterocyclic nitrogen/sulfur derivatives including 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, 2-chloro-4,6-bis(isopropylamino)-s-triazine; 2-chloro-4,6-bis(ethylamine)-s-triazine; 3-isopropyl-1H-2,1, 3-benzothiadiazin-4-(3H)-one 2,2-dioxide, 3-amino-1,2,4-triazole; 5-bromo-3-isopropyl-6-methyluracil; 2-(4-isopropyl-4-methyl-5-oxo-2-imdazolin-2-yl-)3- quinolinecarboxylic acid; isopropylamine salt of 2-(4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid, methyl 6-(4-isopropyl-4-methyl-5-oxo-2-
- herbicides useful for practicing the invention herein include fosamine, haloxyfop, imazapyr, mefluidide, metsulfuron, picloram, quizalofop and imidazolinones.
- N-phosphonomethylglycine itself may be employed in this invention or optionally any agriculturally acceptable salt, amide, ester, or derivative thereof, mixtures of one or more agriculturally acceptable derivatives or salts or mixtures of an agriculturally acceptable salt and N-phosphonomethylglycine may be employed.
- Typical agriculturally acceptable salts which may be employed include those disclosed in US Patents 3,799,758; 4, 405,531; 4,315,765.
- Preferred salts include the isopropylamine, sodium, ammonium, trimethylsulfonium and guanidine salts.
- Other compounds further representative of this class of compounds are those herbicidally active compounds disclosed in U.S. Patents Numbers 3, 455,675; 3,799,758; 3,977,860; 3,868,407; 4,315,765 and 4,397,676.
- Illustrative suitable humectants which may be employed in this invention includes those compounds which absorb water substantially equivalent to glycerin.
- Suitable humectants include sorbitol, polyethylene glycol and poly-propylene glycol, propylene glycol, triethylene glycol, glycerin, sodium stearate, microcrystalline cellulose, homolinear polymers of ethylene oxide and soluble collagen, sold under the tradename collasol by Croda Inc., lactic acid and salts thereof, cane molasses, sodium lactate and the like.
- Illustrative suitable silicone surfactants useful in this invention comprise organosilicone surfactants and polyaklylene oxide modified dimethylpolysiloxane copolymers which are sold under the trademark Silwet, a trademark of Union Carbide Corporation, U.S.A. These are surface active materials and contain discrete hydrophilic (water-loving) and hydrophobic (water-hating) segments. These products have the general formula:
- a ranges from 3 to about 24, b ranges from 0 to about 15, x is in the range from 0 to 3 and y ranges from 1 to 5 and in which "Z" can be hydrogen or a lower alkyl radical having 1-3 carbon atoms or an acyl group having 2 to 4 carbon atoms.
- Silwet silicone surfactants useful in this invention include those described in a trade brochure by Union Carbide entitled Silicones For the Agricultural Industry SUI-356, 6/84, 5M and Surface Active Copolymers also by Union Carbide SUI-394A, 7/85-5M, both of which are incorporated herein in their entirety by reference.
- silicone surfactants which may be employed herein include SF-1188 (General Electric Company, Silicone Products Division, Rubber & Fluid Products Department, Waterford, NY 12188), Silwet L-7607, and Dow Corning Corporation, Midland, MI silicone glycols Q2-5309, Q2-5152, Q2-5852 and Q2-5853 mixtures thereof and the like.
- silicone surfactant is a silicone glycol of the average structure
- Me hereinafter denotes a methyl radical and R is a divalent alkylene group having 2 to 6 carbon atoms, such as ethylene, trimethylene, tetramethylene or hexamethylene. m can be 3 to 24. It is preferred that R is a trimethylene group.
- Z is selected from the group consisting of hydrogen, an alkyl radical having 1 to 3 carbon atoms and an acyl group having 2 to 4 carbon atoms.
- Z is an acetoxy group.
- silicone glycols described above are known in the art and may be prepared by coupling the corresponding allyl-terminated glycol to a bissiloxane structure having a hydrogen attached to the central silicon atom, said structure being
- the coupling is accomplished in the presence of a platinum catalyst.
- a platinum catalyst The skilled artisan will recognize that, in such coupling reactions, a fraction of the allyl-terminated glycol is not converted and will remain as an impurity in the final silicone glycol product.
- Herbicide compositions may contain such impurities and still be within the scope of the present invention.
- Silicone glycol-silicone alkane terpolymers also have utility as a silicone surfactant in the present invention. These compounds may be represented by the average formula
- R is independently selected from alkyl radicals having 1 to 6 carbon atoms;
- A is a linear or branched alkyl radical having 7 to 30 carbon atoms;
- G is a glycol moiety having the formula -R' (OCH 2 CH 2 ) m OZ, in which R' is a divalent alkylene group having 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, an alkyl radical having 1 to 3 carbon atoms and an acyl group having 2 to 4 carbon atoms and m is 8 to about 100;
- Q is independently selected from the group consisting of said alkyl radical A, said glycol moiety G and said alkyl radical R;
- x is 0 to 100, y is 0.1 to 25 and z is 0.1 to 50.
- a highly preferred silicone glycol-silicone alkane terpolymer (II) useful in the present invention as a silicone surfactant has the average structure wherein Me hereinafter denotes a methyl radical.
- silicone glycol-silicone alkane terpolymers described above may be prepared by methods well known in the art. Briefly, the corresponding allylterminated glycol and alpha-alkene are coupled to an SiH-functional siloxane having the average structure
- Coupling is accomplished in the presence of a platinum catalyst at temperatures in the range of about 20 to about 150°C, the reaction preferably being carried out in a solvent such as toluene or isopropanol.
- a solvent such as toluene or isopropanol.
- Illustrative silicone surfactants prepared and utilized to illustrate this invention are hereinafter referred to as fluids.
- compositions of the present invention may also contain other herbicide adjuvants commonly employed in the art.
- adjuvants include crop oil concentrate, ORTHO X-77 spreader, drift control agents, such as LO-DRIFT, defoaming agents, such as D-FOAMER, compatibility agents, such as E-Z MIX, and other adjuvants well known in the herbicide art.
- compositions of the present invention from about 0.1 to about 10 parts by weight of the silicone glycol-silicone alkane terpolymer (II) is thoroughly mixed with each part by weight of herbicide (I). Preferably, from 0.5 to about 5 parts by weight of (II) are employed for each part of the pesticide (I). For a given herbicide, the skilled artisan will readily arrive at a herbicidal composition having the optimum ratio of the ingredients by routine experimentation.
- compositions of this invention may be prepared, for example, by starting with a herbicide and adding in any order the various components of the composition of this invention. For example, one may start with a commercial formulation of the isopropylamine salt of N-phosphonomethylglycine which is an aqueous concentrate containing 480 grams per liter of the isopropylamine salt of N-phosphonomethylglycine (41%) by weight.
- humectant b) silicone surfactant and optionally inert adjuvant and adds any diluent water.
- a herbicide or an agriculturally acceptable salt thereof, or adjuvant, or humectant, or silicone surfactant may be employed if desired in an amount desired.
- the concentration of herbicide active ingredient will be in the range from about 2 to about 70% by weight and preferably in the range from about 4 to about 40 % by weight of the concentrate.
- the concentration of herbicide active ingredient will be in the range from about 0.05% to about 20% by weight and preferably in the range from about 0.15% to about 5% by weight of a final solution illustrative of this invention.
- the ratio of herbicidally active ingredient to silicone surfactant will be about the same whether the composition is a concentrate or a spray.
- the weight ratio of active ingredient to silicone surfactant is from about 1:30 to about 50:1 and preferably in the range from about 1:15 to about 10:1.
- the amount of humectant employed in the herbicide formulation is an amount sufficient to overcome (or safen) any antagonism of silicone surfactant toward the herbicide active and/or to improve rainfastness.
- the ratio of silicone surfactant to humectant in compositions of this invention will be about the same whether the composition is a concentrate or a spray.
- the weight ratio of silicone surfactant to humectant will be in the range from about 1:1 to about 1:200 and preferably in the range from about 1:5 to about 1:50.
- humectant may be employed in this invention which provides the ability to overcome (or to safen) the antagonism of silicone surfactant toward a herbicide active.
- the ratio of herbicide active ingredient to adjuvant will depend to a great deal upon the nature and type of the herbicide active ingredient which is present in the composition. However, typically, the weight ratio of herbicide active ingredient to adjuvant is in the range from about 1:5 to about 10:1 and preferably in the range from about 1:2 to about 4:1.
- the amount of water which is employed to prepare the concentrate or final application concentration, as in a spray, is adjusted as necessary.
- the concentrate and/or final composition may be a dry formulation.
- the phytotoxicant compositions of this invention preferably contain (in addition to the herbicide active, silicone surfactant, and humectant, an inert adjuvant or conditioning agent), one or more surfaceactive agents in amounts sufficient to render a given composition readily dispersible in water or in oil.
- a surface active agent it is understood that wetting agents, dispersing agents , suspending agents and emulsifying agents are included therein.
- Anionic, cationic and nonionic agents can be employed with equal facility.
- Preferred wetting agents are alkyl benzene and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkyl phenols (particularly isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the fatty acid esters of hexito anyhydrides (sorbitan)
- Preferred dispersants are methylcellulose, polyvinylalcohol sodium lignin sulfonates, polymeric alky naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnahp- thalenesul
- Suitable surfactants are disclosed in U.S. Patent 3,799,758 and 4,405,531 supra both of which are incorporated herein in their entirety by reference.
- a particularly preferred composition of this invention comprises the commercial formulation Roundup herbicide, Silwet L-77, glycerine and diluent water.
- a particularly preferred method of use of this invention comprises use of that composition as a post emergent herbicide to kill or control rhizone johnsongrass, seedling johnsongrass, barnyard grass and downy brome.
- Water dispersible powder compositions can be made containing one or more active ingredients, an inert solid extender and one or more wetting and dispersing agents.
- the inert solid extenders are usually of mineral origin such as the natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate.
- the water dispersible powder of this invention usually contain from about 5 to about 95 parts by weight of active ingredient, from about 0.25 to about 25 parts by weight of wetting agent, from about 0.25 to about 25 parts by weight of dispersant and from about 4.5 to about 94.5 parts by weight of inert solid extender, all parts being by weight of the total composition. Where required, from about 0.1 to about 2.0 parts by weight of the solid inert extender can be replaced by a corrosion inhibitor or antifoaming agent or both.
- Aqueous suspensions can be prepared by mixing together and grinding an aqueous slurry of water-insoluble active ingredient in the presence of dispersing agents to obtain a concentrated slurry of very finely divided particles.
- the resulting concentrated aqueous suspension is characterized by its extremely small particle size so that when diluted and sprayed, coverage is very uniform.
- composition of this invention can also contain other additaments, for example fertilizers, phytotoxicants and plant growth regulants, herbicides and the like used as adjuvants or in combination with any of the above described adjuvants, it is preferred to employ the compositions of this invention along with sequential treatments with other phytotoxicants, fertilizers and the like for maximum effect.
- Composition of this invention can also be admixed with other material fertilizers, phytotoxicants and applied in a single application.
- Chemicals useful in combination with the active ingredients of this invention either simultaneously or sequentially including for example triazine, ureas,, carbamates, acetamides, uracils, acetic acids, phenols, thiocarbamates, triazoles, benzoic acids, nitriles and the like.
- herbicide for example, amounts of herbicide which kill or control plants, further for example effective amounts of N-phosphonomethylglycine or agriculturally acceptable salts thereof or derivatives are applied to above ground portions of plants (foliage in particular).
- the application of liquid and particulate solid herbicidal compositions to above ground portions of plants can be carried out by conventional methods, e.g. boom and hand application including sprayers or dusters.
- the composition can also be applied aerially as spray if desired.
- the application of an effective amount of the herbicide composition of this invention to selected locus such as a plant foliage is essential for the practice of this invention.
- the amount of herbicide active ingredient to be employed is dependent upon the response desired in the plant as well as such other factors as the plant species and stage of development thereof, the amount of rainfall as well as the specific herbicide employed. It is believed that one skilled in the art can readily determine from the teachings of this specification including examples, the approximate application rate.
- the narrowleaf and broadleaf test weeds were seeded separately into plastic pots 4 inches in diameter and 3 inches deep with drainage holes on the bottom.
- the pots contained Dupo silt loam soil obtained from the St. Charles Research Farm of Monsanto Company located in St. Charles, Missouri. Prior to use, the soil was steam sterilized at a temperature of 180 Degrees Fahrenheit.
- the soil used was either mixed with a slow release 14-14-14 fertilizer so as to prefertilize it or in some cases where the soil was not prefertilized, the soil was fertilized with a 5% commercial Rapid-Gro fertilizer solution via sub-irrigation 3 to 5 days prior to treating the plants in the pots with the chemical compositions.
- Seedling johnsongrass, barnyardgrass, downy brome, velvetleaf, crabgrass, cocklebur and redroot pigweed were started from seeds, rhizome johnsongrass plants were grown from rhizome pieces and yellow nutsedge from tubers. In all cases, sufficient seeds or stock propagules were planted to produce several seedlings in each pot. Approximately 7 to 10 days after seeding, the velvetleaf, cocklebur and redroot pigweed seedlings were thinned out leaving 2 to 3 healthy seedlings per pot.
- the pots were moved into the greenhouse and placed on trays with each tray holding 40 to 60 pots.
- the trays were lined with absorbent mats for sub-irrigation.
- the greenhouse temperature was maintained at 86 Degrees Fahrenheit during the day and 70 Degrees Fahrenheit during the night. Photoperiod in the greenhouse was maintained at 14 to 16 hours daylength using supplemental lighting.
- the seeded pots were watered via subirrigation as required.
- the chemical treatments were applied within 14 to 21 days after planting. At that time, the narrowleaf weeds were approximately 4 to 16 inches tall while the broadleaf weeds were 1 to 4 inches tall.
- compositions illustrative of compositions of this invention used in the tests were formulated as tank mixtures the same day of application.
- the formulations comprised an agriculturally acceptable salt of N-phosphonomethylglycine namely the isopropylamine salt, an inert adjuvant as a surfactant, a humectant, an organosilicone surface active copolymer and water.
- Rates of application based on N-phosphonomethyglycine ranged from about 1/8 to about 3 pounds glyphosate acid equivalent per acre.
- the ingredient ratios employed in the formulations were glyphosate to surfactant, about 1:0.125 to 1:1, surfactant to silicone 1:0.45 to 1:20, silicon surfactant to humectant about 1:1 to about 1:200.
- Rainfall treatment was applied one hour after spraying of the compositions using a rain tower calibrated to deliver approximately 1/4 inch of simulated rainfall within a period of about 15 minutes.
- compositions and method of use of this invention there is comparative data obtained therewith in various columns and lines for compositions typical of prior art tank mixes comprising Roundup® herbicide with L-77 added, Roundup® herbicide without added Silwet L-77 and Roundup® herbicide with glycerin (but no added silicone surfactant).
- a.e. acid equivalent means acid equivalent of glyphosate acid (N-phosphonomethylglycine).
- SF-1188 is a silicone fluid comprising a copolymer of a polydimethylsiloxane and a polyoxyalkylene ether made and sold by General Electric Company, Silicone Products Division, Waterford, NY 12188.
- MON-0139/Arquad T50 (8:1) 43 100 72 MON-0139/Arquad T50 + 0.25% L-77 10 43 27
- MON-0139/Ethoquad 0-25 (8:1) 20 99 59 MON-0139/Ethoquad 0-25 + 0.25% L-77 7 33 20 MON-0139/Ethoquad 0-25 + 0.25% L-77 + 5% Glycerin 99 100 99
- R is from tallow
- R is from tallow
- R fatty acid
- MON-0139/MON-0818 (4:1) 23 70 47 MON-0139/MON-0818 + 0.25% L-77 68 87 78 MON-0139/MON-0818 + 0.25% L-77 + 5% Glycerin 77 87 82 MON-0139/MON-0818 (8:1) 20 68 44
- MON-0139/Arquad T50 (2:1) 25 78 52 MON-0139/Arquad T50 + 0.25% L-77 25 58 42 MON-0139/Arquad T50 + 0.25% L-77 + 5% Glycerin 73 93 83
- MON-0139/Arquad T50 (4:1) 3 72 38 MON-0139/Arquad T50 + 0.25% L-77 55 75 65 MON-0139/Arquad T50 + 0.25% L-77 + 5% Glycerin 65 88 77
- MON-0139/Arquad T50 (8:1) 5 60 32 MON-0139/Arquad T50 + 0.25% L-77 60 77 68 MON-0139/Arquad T50 + 0.25% L-77 + 5% Glycerin 75 83 79
- MON-0139/Arquad B-100 (8:1) 3 63 33 MON-0139/Arquad B-100 + 0.25% L-77 60 90 75
- Witconate X-7163 is of the formula
- Igepal CA-720 C 8 H 17 —O—(CH 2 CH 2 O) 12.5 H
- Sterox NJ C 9 H 19 —O—(CH 2 CH 2 O) 9.5 H
- R is from coco fatty acid.
- R is from coco fatty acid.
- Frigate is a based adjuvant tallow amine ethoxylate.
- R is a coco Fatty acid
- MON-0139 is an aqueous concentrate comprising the isopropylamine salt of N-phosphonomethylglycine and water, about 62% isopropylamine salt by weight.
- MON-0818 is an ethoxylated tallow amine useful as a surfactant.
- Triton X-45 C 8 H 17 —O—(CH 2 CH 2 O) 5 H
- Igepal CA-630 C 8 H 17 —O—(CH 2 CH 2 O) 9 H
- Glycerin concentration is expressed as % of the total spray volume based on a spray gallonage equivalent to 20 galons/A.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR898906978A BR8906978A (pt) | 1988-06-14 | 1989-06-13 | Formulacoes herbicidas aperfeicoadas e seu uso |
KR1019900700292A KR920002217B1 (ko) | 1988-06-14 | 1989-06-13 | 개선된 제초제와 그 이용 |
NO90900703A NO900703L (no) | 1988-06-14 | 1990-02-13 | Forbedrede herbicide preparater og deres anvendelse. |
FI900696A FI900696A0 (fi) | 1988-06-14 | 1990-02-13 | Foerbaettrade herbicidkompositioner och anvaendning daerav. |
DK037690A DK37690A (da) | 1988-06-14 | 1990-02-13 | Herbicider med forbedret effektivitet og anvendelse af saadanne herbicider |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20640588A | 1988-06-14 | 1988-06-14 | |
US206,405 | 1988-06-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1989012394A1 true WO1989012394A1 (fr) | 1989-12-28 |
Family
ID=22766221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1989/002570 WO1989012394A1 (fr) | 1988-06-14 | 1989-06-13 | Formulations ameliorees d'herbicides et leur emploi |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0407473A1 (fr) |
JP (1) | JPH02504644A (fr) |
KR (1) | KR920002217B1 (fr) |
CN (1) | CN1052409A (fr) |
AU (1) | AU609628B2 (fr) |
BR (1) | BR8906978A (fr) |
DK (1) | DK37690A (fr) |
FI (1) | FI900696A0 (fr) |
HU (1) | HUT55189A (fr) |
WO (1) | WO1989012394A1 (fr) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0355650A2 (fr) * | 1988-08-15 | 1990-02-28 | Dow Corning Corporation | Compositions herbicides de post-lévée contenant des glycols de silicone comme adjuvants |
EP0429293A1 (fr) * | 1989-11-21 | 1991-05-29 | Dow Corning Corporation | Compositions herbicides de post-levée contenant du silicone glycol avec de l'acétoxy terminal et dispersant |
EP0448538A1 (fr) * | 1990-03-15 | 1991-09-25 | Monsanto Company | Formulation de glyphosate |
US5104647A (en) * | 1990-06-22 | 1992-04-14 | Union Carbide Chemicals & Plastics Technology Corporation | Surfactant blend of organosilicone and polyalkylene oxide polymers useful as an agricultural adjuvant |
EP0483095A2 (fr) * | 1990-10-04 | 1992-04-29 | Monsanto Company | Formulations améliorées |
EP0503869A1 (fr) * | 1991-03-11 | 1992-09-16 | Rohm And Haas Company | Formulations d'oxyfluorfen granulaires dispersibles |
EP0526444A1 (fr) * | 1991-08-02 | 1993-02-03 | Monsanto Company | Compositions herbicides |
EP0535596A1 (fr) * | 1991-09-30 | 1993-04-07 | Dow Corning Corporation | Composition herbicide contenant un adjuvant de silicone |
WO1994002021A1 (fr) * | 1992-07-16 | 1994-02-03 | Monsanto Company | Compositions herbicides |
EP0642304A1 (fr) * | 1993-03-30 | 1995-03-15 | OSi Specialties, Inc. | Tensioactif peu moussant et s'etalant d'une maniere exceptionnelle pour des melanges a pulveriser phytosanitaires |
WO1998035561A1 (fr) * | 1997-02-14 | 1998-08-20 | Monsanto Company | Composition aqueuse d'herbicides et de tensio-actifs d'elimination des broussailles s'appliquant a la base et aux parties dormantes de la tige |
EP0862857A1 (fr) * | 1997-03-06 | 1998-09-09 | OSi Specialties, Inc. | Mélanges non ioniques contenant des siloxanes utilisables pour l'agriculture |
US6051730A (en) * | 1997-05-05 | 2000-04-18 | Rhodia Inc. | Surfactant clathrates and agricultural chemical formulations thereof |
US6060522A (en) * | 1997-08-14 | 2000-05-09 | Rhodia Inc. | Surfactant co-clathrates |
EP1053678A1 (fr) * | 1999-05-19 | 2000-11-22 | Shin-Etsu Chemical Co., Ltd. | Composition agrochimique à base d'eau contenant une silicone modifiée par un polyéther |
US6197876B1 (en) | 1999-02-24 | 2001-03-06 | Ck Witco Corporation | Heterocyclic amine modified siloxanes |
US6235681B1 (en) | 1998-12-10 | 2001-05-22 | Ck Witco Corporation | Terminally modified, amino, polyether siloxanes |
WO2002007515A1 (fr) * | 2000-07-25 | 2002-01-31 | Bayer Cropscience Gmbh | Agent herbicide |
WO2002007519A1 (fr) * | 2000-07-25 | 2002-01-31 | Bayer Cropscience Gmbh | Herbicide |
EP1314356A1 (fr) * | 2001-11-21 | 2003-05-28 | Goldschmidt AG | Utilisation dans des compositions agrochimiques de tensioactifs ne s'étalant pas |
EP2207417A2 (fr) * | 2007-10-30 | 2010-07-21 | Basf Se | Utilisation de glycerol, procede de traitement des recoltes, composition destinee au melange en reservoir et procede de preparation d'une composition destinee au melange en reservoir |
EP0494386B2 (fr) † | 1991-01-08 | 2010-08-11 | Mycogen Corporation | Nouveau procédé et composition pour contrôler les mauvaises herbes |
FR3055330A1 (fr) * | 2016-08-30 | 2018-03-02 | Oleon Nv | Composition dissolvante stable a froid |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5912209A (en) * | 1993-12-17 | 1999-06-15 | Monsanto Company | Surfactants providing enhanced efficacy and/or rainfastness to glyphosate formulations |
US5663117A (en) * | 1993-12-17 | 1997-09-02 | Monsanto Company | Alkoxylated primary alcohol surfactants providing enhanced efficacy and/or rainfastness to glyphosate formulations |
US5821195A (en) * | 1996-08-16 | 1998-10-13 | Monsanto Company | Sequential application method for enhancing glyphosate herbicidal effectiveness with reduced antagonism |
JP4191250B2 (ja) * | 1996-08-16 | 2008-12-03 | モンサント・テクノロジー・エルエルシー | 外因性化学物質で植物を処置するための順次適用方法 |
JP2000017177A (ja) | 1998-06-30 | 2000-01-18 | Dow Corning Toray Silicone Co Ltd | 保存安定性に優れたオルガノポリシロキサン組成物 |
UA72761C2 (en) | 1999-04-23 | 2005-04-15 | Monsanto Technology Llc | Compositions and method of eliminating plant growth or controlling thereof |
JP5753405B2 (ja) * | 2010-03-03 | 2015-07-22 | 石原産業株式会社 | 芝草に対する望ましくない作用を軽減する方法 |
KR101476643B1 (ko) * | 2013-06-25 | 2014-12-29 | 최형석 | 잔디 생육을 위한 경엽잡초 방제방법 |
US10188102B2 (en) * | 2015-07-15 | 2019-01-29 | Momentive Performance Materials Inc. | Low foam surfactant composition and methods of making the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1950380A1 (de) * | 1968-10-11 | 1970-04-23 | Dow Corning | Verwendung von oberflaechenaktiven Mitteln zur Wirkungssteigerung von Herbiciden |
FR2589328A1 (fr) * | 1985-10-31 | 1987-05-07 | Stauffer Chemical Co | Methode et composition d'amelioration de l'activite herbicide de sels de n-phosphomethylglycine |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1225249A (fr) * | 1967-09-08 | 1971-03-17 |
-
1989
- 1989-06-13 EP EP89907578A patent/EP0407473A1/fr not_active Withdrawn
- 1989-06-13 BR BR898906978A patent/BR8906978A/pt unknown
- 1989-06-13 HU HU893779A patent/HUT55189A/hu unknown
- 1989-06-13 AU AU38389/89A patent/AU609628B2/en not_active Ceased
- 1989-06-13 KR KR1019900700292A patent/KR920002217B1/ko active IP Right Grant
- 1989-06-13 WO PCT/US1989/002570 patent/WO1989012394A1/fr not_active Application Discontinuation
- 1989-06-13 JP JP1507137A patent/JPH02504644A/ja active Pending
- 1989-12-12 CN CN89109825A patent/CN1052409A/zh active Pending
-
1990
- 1990-02-13 FI FI900696A patent/FI900696A0/fi not_active Application Discontinuation
- 1990-02-13 DK DK037690A patent/DK37690A/da not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1950380A1 (de) * | 1968-10-11 | 1970-04-23 | Dow Corning | Verwendung von oberflaechenaktiven Mitteln zur Wirkungssteigerung von Herbiciden |
FR2589328A1 (fr) * | 1985-10-31 | 1987-05-07 | Stauffer Chemical Co | Methode et composition d'amelioration de l'activite herbicide de sels de n-phosphomethylglycine |
Cited By (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0355650A3 (fr) * | 1988-08-15 | 1991-06-26 | Dow Corning Corporation | Compositions herbicides de post-lévée contenant des glycols de silicone comme adjuvants |
EP0355650A2 (fr) * | 1988-08-15 | 1990-02-28 | Dow Corning Corporation | Compositions herbicides de post-lévée contenant des glycols de silicone comme adjuvants |
EP0429293A1 (fr) * | 1989-11-21 | 1991-05-29 | Dow Corning Corporation | Compositions herbicides de post-levée contenant du silicone glycol avec de l'acétoxy terminal et dispersant |
EP0448538A1 (fr) * | 1990-03-15 | 1991-09-25 | Monsanto Company | Formulation de glyphosate |
US5104647A (en) * | 1990-06-22 | 1992-04-14 | Union Carbide Chemicals & Plastics Technology Corporation | Surfactant blend of organosilicone and polyalkylene oxide polymers useful as an agricultural adjuvant |
EP0483095A2 (fr) * | 1990-10-04 | 1992-04-29 | Monsanto Company | Formulations améliorées |
EP0483095A3 (fr) * | 1990-10-04 | 1992-05-13 | Monsanto Company | Formulations améliorées |
EP0494386B2 (fr) † | 1991-01-08 | 2010-08-11 | Mycogen Corporation | Nouveau procédé et composition pour contrôler les mauvaises herbes |
EP0503869A1 (fr) * | 1991-03-11 | 1992-09-16 | Rohm And Haas Company | Formulations d'oxyfluorfen granulaires dispersibles |
EP0526444A1 (fr) * | 1991-08-02 | 1993-02-03 | Monsanto Company | Compositions herbicides |
EP0535596A1 (fr) * | 1991-09-30 | 1993-04-07 | Dow Corning Corporation | Composition herbicide contenant un adjuvant de silicone |
WO1994002021A1 (fr) * | 1992-07-16 | 1994-02-03 | Monsanto Company | Compositions herbicides |
AU676482B2 (en) * | 1992-07-16 | 1997-03-13 | Monsanto Technology Llc | Herbicidal compositions |
EP0642304A1 (fr) * | 1993-03-30 | 1995-03-15 | OSi Specialties, Inc. | Tensioactif peu moussant et s'etalant d'une maniere exceptionnelle pour des melanges a pulveriser phytosanitaires |
EP0642304A4 (fr) * | 1993-03-30 | 1995-08-16 | Osi Specialties Inc | Tensioactif peu moussant et s'etalant d'une maniere exceptionnelle pour des melanges a pulveriser phytosanitaires. |
WO1998035561A1 (fr) * | 1997-02-14 | 1998-08-20 | Monsanto Company | Composition aqueuse d'herbicides et de tensio-actifs d'elimination des broussailles s'appliquant a la base et aux parties dormantes de la tige |
US6040272A (en) * | 1997-02-14 | 2000-03-21 | Monsanto Company | Aqueous glyphosate/surfactant compositions for basal and dormant stem brush control |
AU738283B2 (en) * | 1997-02-14 | 2001-09-13 | Monsanto Technology Llc | Aqueous herbicide/surfactant compositions for basal or dormant stem brush control |
AU728878B2 (en) * | 1997-03-06 | 2001-01-18 | General Electric Company | Siloxane nonionic blends useful in agriculture |
KR100527208B1 (ko) * | 1997-03-06 | 2006-04-06 | 제너럴 일렉트릭 캄파니 | 농업용실록산비이온계혼합물 |
US6221811B1 (en) | 1997-03-06 | 2001-04-24 | Crompton Corporation | Siloxane nonionic blends useful in agriculture |
EP0862857A1 (fr) * | 1997-03-06 | 1998-09-09 | OSi Specialties, Inc. | Mélanges non ioniques contenant des siloxanes utilisables pour l'agriculture |
US6051730A (en) * | 1997-05-05 | 2000-04-18 | Rhodia Inc. | Surfactant clathrates and agricultural chemical formulations thereof |
US6060522A (en) * | 1997-08-14 | 2000-05-09 | Rhodia Inc. | Surfactant co-clathrates |
US6235681B1 (en) | 1998-12-10 | 2001-05-22 | Ck Witco Corporation | Terminally modified, amino, polyether siloxanes |
US6238684B1 (en) | 1998-12-10 | 2001-05-29 | Osi Specialties, Inc. | Terminally modified, amino, polyether siloxanes |
US6197876B1 (en) | 1999-02-24 | 2001-03-06 | Ck Witco Corporation | Heterocyclic amine modified siloxanes |
EP1053678A1 (fr) * | 1999-05-19 | 2000-11-22 | Shin-Etsu Chemical Co., Ltd. | Composition agrochimique à base d'eau contenant une silicone modifiée par un polyéther |
US6300283B1 (en) | 1999-05-19 | 2001-10-09 | Shin-Etsu Chemical Co., Ltd. | Water-base agrochemical composition containing polyether-modified silicone |
WO2002007519A1 (fr) * | 2000-07-25 | 2002-01-31 | Bayer Cropscience Gmbh | Herbicide |
DE10036003A1 (de) * | 2000-07-25 | 2002-02-14 | Aventis Cropscience Gmbh | Herbizide Mittel |
DE10036002A1 (de) * | 2000-07-25 | 2002-02-14 | Aventis Cropscience Gmbh | Herbizide Mittel |
WO2002007515A1 (fr) * | 2000-07-25 | 2002-01-31 | Bayer Cropscience Gmbh | Agent herbicide |
HRP20030040B1 (en) * | 2000-07-25 | 2011-06-30 | Bayer Cropscience Ag | Herbicide agent |
US6770594B2 (en) | 2000-07-25 | 2004-08-03 | Aventis Cropscience | Herbicidal compositions |
EP1600056A1 (fr) * | 2000-07-25 | 2005-11-30 | Bayer CropScience GmbH | Composition herbicide |
EP1314356A1 (fr) * | 2001-11-21 | 2003-05-28 | Goldschmidt AG | Utilisation dans des compositions agrochimiques de tensioactifs ne s'étalant pas |
AU2002301504B2 (en) * | 2001-11-21 | 2007-07-12 | Evonik Operations Gmbh | Use of Non-spreading Silicone Surfactants in Agrochemical Compositions |
US6734141B2 (en) | 2001-11-21 | 2004-05-11 | Goldschmidt Ag | Use of non-spreading silicone surfactants in agrochemical compositions |
AU2002301504B8 (en) * | 2001-11-21 | 2003-06-12 | Evonik Operations Gmbh | Use of Non-spreading Silicone Surfactants in Agrochemical Compositions |
EP2207417A2 (fr) * | 2007-10-30 | 2010-07-21 | Basf Se | Utilisation de glycerol, procede de traitement des recoltes, composition destinee au melange en reservoir et procede de preparation d'une composition destinee au melange en reservoir |
FR3055330A1 (fr) * | 2016-08-30 | 2018-03-02 | Oleon Nv | Composition dissolvante stable a froid |
WO2018041886A1 (fr) * | 2016-08-30 | 2018-03-08 | Oleon Nv | Composition dissolvante stable à froid. |
Also Published As
Publication number | Publication date |
---|---|
AU609628B2 (en) | 1991-05-02 |
KR920002217B1 (ko) | 1992-03-20 |
HUT55189A (en) | 1991-05-28 |
BR8906978A (pt) | 1990-12-18 |
JPH02504644A (ja) | 1990-12-27 |
HU893779D0 (en) | 1991-04-29 |
CN1052409A (zh) | 1991-06-26 |
DK37690D0 (da) | 1990-02-13 |
KR900701157A (ko) | 1990-12-01 |
FI900696A0 (fi) | 1990-02-13 |
AU3838989A (en) | 1990-01-12 |
DK37690A (da) | 1990-04-09 |
EP0407473A1 (fr) | 1991-01-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU609628B2 (en) | Improved herbicide formulations container silicone surfactant and their uses | |
EP0734206B1 (fr) | Tensioactifs conferant, a des formulations de pesticides, une meilleure efficacite et/ou une meilleure resistance a l'entrainement par la pluie | |
US5912209A (en) | Surfactants providing enhanced efficacy and/or rainfastness to glyphosate formulations | |
US5985793A (en) | Sequential application method for treating plants with exogenous chemicals | |
EP0820231B1 (fr) | Formulations a base de glyphosate, contenant des tensioactifs a base d'etheramine | |
AU2008363855B2 (en) | A liquid, homogenous herbicide composition, a method of weed control, a method of production of liquid, homogenous herbicide composition and use of a liquid, homogenous herbicide composition for weed control | |
AU696607B2 (en) | Surfactants providing enhanced efficacy and/or rainfastness to pesticide formulations | |
US4933002A (en) | Postemergent herbicide compositions containing acetoxy-terminated silicone glycol and dispersant | |
US5663117A (en) | Alkoxylated primary alcohol surfactants providing enhanced efficacy and/or rainfastness to glyphosate formulations | |
US4990175A (en) | Foliar applied herbicidal compositions containing a silicone glycolsilicone alkane terpolymer adjuvant | |
CN112841201A (zh) | 包含嘧啶羧酸苄酯类化合物和ppo抑制剂的除草组合物及其应用 | |
EP0355650B1 (fr) | Compositions herbicides de post-lévée contenant des glycols de silicone comme adjuvants | |
US5059704A (en) | Foliar-applied herbicidal compositions containing a silicone glycol-silicone alkane terpolymer adjuvant | |
US5017216A (en) | Postemergent herbicide compositions containing silicone glycol adjuvants | |
IE893949A1 (en) | Improved herbicide formulations and their use | |
CA2460946C (fr) | Composes, compositions et methodes d'utilisation pour des sels de glyphosate d'ether amines | |
CN115735919B (zh) | 一种含环己烷-1,3-二酮衍生物的除草剂组合物及其应用 | |
CA2067893A1 (fr) | Compositions herbicides a phytotoxicite reduite | |
AU635875B2 (en) | A silicone glycol-silicone alkane terpolymer adjuvant for herbicidal compositions | |
CA2318657E (fr) | Formulations a base de glyphosate, contenant des tensioactifs a base d'etheramine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU BB BG BR DK FI HU JP KR LK MC MG MW NO RO SD SU US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE BF BJ CF CG CH CM DE FR GA GB IT LU ML MR NL SE SN TD TG |
|
WWE | Wipo information: entry into national phase |
Ref document number: 900696 Country of ref document: FI |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1989907578 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1989907578 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1989907578 Country of ref document: EP |