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WO1997041730A1 - Concentres herbicides de type nouveau - Google Patents

Concentres herbicides de type nouveau Download PDF

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Publication number
WO1997041730A1
WO1997041730A1 PCT/US1997/007621 US9707621W WO9741730A1 WO 1997041730 A1 WO1997041730 A1 WO 1997041730A1 US 9707621 W US9707621 W US 9707621W WO 9741730 A1 WO9741730 A1 WO 9741730A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
composition
compound
glyphosate
surfactant
Prior art date
Application number
PCT/US1997/007621
Other languages
English (en)
Inventor
John Harvey
Paul S. Zorner
Original Assignee
Mycogen Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mycogen Corporation filed Critical Mycogen Corporation
Priority to AU29970/97A priority Critical patent/AU2997097A/en
Publication of WO1997041730A1 publication Critical patent/WO1997041730A1/fr

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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
    • 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

  • the losses caused by weeds in agricultural production environments include decrease in crop yield, reduced crop quality, increased irrigation costs, increased harvesting costs, decreased land value, injury to livestock, and crop damage from insects and diseases harbored by the weeds.
  • Chemical herbicides have provided an effective method of weed control; however, the public has become concerned about the amount of residual chemicals which might be found in food, ground water, and the environment Stringent new restrictions on the use of herbicides and the elimination of some effective herbicides from the market place could limit economical and effective options for controlling costly weeds. Additionally, the visually apparent phytotoxic effects of some systemic herbicides appear very slowly on the target weeds, so pesticide users often seek methods by which the apparent speed of action of the herbicide is increased. Recently, fatty acids and salts of fatty acids have been used commercially as pesticides and herbicides. Compositions having excellent pesticidal properties which exploit fatty acid salts are available commercially under the trademark SAFER INSECTICIDAL SOAP. A herbicidally-active composition utilizing partially saponified fatty acids as the active ingredient is sold under the trademark SHARPSHOOTER. These fatty acid compositions have no known long-term environmental effects.
  • U.S. Patent No. 5,196,044 concerns novel compositions and methods for selective or non-selective control of plants More specifically, that patent pertains to the application to weeds of a combination of certain chemical herbicides and one or more fatty acids, or their salts, which results in the effective control of a broad range of plants
  • U.S. Patent Nos. 2,626,862; 4,975,110; and 5,035,741 describe certain fatty acid compositions useful as herbicides. These documents mention the use of salts of fatty acids. Specifically, "saponified" fatty acids are discussed.
  • Saponif ⁇ cation means "to form the sodium or potassium salt of a fatty acid.” It stems from the soap making industry where animal fats (esters of fatty acids and glycerol) are hydrolyzed in sodium or potassium hydroxide to form the sodium or potassium salts of the fatty acids (soaps) and free glycerol Mixing sodium or potassium hydroxide with a free fatty acid to form the salt is also called saponif ⁇ cation "Complete” saponification means that 100% of the fatty acid is converted to the salt; “partial” sapomfication means that ⁇ 100% of the acid is converted to the salt. This means there is a mixture of the free fatty acid and the fatty acid salt.
  • U.S. Patent No. 4,975,110 indicates that the free fatty acid form is preferable to fatty acid salts for use as a herbicide. These patents also teach that the proper formulation of a fatty acid herbicide requires one or more surfactants.
  • Herbicidally-active fatty acid esters are desc ⁇ bed m U.S. Patent No. 5,284,819, which is incorporated herein by reference.
  • PCT application No. WO93/09669 discloses fatty acid amine salts with herbicidal activity.
  • novel weed control methods which reduce the amount of chemical herbicide necessary to obtain acceptable levels of weed control.
  • Especially advantageous would be herbicidally-active emulsifiable concentrates, rather than "ready to use” mixtures.
  • Practitioners in the herbicide art often expe ⁇ ence difficulty in formulating or obtaining mixtures of herbicides.
  • the subject invention provides novel herbicidally-active concentrates and methods of formulating the same.
  • the compositions of the subject invention are highly advantageous because they provide thermostable concentrated solutions of immiscible components.
  • the concentrates of the subject invention comprise a glyphosate compound and a fatty acid compound.
  • the fatty acid compound may be in the acid form or a lipophilic fatty acid derivative.
  • Such derivatives include esters and amine salts.
  • the glyphosate compound is the isopropylamine salt, and the fatty acid compound is an ester.
  • the fatty acid ester component is an ethylene glycol pelargonate.
  • the herbicidal concentrates of the subject invention comprise, in addition to the glyphosate compound and the fatty acid compound, a suitable surfactant and solvent.
  • the fatty acid component is preferably an ester, mixtures of fatty acid compounds may be used according to the subject invention.
  • the fatty acid compound of the subject invention can be represented by the following formula: o
  • R C5 to C12 saturated or unsaturated hydrocarbon, or an epoxide, or cyclopropane thereof
  • Y H, C1-C5 hydrocarbon, or hydroxyl at any position along R
  • Y 2 H, C1-C5 hydrocarbon, or hydroxyl at any position along R
  • R 2 H; Cl to CIO saturated or unsaturated hydrocarbon; or a salt-forming moiety chosen from the group consisting of aliphatic amines which form cationic aliphatic ammonium compounds
  • X, H, hydroxyl, or Cl to C3 hydrocarbon at any position along R 2
  • X 2 H, hydroxyl, or Cl to C3 hydrocarbon at any position along R 2 .
  • Z is N, then of course there would be two R 2 groups. If R 2 is H, then of course there would be no X, or X 2 .
  • R 2 is the mono- glycol ester of pelargonic (C9) acid.
  • Advantages provided by concentrates of the subject invention include reduced packaging costs and increased stability, longer shelf life, and ease of storage. The concentrates are easy to dilute for use at a desired concentration. Thus, an additional advantage of the concentrates desc ⁇ bed herein is the reduction m the time and effort needed to formulate the desired end product.
  • the subject invention concerns herbicidally-active concentrates.
  • the concentrates of the subject invention comp ⁇ se a two component active ingredient system
  • the first active component compnses a glyphosate compound.
  • the second active component compnses a fatty acid compound.
  • the fatty acid compound is lipophilic and may be the free fatty acid or, preferably, an ester or aliphatic amine salt.
  • the subject invention provides a concentrated, thermodynamically stable solution compnsing two normally immiscible components, the water-insoluble fatty acid component and a highly polar solution of a glyphosate salt.
  • a normally incompatible system such as desc ⁇ bed herein may be prepared according to the subject invention as a stable microemulsion.
  • the concentrate may have, for example, from about 1 to about 5 lbs. of active ingredient per gallon.
  • the concentrations of active ingredients are expressed as acid equivalents of each component.
  • the glyphosate compound is present as the isopropyl amine salt.
  • Other glyphosate compounds can be used according to the subject invention. The skilled artisan will appreciate that glyphosate can be any one of a number of salts of the acid compound
  • the fatty acid compound used according to the subject invention can be unsubstituted, or substituted, saturated, or unsaturated, lipophilic fatty acid compounds of about C6 to about C 13.
  • fatty acids of length C9 to C 12 as typified by, but not limited to, decanoic and pelargonic acids
  • the fatty acid compound is the ethylene glycol pelargonate ester.
  • the fatty acid component of the subject invention may be a single fatty acid compound or a mixture of two or more fatty acid compounds.
  • the fatty acid carbon chain is saturated
  • ethylene glycol pelargonate is available from Henkel (product no.
  • lipophilic fatty acid compounds refers to fatty acids and their derivatives which have a solubility in water which is similar to the solubility of the compounds specifically exemplified herein.
  • Aliphatic amme salts of fatty acid which can be used according to the subject invention are those which form lipophilic compounds.
  • R 2 can be an aliphatic amine or other compound which would form a lipophilic fatty acid compound
  • Aliphatic amines which may be used to form the fatty acid compound useful according to the subject invention can be selected from the group including, but not limited to, tryptamine, n-amylamine, ethanolamine, n-hexylamine, sec- butylamine, or isopropylamine. A preferred example is isopropylamine.
  • organic amines can be used according to the subject invention so long as these other bases have comparable attributes of base strength and pola ⁇ ty.
  • the compounds which can be used according to the subject invention include, but are not limited to, the alkyl amines, alkylene amines and alkanol amines containing not more than 2 amme groups, such as methylamme, ethylamine, n-propylamine, isopropylamine, «-butylamme, isobutylamine, .seobutylamine, n-amylamme, isoamylamine, hexylamine, heptylamme, octylamine, nonylamine, decylamme, undecylamme, dodecylamme, tridecylamme, tetradecyclamine, pentadecylamine, hexadecylamme, hepta
  • the compounds formed according to the subject mvention can be, for example, from the group consisting of monoalkylammonium, dialkylammonium, t ⁇ alkylammonium, monoalkenylammomum, dialkenylammomum, tnalkenylammomum, monoaklynylammonium, dialkynylammomum, tnalkynylammonium, monoalkanolammonium, dialkanolammomum, and t ⁇ alkanolammomum.
  • the two-component active ingredient composition of the subject invention can be prepared by combining glyphosate and a fatty acid compound together with a non-ionic, anionic, or cationic surfactant.
  • glyphosate or a “glyphosate compound” includes the va ⁇ ous herbicidal forms of this product.
  • Aqueous formulations of glyphosate can contain one or more salts, such as an alkylamine, for example, isopropylammonium salt, the ammonium salt, the trimethylsulfonium salt, or an alkali metal, for example potassium or sodium, salt of glyphosate. Additional salts are described in U.S. Patent No 4,405,531, which is incorporated herein by reference.
  • the fatty acid component may be an acid, ester, or a lipophilic amme salt to which the glyphosate component may be added.
  • Conversion to a microemulsion can then be made by the addition of a surfactant, typically an alkyl or aryl ethoxylate dissolved in a co-solvent.
  • a surfactant typically an alkyl or aryl ethoxylate dissolved in a co-solvent.
  • Other surfactants having similar surface active properties may be used in the practice of the subject invention.
  • use of a surfactant together with a co-solvent facilitates phase changes resulting in a microemulsion.
  • the microemulsion will preferably comp ⁇ se micelles of approximately lOOOA or smaller. If a co-solvent is used, it can be, for example, an alcohol having from about 1 to about 8 carbons.
  • Suitable alcohols include methyl, propyl, and octyl alcohols.
  • Water can be provided for the microemulsion by the glyphosate solution. If an ethoxylated surfactant is used, the degree of ethoxylation of the surfactant can be vaned by one skilled in the art in accordance with the teachings provided herein. One could choose, for example, a surfactant having from about 5 moles to about 15 moles or more of ethoxylation.
  • Various concentrations of the components of the subject emulsifiable herbicide concentrates can be used according to the subject invention.
  • approximately 0.05 to 2.0 lbs. of the glyphosate component can be used per gallon of concentrate.
  • about 0.25 to about 1.5 lbs., and more preferably about 1.0 lb. of the glyphosate component will be used per gallon of concentrate.
  • Approximately 0.5 to 6.0 lbs. of fatty acid ester can be used per gallon of concentrate.
  • about 1 lb. to about 5 lbs., and more preferably about 4 lbs , of the fatty acid ester will be used per gallon of concentrate.
  • surfactant per gallon of concentrate can be added to emulsify the active components
  • about 0.5 to about 1.5 lbs., and more preferably about 1.0 lb. of surfactant will be used per gallon of concentrate.
  • 0 to 2.5 lbs. of a co- solvent can be added per gallon of the final concentrate volume.
  • about 1 to about 2 lbs. of co-solvent, and more preferably about 1.5 lbs. of co-solvent will be used per gallon of concentrate.
  • the active ingredients of the concentrates of the subject invention will typically comprise about 12% to about 85% of the concentrates.
  • the fatty acid compound itself can comp ⁇ se up to about 80% of the final composition.
  • the surfactant will typically be present in the amount of about 2% to about 20% of the final mixture.
  • the co-solvent will typically range from about 0% to about 30% of the final composition.
  • the remainder of the subject emulsifiable concentrates can be comprised of water as the base solvent. Other polar base solvents can be used.
  • the ratio of fatty acid compound to glyphosate compound can range from about 1 • 1 to about 50:1
  • va ⁇ ous amounts of the ingredients of the subject compositions can be combined in the successful practice of the subject invention following are examples of possible combinations of the components of the subject compositions: 0 5 1b of the glyphosate component, 0.5 lb of the fatty acid component, and 0.25 lbs of the surfactant solution can be combined, with the water being cont ⁇ ubbed by the glyphosate, to form one gallon of an embodiment of the subject composition As another example, 0.33 lbs. of the glyphosate component, 4.16 lbs.
  • lb. of the glyphosate component, 1 lb. of the fatty acid component, and 1 lb. of the surfactant can be combined, and 1 lb. of the co-solvent can be added, with water as the base solvent, to form one gallon of an embodiment of the subject composition.
  • 1.5 lbs. of the glyphosate component, 1.5 lbs. of the fatty acid component, and I 5 lbs. of the surfactant can be combined, and 1.5 lbs.
  • the co-solvent can be added, with water as the base solvent, to form one gallon of an embodiment of the subject composition.
  • Yet another example would be to combine 1.5 lbs of the glyphosate component, 3 lbs. of the fatty acid component, with 1 lb. of the surfactant, and 2 lbs. of the co-solvent can be added, with additional water as would be needed, depending on the concentrations of the available component sources, to form one gallon of an embodiment of the subject composition.
  • Decanoic acid (C )0 acid), dodecanoic acid (C 12 acid), and tetradecanoic acid (C, 4 acid) each of 100 mmol of C 10 , C 12 and C, 4 acids were dissolved in 50 ml dichloromethane, and 300 mmol of ethylene glycol was added to the solutions. Several drops of H 2 S0 4 were added to the mixture. The reaction mixtures were stored at room temperature for 9 days. Isolation of the esters were earned out using the same procedure as that to isolate ethylene glycol monopelargonate. Distillations were not undertaken.
  • Two to three pounds of a glyphosate compound can be combined by moderate mixing with five to six pounds of a fatty acid compound and three to five pounds of a co-solvent solution of a nonionic surfactant.
  • the ratio of co-solvent to surfactant can be va ⁇ ed depending on, for example, the number of moles of ethoxylation of the surfactant.
  • the co- solvent to surfactant ratio can vary from about 1: 1 to about 10.1.
  • Ratios of fatty acid to glyphosate used to prepare the stable concentrates of the subject invention can range from about 1 : 1 to about 50: 1.
  • the resulting microemulsion can be emulsified with water, which results in a typical colloidal emulsion.
  • concentrates can readily be produced that contain between about 1 and about 5 lbs. total active ingredient/gallon of concentrate.
  • the concentrates prepared as descnbed herein can be diluted to a desired concentration by adding water or other appropnate solvent to the concentrates.
  • the composition resulting from the dilution of the concentrate is suitable for application to plants, or the site of plants, via any number of techniques that are known in the art. Suitable application techniques include backpack spraying It should be understood that the examples and embodiments descnbed herein are for illustrative purposes only and that va ⁇ ous modifications or changes in light thereof will be suggested to persons skilled in the art and are to be included within the spint and purview of this application and the scope of the appended claims

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention se rapporte à des concentrés herbicides de type nouveau et à des méthodes de formulation et d'utilisation de ces concentrés. Les concentrés décrits dans la présente invention comprennent un composé à base de glyphosate et un composé choisi parmi les acides gras, ainsi qu'un tensioactif approprié et des solvants.
PCT/US1997/007621 1996-05-08 1997-05-07 Concentres herbicides de type nouveau WO1997041730A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29970/97A AU2997097A (en) 1996-05-08 1997-05-07 Novel herbicidally-active concentrates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64344096A 1996-05-08 1996-05-08
US08/643,440 1996-05-08

Publications (1)

Publication Number Publication Date
WO1997041730A1 true WO1997041730A1 (fr) 1997-11-13

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PCT/US1997/007621 WO1997041730A1 (fr) 1996-05-08 1997-05-07 Concentres herbicides de type nouveau

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AU (1) AU2997097A (fr)
WO (1) WO1997041730A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6184182B1 (en) 1996-10-25 2001-02-06 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6689719B2 (en) 1999-08-11 2004-02-10 Monsanto Technology Llc Coformulation of carfentrazone-ethyl and glyphasate
US6713433B2 (en) 1999-08-11 2004-03-30 Monsanto Technology, Llc Coformulation of an oil-soluble herbicide and a water-soluble herbicide
US8268749B2 (en) 2004-09-17 2012-09-18 Monsanto Technology Llc Fast symptom glyphosate formulations

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992007467A1 (fr) * 1990-11-02 1992-05-14 Safer, Inc. Composition herbicide amelioree a base d'acide gras
EP0494386A1 (fr) * 1991-01-08 1992-07-15 Mycogen Corporation Nouveau procédé et composition pour contrôler les mauvaises herbes
WO1992011764A1 (fr) * 1991-01-08 1992-07-23 Monsanto Company Formulation herbicide amelioree
US5199044A (en) * 1990-05-22 1993-03-30 Tokimec Inc. System for detecting position of object having data carrier
JPH05271007A (ja) * 1992-03-30 1993-10-19 Dainippon Ink & Chem Inc 除草方法
WO1993021768A1 (fr) * 1992-05-01 1993-11-11 Mycogen Corporation Nouveaux esters d'acides gras a action herbicide
EP0577914A1 (fr) * 1992-07-08 1994-01-12 Monsanto Europe S.A./N.V. Compositions améliorées de glyphosate et leur utilisation
WO1994013140A1 (fr) * 1992-12-14 1994-06-23 Buckman Laboratories International, Inc. Composition et procede augmentant l'efficacite des pesticides

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5199044A (en) * 1990-05-22 1993-03-30 Tokimec Inc. System for detecting position of object having data carrier
WO1992007467A1 (fr) * 1990-11-02 1992-05-14 Safer, Inc. Composition herbicide amelioree a base d'acide gras
EP0494386A1 (fr) * 1991-01-08 1992-07-15 Mycogen Corporation Nouveau procédé et composition pour contrôler les mauvaises herbes
WO1992011764A1 (fr) * 1991-01-08 1992-07-23 Monsanto Company Formulation herbicide amelioree
JPH05271007A (ja) * 1992-03-30 1993-10-19 Dainippon Ink & Chem Inc 除草方法
WO1993021768A1 (fr) * 1992-05-01 1993-11-11 Mycogen Corporation Nouveaux esters d'acides gras a action herbicide
EP0577914A1 (fr) * 1992-07-08 1994-01-12 Monsanto Europe S.A./N.V. Compositions améliorées de glyphosate et leur utilisation
WO1994013140A1 (fr) * 1992-12-14 1994-06-23 Buckman Laboratories International, Inc. Composition et procede augmentant l'efficacite des pesticides

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ARNOLD ET AL.: "Improved early symptom development with a ready-to-use Glyphosate formulation By addition of fatty acid", PESTICIDE SCIENCE, vol. 38, 1993, pages 270 - 271, XP002041039 *
DATABASE WPI Derwent World Patents Index; AN 93-365089, XP002041040, DAINIPPON INK & CHEM KK: "Weed synergistic herbicide compsns. -uses combination of herbicidal stimulant of straight chain fatty acid and e.g. glyphosate" *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6184182B1 (en) 1996-10-25 2001-02-06 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6689719B2 (en) 1999-08-11 2004-02-10 Monsanto Technology Llc Coformulation of carfentrazone-ethyl and glyphasate
US6713433B2 (en) 1999-08-11 2004-03-30 Monsanto Technology, Llc Coformulation of an oil-soluble herbicide and a water-soluble herbicide
US8268749B2 (en) 2004-09-17 2012-09-18 Monsanto Technology Llc Fast symptom glyphosate formulations

Also Published As

Publication number Publication date
AU2997097A (en) 1997-11-26

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