WO1997036494A1 - Composes herbicides et phytoregulateurs de croissance et procede d'utilisation - Google Patents

Composes herbicides et phytoregulateurs de croissance et procede d'utilisation Download PDF

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Publication number
WO1997036494A1
WO1997036494A1 PCT/US1997/005577 US9705577W WO9736494A1 WO 1997036494 A1 WO1997036494 A1 WO 1997036494A1 US 9705577 W US9705577 W US 9705577W WO 9736494 A1 WO9736494 A1 WO 9736494A1
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WIPO (PCT)
Prior art keywords
carbon atoms
alkyl group
ingredient
composition
long chain
Prior art date
Application number
PCT/US1997/005577
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English (en)
Inventor
Ralph W. Magin
Joe D. Sauer
Dru L. Delaet
Original Assignee
Albemarle 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 Albemarle Corporation filed Critical Albemarle Corporation
Publication of WO1997036494A1 publication Critical patent/WO1997036494A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—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 glyphosate formulations which are highly effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal use against undesired vegetation.
  • Glyphosate N-(phosphonomethyl)glycine
  • N-(phosphonomethyl)glycine is a well-known widely used herbicide. It is generally employed in the form of an agriculturally acceptable salt.
  • glyphosate salts such as the amine, sodium, alkylsulfonium, alkylphosphonium, sulfonylamine, and aminoguanidine salts thereof by means of an environmentally friendly aqueous formulation made from as few ingredients as possible, especially if this can be accomplished by use of readily available, cost-effective materials while at the same time avoiding the inclusion of polyvalent metal-containing and metalloid-containing components in the formulation.
  • This invention is deemed to fulfill this need in an effective and highly efficient manner.
  • This invention involves the discovery, inter alia, that certain hydroxyalkyl quaternary ammonium halides are highly effective as adjuvants for increasing the phytotoxic and growth regulant effectiveness of glyphosate against a number of common plant species.
  • this invention makes it possible to achieve enhanced phytotoxic and plant growth regulant effectiveness in an aqueous solution formed from as few as two added ingredients, both of which are readily available in the marketplace. Consequently it is possible pursuant to this invention to employ the glyphosate herbicide in dosage levels lower than currently recommended.
  • the particular hydroxy-substituted quaternary ammonium halide adjuvants used in the practice of this invention are in themselves environmentally friendly.
  • the formulation requires no polyvalent metal or metalloid components in its formation. Indeed the preferred compositions are devoid of metal and metalloid additive content, and most preferably contain only the elements C, H, O, N, P, and Cl or Br, and optionally S.
  • the liquid concentrates are most preferably formed using deionized water.
  • the adjuvants of this invention are water-soluble quaternary ammonium compounds which can be represented by the formula:
  • R ⁇ R ⁇ N ® X ⁇ wherein R 1 is an alkyl group having in the range of 10 to 18 (preferably 10 to 14) carbon atoms, R 2 is a hydroxyalkyl group having from 2 to 4 (preferably 2) carbon atoms, R 3 is a methyl or ethyl group (preferably methyl), R 4 is independently (a) an alkyl group having in the range of 10 to 18 (preferably 10 to 14) carbon atoms, or (b) a hydroxyalkyl group having from 2 to 4 (preferably 2) carbon atoms, or (c) a methyl or ethyl group (preferably methyl), and X is a chlorine or bromine atom (preferably a bromine atom).
  • this invention provides a method of controlling vegetation by applying to plant foliage, preferably by spraying, a polyvalent metal-free and metalloid-free solution containing an effective herbicidal or plant growth regulant amount of a composition formed by intimately mixing the following ingredients with water:
  • Another embodiment of this invention is a polyvalent metal-free and metalloid- free herbicide or plant growth regulant composition formed by intimately mixing at least a herbicidal or plant growth regulant amount of ingredients (a) and (b) above with water, ingredient (a) being the only herbicide(s) or plant growth regulant(s) and ingredient (b) being the only surfactant(s) used in forming the composition.
  • ingredient (a) being the only herbicide(s) or plant growth regulant(s) and ingredient (b) being the only surfactant(s) used in forming the composition.
  • one or more substances that are not herbicides, or plant growth regulants, or surfactants, such as dyes, humectants, corrosion inhibitors, stickers, spreaders and thickeners, can be included as component (c) in these compositions.
  • Still another embodiment of this invention is a powder or granular herbicide or plant growth regulant formulation which comprises a mixture containing an effective herbicidal or plant growth regulant amount of a composition formed by intimately mixing together components (a) and (b), and optionally including one or more of (c) above.
  • Such compositions can also be formed by evaporating to dryness (e.g., by spray drying, extrusion or pan granulation) a solution of components (a) and (b) above, and optionally
  • the herbicidal (phytotoxic) and the plant growth regulant compositions of this invention include aqueous concentrates which can be shipped and stored until diluted with more water on site to produce the final solution for application to the foliage as by spraying.
  • the herbicidal and the plant growth regulant compositions of this invention include the more dilute aqueous solutions for use in application to the foliage.
  • aqueous solutions are preferably formed simply by suitably diluting an aqueous concentrate of this invention with water (if a powder or granular concentrate) or with more water (if a liquid concentrate) to achieve the appropriate herbicidal or plant regulant dosage, but alternatively, can be formed on site by intimately mixing the separate ingredients or sub-combinations thereof with sufficient water on site to achieve the appropriate dosage.
  • Use of the solid or liquid concentrates of this invention is preferable as it is a much simpler operation and minimizes the possibility of blending errors.
  • other components such as fertilizers, penetrants, spreaders, stickers, etc., can be introduced into the final solution at the time the concentrate is blended with water to form the diluted solution for application to the foliage.
  • Component (a) The identities and methods for the preparation of the glyphosate ingredient of the formulation are well known and are reported in the literature. See for example, U.S. Pat. No. 3,799,758 to J. E. Franz which describes amine salts and alkali metal salts of glyphosate, and the production of glyphosate by such methods as the phosphonomethylation of glycine, the reaction of ethyl glycinate with formaldehyde and diethylphosphite, and the oxidation of the corresponding ammophosphinic compounds.
  • Another method involves conducting a Mannich reaction with phosphorous acid and formaldehyde on iminodiacetic acid followed by controlled oxidation to N-
  • glyphomethyl a compound formed with isopropyl amine.
  • sodium is the preferred cation.
  • alkylsulfonium salts of glyphosate are described for example in U.S. Pat. No. 4,315,765 to G. B. Large, and analogous procedures can be used for producing alkylphosphomum salts.
  • alkylsulfonium and alkylphosphonium salts the trimethylsulfonium salt of glyphosate is preferred.
  • Sulfonylamine and aminoguanidine salts of glyphosate which are also suitable for use pursuant to this invention are disclosed in EP-A-0 088 180.
  • the patent literature contains numerous additional references to various other methods for the production of glyphosate. See for example U.S. Pat. Nos. 4,851,159; 4,898,972; 4,937,376; 4,952,723; 5,061,820; and 5,072,033 to Fields Jr. et al.; 5,023,369 to Fields, Jr.; 4,853,159 to Riley et.
  • One preferred subgroup is composed of the C J0 . 1g (more preferably C 10 . 14 ) monoalkyl methyl diethanol quaternary ammonium chlorides and bromides (more preferably the bromides), especially where the long chain alkyl group is a linear primary alkyl group.
  • the other preferred subgroup is composed of the C i0 _ ls (more preferably C 10-I4 ) monoalkyl dimethyl ethanol quaternary ammonium chlorides and bromides (more preferably the bromides), especially where the long chain alkyl group is a linear primary alkyl group.
  • Tetradecyl methyl diethanol ammonium bromide and tetradecyl dimethyl ethanol ammonium bromide are particularly preferred because of the great effectiveness which they have exhibited in the test work conducted to date.
  • Glyphosate Salt aminoguanidine salt
  • Table 1 The percentages for the amine, alkali metal, alkylsulfonium, alkylphosphomum, sulfonylaniine, and/or aminoguanidine salt (Glyphosate Salt) used in the practice of this invention as given in Table 1 are on an active ingredient basis and are in terms of glyphosate acid equivalent (i.e. , the weight of the particular salt-forming portion of the product is excluded from the weight of the salt). Likewise the amount of any water associated with the salt as received is excluded from consideration as regards the percentages of the Glyphosate Salt shown in the table.
  • Table 2 sets forth the proportions which can be used in forming the powder or granular compositions of this invention. As in Table 1 , the percentages given in Table 2 are weight percentages on an active ingredient basis, and represent weight percent of the total composition. And as above, the percentages for the amine, alkali metal, alkylsulfonium, alkylphosphomum, sulfonylamine, and/or aminoguanidine glyphosate salt ("Glyphosate Salt”) used in the practice of this invention as given in Table 2 are in terms of glyphosate acid equivalent. Table 2
  • the diluted solutions for application to the plant foliage are typically formed prior to application using a tank mixer, spray tank or similar apparatus.
  • the dosage level of the composition applied to the plant foliage will depend to some extent upon the plant species being treated, the extent of control desired, and the prevailing weather conditions. Generally speaking, however, die amount applied will be a herbicidal or growth regulant amount within the range of 50 to 1250 grams of glyphosate (on an acid equivalent basis, i.e. , excluding the weight of the cationic salt associated therewith) per hectare. In terms of ounces avoirdupois per acre this range corresponds (on the same acid equivalent basis) to from 0.7 to 20 ounces of glyphosate per acre).
  • a herbicidal or plant growth regulant amount (again on an acid equivalent basis) falling within the range of 200 to 830 grams of glyphosate per hectare which corresponds (on the same acid equivalent basis) to 3 to 12 ounces avoirdupois of glyphosate per acre), as this is generally sufficient to control most undesired plant species, is below the dosage currently recommended for herbicidal use of glyphosate formulations, and is thus more economical and environmentally friendly.
  • EXAMPLE I A field test was conducted in which the effectiveness of tetradecyl methyl diethanol ammomum bromide (also known as tetradecyl methyl bis(2-hydroxyethyI) ammonium bromide) as a performance enhancer for glyphosate was studied.
  • the test formulation consisted of the aqueous solution made from N-(phosphonomethyl)glycine isopropyl amine salt, water, and the quaternary ammonium compound. No other component or ingredient was employed in forming the test formulation.
  • Agricultural Sprav Adjuvants Used in the United States, by T. L. Harvey, 1992-93 Edition, Thomson Publications, Fresno, California, page 33 is alkyl polyoxyalkane ether, free fatty acids and IPA, which is an adjuvant currently recommended for use in glyphosate formulations.
  • the control formulation was applied at the recommended dosage level of 15 fluid ounces of glyphosate (active ingredient basis) per acre (624 grams of glyphosate per hectare) whereas the formulation of this invention was applied at a dosage of only 10 fluid ounces of glyphosate (active ingredient basis) per acre (416 grams of glyphosate per hectare). Both solutions contained one percent of the particular surfactant used.
  • the weed species populations were wild poinsettia (2-7 inches or 5.1-17.8 centimeters in height with 2-5 leaves per plant), and a combination of Johnson grass and barnyard grass (3-6 inches or 7.6-15.2 centimeters in height with 3-5 leaves per plant).
  • the soil and leaf conditions were both dry at the time of application.
  • one or more other substances can be employed in the formulations of this invention provided no such substance materially detracts from die effectiveness of the composition in combatting the particular plant species to be controlled by use of the formulation.
  • materially in this context is meant that in tests conducted by concurrent application under identical conditions and using identical dosages of one or die omer of two (2) test formulations to a plant species in tfiree (3) identical pairs of test plots (each pair consisting of a Case I plot and a Case II plot) in the same substantially uniform test site, where in Case I the formulation of ti s invention does not contain such additional substance(s) whereas in Case II the identical formulation does additionally contain such additional substance(s), there is a reduction in the average percentages of d e plant species controlled in the three (3) Case JJ plots as compared to the average percentages of die plant species controlled in die three (3) Case I plots, and the aridimetic difference between tiiese averages exceeds 10% .
  • Such other substances tiiat may be used if tiiey do not materially detract from d e effectiveness of me composition include dyes, pigments, humectants, corrosion inhibitors, ti ⁇ ckeners, adhering agents (stickers), spreading agents, and like materials.
  • Such otiier substances can be introduced into die formulation in any sequence relative to components (a) and (b) hereof, i.e., such materials can be added before, after or at die same time as either or bom of components (a) and (b).
  • the one or more glyphosate salts constitute(s) the only herbicide(s) or plant growth regulant(s) used in forming the compositions of this invention.
  • one or more of the herein-described quaternary ammonium compounds constitute(s) the only surfactant(s) used in the practice of this invention. This ensures that the substantial benefits provided by this invention are realized in full.
  • the powder or granular formulations of this invention may be mixed with a finely-divided solid diluent such as talc, gypsum, Fuller's earth, kaolin, kieselguhr, bentonite, dolomite, calcium carbonate, and powdered magnesia. They may also be formulated as dispersible powders or grains, and in this case it is desirable to include a wetting agent to facilitate the dispersion of powder or grains in the liquid carrier. Additionally, formulations in the form of powders can be applied to vegetation as foliar dusts.
  • a finely-divided solid diluent such as talc, gypsum, Fuller's earth, kaolin, kieselguhr, bentonite, dolomite, calcium carbonate, and powdered magnesia. They may also be formulated as dispersible powders or grains, and in this case it is desirable to include a wetting agent to facilitate the dispersion of powder or grains in the
  • the terms "ingredient” or “component” or “substance” as used anywhere in the specification or claims hereof, whether used in the singular or plural, are used in the sense that it is a substance employed in forming the powder or granular concentrate or aqueous solution, and thus at least prior to mixing with other ingredients or components and/or addition to an aqueous medium, the ingredient or component is in the chemical form specified. It matters not what chemical changes, transformations and/or reactions, if any, take place in the mixture or aqueous medium itself as such changes, transformations and/or reactions are the natural result of bringing

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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

La présente invention décrit des formulations de glyphosate agissant efficacement, même aux doses inférieures recommandées pour les herbicides post-émergence et la régulation de croissance des plantes. Lesdites compositions ont été établies selon diverses formulations: solutions aqueuses, poudres ou granulés de (a) un ou plusieurs sels de glyphosate amine, métal alcalin, alkylsulfonium, alkylphosphonium, sulfonylamine et/ou aminoguanidine comme le ou les seuls herbicides entrant dans ladite composition et acceptables dans le domaine agricole; et (b) un ou plusieurs types particuliers de composés ammoniaqués quaternaires comme surfactants entrant dans ladite composition. Lesdits composés ammoniaqués quaternaires sont représentés par la formule: R?1R2R3R4NOXO¿, dans laquelle R1 représente un groupe alkylé possédant une plage atomique de 10 à 18 atomes de carbone, R2 représente un groupe hydroxyalkylé possédant de 2 à 4 atomes de carbone, R3 représente un groupe méthylique ou éthylique, R4 représente, de manière indépendante, (i) un groupe alkylé possédant une plage atomique de 10 à 18 atomes de carbone, ou (ii) un groupe hydroxyalkylé possédant de 2 à 4 atomes de carbone, ou (iii) groupe méthylique ou éthylique, et X représente un atome de chlore ou de brome.
PCT/US1997/005577 1996-04-03 1997-04-03 Composes herbicides et phytoregulateurs de croissance et procede d'utilisation WO1997036494A1 (fr)

Applications Claiming Priority (2)

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US62609896A 1996-04-03 1996-04-03
US08/626,098 1996-04-03

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6130186A (en) * 1996-10-25 2000-10-10 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6746976B1 (en) 1999-09-24 2004-06-08 The Procter & Gamble Company Thin until wet structures for acquiring aqueous fluids
US7049270B2 (en) 2000-05-19 2006-05-23 Monsanto Technology Llc Potassium glyphosate formulations
US7723265B2 (en) 2000-05-19 2010-05-25 Monsanto Technology Pesticide compositions containing oxalic acid
DE102011111152A1 (de) 2011-08-20 2013-02-21 Clariant International Ltd. Pestizidzubereitungen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274369A1 (fr) * 1986-12-04 1988-07-13 Monsanto Company Formulation herbicide glyphosphate-sulfate d'ammonium
EP0483095A2 (fr) * 1990-10-04 1992-04-29 Monsanto Company Formulations améliorées

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274369A1 (fr) * 1986-12-04 1988-07-13 Monsanto Company Formulation herbicide glyphosphate-sulfate d'ammonium
EP0483095A2 (fr) * 1990-10-04 1992-04-29 Monsanto Company Formulations améliorées

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6130186A (en) * 1996-10-25 2000-10-10 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6746976B1 (en) 1999-09-24 2004-06-08 The Procter & Gamble Company Thin until wet structures for acquiring aqueous fluids
US7049270B2 (en) 2000-05-19 2006-05-23 Monsanto Technology Llc Potassium glyphosate formulations
US7723265B2 (en) 2000-05-19 2010-05-25 Monsanto Technology Pesticide compositions containing oxalic acid
US10736325B2 (en) 2000-05-19 2020-08-11 Monsanto Technology Llc Surfactants and formulations
DE102011111152A1 (de) 2011-08-20 2013-02-21 Clariant International Ltd. Pestizidzubereitungen
WO2013026549A1 (fr) 2011-08-20 2013-02-28 Clariant International Ltd Préparations pesticides

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