EP0138945A1 - Compositions herbicides du type glyphosate - Google Patents

Compositions herbicides du type glyphosate

Info

Publication number
EP0138945A1
EP0138945A1 EP84901474A EP84901474A EP0138945A1 EP 0138945 A1 EP0138945 A1 EP 0138945A1 EP 84901474 A EP84901474 A EP 84901474A EP 84901474 A EP84901474 A EP 84901474A EP 0138945 A1 EP0138945 A1 EP 0138945A1
Authority
EP
European Patent Office
Prior art keywords
glyphosate
composition
aryl
acifluorfen
type herbicide
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP84901474A
Other languages
German (de)
English (en)
Other versions
EP0138945A4 (fr
Inventor
David A. Pate
Lawrence J. Coltharp
Michael Mitchell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
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 Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Publication of EP0138945A1 publication Critical patent/EP0138945A1/fr
Publication of EP0138945A4 publication Critical patent/EP0138945A4/fr
Withdrawn legal-status Critical Current

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
    • 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
    • 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
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals

Definitions

  • This invention relates to improved glyphosate- type herbicidal compositions.
  • Glyphosate N-phosphonomethyl glycine
  • This class of herbicides are especially known for their post-herbicidal effectiveness against grasses and are used for both large scale agricultural applications and also for home and garden-type applications.
  • the glyphosate class of herbicides suffers the disadvantage that they are relatively slow acting especially against certain difficult to kill weed and grass species, such as Bermuda grass.
  • 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid) and its salts are well-known agricultural herbicides which may be applied for selective pre- and post-emergence control of annual broad leaf weeds and grasses in agricultural crops such as soybeans, peanuts, and other large-seeded legumes. These herbicides are generally more active against broad leaf weeds than grasses and are principally applied as post-emergent herbicides. The preparation and use of such herbicides are described in U.S. Patent No. 4,063,929. This patent also generally teaches that such herbicides can be applied in combination with other herbicides including a number of herbicides described in columns 6, 7 and 8 thereof.
  • Oxyfluorfen i.e. 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene
  • Oxyfluorfen is another diphenyl ether-type agricultural herbicide designed for pre- and post-emergence control of a number of species of broad leaf weeds and grasses in crops such as soybean, chrn, cotton, etc. (see Farm Chemicals Handbook (1981) p. C-165).
  • Oxyfluorfen has also been suggested for agricultural uses in combination with glyphosates apparently to increase its herbicidal effectiveness against grasses
  • Bifenox i.e. methyl-5-(2,4-dichlorophenyloxy)-2-nitrobenzoate
  • Bifenox is designed for pre- and post-agricultural herbicide applications particularly for broad leaf control. It has also been suggested to use bifenox in overlay with trifluralin, paraquats or the isopropylamine salt of glyphosate (see Farm Chemicals Handbook (1981) p. C-226).
  • Other diphenyl ether herbicides include nitrofen
  • the invention comprises a herbicidal composition
  • a herbicidal composition comprising a post-emergent herbicidally effective amount of a glyphosate-type herbicide selected from the group of glyphosate and compatible salts or esters thereof and mixtures thereof; an amount of acifluorfen and/or compatible salts or esters thereof, effective to increase the post-emergence herbicidal speed of phytotoxic action of said glyphosate-type. herbicide and a compatible carrier.
  • the invention also comprises a concentrate formulation comprising the aforementioned glyphosate-type herbicide and acifluorfen or salts or esters thereof.
  • the invention comprises a method for destroying vegetation which comprises applying a herbicidally effective amount of a glyphosate-type herbicide in combination with an amount of acifluorfen and/or compatible salts thereof, effective to increase the post-emergence herbicidal speed of action of said glyphosate herbicide; to the foliage and/or stems of said vegetation.
  • Methods of preparing the aforementioned compositions are also encompassed within the invention.
  • the glyphosate-type compounds used in the present invention include compounds represented by Formulas I and la hereinbelow and also compounds which are metabolized by green plants to such compounds or more generally, to the phytotoxic functional equivalent of the compounds of Formulas I and la).
  • Z is cyano; the group -COOR wherein R is hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, aryl, having 6 through 10 carbon atoms or substituted aryl having 1 through 3 substituents independently selected from the group of lower alkyl, lower alkoxy, halo, trifluoromethyl, nitro, and cyano, or a compatible salt- forming cation;
  • R 1 and R 2 are independently hydrogen; lower alkyl; aryl; substituted aryl; biphenyl; or a compatible salt forming cation.
  • M ⁇ is a compatible salt-forming anion;
  • R 3 and R 4 are independently hydrogen; lower alkyl; aryl; substituted aryl; or biphenyl; and
  • Z 1 is cyano; or -COOR' wherein R' is as defined for R but is not a salt- forming cation.
  • the preferred compounds are those wherein Z and Z 1 are -COOR and -COOR', respectively.
  • the preferred compounds are those wherein R, R 1 and R 2 are independently hydrogen or a compatible cation.
  • the organic sulfonium and sulfoxide salts, for example, wherein R 1 and/or R 2 are trimethyl sulfonium cation or trimethyl sulfoxide cation are also desirable.
  • the preferred compounds are those wherein R 1' and R 2' are independently lower alkyl or aryl and Z' is -COOR' wherein R is lower alkyl or aryl.
  • Compatible cations and compatible anions refer respectively to cations and anions which yield the salt form of the compounds of Formula (I) and (la), respectively, and which do not significantly adversely affect the herbicidal properties of the compound.
  • the salt form is more water soluble than the free acid or base form and is hence desirable for formulation and application purposes.
  • Suitable compatible cations include, for example, cations of alkali metals, e.g. sodium, potassium, etc. alkali earth metals, e.g. calcium, magnesium; copper, zinc, iron, nickel manganese, ammonium, and organic ammonium cations, organic phosphonium cations and organic sulfonium and sulfoxide cations preferably having molecular weights below about 300.
  • Suitable organic ammonium cations include cations derived from amines, including cyclic and heterocyclic amines containing 1 or 2 amine groups and includes, for example, alkyl amines, alkylene amines, alkene amines, and alkanol amines.
  • Illustrative species of such amines include, for example: methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methyhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylhept
  • Suitable organic sulfonium and sulfoxide cations include, for example, C 1 -C 10 alkyl, preferably lower alkyl, sulfonium and C 1 -C 10 alkyl, preferably lower alkyl, sulfoxide cations, for example, trimethylsulfonium; ethyldimethylsulfonium; tripropylsulfonium; trimethylsulfoxide; triethylsulfoxide and the like.
  • Suitable procedures for preparing such salts are for example described in U.S. Patent No. 4,315,765, which procedures are hereby incorporated by reference.
  • Suitable phosphonium cations include those having the formula
  • R a , R b , R c and R d are independently C 1 -C 10 alkyl or phenyl, and preferably are lower alkyl. Suitable procedures for preparing such salts are, for example, described in U.S. Patent No. 4,341,549, which procedures are hereby incorporated by reference.
  • Suitable compatible anions include, for example, chloride, bromide, iodide, fluoride, sulfate, sulfite, bisulfite, phosphate, orthophosphate, carbonate, bicarbonate, acetate, butyrate, benzoate, maleate and the like.
  • the compounds of Formulas (I) and (la) are generally known compounds and can be prepared by known methods, such as, for example, described in U.S. Patents Nos. 3,799,758; 3,835,000; 3,950,402; 4,067,719; 4,008,296; 4,252,554; 4,147,719 and 4,369,142 or by obvious modifications of known procedures.
  • R' is hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, aryl or substituted aryl; or -C0NR 7' R 8' wherein R 7 ' and R 8' are independently hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, aryl or substituted aryl; wherein R 5 is lower alkyl, lower alkoxy, hydroxy, lower alkanoyl, arylcarbonyl, substituted arylcarbonyl, trifluoroacetyl, lower alkylthioalkanoyl; amino, alkylamino, nitro, nitroso, or a radical having the formula:
  • R 9 is lower alkyl, lower aklenyl, aryl, or substituted aryl
  • R 11 is lower alkyl, aryl or substituted aryl
  • X is -O- or -S-
  • R 12 is lower alkyl, lower alkenyl, lower alkynyl, aryl, substituted aryl, lower arylalkyl, or substituted lower arylalkyl
  • m is 0, 1, or 2
  • R 1' , R 2' and R 10 are independently selected from the group of substituents defined for R 1 hereinabove;
  • R 6 is hydrogen; lower alkyl; aryl; substituted aryl; lower arylalkyl; lower substituted arylalkyl; -COOR', wherein R' is hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, aryl or substituted aryl; -PO(OR 3 ) (OR 4 ) wherein R 3 and R 4 are as defined hereinabove.
  • the compounds of Formulas lib - VII above are also generally known herbicidally active compounds and can be prepared by known procedures, or obvious modifications thereof (e.g. substitutions of appropriate solvents and appropriately substituted starting materials). Such compounds and procedures are, for example, described in U.S. Patents Nos. 4,035,177; 4,175,946; 4,251,258; 4,231,782; 4,322,238; 4,322,239; 4,323,387; 4,300,942; 4,300,943; U.S. Research Disclosure No. 220,001, filed July 20, 1982 (Derwent No. 73821 E/35); British Patent No. 2,090,596; Belgian Patent No. 888001 (Derwent No. 71783 D/40); Japanese Patent No.
  • acifluorfen-type compounds useful in the present invention can be represented by the formula:
  • M' is hydrogen, lower alkyl, or a compatible salt-forming cation as already discussed hereinabove with respect to Formula (I) and preferably is an alkali metal cation.
  • the compounds of Formula (VIII) are also generally known compounds and can be prepared by known procedures such as, for example, described in U.S. Patent No. 4,063,929, or by obvious modifications of known procedures.
  • esters of Formulas (I)-(VII) and (VIII) can be prepared by neutralization of the corresponding acid or hydroxy moiety with an alcohol or acyl halide.
  • the salts can be prepared via neutralization with the appropriate base or acid. Additional variation in the salt cation, if desired, can also be effected by anion exchange.
  • the composition of the present invention comprises one or more glyphosate-type compounds and an amount of one or more compounds of Formula (VIII) effective to increase the speed of phytotoxic action as compared with the glyphosate-type compuond per se.
  • the composition of the present invention contains about from .1 to .5, preferably about from 0.2 to 0.4 parts by weight of Compound VIII per part of Compound I.
  • mole equivalents typically about from 0.12 to 0.3, preferably 0.14 to 0.23, mole equivalents, based on acifluorfen (i.e. Compound VIII wherein M is H), of Compound VIII is used per mole equivalent of glyphosate-type compound, based on glyphosate (i.e. Compound I wherein R, R 1 and R 3 are each H).
  • Lower ratios of Compound VIII to the glyphosate-type compound generally fail to produce a significant enhancement in the speed of action of Compound I whereas higher ratios of Compound VIII to glyphosate-type compound while increasing the speed of phytotoxicity, are not cost effective and can reduce the overall effectiveness of the glyphosate-type compound producing regrowth.
  • composition is preferably applied in a diluted form comprising a compatible carrier and is generally applied in the same manner as glyphosate-type herbicides and is effective against the same spectrum of broad leaf weeds and grasses with the exception that its phytotoxic action is much faster.
  • the increased speed of phytotoxicity afforded by the present composition is most .dramatic in the early growing season on young broad leaf weeds and grasses and especially on difficult-to-kill species of weeds and grasses, such as pennywort, creeping beggarweed, Bermuda grass, and bahiagrass.
  • the speed of phytotoxic action is even greater than the combined phytotoxic rates of glyphosate and acifluorfen.
  • the increase in speed of action afforded by the present invention is less dramatic because of the relative fast action afforded by glyphosates against mature plants.
  • the composition can be formulated as a liquid, solid, wettable powder, or aerosol and can be supplied as a concentrate designed for dilution prior to application or can be supplied as a ready-to-use formulation. Generally, the composition is preferably applied to the vegetation as a liquid or aerosol.
  • the composition typically comprises about from 0.5 to 0.8 wt percent, preferably 0.6 to 0.7 wt percent of active ingredients, (based on isopropylamine salt of glyphosate plus the sodium acifluorfen salt. In the prescribed ratio given hereinabove) and the remainder compatible carrier optionally containing small amounts of suitable additives.
  • the composition can also be formulated as a concentrate typically containing about from 0.8 to 100 wt percent active ingredients (i.e., glyphosate-type compound(s) plust compound(s) VIII in the prescribed ratio given hereinabove) and the remainder compatible carrier optionally containing small amounts of suitable additives.
  • the concentrate is formulated as a liquid it typically contains about from 0.8 to 60 wt percent, preferably 1 to 55 wt percent, and more preferably, 1 to 50 wt percent, of said active ingredients and a compatible liquid carrier for example, water.
  • the concentrate is supplied as a solid (e.g., powder, granules, etc.) the composition can be 100 wt percent (typically 2 to 100 wt percent) of said active ingredients or can optionally contain a compatible solid carrier (preferably water soluble or water flowable).
  • a compatible solid carrier preferably water soluble or water flowable
  • compatible carrier refers to carrier materials which are compatible with the herbicidally active ingredients and which do not significantly adversely affect their herbicidal properties save to dilute it.
  • composition can also contain small amounts, typically less than 1-5 wt percent, of various optional additives such as wetting agents, stabilizers, emulsifiers, solvents, etc.
  • optional additives such as wetting agents, stabilizers, emulsifiers, solvents, etc.
  • Examples of such additives and general glyphosate formulations are, for example, described in U.S. Patent No. 4,315,765 which description is hereby incorporated by reference.
  • Suitable liquid carriers which can be used, include, for example, water, organic solvents, for exampie, benzene, toluene, kerosene, diesel fuel, fuel oil, petroleum naphtha, etc.
  • Solid carriers can also be used but are generally less convenient than liquid carriers. Suitable solid carriers include, for example, fine clays, walnut shell flour, cottonseed hulls, wheat flour, wood flour, etc.
  • the present invention can also be applied as an aerosol containing the glyphosate-type compound (s) and Compound(s) VIII in the prescribed ratio along with a suitable aerosol carrier, such as halogenated alkanes and optional additives.
  • a suitable aerosol carrier such as halogenated alkanes and optional additives.
  • the composition is preferably applied as a liquid formulation containing about from 0.3 to 1, more preferably 0.4 to 0.7, weight percent of the glyphosate-type compound (based on the isopropylamine salt of glyphosate) and about from 0.08 to 0.5, more preferably 0.1 to 0.3, weight percent of Compound VIII, based on the sodium salt of acifluorfen.
  • a glyphosate-type compound concentration of about 0.5 wt percent (based on the glyphosate isopropylamine salt) and a Compound VIII concentration of about 0.12 wt percent (based on the sodium salt of acifluorfen).
  • the liquid formulations preferably contain about from 0.017 to 0.06, more preferably gram mole equivalents, based on glyphosate, of the glyphosate-type compound and about from 0.002 to 0.013, more preferably 0.0025 to 0.008, gram mole equivalents, based on acifluorfen, of Compound(s) (VIII) per kilogram of formulation. Very good results are obtained using about 0.02 mole equivalents, based on glyphosate, of glyphosate-type compound and about 0.003 gram mole equivalents, based on acifluorfen, of
  • Compound VIII per kilogram of formulation.
  • the remainder of the liquid formulation is liquid carrier or solvent optionally containing suitable additives as explained above.
  • Water is generally the preferred carrier when water-soluble forms of the active compounds are used.
  • the composition can also be formulated as an aerosol for home and garden applications having about the same concentration ranges of the glyphosate-type compound (s) and Compound (s) VIII as the liquid formulations described above.
  • the formulation is then applied to the foliage and/or stems of the vegetation, for example, by simple spraying. As in the case of conventional home and garden glyphosate formulations, best results are obtained when the foliage is thoroughly wetted with the formulation.
  • compositions of the invention can be conveniently prepared by simple mixing or blending of the ingredients.
  • Compounds I and la or I-VII refers to the compounds defined by Formulas I and la or I-VII, respectively, given hereinabove, and includes mixtures thereof.
  • Compound VIII refers to the compounds defined by Formula VIII, given hereinabove, and includes mixtures thereof.
  • alkyl refers to both straight-chained and branch-chained alkyl groups.
  • lower alkyl refers to alkyl groups having 1 through 6 carbon atoms and includes, for example, methyl, ethyl, isopropyl, t-butyl, pentyl, hexyl and the like.
  • alkylene refers to the group -(CH 2 ) n -.
  • alkenyl refers to the unsaturated counterpart of alkyl having one or two double bonds.
  • lower alkenyl refers to alkenyl having 2 through 6 carbon atoms.
  • alkoxy refers to the group R 1 O- wherein R 1 is alkyl.
  • lower alkoxy refers to alkoxy having 1 through 6 carbon atoms.
  • alkoxyalkyl refers to the group
  • lower alkoxyalkyl refers to the group R'OR"- wherein R' and R" are each lower alkyl and having a total of from 2 through 8 carbon atoms. Typically R" is methyl.
  • lower alkylamine refers to the group
  • aryl refers to aryl groups having 6 through 10 carbon atoms and includes phenyl, naphthyl, and the like.
  • the preferred aryl group is phenyl.
  • substituted aryl refers to aryl groups having 1 through 3, preferably 1 or 2, substituents independently selected from the group of lower alkyl, lower alkoxy, halo, trifluoromethyl, cyano, nitro and hydroxy.
  • the preferred substituted aryl group is substituted phenyl.
  • lower arylalkyl refers to the group ArR'- wherein Ar is aryl and R' is lower alkyl.
  • R 1 is methyl or ethyl and/or Ar is phenyl.
  • lower substituted lower arylalkyl refers to the group A'rR'- wherein A'r is substituted aryl and R' is lower alkyl.
  • alkanoyl refers to the group
  • R' is alkyl.
  • lower alkanoyl refers to the group
  • R' is lower alkyl
  • arylcarbonyl refers to the group
  • Ar is aryl
  • substituted arylcarbonyl refers to the group
  • Ar' is substituted aryl
  • lower alkylthioalkanoyl refers to the group
  • R' and R'' are independently lower alkyl.
  • the lower alkylthioalkanoyl has from 2 through 8 carbon atoms.
  • the formulations of the present invention were field-tested for their speed of phytotoxicity against a variety of mature broad leaf weeds and mature grasses. Side-by-side comparison tests were also conducted at the same time against the same mature weed and grass species using formulations containing only the glyphosate compound or only the acifluorfen compound at the same concentration. Four replicate one square foot plots of the subject plants were tested for each weed and grass species per formulation. An untreated plot was also run at the same time for each species as a check.
  • the formulations were prepared by diluting standard commercial 41%, by weight, solutions of the isopropylaraine salt of glyphosate (sold under the Trademark Roundup® by the Monsanto Company of St. Louis, Missouri, U.S.A.) and/or a standard commercial 21.4%, by weight, solution of the sodium salt of acifluorfen (sold under the Trademark Blazer ® by the Rohm and Haas Company of Philadelphia, Pennsylvania, U.S.A.) with the appropriate amount of water to yield the concentrations indicated in the tables set forth below.
  • the formulations were applied to the foliage of the test plant with a trigger sprayer to give thorough coverage. Accordingly, as in home and garden use, different amounts of formulation were applied to the plant depending on the size of the plant. The average amount of formulation used per replicate for a given formulation is indicated in the tables given below.
  • the plants were periodically observed and rated for phytotoxic effects and physiological response to the treatment. A rating scale of 0 to 100 was used, 0 representing no phytotoxicity and 100 representing complete kill.
  • the above-described tests were conducted late in the growing season under field conditions (i.e. outside as opposed to greenhouse testing) and were designed to duplicate home and garden applications. The tests were conducted in the state of Florida during the months of October-November.
  • the glyphosate plus acifluorfen formulations of the present invention exhibit increased speeds of phytotoxicity over glyphosate alone at the same concentration. This is shown by the increased phytotoxicity shown in the 3- to 7-day period after application as compared with glyphosate alone. In some instances the increased phytotoxicity extends beyond this period but ultimately glyphosate alone is generally effective alone to give substantially complete control.

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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

Compositions herbicides du type glyphosate comprenant une quantité moindre d'un herbicide du type acifluorfène. Ces compositions présentent un accroissement de la vitesse de l'action phytotoxique par rapport au glyphosate et sont particulièrement utiles dans des applications herbicides domestiques et dans le jardinage.
EP19840901474 1983-03-16 1984-03-02 Compositions herbicides du type glyphosate. Withdrawn EP0138945A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47583083A 1983-03-16 1983-03-16
US475830 1983-03-16

Publications (2)

Publication Number Publication Date
EP0138945A1 true EP0138945A1 (fr) 1985-05-02
EP0138945A4 EP0138945A4 (fr) 1985-09-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19840901474 Withdrawn EP0138945A4 (fr) 1983-03-16 1984-03-02 Compositions herbicides du type glyphosate.

Country Status (4)

Country Link
EP (1) EP0138945A4 (fr)
AU (1) AU561761B2 (fr)
CA (1) CA1222639A (fr)
WO (1) WO1984003607A1 (fr)

Families Citing this family (12)

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Publication number Priority date Publication date Assignee Title
AU3148384A (en) * 1983-10-28 1985-05-02 Chevron Research Company Glyphosate type herbicide plus oxyfluorfen
US5580841A (en) * 1985-05-29 1996-12-03 Zeneca Limited Solid, phytoactive compositions and method for their preparation
US5468718A (en) * 1985-10-21 1995-11-21 Ici Americas Inc. Liquid, phytoactive compositions and method for their preparation
US5147444A (en) * 1986-06-27 1992-09-15 Rhone Poulenc Agrochimie Herbicidal compositions based on a glyphosate herbicide and acifluorfen
US5047079A (en) * 1986-08-18 1991-09-10 Ici Americas Inc. Method of preparation and use of solid, phytoactive compositions
EP0340216B1 (fr) * 1987-10-28 1993-05-19 Rhone-Poulenc Agrochimie Compositions comprenant des combinaisons d'herbicides de type glyphosate et de type phenoxybenzoique
EP0334041A3 (fr) * 1988-02-23 1990-03-28 Mitsubishi Petrochemical Co., Ltd. Composition herbicide
FR2644036B1 (fr) * 1989-03-07 1992-01-17 Rhone Poulenc Agrochimie Combine herbicide constitue d'un emballage polymere hydrosoluble et d'un herbicide contenant de la n-phosphonomethylglycine
EP0617894B1 (fr) * 1993-04-02 1998-12-16 Monsanto Europe S.A./N.V. Compositions herbicides de glyphosate sous forme de concentrés liquides
US5525577A (en) * 1994-11-17 1996-06-11 Basf Corporation Safening effect of combinations of glyphosate and acifluorfen
DE19607633A1 (de) * 1996-02-29 1997-09-04 Bayer Ag Herbizide Mittel auf Basis von N-Phosphonomethyl-glycinestern
DE19752552A1 (de) 1997-11-27 1999-06-02 Hoechst Schering Agrevo Gmbh Tensidsysteme für flüssige wässrige Zubereitungen

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US3799758A (en) * 1971-08-09 1974-03-26 Monsanto Co N-phosphonomethyl-glycine phytotoxicant compositions
US4063929A (en) * 1973-02-12 1977-12-20 Rohm And Haas Company Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers
US3868407A (en) * 1973-11-21 1975-02-25 Monsanto Co Carboxyalkyl esters of n-phosphonomethyl glycine
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
US4221583A (en) * 1978-12-22 1980-09-09 Monsanto Company N-Phosphonomethylglycinonitrile and certain derivatives thereof
HU182980B (en) * 1979-12-28 1984-03-28 Nitrokemia Ipartelepek Concentrates and spray solutions containing n-bracket-phosphono-methyl-bracket closed-glycine
US4431437A (en) * 1981-01-08 1984-02-14 Gaf Corporation Bioactant translocation agent

Non-Patent Citations (2)

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Title
No relevant documents have been disclosed *
See also references of WO8403607A1 *

Also Published As

Publication number Publication date
CA1222639A (fr) 1987-06-09
AU561761B2 (en) 1987-05-14
WO1984003607A1 (fr) 1984-09-27
AU2698384A (en) 1984-10-09
EP0138945A4 (fr) 1985-09-09

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