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WO2008008762A2 - Composition herbicide - Google Patents

Composition herbicide Download PDF

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Publication number
WO2008008762A2
WO2008008762A2 PCT/US2007/073132 US2007073132W WO2008008762A2 WO 2008008762 A2 WO2008008762 A2 WO 2008008762A2 US 2007073132 W US2007073132 W US 2007073132W WO 2008008762 A2 WO2008008762 A2 WO 2008008762A2
Authority
WO
WIPO (PCT)
Prior art keywords
trifluoromethyl
phosphonomethyl
fluoro
chloro
pyrimidinedione
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.)
Ceased
Application number
PCT/US2007/073132
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English (en)
Other versions
WO2008008762A3 (fr
Inventor
Thomas E. Hashman
James T. Bahr
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.)
FMC Corp
Original Assignee
FMC Corp
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 FMC Corp filed Critical FMC Corp
Publication of WO2008008762A2 publication Critical patent/WO2008008762A2/fr
Anticipated expiration legal-status Critical
Publication of WO2008008762A3 publication Critical patent/WO2008008762A3/fr
Ceased legal-status Critical Current

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • This invention relates to herbicidal compositions containing an agriculturally acceptable salt of N-(phosphonomethyl)glycine and 3-(4-chloro-6-fluoro-2- trifluoromethyl-benzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.
  • U. S. Patent 6,077,812 discloses 3-(4-chloro-6-fluoro-2-trifluoromethyl- benzimidazol-7-yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione.
  • U. S. Patent 3,799,758 discloses N-(phosphonomethyl)glycine and agriculturally acceptable salts thereof.
  • an herbicidal composition comprising a first herbicide and a second herbicide in which the first herbicide is an agriculturally acceptable salt of N-(phosphonomethyl)glycine and the second herbicide is 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione, wherein the first herbicide and the second herbicide are present in an herbicidally effective amount, has unexpected advantageous properties over the individual components.
  • composition comprising an herbicidal composition comprising a first herbicide and a second herbicide in which the first herbicide is an agriculturally acceptable salt of N-(phosphonomethyl)glycine and the second herbicide is 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H) pyrimidinedione has unexpected advantageous properties in weed control over the individual components, for example, the mixture controls a broader variety of weeds at lower rates than either component alone. The combination can also be useful in overcoming reduced sensitivity by a weed to either of the individual components.
  • N-(phosphonomethyl)glycine is as follows: HO 2 CCH 2 NHCH 2 PO(OH) 2 .
  • the structural formula for 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is as follows:
  • weed and weeds refer to any unwanted vegetation in agricultural crops and orchards, as well as, but not limited to, around buildings, along fences, roadways and rail lines.
  • the ratio of an agriculturally acceptable salt ofN-(phosphonomethyl)glycine to 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6- trifluoromethyl-2,4(lH,3H)pyrimidinedione varies over a wide range but is usually in the range 250: 1 to 8:1, preferably 125: 1 to 10: 1.
  • herbicides can be employed in conjunction with the first and second herbicides described above providing they do not adversely affect the interaction between the components of this invention. For example it can sometimes be useful to include additional herbicides to extend the range of activity in order to control a wider spectrum of weeds.
  • an herbicidal composition comprising an agriculturally acceptable salt of N-(phosphonomethyl)glycine and 3- (4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione for controlling weeds.
  • Another embodiment of the present invention is a method for controlling broadleaf and grass weeds in crops such as corn and fruit tree orchards or as a pre- plant burn down herbicide composition for corn, wheat, rye, rice, sunflower, soybean, cotton or non-crop applications which comprises applying an herbicidally effective amount of a composition comprising an agriculturally acceptable salt of N- (phosphonomethyl)glycine and 3 -(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol- 7-yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione, either together or sequentially, to a locus where weeds are present or are expected to be present.
  • a composition comprising an agriculturally acceptable salt of N- (phosphonomethyl)glycine and 3 -(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol- 7-yl)-l-methyl-6-trifluoromethyl-2
  • compositions of the present invention may be employed in many forms and are often most conveniently prepared in aqueous form immediately prior to use.
  • One method of preparing such a composition is referred to as "tank mixing" in which the ingredients in their commercially available form are mixed together by the user in a quantity of water.
  • compositions containing agriculturally acceptable salts of N-(phosphonomethyl)glycine and 3-(7- chloro-5-fluoro-2-trifluoromethylbenzimidazol-4-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pryimidinedione may be formulated into a more concentrated primary composition which is diluted with water or other diluent before use.
  • Such compositions may comprise a surface active agent in addition to the active ingredients and examples of such compositions are set forth below.
  • the herbicidal compounds of the present invention may be formulated as a granule of relatively large particle size (for example, 8/16 or 4/8 US Mesh), as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as aqueous emulsions, as solutions, or as any of the other known types of agriculturally -useful formulations, depending on the desired mode of application to the areas in which suppression of vegetation is desired.
  • These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of the total of the two herbicides.
  • the composition can be in the form of a dispersible solution which comprises the herbicides dissolved in a water-miscible solvent with the addition of a dispersing agent.
  • it can comprise the herbicides in the form of a finely ground powder in association with a dispersing agent and intimately mixed with water to give a paste or cream which can if desired be added to an emulsion of oil in water to give a dispersion of the two herbicides in an aqueous oil emulsion.
  • the composition can be in the form of water-soluble or water- dispersible granules that disperse readily in water or other dispersant.
  • Water-soluble or water-dispersible granules normally are prepared to contain about 5-80% of the herbicides, depending on the absorbency of the carrier, and usually also contain a wetting, dispersing or emulsifying agent to facilitate dispersion and may contain a preservative.
  • Typical carriers for water-soluble or water-dispersible granules include Fuller's earth, natural clays, silicas, and other highly absorbent, readily wet inorganic diluents.
  • a useful water-soluble or water-dispersible granule formulation contains 26.71 parts of the herbicidal compound, 30.90 parts of ammonium sulfate, 30.89 parts of continental clay, 10.00 parts of sodium lignosulfonate as a dispersant, 1.00 part of sodium dioctylsuccinate as a wetting agent and 0.50 part of citric acid as a preservative.
  • the mixture is milled, diluted with water to form a paste and the paste is extruded and dried to produce granules.
  • dusts which are free flowing admixtures of the herbicides with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the herbicides. These finely divided solids have an average particle size of less than about 50 microns.
  • a typical dust formulation useful herein is one containing 1.0 part or less of the herbicidal compounds and 99.0 parts of talc.
  • Also useful formulations for the herbicidal compositions of the present invention are wettable powders in the form of finely divided particles that disperse readily in water or other dispersant.
  • the wettable powder is ultimately applied to the locus where weed control is needed either as a dry dust or as an emulsion in water or other liquid.
  • Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders are prepared to contain about 5-80% of the herbicides, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • a useful wettable powder formulation contains 80.0 parts of the herbicidal compounds, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents. Additional wetting agents and/or oils will frequently be added to a tank mix to facilitate dispersion on the foliage of the plant.
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • these concentrates are dispersed in water or other liquid carriers and applied as a spray to the area to be treated.
  • the percentage by weight of the herbicidal compounds may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of the herbicidal compounds by weight of the total composition.
  • Suspension concentrate formulations may also be employed. These are similar to ECs, except that the herbicidal compounds are suspended in a liquid carrier, generally water. Suspension concentrates, like ECs, may include a small amount of a surfactant, and will typically contain the herbicidal compounds in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the total composition.
  • a useful suspension concentrate formulation contains 22.0 parts of the herbicidal compounds, 2.6 parts of an ethoxylated/propoxylated block copolymer surfactant, 0.4 part phosphate ester surfactant, 0.8 part thickening agent, 6.0 parts antifreeze agent, 0.1 antifoam agent, 0.05 part anti-bactericide and 44.0 parts distilled water.
  • suspension concentrates may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • compositions include suspensions of the herbicidal compounds in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • Still other useful formulations for these herbicidal compositions include simple solutions of the herbicides in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
  • Granular formulations, wherein the herbicides are carried on relative coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy.
  • Pressurized sprays, typically aerosols wherein the herbicides are dispersed in finely divided form as a result of vaporization of a low- boiling dispersant solvent carrier may also be used.
  • Another useful formulation for the herbicidal compositions of the present invention is micro encapsulation.
  • This method of formulation is a process in which either one or both of the herbicidal compounds may be encapsulated in a shell of polyurea, polyamide or amide-urea copolymer as disclosed in EP 0792100 Bl and U. S. Patent 5,583,090.
  • one of the herbicidal compounds is used as an emulsifiable concentrate and the second herbicidal compound is dispersed as a powder in this concentrate.
  • the concentrate of the first and second herbicides (when used as the sole active components) in a composition for direct application to the crop by conventional ground methods is preferably within the range of 0.001 to 10 % by weight of the composition, especially 0.005 to 5 % by weight, but more concentrated compositions containing up to 40 % may be desirable.
  • Typical wetting, dispersing or emulsifying agents that may be used in the compositions of the present invention include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide.
  • Many other types of useful surface-active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition.
  • the invention is illustrated in the following Examples which describe experiments in which a beneficial effect was observed.
  • the desired concentration of the active ingredients was achieved by diluting, with water, the commercially available herbicide formulation of N-(phosphonomethyl)glycine- isopropylammonium salt (Roundup® Herbicide, Monsanto Corporation), the commercially available herbicide formulation of N-(phosphonomethyl)glycine- potassium salt (Roundup WeatherMax® Herbicide, Monsanto Corporation), a 25% by weight water-dispersible granule formulation (25 WG) of 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione or a 240 gram per liter suspension concentrate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl
  • compositions of the present invention were tested for herbicidal efficacy as compared with the individual components used in the composition in the following manner:
  • a test composition of N-(phosphonomethyl)glycine -isopropylammonium salt (Roundup® Herbicide) was prepared in a spray tank that provided a 0.75 pound per acre application rate of N-(phosphonomethyl)glycine -isopropylammonium salt.
  • Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (25 WG) were prepared in a spray tank that provided the appropriate application rate of 3-(4-chloro-6-fluoro- 2-trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.
  • a crop oil concentrate was added to these test compositions.
  • Test compositions of mixtures of N-(phosphonomethyl)glycine - isopropylammonium salt (Roundup® Herbicide) and 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione (25 WG) were prepared in a tank mix that provided appropriate rates of application of combinations of N-(phosphonomethyl)glycine - isopropylammonium salt and 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione.
  • a crop oil concentrate was added to these test compositions.
  • test rate was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 15 gallons per acre.
  • the experimental design used randomized plots with one post-emergent treatment and four replications per test trial.
  • the size of each experimental plot was 10 feet by 30 feet.
  • the appearance and the population of the weeds were assessed and averaged at 21 days after application of each test rate, the results are in Table 1 below.
  • the test weeds include common lambsquarters (Chenopodium album), ivyleaf morningglory (Ipomoea hederacea), pitted morningglory (Ipomeoa lacunosa), Eastern, black nightshade (Solarium ptycanthum), common ragweed (Ambrosia artemisifolia), giant ragweed (Ambrosia trifida), hemp sesbania (Sesbania exaltata), prickly sida (Sida spinosa), Pennsylvania smartweed (Polygonum Pennsylvania), velvetleaf (Abutilon theophrasti) and common water hemp(Amaranthus rudis).
  • compositions of the present invention were tested for herbicidal efficacy as compared with the individual components used in the composition in the following manner:
  • test composition of N-(phosphonomethyl)glycine -potassium salt (Roundup WeatherMax®) was prepared in a spray tank that provided a 1.0 pound per acre application rate of N-(phosphonomethyl)glycine -potassium salt.
  • a crop oil concentrate and urea ammonium nitrate was added to the test compositions.
  • Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- 1 - methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (240 gram per liter suspension concentrate) were prepared in a spray tank that provided the appropriate application rate of 3 -(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethy 1- 2,4(lH,3H)pyrimidinedione.
  • a crop oil concentrate and urea ammonium nitrate was added to these test compositions.
  • 2,4(lH,3H)pyrimidinedione (240 gram per liter suspension concentrate) were prepared in a tank mix that provided appropriate rates of application of combinations of N- (phosphonomethyl)glycine -potassium salt and 3-(4-chloro-6-fluoro-2- trifluoromethy lbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.
  • a crop oil concentrate and urea ammonium nitrate was added to these test compositions.
  • test rate was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 15 gallons per acre.
  • the experimental design used randomized plots with one post-emergent treatment and four replications per test trial. The size of each experimental plot was 10 feet by 30 feet.
  • the appearance and the population of the weeds were assessed and averaged at 28 to 31 days after application of each test rate, the results are in Table 2 below.
  • the test weeds include Persian speedwell (Veronica persica), common speedwell (Veronica officinalis), common mallow (Malva neglecta), red clover (Trifolium pratense), evening- primrose (Oenothera biennis), hairy fleabane (Conyza bonariensis), prostrate knotweed (Polygonum aviculare), coast f ⁇ ddleneck (Amsinckia intermedia), wild radish (Raphanus raphanistrum), downy brome (Bromus tectorum), henbit (Lamium amplexicaule), common chickweed (Stellaria media), redstem filaree (Erodium cicutarium), common dandelion (Taraxacum officinale), California brome grass (Bromus carinatus), bristly mallow (Modiola caroliniana), wild carrot (

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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 concerne une composition herbicide qui contient un premier et un second herbicide, le premier consistant en un sel acceptable sur le plan agricole de N-(phosphonométhyl)glycine et le second en de la 3-(4-chloro-6-fluoro-2-trifluorométhylbenzimidazol-7-yl)-1-méthyl-6-trifluorométhyl-2,4(1H,3H)pyrimidinedione. L'invention concerne également un procédé herbicide d'utilisation de celle-ci.
PCT/US2007/073132 2006-07-10 2007-07-10 Composition herbicide Ceased WO2008008762A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81974806P 2006-07-10 2006-07-10
US60/819,748 2006-07-10

Publications (2)

Publication Number Publication Date
WO2008008762A2 true WO2008008762A2 (fr) 2008-01-17
WO2008008762A3 WO2008008762A3 (fr) 2009-02-19

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PCT/US2007/073132 Ceased WO2008008762A2 (fr) 2006-07-10 2007-07-10 Composition herbicide

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Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077812A (en) * 1997-02-26 2000-06-20 Fmc Corporation Cycloimido-substituted benzofused heterocyclic herbicides
JP2000351703A (ja) * 1999-06-07 2000-12-19 Sumitomo Chem Co Ltd 除草剤組成物

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WO2008008762A3 (fr) 2009-02-19

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