EP0515679A1 - Formulations concentrees precipitees fluides, leur preparation et leurs emplois agricoles - Google Patents

Formulations concentrees precipitees fluides, leur preparation et leurs emplois agricoles

Info

Publication number
EP0515679A1
EP0515679A1 EP92906371A EP92906371A EP0515679A1 EP 0515679 A1 EP0515679 A1 EP 0515679A1 EP 92906371 A EP92906371 A EP 92906371A EP 92906371 A EP92906371 A EP 92906371A EP 0515679 A1 EP0515679 A1 EP 0515679A1
Authority
EP
European Patent Office
Prior art keywords
water
concentrate
agricultural
insoluble
solid water
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Withdrawn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
EP92906371A
Other languages
German (de)
English (en)
Other versions
EP0515679A4 (en
Inventor
Jeffrey L. Jensen
Tony D. Flaim
Norman H. Kurihara
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.)
Corteva Agriscience LLC
Original Assignee
DowElanco LLC
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 DowElanco LLC filed Critical DowElanco LLC
Publication of EP0515679A1 publication Critical patent/EP0515679A1/fr
Publication of EP0515679A4 publication Critical patent/EP0515679A4/en
Withdrawn legal-status Critical Current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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

Definitions

  • the present invention is directed to
  • concentrate formulations contain a solid waterinsoluble active material and a dispersant solubilized in a water miscible solvent which upon dilution with water, produces a narrowly distributed fine particle suspension suitable for use in agricultural spraying operations.
  • These concentrate formulations being true solutions exhibit excellent storage stability and the particle suspension formed on dilution with water is readily suspendable and resistant to crystal growth.
  • the solid material usually constitutes from about 5 to 60 percent by weight and is present as distinct particles in the size range of 1 to 20 microns. Particle sizes of ⁇ 10 microns are preferred to enhance the suspensability of the active material in both the concentrate and upon dilution with water for field use. An even smaller particle size range, i.e., ⁇ 1 micron, depending on a specific active's mode of action, can also provide for improved biological efficacy. For example, when the diluted formulation is sprayed on a target surface, greater coverage and dissolution of the active material on the sprayed surface is achieved.
  • the active material cannot be readily reduced to the optimum particle size using mechanical methods.
  • a desirable formulation for field use, involving active materials which are insoluble in both water and water immiscible solvents, would be one in which the active material is maintained homogeneously throughout the product concentrate prior to use. The user can then accurately prepare the end use system in the field and apply this to the target host in the appropriate dosage by controlling the amount of dilution in water.
  • This product concentrate must readily
  • the active material's particle size must be of such a size to ensure that a uniform spray solution can be maintained with minimal tank agitation, as well as, ensuring satisfactory, if not enhanced biological efficacy. It would also be
  • the present invention is directed to three component stable pesticidal agricultural concentrates, which are defined as "precipitated flowables", and their preparation.
  • the present invention is also directed to the agricultural uses of the spray system formulations created by diluting the "precipitated flowable" concentrate with water.
  • These concentrates of the present invention are comprised essentially of
  • a water miscible solvent wherein said concentrate is in the form of a true solution and not susceptible to the general storage concerns of conventional suspension concentrates.
  • the room temperature viscosity is between 10 and 1500 cps (centipose per second) at a shear rate of 100 sec-1 as measured by a conventional viscosity measuring device such as, for example, a Rotovisco RV 12 Viscometer
  • VMD volume median diameter
  • This diluted phase of the "precipitated flowable” exhibits excellent static stability and is resistant to unwanted crystal growth for time periods that equal or exceed 4 hours.
  • one or more active pesticidal materials together with one or more appropriate dispersants in a ratio of from about 1 percent by weight of the active to about 6 percent by weight of the dispersant up to a ratio of about 30 percent by weight of the active to about 1 percent by weight of the dispersant, are
  • solubilized in a water-miscible solvent which comprises the remainder of the concentrate and which is usually present in from about 50 to about 95 percent by weight of the total concentrate.
  • a water-miscible solvent which comprises the remainder of the concentrate and which is usually present in from about 50 to about 95 percent by weight of the total concentrate.
  • the preparation can also be conducted at temperatures up to about 50°C.
  • active water-insoluble pesticidal materials useful in preparing these concentrates of the present invention have melting points greater than 50°C. and an inherent water solubility of less than 500 parts per million.
  • pesticidal materials useful in preparing these above concentrate formulations are pesticidal materials which include but are not limited to those set forth below, for example:
  • Atrazine 2-chloro-4-ethylamino-6-isopropyl- amino-s-triazine
  • Naptalam N-1-naphthylphthalamic acid
  • Chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea
  • Oxadiazon 5-t-butyl-3-(2,4-dichloro-5-isopropoxy- phenyl)-1,3,4-oxadiazol-2-one;
  • Chlorsulfuron 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin ⁇
  • 2,4-DB 4-(2,4-dichlorophenoxy)butyric acid
  • MCPB 4-(4-chloro-o-tolyoxy)butyric acid
  • Dithianon 5,10-dihydro-5,10-dixonaphtho-(2,3-b)-1,4-dithiin-2,3-dicarbonitrile;
  • Tralkoxydim 2-(1-(ethoxyimino)propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-enone;
  • Heptachlor 1,4,5,6,7,8,8-heptachlor-3a,7,7a-tetrahydro-4,7-methanoindene;
  • Carbendazim methyl benzimidazol-2-ylcarbamate
  • Vinclozolin 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione
  • Procymidone N-(3,5-dichlorophenyl)-1,2-dimethyl- cyclopropane-1,2-dicarboximide
  • Triforine 1,4-bis(2,2,2-trichloro-1-formamidoethyl)piperazine;
  • Chlorothalonil tetrachloroisophthalonitrile.
  • dispersants useful in preparing these concentrates of the present invention include, for example:
  • Pluronic P-105 condensate of ethylene oxide with hydrophobia base formed by condensing propylene oxide with propylene glycol; a product of BASF Wyandotte Ind. Chem. Group.;
  • T-Det N-6 nonylphenol-6 mole ethylene oxide
  • T-Det N-14 nonylphenol-14 mole ethylene oxide
  • T-Det N-30 nonylphenol-30 mole ethylene oxide
  • T-Det N-50 nonylphenol-50 mole ethylene oxide
  • Polyfon H sodium salt of polymethacrylic acid; a product of W.R. Grace & Co.;
  • Daravan No, 1 sodium naphthalene sulfonic acid formaldehyde; a product of R.T.
  • PVP K-15 polyvinylpyrrolidone polymer
  • PVP/VA E-735 vinylpyrrolidone/vinyl acetate copolymer (50 percent ethanol
  • Gafquat 734 vinylpyrrolidone/quaternized
  • dimethylaminoethylmethacrylate copolymer 50 percent ethanol solution
  • a product of GAF Corp. a product of GAF Corp.
  • Gantrez AN-119 poly(methyl vinyl ether/maleic anhydride) Low-mol.Wt. grade; a product of GAF Corp.;
  • Genamin 0-200 fatty amine ethoxylate (oleyl; 20 moles ethylene oxide); a product of American Hoechst Corp.
  • Genamin S-200 fatty amine ethoxylate (stearyl; 20 moles ethylene oxide); a product of American Hoechst Corp.;
  • Genapol 0-150 fatty alcohol ethoxylate (oleyl; 15
  • dispersants may be used alone or in combination depending on the specific final usage.
  • Representative water miscible solvents useful in preparing these concentrates of the present invention include, for example: dimethyl ketone;
  • the concentrate Prior to use, the concentrate is diluted with water to prepare these final aqueous formulations containing from about 0.00024 to about 0.24 percent by weight of the active material.
  • a pesticidal or pesticidally effective amount of the active compound is used as the toxicant for contact with the pest or its habitat.
  • the pesticidal amount is that quantity which elicits toxic mortality among these treated pests.
  • the present invention also embraces the employment of the present formulation in combination with one or more additional pesticidal compounds.
  • additional pesticidal compounds may be other types of insecticides, nematocides, miticides, arthropodicides, herbicides, fungicides or bactericides that are
  • the additional pesticidal compound(s) is employed as a supplemental toxicant for ihe same or for a different pesticidal use or as an additament.
  • These compounds in combination can generally be present in a ratio of from about 1 to about 100 parts of the compound of the present invention with from about 100 to about 1 part of the additional compound.
  • the concentrate is prepared and then diluted with water and the volume median diameter (VMD) of the particles in the dispersed particle suspension thus prepared is measured with a laser scattering particle sizer such as a Cilas 715 Granulometer (manufactured by Cilas Alcatel or an equivalent instrument) to determine if the volume median diameter is less than 1 micron. If the volume median diameter of the diluted system exceeds 1 micron either initially or within 4 hours after dilution, the diluted system is considered outside the specifications of the present invention.
  • VMD volume median diameter
  • Example I A seven (7.0) gram (g) concentrate formulation was prepared by sequentially solubilizing 0.42 g
  • 1:100 dilutions were prepared by mixing one (1) milliliter (mL) of the thus prepared concentrate with 100 mL of room temperature water of various hardness types. Twenty four hours thereafter, the particle size of these particles dispersed in the diluted formulation was measured with a Cilas 715 Granulometer and these results are set forth hereinbelow in Table I.
  • a fifty (50.0) gram (g) concentrate formulation was prepared by sequentially solubilizing 3.00 g (6 percent by weight) of Atrazine and 0.15 g (0.3 percent by weight) of T-Det N-50 in 46.85 g (93.7 percent by weight) of NMP. 1:100 dilutions were prepared by mixing one (1) milliliter (mL) of the thus prepared concentrate with 100 mL of water of various temperatures. Twenty four hours thereafter, the particle size of the particles dispersed in the diluted formulation was measured with a Cilas 715 Granulometer and these results are set forth below in Table II.
  • 1:100 dilutions were prepared by mixing one (1) milliliter (mL) of the concentrate prepared above in Example II with 100 mL of room temperature water both with and without agitation. Twenty four hours
  • Atrazine and a predetermined amount of Pluronic P-105 (P-105) in a predetermined amount of NMP.
  • 1:100 dilutions were then prepared by mixing one (1) milliliter (mL) of one of the thus prepared concentrates with 100 mL of room temperature water.
  • a thirty (30.0) gram (g) concentrate was prepared by sequentially solubilizing 1.8 g of one of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(2,2,2- -trifluoroethoxy)phenyl)propanamide or 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)propanamide and 3.6 g of Ganex P-904 in 24 g of NMP.
  • Serial dilution formulations were then prepared by mixing a predetermined amount of the thus prepared concentrate with separate 80 mL portions of room
  • Giant foxtail plants grown in beds of good agricultural soil and grown in a greenhouse to the 2-3 leaf stage were sprayed using an Allen greenhouse track sprayer (manufactured by Allen Machine Works) equipped with two (2) 8003 flat fan nozzles (manufactured by the Spraying Systems Co.) at a traversing speed and spray pressure so as to deliver a total spray volume of 20 gallon/acre, with one of these above prepared formulations at a predetermined treating rate.
  • Other beds of these plants were sprayed with a Ganex P-904, NMP and Silwet L-77 mixture containing no active compound to serve as controls. After treatment, these beds were maintained for 13 days under greenhouse conditions conducive for good plant growth. At the end of this period, these beds were examined to determine the amount of kill and control of the foxtail plants.
  • the dosage rate in the equivalent of pounds per acre and the percent kill and control are set forth below in Table V.

Landscapes

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

Abstract

L'invention a trait à des formulations concentrées pesticides économiques et stables, notamment des formulations herbicides, insecticides et fongicides ainsi qu'à leurs emplois agricoles sous forme diluée dans de l'eau. Lesdits concentrés contiennent une matière active solide insoluble dans l'eau ainsi qu'un dispersant pouvant être solubilisé dans un solvant miscible à l'eau, lequel, lors de la dilution dans de l'eau, produit une suspension de fines particules étroitement réparties adaptées à une utilisation dans des opérations de pulvérisation agricoles. Ces formulations concentrées sont de véritables solutions et elles présentent une excellente stabilité pendant leur stockage, la suspension de particules formées lors de la dilution dans de l'eau pouvant être facilement mise en suspension et résistant à la croissance de cristaux.
EP19920906371 1990-12-18 1991-10-22 Precipitated flowable concentrate formulations, their preparation and their agricultural uses Withdrawn EP0515679A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62929090A 1990-12-18 1990-12-18
US629290 1996-04-08

Publications (2)

Publication Number Publication Date
EP0515679A1 true EP0515679A1 (fr) 1992-12-02
EP0515679A4 EP0515679A4 (en) 1993-06-09

Family

ID=24522386

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920906371 Withdrawn EP0515679A4 (en) 1990-12-18 1991-10-22 Precipitated flowable concentrate formulations, their preparation and their agricultural uses

Country Status (6)

Country Link
EP (1) EP0515679A4 (fr)
JP (1) JPH05504362A (fr)
AU (1) AU1415092A (fr)
BR (1) BR9106407A (fr)
CA (1) CA2075920A1 (fr)
WO (1) WO1992010937A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1054116C (zh) * 1992-10-02 2000-07-05 生物技术资源两合公司 用作硫酸盐还原菌产生硫化物的抑制剂的细分散蒽醌类制剂
GB0126144D0 (en) * 2001-10-31 2002-01-02 Syngenta Ltd Pesticidal formulations
IL160858A (en) * 2004-03-14 2015-09-24 Adama Makhteshim Ltd Nano-pesticide pesticide preparation and process for preparation
TW200605783A (en) 2004-07-06 2006-02-16 Basf Ag Liquid pesticide compositions
IL290103B1 (en) 2019-08-05 2024-10-01 Ishihara Sangyo Kaisha Agricultural formulation

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2351363A1 (de) * 1972-10-13 1974-05-02 Rentokil Ltd Verfahren zur herstellung von festen partikelchen
GB2041751A (en) * 1979-02-05 1980-09-17 Montedison Spa Herbicidal compositions containing N min -alkoxy-N min -alkyl substituted N-phenylureas
EP0090178A1 (fr) * 1982-03-09 1983-10-05 Bayer Ag Formulations pesticides
EP0103171A1 (fr) * 1982-08-13 1984-03-21 Nissan Chemical Industries Ltd. Concentré en forme de suspension pour la lutte contre les mauvaises herbes
EP0205821A1 (fr) * 1985-05-02 1986-12-30 The Dow Chemical Company Dérivés halogéno-alkoxy-anilidés d'acides (hétérocyclyloxy-4 phénoxy)-2 alcanoiques et leur application comme herbicides
DE3540360A1 (de) * 1985-11-14 1987-05-21 Bayer Ag Herbizide mittel enhaltend photosynthesehemmer-herbizide in kombination mit pivalinsaeureamiden
EP0253374A1 (fr) * 1982-07-07 1988-01-20 Agan Chemical Manufacturers Ltd. Procédé pour combattre le vulpin dans les cultures des céréales et compositions y relatives
WO1989000380A1 (fr) * 1987-07-16 1989-01-26 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Composition phytosanitaire

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060084A (en) * 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3948636A (en) * 1972-11-09 1976-04-06 Diamond Shamrock Corporation Flowable aqueous composition of water-insoluble pesticide
US4348385A (en) * 1980-11-17 1982-09-07 Mobay Chemical Corporation Flowable pesticides
US4968343A (en) * 1985-09-16 1990-11-06 The Dow Chemical Company Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2351363A1 (de) * 1972-10-13 1974-05-02 Rentokil Ltd Verfahren zur herstellung von festen partikelchen
GB2041751A (en) * 1979-02-05 1980-09-17 Montedison Spa Herbicidal compositions containing N min -alkoxy-N min -alkyl substituted N-phenylureas
EP0090178A1 (fr) * 1982-03-09 1983-10-05 Bayer Ag Formulations pesticides
EP0253374A1 (fr) * 1982-07-07 1988-01-20 Agan Chemical Manufacturers Ltd. Procédé pour combattre le vulpin dans les cultures des céréales et compositions y relatives
EP0103171A1 (fr) * 1982-08-13 1984-03-21 Nissan Chemical Industries Ltd. Concentré en forme de suspension pour la lutte contre les mauvaises herbes
EP0205821A1 (fr) * 1985-05-02 1986-12-30 The Dow Chemical Company Dérivés halogéno-alkoxy-anilidés d'acides (hétérocyclyloxy-4 phénoxy)-2 alcanoiques et leur application comme herbicides
DE3540360A1 (de) * 1985-11-14 1987-05-21 Bayer Ag Herbizide mittel enhaltend photosynthesehemmer-herbizide in kombination mit pivalinsaeureamiden
WO1989000380A1 (fr) * 1987-07-16 1989-01-26 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Composition phytosanitaire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9210937A1 *

Also Published As

Publication number Publication date
BR9106407A (pt) 1993-05-18
CA2075920A1 (fr) 1992-06-19
AU1415092A (en) 1992-07-22
EP0515679A4 (en) 1993-06-09
JPH05504362A (ja) 1993-07-08
WO1992010937A1 (fr) 1992-07-09

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