WO2003013248A1 - Procede de lutte contre les mauvaises herbes - Google Patents

Procede de lutte contre les mauvaises herbes Download PDF

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Publication number
WO2003013248A1
WO2003013248A1 PCT/EP2002/008321 EP0208321W WO03013248A1 WO 2003013248 A1 WO2003013248 A1 WO 2003013248A1 EP 0208321 W EP0208321 W EP 0208321W WO 03013248 A1 WO03013248 A1 WO 03013248A1
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WO
WIPO (PCT)
Prior art keywords
oxadiargyl
compositions
crop
locus
granules
Prior art date
Application number
PCT/EP2002/008321
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English (en)
Inventor
Sylvie Lavault
Original Assignee
Bayer Cropscience S.A.
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 Bayer Cropscience S.A. filed Critical Bayer Cropscience S.A.
Publication of WO2003013248A1 publication Critical patent/WO2003013248A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • This invention relates to a method for controlling the growth of weeds by the progressive release of oxadiargyl into the surface layer of a growing medium and to compositions for use in the method.
  • oxadiargyl which is for controlling weeds has been disclosed in, for example, Japanese Patent Application No. 61 297457.
  • this herbicide in the presence of certain antidotes is described in Japanese Patent Publication No. 97 132506.
  • Commercial formulations of oxadiargyl typically emulsion concentrates
  • Such a risk of phytotoxicity caused by oxadiargyl has lead to the routine application of commercial formulations of oxadiargyl with an antidote.
  • the dose rate of oxadiargyl can be maintained in the growing medium, for example, during the period from application of oxadiargyl to establishment of a crop. It has been found that by maintaining a uniform concentration of oxadiargyl in the growing medium, during the period from application of the oxadiargyl to establishment of a crop, improved crop selectivity may be obtained. Furthermore, herbicidal efficacy may be improved.
  • the present invention provides a method for controlling the growth of weeds at a locus in a growing medium, which comprises treating the locus with a delayed- release composition comprising oxadiargyl to provide progressive release of oxadiargyl herbicide into the growing medium.
  • the growing medium includes composts, preferably soil, which may be substantially covered by an aqueous layer, which may or may not contain particulate organic matter.
  • the locus is preferably a crop-growing locus, typically where a crop is sown and cultivated, for example a paddy field.
  • the method comprises applying to the locus, for example where the crop is sown and cultivated, sequential low doses of oxadiargyl.
  • a delayed release composition comprising oxadiargyl.
  • the delayed release composition which constitutes a feature of the invention, may comprise, for example, an encapsulated composition comprising oxadiargyl itself or a composition containing it.
  • the delayed release compositions may be prepared by known methods.
  • the encapsulated product may have a solid, outer wall, said wall comprising an inert material (a protective coating), generally having no substantial herbicidal activity.
  • the encapsulated product according to the present invention may comprise granules comprising oxadiargyl, each of these granules being encapsulated with a solid film comprising an inert protective coating material itself having no substantial herbicidal activity.
  • the coating material is made from at least a barrier material and a surface active agent and/or plasticizer. The combination of both types of material result in the production of encapsulations which are capable of providing the required release properties.
  • barrier materials which may be selected from, and are not limited to, the following : fatty acids, polyglycerol esters of fatty acids, monoglycerides, diglycerides, gelatins, starches derived from corn, wheat, potato or milo vegetables, zein proteins, sucroesters, sucroglycerides, cellulose ethers, cellulose esters, chitin, chitosan, amylopectin or hydrocolloids and mixtures thereof.
  • Specific barrier materials include the following generic materials, along with, where appropriate, trade names that the materials are presently sold under: glyceryl esters of long chain fatty acids such as glyceryl monopalmitostearate (Geleol - Gattefosse Company), glyceryl palmitostearate (Biogapress - Gattefosse Company) and (Plurol WL1009 - Gattefosse Company); acetylated monoglycerides such as monoacetylated monoglycerides (Myvacet 5-07 - Eastman Kodak Company); hemisynthetic glycerides (Suppocire A and Suppocire D - Gattefosse Company); sucroglycerides derived from fatty oils such as coprah oil (Celynol LMO - Rhone- Poulenc SA), palm oil (Clynol MSPO 11 - Rhone Poulenc SA), and hydrogenated soybean oil and palm oil; cellulose acetate phthalate (Aqua
  • gelatin particularly preferred is the use of gelatin, chitosan, stearic acid and glyceryl monopalmitostearate.
  • the other component of the coating is a surface active agent or plasticizer material.
  • These materials can function to reduce the thickness and provide flexibility to the coating material when applied to oxadiargyl and thereby enable the production of a controlled release material.
  • the key criteria to be considered when selecting such materials is that they provide an optimally sized coating.
  • the surface active agent functions to provide a uniformly distributed layer of the coating material to produce a strong thin coating
  • the plasticizer functions to help provide coatings which are thin, strong and do not easily break.
  • Particularly preferred is the use of both surface active agents and plasticizer materials.
  • Examples of surface active agents which may be selected include the following: sucroesters, sucroglycerides, propylene glycol monoesters, ethoxylated monoglycerides, ethoxylated diglycerides, glycerol lacto esters of fatty acids, lecithin, polyoxyethylene sorbitan esters, sorbitan esters of fatty acids, stearoyl-2-lactylate, polyoxyethylene esters of fatty acids such as stearic acid, acetylated monoglycerides and mixtures thereof.
  • sucroesters polyoxyethylene sorbitan esters, specifically polyoxyethylene sorbate monooleate and mixtures thereof.
  • Sucroester 7 from the Gattefosse Company (sucrose distearate) and Tween 80 (polyoxyethylene sorbate monooleate).
  • Tween 80 polyoxyethylene sorbate monooleate
  • barrier materials particularly the sucroesters can additionally function as the surface active agents.
  • Other materials which have multiple functions include mono and diglycerides, polyoxyethylene esters of long chain fatty acids such as polyoxyethylene sorbate monooleate, sorbitan monoesters of long chain fatty acids and gelatins.
  • Preferred plasticizers include acetyl tributyl citrate (Citroflex A4), acetyl triethyl citrate (Citroflex A2), tricalcium phosphate, dicalcium phosphate or diethylphthalate and mixtures thereof. These materials function to produce very thin coatings, i.e., the entire coating comprising no more than from 2 to 10 percent by weight of the entire core material.
  • the barrier material is between from 80 to 100 percent by weight of the coating material, more preferably between from 90 to 95 percent by weight of the coating material.
  • the coating typically has a thickness ranging between from 3 to 20 microns, more preferably between from 5 to 10 microns.
  • any method which is commonly used to encapsulate herbicide materials may be selected.
  • examples of such methods include fluidized bed coating, coacervation, interfacial polycondensation polymerization, spray coating, pan coating or solvent film coating. Particularly preferred is the use of fluidized bed coating.
  • the oxadiargyl typically in the form of a powder is placed in a fluidized bed apparatus, (e.g. GLATT GPC G1 ) preferably equipped with top or bottom spray nozzles.
  • a dispersion containing the coating material is then pumped into and atomised in the apparatus on the fluidized particle bed, typically by a hot air current.
  • the solvent used to form the coating dispersion is typically water, although other solvents such as alcohols and glycols could be used.
  • the application of the dispersion to the powder typically takes from 15 to 240 minutes, depending on the thickness of the coating film desired.
  • the coated material powder is then dried, typically from 1 to 60 minutes, resulting in the production of a coating of the coating material onto all external surfaces of the oxadiargyl.
  • the core does not react with the coating and therefore, two discrete phases (e.g., core/shell particle morphology) are produced.
  • the granules of encapsulated oxadiargyl according to the present invention may be for example, in a powdered state or in a liquid or solid formulation, in association with an agriculturally acceptable diluent or carrier.
  • compositions of the present invention provide a method for controlling the release of a herbicide in a range of soil types and edaphic conditions by modification of the ratios of oxadiargyl : carrier material, in order to achieve the most favourable release rates for optimal efficacy and selectivity.
  • compositions of the present invention provide a method for reducing the release rate of herbicides, such as oxadiargyl, in soil thereby slowing the overall rate of degradation.
  • Encapsulation in a matrix carrier increases the stability of the herbicide as it is protected from the components which may promote degradation, such as moisture or microbial activity.
  • pre-emergence application is meant an application to the soil in which the weed seeds or seedlings are present before emergence of the crop.
  • pre-emergence application is known as "pre-plant incorporated” (PPI), where the herbicide is incorporated into the soil before planting the crop. Another is where the herbicide is applied to the soil surface after sowing the crop.
  • foliar activity is meant herbicidal activity produced by application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil.
  • the application rate of oxadiargyl in compositions of the present invention is from 0.05 kg to 0.150 kg herbicidally active compound, preferably from 0.05 kg to 0.075 kg herbicidally active compound per hectare.
  • compositions of the invention are generally applied to a locus pre-emergence of the weeds and crop plant, or early post-emergence. Preferably the compositions of the invention are applied pre-emergence.
  • compositions suitable for herbicidal use in the method of the invention comprising oxadiargyl (which may be encapsulated as hereinbefore described), in association with, and preferably homogeneously dispersed in, one or more compatible agriculturally-acceptable diluents or carrier and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use on herbicidal compositions and which are compatible with oxadiargyl].
  • the term "homogeneously dispersed” is used to include compositions in which oxadiargyl is dissolved in other components.
  • herbicidal compositions is used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use.
  • the compositions contain from 0.05 to 90% by weight of oxadiargyl.
  • the herbicidal compositions may contain both a diluent or carrier and surface-active (e.g. wetting, dispersing, or emulsifying) agent.
  • Surface-active agents which may be present in herbicidal compositions of the present invention may be of the ionic or non-ionic types, for example sulpho cinoleates, quaternary ammonium derivatives, products based on condensates of ethythene oxide with alkyl and polyaryl phenols, e.g.
  • nonyl- or octyl-phenols tristyryl phenols, condensates of ethylene oxide with alcohols, or carboxylic acid esters of anyhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dinonyl- and dioctyl-sodium sulphonosuccinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignosulphonates and sodium and calcium alkylbenzene sulphonates.
  • the herbicidal compositions according to the present invention may comprise up to 10% by weight, e.g. from 0.05% to 10% by weight, of surface-active agent but, if desired, herbicidal compositions according to the present invention may comprise higher portions of surface-active agent, for example up to 15% by weight in liquid emulsifiable suspension concentrates and up to 25% by weight in liquid water soluble concentrates.
  • suitable solid diluents or carriers are aluminium silicate, microfine silicon dioxide, talc, chalk, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin, attapulgite, diatomaceous earth, mica, alumina oxide, titanium oxide and bentonite.
  • the solid compositions are preferably prepared by grinding oxadiargyl with solid diluents or by impregnating the solid diluents or carriers with solutions of oxadiargyl in volatile solvents, evaporating the solvents and if necessary, grinding the products so as to obtain powders.
  • Granular formulations may be prepared by absorbing the oxadiargyl dissolved in suitable solvents, (which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating compositions in powder form obtained as described above.
  • Solid herbicidal compositions, particularly wettable powders and granules may contain wetting or dispersing agents (for example of the types described above), which may also, when solid, serve as diluents or carriers.
  • Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions which may incorporate a surface-active agent.
  • Suitable liquid diluents for incorporation in the liquid compositions include water, glycols, glycol ethers, tetrahydrofurfuyl alcohol, acetophenone, cyclohexanone, isophorone, alkyl pyrrolidones, butylolactone, chlorinated toluene, xylene, mineral, animal and vegetable oils, esterified vegetable oils and light aromatic and naphthenic fractions of petroleum (and mixtures of these diluents).
  • Surface-active agents, which may be present in the liquid compositions may be ionic or non-ionic (for example of the types described above) and may, when liquid, also serve as diluents or carriers.
  • Powders, dispersible granules and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • suitable diluents for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • liquid compositions of oxadiargyl may be used in the form of self- emulsifying concentrates containing the active substances dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of such concentrates to water producing compositions ready for use.
  • Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic spray technique.
  • Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, spreading agents, stabilisers, buffers, sequestering agents, anti- caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.
  • Preferred herbicidal compositions according to the present invention are encapsulations containing water dispersible granules which comprise from 1 to 90%, e.g. 25 to 75% of oxadiargyl, from 1 to 15%, e.g. 2 to 10%, of surface-active agent and from 5 to 95%, e.g. 20 to 60%, of solid diluent, e.g.
  • aqueous suspension concentrates which comprise from 5 to 70% of oxadiargyl, from 2 to 10% of surface-active agent, from 0.1 to 5% of thickener and from 15 to 87.9% of water; wettable powders which comprise from 5 to 90% of oxadiargyl, from 2 to 10% of surface-active agent and from 8 to 88% of solid diluent or carrier; water soluble or water dispersible powders which comprise from 5 to 90% of oxadiargyl, from 2 to 40% of sodium carbonate and from 0 to 88% of solid diluent; liquid water soluble concentrates which comprise from 5 to 50%, e.g. 10 to 30% of oxadiargyl, from 0 to 25% of surface-active agent and from 10 to 90%, e.g. 45 to
  • liquid emulsifiable suspension concentrates which comprise from 5 to 70% of oxadiargyl from 5 to 15% of surface-active agent, from 0.1 to 5% of thickener and from 10 to 84% of organic solvent, e.g. mineral oil; and emulsifiable concentrates which comprise 0.05 to 90%, and preferably from 1 to
  • the water dispersible granules comprising oxadiargyl have a particle size of generally 10-2000 ⁇ m, preferably 300-1500 ⁇ m.
  • Herbicidal compositions according to the present invention may also comprise oxadiargyl in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.
  • herbicidally active compounds examples include herbicides, for example to increase the range of weed species controlled, for example those listed in the Pesticide Manual 11 th Edition (British Crop Protection
  • Pesticidally active compounds and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example those hereinbefore mentioned, and which are acids, may, if desired, be utilised in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • Example C1 illustrate herbicidal compositions which may be used for the purpose of comparison in the present invention.
  • Example C1 illustrate herbicidal compositions which may be used for the purpose of comparison in the present invention.
  • An emulsifiable concentrate is formed from:
  • NMP N-Methylpyrrolidinone
  • Aromatic solvent to 100 volumes by stirring NMP, oxadiargyl, CaDDBS, NPEOPO and Aromatic solvent until a clear solution is formed, and adjusting to volume with Aromatic solvent.
  • a wettable powder is formed from:
  • a suspension concentrate is formed from:
  • a water dispersible granule is formed from:
  • Binder (Sodium lignosulphonate) 8% w/w china clay 30% w/w
  • Microfine silicon dioxide 3% w/w by blending the above ingredients together, grinding the mixture in an air jet mill and granulating by addition of water in a suitable granulation plant (e.g. Fluid bed drier) and drying.
  • a suitable granulation plant e.g. Fluid bed drier
  • the active ingredient may be ground either on its own or admixed with some or all of the other ingredients.
  • compositions comprising 0.15ppm oxadiargyl were prepared and their stability in water analysed.
  • the formulations were placed in petri dishes (with a depth of 3cm), sealed to prevent any solvent loss; stored at 25°C for the specified length of time then sampled (at a depth of 1cm) and analysed.
  • the method of analysis was as follows. Each formulation mixture was analysed for the proportion of oxadiargyl released into water using standard High Performance Liquid Chromatography (HPLC) technology.
  • HPLC High Performance Liquid Chromatography
  • WG represents a wettable granule formulation
  • EC represents the commercial emulsifiable concentrate formulation "RaftTM”.
  • Different profiles of the release of oxadiargyl from wettable granules and emulsifiable concentrates were obtained.
  • the release of uniform concentrations of oxadiargyl from the WG formulation was observed from 1 to 288 hours.
  • oxadiargyl from the EC formulation appeared to be concentrated within the top 1cm of the water surface (the sampling point) initially, decreasing gradually over time. [Such high concentrations located within the surface layer of water may cause phytotoxicity in developing rice plants].
  • M 0 represents the initial weight of the granules
  • Mi represents the weight of non-disintegrated granules
  • Example 2 The experimental protocol as described in Example 1 was conducted using wettable granule formulations with different coatings or containing different binding agents (as defined in Example 2). The amount of oxadiargyl released from the formulations into solution was determined at several time intervals.
  • Echinochloa oryzicola, (ECHOR), Monochoria vaginalis (MOOVA) and Scirpus juncoides (SCPJU) were sown and formulations of oxadiargyl (as described in Example 2) applied at 6.3, 12.5, 25, 50, 75, 100 and 200g per hectare, five days after sowing.
  • the efficacy of the oxadiargyl formulations on the weed species was observed 18 days after treatment and is expressed as percentage leaf sheath browning in the following tables:-
  • EC represents the commercial emulsifiable concentrate formulation, "RaftTM”.
  • Seeds of transplanted rice were sown in compost in a glasshouse with supplementary illumination (14 hours).
  • Rice plants were transplanted into paddy pots containing puddled light clay (organic matter 1 %, clay 29.0%, sand 30.0%, silt 40.0%, pH 6.9).
  • 5 days after sowing the paddies were treated with oxadiargyl formulations at 6.3, 12.5 and 25g per hectare.
  • the paddies were watered as necessary and the rice visually assessed for the percentage reduction in growth 5, 7 and 18 DAT.
  • compositions of the present invention show good selectivity on transplanted rice from 5 to 18 DAT and at high application rates compared to the commercial EC formulation.
  • ORYSA transplanted rice
  • Echinochloa oryzicola Echinochloa oryzicola
  • MOOVA Monochoria vaginalis
  • LIDPY Lindernia Pyxidaria
  • compositions of the present invention show good efficacy on ECHOR, MOOVA and LIDPY and are selective on transplanted rice.

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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)
  • Catching Or Destruction (AREA)

Abstract

La présente invention concerne un procédé de lutte contre les mauvaises herbes à un certain endroit d'un milieu de culture, ce procédé consistant à traiter l'endroit avec une composition herbicide à action retardée contenant de l'oxadiargyl qui libère progressivement l'herbicide oxadiargyl dans le milieu de culture.
PCT/EP2002/008321 2001-08-08 2002-07-26 Procede de lutte contre les mauvaises herbes WO2003013248A1 (fr)

Applications Claiming Priority (2)

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EP01420182.6 2001-08-08
EP01420182 2001-08-08

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WO2003013248A1 true WO2003013248A1 (fr) 2003-02-20

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106165689A (zh) * 2016-07-07 2016-11-30 佛山市盈辉作物科学有限公司 二氯喹啉草酮与丙炔噁草酮的除草组合物
CN111226953A (zh) * 2020-03-08 2020-06-05 安徽喜田生物科技有限公司 一种含有丙炔噁草酮和西草净的除草组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818026A (en) * 1971-06-02 1974-06-18 Rhone Poulenc Sa 3-(2,4-dichloro-5-propargyloxy-phenyl) oxadiazolone derivatives useful as herbicides
WO1988004653A1 (fr) * 1986-12-16 1988-06-30 Showa Rhodia Chemicals Kabushiki Kaisha Derive d'oxadiazolone, procede de production et herbicide le contenant
EP0364601A1 (fr) * 1988-03-03 1990-04-25 Hokko Chemical Industry Co. Ltd. Agent conferant des proprietes de liberation entretenue a des substances chimiques utilisees en agriculture, substances chimiques a liberation entretenue et procede de production
JPH09132506A (ja) * 1995-09-05 1997-05-20 Rhone Poulenc Agrochim 水田用除草剤組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818026A (en) * 1971-06-02 1974-06-18 Rhone Poulenc Sa 3-(2,4-dichloro-5-propargyloxy-phenyl) oxadiazolone derivatives useful as herbicides
WO1988004653A1 (fr) * 1986-12-16 1988-06-30 Showa Rhodia Chemicals Kabushiki Kaisha Derive d'oxadiazolone, procede de production et herbicide le contenant
EP0364601A1 (fr) * 1988-03-03 1990-04-25 Hokko Chemical Industry Co. Ltd. Agent conferant des proprietes de liberation entretenue a des substances chimiques utilisees en agriculture, substances chimiques a liberation entretenue et procede de production
JPH09132506A (ja) * 1995-09-05 1997-05-20 Rhone Poulenc Agrochim 水田用除草剤組成物

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Title
DATABASE WPI Section Ch Week 199730, Derwent World Patents Index; Class C02, AN 1997-328435, XP002187258 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106165689A (zh) * 2016-07-07 2016-11-30 佛山市盈辉作物科学有限公司 二氯喹啉草酮与丙炔噁草酮的除草组合物
CN111226953A (zh) * 2020-03-08 2020-06-05 安徽喜田生物科技有限公司 一种含有丙炔噁草酮和西草净的除草组合物

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