EP0984682A4 - Compositions pesticides a liberation regulee - Google Patents

Compositions pesticides a liberation regulee

Info

Publication number
EP0984682A4
EP0984682A4 EP98916655A EP98916655A EP0984682A4 EP 0984682 A4 EP0984682 A4 EP 0984682A4 EP 98916655 A EP98916655 A EP 98916655A EP 98916655 A EP98916655 A EP 98916655A EP 0984682 A4 EP0984682 A4 EP 0984682A4
Authority
EP
European Patent Office
Prior art keywords
soil
protectant
granules
pesticidal
controlled release
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Withdrawn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
EP98916655A
Other languages
German (de)
English (en)
Other versions
EP0984682A1 (fr
Inventor
Mirsad Ahmetagic
Keith John Chandler
Thomas Peter Anderson
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.)
Crop Care Australasia Pty Ltd
Bureau of Sugar Experiment Stations
Original Assignee
Crop Care Australasia Pty Ltd
Bureau of Sugar Experiment Stations
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 Crop Care Australasia Pty Ltd, Bureau of Sugar Experiment Stations filed Critical Crop Care Australasia Pty Ltd
Publication of EP0984682A1 publication Critical patent/EP0984682A1/fr
Publication of EP0984682A4 publication Critical patent/EP0984682A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K17/00—Soil-conditioning materials or soil-stabilising materials
    • C09K17/14—Soil-conditioning materials or soil-stabilising materials containing organic compounds only
    • C09K17/16—Soil-conditioning materials or soil-stabilising materials containing organic compounds only applied in a physical form other than a solution or a grout, e.g. as platelets or granules
    • 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
    • A01N25/12—Powders or granules
    • 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
    • A01N25/22—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 ingredients stabilising the active ingredients
    • 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
    • A01N25/26—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 in coated particulate form
    • 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
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals

Definitions

  • This invention relates to pesticidal controlled release compositions. More particularly it relates to such compositions containing a pesticidal active ingredient and which are in the form of granules or pellets and intended for soil application.
  • Controlled release (CR) formulations that include pesticidal active ingredients are well known. They are commonly used for agricultural applications but may also be used for non agricultural applications. These CR formulations typically allow the continuous release of the active ingredient over a period of time to enable efficacious levels of pesticide to be available against the target species over a period of time. However, some CR formulations allow the release of the active ingredient at a non uniform rate and in some cases there may be periods of time when no active is released as well as periods of time where large amounts of active ingredient are released. In this specification all such formulations are regarded as CR formulations.
  • the pesticidal active ingredients include insecticides, fungicides, herbicides and growth regulators. They may also include microorganisms as the active ingredient.
  • CR formulations for soil application are known and typically consist of a pesticide, synthetic polymer, fillers and control release agents and are in the form of pellets or granules.
  • the formulations may alternatively comprise naturally occurring polymers rather than synthetic polymers and in some cases the polymers may be replaced with other organic or inorganic materials.
  • These formulations are very effective in most soils. However they may suffer from a number of deficiencies when applied in difficult or aggressive soils such as those with pH above 6.0 or those containing high levels of microbes. Difficult or aggressive soils are soils which can result in less than efficacious levels of the pesticide being maintained in the soil over the desired time period.
  • CR granules or pellets continually replenish the pesticidal active ingredient in the soil zone immediately surrounding the granule as the released active ingredient dissipates.
  • An effective concentration of pesticide active ingredient is required to be maintained to control the target pest.
  • the degradation mechanism in the soil can influence the equilibrium state and accelerate the release of active ingredient from the granule and result in premature depletion of the active ingredient from the granule. Accordingly, the concentration of pesticidal active ingredient in the soil may be insufficient to control the pest for the desired length of time.
  • this invention provides in one form a pesticidal controlled release granular formulation for soil application comprising a matrix and a pesticidal active ingredient wherein the formulation further comprises a protectant that in use is able to modify the soil properties in proximity to the granule such that the active ingredient is not adversely degraded when released into the soil.
  • the matrix is polymeric.
  • the protectant comprises a material that reduces the alkalinity or increases the acidity of the soil in proximity to the granules.
  • the protectant is a material which may generate hydrogen ions in the presence of soil in proximity to the granules.
  • the protectant is a coating of sulfur bound to the surface of the granules and wherein the coating is 1 - 80% by weight of the total composition.
  • the protectant is a fatty acid distributed throughout the granule.
  • the protectant is a biologically active compound that influences the microbial and/or the microflora population in proximity to the granule.
  • the protectant is a combination of one or more of a sulfur coating, fatty acid preferably distributed throughout the granule or a biologically active compound that influences the microbial and/or the microflora population in proximity to the granule.
  • Examples of protectants which may be used in this invention include fatty acids, sulfur, ammonium sulfate, citric acid or other organic or inorganic acids or acidic salts or mixtures thereof.
  • the protectant is normally selected so as to have low mobility in the soil. This can be achieved by the protectant having low water solubility or by of the protectant being able to absorb onto the soil particles.
  • the protectant should preferably be compatible with the polymeric matrix so as to form a stable non or low blooming product.
  • the protectant is selected so as to not substantially adversely degrade or interfere with the pesticidal properties of the active ingredient.
  • the fatty acids suitable for this invention can have a range of carbon chain length of C 8 - C 20 and can be saturated or unsaturated. Examples include stearic acid and palmitic acid.
  • controlled release pesticidal compositions of this invention may be prepared using a number of methods. These include, but are not limited to:
  • the granule ingredients including a protectant are premixed.
  • the mixture is then extruded and pelletised by conventional pelletising processes such as strand pelletising or die face pelletising in air or underwater.
  • the polymer, additives, fillers and protectant are usually individually metered to the extruder by gravimetric feeders, mixed and melted and then extruded through the extruder dies.
  • Liquid pesticidal active ingredients such as molten chlorpyrifos may be injected into the extruder via a metering pump.
  • This latter technique is particulariy suitable for incorporation of high melting point powdered protectants such as sulfur or citric acid.
  • the pesticide is soluble or compatible with the protectant such as chlorpyrifos and fatty acids, then the pesticide and the protectant can be mixed and injected into the extruder as a liquid via a metering pump at elevated temperature if necessary.
  • the extrudate can then be pelletised with the die face process or strand pelletising process.
  • the protectant is incorporated by post extrusion infusion into controlled release pellets or granules at elevated temperature and under mixing. This method is particularly suitable for liquid or low melting point protectants such as fatty acids.
  • Controlled release granules, containing active ingredient are coated with a protectant by using a bonding agent to improve the adherence of the coating to the granule.
  • This method is particularly suitable for the incorporation of high melting point powdered protectants such as sulfur which are insoluble in water.
  • a protectant may be incorporated into finely divided polymer in a high speed mixer and further mixed with other ingredients such as additives and fillers.
  • the mixture is then fed into an extruder barrel, while the pesticidal active ingredient such as chlorpyrifos is fed as a liquid at elevated temperature, for example 60°C, via a metering pump.
  • the tank, pump and transfer line may sometimes need to be heated.
  • the extrudate can then be pelletised as in method 1.
  • protectants may be incorporated by one of the following two further methods that involve coating the granules.
  • Controlled release granules containing a liquid protectant are first prepared as per method 1 or 2 and then coated as in method 3 with the second protectant.
  • a first protectant is used with a preferable melting point 50 - 80°C such as organic fatty acids as a bonding agent and a second protectant with high melting point is bonded to the granule by the bonding agent.
  • Suitable protectants act by lowering the soil pH in proximity to the granule to pH conditions where hydrolysis or degradation of the active ingredient is slowed or reduced.
  • Suitable protectants may be inorganic or organic acids or material selected to reduce the soil pH via either a buffering or neutralising action. They may also be materials which in the soil environment generate hydrogen ions via actions of soil microbes on the material. It is believed in the case of certain protectants that they may alternatively also act by reducing microflora or microfauna populations in proximity to the granule and this may take place without the necessity for pH modification. Examples of suitable protectants for this alternate mechanism include fungicides, bacteriastat or soil sterilants. A combined mechanism of pH modification and change in microbial population may take place in some cases.
  • the need for the present invention is based on the observation that existing CR formulations release pesticide at different rates and over differing periods of time in soils with different pH.
  • a CR formulation containing chlorpyrifos continues to release active ingredient over a three year period of time in soils with pH ⁇ 6.0, but the same CR formulation releases active ingredient for only 6 - 8 months in soils with pH > 7.0.
  • concentration of chlorpyrifos in soil with pH ⁇ 6.0 is much higher than the concentration of chlorpyrifos in soil with pH > 7.0 at the same period to time, eg three months, even though much more of the active ingredient had been released from the granules in the pH > 7.0 soil.
  • suitable organic acids vary in physical properties from liquid, semi solid and solid at ambient temperature.
  • the effectiveness of organic acids as protectants may depend on their chemical and physical properties as well as the type of granule matrix.
  • suitable organic acids and matrix the release rate of the protectant from the granule may be adjusted to be similar to that of the pesticidal active ingredient, eg chlorpyrifos.
  • organic acids can be incorporated by using method 1 , method 2, or method 3 in an amount from about 0.5-50wt. %, preferably between 3 to 25 wt. % of the total CR granule formulation; pesticide in an amount between about 0.1 - 50 wt. %, preferably between about 3 and about 20 wt. %;
  • the matrix material for the granule may be a synthetic polymer as for example with poly vinyl chloride or poly(ethylene-vinyl acetate) copolymer and/or a natural or modified natural polymer as for example with starch.
  • the matrix should be from 5 - 90% and when the matrix is polymeric consist of synthetic, natural polymers or mixtures thereof; each of the synthetic and natural polymers are present in an amount between about 0 - 90 wt. %, preferably between about 20 and about 80 wt. %;
  • the polymers may be thermoplastic or thermoset.
  • Inorganic fillers such as inorganic salts such as ammonium sulfate and sodium sulfate, mineral fillers such as clays and calcium carbonate in an amount between about 0 - 80 wt. %, preferably between about 5 and about 60 wt.
  • processing additives such as plasticisers, stabilisers and lubricants in an amount between about 0 - 30 wt. %, preferably between about 1 and about 10 wt. %.
  • processing additives such as plasticisers, stabilisers and lubricants in an amount between about 0 - 30 wt. %, preferably between about 1 and about 10 wt. %.
  • Other additives such as colorants and solvents may be incorporated without substantially changing the efficacious properties of the granules.
  • Sulfur is a particular preferred protectant. In the form of a powder it is practically insoluble in water. It is believed soil microorganisms convert the sulfur to sulphuric acid. As sulfur is released from CR granules at very low rates there may be insufficient acid formed in the soil to lower the high soil pH. It has been found that generally better results can be achieved by coating the granules with sulfur rather than having it uniformly distributed throughout the granule. Sulfur may be incorporated by using method 3, as described above, in an amount between about 1 - 80 wt. % of the final product and more preferably between about 30 and 80 wt. %.
  • the bonding agents for the coating process may be chosen from a wide range of known materials including acrylic film forming emulsions at amounts typically between about 0.5 and 10 wt. % and, preferably between about 1 and 2 wt. %; polyvinyl alcohol in an amount preferably between 0.5 - 10 wt. %, and preferably between about 1 and 5 wt. %; pre-treatment additives such as fine, inorganic fillers can be used in amounts up to about 1 wt. %, preferably between 0.1 and 0.5 wt. %.
  • compositions of this invention are most useful in difficult soil it has been found that in normal soils of pH ⁇ 6.0 the persistence of the pesticidal compositions of the present invention may be improved over prior art formulations.
  • Soils with particularly high pH, pH > 8, may require more than one protectant to give best results.
  • both organic fatty acids and sulfur may be incorporated into CR granules and method 6 may be the most suitable manufacturing method.
  • inorganic acids may also be used as protectants as well as bioactive agents such as fungicides, bacteriastats or soil sterilants. These latter protectants adjust the microbial levels in the soil. When both an organic acid and sulfur are used as protectants the level of sulfur is typically between about 1 and 80 wt.
  • the organic acid MP 50 - 80°C
  • polyvinyl alcohol as a final coating agent is used at an amount up to about 5 wt. %, preferably up to about 2 wt. %. All percentages are by weight and expressed in terms of the final product composition.
  • Controlled release chlorpyrifos granular formulations based on an EVA copolymer matrix were prepared by an extrusion process using the ingredients set out above the heading "FATTY ACIDS" in the table below .
  • the colour was a blue pigment dispersed in an EVA copolymer.
  • a strand pelletising process was used to produce cylindrical granules of diameter and length approximately 2mm.
  • the granules and each of the protectant fatty acids of the type and quantity set out in the table were placed in a ribbon blender and mixed at a temperature between 60°C and 80°C for about 45 minutes or until the granules became dry.
  • composition of the overall CR formulations in each of these Examples are set out in the table below.
  • a slurry of Perlite (0.2 parts) and an acrylic film forming emulsion (0.8 parts) was prepared by stirring.
  • the slurry (1.0 parts) was then blended slowly with the CR granules (46 parts) to coat the slurry evenly over the surface of the granules.
  • the coated granules were then dried at 25°C for approximately 10 minutes to allow the emulsion to coalesce and form a film.
  • These coated granules were then further coated with a 20% polyvinyl alcohol (88% hydrolysed) aqueous solution (4.4 parts).
  • Powdered sulfur (12.5 parts) was then added to the polyvinyl alcohol coated granules in a gentle blender until no free sulfur remained in the blender.
  • Example 5 the remaining powdered sulfur was then added in three equal amounts (12.5 parts) each as follows. A 10% polyvinyl (88% hydrolysed) aqueous alcohol solution (7 parts) was then added to the sulfur coated granules until they were quite damp but non clumping. A further portion (12.5 parts) of powdered sulfur was then added and the granules were coated again with a gentle tumbling action. This process was repeated two more times. The remaining portion of the 10% polyvinyl alcohol solution (5.2 parts) was added after the last portion of powdered sulfur had been mostly incorporated such that the granules were damp but not sticky.
  • the coated granules were then dried at 35°C to give granules of the following overall compositions (non-volatile content). This process was then repeated with appropriate adjustment of sulfur and polyvinyl alcohol levels to produce the granules in Example 6.
  • a CR chlorpyrifos formulation based on a PVC polymer and starch matrix was produced as in the first part of Example 1 except that an under water pelletising process was used to produce generally spherical granules of approximately 2mm diameter rather than the cylindrical granules of Example 1.
  • These granules were then coated with powdered sulfur by using fatty acids as the bonding agents. The fatty acid was first melted by heating and then applied as a coating to preheated granules with gentle agitation. Sulfur powder was then coated onto the granules by adding the sulfur gradually under gentle agitation. The sulfur coated granules were then cooled to room temperature.
  • Granules were prepared with chlorpyrifos as the active ingredient using the method as described in Example VI, Table XIV of US Patent 4400374. These CR granules were then coated as in Example 5 above with powdered sulfur using polyvinyl alcohol as the binder material at two coating levels to give granules which contained 27.5% sulfur by weight (Example 9) and 45.6% sulfur by weight (Example 10).
  • This Example shows the comparative testing of Examples 9 and 10 compared to conventional CR granules.
  • Samples of uncoated granules used to prepare the coated granules in Examples 9 and 10 were used as controls. Granule samples were then applied at a rate of 0.5g to1 OOg soil in duplicate to a silty loam soil with a pH of 7.5. Uncoated granules normally lose activity within 6 months in this soil and hence this soil is regarded as aggressive. Samples of the uncoated control were also added to the soil for comparison purposes with and without additions of sulfur to the soil (applied as a powdered form broadcast in the soil). The soil surrounding the granules was analysed for chlorpyrifos content 6 months after application and the following results were obtained. Granules according to the present invention, particularly at the higher sulfur level, led to much higher chlorpyrifos levels in the soil after 6 months.
  • Control An unmodified CR granule formulation, referred to as the "Control", was prepared as in Australian Patent No. 554,843 to produce granules with 14% w/w chlorpyrifos.
  • a commercial fatty acid blend pristerene having a minimum of 70% stearic acid was then infused into the granules according to the method in Example 1.
  • This Example illustrates the testing of Examples 12 - 14 compared to a control as described in Examples 12 - 14 above.
  • the release rate test was established in a controlled environment at a temperature of 30°C and watering regimes to obtain medium soil moisture (moisture level from 6% to 20% w/w.). Two soils prone to extremely rapid degradation of chlorpyrifos and one standard soil with a much lesser rate of chlorpyrifos degradation, were used for testing release rates of active ingredient from the granules and accumulation of chlorpyrifos in the soils.
  • Soil A was a silty loam with pH 7.4.
  • Soil B was a clay loam with pH 6.9 - 7.0.
  • the standard soil was a pale brown fine sandy loam with pH 5.3. The test was conducted in two replicates and four recovery periods, over six months as follows: 28 day, 56 day, 84 day and 168 day.
  • test sample was prepared by placing 50 grams of soil in a plastic container, followed by 60 granules of CR product and then another 50 grams of soil on top. A glass wool insert was then placed on top of the soil to prevent soil disturbance during watering and also prevent the rapid loss of moisture. The samples were watered initially with 20ml of water and then weekly with 14ml of water to maintain moisture levels from within the range of 6% to 20%.
  • the plastic containers were cylindrical and 120ml in volume (diameter 44 mm and height 108 mm), and had four holes for water drainage. A glass wool insert was placed at the bottom of each container to prevent soil escape.
  • the glass wool was removed from the top of the containers and soil left at 30°C for 3 - 4 days to dry sufficiently to permit sieving to separate the granules from the soil.
  • the granules were then analysed for chlorpyrifos and the soil samples analysed to determine total chlorpyrifos in the soil.
  • Results are set out below and expressed as micrograms of chlorpyrifos per granule ( ⁇ g Al per granule). Higher concentrations of Al in the soil are present for Examples 12, 13 and 14 in the aggressive soil and after 168 days.
  • This example illustrates the field trial performance of composition according to the present invention.
  • Example 11 was repeated in a field trial in another aggressive soil characterised as a coarse sandy-loam soil of pH 6.5 to 7.0 at Gordonvale.
  • the granules and soil were evaluated after nine and fifteen month intervals as in Example 15. The results are set out in the table below.
  • Coated granules from Examples 9 and 10 showed much higher levels of soil borne chlorpyrifos than the control after both 9 and 15 months.
  • the amount of chlorpyrifos in the granules was much higher in the coated granules than for the controls after both 9 and 15 months.
  • Example 16 was repeated in a further field trial in soil characterised as a red Kraznozem soil with pH was 6.1. The soil and granules were tested after nine and eighteen months as in Example 16 and the results are set out as follows.
  • Example 9 and 10 again showed both higher levels of chlorpyrifos in the granules as well as higher concentrations of chlorpyrifos in the soil after both 9 and 18 months. 9 Month 18 Months

Abstract

L'invention se rapporte à des pastilles ou granulés pesticides à libération régulée et contenant un phytoprotecteur. Ce phytoprotecteur modifie les concentrations du composant pesticide actif au voisinage des pastilles ou des granulés. Lesdites pastilles ou lesdits granulés sont destinés à être appliqués à des sols agressifs de même qu'à des sols normaux. Le pesticide préféré est un insecticide.
EP98916655A 1997-04-24 1998-04-24 Compositions pesticides a liberation regulee Withdrawn EP0984682A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPO6441A AUPO644197A0 (en) 1997-04-24 1997-04-24 Controlled release pesticidal compositions
AUPO644197 1997-04-24
PCT/AU1998/000299 WO1998048623A1 (fr) 1997-04-24 1998-04-24 Compositions pesticides a liberation regulee

Publications (2)

Publication Number Publication Date
EP0984682A1 EP0984682A1 (fr) 2000-03-15
EP0984682A4 true EP0984682A4 (fr) 2004-10-20

Family

ID=3800735

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98916655A Withdrawn EP0984682A4 (fr) 1997-04-24 1998-04-24 Compositions pesticides a liberation regulee

Country Status (6)

Country Link
EP (1) EP0984682A4 (fr)
AU (1) AUPO644197A0 (fr)
ID (1) ID24341A (fr)
NZ (1) NZ500150A (fr)
WO (1) WO1998048623A1 (fr)
ZA (1) ZA983505B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010121142A2 (fr) 2009-04-17 2010-10-21 Stratacor, Inc. Compositions pesticides pour insectes et arthropodes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3771994A (en) * 1970-06-25 1973-11-13 Ppg Industries Inc Method of controlling weeds with a combination of an organic herbicide and potassium azide
US4400374A (en) * 1979-06-22 1983-08-23 Environmental Chemicals, Inc. Controlled release of compounds utilizing a plastic matrix
EP0360663A1 (fr) * 1988-09-23 1990-03-28 Rhone-Poulenc Chimie Granules d'épendage et leur procédé de préparation
US4965254A (en) * 1985-02-14 1990-10-23 Bayer Aktiengesellschaft Agents for combating pests
WO1991003940A1 (fr) * 1989-09-15 1991-04-04 Goodman Fielder Wattie Australia Limited Matrices biodegradables de liberation regulee

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0676282B2 (ja) * 1985-05-29 1994-09-28 クミアイ化学工業株式会社 固状農薬組成物
AT392267B (de) * 1989-01-13 1991-02-25 Radex Heraklith Verfahren zur herstellung eines mittels zur bodenmelioration aus mgo und mbco3
AU630806B2 (en) * 1990-11-19 1992-11-05 Herbert Roy Bubb Liquid fertilizer incorporating deposit lime and methods for use
DE19510887A1 (de) * 1995-03-24 1996-09-26 Basf Ag Stabile Festformulierungen von Cyclohexenonoximether-Herbiziden

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3771994A (en) * 1970-06-25 1973-11-13 Ppg Industries Inc Method of controlling weeds with a combination of an organic herbicide and potassium azide
US4400374A (en) * 1979-06-22 1983-08-23 Environmental Chemicals, Inc. Controlled release of compounds utilizing a plastic matrix
US4965254A (en) * 1985-02-14 1990-10-23 Bayer Aktiengesellschaft Agents for combating pests
EP0360663A1 (fr) * 1988-09-23 1990-03-28 Rhone-Poulenc Chimie Granules d'épendage et leur procédé de préparation
WO1991003940A1 (fr) * 1989-09-15 1991-04-04 Goodman Fielder Wattie Australia Limited Matrices biodegradables de liberation regulee

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9848623A1 *

Also Published As

Publication number Publication date
ID24341A (id) 2000-07-13
WO1998048623A1 (fr) 1998-11-05
EP0984682A1 (fr) 2000-03-15
ZA983505B (en) 1998-10-30
AUPO644197A0 (en) 1997-05-22
NZ500150A (en) 2000-07-28

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