WO2003075658A1 - Nematicides encapsules - Google Patents

Nematicides encapsules Download PDF

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Publication number
WO2003075658A1
WO2003075658A1 PCT/IL2003/000141 IL0300141W WO03075658A1 WO 2003075658 A1 WO2003075658 A1 WO 2003075658A1 IL 0300141 W IL0300141 W IL 0300141W WO 03075658 A1 WO03075658 A1 WO 03075658A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurea
organophosphorus
encapsulated
nematocide
microencapsulated
Prior art date
Application number
PCT/IL2003/000141
Other languages
English (en)
Inventor
Arie Markus
Original Assignee
B.G. Negev Technologies And Applications Ltd.
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 B.G. Negev Technologies And Applications Ltd. filed Critical B.G. Negev Technologies And Applications Ltd.
Priority to AU2003209627A priority Critical patent/AU2003209627A1/en
Publication of WO2003075658A1 publication Critical patent/WO2003075658A1/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
    • 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
    • A01N25/28—Microcapsules or nanocapsules
    • 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
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the present invention relates to microencapsulated nematocides that are non-soluble in aqueous solutions and to methods for the preparation thereof. More specifically the present invention relates to nematocides that are non-soluble in aqueous solutions and especially to organophosphorus nematocides encapsulated in a polyurea microcapsule shell having a diameter of between about 10 and 50 microns.
  • an organophosphorus nematocide encapsulated in a polyurea microcapsule shell in combination with an acid.
  • Mocap ethoprophos
  • ethoprophos is an organophosphorus non-systemic nematocide with contact action. It is designed for direct application to the soil and is distributed commercially as an emulsified concentrate, in organic solvent. Its chemical formulation is as follows:
  • Mocap has instability in the soil over long periods of time. It retains its activity for about 87 days in humus-containing soil with pH of 4.5 and for only about 14-28 days in sandy loam soil with pH of 7.2-7.3. Another major problem is that when Mocap is applied to the soil in the formulation currently available, the active ingredient leaches down below the water table and contaminates the ground water, which becomes unfit for use. Microencapsulation provides a solution to both these problems: (a) since capsules migrate to a depth of less than 5 cm in the soil, there is a dramatic decrease in the amount of Mocap leaching into the ground water; (b) microencapsulation increases the stability of the active ingredient in all kinds of soil.
  • aqueous dispersions of pesticide and herbicide micro-capsules are particularly useful in controlled release pesticidal and herbicidal formulations because they can be diluted with water or liquid fertilizer and sprayed using conventional equipment, thereby producing uniform field coverage of the pesticide or herbicide/additives such as film forming agents can be added directly to the finished formulation to improve the adhesion of micro-capsules to foliage. In some cases, reduced toxicity and extended activity of encapsulated herbicides and pesticides have been noted.
  • a polymer separates from a solvent solution of the polymer by the action of a precipitating agent that reduces the solubility of the polymer in the solvent (e.g., a salt or a non-solvent for the polymer).
  • a precipitating agent that reduces the solubility of the polymer in the solvent (e.g., a salt or a non-solvent for the polymer).
  • Patents describing such processes and their shell wall material includes U. S. Patent Nos. 2,800,458 (hydrophilic colloids); 3,069,370 and 3,116,216 (polymers); 3,137,631 (denatured proteins); 3,418,250 (hydrophobic thermoplastic resins); and others.
  • British Patent No. 1 ,371 ,179 discloses a process which consists of dispersing an organic pesticide phase containing a polymethylene polyphenylisocyanate or toluylene diisocyanate monomer into an aqueous phase.
  • the wall forming reaction is initiated by heating the batch to an elevated temperature at which point the isocyanate monomers are hydrolyzed at the interface to form amines, which in turn react with unhydrolyzed isocyanate monomers to form the polyurea micro-capsulate wall.
  • One difficulty with this method is the possibility of continued reaction of monomer after packaging. Unless all monomer is reacted during the preparation, there will be continued hydrolysis of the isocyanate monomer with evolution of CO 2 , resulting in the development of pressure when the formulation is packaged.
  • U. S. Patent No. 3,577,515 describes a continuous or batch method, which requires a first reactant and a second reactant complimentary to the first reactant, with each reactant in separate phases, such that the first and second reactants react at the interface between the droplets to form encapsulated droplets.
  • the process is applicable to a large variety of polycondensation reactions, i.e., to many different pairs of reactants capable of interfacial condensation from respective carrier liquids to yield solid film at the liquid interface.
  • the resulting capsule skin may be produced as a polyamide, polysulfonamide, polyester, polycarbonate, polyurethane, polyurea or mixtures of reactants in one or both phases so as to yield corresponding condensation copolymers.
  • the reference describes the formation of a polyurea skin when diamines or polyamines (e.g. ethylene diamine, phenylene diamine, toluylene diamine, hexamethylene diamine and the like) are present in the water phase and di-isocyanates or polyisocyanates (e.g., toluene diisocyanate, hexamethylene diisocyanate and polymethylene polyphenylisocyanate) are present in the organic/oil phase.
  • diamines or polyamines e.g. ethylene diamine, phenylene diamine, toluylene diamine, hexamethylene diamine and the like
  • di-isocyanates or polyisocyanates e.g., toluene diisocyanate, hexamethylene diisocyanate and polymethylene polyphenylisocyanate
  • encapsulated formulations of insecticides and fertilizers prepared by us and others in the past were intended for foliar spraying and suffered from problems of UV degradation, whereas here microencapsulation is proposed as a means of dealing with degradation due to hydrolysis and microbial attack in the soil.
  • fertilizers such as sodium and potassium, which are not sensitive to basic conditions, does not teach or suggest a solution for application of organophosphorus nematocides that have such sensitivity.
  • said polyurea shell is formed from the reaction of a diamine or polyamine with a di-isocyanate or polyisocyanate.
  • a method for producing microencapsulated nematocides that are non-soluble in aqueous solutions as defined above comprising preparing an emulsion in water of a nematocide that is non-soluble in aqueous solutions as active ingredient in combination with a first polyurea-forming monomer and adding the second complementary polyurea-forming monomer to said emulsion to effect water interfacial polymerization of microcapsular polyurea shells with said active ingredient encapsulated therein.
  • a method for producing a microencapsulated organophosphorus nematocide as defined above comprising preparing an emulsion in water of an organophosphorus nematocidal active ingredient in combination with a first polyurea forming monomer and adding the second complementary polyurea forming monomer to said emulsion to effect water interfacial polymerization of microcapsular polyurea shells with said active ingredient encapsulated therein.
  • Solution A is heated to 40°C under stirring at 9-10 thousand rpm.
  • Solution B is then rapidly added to solution A.
  • solution C is added to the mixture.
  • the speed is reduced to 4-6 thousand rpm, the temperature being kept at 40-50°C._The reaction mixture is maintained under the latter conditions for 2 h, after which the pH is reduced to 7 with citric acid. Stirring is continued for a further 2 h at 40°C.
  • Solution D is then added, the reaction mixture is stirred for 30 min more, and the product is placed in containers.
  • the capsules were tested to determine the content of active ingredient.
  • a sample weighing 0.4 g was placed in a 25-ml measuring flask. 15 ml of methanol were added to the flask, which was then set in an ultrasonic bath for 40 min. Methanol was added up to the line and the sample injected to HP C apparatus.

Landscapes

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

Abstract

La présente invention a trait à des nématicides insolubles dans des solutions aqueuses et des nématicides organophosphorés encapsulés dans une enveloppe de microcapsule en polyurée ayant un diamètre d'environ 10 à 50 microns.
PCT/IL2003/000141 2002-03-14 2003-02-24 Nematicides encapsules WO2003075658A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003209627A AU2003209627A1 (en) 2002-03-14 2003-02-24 Encapsulated nematocides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL148,693 2002-03-14
IL14869302A IL148693A0 (en) 2002-03-14 2002-03-14 Encapsulated nematocides

Publications (1)

Publication Number Publication Date
WO2003075658A1 true WO2003075658A1 (fr) 2003-09-18

Family

ID=27799855

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2003/000141 WO2003075658A1 (fr) 2002-03-14 2003-02-24 Nematicides encapsules

Country Status (3)

Country Link
AU (1) AU2003209627A1 (fr)
IL (1) IL148693A0 (fr)
WO (1) WO2003075658A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4417916A (en) * 1979-03-26 1983-11-29 Monsanto Company Encapsulation by interfacial polycondensation
FR2591857A1 (fr) * 1985-12-25 1987-06-26 Kureha Chemical Ind Co Ltd Ethoprophos microencapsule.
US4889719A (en) * 1987-07-06 1989-12-26 Sumitomo Chemical Company, Ltd. Microencapsulated organophosphorus insecticidal composition for agricultural use
WO1995023506A1 (fr) * 1994-03-03 1995-09-08 Ben Gurion University Of The Negev Research And Development Authority Composition microencapsulee de chlorpyrifos ou d'endosulfan
WO1998049901A1 (fr) * 1997-05-08 1998-11-12 Ben Gurion University Of The Negev Research And Development Authority Procede servant a encapsuler du laygon
WO2001051195A1 (fr) * 2000-01-13 2001-07-19 Kureha Kagaku Kogyo Kabushiki Kaisha Microcapsule et procede de production
JP2002066307A (ja) * 2000-08-29 2002-03-05 Kureha Chem Ind Co Ltd マイクロカプセル粒状体およびその製造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4417916A (en) * 1979-03-26 1983-11-29 Monsanto Company Encapsulation by interfacial polycondensation
FR2591857A1 (fr) * 1985-12-25 1987-06-26 Kureha Chemical Ind Co Ltd Ethoprophos microencapsule.
US4889719A (en) * 1987-07-06 1989-12-26 Sumitomo Chemical Company, Ltd. Microencapsulated organophosphorus insecticidal composition for agricultural use
WO1995023506A1 (fr) * 1994-03-03 1995-09-08 Ben Gurion University Of The Negev Research And Development Authority Composition microencapsulee de chlorpyrifos ou d'endosulfan
WO1998049901A1 (fr) * 1997-05-08 1998-11-12 Ben Gurion University Of The Negev Research And Development Authority Procede servant a encapsuler du laygon
WO2001051195A1 (fr) * 2000-01-13 2001-07-19 Kureha Kagaku Kogyo Kabushiki Kaisha Microcapsule et procede de production
JP2002066307A (ja) * 2000-08-29 2002-03-05 Kureha Chem Ind Co Ltd マイクロカプセル粒状体およびその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CROPU [online] XP002240057, retrieved from CROPU Database accession no. 2001-88770 *

Also Published As

Publication number Publication date
IL148693A0 (en) 2002-09-12
AU2003209627A1 (en) 2003-09-22

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