WO2003049540A1 - Granules hydrodispersables contenant des pesticides a base de benzoylphenyluree - Google Patents

Granules hydrodispersables contenant des pesticides a base de benzoylphenyluree Download PDF

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Publication number
WO2003049540A1
WO2003049540A1 PCT/IL2002/000998 IL0200998W WO03049540A1 WO 2003049540 A1 WO2003049540 A1 WO 2003049540A1 IL 0200998 W IL0200998 W IL 0200998W WO 03049540 A1 WO03049540 A1 WO 03049540A1
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WO
WIPO (PCT)
Prior art keywords
wdg
formulations
water dispersible
active ingredient
composition
Prior art date
Application number
PCT/IL2002/000998
Other languages
English (en)
Inventor
Avner Barazani
Original Assignee
Makhteshim Chemical Works 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 Makhteshim Chemical Works Ltd. filed Critical Makhteshim Chemical Works Ltd.
Priority to AU2002358958A priority Critical patent/AU2002358958A1/en
Publication of WO2003049540A1 publication Critical patent/WO2003049540A1/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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

Definitions

  • the present invention relates to the field of pesticidal compositions, particularly to water dispersible granules containing pesticidal active ingredients.
  • WDG water dispersible granular
  • WDG formulations are commonly prepared by an extrusion process such as the process described in EP 321 527.
  • EP 633722 which is equivalent to U.S. 5,739,081 incorporated in its entirety herein by reference, describes a water dispersible granular formulation suitable for agricultural applications and a method for preparing said granules, according to which the active ingredient is in liquid form and absorbed into the granule, thus producing a stable WDG.
  • EP 633,722 demonstrates that although the WDG formulations therein are safer and more convenient to handle, in some cases the efficacy of the WDG is lower than SC or EW formulations.
  • the group of pesticides known as benzoyl ureas which includes ter alia, novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron and teflubenzuron are used as insect growth regulators (IGR).
  • IGR insect growth regulators
  • Said compounds are solid at ambient temperatures and have an extremely low water solubility. Accordingly, the commercial products containing said IGR's as active ingredients are commonly sold as suspension concentrates (SC) or emulsion in water (EW) formulations.
  • SC suspension concentrates
  • EW emulsion in water
  • a further purpose of the present invention is to present a method for pest control wherein an improved WDG formulation is applied.
  • the present invention provides a pesticidal composition in the form of a water dispersible granule (WDG) which contains one or more benzoylphenyl urea (BPU) compound as an active ingredient, wherein said composition is prepared by absorbing the active ingredient in liquid form or solution, into an absorbent water dispersible granule prepared from filler particles in a finely divided state and a dispersing agent.
  • WDG water dispersible granule
  • BPU benzoylphenyl urea
  • a method for pest control comprising applying the presently described WDG composition to a plant or area in need of pest control.
  • WDG formulations containing one or more benzoylphenyl urea compounds as active ingredients are more efficacious than other WDG formulations of BPU's.
  • WDG formulations of the present invention are more efficacious than suspension concentrate (SC) and emulsion concentrate (EC) formulations of BPU's.
  • SC suspension concentrate
  • EC emulsion concentrate
  • a WDG formulation containing one or more BPU pesticidal compound containing one or more BPU pesticidal compound.
  • BPU's suitable for the present invention are (common names) novaluron, lufenuron, hexaflumuron, triflumuron, diflubenzuron, chlorfluazuron, flufenoxuron, fluazuron, flucycloxuron, teflubenzuron and noviflumuron (also known by code name XDE 007).
  • Said formulation containing 0.5% to 45% BPU, preferably 1% to 15%.
  • the description of the present pesticidal composition shall now proceed in accordance with the method of preparation described in EP 633,722.
  • the BPU in accordance with the present invention needs to be in a liquid state or formed into a liquid state, by for example dissolution in a suitable solvent or non-volatile compatible material, such as vegetable or mineral oils or in the form of a suspension or emulsion.
  • a suitable solvent or non-volatile compatible material such as vegetable or mineral oils or in the form of a suspension or emulsion.
  • the non-volatile compatible material may be surface active agent or adjuvant therefor.
  • liquid state also refers to suspensions, emulsions and solutions of the active ingredient.
  • the BPU is preferably in a form in which it is miscible, dispersible or emulsifiable with water preferably by addition of suitable emulsifiers or by use of a suitable solvent or co- solvent.
  • EC formulations of the BPU with a reduced amount of the carrier organic solvent are suitable for absorption into the absorbent granules.
  • the BPU it is within the scope of the present invention for the BPU to be rendered water miscible, dispersible or emulsifiable after it has been added to the absorbent granules. This can be achieved by pre-adding or post-adding suitable surfactants to the granules.
  • the surfactants are such that if pre-blended with the BPU, the mixture is water miscible, dispersible or emulsifiable.
  • water miscible it is meant that the composition may be in the form of a fine emulsion, suspension or solution.
  • the WDG is prepared by absorbing the active ingredient in liquid form, into an absorbent water dispersible granule prepared from filler particles in a finely divided state and a dispersing agent.
  • the finely divided filler particles that are used to prepare the absorbent granules of this invention will normally be selected from inert mineral fillers.
  • the particle size of the finely divided filler will depend upon the ultimate use of the granule. When used in spray tanks with conventional spray equipment the filler will need to be of a size to ensure that it passes freely through the spray nozzles without blockage.
  • the preferred particle size will be less than 150 ⁇ m. The most preferred range will be 1-50 ⁇ m.
  • the filler materials should adhere also be of a type that do not of themselves adhere and form agglomerates that will not redisperse readily. Accordingly, precipitated silica is not preferred but can be tolerated at low levels.
  • Suitable substances for use as the finely divided filler include mineral earths and clays such as bentonite, kaolin, attapulgite, diatomaceous earth, zeolites, calcium carbonate, talc, muscovite mica and manufactured materials such as precipitated silicas and silicates, fused sodium potassium, aluminum silicate (heat processed perlite) or organic materials such as coals, lignites and plastics.
  • the fillers are preferably water insoluble.
  • the finely divided filler itself may be absorbent as in the case of diatomaceous earth, attapulgite or zeolites but this is not essential.
  • Preferred materials include heat processed perlite, talc and muscovite mica, and combinations of such materials.
  • the absorbency of the granules is influenced by the degree of packing and the type of filers used. A mixture of different fillers can also be used.
  • the finely divided filler particles are water dispersible by including a dispersing agent.
  • the amount of dispersing agent will vary from 1-30% w/w of the absorbent granule and more preferably 5-15% w/w of granule.
  • Suitable dispersing or wetting agents include surface active agents and water soluble polymers, for example, lignosulphonate salts, polyacrylates and phosphate esters condensation products of formaldehyde, polyethylene glycol, and sugars.
  • Suitable absorbent granules have been prepared with the following dispersing agent: "Morwet D425" (sodium naphthalene formaldehyde condensate ex Witco Corporation, USA) "Morwet EFW” Sulfated Alkyl Carboxylate and Alkyl Naphthalene Sulfonate—Sodium Salt “Tamol PP” (sodium salt of a phenolsulphonic acid condensate) “Reax 80N” (sodium lignosulphonate) "Wettol Dl” sodium alkylnaphthalene sulphonate (ex BASF).
  • the dispersing or wetting agents are anionic surfactants.
  • binding agents may be used wherein said agents are selected from a range of natural or synthetic gums, sugars, and polymers. Materials that do not swell rapidly upon hydration or become viscous are preferred.
  • auxiliary agents such as surfactants and disintegrating agents may be added to modify the properties of the granules.
  • the materials comprising the preformed granule may be combined in any sequence and blended in a suitable blender and granulated using known methods and equipment for making granules.
  • granules are preferably dried to a moisture content of not more than 1.0% w/w (as loss on drying). Temperature during drying is preferably controlled to a low temperature such as below 50°C.
  • Loading of the substance can take place in any suitable apparatus.
  • the apparatus will deliver the BPU in liquid form to the agitated granules in such a manner that the liquid is taken up uniformly amongst all granules without damaging the granules.
  • a suitable apparatus can therefore be a rotating cylinder, for example a Diosna universal mixer ex Dierks and Sohne GmbH & Co KG, a cone mixer with the liquid substance being delivered rapidly to the preformed granules via spray nozzles in a manner to distribute the substance over the surface of the absorbent granules as quickly as possible.
  • the spray can be introduced through air atomising nozzles to ensure even spread of the liquid active substance the granules.
  • Flat spray jets will in some cases be appropriate.
  • Other means of delivering the liquid in the manner required can also be used.
  • the BPU will be mixed with an emulsifier to form an emulsifiable concentrate in a liquid form which can then be absorbed onto the preformed granule.
  • the liquid substance can be dissolved in a suitable solvent, selected such that the solution is miscible with water, and then be absorbed onto the granule.
  • the amount of solvent used in such a situation will be as low as possible in order to enable loading as high a concentration of the active substance into each granule as may be desired. If the liquid substance is miscible with water in its natural state, then it can be loaded onto the preformed granules without further modification.
  • the BPU may be converted to a water soluble form by the addition of a suitable emulsifier. It is possible for the surfactant and active material to be absorbed sequentially into the granules rather than as a premix. It is also possible for the granules to be prepared with the emulsifier present and the BPU is then subsequently absorbed into the granules. Dispersibility is still maintained in these variations.
  • Emulsifiers can be of the anionic, cationic or non-ionic type.
  • the preformed absorbent granules can be used to absorb liquid adjuvants which are substances designed to enhance the effect of the BPU.
  • the adjuvant can be incorporated with the BPU in liquid form where the adjuvant and the substance are mutually compatible and remain so or alternatively a preformed granule can be loaded with BPU and then be subsequently loaded with an adjuvant.
  • the BPU can be loaded into a first sample of the preformed granules and the adjuvant loaded into a second sample and these two samples added to water for spraying.
  • the BPU in solid form can be used as the finely divided filler, as long as it is rendered miscible in water.
  • the preformed granule containing the BPU can then be used to absorb an adjuvant which is an enhancer for the BPU's activity.
  • the method by which the granules are formed is not particularly critical. However the type of granulation technique used may affect the absorbency of the granules. The granulation technique described in application PCT/AU 88/00201 is particularly advantageous.
  • the present invention provides a method for pest control comprising treating an area in need of control with the presently claimed pesticidal composition.
  • the present method may be applied for agricultural and horticultural purposes, ornamentals and non- agricultural purposes, e.g. public health and domestic use. Said method is effective for the control of pests which are sensitive to BPU's.
  • the present method is particularly effective for controlling insects of, ter alia, the orders Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera, as well as representatives of the order Acarina of the families Ixodidae, Argasidae, Tetranychidae and Dermanyssidae.
  • said method is effective in controlling flies, e.g. Musca domestica, termites, cockroaches and mosquito larvae.
  • the presently claimed method is also suitable for controlling plant-destructive feeding insects in ornamentals and crops of useful plants, especially in cotton (e.g. against Spodoptera littoralis and Heliothis virescens) and in fruit and vegetables (e.g.
  • the present method is further effective for controlling ectoparasites such as Lucilia sericata, in domestic animals and productive livestock, e.g. by treating animals, cowsheds, barns, stables etc., and pastures.
  • the pesticidal composition is used to prepare a tank mix which is then applied via spraying to the area or crop needing treatment.
  • the active ingredient concentration in the tank mix is adjusted to the particular application, depending on agricultural or non-agricultural application, the crop and the pest.
  • spraying is the preferred method of application.
  • the present method may also be applied in conjunction with other pest control agents, either in a mixture or by sequential application.
  • suitable additional pesticides include: organophosphorus compounds, ' nitrophenols and derivatives thereof, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons preparations.
  • EC An emulsion concentrate containing 100 gr a.i./liter (equivalent to EC- 10).
  • 75-WDG A water dispersible granule formulation containing 75 gr a.i./Kg prepared according to prior-art methods.
  • WDG-50 A water dispersible granule formulation containing 50 gr a.i./Kg prepared according to prior-art methods.
  • SC-10 A suspension concentrate containing 100 gr a.i./liter.
  • WDG 7.5 A water dispersible granule formulation containing 75 gr a.i./Kg prepared according the present invention.
  • Example 1 WDG formulation of novaluron
  • novaluron formulation No. of Larval mortality, % at LWG in mg a.i./litre L3 4 d 8d rel. to con.
  • Castor bean leaves treated with 4 mg a.i./litre of each of the novaluron formulations, were exposed to 3 rd -instar S. littoralis (11+1 mg) for 4-day feeding and for additional 4 days on untreated leaves. Larval weight gain was determined at day 4 and larval mortality at day 4 and 8. Data are averages ⁇ SEM of 6 replicates of 10 larvae each. Within columns, means followed by the same letter do not differ significantly at P 0.05.
  • Example 4 Comparative Example of Formulations Potency of WDG-7.5 at 0.1 mg a.i./liter in comparison with novaluron EC and SC formulations.
  • Castor bean leaves treated with 0.1 mg a.i./litre of each of the novaluron formulations were exposed to 3 rd -instar S. littoralis (11+1 mg) for 4-day feeding and for additional 4 days on untreated leaves.
  • Larval mortality was determined at day 4 and day 8.
  • Larval weight gain was determined at day 4.

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

Abstract

L'invention concerne une composition pesticide sous forme de granules hydrodispersables contenant au moins un composé à base de benzoylphenyl urée (BPU) en tant qu'ingrédient actif. Cette composition est préparée par absorption de l'ingrédient actif dans une granule hydrodispersable absorbante.
PCT/IL2002/000998 2001-12-12 2002-12-11 Granules hydrodispersables contenant des pesticides a base de benzoylphenyluree WO2003049540A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002358958A AU2002358958A1 (en) 2001-12-12 2002-12-11 Water dispersible granules containing benzoylphenylurea pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL147063 2001-12-12
IL14706301A IL147063A0 (en) 2001-12-12 2001-12-12 Pesticidal formulation

Publications (1)

Publication Number Publication Date
WO2003049540A1 true WO2003049540A1 (fr) 2003-06-19

Family

ID=11075894

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2002/000998 WO2003049540A1 (fr) 2001-12-12 2002-12-11 Granules hydrodispersables contenant des pesticides a base de benzoylphenyluree

Country Status (3)

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AU (1) AU2002358958A1 (fr)
IL (1) IL147063A0 (fr)
WO (1) WO2003049540A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110122501A (zh) * 2019-06-14 2019-08-16 青岛润农化工有限公司 一种除虫脲水分散粒剂及其制备方法
WO2022264064A1 (fr) 2021-06-16 2022-12-22 Adama Makhteshim Ltd. Composition solide hydrodispersable de novaluron
KR102577638B1 (ko) * 2023-03-28 2023-09-13 (주)국보싸이언스 침강 부상형 살충 조성물

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60193960A (ja) * 1984-03-15 1985-10-02 Ishihara Sangyo Kaisha Ltd Ν−ベンゾイル−ν’−フエニルウレア系化合物及びそれらを含有する殺虫剤
JPS62155248A (ja) * 1985-12-27 1987-07-10 Ishihara Sangyo Kaisha Ltd Ｎ−ベンゾイル−ｎ’−フエニルウレア系化合物及びそれらを含有する殺虫剤
EP0349999A2 (fr) * 1988-07-08 1990-01-10 Dowelanco Procédé pour préparer des pesticides dispersables dans l'eau, hautement actifs
US5739081A (en) * 1992-01-24 1998-04-14 Ici Australia Operations Proprietary Ltd. Water dispersible granules of liquid pesticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60193960A (ja) * 1984-03-15 1985-10-02 Ishihara Sangyo Kaisha Ltd Ν−ベンゾイル−ν’−フエニルウレア系化合物及びそれらを含有する殺虫剤
JPS62155248A (ja) * 1985-12-27 1987-07-10 Ishihara Sangyo Kaisha Ltd Ｎ−ベンゾイル−ｎ’−フエニルウレア系化合物及びそれらを含有する殺虫剤
EP0349999A2 (fr) * 1988-07-08 1990-01-10 Dowelanco Procédé pour préparer des pesticides dispersables dans l'eau, hautement actifs
US5739081A (en) * 1992-01-24 1998-04-14 Ici Australia Operations Proprietary Ltd. Water dispersible granules of liquid pesticides

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198546, Derwent World Patents Index; Class C03, AN 1985-285507, XP002237720 *
DATABASE WPI Section Ch Week 198733, Derwent World Patents Index; Class C03, AN 1987-231613, XP002237719 *
OELMUELLER R ET AL: "SYNTHETIC SILICAS IN PESTICIDE FORMULATION WITH SPECIAL EMPHASIS ON WATER DISPERSIBLE GRANULES", ASTM SPECIAL TECHNICAL PUBLICATION, AMERICAN SOCIETY FOR TESTING MATERIALS,, US, PAGE(S) 85-97, ISSN: 0066-0558, XP000574568 *
ROGERS, A. J. ET AL: "Tests of two insect growth regulators formulated on sand against larvae o salt -marsh mosquitoes", MOSQUITO NEWS (1976), 36(3), 273-7, XP001147725 *
SCHAEFER, C. H. ET AL: "Application of diflubenzuron sand granules for controlling Culex tarsalis larvae breeding under mature cotton stands", PROCEEDINGS AND PAPERS OF THE ANNUAL CONFERENCE OF THE CALIFORNIA MOSQUIT AND VECTOR CONTROL ASSOCIATION (1986), 54TH, 39-41, XP001147726 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110122501A (zh) * 2019-06-14 2019-08-16 青岛润农化工有限公司 一种除虫脲水分散粒剂及其制备方法
WO2022264064A1 (fr) 2021-06-16 2022-12-22 Adama Makhteshim Ltd. Composition solide hydrodispersable de novaluron
KR102577638B1 (ko) * 2023-03-28 2023-09-13 (주)국보싸이언스 침강 부상형 살충 조성물

Also Published As

Publication number Publication date
AU2002358958A1 (en) 2003-06-23
IL147063A0 (en) 2002-08-14

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