WO1999043206A1 - Systeme et procede de conditionnement d'une composition chimique - Google Patents

Systeme et procede de conditionnement d'une composition chimique Download PDF

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Publication number
WO1999043206A1
WO1999043206A1 PCT/US1999/003102 US9903102W WO9943206A1 WO 1999043206 A1 WO1999043206 A1 WO 1999043206A1 US 9903102 W US9903102 W US 9903102W WO 9943206 A1 WO9943206 A1 WO 9943206A1
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WO
WIPO (PCT)
Prior art keywords
package
water soluble
poly
group
gum
Prior art date
Application number
PCT/US1999/003102
Other languages
English (en)
Inventor
Min Xie
Fred Carl Rosa
Jackie Mote
Original Assignee
Uniroyal Chemical Company, Inc.
Gustafson, Inc.
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 Uniroyal Chemical Company, Inc., Gustafson, Inc. filed Critical Uniroyal Chemical Company, Inc.
Priority to AU32922/99A priority Critical patent/AU3292299A/en
Priority to CA002285202A priority patent/CA2285202A1/fr
Publication of WO1999043206A1 publication Critical patent/WO1999043206A1/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
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
    • B65D65/38—Packaging materials of special type or form
    • B65D65/46—Applications of disintegrable, dissolvable or edible materials

Definitions

  • the present invention relates to a system and method for packaging a chemical composition in a package which is water soluble
  • Pesticides and other chemicals used as active ingredients in the agricultural industry are often formulated in liquid compositions While liquid compositions are convenient because of the ease in which they can be handled and dispersed, they nevertheless present safety problems For example, there is a danger of spillage or leakage if the package in which they are stored is punctured There is also a danger of splashing when the liquid is added to a tank of water
  • an agrochemical can be placed in a water soluble bag which, in turn, is placed within a non-water soluble container In use, the water soluble bag is removed from the non-water soluble container and simply placed in the tank of water into which the agrochemical is to be diluted
  • the agrochemical can be in the form of a powder
  • the agrochemical can be packaged in the form of a liquid solution or gel If a liquid or gel is employed the liquid solvent must be compatible with the water soluble package By compatible" is meant that the solvent will not dissolve the package material or cause noticeable deterioration of the package
  • U S Patent No 5, 139, 152 to Hodakowski et al discloses a method for packaging an agrochemical by dispersing the hazardous chemical in a hydrophobic solvent an aromatic solvent Surfactants and gelling agents are also employed to form a dispersable gel which can be packaged in a water soluble bag The difficulty with this method is that a relatively high percentage of surfactants must be used to help disperse the hydrophobic
  • Such surfactants can increase the phytotoxicity of the composition and thereby cause unintended damage to plant life
  • water based gels are also known to be packageable in water soluble bags.
  • U S Patent No. 5,341 ,932 to Chen et al discloses the use of an aqueous gel to package hazardous agrochemicals
  • electrolytes are included as a component of the gel composition to render the bag material insoluble in the gel Nevertheless, use of electrolytes presents difficulties Even a small amount of water in the gel system can soften or dissolve water soluble packaging At elevated temperatures the solubility of electrolytes in water increases and the aqueous phase becomes unsaturated This leaves more water available to attack the water soluble packaging At lower temperatures the electrolytes may crystallize out
  • the formulations which rely on electrolytes to make aqueous phases compatible with water soluble packaging can be rendered impractical because of their sensitivity to temperature variations It would be desirable to have hydrophilic solvent based compositions which can be stored in water soluble bags and which don't suffer from the disadvantages described above
  • a system and method are provided tor storing an active ingredient in a water soluble package
  • the svstem comprises a) a first package fabricated from a water soluble material, and b) a storage formulation having the active ingredient as a first component and a hydrophilic non-aqueous solvent as a second component, the hydrophilic non- aqueous solvent being capable of dissolving the active ingredient but not the water soluble material from which the first package is fabricated, said storage formulation being contained in the first package
  • the method comprises a) producing a storage formulation by forming a solution or dispersion of the active ingredient in a non-aqueous hydrophilic solvent. b) placing the storage formulation in the water soluble package, w herein the water soluble package is fabricated from a material which is insoluble in the non-aqueous hydrophilic solvent, and c) sealing the water soluble package to enclose the storage formulation therein
  • the storage formulation can optionally include other additives such as gelling agents, surfactants, and antifoaming agents
  • the water soluble package is stored in a non-water soluble package
  • the present method for packaging an active ingredient in packages which are water soluble includes the step of dissolving or dispersing the active ingredient in a non-aqueous hydrophilic solvent which is compatible with the water soluble package
  • the combination of the active ingredient and hydrophilic solvent provides a storage formulation which can optionally include gelling agents, surfactants, and other additives as described below
  • the storage formulation is placed in the water soluble package, which is then sealed by any suitable method known to those with skill in the ait and preferably enclosed in a non-water soluble container
  • the non-water soluble container can be made from metal or plastic, and is preferably an outer envelope iab ⁇ cated from polymers such as polyolefins and polyesters including, for example, polyethylene, polypropylene, polyethylene terephthalate, polyvinyl chloride, and the like
  • the outer envelope is manually opened and the water soluble package is removed and added to, for example, a tank of water in which the package dissolves and releases its contents
  • the water soluble package does not need to be opened and there is less danger of the user coming into manual contact with the activ e ingredient in the formulation
  • any type of water soluble or non-water soluble chemical may be packaged in accordance with the method described herein, for example, dyes, and water treating agents such as bactericides, flocculants.
  • the agrochemicals to be packaged can be insecticides, nematicides, herbicides, fungicides, plant growth regulators, rodenticides, or a combination of these agents
  • agents include, but are not limited to, water soluble derivatives such as ammonium salts, monovalent or divalent metal salts, or amine salts of the following exemplary compounds fungicides such as tebuconazole, metalaxyl, imazalil, thiabendazole, and 2-(th ⁇ ocyanatomethylth ⁇ o)benzoth ⁇ azole herbicides (or defoliants) such as acetochlor. imazapyr, paraquat, 2,4-D.
  • Inorganic pesticides include sulfur, sodium chlorate, sodium fluoride, sodium fluoroacetate, and bordeaux mixture Other pesticides which may be packaged in accordance with the method and system described herein may be found in The Pesticide Manual. Ninth Ed , British Crop Protection Council Pub (1991)
  • Organic agrochemicals which are m the form of salts or water soluble salts can be simple amine derivatives or ammonium or monovalent metal or acid halide or sulfate derivatives
  • the active ingredients which are in a salt form may be more particularly in the form of a salt of an amine or of ammonium sodium, potassium, lithium, ammonium, alkanolamines, and simple alkyl or tatty amines
  • the water soluble package is preferably fabricated from a polymeric water soluble film, more preferablv a cold water soluble film Cold water soluble means
  • Suitable materials for fabricating the water soluble package are water soluble (or possibly water dispersible) materials which are insoluble in the organic solvents used to dissolve or disperse the agrochemical active ingredient
  • suitable materials include polyethylene oxide, polvethvlene glycol. starch and modified starch, alkyl and hvdroxvalkylcellulose, hydroxypropyl cellulose, methylcellulose. carboxvmethvlcellulose.
  • polyvinylethers such as poly methyl vinylether or poly(2- methoxyethoxyethylene), poly(2,4-d ⁇ methyl-6-t ⁇ az ⁇ nylethylene, poly(3-morphohnyl ethylene), poly(N-l ,2,4-t ⁇ azolylethylene), poly(vmylsulfon ⁇ c acid), polyanhyd ⁇ des, low molecular weight melamine-formaldehyde resins, low molecular weight urea- formaldehyde resins, poly (2-hydroxy ethyl methacrylate), polyacryhc acid and its homologs
  • the enveloping film comprises or is made from polyvinylalcohol ("PVA")
  • PVA polyvinylalcohol
  • PVA is generally partially or fully alcoholysed or hydrolysed (e.g. , 40-100% , preferably 80-99% alcoholysed or hydrolysed)
  • Polyvinyl acetate (or other ester) film or copolymers or other derivatives of such polymers can also be used PVA films found suitable for use in the present method are available under the designation M 8435 002 from Chris Craft Industrial Products, Inc located at 450 West 169th Street, South Holland, IL 60473 and KC grade 2 mil PVA film from Mitsui Plastics. Inc located at 1 1 Martine Avenue. White Plains, NY 10606
  • the non-aqueous hydrophilic solvent must be able to dissolve or at least form a dispersion with the active ingredient while being compatible with the construction material of the package
  • Such solvents are capable of dissolving or dispersing both hydrophilic and hydrophobic agents and include gamma-butyrolactone and dipropyleneglycol monomethylether, for example
  • the storage formulation does not need to rely on the presence of electrolytes to preserve the integrity of the water soluble package
  • Gelling agents can include organic water soluble gums and resms such as alginates. carboxymethylcellulose. carrageenan, guar gum. agar. gum arabic, gum ghatti, gum karaya, gum tragacanth, hydroxyethylcellulose. hydroxypropylcellulose, hydroxypropyl methylcellulose, locust bean gum, pectins, polyacrylamide, polyacrylic acid, polyethylene glycol. polyethylene oxide, polyvinyl alcohol, polyvinyl pyrrolidone, starch, tamarind gum. and xanthan gum.
  • organic water soluble gums and resms such as alginates. carboxymethylcellulose. carrageenan, guar gum. agar. gum arabic, gum ghatti, gum karaya, gum tragacanth, hydroxyethylcellulose. hydroxypropylcellulose, hydroxypropyl methylcellulose, locust bean gum, pectins, polyacrylamide
  • the gelling agents can be inorganic as well.
  • examples include, but are not limited to, the following: natural clays such as kaolins, serpentines, smectites (montmorillonites), bentonites, illites, glauconite, chlorites, vermiculites. mixed-layer clays, attapulgite, saponite and sepiolite, and synthetic clays such as synthetic smectic clays, silicates and fluorosilicates may also be used.
  • Especially preferred gelling agents for the method set forth herein include polyvinyl pyrrolidone, hydroxypropyl methylcellulose. polyethylene oxide, hydroxypropyl cellulose, and silica (as fumed silica). Gelling agents advantageously provide self sealing capability in the event that the water soluble package develops pin hole leaks.
  • the storage formulation can optionally include other additives such as antifoaming agents to help remove bubbles from the gel.
  • An example of an antifoaming agent suitable for use in the method described herein is a modified polyether-polysiloxane containing more than 50% polysiloxane, which is commercially available under the designation Tegosipon 3062 from the Goldschmidt Co. located at 914 East Randolph Road, Hopewell, VA 23860.
  • Surfactants can optionally be included in the storage formulation but are not required.
  • Surfactants which can be used in the method described herein include, but are not limited to, the following: alkanolamides; poly condensates of ethylene oxide with fatty alcohols, fatty esters, or fatty amines, or substituted phenols (particularly alkyphenols or arylphenols); block copolymers with ethoxy and propoxy groups; esters of fatty acids with poly sols such as glycerol or glycol; polysaccharides: organopolysiloxanes; sorbitan derivatives: ethers or esters of sucrose or fructose, salts of lignosulphonic acids, salts of phenyl sulphonic or naphthalene sulphonic acids, diphenyl sulfonates; alkyaryl sulfonates: sulfonated fatty alcohols or amines or amides: poly condensates of ethylene oxide
  • Example 1 A gel base was made by mixing 90 parts of gamma-butyrolactone and 10 parts polyvinyl pyrrolidone gelling agent at room temperature until the polyvinyl pyrrolidone was dissolved
  • the polyvinyl pyrrolidone was obtained under the designation PVP K-90 from International Specialty Products, located at 1361 Alps Road. Wayne. NJ 07470
  • the resulting product was a homogeneous, clear gel with a viscosity of 680 cps
  • Example 2 A gel base was made by mixing 93 parts of gamma-butyrolactone and 7 parts polyvinyl pyrrolidone gelling agent at room temperature until the polyvinyl pyrrolidone was dissolved
  • the resulting product was a homogeneous, clear gel having a viscosity of 1360 cps
  • a gel base was made by mixing 91 5 parts gamma-butyrolactone and 8 5 parts hydroxvpropyl methylcellulose gelling agent at room temperature until the gelling agent was completely dispersed
  • the hydroxypropyl methylcellulose gelling agent was obtained under the designation Methocel E5 from Dow Chemical Co
  • the resulting product was a homogeneous, semi-clear gel having a viscosity of 500 cps A pinhole test was performed and no dripping was observed
  • Example 4 A gel base was made by mixing 90 parts gamma-butyrolactone and 10 parts hydroxypropyl methylcellulose gelling agent (Methocel E5) at room temperature until the gelling agent was completely dispersed The resulting product was a homogeneous semi- clear gel having a viscosity of 1200 cps A pinhole test was performed and no dripping was observed
  • Example 5 A gel base was made by mixing 98 parts gamma-butyrolactone and
  • a gel base was made by dispersing 6 5 parts hydroxypropyl methylcellulose (Methocel E5) in 12 parts polyethylene glycol This mixture was then added to 81 4 parts gamma-butyrolactone and then heated briefly to 60°C Then 0 1 parts of Tegosipon 3062 antifoaming agent was then added to the mixture, which was then cooled with continued stirring until a homogeneous semi-clear gel was obtained The resulting gel had a viscosity of 1220 cps
  • Example 7 A gel base was made by dispersing 6.5 parts hydroxypropyl methylcellulose ( Methocel E5) in 12 parts polyethylene glycol and adding this mixture to 81.4 parts gamma-butyrolactone.
  • Example 8 A gel base was made by mixing 97 parts gamma-butyrolactone and 3 parts of polyethylene oxide gelling agent.
  • the polyethylene oxide was obtained under the designation Polyox 1105 from Union Carbide Co. The mixture was briefly heated to 40°C with stirring and then cooled with continued stirring until a homogeneous, clear gel was formed. The gel had a viscosity of 2200 cps.
  • Example 9 A gel base was made by mixing 98 parts gamma-butyrolactone with 2 parts hydroxypropyl cellulose gelling agent.
  • the hydroxypropyl cellulose was obtained under the designation Klucel G from Aqualon Co. of Hopewell, VA. The mixture was heated to 50°C and cooled with continued stirring until a homogeneous semi-clear gel was obtained having a viscosity of 4300 cps.
  • a gel base was made by mixing 98 parts gamma-butyrolactone with 2 parts Klucel G. The mixture was heated to 70°C and cooled with continued stirring until a homogeneous semi-clear gel was obtained having a viscosity of 10,400 cps.
  • Example 1 1 A gel base was made by mixing 90 parts gamma-butyrolactone and 10 parts hydroxypropyl cellulose gelling agent obtained under the designation Klucel L from Aqualon Co The mixture was heated to 70 °C and then cooled with stirring until a homogeneous semi-clear gel was obtained having a viscosity of 7200 cps
  • Example 12 A gel base was obtained by mixing 86 parts gamma-butyrolactone and 14 parts hydroxypropyl cellulose gelling agent obtained under the designation Klucel E from Aqualon Co The mixture was heated to 60 °C and then cooled with stirring until a homogeneous semi-clear gel was obtained having a viscosity of 2900 cps
  • Example 13 A gel base was made by mixing 80 parts gamma-butyrolactone and 20 parts fumed silica obtained under the designation HiSil 233 from PPG Industries, Inc. , located at one PPG Place, Pittsburgh, PA 15272 The components were stirred together at room temperature until a homogeneous semi-clear gel was obtained having a viscosity of 4000 cps.
  • Example 14 A gel base made in accordance with the method of Example 3 was provided and 25 parts metalaxyl were added to 75 parts of the gel at room temperature with stirring until the Metalaxyl was completely dissolved The resulting storage formulation was amber colored, homogeneous and semi-clear
  • a dispersion test was performed and the formulation was observed to disperse in water in less than 1.5 minutes to form a stable homogeneous clear solution without precipitation. Also, a sample of the storage formulation in a 2.0 mil PVA bag was kept at
  • Example 15 A gel base made in accordance with the method of Example 4 was provided and 25 7 parts of metalaxyl were added to 74 3 parts of the gel at room temperature with stirring until the Metalaxvl was completely dissolved The resulting storage formulation was amber colored, homogeneous, and semi-clear
  • Example 16 A gel base made in accordance with the method of Example 2 was provided and 25 parts of metalaxyl were added to 75 parts of the gel at room temperature with stirring until the Metalaxyl was completely dissolved The resulting storage formulation was an amber colored, homogeneous, clear gel having a viscosity of 1680 cps
  • a dispersion test was performed and the formulation was observed to disperse in less than about 5 minutes to form a clear solution without precipitation
  • Example 17 A gel base made in accordance with the method of Example 7 was provided and 25 7 parts of metalaxyl were added to 74 3 parts of the gel base at room temperature with stirring until the Metalaxyl was completely dissolved
  • the resulting storage formulation was an amber colored, homogeneous, clear gel having a viscosity of 2160 cps
  • a sample of the storage formulation in a 2.0 mil PVA bag was packaged in a second non-soluble plastic bag and stored for more than one year under ambient conditions. No leakage was observed. The bags remained flexible.
  • Example 18 A gel base made in accordance with the method of Example 1 1 was provided and 25.7 parts of metalaxyl were added to 74.3 parts of the gel base at room temperature with stirring until the Metalaxyl was completely dissolved.
  • the resulting storage formulation was an amber colored homogeneous, semi-clear gel having a viscosity of 4800 cps.
  • a dispersion test was performed and the formulation was observed to disperse in less than 2 minutes to form a stable clear solution with no precipitation.
  • Example 19 Three parts of polyethylene polypropylene glycol. obtained under the designation Pluronic P 104 from BASF Corp. , and 25.6 parts metalaxyl were added to 62.2 parts of gamma-butyrolactone at room temperature with stirring until the metalaxyl was completely dissolved. Then 9 parts of fumed silica, obtained under the designation Aerosil 300 from Degussa Co. , and 0.2 parts of Tegosipon 3062 were added to the mixture with continued stirring until an amber colored, homogeneous, semi-clear gel was obtained having a viscosity of 2500 cps.
  • Pluronic P 104 from BASF Corp.
  • metalaxyl obtained under the designation Aerosil 300 from Degussa Co.
  • Tegosipon 3062 were added to the mixture with continued stirring until an amber colored, homogeneous, semi-clear gel was obtained having a viscosity of 2500 cps.
  • Example 20 A gel base made in accordance with the method of Example 3 was provided, and 54 parts of imazalil were added to 26 parts of gel base at room temperature with stirring until the imazalil was completely dissolved Then 20 parts of polyethylene glycol. obtained under the designation Witconol 5906 from Witco Corporation, located at One American Lane. Greenwich, CT 06831. were added to the mixture The resulting storage formulation was an amber colored, homogeneous, semi-clear gel
  • a dispersion test was performed and the formulation was observed to disperse in less than 1 5 minutes to form a milky emulsion
  • the milky emulsion exhibited some precipitation after 24 hours but returned to emulsion after agitation
  • Example 21 A gel base made in accordance with the method of Example 7 was provided, and 59 5 parts of imazalil were stirred into 20 5 parts of the gel base at room temperature until completely dissolved Then 20 parts of Witconol 5906 were added with continued stirring until an amber colored homogeneous, semi-clear gel was obtained having a viscosity of 660 cps
  • Example 22 A gel base made in accordance with the method of Example 3 was provided and 10 parts of tebuconazole were stirred into 88 parts of gel base at room temperature
  • a dispersion test was performed, and the storage formulation was observed to disperse in less then 1 minute to form a milky fine suspension.
  • the suspension showed some precipitation after 24 hours but returned to suspension after agitation.
  • a sample of storage formulation was sealed in a PVA bag and was observed to remain homogeneous and clear after one week storage at - 10°C.
  • Example 23 A gel base made in accordance with the method of Example 5 was provided and 10 parts of tebuconazole were stirred into 88 parts of gel base at room temperamre until the tebuconazole was completely dissolved. Then 2 parts Witconol 5906 were added to the mixture with stirring. The resulting storage formulation was a colorless, homogeneous, semi-clear gel.
  • a sample of storage formulation was sealed in a PVA bag and was observed to remain homogeneous and clear after six months of storage.
  • Example 24 A gel base made in accordance with the method of Example 7 was provided and 10 parts of tebuconazole were stirred into 87.6 parts of gel base at room temperature until the tebuconazole was completely dissolved. Then 2 parts Witconol 5906 were added to the mixture with stirring. The resulting storage formulation was a colorless, homogeneous, semi-clear gel. A pinhole test was performed. No dripping was observed. The gel was self sealing after a period of time.
  • a dispersion test was performed, and the storage formulation was observed to disperse in less then 2 minutes to form a milky fine suspension.
  • the suspension showed some precipitation after 24 hours but returned to suspension after agitation.
  • a dispersion test was performed In 22°C water the formulation was completely dispersed in 2 5 minutes In 1 °C water the formulation was completely dispersed in less than 4' minutes The diluted sample showed some sedimentation after 24 hours but could be easily resuspended with agitation
  • a gel base made in accordance with the method of Example 7 was provided and 2 parts of Witconol 5909 were added to 78 parts of gel base Then 20 parts of thiabendazole were stirred into the gel
  • the resulting storage formulation was a homogeneous white gel having a viscosity of 7800 cps A pinhole test was performed No dripping was observed The gel was self sealing
  • a dispersion test was performed and the formulation was observed to disperse in less than 2 minutes to form a milky suspension
  • Example 27 At room temperature 2 1 parts Pluronic P 104 were mixed with 73 3 parts gamma-butyrolactone Then 20 9 parts of thiabendazole were stirred into the mixture Then 3 7 parts Aerosil 300 were added with stirring The resulting storage formulation was a milky homogeneous gel having a viscosity of 1200 cps
  • Example 29 50 parts of 2-(thiocyanatomethylthio)benzothiazole (“TCMTB”) and 2 parts Pluronic 104 were heated together at 40 °C until completely molten. To this mixture was added 48 parts of a gel base made in accordance with the method of Example 8. The mixture was stirred while cooling down and the resulting storage formulation was an amber colored homogeneous and clear gel having a viscosity of 1000 cps.
  • TCMTB 2-(thiocyanatomethylthio)benzothiazole

Abstract

PRFnvention concerne un système et un procédé de stockage d'un ingrédient actif tel qu'un pesticide ou un autre type d'agent chimique agricole dans un conditionnement hydrosoluble. L'ingrédient actif est incorporé à une formulation de stockage comprenant un solvant hydrophile non aqueux capable de dissoudre l'ingrédient actif mais pas le conditionnement hydrosoluble. La formulation de stockage comprend facultativement des additifs tels que des agents gélifiants, des tensioactifs et/ou des agents antimoussants.
PCT/US1999/003102 1998-02-25 1999-02-12 Systeme et procede de conditionnement d'une composition chimique WO1999043206A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU32922/99A AU3292299A (en) 1998-02-25 1999-02-12 System and method for packaging a chemical composition
CA002285202A CA2285202A1 (fr) 1998-02-25 1999-02-12 Systeme et procede de conditionnement d'une composition chimique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3028798A 1998-02-25 1998-02-25
US09/030,287 1998-02-25

Publications (1)

Publication Number Publication Date
WO1999043206A1 true WO1999043206A1 (fr) 1999-09-02

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AU (1) AU3292299A (fr)
CA (1) CA2285202A1 (fr)
WO (1) WO1999043206A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010042395A1 (fr) * 2008-10-08 2010-04-15 Wyeth Llc Compositions anthelminthiques à base de benzimidazole
WO2013144147A1 (fr) * 2012-03-28 2013-10-03 Lanxess Deutschland Gmbh Formulations fongicides pour des pvc souples

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112019012702B1 (pt) 2016-12-19 2023-03-28 Upl Limited Embalagem de barreira à umidade

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347220A1 (fr) * 1988-06-15 1989-12-20 Rhone-Poulenc Agriculture Limited Emballage pour liquides
EP0449773A1 (fr) * 1990-03-27 1991-10-02 Ciba-Geigy Ag Concentrés pesticides liquides
WO1992017385A1 (fr) * 1991-04-02 1992-10-15 David Lucas Miles Composition insecticide et unites insecticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347220A1 (fr) * 1988-06-15 1989-12-20 Rhone-Poulenc Agriculture Limited Emballage pour liquides
EP0449773A1 (fr) * 1990-03-27 1991-10-02 Ciba-Geigy Ag Concentrés pesticides liquides
WO1992017385A1 (fr) * 1991-04-02 1992-10-15 David Lucas Miles Composition insecticide et unites insecticides

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010042395A1 (fr) * 2008-10-08 2010-04-15 Wyeth Llc Compositions anthelminthiques à base de benzimidazole
JP2012505218A (ja) * 2008-10-08 2012-03-01 ワイス・エルエルシー ベンゾイミダゾール駆虫組成物
RU2493825C2 (ru) * 2008-10-08 2013-09-27 ВАЙЕТ ЭлЭлСи Бензимидазольные антигельминтные композиции
KR101318603B1 (ko) 2008-10-08 2013-10-15 와이어쓰 엘엘씨 벤즈이미다졸 구충제 조성물
AU2009245834B2 (en) * 2008-10-08 2013-11-14 Zoetis Services Llc Benzimidazole anthelmintic compositions
US9283176B2 (en) 2008-10-08 2016-03-15 Zoetis Services Llc Benzimidazole anthelmintic compositions
WO2013144147A1 (fr) * 2012-03-28 2013-10-03 Lanxess Deutschland Gmbh Formulations fongicides pour des pvc souples
CN104220505A (zh) * 2012-03-28 2014-12-17 朗盛德国有限责任公司 用于增塑pvc的杀真菌剂配制品
US9296878B2 (en) 2012-03-28 2016-03-29 Lanxess Deutschland Gmbh Fungicide formulations for plasticized PVC

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CA2285202A1 (fr) 1999-09-02

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