WO1990012503A1 - Water soluble pesticide granules - Google Patents

Water soluble pesticide granules Download PDF

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Publication number
WO1990012503A1
WO1990012503A1 PCT/GB1990/000638 GB9000638W WO9012503A1 WO 1990012503 A1 WO1990012503 A1 WO 1990012503A1 GB 9000638 W GB9000638 W GB 9000638W WO 9012503 A1 WO9012503 A1 WO 9012503A1
Authority
WO
WIPO (PCT)
Prior art keywords
pesticide
weight
parts
composition
aqueous alkali
Prior art date
Application number
PCT/GB1990/000638
Other languages
French (fr)
Inventor
John Misselbrook
Original Assignee
A H Marks & Co 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 A H Marks & Co Ltd filed Critical A H Marks & Co Ltd
Publication of WO1990012503A1 publication Critical patent/WO1990012503A1/en
Priority to GB919121753A priority Critical patent/GB9121753D0/en

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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
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system

Definitions

  • This invention relates to the manufacture of water- soluble pesticide granules in which form dissolution of the pesticide in water is facilitated.
  • the formulation of agricultural products in a soluble form with a high active ingredient content has become an important technology due to the advantages of such products over solvent based formulations, powders and water based suspensions.
  • the technique for producing such formulations involves the agglomeration of a finely divided mixture of the active compound, wetting and dispersing agents, a disintegrant and a diluent. The agglomerate thus formed, is dehydrated and if necessary screened to the required particle size.
  • a method of forming a water soluble pesticide composition comprises the steps of: placing a soluble acidic or phenolic pesticide in a receptacle, adding aqueous alkali to the receptacle to form an alkaline salt of the pesticide, agitating the salt to form a granular composition.
  • the method according to the invention provides a water soluble granular formulation of a pesticide which contains 5-95 parts of active ingredient without the above mentioned drawbacks.
  • the acidic or phonolic pesticide may be provided as a technical grade material in the form of a wet cake. This may be placed in a blender or other agitation apparatus and the aqueous alkali added by spraying or by other menas. Following neutralisation of the wet cake of technical material, further water may be added with controlled shear so that the granulation of the wet powder is achieved.
  • the wet granules so produced may be dried using a fluid bed
  • SUBSTITUTE SHEET homogeneous and lump free powder is produced during the subsequent neutralisation.
  • the aqueous alkali is introduced into a blender slowly via the liquid dispenser to allow uniform coverage of the powder.
  • further controlled shear may be imparted on the wet powder until granulation of the material is effected.
  • the wet granules are then discharged from the blender into a suitable dyrer.
  • a preferred device is a fluid-bed dryer.
  • the granules may be dried at an inlet air temperature of between 50-100°C preferably between 60-65°C, until the moisture content of the granules has been reduced to a suitable level, preferably below 1%
  • the granules containing pesticide may be screened so that the particle size of the product collected is between 100-2000 microns, preferably between 150-1000 microns.
  • Use of this process may provide free-flowing, water soluble granules containing a high level of active pesticide.
  • the product may possess a very high bulk density and readily dissolves in water with some agitation to produce a sprayable solution.
  • a preferred method may produce granules containing 5- 90 parts by weight of bromoxynil (3,5-dibromo-4- hydroxybenzontr-ile) as its sodium salt, 0-10 parts by weight of a disintegrant, preferably modified cross linked cellulose and 0-95 parts by weight of soluble diluent, preferably urea.
  • a disintegrant preferably modified cross linked cellulose and 0-95 parts by weight of soluble diluent, preferably urea.
  • the pesticide may considt of the sodium salt of ioxynil (4-hydroxy-3,5-di-iodobenzonitrile) or may consist of a 1:1 mixture of the sodium salts of ioxynil and bromoxynil .
  • the invention may also provide a composition
  • a composition comprising 5-90 parts by weight of bromoxynil as its sodium salt, 0-10 parts by weight of a disintegrant, preferably modified cross linked cellulose and 0-95 parts by weight of a soluble diluent, preferably urea, as free flowing
  • SUBSTITUTE SHEET dryer Other methods of drying may be used although fluid bed drying is preferred.
  • the dried granules containing pesticide may be screened to obtain the desired particle size.
  • the granules contained are free flowing and readily soluble in water, forming a clear sprayable solution.
  • the alkali is preferably sodium hydroxide although potassium hydroxide, sodium carbonate, sodium bicarbonate or ammonia may be employed.
  • the aqueous phase may consist of a solution containing between 20-60% of sodium hydroxide, preferably 40-50%. The proportions given in this specifica ion are by weight unless otherwise indicated. An appropriate amount of alkali is employed to completely neutralise the wet cake of pesticide.
  • the solution may be prepared by slowly adding solid sodium hydroxide pellets to a body of water with moderate agitation. The agitation is continued until a homogenous solution is obtained. A wetting agent can be introduced at this time is required. Care should be taken during the dissolution process to avoid the generation of excessive heat .
  • the wetting agent if employed, is preferably a non- ionic surfactant.
  • Octyl phenyl ethoxylates particularly having 8-10 ethylene oxide units, are preferred.
  • An amount of 0 to 10 parts preferably 1 to 2 parts is preferred.
  • a disintegrant may be employed, preferably in an amount of 0 to 10 parts to more preferably 5 to 8 parts.
  • the disintegrant may be selected from bentonite, or crosslinked modified starch. Use of bentonite is preferred.
  • the dispersant may be present in an amount of 0 to 10, preferably 3 to 5 parts.
  • the wet cake technical grade pesticide is added to a suitable liquid/solids blender with a liquid disperser fitted to allow the sodium hydroxide solution to be added uniformly to the solid material. The disintegrant is added to the powder and blended for a few minutes to ensure a
  • the pesticide may alternatively consist of the sodium salt of ioxynil or a 1:1 mixture of ioxynil and bromoxyni1.
  • the product may be obtained directly from the wet cake intermdiate and that the neutralisation is successfully carried out as a dry reation which also produces the water soluble pesticide salt in a desirable non-dusty form without additional processing steps.
  • the method described in this invention is especially useful in producing a water soluble granule formulation of bromoxynil as its sodium salt, for the control of many species of weeds.
  • the formulation produced avoids the use of solvents which could cause toxicological concern and produce hazards for both the environment and the worker.
  • the wet granules were dried in a fluid bed dryer for 10 minutes at 60°C and the sieve fraction between 150-500 microns was collected.
  • This product exhibits excellent properties on dilution in water, wetting almost instantly and producing a stable solution on standing.
  • the wet granules were dried in a fluid bed dryer for ⁇ loU lightningmi..n_,u. . t-e..s,_. a,t- coUnoC and the sieve fraction between 150-500 microns was collected.
  • the product exhibits excellent properties on dilution in water, wetting almost instantly, producing a stable solution on standing, stirred until a homogenous mixture is obtained.

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

A method of forming a water soluble granular pesticide composition comprises the steps of placing ioxinyl or bromoxinyl or mixtures thereof in a receptacle, adding aqueous alkali and agitating to form a granular composition.

Description

WATER SOLUBLE PESTICIDE GRANULES
This invention relates to the manufacture of water- soluble pesticide granules in which form dissolution of the pesticide in water is facilitated.
The formulation of agricultural products in a soluble form with a high active ingredient content, known as water dispersable or water soluble granules has become an important technology due to the advantages of such products over solvent based formulations, powders and water based suspensions. The technique for producing such formulations involves the agglomeration of a finely divided mixture of the active compound, wetting and dispersing agents, a disintegrant and a diluent. The agglomerate thus formed, is dehydrated and if necessary screened to the required particle size.
According to the present invention a method of forming a water soluble pesticide composition comprises the steps of: placing a soluble acidic or phenolic pesticide in a receptacle, adding aqueous alkali to the receptacle to form an alkaline salt of the pesticide, agitating the salt to form a granular composition.
The method according to the invention provides a water soluble granular formulation of a pesticide which contains 5-95 parts of active ingredient without the above mentioned drawbacks.
The acidic or phonolic pesticide may be provided as a technical grade material in the form of a wet cake. This may be placed in a blender or other agitation apparatus and the aqueous alkali added by spraying or by other menas. Following neutralisation of the wet cake of technical material, further water may be added with controlled shear so that the granulation of the wet powder is achieved. The wet granules so produced, may be dried using a fluid bed
SUBSTITUTE SHEET homogeneous and lump free powder is produced during the subsequent neutralisation. The aqueous alkali is introduced into a blender slowly via the liquid dispenser to allow uniform coverage of the powder. After addition of the neutralising solution, further controlled shear may be imparted on the wet powder until granulation of the material is effected.
The wet granules are then discharged from the blender into a suitable dyrer. A preferred device is a fluid-bed dryer. The granules may be dried at an inlet air temperature of between 50-100°C preferably between 60-65°C, until the moisture content of the granules has been reduced to a suitable level, preferably below 1%
The granules containing pesticide may be screened so that the particle size of the product collected is between 100-2000 microns, preferably between 150-1000 microns.
Use of this process may provide free-flowing, water soluble granules containing a high level of active pesticide. The product may possess a very high bulk density and readily dissolves in water with some agitation to produce a sprayable solution.
A preferred method may produce granules containing 5- 90 parts by weight of bromoxynil (3,5-dibromo-4- hydroxybenzontr-ile) as its sodium salt, 0-10 parts by weight of a disintegrant, preferably modified cross linked cellulose and 0-95 parts by weight of soluble diluent, preferably urea.
Alternatively, the pesticide may considt of the sodium salt of ioxynil (4-hydroxy-3,5-di-iodobenzonitrile) or may consist of a 1:1 mixture of the sodium salts of ioxynil and bromoxynil .
The invention may also provide a composition comprising 5-90 parts by weight of bromoxynil as its sodium salt, 0-10 parts by weight of a disintegrant, preferably modified cross linked cellulose and 0-95 parts by weight of a soluble diluent, preferably urea, as free flowing
SUBSTITUTE SHEET dryer. Other methods of drying may be used although fluid bed drying is preferred. The dried granules containing pesticide may be screened to obtain the desired particle size. The granules contained are free flowing and readily soluble in water, forming a clear sprayable solution. The alkali is preferably sodium hydroxide although potassium hydroxide, sodium carbonate, sodium bicarbonate or ammonia may be employed.
The aqueous phase may consist of a solution containing between 20-60% of sodium hydroxide, preferably 40-50%. The proportions given in this specifica ion are by weight unless otherwise indicated. An appropriate amount of alkali is employed to completely neutralise the wet cake of pesticide.
The solution may be prepared by slowly adding solid sodium hydroxide pellets to a body of water with moderate agitation. The agitation is continued until a homogenous solution is obtained. A wetting agent can be introduced at this time is required. Care should be taken during the dissolution process to avoid the generation of excessive heat .
The wetting agent, if employed, is preferably a non- ionic surfactant. Octyl phenyl ethoxylates, particularly having 8-10 ethylene oxide units, are preferred. An amount of 0 to 10 parts preferably 1 to 2 parts is preferred.
A disintegrant may be employed, preferably in an amount of 0 to 10 parts to more preferably 5 to 8 parts. The disintegrant may be selected from bentonite, or crosslinked modified starch. Use of bentonite is preferred. The dispersant may be present in an amount of 0 to 10, preferably 3 to 5 parts. In a preferred method, the wet cake technical grade pesticide is added to a suitable liquid/solids blender with a liquid disperser fitted to allow the sodium hydroxide solution to be added uniformly to the solid material. The disintegrant is added to the powder and blended for a few minutes to ensure a
SUBSTITUTE SHEET granules. The pesticide may alternatively consist of the sodium salt of ioxynil or a 1:1 mixture of ioxynil and bromoxyni1.
It is surprising that the product may be obtained directly from the wet cake intermdiate and that the neutralisation is successfully carried out as a dry reation which also produces the water soluble pesticide salt in a desirable non-dusty form without additional processing steps.
Therefore the method described in this invention is especially useful in producing a water soluble granule formulation of bromoxynil as its sodium salt, for the control of many species of weeds. The formulation produced avoids the use of solvents which could cause toxicological concern and produce hazards for both the environment and the worker.
The following examples illustrate the invention: EXAMPLE 1
75.90g of water was placed in a beaker and to this was slowly added 75.90g of sodium hydroxide pellets. The mixture was agitated until the sodium hydroxide was completely dissolved, and to this was added 11.36g of Hyonic PE90 (octyl phenol ethoxylate) .
600.OOg of wet cake bromoxynil (3,5-dibromo-4-hydroxy- benzonitrile) was weighed into the blender and agitated to reduce the amount of agglomerates present. The aqueous sodium hydroxide solution was sprayed onto the powder under agitation until neutralisation was complete. Further controlled shear was applied to the powder until granulation has occurred.
The wet granules were dried in a fluid bed dryer for 10 minutes at 60°C and the sieve fraction between 150-500 microns was collected.
This product exhibits excellent properties on dilution in water, wetting almost instantly and producing a stable solution on standing.
SUBSTITUTE SHEET EXAMPLE 2
65.06g of water was placed in a beaker and to this was slowly added 39.46g of sodium hydroxide pellets. The mixture was agitated until the sodium hydroxide completely dissolved and 1 . 10 of Hyonic PE90 (octyl phenyl ethoxylate) was added.
600.OOg of wet cake ioxynil (4-hydroxy-3,5, -di- iodobenzontrile) was weighed into the blender and agitated to reduce the amount of agglomerates present. The aqueous sodium hydroxide solution was sprayed onto the powder with agitation until neutralisation was complete. Further controlled shear together with additional water was applied to the powder until granulation had occurred.
The wet granules were dried in a fluid bed dryer for ιloU „mi..n_,u..t-e..s,_. a,t- coUnoC and the sieve fraction between 150-500 microns was collected.
The product exhibits excellent properties on dilution in water, wetting almost instantly, producing a stable solution on standing, stirred until a homogenous mixture is obtained.
SUBSTITUTE SHEET

Claims

1. A method of forming a water soluble pesticide composition comprising the steps of: placing a soluble acidic or phenolic pesticide in a receptacle, adding aqueous alkali to the receptacle to form an alkaline salt of the pesticide, and agitating the salt to form a granular composition.
2. A method as claimed in claim 1 wherein the pesticide is provided in a form of a wet cake.
3. A method as claimed in any preceding claim wherein the granular composition is dried using a fluid bed drier.
4. A method as claimed in any preceding claim wherein the aqueous alkali comprises 20 - 60% by weight sodium hydroxide.
5. A method as claimed in claim 4 wherein the aqueous alkali comprises 40 - 50% by weight sodium hydroxide.
6. A method as claimed in any preceding claim wherein a wetting agent is added to the aqueous alkali.
7. A method as claimed in claim 6 wherein the wetting agent is octyle phenyl ethoxylate.
8. A method as claimed in any preceding claim wherein a disintigrant is added to the mixture.
9. A method as claimed in claim 8 wherein 0 - 10 parts by weight of the disintegrant are used.
10. A method, as claimed in claim 9 wherein 5 - 8 parts by weight of the disintegrant are used.
11. A method as claimed in any of claims 8 to 10 wherein the disintigrant is selected from: bentonite or cross-linked modified starch.
12. A method as claimed in any preceding claim wherein the pesticide is selected from: bromoxynil, ioxynil or a mixture thereof.
13. A free flowing granular composition comprising 5 - 90 parts by weight of a pesticide, 0 - 10 parts by weight
SUBSTITUTE SHEET of a disintegrant and 0 - 95 parts by weight of a soluble diluent, wherein the pesticide is selected from: the sodium salt of bromoxynil, the sodium salt of ioxynil or mixtures thereof.
14. A composition as claimed in claim 13 wherein the disintigrant is modified cross-linked cellulose.
15. A composition as claimed in claim 13 or 14 wherein the soluble diluent is urea.
SUBSTITUTE SHEET
PCT/GB1990/000638 1989-04-25 1990-04-25 Water soluble pesticide granules WO1990012503A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB919121753A GB9121753D0 (en) 1989-04-25 1991-10-14 Water soluble pesticide granules

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898909380A GB8909380D0 (en) 1989-04-25 1989-04-25 Water soluble pesticide solution
GB8909380.1 1989-04-25

Publications (1)

Publication Number Publication Date
WO1990012503A1 true WO1990012503A1 (en) 1990-11-01

Family

ID=10655662

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1990/000638 WO1990012503A1 (en) 1989-04-25 1990-04-25 Water soluble pesticide granules

Country Status (3)

Country Link
AU (1) AU5527690A (en)
GB (1) GB8909380D0 (en)
WO (1) WO1990012503A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995008265A1 (en) * 1993-09-23 1995-03-30 E.I. Du Pont De Nemours And Company Water-dispersible granular agricultural compositions made by heat extrusion
US6387388B1 (en) 1995-11-08 2002-05-14 Merck & Co., Inc. Pesticidal formulation
BG64469B1 (en) * 1995-11-08 2005-04-30 Merck & Co. Inc. Pesticidal form
US8404259B2 (en) * 2005-10-11 2013-03-26 The National Lime And Stone Co. Dispersible granular substrate for pesticide delivery

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1022164A (en) * 1962-07-31 1966-03-09 Shell Res Ltd Manufacture of herbicidally active granules
GB1067032A (en) * 1962-09-24 1967-04-26 May & Baker Ltd 4-hydroxybenzonitrile derivatives
DE1906399A1 (en) * 1969-02-08 1970-08-27 Hoechst Ag Process for the continuous production of salts
EP0238240A2 (en) * 1986-03-20 1987-09-23 UNIROYAL CHEMICAL COMPANY, Inc. Dry reactive processing
GB2218634A (en) * 1988-05-16 1989-11-22 Allied Colloids Ltd Granular pesticidal compositions
EP0368806A1 (en) * 1988-11-10 1990-05-16 Ciba-Geigy Ag Solid herbicidal formulations

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1022164A (en) * 1962-07-31 1966-03-09 Shell Res Ltd Manufacture of herbicidally active granules
GB1067032A (en) * 1962-09-24 1967-04-26 May & Baker Ltd 4-hydroxybenzonitrile derivatives
DE1906399A1 (en) * 1969-02-08 1970-08-27 Hoechst Ag Process for the continuous production of salts
EP0238240A2 (en) * 1986-03-20 1987-09-23 UNIROYAL CHEMICAL COMPANY, Inc. Dry reactive processing
GB2218634A (en) * 1988-05-16 1989-11-22 Allied Colloids Ltd Granular pesticidal compositions
EP0368806A1 (en) * 1988-11-10 1990-05-16 Ciba-Geigy Ag Solid herbicidal formulations

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995008265A1 (en) * 1993-09-23 1995-03-30 E.I. Du Pont De Nemours And Company Water-dispersible granular agricultural compositions made by heat extrusion
US5714157A (en) * 1993-09-23 1998-02-03 E. I. Du Pont De Nemours And Company Water-dispersible granular agricultural compositions made by heat extrusion
CN1102336C (en) * 1993-09-23 2003-03-05 纳幕尔杜邦公司 Water-dispersible granular agricultural compositions made by heat exhaustion
US6387388B1 (en) 1995-11-08 2002-05-14 Merck & Co., Inc. Pesticidal formulation
BG64469B1 (en) * 1995-11-08 2005-04-30 Merck & Co. Inc. Pesticidal form
US8404259B2 (en) * 2005-10-11 2013-03-26 The National Lime And Stone Co. Dispersible granular substrate for pesticide delivery

Also Published As

Publication number Publication date
AU5527690A (en) 1990-11-16
GB8909380D0 (en) 1989-06-14

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