WO2006105873A2 - Weed control - Google Patents
Weed control Download PDFInfo
- Publication number
- WO2006105873A2 WO2006105873A2 PCT/EP2006/002717 EP2006002717W WO2006105873A2 WO 2006105873 A2 WO2006105873 A2 WO 2006105873A2 EP 2006002717 W EP2006002717 W EP 2006002717W WO 2006105873 A2 WO2006105873 A2 WO 2006105873A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclohexanedione
- benzoyl
- carbon atoms
- derivative
- alkyl
- Prior art date
Links
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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
Definitions
- the present invention relates to a method for selectively controlling weeds in rice, in particular weeds in transplanted and direct-seeded rice, using a 2-benzoyl-l ,3- cyclohexanedione derivative, in particular mesotrione.
- US 5,318,947 discloses a method for controlling harmful plants in rice with 2- benzoyl-l,3-cyclohexanedione derivatives.
- At least one particular 2-benzoyl-l ,3 -cyclohexanedione derivative is highly toxic to rice crop, and in particular indica rice, when applied by conventional methods, i.e. spraying.
- the present invention provides a method for selectively controlling harmful plants in a rice crop, said method comprising applying a 2-benzoyl-l, 3- cyclohexanedione derivative directly into the paddy field water.
- a 2-benzoyl-l, 3- cyclohexanedione derivative is applied by drip application, splash application or distribution of GR formulations.
- Drip application is the direct application of liquid products into the paddy water- generally performed during the last levelling of the rice field.
- Splash application is the application directly into the paddy water by spreading/distributing the chemical either by handhold small bottles or spray guns.
- Solid- Granular formulations are distributed by hand or by machine directly into the paddy field.
- the rice crop comprises an indica- type or japonica-type rice crop; preferably an indica-type rice crop.
- the 2-benzoyl-l, 3-cyclohexanedione derivative is a compound of formula (I)
- X represents a halogen atom; a straight- . or branched-chain alkyl or alkoxy group containing up to six carbon atoms which is optionally substituted by one or more groups -OR 1 or one or more halogen atoms; or a group selected from nitro, cyano, - CO 2 R 2 , -S(O) 1n R 1 , -0(CH 2 ) T OR 1 , -COR 2 , -NR 2 R 3 , -SO 2 NR 2 R 3 , -CONR 2 R 3 , -CSNR 2 R 3 and -OSO 2 R 4 ;
- R 1 represents a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms
- R 2 and R 3 each independently represents a hydrogen atom; or a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms;
- R 4 represents a straight-or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or a cycloalkyl group containing from three to six carbon atoms; each Z independently represents halo, nitro, cyano, S(O) m R 5 , OS(O)JR 5 , C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, Q- ⁇ haloalkoxyQ-ealkyl, carboxy, C 1-6 alkylcarbonyloxy, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbonyl, amino, C 1-6 alkylamino, C 1-6 dialkylamino having independently the stated number of carbon atoms in each alkyl group, C 1-6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, C
- R 5 represents a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms; each Q independently represents C 1-4 alkyl or -CO 2 R 6 wherein R 6 is C 1-4 alkyl; m is zero, one or two; n is zero or an integer from one to four; r is one, two or three; and p is zero or an integer from one to six.
- X is chloro, bromo, nitro, cyano, C 1-4 alkyl, -CF 3 , -S(O) 1n R 1 , or -OR 1 ; each Z is independently chloro, bromo, nitro, cyano, C 1-4 alkyl, -CF 3 , -CH 2 OCH 2 CF 3 , -OR 1 , -OS(O) m R 5 or -S(O) 1n R 5 ; n is one or two; and p is zero.
- the 2-benzoyl-l,3-cyclohexanedione of formula (I) is selected from the group consisting of 2-(2'-nitro-4'-methylsulphonylbenzoyl)-l,3-cyclohexanedione, 2- (2 ' -nitro-4 ' -methylsulphonyloxybenzoyl)- 1 ,3 -cyclohexanedione, 2-(2 ' -chloro-4 ' - methylsulphonylbenzoyl)-l,3-cyclohexanedione, 2-(2'-chloro-3'-trifluoroethoxymethyl- 4'-methylsulphonylbenzoyl)-l ,3-cyclohexanedione, 4,4-dimethyl-2-(4- methanesulphonyl-2-nitrobenzoyl)-l,3-cyclohexanedione, 2-(2-chloro-3-
- the 2-benzoyl- 1 ,3-cyclohexanedione of formula (I) may exist in enolic tautomeric forms that may give rise to geometric isomers. Furthermore, in certain cases, the various substituents may contribute to optical isomerism and/or stereoisomerism. AU such tautomeric forms, racemic mixtures and isomers are included within the scope of the present invention.
- the 2-benzoyl-l,3-cyclohexanedione may be present in either the acid (non- chelated form) or as the metal chelated form.
- the metal chelated form of the 2-benzoyl- 1,3-cyclohexanedione may be made by adding a metal stabilizing salt to the suspoemulsion formulation.
- stabilizing metal salts examples include calcium, beryllium, barium, titanium, magnesium, manganese, zinc, iron, cobalt, nickel and copper salts; most suitable are magnesium, manganese, zinc, iron, cobalt, nickel and copper salts; especially preferred is a copper salt, for example copper hydroxide.
- concentration of stabilizing metal salts in the suspoemulsion formulation of the invention is from 0.01 to 4.0%, and preferably from 0.02 to 1.5%.
- the 2-benzoyl-l,3-cyclohexanedione may be applied in combination with one or more additional active ingredients.
- additional active ingredients include herbicides, fungicides, insecticides and the like.
- a chloroacetamide for example pretilachlor, butachlor, s-metolachlor, acetochlor, alachlor etc., maybe applied in combination with the 2-benzoyl- 1,3- cyclohexanedione.
- the 2-benzoyl- 1 ,3-cyclohexanedione may be applied to the paddy field water either before or shortly after seeding.
- the 2-benzoyl-l,3- cyclohexanedione derivative is applied before seeding or after seeding but pre-emergence of the rice crop.
- the rate at which the 2-benzoyl-l,3-cyclohexanedione derivative is applied will depend on a number of factors, for example the weeds to be controlled, the climatic conditions etc. In general an application rate of between 0.5g ai/ha and 50Og ai/ha is appropriate, for example between 50g and 25Og ai/ha. The specific rate to be applied will be readily determinable by the skilled person.
- the composition Whilst the 2-benzoyl-l,3-cyclohexanedione derivative may be applied alone, in practice, the composition is applied as a formulation containing the various adjuvants and carriers known to or used in the industry for facilitating dispersion. The choice of formulation and mode of application for any given compound may affect its activity, and selection will be made accordingly.
- the herbicidal composition of this invention may be a dustable powder, gel, a wettable powder, a water dispersible granule, a water-dispersable or water-foaming tablet, a briquette, an emulsif ⁇ able concentrate, a microemulsifiable concentrate, an oil-in-water emulsion, a water-in-oil emulsion, a dispersion in water, a dispersion in oil, a suspoemulsion, a soluble liquid (with either water or an organic solvent as the carrier), an impregnated polymer film, or other forms known in the art.
- compositions may be suitable for direct application or may be suitable for dilution prior to application, said dilution being made either with water, liquid fertilizer, micronutrients, biological organisms, oil or solvent.
- the compositions are prepared by admixing the active ingredients with adjuvants including diluents, extenders, carriers, and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, solutions, dispersions or emulsions.
- adjuvants including diluents, extenders, carriers, and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, solutions, dispersions or emulsions.
- an adjuvant such as a finely-divided solid, a mineral oil, a liquid of organic origin, water, various surface active agents or any suitable combination of these.
- the active may also be contained in very fine microcapsules in polymeric substances.
- Microcapsules typically contain the active material enclosed in an inert porous shell which allows escape of the enclosed material to the surrounds at controlled rates.
- Encapsulated droplets are typically about 0.1 to 500 microns in diameter.
- the enclosed material typically constitutes about 25 to 95% of the weight of the capsule.
- the active ingredient may be present as a monolithic solid, as finely dispersed solid particles in either a solid or a liquid, or it may be present as a solution in a suitable solvent.
- Shell membrane materials include natural and synthetic rubbers, cellulosic materials, styrene- butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, other polymers familiar to one skilled in the art, chemically- modified polymers and starch xanthates.
- Alternative very fine microcapsules may be formed wherein the active ingredient is dispersed as finely divided particles within a matrix of solid material, but no shell wall surrounds the microcapsule.
- Suitable agricultural adjuvants and carriers that are useful in preparing the compositions of the invention are well known to those skilled in the art.
- Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropyleneglycol dibenzoate, diprox
- Suitable solid carriers include talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
- a broad range of surface-active agents are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application.
- the surface-active agents can be anionic, cationic, nonionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
- Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol est
- adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emolients, lubricants, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like.
- compositions can also contain other compatible components, for example, other herbicides, herbicide safeners, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like or mixed with sand, or dirt (in the case of solid - granular application).
- other compatible components for example, other herbicides, herbicide safeners, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like or mixed with sand, or dirt (in the case of solid - granular application).
- IR-64- indica rice was directly seeded in muddy soil and herbicide treatment was applied 12 days after the seeding. Treatment was carried out as spray over the top of plants with a 4001/ha spray solution.
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0610512-2A BRPI0610512A2 (pt) | 2005-04-07 | 2006-03-24 | controle de ervas daninhas |
CN2006800107110A CN101150952B (zh) | 2005-04-07 | 2006-03-24 | 杂草防治 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0507093.3 | 2005-04-07 | ||
GBGB0507093.3A GB0507093D0 (en) | 2005-04-07 | 2005-04-07 | Weed control |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2006105873A2 true WO2006105873A2 (en) | 2006-10-12 |
WO2006105873A3 WO2006105873A3 (en) | 2007-04-19 |
WO2006105873A8 WO2006105873A8 (en) | 2007-11-29 |
Family
ID=34586877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/002717 WO2006105873A2 (en) | 2005-04-07 | 2006-03-24 | Weed control |
Country Status (6)
Country | Link |
---|---|
CN (1) | CN101150952B (zh) |
BR (1) | BRPI0610512A2 (zh) |
GB (1) | GB0507093D0 (zh) |
MY (1) | MY145607A (zh) |
TW (1) | TWI383746B (zh) |
WO (1) | WO2006105873A2 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011137922A1 (de) | 2010-05-03 | 2011-11-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100435890C (zh) | 2007-07-10 | 2008-11-26 | 陕西坚瑞化工有限责任公司 | 适用于精密电器设备的气溶胶灭火组合物 |
CN103130575A (zh) * | 2013-03-18 | 2013-06-05 | 哈尔滨利民农化技术有限公司 | 一种用于水稻田的除草剂组合物 |
WO2015153210A1 (en) * | 2014-03-31 | 2015-10-08 | Fmc Corporation | Controlling red rice with mesotrione |
CA2984812C (en) * | 2015-05-07 | 2023-09-26 | Nufarm Australia Limited | Emulsifiable concentrate comprising a phenoxy-alkanoic acid herbicide |
CN106508967A (zh) * | 2016-10-20 | 2017-03-22 | 常州市鼎升环保科技有限公司 | 一种缓释复合除草剂的制备方法 |
KR20230061560A (ko) * | 2017-06-19 | 2023-05-08 | 유피엘 리미티드 | 메소트리온 금속 킬레이트의 다형체 및 제조 공정 |
CN109077049B (zh) * | 2018-07-26 | 2021-04-23 | 李彦民 | 一种防治园林杂草的方法及应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0319075A2 (en) * | 1987-11-28 | 1989-06-07 | Nippon Soda Co., Ltd. | Cyclohexenone derivatives |
WO1991005470A1 (de) * | 1989-10-18 | 1991-05-02 | Hoechst Aktiengesellschaft | Verfahren zur bekämpfung von schadpflanzen in reis |
WO1997041726A1 (en) * | 1996-05-04 | 1997-11-13 | Korea Research Institute Of Chemical Technology | Jumbo formulation comprising pesticides and the process thereof |
-
2005
- 2005-04-07 GB GBGB0507093.3A patent/GB0507093D0/en not_active Ceased
-
2006
- 2006-03-21 TW TW095109616A patent/TWI383746B/zh active
- 2006-03-24 BR BRPI0610512-2A patent/BRPI0610512A2/pt not_active Application Discontinuation
- 2006-03-24 WO PCT/EP2006/002717 patent/WO2006105873A2/en active Application Filing
- 2006-03-24 CN CN2006800107110A patent/CN101150952B/zh active Active
- 2006-03-27 MY MYPI20061345A patent/MY145607A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0319075A2 (en) * | 1987-11-28 | 1989-06-07 | Nippon Soda Co., Ltd. | Cyclohexenone derivatives |
WO1991005470A1 (de) * | 1989-10-18 | 1991-05-02 | Hoechst Aktiengesellschaft | Verfahren zur bekämpfung von schadpflanzen in reis |
WO1997041726A1 (en) * | 1996-05-04 | 1997-11-13 | Korea Research Institute Of Chemical Technology | Jumbo formulation comprising pesticides and the process thereof |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011137922A1 (de) | 2010-05-03 | 2011-11-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
Also Published As
Publication number | Publication date |
---|---|
BRPI0610512A2 (pt) | 2010-06-29 |
CN101150952B (zh) | 2012-01-11 |
TWI383746B (zh) | 2013-02-01 |
TW200721975A (en) | 2007-06-16 |
CN101150952A (zh) | 2008-03-26 |
WO2006105873A8 (en) | 2007-11-29 |
MY145607A (en) | 2012-03-15 |
WO2006105873A3 (en) | 2007-04-19 |
GB0507093D0 (en) | 2005-05-11 |
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