EP1793666A1 - Préparation herbicide - Google Patents

Préparation herbicide

Info

Publication number
EP1793666A1
EP1793666A1 EP20050787521 EP05787521A EP1793666A1 EP 1793666 A1 EP1793666 A1 EP 1793666A1 EP 20050787521 EP20050787521 EP 20050787521 EP 05787521 A EP05787521 A EP 05787521A EP 1793666 A1 EP1793666 A1 EP 1793666A1
Authority
EP
European Patent Office
Prior art keywords
group
branched
alkyl
herbicide
general formula
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP20050787521
Other languages
German (de)
English (en)
Inventor
T. c/o Kao Corporation Research Laboratories SUZUKI
Akio c/o Kao Corporation Research Laboratories MANBA
H PT.Kao Indo.Chm Jalan Raya Tambun KM PRASETYO
PT.Kao Indo.Chm. Jalan Raya Tambun KM HERMAWANTO
PT.Kao Indon.Chem. Jalan R.Tambun KM Suharyanto
S. PT.Kao Indon.Chem. Jalan R.Tambun KM MULJATI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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 Kao Corp filed Critical Kao Corp
Publication of EP1793666A1 publication Critical patent/EP1793666A1/fr
Withdrawn legal-status Critical Current

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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the present invention relates to a herbicide composition containing an amino acid-based herbicide.
  • Agrochemicals including herbicides are used in the form of preparations such as emulsion, wettable powder, particle or granule, powder, flowable etc.
  • preparations such as emulsion, wettable powder, particle or granule, powder, flowable etc.
  • various measures have been made for physical properties of preparation forms, but unde ⁇ r the present circumstances, further enhancement of the effect of agrochemicals bydevisingpharmaceutical forms is difficult .
  • development of novel agrochemicals is further difficult, further enhancement of the activity of existing agrochemicals would be significantly meaningful in industry .
  • JP-A (W) 9-506615 discloses use of specific secondary or tertiary alcohol-based surfactants in order to improve rain resistance of herbicides such as glyphosate .
  • the present invention relates to a herbicide composition containing (A) an amino acid-based herbicide [referred to hereinafter as component (A) ] and (B) a compound represented by the following general formula (1) [referred to hereinafter as component (B) ] :
  • R 1 represents a C3 to C29 branched alkyl or branched alkenyl group
  • R 2 represents a C2 to C4 alkylene group
  • n is a mean number in the range of 1 to 30.
  • the present invention also relates to an efficacy enhancer for a herbicide, which contains a compound represented by the general formula (1) or an efficacy enhancer composition for a herbicide, which containing the same.
  • the present invention also relates to a method of weeding by applying the herbicide composition onto a plant to be controlled, use of the herbicide composition as a herbicide, a method of enhancing the efficacy of a herbicide by the compound (B) or a composition containing the same, or use of the compound (B) or a composition containing the same in enhancing the efficacy of a herbicide.
  • the present invention provides a herbicide composition containing an amino acid-based herbicide excellent in wetting properties and permeability and also in a weeding effect.
  • the active ingredient (agrochemical material) of the amino acid-based herbicide includes glyphosate [N- (phosphonomethyl) glycine or its salt] , Bialaphos [sodium salt of L-2-amino-4- [ (hydroxy) (methyl) phosphinoyl] butyryl-L- alanyl-L-alanine] and gluphosinate [ammonium-DL- homoalanin-4-yl (methyl) phoshinate] , and these may be agriculturally acceptable salts.
  • glyphosate N- (phosphonomethyl) glycine or its salt
  • Bialaphos sodium salt of L-2-amino-4- [ (hydroxy) (methyl) phosphinoyl] butyryl-L- alanyl-L-alanine]
  • gluphosinate ammonium-DL- homoalanin-4-yl (methyl) phoshinate
  • the component (B) is a compound represented by the general formula (1) above.
  • R 1 is preferably a C5 to C29 branched alkyl or branched alkenyl group, particularly preferably a C7 to C21 branched alkyl group.
  • R 2 S are preferably C2 and C3 alkylene groups or C2 alkylene groups, and n is a mean number in the range of 6 to 20.
  • the compound (B) is preferably a compound represented fc>y the following general formula (1') :
  • R 1 represents a C3 to C29 branched alkyl or branched alkenyl group
  • R 2a and R 2b each represent a C2 to C4 alkylene group, and are not simultaneously the same
  • -(R 2 O) n - or -(R 23 O) J (R 213 O) 15 - is preferably one or two blocks of an oxyethylene group and/or an oxypropylene group .
  • R 1 CH 2 - ⁇ s preferably a C6 to C30 branched alkyl or branched alkenyl group, more preferably a C8 to C22 branched alkyl group.
  • the branched chain type of R 1 CH 2 - is Guerbet, iso, multi-branch, more preferably Guerbet or iso, still more preferably Guerbet.
  • R 1 CH 2 - include a 2-ethylhexyl group, isotridecyl group, isodecyl group, C28 Guerbet -alkyl group, isostearyl group, 2-octyldodecyl group etc., among which the 2-ethylhexyl group, isotridecyl group and isodecyl group are preferable, and particularly the 2-ethylhexyl group is preferable.
  • R 2a 0 and R 2b 0 are added in a block form, and are preferably a C2 oxyalkylene group (also called an oxyethylene group) /C3 oxyalkylene (also called an oxypropylene group) mixture or C2 oxyalkylene groups. It is particularly preferable that R 2a is a C3 alkylene group and R 2b is a C2 alkylene group, or R 2a or R 2b is a C2 alkylene group, j + k is a mean value preferably in the range of 6 to 20. ⁇ Herbicide composition>
  • the herbicide composition of the present invention contains the component (A) in an amount of preferably 0.1 to 80% by weight, more preferably 1 to 60% by weight as an agrochemical material (herbicidal active ingredient) contained in an amino acid-based herbicide.
  • the component (B) is contained in an amount of preferably 0.01 to 50% by weight, more preferably 0.1 to 20% by weight.
  • the herbicide composition of the present invention is preparedby suitably selecting the type and amount of the active ingredient incorporated, depending on conditions in an application place, etc.
  • the herbicide composition of the present invention contains the active ingredients in a total amount [total amount of the component (A) (as raw material) and the component (B)] of preferably 0.1 to 90% by weight, more preferably 0.5 to 80% by weight, still more preferably 1 to 70% by weight.
  • the mixing ratio of the active ingredients can be selected in a considerably broad range, and. for example the weight ratio of the component (A) to the component (B) , that is, (A) / (B) , can be from 100/1 to 1/100, particularly 50/1 to 1/50, especially 20/1 to 1/20. In this weight ratio, the amount of the component (A) is the amount of the agrochemical material (active ingredient of the herbicide) contained in the amino acid-based herbicide.
  • the herbicide composition of the present invention further contains at least one surfactant selected from the group consisting of (C) a cationic surfactant, an anionic surfactant and an amphoteric surfactant (referred to hereinafter as component (C) ) .
  • component (C) a cationic surfactant, an anionic surfactant and an amphoteric surfactant
  • the cationic surfactant is at least one member selected from the group consisting of a quaternary ammonium salt represented by the general formula (2) :
  • R 3 represents a C8 to C30 branched or linear alkyl or alkenyl group
  • R 4 and R 5 each represent a hydrogen atom, a Cl to C3 alkyl group or - (A 1 O) 1n H
  • a 1 represents a C2 to C4 alkylene group
  • m is a mean number in the range of 1 to 15
  • R 6 represents a Cl to C30 branched or linear alkyl or alkenyl group or a benzyl group
  • (X 1 ) " is a counterion, and a tertiary amine represented by the following general formula (3) :
  • R 7 represents a Cl to C30 branched or linear alkyl or alkenyl group
  • a 2 represents a C2 to C4 alkylene group
  • p is a means number in the range of 1 to 15
  • q is a mean number in the range of 1 to 15
  • p + q is 2 to 30.
  • the cationic surfactant represented by the general formula (2) is particularly preferably monoalkyl (preferably C8 to C18, particularly preferably C12 to C14) benzyl dimethyl ammonium chloride, polyoxyal ⁇ cylene monoalkyl (preferably C8 to C18, particularly preferably C12 to C18, and p + q is preferably 2 to 20, particularly preferably p + q is 2 to 15) monomethyl ammonium chloride, dialkyl (preferably C8 to C18, particularlypreferably ClO to C14) dimethyl ammonium chloride, monoalkyl (preferably C8 to C18, particularly preferably C12 to C18) trimethyl ammonium c ⁇ iloride, or polyoxyalkylene monoalkyl (preferably C8 to C18, particularly preferably C12 to C14, and preferably p + q is 2 to 20, and particularly preferably p + q is 2 to 15) benzyl ammonium chloride.
  • the counterion is preferably a halogen ion or an alky
  • the anionic surfactant includes sodium mono- and di ⁇ alkyl naphthalene sulfonates, sodium ⁇ -olefin sulfonates, sodium alkane sulfonate, alkyl sulfosuccinates, alkyl sulfates, polyoxyalkylene alkyl ether sulfates, polyoxyalkylene alkyl aryl ether sulfates, polyoxyalkylene styryl phenyl ether sulfates, mono- and di-alkyl benzene sulfonates, alkyl naphthalene sulfonates, alkyl naphthalene sulfonate/formaldehyde condensates, aILkyl diphenyl ether sulfonates, olefinic sulfonates, mono- and di-alkyl phosphates, polyoxyalkylene mono- and di-alkyl phosphat
  • the anionic surfactant is at least one member selected from the group consisting of an alkyl sulfonate represented by the following general fformula (4) :
  • R 8 represents a C6 to C30 branched or linear alkyl or alkenyl group
  • (M 1 ) * is a counterion, an ether acetate represented by the following general formula (5) : R 9 O (A 3 O ) r CH,COO ⁇ (M 2 ) ( 5 )
  • R 9 represents a C6 to C30 branched or linear alkyl or alkenyl group
  • a 3 represents a C2 to C4 alkylene group
  • r is a mean number in the range of 1 to 30
  • (M 2 )" is a counterion
  • R 10 represents a C6 to C30 branched or linear alkyl or alkenyl group
  • a 4 represents a C2 to C4 alkylene group
  • t is a mean number in the range of 0 to 30, and (M 3 ) + is a counterion.
  • the anionic surfactant of the general formula (4) is particularly preferably an alkyl benzene sulfonate.
  • the anionic surfactant of the general formula (5) is particularly preferably a polyoxyethylene alkyL ether acetate.
  • the anionic surfactant of the general formula (6) is particularly preferably a polyoxyethylene alkyL ether sulfate.
  • the amphoteric surfactant is at least one member selected from the group consisting of an aZLkyl hydroxy sulfobetaine represented by the following general formula (7) : (7)
  • R 11 represents a C6 to C30 branched or linear alkyl or alkenyl group, a 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolium betaine represented by the following formula (8) :
  • R 12 represents a C6 to C30 branched or linear alkyl or alkenyl group, an amide propyl betaine represented by the following general formula (9) :
  • R 13 represents a C6 to C30 branched or linear alkyl or alkenyl group
  • R 13a and R 13b each represent a methyl group or (A 5 O) V H
  • a 5 is a C2 to C4 alkylene group
  • v is a mean number in the range of 1 to 30, and an alkyl acetic acidbetaine representedby the following general formula (10) :
  • R 14 represents a C6 to C30 branched or linear alkyl or alkenyl group
  • R 14a and R 14b each represent a methyl group or (A 6 O) W H
  • a 6 represents a C2 to C4 alkylene group
  • w is a mean number in the range of 1 to 30.
  • R 11 is preferably a C8 to C18 group, more preferably a C12 to C14 group.
  • R 12 is preferably a C8 to C18 group, more preferably a C12 to C14 group.
  • R 13 is preferably a C8 to C18 group, more preferably a C12 to C14 group, and each of R 13a and R 13b is preferably a methyl group.
  • R 14 is preferably a C8 to C18 group, more preferably a C12 to C14 group, and each of R 14a and R 14b is preferably a methyl group.
  • the herbicide composition of the present invention preferably contains the component (C) in an amount of 0.01 to 80% by weight, particularly 0.1 to 50% by weight.
  • a pH adjusting agent, inorganic salts and a thickener may be added to the herbicide composition of the present invention.
  • the pH adjusting agent which can be used in the present invention is citric acid, phosphoric acid (pyrophosphoric acid) , gluconic acid, or salts thereof.
  • the inorganic salts which can be used in the present invention include inorganic ammonium salts such as ammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium thiocyanate, ammonium chloride and ammonium sulfamate.
  • the raw chemical itself is applied as it is, or is mixed with carriers and other additives if necessary for use in preparation forms usually used as herbicides, for example in forms such as powder, coarse powder, fine particle, particle, wetting agent, granular wetting agent, emulsion, liquid, aqueous solution, water-soluble agent (so-called jumbo agent) , flowable agent, microcapsule, oil suspension etc.
  • these preparations can also be mixed with a plurality of other herbicides, insecticides, bactericides, plant growth regulators and fertilizers.
  • Thepreparation canbe compounded particularly with one or more kinds of other herbicides to broaden its herbicidal spectrum or maintain its efficacy for a longer time.
  • the solid carriers usable for preparing the herbicide composition of the present invention include, for example, inorganic materials such as clays represented by kaolinite, montmorilonite or attapulgite, and talc, mica, chemical agalmatolite, fluorite, vermiculite gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium, lime, calcium phosphate, zeolite, anhydrous silicic acid, synthetic silicic acid, calcium, etc.; vegetable organic materials such as soybean powder, tobacco powder, walnut powder, wheat powder, wood powder, soybean flour, starch, crystalline cellulose, etc.; inorganic or organic substances such as potassium chloride, sodium chloride, ammonium chloride, ammonium sulfate, ammonium nitrate, urea, citric acid, sodium citrate, sodium tartrate, glucose, fructose, etc.; synthetic or natural polymer compounds such as chroman resin, petroleum resin, alkyd resin, polyvinyl chloride, polyal
  • the liquid carrier which can be used in preparing the herbicide composition of the present invention includes paraffin- or naphthyne-based hydrocarbons such as kerosine, mineral oil, spindle oil, white oil, etc.; alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol, etc.; ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, etc.; fatty alcohol esters such as methyl oleate, butyl oleate, isopropyl myristate, palm fatty acid, etc.; polybasic alcohol esters such as diisobutyl adipate, ditridecyl phthalate, dialkyl (C10-C12) phthalate, dialkyl ⁇ C8, ClO) phthalate, etc.;
  • water-soluble polymers and surfactants such as the surfactant as component (C) and nonionic surfactants other than component (B) can be used.
  • the water-soluble polymers include, for example, polyvinyl alcohol, carboxymethyl cellulose, alginate, polyacrylate, starch, enzymatically decomposed dextrin, or isobutyl maleate copolymers salts (Na salt, K salt, Ca salt, ammonium salt, various amine salts etc.
  • a cationic surfactant and an amphoteric surfactant can also be used.
  • the surfactants described above can be used alone or as a mixture of two or more thereof.
  • the granular composition may be compounded if necessary with suitable amounts of other additives used usually in agrochemicals, for example with a spreading agent, a preservative, an emulsifier, a decomposition inhibitor, a solidification inhibitor, an activity enhancer (for example, soybean lecithin or vegetable oil) etc., and if necessary mixed with, and used in combination with, agrochemical components such as insecticides, miticides, nematocides, bactericides, antiviral agents, inducers, plant growth regulators, fertilizers etc.
  • agrochemical components such as insecticides, miticides, nematocides, bactericides, antiviral agents, inducers, plant growth regulators, fertilizers etc.
  • an efficacy enhancer composition for a herbicide particularly an amino acid-based herbicide which further contains the components (B) and (C) described above.
  • the component (B) is contained in an amount of preferably 0.01 to 50% by weight, more preferably 0.1 to 20% by weight
  • the component (C) is contained in an amount of preferably 0.01 to 80% by weight, more preferably 0.1 to 50% by weight, the balance being water.
  • the efficacy enhancer compositions (Nos . 1 to 19) used in the Examples and Comparative Examples below were prepared from the component (B) , component (C) etc. shown in Table 1.
  • POE is an abbreviation of polyoxyethylene
  • POP is an abbreviation of polyoxypropylene
  • the number in the brackets is the average number of units added.
  • Ethylene oxide (referred to hereinafter as EO) adduct (average number of EO units added: 12) of Isotridecanol (trade name: Exxal 13 manufactured by Exxon Mobile) *2 : EO adduct (average number of EO units added: 7) of Isodecanol (trade name: Decanol manufactured by Kyowa Hakko Chemical)
  • Herbicide compositions glyphosate preparations containing 10 wt% efficacy enhancers in Table 1 and 41 wt% glyphosate isopropyl amine salt, the balance being water (distilled water) , were prepared.
  • the permeability and herbicidal efficacy were evaluated by the following methods. ⁇ Permeability>
  • the weight of the crabgrass over the ground was measured 10 days after the spraying treatment and a herbicidal ratio (%) was determined in relation to the weight of the crabgrass over the ground in an untreated group.
  • the herbicidal iratio by each preparation is shown in Table 3.
  • Herbicide compositions containing 10 wt% efficacy enhancer in Table 1 and 18.5 wt% glyphosate, the balance being water (distilled water) , were prepared, and the herbicidal efficacy test (herbicidal ratio) was conducted in the same manner as in Example 1. The results are shown in Table 4.
  • Table 4 Herbicide compositions (gILyphosate preparations) containing 10 wt% efficacy enhancer in Table 1 and 18.5 wt% glyphosate, the balance being water (distilled water) , were prepared, and the herbicidal efficacy test (herbicidal ratio) was conducted in the same manner as in Example 1. The results are shown in Table 4. Table 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

La présente invention a pour objet une préparation herbicide contenant (A) un herbicide basé sur un acide aminé et (B) un composé de structure ramifiée représenté par la formule (1) : R1CH2O-(R2O)nH (1) où R1 représente une chaîne ramifiée alkyle ou alkényle en C3-C29, R2 représente un groupement alkylène en C2-C4, et n est un nombre moyen compris entre 1 et 30.
EP20050787521 2004-09-27 2005-09-27 Préparation herbicide Withdrawn EP1793666A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004278837 2004-09-27
PCT/JP2005/018254 WO2006035983A1 (fr) 2004-09-27 2005-09-27 Préparation herbicide

Publications (1)

Publication Number Publication Date
EP1793666A1 true EP1793666A1 (fr) 2007-06-13

Family

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Family Applications (1)

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EP20050787521 Withdrawn EP1793666A1 (fr) 2004-09-27 2005-09-27 Préparation herbicide

Country Status (5)

Country Link
EP (1) EP1793666A1 (fr)
CN (2) CN101014243B (fr)
AU (1) AU2005288013B2 (fr)
MY (2) MY157730A (fr)
WO (1) WO2006035983A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ598571A (en) * 2005-11-14 2013-04-26 Rhodia Surfactant is alkoxylated alcohol in an agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
AU2013224661B2 (en) * 2005-11-14 2015-05-28 Specialty Operations France Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
BRPI0818808A2 (pt) * 2007-11-07 2014-10-07 Rhodia Operations Composição aquosa herbicida, processo para preparar a mesma, e, mistura.
EP2457890A1 (fr) 2010-11-29 2012-05-30 Cognis IP Management GmbH Compositions de biocide comportant des produits d'alkoxylation de dérivés de l'alcool isoamylique
TWI561170B (en) * 2010-12-21 2016-12-11 Meiji Seika Pharma Co Ltd Stabilized liquid aqueous crop protection composition

Citations (1)

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Publication number Priority date Publication date Assignee Title
WO1999051099A1 (fr) * 1998-04-03 1999-10-14 Monsanto Company Combinaison de glyphosate et d'un herbicide triazolinone

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Publication number Priority date Publication date Assignee Title
GB9322806D0 (en) * 1993-11-05 1993-12-22 Dow Europ Sa Aqueous alkaline composition
ATE175542T1 (de) 1993-12-17 1999-01-15 Monsanto Co Verbesserte wirksamkeit und/oder regenfestigkeit an pestizide formulierungen aufweisende tenside
GB9412722D0 (en) * 1994-06-24 1994-08-17 Zeneca Ltd Herbicidal composition
EP0854676A4 (fr) * 1995-06-16 2000-03-15 Monsanto Co Tensioactifs ameliorant l'efficacite et/ou la resistance a l'entrainement par la pluie de formulations de pesticides
JP3776210B2 (ja) * 1997-07-15 2006-05-17 花王株式会社 農薬用効力増強剤及び農薬製剤
US6235300B1 (en) * 1999-01-19 2001-05-22 Amway Corporation Plant protecting adjuvant containing topped or peaked alcohol alkoxylates and conventional alcohol alkoxylates
UA72760C2 (en) * 1999-04-23 2005-04-15 Monsanto Technology Llc Method to treat plant foliage
GB0207438D0 (en) * 2002-03-28 2002-05-08 Syngenta Ltd Formulation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999051099A1 (fr) * 1998-04-03 1999-10-14 Monsanto Company Combinaison de glyphosate et d'un herbicide triazolinone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2006035983A1 *

Also Published As

Publication number Publication date
CN101014243A (zh) 2007-08-08
CN102302000A (zh) 2012-01-04
MY148811A (en) 2013-05-31
CN102302000B (zh) 2015-01-07
AU2005288013B2 (en) 2010-06-17
AU2005288013A1 (en) 2006-04-06
MY157730A (en) 2016-07-15
CN101014243B (zh) 2011-09-14
WO2006035983A1 (fr) 2006-04-06

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