CN1179885A - Herbicidal compositions based on N-isopropyl -N -(4 -fluorophenyl) (5 -trifluoromethyl -1, 3, 4 -thiadiazol -2 -yloxy) acetamide - Google Patents

Herbicidal compositions based on N-isopropyl -N -(4 -fluorophenyl) (5 -trifluoromethyl -1, 3, 4 -thiadiazol -2 -yloxy) acetamide Download PDF

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CN1179885A
CN1179885A CN 97117976 CN97117976A CN1179885A CN 1179885 A CN1179885 A CN 1179885A CN 97117976 CN97117976 CN 97117976 CN 97117976 A CN97117976 A CN 97117976A CN 1179885 A CN1179885 A CN 1179885A
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reactive compound
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weight
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isopropyl
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CN1081440C (en
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P·达门
D·福伊希特
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Bayer Pharma AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/13—Oxygen atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

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

Abstract

The present invention relates to novel synergistic herbicidal combinations of N-isopropyl-N-(4-fluorophenyl)(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetam ide with fenoxaprop-ethyl and/or clodinafop-propargyl.

Description

With N-isopropyl-N-(4-fluorophenyl) (5-Trifluoromethyl-1,3,4-thiadiazoles-2-base oxygen base) acetamide is the Herbicidal combinations on basis
The present invention relates to the Herbicidal synergistic combination of the novelty of known heteroaryloxyacetamides and other known weed killer herbicide.Described other known weed killer herbicide belongs to and can particularly advantageously be used for selectivity and prevent and treat other type weed killer herbicides of the weeds in the various crops.
List in following patent described monocotyledon weed (two grassy weeds) is had especially active, and also to the effective heteroaryloxyacetamides of some broadleaf weed.In fact they do not have the soil effect and almost do not have the blade face activity, in them some have very strong selectivity [referring to, EP-A5 501 (=US 4 509 971 and US 4 833 243) for example in unifacial leaf and dicotyledonous crops such as cereal class, corn, rice, soybean and cotton; EP-A18497 (=US4 645 525 and US4 756 741); EP-A29171 (=US4 408 055); EP-A94514 (=US 585 471); EP-A100044 (=US4 549 899); EP-A100045 (=US 4 540 430); EP-A 161602 (=US 4 784 682); EP-A 195237 (=US 4 788291); DE-A3724467; EP-A 348734 (=US4 988 380); EP-A 348737 (=US4968342 and 5090991); DE-A 4 113 421 and DEE-A 4 137 827; And WO91/06544].
In addition, DE4,223 465 have described the Synergistic blend of the weed killer herbicide of heteroaryloxyacetamides and following type: N-phenylurea, N-benzothiazolyl urea, 2, the 6-dinitroaniline, s-triazine, as-triazinone, sulfonylureas, imidazolone, pyridine carboxamides and diphenyl ether.Yet the mixture in this literary composition does not all obtain any practical significance.The shortcoming that is described in the mixture among the DE4 223 465 is, under the various weed growths situation in great numbers, their effect is always outstanding.
N-isopropyl-N-(4-fluorophenyl) (5-Trifluoromethyl-1,3, the 4-thiadiazoles-2-base oxygen base) acetamide that the purpose of this invention is to provide with formula I is the Synergistic herbicidal mixtures of the novelty on basis
Figure A9711797600031
This mixture is better than mixture of the prior art aspect active, and it has effect to the weeds of wide spectrum.
This purpose is by realizing known weed killer herbicide and the combination of formula (I) reactive compound.In biologic test, be surprised to find that, these active aspects that are combined in weeds demonstrate significant synergistic effect, and can particularly advantageously be used as effective wide spectrum combination product, be used for selective herbicidal, be applicable to by method before the seedling and behind the seedling and remove unifacial leaf and broadleaf weed.These combinations can prevent and treat the broad leaved weed and the dogstail of majority important economically (being a problem) effectively in unifacial leaf and dicotyledonous crops such as corn, wheat, barley, rice, soybean and sunflower.
Therefore the invention provides Synergistic herbicide compositions, it is characterized in that, they comprise N-isopropyl-N-(4-fluorophenyl) (5-Trifluoromethyl-1 of the formula (I) of effective dose, 3,4-triazole-2-base oxygen base) acetamide and at least a formula (II) or (III) the reactive compound combination of weeding active compound.
Formula (1) compound is known from EP-A348 737 and US4968 342.
The oxazole diclofop-methyl is 2-[4-(6-Lv benzoxazole-2-yl) oxygen phenoxyl] ethyl propionate, be described among the DE2640 730.
Clodinafop-propargyl is (R)-2[4-[(5-chloro-3-fluorine pyridine-2-yl)-the oxygen base] the phenoxy propionic acid propynyl ester, be described among the EP-A 248 968.
The heteroaryloxyacetamides that comprises formula (I) reactive compound has special activity to monocotyledon weed (two grassy weeds), and also some broadleaf weeds is had effect.
The reactive compound of being mentioned (II) and (III) can be used for optionally preventing and treating the dogstail of wide spectrum such as important economically crop such as cereal class, corn, soybean, cotton, beet and rice.Yet they are always not gratifying to some harmful monocotyledonous activity.Important be a problem weeds such as wind grass can not be prevented and treated usually fully.
Surprising is to have now found that formula (I) heteroaryloxyacetamides and reactive compound as defined above (II) and/or the combination of reactive compound (III) have extra high activity, and can select the dried rhizome of rehmannia to be used for many crops.
Surprising is that the activity of weeding of reactive compound combination of the present invention is more high than the active sum of single reactive compound.
This just means not only has complementation to exist, and has unpredictalbe true synergistic effect.Many crops have good anti-sex change to this novel biochemical compound combination of living, and or even weeds that are difficult to prevent and treat such as wind grass, also can be prevented and treated by this novel reactive compound with combining.Therefore, this novel reactive compound combination is that the useful of selective herbicide scope replenished.
Reactive compound combination of the present invention can be used for for example following plants: the dicotyledonous crops of following dependent of dead military hero: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, linum, sweet potato genus, Vetch, Nicotiana, tomato genus, Arachis, Brassicas, Lactuca, Cucumis and Cucurbita.The monocotyledon weed of following dependent of dead military hero; Echinochloa, setaria, Panicum, knotgrass, ladder forage spp, annual bluegrass genus, Festuca, the Shuai grass genus of coiling, Lolium, Brome, Avena, Cyperus, jowar genus, Agropyron, Cynodon, Monochoria, genus fimbristylis, arrowhead genus, Eleocharis, Fischer grass genus, Paspalum, ischaemum, cusp Pittosporum, talon eria, Agrostis, fragrant wheat ma genus and wind grass belong to.The monocot crops of following dependent of dead military hero: Oryza, Zea, Triticum, Hordeum, Avena, Secale, jowar genus, Panicum, saccharum, Ananas, Asparagus and allium.
Yet reactive compound combination of the present invention only limits to these genus anything but, and it can extend to other plant in an identical manner.
The synergistic effect of reactive compound combination of the present invention is remarkable especially under the specific concentrations ratio.Yet the weight ratio of the reactive compound in the reactive compound combination can change in quite wide scope.Usually, for formula (I) reactive compound of every part of weight, 0.001 to 1000 part of weight of employing, preferred 0.01 to 100 part of weight, the formula (II) of preferred especially 0.1 to 30 part of weight and/or formula (III) reactive compound.
Reactive compound or reactive compound combination can change into common formulation, as solution, emulsion, wetting powder, suspending agent, powder, pulvis, paste, soluble powder, granule, suspension emulsion, with the natural and synthetic material of reactive compound dipping and the microcapsules of polymeric material.
These type agent can be produced in known manner.For example, reactive compound is mixed with filler.Filler is a liquid flux, and/or mixes with solid carrier, and the optional surfactant that uses, and it is emulsifier and/or dispersant and/or foaming agent.
Use water as under the situation of filler, organic solvent also can be used as cosolvent.As liquid flux, suitable mainly contains: aromatic compounds, and as dimethylbenzene, toluene or molten basic naphthalene, chloro aromatic compounds or chlorinated aliphatic hydrocarbon, as the chlorobenzene class, polyvinyl chloride-base or carrene, aliphatic hydrocarbon, as cyclohexane or paraffin, for example petroleum cuts mineral oil and vegetable oil, alcohols, as butanols or ethylene glycol, and ether and ester, ketone, as acetone, MEK, methyl isopropyl Ketone or cyclohexanone, intensive polar solvent, as dimethyl formamide or dimethyl sulfoxide (DMSO), and water; Suitable solid carrier is, for example the natural minerals of ammonium salt and grinding is as kaolin, clay, and talcum, chalk, quartz, Attagel, montmorillonite or diatomite and the synthetic mineral matter that grinds, as high dispersive silica, alumina and silicate; Be used for suitable the having of solid carrier of granule: for example crushing and broken natural mineral matter such as calcite, marble, float stone, sepiolite and dolomite, and other synthetic particle and following organic particle organic and inorganic powder: wood sawdust, coconut husk, corncob and tobacco stem; What emulsifier and/or foaming agent were fit to has: for example nonionic and anion emulsifier, and as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example, alkaryl polyglycol ether, alkylsulfonate, alkyl sulfate, arylsulphonate and protein hydrolysate; What the mark agent was fit to has: for example, and lignin sulfite waste liquor and methylcellulose.
Can use the carboxymethyl cellulose and the natural and synthetic polymer of adhesive such as powdery, particle or latex form in the preparation, as gum Arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipid, as cephalin and lecithin, and synthetic phospholipid.Other adhesive can be mineral oil and vegetable oil.
Also may use dyestuff, as inorganic pigment, iron oxide for example, titanium oxide and Prussian blue, and organic dyestuff, as alizarin dyes, azo dyes and metal phthalocyanine dye bucket and micronutrient such as molysite, manganese salt, boron salt, mantoquita, cobalt salt, molybdenum salt and zinc salt.
Usually the reactive compound that contains weight ratio 0.1 to 95% in the preparation, preferred 0.5 to 90%.
Usually, active compound combinations of the present invention is used with ready-made mixture.But the reactive compound in active compound also can prepare respectively, and is mixed when using, and promptly uses with the form of bucket (tank) mixture.
New reactive compound former state or its dosage form also can as with the mixture of other known weed killer herbicide, whole preparation or also can be the mixed thing of bucket.It also can be mixture with other known activity compound such as fungicide, insecticide, miticide, nematicide Liu, bird repellent, growth promoter, plant nutrient and soil conditioner.In addition, for specific purpose, also advantageously, particularly after using seedling during method, mix the mineral or the vegetable oil (for example " Oleo Dupont 11E " that are tolerated by plant, it is that commerce can get), or mix ammonium salt such as ammonium sulfate or thiocyanic acid ammonium salt, as the additional additive in the preparation.
The present invention's novel reactive compound combination can be with its former state, and its dosage form or used by the type of service by will it dilution preparation is for example with direct use solution, suspension, emulsion, powder, cream and particle form use.They use with common mode, for example by watering, spraying, atomizing, dusting or remove and execute.
The amount of application of reactive compound combination of the present invention can change in certain scope; They depend on particularly weather and soil condition.Usually, amount of application is 0.01 to 10kg/ha, and preferred 0.03 to 5kg/ha, and particularly 0.05 to 3.0kg/ha.
Reactive compound of the present invention combination can be before plant germination and after use, promptly by before the seedling and the method behind the seedling.
The good activity of weeding of this novel reactive compound combination is proved by the following example.Though single reactive compound aspect its activity of weeding a little less than, the present composition demonstrates very effective herbicidal effect, and this control efficiency surpasses the simple summation of single reactive compound activity.
On weed killer herbicide, when the activity of weeding of reactive compound combination surpasses the activity of the reactive compound of using separately, then always exist synergistic effect.
The expection activity of the given combination of two kinds of weed killer herbicides can be calculated as follows (referring to, Colby, SR: " Calculating synergistic and antagonistic response of herbicidecombinatiosn " Weed 15, pp 20-22,1967): if X=% is under the situation of pkg/ha at amount of application, weed killer herbicide A (the 1st group of reactive compound) loss ratio, and
Y=% is under the situation of qkg/ha at amount of application, weed killer herbicide B (the 2nd group of reactive compound) loss ratio, and
E=% is under the situation of p and qkg/ha at amount of application, the speculative damage of weed killer herbicide A and B, then E = X + Y - ( X · Y 100 ) If actual damage surpasses calculated value, the activity of composition is super adduction, i.e. its demonstration synergy.
(activity of weeding of the reactive compound combination of being found of the present invention surpasses calculated value, i.e. this novel reactive compound combination has synergistic effect in the following example announcement.Application Example
When required active agent preparations is tested in preparation, weigh the water dispersible formulation agent (WP) of appropriate amount formula (1) heteroaryl acetamide and formula (II) and/or commerce (III) and can get preparation, and be diluted with water to desired concn, and close by wind, prepare the various combinations of two kinds of reactive compounds.A) test behind the greenhouse seedling
To highly spray with reactive compound for the test plant of 5-15cm, per unit area is used the reactive compound of specified quantitative.Select the concentration of spray liquid, make the required reactive compound of can 500 premium on currency/ha using specified quantitative.After the processing, test plant is placed greenhouse under the controlled condition (temperature, air themperature, light), up to estimating.After three weeks, will relatively grade, make infringement % the extent of damage of plant and the developmental phase of untreated control plant.Numeral is meant that 0%=does not have effect/infringement (contrast is identical with handling) 100%=and destroys fully
Reactive compound, amount of application and the results are shown in the following table.(I) Clodinafop-propargy that method obtains behind table 1 seedling is (with (I) and the activity of weeding of clodinafop-propargyl to the wind grass.
Preparation Amount of application ga.i./ha Activity of weeding % to the wind grass
Observation Calculated value
(I) (I) (I) ????60 ????30 ????15 ????40 ????40 ????20
??Clodinafop-propargyl ??Clodinafop-propargyl ????30 ????15 ????10 ????0
????(I)+ ??Clodinafop-propargyl ????60 ????+30 ????80 ????46
????(I)+ ??Clodinafop-propargyl ????30 ????+30 ????70 ????46
????(I)+ ??Clodinafop-propargyl ????15 ????+30 ????50 ????28
????(I)+ ??Clodinafop-propargyl ????60 ????+15 ????60 ????40
????(I)+ ??Clodinafop-propargyl ????30 ????+15 ????50 ????40
????(I)+ ??Clodinafop-propargyl ????15 ????+15 ????30 ????20
Table 2: (I) that obtains by method behind the seedling, oxazole diclofop-methyl and (I) with the activity of weeding of the mixed thing of oxazole diclofop-methyl bucket to the wind grass
Preparation Amount of application ga.i./ha Activity of weeding % to the wind grass
Observation Calculated value
????(I) ????60 ????40
Oxazole dogstail Ling oxazole diclofop-methyl ????30 ????15 ????20 ????0
(I)+the oxazole diclofop-methyl ????60 ????+30 ????60 ????52
(I)+the oxazole diclofop-methyl ????60 ????+15 ????50 ????40
Table 1 and table 2 explanation: active or infringement (in the %) calculated value=employing above-mentioned COLBY formula activity calculated or infringement (in %) the a.i=active component of observation=observe
What oxazole diclofop-methyl (II) or clodinafop-propargyl (III) used is that following commerce can get preparation: (II) be RRALON060EW (water and milk Liu) (AgrEvo) (III) is RTOPIK 240EC (missible oil) is (Novartis).

Claims (7)

1, Synergistic herbicide compositions is characterized in that, they comprise formula (I) N-isopropyl-N-(4-fluorophenyl) (5-Trifluoromethyl-1,3,4-thiadiazoles-2-base oxygen base) acetamide of effective dose
Figure A9711797600021
Reactive compound combination with at least a formula (II) or weeding active compound (III) (II) oxazole diclofop-methyl and/or (III) clodinafop-propargyl
2, according to the Synergistic herbicidal agents of claim 1, it is characterized in that, N-isopropyl-the N-of every part of weight (4-fluorophenyl) (5-trifluoroethyl-1,3,4-thiadiazoles-2-base oxygen base) acetamide (I) adopts the formula (II) of 0.001 to 1000 part of weight and/or (III) reactive compound.
3, according to the Synergistic herbicide compositions of claim 1, its spy just is, the formula of every part of weight (I) reactive compound adopts the formula (II) of 0.01 to 100 part of weight and/or (III) reactive compound.
According to the Synergistic herbicide compositions of claim 1, it is characterized in that 4, the formula of every part of weight (I) reactive compound adopts the formula (II) of 0.1 to 30 part of weight and/or (III) reactive compound.
5, method of controlling weeds is characterized in that, the reactive compound compound action that makes claim 1 to 4 is in weeds and/or its dried rhizome of rehmannia of dwelling.
6, the application of the reactive compound of claim 1 to 4 combination controlling weeds.
7, prepare the method for Herbicidal combinations, it is characterized in that, the reactive compound combination of claim 1 to 4 is mixed with filler and/or surfactant.
CN97117976A 1996-07-17 1997-07-17 Herbicidal compositions based on N-isopropyl -N -(4 -fluorophenyl) (5 -trifluoromethyl -1, 3, 4 -thiadiazol -2 -yloxy) acetamide Expired - Lifetime CN1081440C (en)

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DE19628777 1996-07-17

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101715768A (en) * 2009-12-08 2010-06-02 安徽丰乐农化有限责任公司 Clodinafop-propargyl fenoxaprop compound herbicide
CN101292658B (en) * 2002-11-21 2011-08-24 辛根塔参与股份公司 Herbicidal composition
CN102239854A (en) * 2011-05-18 2011-11-16 利尔化学股份有限公司 Weeding pesticide composition
CN101700023B (en) * 2009-10-21 2012-07-25 张志高 Clodinafop-propargyl and fenoxaprop-p-ethyl herbicide composition

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2200927T3 (en) * 1999-09-07 2004-03-16 Syngenta Participations Ag HERBICIDE COMPOSITION.
PT1210333E (en) 1999-09-07 2005-03-31 Syngenta Participations Ag P-TOLYL-HETEROCYCLES AS HERBICIDES
DE19947918A1 (en) * 1999-10-06 2001-04-12 Bayer Ag Selective herbicides based on pyrimidine derivatives
PL362894A1 (en) * 1999-11-17 2004-11-02 Bayer Aktiengesellschaft Selective herbicides based upon 2,6-disubstituted pyridine derivatives
DE10041619A1 (en) * 2000-05-22 2001-11-29 Bayer Ag Selective herbicides based on heteroaryloxyacetamides
WO2001089301A1 (en) * 2000-05-22 2001-11-29 Bayer Cropscience Ag Selective heteroaryloxy-acetamide-based herbicides
AR036580A1 (en) * 2001-09-27 2004-09-15 Syngenta Participations Ag HERBICIDE COMPOSITION

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2640730C2 (en) * 1976-09-10 1983-08-25 Hoechst Ag, 6230 Frankfurt Benzoxazolyloxy and benzothiazolyloxyphenoxy compounds and herbicidal agents containing them
CH679396A5 (en) * 1986-06-12 1992-02-14 Ciba Geigy Ag
DE4223465A1 (en) * 1992-07-16 1994-01-20 Bayer Ag Herbicidal agents based on heteroaryloxyacetamides
EP0614608B1 (en) * 1993-02-18 1999-01-07 Hoechst Schering AgrEvo GmbH Synergistic mixture for control of blackgrass
DE4317323A1 (en) * 1993-05-25 1994-12-01 Bayer Ag N- (4-fluoro-phenyl) heteroaryloxyacetamide
DE4428982C1 (en) * 1994-08-16 1996-05-15 Hoechst Schering Agrevo Gmbh Selective herbicide, esp. for foxtail millet control in crops
DE19546751B4 (en) * 1994-12-23 2005-02-17 Bayer Cropscience Ag Selective herbicides based on heteroaryloxy-acetamides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101292658B (en) * 2002-11-21 2011-08-24 辛根塔参与股份公司 Herbicidal composition
CN101700023B (en) * 2009-10-21 2012-07-25 张志高 Clodinafop-propargyl and fenoxaprop-p-ethyl herbicide composition
CN101715768A (en) * 2009-12-08 2010-06-02 安徽丰乐农化有限责任公司 Clodinafop-propargyl fenoxaprop compound herbicide
CN101715768B (en) * 2009-12-08 2013-07-17 安徽丰乐农化有限责任公司 Clodinafop-propargyl fenoxaprop compound herbicide
CN102239854A (en) * 2011-05-18 2011-11-16 利尔化学股份有限公司 Weeding pesticide composition

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GB2315413A (en) 1998-02-04
FR2751174B1 (en) 2000-04-07
GB9714993D0 (en) 1997-09-24
CN1081440C (en) 2002-03-27
GB2315413B (en) 2000-03-08
DE19728568A1 (en) 1998-01-22
CA2210273C (en) 2007-10-02
FR2751174A1 (en) 1998-01-23
CA2210273A1 (en) 1998-01-17

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