EP0786938A1 - Herbicides selectifs a base de carbamoyltriazolinones et d'heteroaryloxyacetamides - Google Patents

Herbicides selectifs a base de carbamoyltriazolinones et d'heteroaryloxyacetamides

Info

Publication number
EP0786938A1
EP0786938A1 EP95935895A EP95935895A EP0786938A1 EP 0786938 A1 EP0786938 A1 EP 0786938A1 EP 95935895 A EP95935895 A EP 95935895A EP 95935895 A EP95935895 A EP 95935895A EP 0786938 A1 EP0786938 A1 EP 0786938A1
Authority
EP
European Patent Office
Prior art keywords
cyano
alkyl
substituted
optionally substituted
optionally
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.)
Ceased
Application number
EP95935895A
Other languages
German (de)
English (en)
Inventor
Hans-Joachim Santel
Heinz Förster
Klaus-Helmut Müller
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP0786938A1 publication Critical patent/EP0786938A1/fr
Ceased 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to new herbicidal, synergistic active substance combinations which consist of known carbamoyltriazolinones on the one hand and known heteroaryloxyacetamides on the other hand and which can be used with particularly good success for selective weed control in various crops of useful plants.
  • Carbamoyltriazolinones as broadly active herbicides are the subject of a number of patent applications (cf. EP-A 294666, EP-A 370293, EP-A 391187, EP-A 398096, EP-A 399294, EP-A 415196, EP-A 477646).
  • the known carbamoyl triazolinones however, have a number of activity gaps, in particular in relation to monocotyledon weeds.
  • Heteroaryloxyacetamides as strong herbicides which are particularly effective against monocotyledon weeds, are also the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737).
  • EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737 are also the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737).
  • the invention relates to synergistic herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of (1) a carbamoyltriazolinone of the general formula (I)
  • R1 is hydrogen, hydroxy, amino or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R ⁇ represents optionally substituted alkyl, alkenyl, alkynyl, alkoxy,
  • R ⁇ represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl,
  • R 4 represents optionally substituted alkyl, alkenyl, alkynyl or alkoxy
  • R5 stands for optionally substituted alkyl, alkenyl, alkynyl or phenyl
  • R6 represents optionally substituted heteroaryl
  • herbicidal compositions according to the invention which are characterized by a content of an active compound combination consisting of (1) a carbamoyltriazolinone of the formula (I) in which
  • R 1 for hydrogen, hydroxyl, amino, for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino or dialkylamino each with up to 6 carbon atoms each optionally substituted by halogen or cyano, for cycloalkyl, cycloalkylalkyl, each optionally substituted by halogen, cyano or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl group, or for halogen, cyano, C1- C4-alkyl or -CC-alkoxy substituted phenyl or phenyl -CC-C4-alkyl,
  • R 2 for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino or optionally substituted by halogen, cyano, Cj-C4-alkoxy or C1-C4-alkylthio Dialkylamino each having up to 6 carbon atoms, for cycloalkyl, cycloalkyloxy or cycloalkylalkyl, each optionally substituted by halogen, cyano or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl group, or for each optionally substituted by halogen, cyano, C1-C4-alkyl or C1-C4-alkoxy-substitute
  • R ⁇ for each optionally by halogen, cyano, C1-C4-alkoxy, C ] -C4-alkylthio, C] -C4-alkylsulfinyl, C j -C4-alkylsulfonyl, C 1 -C4-alkylamino or di- (C] -C4-alkyl) -amino substituted alkyl, alkenyl, alkynyl each having up to 10 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by halogen, cyano or C 4 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by halogen, cyano, C1-C4-alkoxy, C ] -C4-alkylthio, C] -C4
  • R 4 represents alkyl, alkenyl, alkynyl or alkoxy each having up to 6 carbon atoms, each optionally substituted by halogen, cyano or C 4 -C alkoxy,
  • R5 for alkyl, alkenyl or alkynyl, each optionally substituted by halogen, cyano or C1-C4-alkoxy, each having up to 6 carbon atoms or for optionally halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C. 1 -C4 alkoxy or C ⁇ -C4 haloalkoxy substituted phenyl, and
  • herbicidal compositions according to the invention which are characterized by a content of an active ingredient combination consisting of (1) a carbamoyltriazolinone of the formula (I) in which
  • R 1 for hydrogen, hydroxyl, amino, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or cyano , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy or butynyloxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, propenylamino, butenylamino, propinylamino or butinylamino, ethylidene amino, propylidenamino, butylidenamino,
  • R 2 for each methyl, ethyl, n- or i-propyl, n-, i-, substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , s- or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio,
  • R ⁇ for each optionally by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, Dipropylamino or dibutylamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t
  • R 4 for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
  • R 5 for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy Pentyl, propenyl, butenyl, propynyl or butynyl, or for optionally by fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy,
  • R 6 for each optionally by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxy, Ethoxy, n- or i-propoxy, n-, i-, s- or t-
  • the herbicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the effects of the individual active compounds.
  • the new active ingredient combinations are well tolerated in many crops, the new active ingredient combinations also combating weeds such as portulaca and xanthium species which are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the selective herbicides.
  • the active substance combinations according to the invention can e.g. can be used in the following plants:
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active compound of the formula (I) accounts for 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of the active compound of the formula (II).
  • the active ingredients or combinations of active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations polymeric fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenz
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc,
  • Chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Ligin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the one in the drug combinations Active ingredients contained can also be mixed in individual formulations during use, ie applied in the form of tank mixes.
  • the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • mineral or vegetable oils which are compatible with plants (e.g. the commercial preparation "Oleo DuPont 11E") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the application rates of the active compound combinations according to the invention can be varied within a certain range; they hang among other things depending on the weather and soil factors.
  • the application rates are between 5 g and 5 kg per ha, preferably between 20 g and 2 kg per ha, particularly preferably between 50 g and 1.0 kg per ha.
  • the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process.
  • Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
  • the expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, SR: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • a water-dispersible powder formulation (WP) of a carbamoyltriazolinone of the formula (I) and a water-dispersible powder formulation (WP) of a heteroaryloxyacetamide of the formula (II) are weighed out and mixed with water to the desired concentration diluted.
  • Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant; the only decisive factor is the application rate of the active ingredient per unit area.
  • the test plants are kept in the greenhouse under controlled conditions (temperature, air humidity, light) until evaluation. After three weeks, the degree of damage to the plants is rated in% damage in comparison with the development of untreated control plants.

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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

De nouvelles combinaisons de principes actifs herbicides contiennent: 1) une carbamoyltriazolinone répondant à la formule (I) et 2) un hétéroaryloxyacétamide répondant à la formule (II), dans lesquelles R6 désigne hétéroaryle, le cas échéant substitué, et les radicaux R1 à R5 ont la signification donnée dans la description. Dans des rapports en poids déterminés, ces combinaisons ont un effet synergique et peuvent être utilisées comme herbicides sélectifs dans différentes cultures de plantes utiles (par exemple maïs et soja). Elles permettent de combattre avec succès même des mauvaises herbes difficiles à combattre telles que des plantes des genres Portucala et Xanthium.
EP95935895A 1994-10-17 1995-10-04 Herbicides selectifs a base de carbamoyltriazolinones et d'heteroaryloxyacetamides Ceased EP0786938A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4437049A DE4437049A1 (de) 1994-10-17 1994-10-17 Selektive Herbizide auf Basis von Carbamoyltriazolinonen und Heteroaryloxyacetamiden
DE4437049 1994-10-17
PCT/EP1995/003906 WO1996011575A1 (fr) 1994-10-17 1995-10-04 Herbicides selectifs a base de carbamoyltriazolinones et d'heteroaryloxyacetamides

Publications (1)

Publication Number Publication Date
EP0786938A1 true EP0786938A1 (fr) 1997-08-06

Family

ID=6530970

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95935895A Ceased EP0786938A1 (fr) 1994-10-17 1995-10-04 Herbicides selectifs a base de carbamoyltriazolinones et d'heteroaryloxyacetamides

Country Status (9)

Country Link
US (1) US5811373A (fr)
EP (1) EP0786938A1 (fr)
CN (1) CN1076585C (fr)
AU (1) AU3803595A (fr)
BR (1) BR9509362A (fr)
DE (1) DE4437049A1 (fr)
HU (1) HU223670B1 (fr)
MX (1) MX9702552A (fr)
WO (1) WO1996011575A1 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2128984B1 (es) * 1996-05-24 2000-02-01 Bayer Ag Herbicidas a base de heteroariloxi-acetamidas para el empleo en el cultivo de arroz.
AU771265B2 (en) 1999-09-30 2004-03-18 Bayer Aktiengesellschaft Selective herbicides on the basis of N-aryl-triazoline(thi)ones
DE10041619A1 (de) 2000-05-22 2001-11-29 Bayer Ag Selektive Herbizide auf Basis von Heteroaryloxyacetamiden
PL218432B1 (pl) * 2000-05-22 2014-12-31 Bayer Cropscience Ag Selektywny środek chwastobójczy, zastosowanie środka, sposób zwalczania niepożądanych roślin, sposób wytwarzania środka chwastobójczego
MX339832B (es) * 2009-06-09 2016-06-14 Arysta Lifescience Corp Combinaciones herbicidas basadas en carbamoil triazolinone y procesos de uso.
US10299479B2 (en) 2009-06-09 2019-05-28 Arysta Lifescience Corporation Carbamoyl triazolinone based herbicide combinations and methods of use
HUE029099T2 (en) * 2009-12-17 2017-02-28 Bayer Ip Gmbh Herbicidal preparations containing Flufenacet
WO2011082968A2 (fr) 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2011082964A1 (fr) 2009-12-17 2011-07-14 Bayer Cropscience Ag Produits herbicides contenant du flufénacet
EP2512248B1 (fr) * 2009-12-17 2016-08-10 Bayer Intellectual Property GmbH Agents herbicides contenant du flufénacet
WO2011082956A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2011082957A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2011082959A2 (fr) 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2011082955A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
LT2515658T (lt) * 2009-12-17 2016-09-26 Bayer Intellectual Property Gmbh Herbicidiniai agentai, turintys flufenaceto
WO2011082954A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2011082953A2 (fr) * 2009-12-17 2011-07-14 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2014001361A1 (fr) 2012-06-27 2014-01-03 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
AU2013283381B2 (en) 2012-06-27 2017-02-02 Bayer Cropscience Ag Herbicidal agents containing flufenacet
WO2014001357A1 (fr) 2012-06-27 2014-01-03 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
WO2014001248A1 (fr) 2012-06-27 2014-01-03 Bayer Cropscience Ag Agents herbicides contenant du flufénacet
EP2936983A1 (fr) 2014-04-25 2015-10-28 Bayer CropScience AG Agents actifs destinés à l'augmentation du rendement des cultures de coton
CN105660661B (zh) * 2016-03-18 2018-08-17 哈尔滨利民农化技术有限公司 一种玉米田除草组合物及其使用方法
BR102018075132A2 (pt) 2018-12-04 2020-06-16 UPL Corporation Limited Composição herbicida sinergística de amplo espectro para o controle de plantas daninhas em culturas agrícolas, uso da dita composição para preparação de produto, produto e método de aplicação

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3803523A1 (de) * 1987-06-12 1988-12-22 Bayer Ag Substituierte triazolinone
DE3821600A1 (de) * 1988-06-27 1989-12-28 Bayer Ag Heteroaryloxyessigsaeure-n-isopropylanilide
DE4005930A1 (de) * 1990-02-25 1991-08-29 Bayer Ag Selektiv-herbizide mittel, enthaltend ethofumesate, phenmedipham, chloridazon oder quinmerac in kombination mit bestimmten triazolinonen
DE4223465A1 (de) * 1992-07-16 1994-01-20 Bayer Ag Herbizide Mittel auf Basis von Heteroaryloxyacetamiden

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9611575A1 *

Also Published As

Publication number Publication date
AU3803595A (en) 1996-05-06
HU223670B1 (hu) 2004-11-29
US5811373A (en) 1998-09-22
MX9702552A (es) 1997-06-28
WO1996011575A1 (fr) 1996-04-25
CN1076585C (zh) 2001-12-26
HUT77299A (hu) 1998-03-30
DE4437049A1 (de) 1996-04-18
CN1160988A (zh) 1997-10-01
BR9509362A (pt) 1997-11-04

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