USH750H - Herbicidal suspension concentrate - Google Patents

Herbicidal suspension concentrate Download PDF

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Publication number
USH750H
USH750H US07/260,649 US26064988A USH750H US H750 H USH750 H US H750H US 26064988 A US26064988 A US 26064988A US H750 H USH750 H US H750H
Authority
US
United States
Prior art keywords
oil
weight
parts
suspension concentrate
corn
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.)
Abandoned
Application number
US07/260,649
Other languages
English (en)
Inventor
Yasuo Ogawa
Fumio Kimura
Akira Kimura
Takeshi Hiratsuka
Nobuyuki Sakashita
Chimoto Honda
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.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Assigned to ISHIHARA SANGYO KAISHA LTD. reassignment ISHIHARA SANGYO KAISHA LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HIRATSUKA, TAKESHI, KIMURA, AKIRA, KIMURA, FUMIO, OGAWA, YASUO, SAKASHITA, NOBUYUKI, HONDA, CHIMOTO
Application granted granted Critical
Publication of USH750H publication Critical patent/USH750H/en
Abandoned legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a herbicidal suspension concentrate comprising a specific sulfonamide compound(s) and/or a salt(s) thereof, a vegetable oil, and a surfactant at a specified ratio.
  • This is a useful concentrate which can control a wide variety of harmful weeds without any phytotoxicity against corns when applied to corn fields.
  • European Patent Laid-Open Nos. 232,067 and 237,292 both disclose that sulfonamide compounds and their salts, which are the active ingredients contained in the herbicidal suspension concentrate of the present invention, are useful as herbicides for application to corn fields. However, they fail to disclose that these compounds can be admixed with a vegetable oil and a surfactant, thereby to prepare a suspension concentrate.
  • the present invention relates to a herbicidal suspension concentrate characterized by comprising from 0.5 to 20 parts by weight of at least one compound selected from among sulfonamide compounds represented by the general formula (I): ##STR2## (wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
  • sulfonamide compounds represented by the general formula (I): ##STR2## (wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
  • the suspension concentrate of the present invention when applied to a corn field, provides improved weeding effect against harmful weeds in general, and against gramineous weeds in particular, without any phytotoxicity against corns. As a result of this improvement, the spectra of the harmful weeds to be controlled are spread, and further the amount of the active ingredient compound to be used can be decreased.
  • the sulfonamide compounds of the present invention represented by the general formula (I), and their salts are already known as herbicides for application to corn fields. In practical use of these compounds, however, it is still required to decrease the amount of the active ingredient compound to be used in view of the reduction of expenditure for weeding and the reduction of environmental contamination. While it is also required to control as perfectly as possible a variety of weeds differing in growth stage without any crop injury to corns.
  • the authors of the present invention have found that use of a vegetable oil in the preparation of a suspension concentrate wherein the sulfonamide compound, represented by the general formula (I), or its salt is blended with the vegetable oil and a specific surfactant at a specific weight ratio can satisfy the requirements mentioned above when an aqueous diluted suspension prepared from the suspension concentrate is applied to a corn field. Namely they have found that use of the vegetable oil improves the weeding effect against broad spectra of the harmful weeds to be controlled without any phytotoxicity against corns and can decrease the amount of the active ingredient compound to be used, and that consequently reduction of environmental pollution can be expected.
  • Examples of sulfonamide compounds which are represented by the general formula (I), and which therefore can be used in the present invention include N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-chloro-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-bromo-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide, and N-[(4,6-dimethoxypyrimidin-2-yl)amino
  • salts of the above-mentioned sulfonamide compound include those of alkali metals such as sodium and potassium, those of alkali earth metals such as magnesium and calcium, and those of amines such as monomethylamine, dimethylamine and triethylamine, specific examples of which include sodium and monomethylamine salts of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, and dimethylamine salt of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide.
  • N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide and its salts are exemplified as preferred compounds.
  • corn oil is particularly preferred.
  • any surfactant may be used as long as it can emulsify the above-mentioned vegetable oils in water.
  • surfactants include those of vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil ether; nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene)fatty acid esters, sorbitan monooleate, and polyoxyethylene sorbitan monolaurate; and anionic surfactants such as sodium alkylarylsulfonates, sodium dialkylsuccinate sodium dialkylsulfosuccinates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl phosphates, polyoxyethylene alkylaryl phosphates, and sodium alkylnaphthalenesulfonates.
  • vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil ether
  • nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene)fatty acid esters, sorbitan monooleate, and polyoxy
  • a mixture of a surfactant of vegetable oil derivatives, a nonionic surfactant and an anionic surfactant is preferably used.
  • the suspension concentrate of the present invention is prepared, for example, according to the following procedure.
  • At least one compound selected from among the sulfonamide compounds represented by the aforementioned general formula (I) and their salts as an active ingredient compound(s) is uniformly mixed with a vegetable oil and a surfactant and the resulting mixture is ground in order to obtain a suspension concentrate.
  • an active ingredient compound(s) preliminarily ground is merely mixed with a vegetable oil and a surfactant to obtain a suspension concentrate.
  • a thixotropic material(s) such as a bentonite-alkylamine complex(es) and/or aerosil may be added in an amount of, for example, 1 to 3 weight % based on the total concentrate if necessary.
  • the suitable blending weight ratio of the above-mentioned active ingredient compound(s), the vegetable oil and the surfactant, which are the main components composing the suspension concentrate of the present invention is in the ranges of from 0.5 to 20:from 55 to 94.5:from 5 to 25 respectively, and preferably from 2 to 6:from 77 to 90:from 8 to 17 respectively.
  • the suitable amount of the suspension concentrate of the present invention to be used cannot be generically specified because it varies depending on various conditions. In general, however, it is in the range of from 0.05 to 50 g/a, preferably from 0.1 to 25 g/a, and more preferably from 0.1 to 2.5 g/a, in terms of the amount of the active ingredient compound.
  • a suspension concentrate according to the present invention was prepared in substantially the same manner as in the above-mentioned Formulation Example 1 except that 82 parts by weight of corn oil was used instead of 84 parts by weight and 12 parts by weight of Sorpol 3815 (trade name of a mixture of a polyoxyethylene alkylaryl ether, polyoxyethylene hydrogenated castor oil ether, a fatty acid derivative, and a sodium dialkylsulfosuccinate manufactured by Toho Chemical Co., Ltd.) was used instead of 10 parts by weight of Sorpol 3747.
  • Sorpol 3815 trade name of a mixture of a polyoxyethylene alkylaryl ether, polyoxyethylene hydrogenated castor oil ether, a fatty acid derivative, and a sodium dialkylsulfosuccinate manufactured by Toho Chemical Co., Ltd.
  • a suspension concentrate according to the present invention was prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
  • a suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
  • a suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
  • 1/3,000 are (a) pots and 1/10,000 are (a) pots were filled with upland soil.
  • Corn (Zea mays) (variety: Royal Dent 105 T) was sown in the 1/3,000 are (a) pots, while large crabgrass (Digitaria adscendens) and smartweed (Polygonum hydropiper) were separately sown in the 1/10,000 are (a) pots.
  • Corns (Zea mays) (varieties: Royal Dent 105T and Golden cross vantum) were sown in 6 test plots, each 2 m 2 , and weeds were allowed to naturally grow therein.
  • the growth stages of the plants 36 days after the sowing of corns were 4 to 6-leaf stages (a 5.2-leaf stage on the average) for Royal Dent 105T, 3 to 5.6-leaf stages (a 4.2-leaf stage on the average) for Golden cross vantum, 1 to 7-leaf stages (a 4.5-leaf stage on the average) for green foxtail (Setaria viridis), 1 to 6-leaf stages (a 4-leaf stage on the average) for large crabgrass (Digitaria adscendens), 2 to 6.5-leaf stages (a 4-leaf stage on the average) for smartweed (Polyonum hydropiper), cotyledon to 4-leaf stages (a 2-leaf stage on the average) for pigweed
  • the average ratings for the degree of growth control evaluated for the two test runs were found to be 1 for both of the two varieties of corns as crops and 10 for all of green foxtail, large crabgrass, smartweed, pigweed, and cocklebur.
  • 1/3,000 are (a) pots were filled with upland soil.
  • Corn (Zea mays) variety: Royal Dent 105 T) and large crabgrass (Digitaria adscendens) were sown in the separate pots respectively, and grown under upland condition in a greenhouse.
  • 5 liters/a each of aqueous diluted suspensions, prepared by suspending in water the suspension concentrate prepared in the aforementioned Formulation Example 3 were each separately foliarly applied to the plants with a small spray gun.

Landscapes

  • 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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US07/260,649 1987-10-22 1988-10-21 Herbicidal suspension concentrate Abandoned USH750H (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP62267548A JP2569342B2 (ja) 1987-10-22 1987-10-22 除草懸濁状組成物
JP62-267548 1987-10-22

Publications (1)

Publication Number Publication Date
USH750H true USH750H (en) 1990-03-06

Family

ID=17446344

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/260,649 Abandoned USH750H (en) 1987-10-22 1988-10-21 Herbicidal suspension concentrate

Country Status (14)

Country Link
US (1) USH750H (enrdf_load_stackoverflow)
EP (1) EP0313317B1 (enrdf_load_stackoverflow)
JP (1) JP2569342B2 (enrdf_load_stackoverflow)
KR (1) KR930006675B1 (enrdf_load_stackoverflow)
CN (1) CN1025812C (enrdf_load_stackoverflow)
AR (1) AR246023A1 (enrdf_load_stackoverflow)
AU (1) AU2396888A (enrdf_load_stackoverflow)
BR (1) BR8805441A (enrdf_load_stackoverflow)
DE (1) DE3870396D1 (enrdf_load_stackoverflow)
ES (1) ES2031605T3 (enrdf_load_stackoverflow)
GR (1) GR3005151T3 (enrdf_load_stackoverflow)
HU (1) HU203829B (enrdf_load_stackoverflow)
PL (1) PL275421A1 (enrdf_load_stackoverflow)
ZA (1) ZA887894B (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110021350A1 (en) * 2007-03-08 2011-01-27 E.I. Du Pont De Nemours And Company Liquid sulfonylurea herbicide formulations
US12127556B2 (en) 2016-07-06 2024-10-29 Crop Enhancement, Inc. Nontoxic coating concentrates for agricultural uses
US12329053B2 (en) 2016-07-06 2025-06-17 Crop Enhancement, Inc. Nontoxic coating concentrates for agricultural uses

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456198A1 (en) * 1990-05-10 1991-11-13 Hodogaya Chemical Co., Ltd. Oil suspension concentrate for direct paddy water application
EP0462639A1 (en) * 1990-06-05 1991-12-27 Shell Internationale Researchmaatschappij B.V. Preparation of 2-chloropyridine derivatives
DE69300089T2 (de) * 1992-01-28 1995-07-20 Ishihara Sangyo Kaisha Ltd., Osaka Chemisch stabilisierte herbizide Suspension auf Öl-Basis.
ATE171841T1 (de) * 1992-11-18 1998-10-15 Ishihara Sangyo Kaisha Verfahren zur steigerung der heroiziden wirksamkeit und herbizeiden zusammensetzungen mit gesteigerter wirksamkeit
AU653299B2 (en) * 1993-02-06 1994-09-22 Nihon Nohyaku Co., Ltd. A herbicidal composition having a reduced phytotoxicity
RU2203548C2 (ru) 1997-02-05 2003-05-10 Басф Акциенгезельшафт Твердые гербицидные смеси, способ их получения и способ борьбы с нежелательной растительностью с использованием этих смесей
US6242382B1 (en) 1997-03-24 2001-06-05 Basf Aktiengesellschaft Solid mixtures based on sulfonylureas and adjuvants
DK1130962T3 (da) * 1998-09-25 2004-05-17 Basf Ag Ikke-vandigt suspensionskoncentrat
US6165940A (en) * 1998-09-25 2000-12-26 American Cyanamid Co. Non-aqueous suspension concentrate
WO2001030155A2 (de) * 1999-10-26 2001-05-03 Aventis Cropscience Gmbh Herbizide mittel
DE19951427A1 (de) * 1999-10-26 2001-05-17 Aventis Cropscience Gmbh Nichtwässrige oder wasserarme Suspensionskonzentrate von Wirkstoffmischungen für den Pflanzenschutz
WO2001055562A1 (fr) * 2000-01-25 2001-08-02 Mitsubishi Denki Kabushiki Kaisha Dispositif de reglage du calage de distribution
TWI243019B (en) 2000-08-31 2005-11-11 Basf Ag Process for the preparation of a solid herbicidal formulation
WO2002021921A1 (de) 2000-09-13 2002-03-21 Basf Aktiengesellschaft Öl-suspensionskonzentrate auf basis eines cyclohexenonoximether-lithiumsalzes und deren verwendung als pflanzenschutzmittel
DE10129855A1 (de) * 2001-06-21 2003-01-02 Bayer Ag Suspensionskonzentrate auf Ölbasis
BR0317271A (pt) * 2002-12-13 2005-11-08 Bayer Cropscience Gmbh Concentrado de suspensão em óleo
JP4629379B2 (ja) * 2003-07-25 2011-02-09 石原産業株式会社 除草効力が向上した除草組成物及び除草効力の向上方法
EP1651042B1 (en) 2003-07-25 2016-04-27 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition having the herbicidal effect enhanced, and method for enhancing the herbicidal effect
DE10334300A1 (de) * 2003-07-28 2005-03-03 Bayer Cropscience Gmbh Ölsuspensionskonzentrat
DE10334301A1 (de) 2003-07-28 2005-03-03 Bayer Cropscience Gmbh Flüssige Formulierung
DE102004011007A1 (de) 2004-03-06 2005-09-22 Bayer Cropscience Ag Suspensionskonzentrate auf Ölbasis
RS51063B (sr) * 2005-06-04 2010-10-31 Bayer Cropscience Ag. Koncentrat uljne suspenzije
CN100418418C (zh) * 2005-06-24 2008-09-17 福建省泉州德盛农药有限公司 一种农药助剂
ZA200802442B (en) 2005-09-01 2010-02-24 Du Pont Liquid sulfonylurea herbicide formulations
JP5122841B2 (ja) * 2006-03-24 2013-01-16 石原産業株式会社 除草組成物
MX341741B (es) 2010-04-26 2016-08-31 Dow Agrosciences Llc * Dispersiones agricolas en aceite estabilizadas.
FR2967361A1 (fr) * 2010-11-16 2012-05-18 Rhodia Operations Dispersions huileuses de composes solides contenant des esters de phosphate
GB2496643B (en) * 2011-11-17 2016-08-17 Rotam Agrochem Int Co Ltd Herbicidal suspension concentrate
SI2854543T1 (sl) 2012-05-25 2016-12-30 Bayer Cropscience Ag Kemijska stabilizacija jodosulfuron-metil-natrijeve soli z uporabo hidroksistearatov
CN108124858B (zh) * 2018-01-18 2021-05-07 乔欣 一种椰子油助剂及其制备方法和应用
MX2022008464A (es) * 2020-01-14 2022-10-18 Crop Enhancement Inc Concentrados de recubrimiento no toxicos para usos agricolas.

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB803772A (en) 1954-08-03 1958-10-29 Edwin Denis Clifford Baptist Improvements in systemic herbicide compositions
US3997322A (en) 1970-09-09 1976-12-14 Sun Oil Company Of Pennsylvania Herbicide carrier oil composition
DE2701129A1 (de) 1977-01-13 1978-07-20 Knut Heyn Pflanzenvertraegliches oel zur verwendung von herbiziden
US4529438A (en) 1982-03-23 1985-07-16 Zoecon Corp. Pyridyloxy-phenoxy-alkanoic acid esters and derivatives
EP0232067A3 (en) 1986-01-30 1988-03-30 Ishihara Sangyo Kaisha Ltd. Substituted pyridinesulfonamide compounds, herbicidal composition containing them, and method of preparing these compounds
EP0237292A3 (en) 1986-03-07 1988-05-18 E.I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59134702A (ja) * 1983-01-21 1984-08-02 Ishihara Sangyo Kaisha Ltd 乳化性除草組成物
JPH01110604A (ja) * 1987-10-21 1989-04-27 Ishihara Sangyo Kaisha Ltd 有害雑草の防除方法
JPH06130585A (ja) * 1992-10-20 1994-05-13 Fuji Photo Film Co Ltd 写真用黒白現像組成物及びハロゲン化銀写真感光材料の処理方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB803772A (en) 1954-08-03 1958-10-29 Edwin Denis Clifford Baptist Improvements in systemic herbicide compositions
US3997322A (en) 1970-09-09 1976-12-14 Sun Oil Company Of Pennsylvania Herbicide carrier oil composition
DE2701129A1 (de) 1977-01-13 1978-07-20 Knut Heyn Pflanzenvertraegliches oel zur verwendung von herbiziden
US4529438A (en) 1982-03-23 1985-07-16 Zoecon Corp. Pyridyloxy-phenoxy-alkanoic acid esters and derivatives
EP0232067A3 (en) 1986-01-30 1988-03-30 Ishihara Sangyo Kaisha Ltd. Substituted pyridinesulfonamide compounds, herbicidal composition containing them, and method of preparing these compounds
EP0237292A3 (en) 1986-03-07 1988-05-18 E.I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical & Engineering News, 7-21-69, p. 41.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110021350A1 (en) * 2007-03-08 2011-01-27 E.I. Du Pont De Nemours And Company Liquid sulfonylurea herbicide formulations
US12127556B2 (en) 2016-07-06 2024-10-29 Crop Enhancement, Inc. Nontoxic coating concentrates for agricultural uses
US12329053B2 (en) 2016-07-06 2025-06-17 Crop Enhancement, Inc. Nontoxic coating concentrates for agricultural uses

Also Published As

Publication number Publication date
JP2569342B2 (ja) 1997-01-08
KR890006619A (ko) 1989-06-14
HUT49446A (en) 1989-10-30
PL275421A1 (en) 1989-07-10
JPH01110605A (ja) 1989-04-27
HU203829B (en) 1991-10-28
ZA887894B (en) 1989-07-26
BR8805441A (pt) 1989-06-27
CN1032729A (zh) 1989-05-10
CN1025812C (zh) 1994-09-07
EP0313317A3 (en) 1990-01-17
AR246023A1 (es) 1994-03-30
EP0313317A2 (en) 1989-04-26
KR930006675B1 (ko) 1993-07-22
ES2031605T3 (es) 1992-12-16
EP0313317B1 (en) 1992-04-22
AU2396888A (en) 1989-04-27
DE3870396D1 (de) 1992-05-27
GR3005151T3 (enrdf_load_stackoverflow) 1993-05-24

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