[go: up one dir, main page]

WO1993016596A1 - Procede de nettoyage d'un reservoir de pulverisation - Google Patents

Procede de nettoyage d'un reservoir de pulverisation Download PDF

Info

Publication number
WO1993016596A1
WO1993016596A1 PCT/US1993/001295 US9301295W WO9316596A1 WO 1993016596 A1 WO1993016596 A1 WO 1993016596A1 US 9301295 W US9301295 W US 9301295W WO 9316596 A1 WO9316596 A1 WO 9316596A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
methyl
group
sulfonylurea
carbonyl
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
PCT/US1993/001295
Other languages
English (en)
Inventor
Luann Marshall Pugh
William Robert Cahill, Jr.
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP93905045A priority Critical patent/EP0626807A1/fr
Priority to BR9305997A priority patent/BR9305997A/pt
Priority to JP5514907A priority patent/JPH07503973A/ja
Publication of WO1993016596A1 publication Critical patent/WO1993016596A1/fr
Anticipated expiration legal-status Critical
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<
    • A01N47/36—Ureas 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

  • Sulfonylureas as a class, are highly active pesticides. For this reason, care must be taken to make sure that all traces of sulfonylurea are cleaned out of the spray equipment (hereafter referred to as spray tank), which is used to apply pesticides to crops, before an applicator uses this equipment in a subsequent application to treat a crop that is
  • spray tank the spray equipment
  • Adequate cleanout may require a rinsing procedure that is time-consuming and causes an environmental waste-water disposal problem.
  • Salts of the sulfonylureas are generally known as are methods for making them. What has not been
  • This invention concerns a method for reducing residual sulfonylurea pesticide contamination of a spray tank from which the sulfonylurea is applied, comprising the steps:
  • the sulfonylureas whose spray tank buildup is curtailed by the method of this invention are the sulfonylurea acids either when used alone or with one or more tank mix partners .
  • the benefits achieved by this invention have been found to be more pronounced when the sulfonylurea is employed with a tank mix partner.
  • the benefits are even more noteworthy when earlier tank mixes have left organic deposits on inside spray tank surfaces. In such instances, it is believed that undissolved particles of the sulfonylurea are held by the organic deposit and kept from becoming
  • tank mixes of the sulfonylureas are primarily suspensions. Suspended particles can collect on tank walls, in tubing, or be trapped by organic deposits that may be present inside the tank. If a later tank mix sends the sulfonylurea into solution or suspension, sensitive crops can be damaged.
  • sulfonylureas in a water-soluble form.
  • the sulfonylurea salt form shows a faster dissolution rate than the corresponding sulfonylurea acid, particularly evident at low pH's.
  • Use of sulfonylureas in their salt form rather than their acid form has been found, under a variety of circumstances, to result in a greater than fourfold improvement in spray tank
  • Preferred salt cations (M) are the sodium
  • Preferred sulfonylurea salts are the sodium and calcium salts of tribenuron methyl, the potassium salt of thifensulfuron methyl, the ammonium salt of chlorsulfuron and the potassium salt of metsulfuron methyl.
  • Figures represent comparisons in bar graph format of the data summarized in the Tables.
  • Figure 1 shows a statistically significant distinction between ease of cleanout of sulfonylurea-tank partner mixtures (37% failure rate) vs. cleanout of corresponding sulfonylurea salt-tank partner mixtures (8% failure).
  • R is selected from the group H and CH 3 ;
  • R 1 is selected from the group F, Cl, Br, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 haloalkenyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy,
  • R 2 is selected from the group H, F, Cl, Br, CN,
  • R 3 is selected from the group Cl, NO 2 , CO 2 CH 3 ,
  • R 4 is selected from the group C 1 -C 3 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, NO 2 , CO 2 R 12 , C(O)NR 13 R 14 , SO 2 NR 15 R 16 ,
  • R 5 is selected from the group H, F, Cl, Br and CH 3 ;
  • R 6 is selected from the group C 1 -C 3 alkyl, C 2 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, CO 2 R 12 , C(O)NR 13 R 14 , SO 2 NR 15 R 16 , S(O) n R 17 , C(O)R 18 and L;
  • R 7 is selected from the group H, F, Cl, CH 3 and
  • R 8 is selected from the group H, C 1 -C 3 alkyl and pyridyl;
  • R 9 is selected from the group C 1 -C 3 alkyl, C 1 -C 2 alkoxy, F, Cl, Br, NO 2 , CO 2 R 12 , SO 2 NR 15 R 16 , S(O) n R 17 , OCF 2 H, C(O)R 18 , C 2 -C 4 haloalkenyl and
  • R 10 is selected from the group H, Cl, F, Br, C 1 -C 3 alkyl and C 1 -C 2 alkoxy;
  • R 11 is selected from the group H, C 1 -C 3 alkyl, C 1 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, CO 2 R 12 ,
  • R 12 is selected from the group allyl and propargyl and C 2 -C 3 alkyl optionally substituted by at least one member independently selected from halogen, C 1 -C 2 alkoxy and CN;
  • R 13 is selected from the group H, C 1 -C 3 alkyl and
  • R 14 is C 1 -C 2 alkyl
  • R 15 is selected from the group H, C 1 -C 3 alkyl, C 1 -C 2 alkoxy, allyl and cyclopropyl;
  • R 16 is selected from the group H and C 1 -C 3 alkyl
  • R 17 is selected from the group C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, allyl and propargyl;
  • R 18 is selected from the group C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 3 -C 5 cycloalkyl optionally substituted by halogen;
  • n 0, 1 or 2;
  • M is a cation
  • R j is selected from the group H and C 2 -C 3 alkyl; W is selected from the group O and S;
  • X is selected from the group H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkylthio, C 1 -C 4 alkylthio, halogen, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino and di (C 1 -C 3 alkyl) amino;
  • Y is selected from the group H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino, di (C 1 -C 3 alkyl) amino, C 3 -C 4 alkenyloxy, C 3 -C 4
  • alkynyloxy C 2 -C 5 alkylthioalkyl, C 2 -C 5 alkylsulfinylalkyl, C 2 -C 5 alkylsulfonylalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkynyl, C 3 -C 5
  • Z is selected from the group CH and N;
  • X and Y when one or both of X and Y is C 1 haloalkoxy, then Z is CH; and ii) when X is halogen, then Z is CH and Y is OCH 3 , OCH 2 CH 3 , N(OCH 3 )CH 3 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H.
  • Salts of the following sulfonylureas are preferred for use in the disclosed process: 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (chlorsulfuron); methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (sulfometuron methyl); ethyl 2-[[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (chlorimuron ethyl); methyl 2-[[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate (metsulfur
  • sulfonylurea salts of the following sulfonylureas 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylate (thifensulfuron methyl), methyl 2- [[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate (metsulfuron methyl), methyl 2-[[[[[[N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N-methylamino]carbonyl]amino]sulfonyl]benzoate
  • Sulfonylurea salts of this invention can be used alone or in combination with other commercial
  • herbicides including other sulfonylureas or
  • Mixtures containing sulfonylurea salts are particularly useful in minimizing spray tank cleanout when compared to the same mixtures containing the corresponding sulfonylurea acid.
  • Thifensulfuron methyl 190 propiconazole 0 + Metsulfuron 380 propiconazole 100 methyl (10:1) 600 propiconazole 0
  • Step 7 Rinse the interior tank surfaces with fresh water; use about 10% of the tank capacity to remove all traces of the cleaning solution. Spray the rinse through the boom. Drain the remainder from the tank. Step 7
  • Step 6 Rinse the tank with clean water, using a volume of 10-20% of the tank capacity. Allow the rinse water to accumulate in the tank and then discard through the boom and nozzles . Drain any remaining rinse water from the tank . Step 6
  • bioassay protocol employed to determine the percent injury of the crop (sugarbeets) sprayed with the final rinse solution after tank cleanout of the ingredients listed in the Tables is as follows.
  • Sugarbeet seedlings (at the two-leaf stage) were grown in the greenhouse (14 hour photoperiod at 21°C with light and 10 hours at 17°C in the dark) and sprayed with unmodified samples of effluent from various sprayer cleanout procedures.
  • An automatic belt sprayer was used, and the samples were applied at a rate of approximately 45 gal/A.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Use formulations include dusts, granules, pellets, solutions, Table B, suspensions, emulsions, gels, actives in plastic, wettable powders,
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of salts of sulfonylurea(s), diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
  • Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S.
  • Granules and pellets can be made by
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.
  • Compound 1 is the ammonium salt of chlorsulfuron.
  • Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Compound 1 65.0% sodium alkyl naphthalenesulfonate 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.

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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On facilite le nettoyage des résidus de pesticides à base de sulfonyl urée présents dans des réservoirs de pulvérisation 1) en formulant la sulfonyl urée de façon qu'elle constitue un sel hydrosoluble approprié à l'agriculture, avant qu'on ne la verse dans ledit réservoir, 2) en utilisant cette composition à base de sel sur les cultures et 3) en rinçant ce réservoir pour éliminer en pratique tout résidu de sulfonyl urée plus facilement que lorsque ce produit n'est pas sous la forme d'un sel.
PCT/US1993/001295 1992-02-19 1993-02-12 Procede de nettoyage d'un reservoir de pulverisation Ceased WO1993016596A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP93905045A EP0626807A1 (fr) 1992-02-19 1993-02-12 Procede de nettoyage d'un reservoir de pulverisation
BR9305997A BR9305997A (pt) 1992-02-19 1993-02-12 Método para limpeza de tanque spray
JP5514907A JPH07503973A (ja) 1992-02-19 1993-02-12 スプレータンク清掃方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83859092A 1992-02-19 1992-02-19
US07/838,590 1992-02-19

Publications (1)

Publication Number Publication Date
WO1993016596A1 true WO1993016596A1 (fr) 1993-09-02

Family

ID=25277514

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/001295 Ceased WO1993016596A1 (fr) 1992-02-19 1993-02-12 Procede de nettoyage d'un reservoir de pulverisation

Country Status (11)

Country Link
EP (1) EP0626807A1 (fr)
JP (1) JPH07503973A (fr)
CN (1) CN1077838A (fr)
AU (1) AU3618793A (fr)
BR (1) BR9305997A (fr)
CA (1) CA2130118A1 (fr)
HU (1) HUT71707A (fr)
LT (1) LT3009B (fr)
RU (1) RU94040706A (fr)
WO (1) WO1993016596A1 (fr)
ZA (1) ZA931139B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004023876A1 (fr) 2002-09-12 2004-03-25 E.I. Du Pont De Nemours And Company Procede de preparation de compositions sulfonamides extrudees a partir d'une pate
WO2013155923A1 (fr) * 2012-04-20 2013-10-24 Rotam Agrochem International Company Limited Procédé de nettoyage d'une cuve de pulvérisation
WO2013165905A1 (fr) * 2012-05-01 2013-11-07 Monsanto Technology Llc Procédé de nettoyage de pesticide résiduel d'un conteneur agricole

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0124295A2 (fr) * 1983-04-04 1984-11-07 E.I. Du Pont De Nemours And Company Formulations aqueuses stabilisées de sulfonylurées
US4599412A (en) * 1983-11-23 1986-07-08 E. I. Du Pont De Nemours And Company Process for preparation of sulfonylurea solution formulations
EP0304282A1 (fr) * 1987-08-19 1989-02-22 E.I. Du Pont De Nemours And Company Procédé de préparation de sels de sulfonylurées

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
DE3246493A1 (de) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von wasserdispergierbaren granulaten

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0124295A2 (fr) * 1983-04-04 1984-11-07 E.I. Du Pont De Nemours And Company Formulations aqueuses stabilisées de sulfonylurées
US4599412A (en) * 1983-11-23 1986-07-08 E. I. Du Pont De Nemours And Company Process for preparation of sulfonylurea solution formulations
EP0304282A1 (fr) * 1987-08-19 1989-02-22 E.I. Du Pont De Nemours And Company Procédé de préparation de sels de sulfonylurées

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO333361B1 (no) * 2002-09-12 2013-05-13 Du Pont Fremgangsmate for fremstilling av pastaekstrudert sulfonamidherbicidsammensetning samt pastaekstrudert sulfonamidherbicidsammensetning fremstilt ved nevnte fremgangsmate.
EA007733B1 (ru) * 2002-09-12 2006-12-29 Е. И. Дюпон Де Немур Энд Компани Способ получения сульфонамидных композиций экструдированных паст
AU2003266010B2 (en) * 2002-09-12 2009-04-02 Fmc Corporation Process for preparing paste-extruded sulfonamide compositions
CN1681391B (zh) * 2002-09-12 2010-09-01 纳幕尔杜邦公司 制备糊料挤出的磺酰胺组合物的方法
US8071508B2 (en) 2002-09-12 2011-12-06 E. I. Du Pont De Nemours And Company Process for preparing paste-extruded sulfonamide compositions
CN101904337B (zh) * 2002-09-12 2012-08-15 纳幕尔杜邦公司 制备糊料挤出的磺酰胺组合物的方法
WO2004023876A1 (fr) 2002-09-12 2004-03-25 E.I. Du Pont De Nemours And Company Procede de preparation de compositions sulfonamides extrudees a partir d'une pate
US10051865B2 (en) 2012-04-20 2018-08-21 Rotam Agrochem International Company Limited Method for spray tank cleanout
GB2503416B (en) * 2012-04-20 2017-07-19 Rotam Agrochem Int Co Ltd Method for spray tank cleanout
GB2503416A (en) * 2012-04-20 2014-01-01 Rotam Agrochem Int Co Ltd Sulfonylurea composition for spray tank cleanout
EP2838358A4 (fr) * 2012-04-20 2015-09-23 Rotam Agrochem Int Co Ltd Procédé de nettoyage d'une cuve de pulvérisation
TWI569723B (zh) * 2012-04-20 2017-02-11 龍燈農業化工國際有限公司 噴霧桶清洗方法
WO2013155923A1 (fr) * 2012-04-20 2013-10-24 Rotam Agrochem International Company Limited Procédé de nettoyage d'une cuve de pulvérisation
US9681663B2 (en) 2012-04-20 2017-06-20 Rotam Agrochem International Company Limited Method for spray tank cleanout
WO2013165905A1 (fr) * 2012-05-01 2013-11-07 Monsanto Technology Llc Procédé de nettoyage de pesticide résiduel d'un conteneur agricole
US9657258B2 (en) 2012-05-01 2017-05-23 Monsanto Technology Llc Method of cleaning residual pesticide from an agricultural vessel
EP3851214A1 (fr) * 2012-05-01 2021-07-21 Monsanto Technology LLC Procédé de nettoyage de pesticide résiduel d'un conteneur agricole
US11091725B2 (en) 2012-05-01 2021-08-17 Monsanto Technology Llc Method of cleaning residual pesticide from an agricultural vessel
US12187988B2 (en) 2012-05-01 2025-01-07 Monsanto Technology Llc Method of cleaning residual pesticide from an agricultural vessel using a hydrogen peroxide source and ferrous ions

Also Published As

Publication number Publication date
CN1077838A (zh) 1993-11-03
LTIP345A (lt) 1994-04-25
JPH07503973A (ja) 1995-04-27
RU94040706A (ru) 1996-07-10
ZA931139B (en) 1994-08-18
LT3009B (lt) 1994-08-25
HUT71707A (en) 1996-01-29
AU3618793A (en) 1993-09-13
HU9402407D0 (en) 1994-11-28
CA2130118A1 (fr) 1993-09-02
EP0626807A1 (fr) 1994-12-07
BR9305997A (pt) 1997-10-21

Similar Documents

Publication Publication Date Title
CA1192194A (fr) Acides 2-¬¬(4-ethoxy-6 methylamino-1,3,5-triazin- 2-yl) aminocarbonyl| aminosulfonyl|benzoiques
TW201803448A (zh) 用以減少農藥殘留的農藥組合物
AU2084900A (en) Defoliant
EP0837632B1 (fr) Composition herbicide selective
EP0273610A1 (fr) Pyridinesulfonylurées herbicides
EP0774904B1 (fr) Melanges herbicides
DK170906B1 (da) Forbindelsen 2-[[N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-methylaminocarbonyl]aminosulfonyl]benzoesyremethylester, herbicide præparater og blandinger indeholdende forbindelsen, anvendelse af disse præparater og blandinger samt fremgangsmåde til forbindelsens fremstilling
US5106872A (en) Pesticidal compositions with enhanced activity
WO1993016596A1 (fr) Procede de nettoyage d&#39;un reservoir de pulverisation
US6180563B1 (en) Herbicidal synergistic composition and method of weed control
EP0318276A1 (fr) O-Méthoxycarbonylsulfonylurée herbicide
AU2008243445B2 (en) Defoliant
EP0272855B1 (fr) Pyridinesulfonamides herbicides
HK1041417A1 (zh) 以取代的苯基磺酰基氨基羰基三唑啉酮為基礎的選擇性除草劑
US10051865B2 (en) Method for spray tank cleanout
WO1988004294A2 (fr) Derives de l&#39;acide aryloxybenzene acetique a proprietes herbicides
EP0809436B1 (fr) Composition herbicide et procede de desherbage
EP0394324A1 (fr) o-CARBOMETHOXYSULFONYLUREE HERBICIDE
KR820001831B1 (ko) 제초제 조성물
CA1222757A (fr) N-thiazolysulfonyl-n&#39;-pyrimidylurees ou n&#39;-triazanylurees
EP0206772A2 (fr) Dérivés d&#39;acide aryloxybenzèneacétique herbicides
US4917719A (en) Herbicidal isothiazole derivatives
MXPA00002508A (en) Defoliant

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR CA CZ FI HU JP KP KR LK MG MN MW NO NZ PL RO RU SD SK UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1993905045

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 249415

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 2130118

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 1994 284463

Country of ref document: US

Date of ref document: 19940815

Kind code of ref document: A

WWP Wipo information: published in national office

Ref document number: 1993905045

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1993905045

Country of ref document: EP