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WO1997031535A1 - Agents herbicides a base de n-phosphonomethylglycinesters - Google Patents

Agents herbicides a base de n-phosphonomethylglycinesters Download PDF

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Publication number
WO1997031535A1
WO1997031535A1 PCT/EP1997/000732 EP9700732W WO9731535A1 WO 1997031535 A1 WO1997031535 A1 WO 1997031535A1 EP 9700732 W EP9700732 W EP 9700732W WO 9731535 A1 WO9731535 A1 WO 9731535A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
group
active ingredient
ethyl
active
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/EP1997/000732
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Uwe Priesnitz
Raphael Wieschollek
Markus Dollinger
Ingo Wetcholowsky
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
Priority to AU18737/97A priority Critical patent/AU1873797A/en
Publication of WO1997031535A1 publication Critical patent/WO1997031535A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention relates to new herbicidal compositions which consist of pure - not formulated - N-phosphonomethylglycine esters and dissolved or dispersed in water - previously formulated - other known, herbicidally active compounds or combinations of such known, herbicidally active compounds getting produced.
  • N-phosphonomethylglycine alkyl esters have herbicidal properties and - generally in formulated use forms, ie combined with certain additives - can be used to kill unwanted plants (cf. DE 2152826, DE 2166573, US) 3977860). That pure - i.e. active ingredients which are not formulated - are used in spray liquors, but is not common.
  • N-phosphonomethylglycine esters of the general formula (I) N-phosphonomethylglycine esters of the general formula (I)
  • R represents alkyl
  • the invention thus relates to herbicidal compositions, characterized by an effective content of a synergistic active ingredient combination consisting of (a) an N-phosphonomethylglycine ester of the above formula (I), in which R represents alkyl, or an acid adduct of these compounds (“active ingredient of group 1”) and
  • N-phosphonomethylglycine esters of the general formula (I) - and acid adducts of compounds of the formula (I) - in pure, non-formulated form for use in spray liquors of known, formulated herbicidal active compounds can be used and that these spray liquors show extremely synergistic properties in comparison with corresponding application forms of the individual active ingredients.
  • N-phosphonomethylglycine esters of the formula (I) directly in spray liquors without the use of formulation auxiliaries is a significant simplification of the application and thus a valuable enrichment of the prior art.
  • the invention preferably relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • R represents straight-chain or branched alkyl having 1 to 10 carbon atoms
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,
  • Fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethylbenzene , Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,
  • Tebutam Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,
  • the invention particularly relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • R represents straight-chain or branched alkyl having 2 to 4 carbon atoms
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron (Bensulfuron)
  • a particularly preferred group 1 active ingredient is N-phosphonomethylglycine ethyl ester
  • Suitable acids are preferably strong protonic acids, such as hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, and tonic sulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid
  • N-phosphonomethylglycine esters of the general formula (I) are obtained if N-phosphonomethylglycine of the formula (II)
  • an acid such as, for example, hydrogen chloride (hydrogen chloride)
  • an acid binder such as e.g. triethylamine or propylene oxide
  • herbicidal compositions to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and for minimum
  • Tillage processes are used. They are also suitable as burners (killing herbs, e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Further areas of application are tree nurseries, forestry, grassland and ornamental plant cultivation
  • Scirpus Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera
  • the use of the active compounds and combinations of active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other 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. In general, 1 part by weight of active ingredient in group 1 accounts for 0.001 to 1000 parts by weight, preferably 0.01 to
  • 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 0.05 and 5 kg of active ingredient combination per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between 0.1 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 processes. However, they are preferably used in the post-emergence process.
  • a herbicide always has a synergistic effect if the herbicidal action of the active compound combination is greater than that of the individual applied active compounds.
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.
  • Hydrogen chloride gas is introduced into a suspension of 200 g (1.2 mol) of N-phosphonomethylglycine in 3000 ml of ethanol until saturation. Then the
  • Fluid bed drying, blade drying or circulating air drying in each case combined with conventional comminution processes, such as air jet milling, crushers, rollers, grinding, if appropriate).
  • Hydrogen chloride gas is introduced into a suspension of 5.1 g (30 mmol) of N-phosphonomethyl-glycine in 80 ml of ethanol until saturation.
  • the reaction mixture is heated under reflux for 2 hours and then concentrated in a water jet vacuum.
  • the residue is mixed with acetone stirred and the kristal ⁇ line product isolated by suction

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)

Abstract

L'invention concerne des agents herbicides caractérisés en ce qu'ils contiennent une quantité efficace d'une combinaison synergique de substances comprenant: a) un N-phosphonométhylglicinester de la formule (I): (HO)2P(O)-CH2-NH-CH2-CO-O-R dans laquelle R représente un groupe alkyle ou un produit d'addition d'acide de tels composés ('substance du groupe 1); et b) au moins un composé choisi dans le groupe des autres herbicides connus ('substance du groupe 2'). Ledit agent contient 0,001 à 1000 parties en poids de substance du groupe 2 pour une partie en poids de substance du groupe 1.
PCT/EP1997/000732 1996-02-29 1997-02-17 Agents herbicides a base de n-phosphonomethylglycinesters Ceased WO1997031535A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18737/97A AU1873797A (en) 1996-02-29 1997-02-17 Herbicidal agents based on n-phosphonomethylglycine esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996107633 DE19607633A1 (de) 1996-02-29 1996-02-29 Herbizide Mittel auf Basis von N-Phosphonomethyl-glycinestern
DE19607633.1 1996-02-29

Publications (1)

Publication Number Publication Date
WO1997031535A1 true WO1997031535A1 (fr) 1997-09-04

Family

ID=7786751

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/000732 Ceased WO1997031535A1 (fr) 1996-02-29 1997-02-17 Agents herbicides a base de n-phosphonomethylglycinesters

Country Status (3)

Country Link
AU (1) AU1873797A (fr)
DE (1) DE19607633A1 (fr)
WO (1) WO1997031535A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000074487A1 (fr) * 1999-06-07 2000-12-14 Sumitomo Chemical Company, Limited Composition herbicide
US6369001B1 (en) 1999-08-11 2002-04-09 Monsanto Technology, Llc Microemulsion coformulation of a graminicide and a water-soluble herbicide
US6451732B1 (en) * 1999-06-04 2002-09-17 Syngenta, Limited Herbicidal compositions of glyphosate trimesium
DE10157339A1 (de) * 2001-11-22 2003-06-12 Bayer Cropscience Gmbh Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Benzoylpyrazole
US7008904B2 (en) 2000-09-13 2006-03-07 Monsanto Technology, Llc Herbicidal compositions containing glyphosate and bipyridilium
US7422998B2 (en) * 1998-08-13 2008-09-09 Aventis Cropscience Gmbh Herbicidal compositions for tolerant or resistant sugar beet crops
JP2009001578A (ja) * 1996-09-05 2009-01-08 Syngenta Participations Ag 雑草の抑制方法
EP2319317A1 (fr) * 1998-08-13 2011-05-11 Bayer CropScience AG Agents herbicides pour cultures de coton tolérantes ou résistantes
EP2327305A1 (fr) * 1998-08-13 2011-06-01 Bayer CropScience AG Agents herbicides pour cultures de soja tolérantes ou résistantes
US8324132B2 (en) 2010-03-31 2012-12-04 E. I. Du Pont De Nemours And Company Mixture and method for controlling undesired vegetation
US8536094B2 (en) 1998-08-13 2013-09-17 Bayer Intellectual Property Gmbh Herbicidal compositions for tolerant or resistant rice crops
US8815773B2 (en) 2009-07-29 2014-08-26 Upl Limited Herbicidal combination
WO2015170876A1 (fr) * 2014-05-07 2015-11-12 선문그린사이언스 주식회사 Mélange herbicide synergique comprenant du dibromure de diquat et un herbicide non sélectif
US10285404B2 (en) 2013-02-27 2019-05-14 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
US10334849B2 (en) 2011-10-26 2019-07-02 Monsanto Technology Llc Salts of carboxylic acid herbicides
US10499646B2 (en) 2004-03-10 2019-12-10 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US10736322B2 (en) 2012-06-04 2020-08-11 Monsanto Technology Llc Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3799758A (en) * 1971-08-09 1974-03-26 Monsanto Co N-phosphonomethyl-glycine phytotoxicant compositions
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
WO1984003607A1 (fr) * 1983-03-16 1984-09-27 Chevron Res Compositions herbicides du type glyphosate
EP0143547A1 (fr) * 1983-10-28 1985-06-05 Chevron Research Company Compositions herbicides du type glyphosate et leurs utilisations
EP0162326A2 (fr) * 1984-05-02 1985-11-27 Hoechst Aktiengesellschaft Agents herbicides
GB2169806A (en) * 1985-01-23 1986-07-23 Rhone Poulenc Agrochimie Herbicidal mixtures based on n-(phosphonomethylglycyl)sulphonylamine
EP0281103A2 (fr) * 1987-03-05 1988-09-07 Teijin Limited Composés de l'acide phénoxycarboxylique et herbicide les contenant comme ingrédient actif
WO1989003641A1 (fr) * 1987-10-28 1989-05-05 Rhone Poulenc Agrochimie Compositions comprenant des combinaisons d'herbicides de type glyphosate et de type phenoxybenzoique
DE19528056A1 (de) * 1995-07-31 1997-02-06 Bayer Ag Iso-Butylester und sec-Butylester von N-Phosphonomethyl-glycin
DE19533523A1 (de) * 1995-09-11 1997-03-13 Bayer Ag Verwendung von N-Phosphonomethyl-glycinestern in wäßriger Lösung als Herbizide

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3799758A (en) * 1971-08-09 1974-03-26 Monsanto Co N-phosphonomethyl-glycine phytotoxicant compositions
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
WO1984003607A1 (fr) * 1983-03-16 1984-09-27 Chevron Res Compositions herbicides du type glyphosate
EP0143547A1 (fr) * 1983-10-28 1985-06-05 Chevron Research Company Compositions herbicides du type glyphosate et leurs utilisations
EP0162326A2 (fr) * 1984-05-02 1985-11-27 Hoechst Aktiengesellschaft Agents herbicides
GB2169806A (en) * 1985-01-23 1986-07-23 Rhone Poulenc Agrochimie Herbicidal mixtures based on n-(phosphonomethylglycyl)sulphonylamine
EP0281103A2 (fr) * 1987-03-05 1988-09-07 Teijin Limited Composés de l'acide phénoxycarboxylique et herbicide les contenant comme ingrédient actif
WO1989003641A1 (fr) * 1987-10-28 1989-05-05 Rhone Poulenc Agrochimie Compositions comprenant des combinaisons d'herbicides de type glyphosate et de type phenoxybenzoique
DE19528056A1 (de) * 1995-07-31 1997-02-06 Bayer Ag Iso-Butylester und sec-Butylester von N-Phosphonomethyl-glycin
DE19533523A1 (de) * 1995-09-11 1997-03-13 Bayer Ag Verwendung von N-Phosphonomethyl-glycinestern in wäßriger Lösung als Herbizide

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
AGROKHIMIYA, no. 7, 1987, pages 100 - 104 *
C.TOMLIN: "The Pesticide Manual, Tenth Edition", 1995, BRITISH CROP PROTECTION COUNCIL, FARNHAM, GB, XP002031460 *
DATABASE CROPU STN-International; E.P.UGRYUMOV ET AL.: "Herbicidal Activity of Some N-Phosphonomethylglycine Esters", XP002031461 *
DISCLOSED ANONYMOUSLY: "Herbicidal mixtures", RESEARCH DISCLOSURE, June 1973 (1973-06-01), HAVANT GB, pages 62 - 65, XP002031459 *

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009001578A (ja) * 1996-09-05 2009-01-08 Syngenta Participations Ag 雑草の抑制方法
EP1107668B2 (fr) † 1998-08-13 2018-10-03 Bayer CropScience AG Agents herbicides pour cultures de betterave a sucre tolerantes ou resistantes
EP2329718A1 (fr) * 1998-08-13 2011-06-08 Bayer CropScience AG Agents herbicides pour cultures de soja tolérantes ou résistantes
EP2327305A1 (fr) * 1998-08-13 2011-06-01 Bayer CropScience AG Agents herbicides pour cultures de soja tolérantes ou résistantes
EP2327306A1 (fr) * 1998-08-13 2011-06-01 Bayer CropScience AG Agents herbicides pour cultures de coton tolérantes ou résistantes
EP2319317A1 (fr) * 1998-08-13 2011-05-11 Bayer CropScience AG Agents herbicides pour cultures de coton tolérantes ou résistantes
US8536094B2 (en) 1998-08-13 2013-09-17 Bayer Intellectual Property Gmbh Herbicidal compositions for tolerant or resistant rice crops
US7422998B2 (en) * 1998-08-13 2008-09-09 Aventis Cropscience Gmbh Herbicidal compositions for tolerant or resistant sugar beet crops
EP2329719A1 (fr) * 1998-08-13 2011-06-08 Bayer CropScience AG Agents herbicides pour cultures de soja tolérantes ou résistantes
US6451732B1 (en) * 1999-06-04 2002-09-17 Syngenta, Limited Herbicidal compositions of glyphosate trimesium
WO2000074487A1 (fr) * 1999-06-07 2000-12-14 Sumitomo Chemical Company, Limited Composition herbicide
US6576592B1 (en) 1999-06-07 2003-06-10 Sumitomo Chemical Company, Limited Herbicide composition
EP1183949A4 (fr) * 1999-06-07 2002-09-25 Sumitomo Chemical Co Composition herbicide
US6369001B1 (en) 1999-08-11 2002-04-09 Monsanto Technology, Llc Microemulsion coformulation of a graminicide and a water-soluble herbicide
CN100512643C (zh) * 1999-08-11 2009-07-15 孟山都技术有限责任公司 禾本科除草剂和水溶性除草剂的微乳合剂
US7989392B2 (en) * 2000-09-13 2011-08-02 Monsanto Technology, Llc Herbicidal compositions containing glyphosate bipyridilium
US7008904B2 (en) 2000-09-13 2006-03-07 Monsanto Technology, Llc Herbicidal compositions containing glyphosate and bipyridilium
DE10157339A1 (de) * 2001-11-22 2003-06-12 Bayer Cropscience Gmbh Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Benzoylpyrazole
CN101326914B (zh) * 2001-11-22 2012-10-10 拜尔作物科学股份公司 含有选自苯甲酰基吡唑类除草剂的增效除草组合物
CN101326914A (zh) * 2001-11-22 2008-12-24 拜尔作物科学股份公司 含有选自苯甲酰基吡唑类除草剂的增效除草组合物
CN101485326A (zh) * 2001-11-22 2009-07-22 拜尔作物科学股份公司 含有选自苯甲酰基吡唑类除草剂的增效除草组合物
US10499646B2 (en) 2004-03-10 2019-12-10 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US11864558B2 (en) 2004-03-10 2024-01-09 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US8815773B2 (en) 2009-07-29 2014-08-26 Upl Limited Herbicidal combination
US8324132B2 (en) 2010-03-31 2012-12-04 E. I. Du Pont De Nemours And Company Mixture and method for controlling undesired vegetation
US10334849B2 (en) 2011-10-26 2019-07-02 Monsanto Technology Llc Salts of carboxylic acid herbicides
US10736322B2 (en) 2012-06-04 2020-08-11 Monsanto Technology Llc Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts
US10285404B2 (en) 2013-02-27 2019-05-14 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
US11399544B2 (en) 2013-02-27 2022-08-02 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
US12458027B2 (en) 2013-02-27 2025-11-04 Monsanto Technology Llc Glyphosate composition for dicamba tank mixtures with improved volatility
WO2015170876A1 (fr) * 2014-05-07 2015-11-12 선문그린사이언스 주식회사 Mélange herbicide synergique comprenant du dibromure de diquat et un herbicide non sélectif
KR101615174B1 (ko) 2014-05-07 2016-04-26 선문그린사이언스 주식회사 다이쿼트디브로마이드와 비선택성 제초제를 포함하는 상승작용적 제초제 혼합물

Also Published As

Publication number Publication date
DE19607633A1 (de) 1997-09-04
AU1873797A (en) 1997-09-16

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