WO2002043493A1 - Activateur d'action herbicide pour acides 2,4-dichlorophenoxyacetique et methylchlorophenoxyacetique - Google Patents

Activateur d'action herbicide pour acides 2,4-dichlorophenoxyacetique et methylchlorophenoxyacetique Download PDF

Info

Publication number
WO2002043493A1
WO2002043493A1 PCT/EP2001/013481 EP0113481W WO0243493A1 WO 2002043493 A1 WO2002043493 A1 WO 2002043493A1 EP 0113481 W EP0113481 W EP 0113481W WO 0243493 A1 WO0243493 A1 WO 0243493A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
acid
formula
methylchlorophenoxyacetic
composition according
Prior art date
Application number
PCT/EP2001/013481
Other languages
German (de)
English (en)
Inventor
Hans-Georg Mainx
Horst-Werner Wollenweber
Original Assignee
Cognis Deutschland Gmbh & Co. Kg
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 Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Priority to AU2002219129A priority Critical patent/AU2002219129A1/en
Publication of WO2002043493A1 publication Critical patent/WO2002043493A1/fr

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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof

Definitions

  • the present invention relates to herbicide-containing compositions which contain certain adjuvants for increasing the effectiveness of the herbicides.
  • 2,4 dichlorophenoxyacetic acid (2,4, D) and methyl chlorophenoxyacetic acid (MCPA), often collectively referred to as phenoxy herbicides are well-known, widely used herbicidal active ingredients which are characterized by good effectiveness and a favorable price. Since these active substances can cause a certain danger to the environment and are toxic to humans, ways are sought to increase the effectiveness in order to reduce the amount of the active substances used.
  • WO 96/22109 discloses the use of ethoxylated glycerides for the production of self-emulsifying aqueous crop protection agents. However, the document makes no statements about an effect-increasing effect for herbicides in such substance classes. From DE 198 23 252 it is known that alkoxylated alcohols can increase the effectiveness of herbicides. This effect is described for an alkoxylated rapeseed oil only for the insecticidal active ingredient allethrin.
  • alkoxylated compounds also have an activity-increasing effect in the case of phenoxy herbicides.
  • compositions which contain at least one agrochemical active compound selected from the group 2,4-dichlorophenoxyacetic acid or methylchlorophenoxyacetic acid, it containing at least one or more compounds of the general formula (I),
  • R represents a glycerol radical and R 'represents hydrogen and / or an ester group -CO-R ", in which R" represents a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms, m is a number is between 3 and 100 and n is a number between 1 and 50.
  • the agents according to the invention can contain both solid and liquid water-insoluble ingredients. They therefore form both dispersions and emulsions. In the context of this application, both types are summarized under the term dispersion.
  • the alkoxylated glycerol esters of the formula (I) are known substances which are described, for example, in US Pat. No. 2,678,935, US Pat. No. 3,539,518, US Pat. No. 4,022,808 or GB 1,050,497, the disclosure of which is also part of the present application.
  • R stands for a glyceride residue CH2O-CHO-CH2O in which the hydroxyl groups have been partially or completely alkoxylated.
  • Glyceride derivatives in which all the hydroxyl groups have been reacted with alkoxides are particularly preferred.
  • These alkoxylated glycerides according to formula (I) can be prepared by all methods known to the person skilled in the art.
  • One possibility is the direct reaction of glycerol esters with alkylene oxides in the presence of transition metal catalysts, as described in US Pat. No. 4,022,808.
  • the esters are preferably prepared by heterogeneously catalyzed direct alkoxylation of glycerides with ethylene oxide and propylene oxide on calcined or hydrophobized hydrotalcites.
  • the alkoxylated fatty acid esters contain at least 1 mole of propylene oxide groups per mole of ester, with a maximum of 50 moles of propylene oxide per mole of glyceride.
  • Compounds of the formula (I) which contain between 2 and 10 moles of propylene oxide per mole of ester are preferred. In addition to the propylene oxide units, there are between three and 100 ethylene oxide groups in the molecule.
  • Preferred compounds of the formula (I) are those which contain between 10 and 40 moles of ethylene oxide per mole of glycerol ester.
  • mixed ethylene oxide / propylene oxide adducts can be used both those compounds which have been reacted with a mixture of ethylene oxide and propylene oxide (random polymers), but also compounds which have been reacted in two separate steps with ethylene oxide and propylene oxide (block polymers ).
  • block polymers ethylene oxide and propylene oxide
  • Suitable fatty acid components are natural or synthetic fatty acids, in particular straight-chain, saturated or unsaturated C6-C30 fatty acids, including technical mixtures thereof, as are obtainable by fat splitting from animal and vegetable fats and oils, for example from coconut oil, Palm kernel oil, soybean oil, sunflower oil, turnip oil, cottonseed oil, fish oil, beef tallow and lard; specific examples are caprylic, capric, lauric, laurolein, myristic, myristoleic, palmitic, palmitoleic, oleic, elaidic, arachic, gadoleic, behenic and erucic acids.
  • Glycerin is selected as the alcohol component R. All hydroxyl groups of the alcohols are preferably substituted with the alkoxides, but not all terminal alkoxide radicals are sealed with ester groups. However, preference is given to those compounds of the formula (I) in which all the hydroxy groups of the alcohols are alkoxylated and all terminal alkoxide groups are furthermore sealed with ester groups of the formula -CO-R ". In these preferred compounds, the radical R" is in the formula (I) therefore only for a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms.
  • alkoxylated fatty acid esters of the formula (I) whose fatty acid component is selected from linear, unbranched C6 to Ci8 fatty acids and whose alcohol component is methanol, these esters of the formula (I) preferably between 1 and 3 mol of propylene oxide and contain between 1 and 6 moles of ethylene oxide per mole of ester.
  • Such compounds can be obtained, for example, by the above-described reactions of palmitic, stearic, oleic, linolinic or linolenic acid, lauric and myristic acid or their esters with alkoxides.
  • Glycerol esters are also suitable, the fatty acid component being selected from saturated or unsaturated, branched or unbranched fatty acids having 18 to 22 carbon atoms and the esters containing between 3 and 10 moles of propylene oxide per mole of ester and additionally containing between 10 and 40 moles of ethylene oxide per mole Contain esters.
  • Such compounds can be obtained, for example, by reacting glycerol esters of natural fatty acids such as palm oil, rapeseed oil, or preferably castor oil, with ethylene oxide.
  • the agents according to the invention necessarily contain herbicides from the group of phenoxy herbicides, selected from the group 2.4 dichlorophenoxyacetic acid and / or methylchlorophenoxyacetic acid (MCPA). It may also contain other herbicides or other crop protection agents. Plant protection products also include insecticides, acaricides, nematicides, but also repellents or rodenticides, sex attractants, mammals and bird deterrents and chemosterilants such as those used in the chemistry of plant protection and pesticides, Volume 1, publisher: R. Wegenier, Springer-Verlag Berlin, 1970, to be discribed. Depending on the active ingredient used, it may be necessary to adjust the agent to a specific pH value that is optimal for the active ingredient.
  • the aqueous compositions according to the invention can also contain other customary ingredients and additives. These include solvents such as ethylene or propylene glycols and Ci-C ⁇ alcohols, solid carriers such as lignin, lignin derivatives or clays and other known emulsifiers or dispersants.
  • solvents such as ethylene or propylene glycols and Ci-C ⁇ alcohols
  • solid carriers such as lignin, lignin derivatives or clays and other known emulsifiers or dispersants.
  • the compositions according to the invention are stable in storage even at temperatures above 30 ° C. and can be produced without the action of high shear forces, for example by manual stirring.
  • the agents according to the invention can be present as two-component concentrates which contain 1 to 99% by weight of phenoxy herbicides and 1 to 99% by weight of adjuvants according to formula (I). Preferably 10 to 90% by weight of herbicides and 90 to 10% by weight of adjuvants are contained. Agents which contain 5 to 90% by weight or 5 to 50% by weight of compounds of the formula (I) are particularly preferred.
  • the concentrates for their part are mixed with water to form ready-to-use spray liquors which are then applied to the plants to be protected using all of the techniques familiar to the person skilled in the art.
  • twin packs may also be mentioned here, in which active ingredient concentrate or active ingredient granules, preferably in a water-emulsifiable or dispersible form, are offered together with a separately packaged enhancer, which can be present both as a single component and in formulated form.
  • Another object of the present invention therefore relates to the use of compounds of the formula (I) as an enhancer in those compositions which contain at least 2,4-dichlorophenoxyacetic acid and / or methylchlorophenoxyacetic acid as herbicidal active ingredient.

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'objectif de la présente invention est d'intensifier l'action d'herbicides phénoxy, en particulier des acides 2,4-dichlorophénoxyacétique et méthylchlorophénoxyacétique, par l'addition de glycérides alcooxylées de formule R(C2H4O)n(C3H6O)m-R', dans laquelle R représente un reste glycérine et R' hydrogène et/ou un groupe ester CO-R'', dans lequel R'' signifie un reste alkyle ramifié ou linéaire, saturé ou insaturé avec 5 à 29 atomes C, n représente un nombre compris entre 3 et 100 et m un nombre compris entre 1 et 50.
PCT/EP2001/013481 2000-12-01 2001-11-21 Activateur d'action herbicide pour acides 2,4-dichlorophenoxyacetique et methylchlorophenoxyacetique WO2002043493A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002219129A AU2002219129A1 (en) 2000-12-01 2001-11-21 Enhancer for 2, 4-dichlorophenoxyacetic acid and methylchlorophenoxyacetic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2000159671 DE10059671A1 (de) 2000-12-01 2000-12-01 Wirkungsverstärker für 2,4 Dichlorphenoxyessigsäure und Methyl-chlorphenoxyessigsäure
DE10059671.1 2000-12-01

Publications (1)

Publication Number Publication Date
WO2002043493A1 true WO2002043493A1 (fr) 2002-06-06

Family

ID=7665376

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/013481 WO2002043493A1 (fr) 2000-12-01 2001-11-21 Activateur d'action herbicide pour acides 2,4-dichlorophenoxyacetique et methylchlorophenoxyacetique

Country Status (3)

Country Link
AU (1) AU2002219129A1 (fr)
DE (1) DE10059671A1 (fr)
WO (1) WO2002043493A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010105047A3 (fr) * 2009-03-11 2011-03-31 Monsanto Technology Llc Formulations herbicicides comprenant du glyphosate et des glycerides alcoxyles
WO2022112269A1 (fr) * 2020-11-27 2022-06-02 Nouryon Chemicals International B.V. Composition agrochimique liquide

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088887A1 (fr) * 1982-03-03 1983-09-21 Chemie Linz Aktiengesellschaft Emulsions concentrées stables à l'entreposage des esters herbicides d'acides phénoxyalcane carboxyliques et un procédé pour leur préparation
US4681900A (en) * 1984-01-13 1987-07-21 Kao Corporation Biocide activator
EP0522891A1 (fr) * 1991-07-09 1993-01-13 Rhone-Poulenc Chimie Mélanges aqueux homogènes, stables et versables et utilisation desdits mélanges pour préparer des dispersions de substances insolubles dans l'eau
WO1999060851A1 (fr) * 1998-05-26 1999-12-02 Cognis Deutschland Gmbh Agent aqueux contenant des principes actifs agrochimiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088887A1 (fr) * 1982-03-03 1983-09-21 Chemie Linz Aktiengesellschaft Emulsions concentrées stables à l'entreposage des esters herbicides d'acides phénoxyalcane carboxyliques et un procédé pour leur préparation
US4681900A (en) * 1984-01-13 1987-07-21 Kao Corporation Biocide activator
EP0522891A1 (fr) * 1991-07-09 1993-01-13 Rhone-Poulenc Chimie Mélanges aqueux homogènes, stables et versables et utilisation desdits mélanges pour préparer des dispersions de substances insolubles dans l'eau
WO1999060851A1 (fr) * 1998-05-26 1999-12-02 Cognis Deutschland Gmbh Agent aqueux contenant des principes actifs agrochimiques

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010105047A3 (fr) * 2009-03-11 2011-03-31 Monsanto Technology Llc Formulations herbicicides comprenant du glyphosate et des glycerides alcoxyles
CN102438455A (zh) * 2009-03-11 2012-05-02 孟山都技术公司 包含草甘膦和烷氧基化甘油酯的除草配制剂
AU2010224073B2 (en) * 2009-03-11 2014-11-20 Akzo Nobel Chemicals International B.V. Herbicidal formulations comprising glyphosate and alkoxylated glycerides
CN106386848A (zh) * 2009-03-11 2017-02-15 阿克佐诺贝尔股份有限公司 包含草甘膦和烷氧基化甘油酯的除草配制剂
US9723841B2 (en) 2009-03-11 2017-08-08 Akzo Nobel N.V. Herbicidal formulations comprising glyphosate and alkoxylated glycerides
CN106386848B (zh) * 2009-03-11 2022-01-11 阿克苏诺贝尔化学品国际有限公司 包含草甘膦和烷氧基化甘油酯的除草配制剂
WO2022112269A1 (fr) * 2020-11-27 2022-06-02 Nouryon Chemicals International B.V. Composition agrochimique liquide

Also Published As

Publication number Publication date
AU2002219129A1 (en) 2002-06-11
DE10059671A1 (de) 2002-06-06

Similar Documents

Publication Publication Date Title
DE69028114T2 (de) Auf fettsäuren basierende emulgierbare konzentrate mit herbizider wirkung
DE3818293C2 (de) Verfahren zur Herstellung von nichtionogenen Tensiden, deren Verwendung sowie Zubereitungen unter Verwendung derselben
DD251748A5 (de) Verfahren zur herstellung von estern der zitronensaeure
DE69016178T2 (de) Zusammensetzung von Nachlaufherbiziden, die Silikonglycole mit Acetoxyendgruppen sowie Dispergiermittel enthalten.
EP1082007B1 (fr) Agents aqueux contenant des principes actifs agrochimiques
WO2000051427A1 (fr) Emulsions pit
WO2001076368A1 (fr) Produit aqueux herbicide
EP1246531A1 (fr) Agent herbicide aqueux
WO2002043493A1 (fr) Activateur d'action herbicide pour acides 2,4-dichlorophenoxyacetique et methylchlorophenoxyacetique
EP1401273A1 (fr) Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires
DE19906368A1 (de) Emulgatoren
DE2354467C3 (de) Fungizide Dispersionen auf Basis von Benzimidazolmethylcarbamat
WO2002069705A1 (fr) Adjuvants d'agents phytoprotecteurs biologiques
DE69202498T2 (de) Pflanzenschutz-Suspoemulsionen.
WO1993005129A1 (fr) Emulsions du type 'huile dans l'eau' de composants huileux polaires
DE2354468C3 (de) Fungizide Dispersionen auf Basis von Benzimidazolmethylcarbamat
WO2001051432A1 (fr) Agents aqueux contenant des micronutriments pour plantes
US6759371B2 (en) Bromoxynil component-containing herbicidal preparations with enhanced penetration and methods of using same
CH660126A5 (de) Antimykotisches mittel und verfahren zu seiner herstellung.
DE10136804A1 (de) Umsetzungsprodukte von langkettigen Carbonsäuren

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase