EP1401273A1 - Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires - Google Patents

Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires

Info

Publication number
EP1401273A1
EP1401273A1 EP02762300A EP02762300A EP1401273A1 EP 1401273 A1 EP1401273 A1 EP 1401273A1 EP 02762300 A EP02762300 A EP 02762300A EP 02762300 A EP02762300 A EP 02762300A EP 1401273 A1 EP1401273 A1 EP 1401273A1
Authority
EP
European Patent Office
Prior art keywords
formula
use according
compounds
oil
saturated
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.)
Withdrawn
Application number
EP02762300A
Other languages
German (de)
English (en)
Inventor
Hans-Georg Mainx
Horst-Werner Wollenweber
Claudia GRÜNEWALD
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and 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 and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1401273A1 publication Critical patent/EP1401273A1/fr
Withdrawn legal-status Critical Current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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/04—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 no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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 present invention relates to improving the rain resistance of crop protection agents by adding certain alkoxylated compounds.
  • RO stands for an alcohol radical selected from the group of the branched or linear, saturated or unsaturated monohydric alcohols with 1 to 6 C atoms or the polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups and R 'represents hydrogen and / or a group -CO- R "in which R" is a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms, n is a number between 1 and 50 and m is zero or a number between 1 and 20 means to improve the rain resistance of agrochemicals when such compositions are applied to plant surfaces.
  • Agrochemicals are broadly understood to mean all compounds which contain active ingredients from the group of fertilizers, pesticides, plant strengthening agents or other active substances for use in crop production.
  • the use in pesticide-containing formulations is particularly preferred, since particularly expensive application is required there because of the expensive and ecologically critical ingredients.
  • alkoxylated compounds of the formula (I) are substances known per se, which are described, for example, in US Pat. No. 2,678,935, the disclosure of which is also part of the present application,
  • the compounds of formula (I) can be prepared by all methods known to those skilled in the art, e.g. by esterification of fatty acids with alkoxylated methanol, as described in US Pat. No. 3,539,518.
  • this process has some disadvantages, it has two stages, the esterification takes a very long time and the products are colored by the high reaction temperatures.
  • fatty acid methyl ester ethoxylates produced in this way have relatively high OH numbers after the esterification, which can be problematic for some applications.
  • Another possibility is the direct reaction of fatty acid esters with alkylene oxides in the presence of transition metal catalysts, as described in US Pat. No. 4,022,808.
  • the fatty acid alkyl ester alkoxylates are preferably prepared by heterogeneously catalyzed direct alkoxylation of fatty acid alkyl esters with ethylene oxide and / or propylene oxide on calcined or hydrophobized hydrotalcites.
  • This synthesis method is described in detail in the laid-open publications WO 90/13533 and WO 91/15441, the disclosure of which is also part of the present application.
  • the resulting products are characterized by a low OH number, the reaction is carried out in one step and light-colored products are obtained.
  • the fatty acid alkyl esters used as starting materials can be obtained from natural oils and fats or produced synthetically.
  • the alkoxylated fatty acid esters contain at least 1 mole of ethylene oxide groups per mole of ester. Preference is given to compounds of the formula (I) which contain between 1 and 50, preferably 1 and 30, mol of ethylene oxide per mole of ester. It is preferred that, in addition to the ethylene oxide units, between one and 10 propylene oxide groups are contained in the molecule. Those compounds of the formula (I) which contain between 1 and 30 moles of ethylene oxide per mole of ester and 1 to 10 moles of propylene oxide groups are also preferred.
  • mixed ethylene oxide / propylene oxide adducts can be used both with a mixture of ethylene oxide and Propylene oxide were implemented, but also compounds that were reacted with ethylene oxide and propylene oxide in two separate steps. Depending on the manufacturing process, the alkoxides are statistically distributed among the OH groups present.
  • 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, Beet or rapeseed oil, cottonseed oil, fish oil, beef tallow and lard; specific examples are caprylic, capric, lauric, lauroleic, myristic, myristoleic, palmitic, palmitoleic, oleic, linoleic, linolenic, elaidic, arachic, gadoleic, behenic and erucic acids.
  • Straight-chain or branched, saturated or unsaturated monohydric alcohols having 1 to 6 carbon atoms e.g. Methanol, ethanol, n- and i-propanol, n- and i-butanol, pentanol, hexanol, 2-ethylhexanol and cyclohexanol are suitable.
  • Polyols having 2 to 6 carbon atoms for example ethylene glycol, 1, 2-propylene glycol, 1, 2-butylene glycol, glycerol or trimethylolpropane and penthaerythritol can be used.
  • all hydroxyl groups of the alcohols are substituted with the alkoxides, but not all terminal alkoxide residues are sealed with ester groups.
  • the agents can therefore contain both compounds of the formula (I) which are obtained by reacting the full esters and the partial esters with alkoxides.
  • preference is given to those compounds of the formula (I) in which all the hydroxyl groups of the alcohols are alkoxylated and all terminal alkoxide groups are furthermore closed with ester groups of the formula -CO-R ".
  • 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.
  • those alkoxylated fatty acid esters of the formula (I) are preferably used whose fatty acid component is selected from linear, unbranched C ⁇ to Ci ⁇ fatty acids and whose alcohol component is methanol, these esters of the formula (I) preferably between 1 and 3 mol propylene oxide and 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.
  • unsaturated acids can also be used successfully in the sense of the present technical teaching.
  • unsaturated, preferably polyunsaturated, compounds are selected.
  • Unsaturated carboxylic acids with iodine numbers (IZ) in the range from 100 to 170 are particularly preferred.
  • Soybean oil, sunflower oil, rapeseed oil, cottonseed oil and fish oil are preferred as the natural raw material base for such fatty acids.
  • alkoxylated compounds in which glycerol is used as the alcohol component and the fatty acid component is selected from saturated or unsaturated, branched or unbranched fatty acids with 18 to 22 carbon atoms and the esters contain between 1 and 3 moles of ethylene oxide per mole of ester.
  • glycerol is used as the alcohol component
  • the fatty acid component is selected from saturated or unsaturated, branched or unbranched fatty acids with 18 to 22 carbon atoms and the esters contain between 1 and 3 moles of ethylene oxide per mole of ester.
  • Compounds of the formula (I) in which n is 5, 10, 30 or 50 and m is zero are particularly preferred.
  • Such compounds can be obtained, for example, by reacting glycerol esters of natural fatty acids such as, for example, palm, rapeseed, soybean, linseed, poppy or castor oil with ethylene oxide.
  • glycerol esters of natural fatty acids such as, for example, palm, rapeseed, soybean, linseed, poppy or castor oil
  • castor, soybean linseed and rapeseed oil ethoxylates is preferred, the use of rapeseed soybean and / or linseed oil ethoxylates being preferred, preferably with 5-50 moles of ethylene oxide per mole of oil.
  • rapeseed oil, soybean or linseed oil ethoxylates it is further preferred to use derivatives with 5-40 and in particular 5-20 and in particular 5-10 moles of ethylene oxide.
  • the vegetable oils described above as the raw material base for the alkoxylates used according to the invention it has also proven to be advantageous to use products based on fish oil.
  • the compounds of the formula (I) can additionally contain propylene oxide units, these compounds then having 1 to 5 mol of propylene oxide in the molecule.
  • Rapeseed contains about 40-50% oil u. approx. 30% protein. The melting point is 0-2 ° C.
  • Old rapeseed varieties contain high proportions (35-64%) erucic acid, 5-10% gondo acid [(Z) -11-eicosenoic acid, C20H38O2, molecular weight 310.52, melting point 24-25 ° C] and. Nervonic acid in addition to 13-38% oleic acid, 10-22% linoleic acid and 2-10% linolenic acid.
  • New rapeseed varieties usually contain ⁇ 2% of the long-chain mono fatty acids.
  • Linseed oil is a golden yellow, slightly yellowish, fat, drying oil in the bleached state, which is extracted from the crushed linseed seeds (see flax) in the cold with the help of multi-stage presses at a pressure of 180-350 bar and a yield of 20-30 % is obtained.
  • the press residue (press cake, oil cake) still contains 7-8% oil.
  • the mucilages adhering to the crude oil are removed by heating to 280 ° C. or filtering with bleaching earth.
  • Linseed oil is a complex mixture of glycerol esters of predominantly unsaturated fatty acids. Of all fats and oils, linseed oil has the highest iodine number.
  • Soybean oil is a yellowish to brownish-yellow, fatty, semi-drying oil that is obtained from soybeans or soybean meal by pressing and / or extraction with hydrocarbons (e.g. hexane). Soybean oil content: 17-22%. 55-65% of the total fatty acids in soybean oil are polyunsaturated fatty acids. The sterol content of soybean oil averages 0.37% (of which cholesterol 0.3-0.5%). Refining can reduce the sterol content by approx. 30%. Soybean oil also contains free fatty acids, lecithin and up to 0.8% tocopherol.
  • Fish oil itself is a well-known raw material, the collective term for poorly drying oils, which are extracted from the whole body of herring fish such as anchovies, herring, sardines or sprats or from the waste from fish processing by extraction or squeezing.
  • the high proportion of polyunsaturated fatty acids with 4-6 double bonds is characteristic of the composition of fish oils.
  • the proportion of tocopherol with an autoxidative effect is relatively low. It can be advantageous to use fatty acids based on herring oil according to the invention.
  • the compounds of the formula (I) used according to the invention are nonionic compounds which can also be characterized by their HLB value (hydrophilic-lipophilic balance as defined by Griffin; see Römpp Lexikon Chemie, 10th edition 1997, page 1764). Those agents are preferred which contain compounds of the formula (I) with HLB values between 4 and 10 and in particular between 5 and 9.
  • the compounds of the formula (I) are used as adjuvants in customary agrochemical formulations.
  • Liquid, in particular aqueous, formulations are preferably prepared from crop protection agents and adjuvants and then used. These are, for example, spray liquors but also so-called tank mixes.
  • the compounds of the formula (I) according to the invention are preferably present in amounts of 0.05 to 5% by weight in the agrochemical compositions which are suitable for use, but in particular in amounts of 0.1 to 1% by weight. In principle, however, the compounds of the formula (I) can also be introduced into solid formulations. The compounds of formula (I) can also serve as a formulation component of liquid concentrates.
  • the present invention further relates to a process for improving the rain resistance of, in particular, aqueous crop protection agents by adding compounds of the formula (I) to these agents in effective amounts, preferably in amounts of 0.05 to 5% by weight, based on the agents, added.
  • Injectable formulations were produced from the active substances and compounds of the formula (I) according to the invention in accordance with the emulsifier content of the commercial formulations and were applied in accordance with the instructions for use of the manufacturers. After 2 or 24 hours, the test plants were grown over a period of 6.5 hours. treated with 25 mm artificial rain. The residues of the agents on the plants were then measured.
  • RSO stands for rapeseed oil derivative.
  • the residue of the crop protection agent on the plants was measured by means of GC analysis.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne l'utilisation de composés de formule générale (I), RO-(C2H4O)n(C3H6O)m-R', dans laquelle RO représente un reste alcool, sélectionné dans le groupe des alcools monovalents, ramifiés ou linéaires, saturés ou insaturés, ayant 1 à 6 atomes C, ou des polyols ayant 2 à 12 atomes C et 2 à 6 groupes hydroxyle, et R' représente hydrogène et/ou un groupe ester -CO-R', dans lequel R' représente un reste alkyle, ramifié ou linéaire, saturé ou insaturé, ayant 5 à 29 atomes C ; n est un nombre compris entre 1 et 50 et m représente zéro ou un nombre compris entre 1 et 20, dans des produits agrochimiques, de manière à augmenter la résistance à la pluie de ces produits lorsqu'ils sont appliqués sur des surfaces végétales.
EP02762300A 2001-07-04 2002-06-25 Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires Withdrawn EP1401273A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10132459 2001-07-04
DE10132459A DE10132459A1 (de) 2001-07-04 2001-07-04 Verfahren zur Verbesserung der Regenfestigkeit von Pflanzenschutzmitteln
PCT/EP2002/006984 WO2003003830A1 (fr) 2001-07-04 2002-06-25 Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires

Publications (1)

Publication Number Publication Date
EP1401273A1 true EP1401273A1 (fr) 2004-03-31

Family

ID=7690612

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02762300A Withdrawn EP1401273A1 (fr) 2001-07-04 2002-06-25 Procede permettant d'ameliorer la resistance a la pluie de produits phytosanitaires

Country Status (6)

Country Link
US (1) US20040171492A1 (fr)
EP (1) EP1401273A1 (fr)
BR (1) BR0210779A (fr)
CA (1) CA2452297A1 (fr)
DE (1) DE10132459A1 (fr)
WO (1) WO2003003830A1 (fr)

Families Citing this family (9)

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Publication number Priority date Publication date Assignee Title
US20070049499A1 (en) * 2005-08-24 2007-03-01 Basf Corporation. Pesticide composition
TW200843642A (en) * 2007-03-08 2008-11-16 Du Pont Liquid sulfonylurea herbicide formulations
EP2266394A1 (fr) * 2009-06-17 2010-12-29 Cognis IP Management GmbH Compositions agricoles non aqueuses
EP2533631B1 (fr) * 2010-02-12 2017-11-22 Basf Se Composition anhydre comprenant un pesticide en solution et un pesticide en suspension, un lactate d'alkyle et un alcool
US20110201500A1 (en) * 2010-02-12 2011-08-18 Basf Se Anhydrous Composition Comprising a Dissolved and a Suspended Pesticide, Alkyl Lactate and Alcohol
ES2541592T3 (es) * 2010-05-08 2015-07-22 Cognis Ip Management Gmbh Composiciones biocidas que comprenden ésteres de oligoglicerol alcoxilado
GB201220886D0 (en) 2012-11-20 2013-01-02 Croda Int Plc Penetrants for agrochemical formulations
US20150189869A1 (en) * 2014-01-06 2015-07-09 Exacto, Inc. Compositions comprising ethoxylated lecithin and methods of making and using the same
CN114025609A (zh) * 2019-05-08 2022-02-08 拜耳公司 用于除草剂的高铺展ulv制剂

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DE4010606A1 (de) * 1990-04-02 1991-10-10 Henkel Kgaa Verwendung von hydrophobierten hydrotalciten als katalysatoren fuer die ethoxylierung bzw. propoxylierung
JP2959949B2 (ja) * 1993-03-26 1999-10-06 ライオン株式会社 農薬用展着剤
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Also Published As

Publication number Publication date
DE10132459A1 (de) 2003-01-23
BR0210779A (pt) 2004-07-20
CA2452297A1 (fr) 2003-01-16
WO2003003830A1 (fr) 2003-01-16
US20040171492A1 (en) 2004-09-02

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