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WO1996019111A1 - Utilisation d'esters d'acide laurique comme renforcateurs de la puissance de principes actifs - Google Patents

Utilisation d'esters d'acide laurique comme renforcateurs de la puissance de principes actifs Download PDF

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Publication number
WO1996019111A1
WO1996019111A1 PCT/EP1995/004828 EP9504828W WO9619111A1 WO 1996019111 A1 WO1996019111 A1 WO 1996019111A1 EP 9504828 W EP9504828 W EP 9504828W WO 9619111 A1 WO9619111 A1 WO 9619111A1
Authority
WO
WIPO (PCT)
Prior art keywords
lauric acid
acid esters
weight
formula
plants
Prior art date
Application number
PCT/EP1995/004828
Other languages
German (de)
English (en)
Inventor
Udo Reckmann
Klaus Stenzel
Stefan Dutzmann
Peter Dahmen
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU43407/96A priority Critical patent/AU4340796A/en
Publication of WO1996019111A1 publication Critical patent/WO1996019111A1/fr

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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof

Definitions

  • the present invention relates to the new use of certain known lauric acid esters to increase the activity of active agrochemicals
  • agrochemical active substances in particular those with a systemic action, must penetrate into the plant so that they can develop their activity uniformly throughout the plant.
  • the uptake into the plant either via the leaves or the root is an imperative
  • the penetration barrier of the cuticle must be overcome by the active ingredients.It is also important that the agrochemical active ingredients penetrate the plant quickly and over as large a surface as possible, otherwise there is a risk that the active components will be washed off by rain
  • additives used in crop protection agents such as surfactants, mineral oils and vegetable oils, require the penetration of agrochemical active ingredients into the plant and can thereby increase the activity of the active ingredients.
  • the additives can increase the wettability, a better distribution of the spray coating on the
  • CH 3 - (CH 2 ) n -COO-R (I) in which R represents 2-ethyl-hexyl or isopropyl can be used very well to increase the activity of agrochemical active substances.
  • the invention therefore relates to the use of lauric acid esters of the formula (I) for the stated purpose.
  • the invention also relates to plant treatment compositions which contain - at least one lauric acid ester of the formula (I), - at least one agrochemical active ingredient and - customary additives.
  • lauric acid esters of the formula (I) which can be used according to the invention have a significantly better activity-increasing influence on active agrochemicals than adipic acid di- (2-ethylhexyl) ester or isopropyl myristate, which is known in constitutional terms
  • lauric acid esters of the formula (I) as an activity improver in formulations of agrochemical active substances has a number of advantages.
  • the lauric acid esters of the formula (I) are substances that are easy to handle and are also available in larger quantities. They can be obtained from renewable raw materials and are biodegradable.
  • the use of lauric acid esters of the formula (I) also means that Effectiveness of agrochemicals increased. This means that the conventional application rates of crop protection agents can be reduced without reducing their effectiveness
  • the lauric acid esters which can be used according to the invention are defined by the formula (I). These are lauric acid (2-ethyl-hexyl) ester and lauric acid isopropyl ester.
  • lauric acid esters of the formula (I) are known (cf. DE-OS 3 841 609, Phytochemistry 2 ⁇ (7), 1788-1791, DE-OS 2 530 334, WO 85-05 066 and JP-OS 63 ⁇
  • agrochemical active substances are understood to mean all substances customary for plant treatment. Fungicides, bactericides, insecticides, acaricides, nematicides, herbicides and plant growth regulators are preferably mentioned.
  • fungicides are:
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
  • Examples include bactericides.
  • Examples include insecticides, acaricides and nematicides.
  • Azocyclotin Bacillus thuringiensis, 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, Brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,
  • Chloethocarb Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanimidamide, Chlo ⁇ yrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton-M, Demeton-S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicenzuro Phonifuros, Dicenzophonos
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenxurophone, Flufenoxurion, Fufonxxuron, Flufenoxuron, Flufenoxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fu
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos,
  • Promecarb Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen,
  • Tebufenozide Tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,
  • herbicides examples include Diflufenican and Propanil; Aryl carboxylic acids, e.g.
  • Dichloropicolinic acid dicamba and picloram
  • Aryloxyalkanoic acids e.g. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr
  • Aryloxy-phenoxyalkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl
  • Azinones e.g. Chloridazon and norflurazon
  • Carbamates e.g.
  • Methabenzthiazuron hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron,
  • Hydroxylamines e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim
  • Imidazolinones e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin
  • Cinosulfuron metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. Hexazinone,
  • Metamitron and metribuzin Others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
  • Chlorcholine chloride and ethephon are examples of plant growth regulators.
  • Suitable additives that can be present in the agents according to the invention are surface-active substances, organic diluents, acids, cold stabilizers, adhesives and dyes
  • Nonionic, anionic, cationic and zwitterionic emulsifiers are suitable as surface-active substances. These substances also include reaction products of fatty acids, fatty acid esters, fatty alcohols, fatty amines, alkylphenols or alkylarylphenols with ethylene oxide and / or propylene oxide, and also their sulfuric acid esters, phosphoric acid monoesters and phosphoric acid di-esters, as well as reaction products of ethylene oxide with propylene oxide Alkyl sulfonates, alkyl sulfates, aryl sulfates, tetra-alkyl ammonium halides, trialkyl aryl ammonium halides and alkylamine sulfonates.
  • the emulsifiers can be used individually or as a mixture. Reaction products of castor oil with ethylene oxide in a molar ratio of 1 20 to 1 60, reaction products of C 6 -C 20 fatty alcohols with ethylene oxide in a molar ratio of 1: 5 to 1:50, reaction products of fatty amines with ethylene oxide in a molar ratio of 1.2 to 1.20, reaction products of 1 mole of phenol with 2 to 3 moles of styrene and 10 to 50 moles of ethylene oxide, reaction products of 1 mole of phenol with 2 to 3 moles of vinyl toluene and 10 to 50 moles of ethylene oxide, reaction products of C 8 -C 12 alkylphenols with ethylene oxide in a molar ratio of 15 to 1 30, alkyl glycosides, C 8 -C 16 alkylbenzene sulfonic acid salts, such as calcium, monoethanolammonium, diethanolammonium and triethanolammonium salts
  • the emulsifiers from the group of alkylaryl polyglycol ethers used in practice are often mixtures of several compounds.
  • these are mixtures of substances which are characterized by the degree of substitution on the phenyl ring connected to the oxyethylene unit and the number of
  • ketones such as methyl isobutyl ketone and cyclohexanone
  • amides such as dimethylformamide
  • cyclic compounds such as N-methyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone, N-octyl-caprolactam, N.
  • Aliphatic and aromatic hydroxycarboxylic acids such as citric acid, salicylic acid, tartaric acid and ascorbic acid are preferred. All substances normally suitable for this purpose can be contained in the agents according to the invention as cold stabilizers. Urea, glycerol and propylene glycol are preferred.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and also synthetic phospholipids are preferred.
  • Other additives can be mineral and vegetable oils.
  • the dyes of the agents according to the invention can include all dyes that can usually be used for plant treatment agents.
  • water can be contained in the plant treatment agents according to the invention.
  • the plant treatment agents according to the invention can be used as spraying agents, spraying agents, pouring agents or pickling agents.
  • the concentrations of lauric acid esters can be varied within a certain range.
  • the concentrations of lauric acid esters of the formula (I) in the formulations are between 1 and 95 percent by weight, preferably between 5 and 70 percent by weight.
  • the concentrations of lauric acid esters of the formula (I) in aqueous systems are generally between 0.001 and 30 percent by weight, preferably between 0.01 and 2 percent by weight, and in oily systems generally between 0.001 and 95 percent by weight, preferably between 0. 1 and 70
  • the ratio of agrochemical active ingredients to lauric acid esters of the formula (I) can also vary within a certain range. In general, the weight ratio between agrochemical active ingredient and lauric acid ester of the formula (I) is between 1: 0.01 and 1: 1000, preferably between 1: 0.05 and 1: 300.
  • agrochemical active ingredients lauric acid esters of the formula (I) and other additives can be varied within a substantial range in the formulations or in the ready-to-use preparations. They are of the order of magnitude as is usually the case in such formulations or preparations.
  • the lauric acid esters of the formula (I) can either be added to the formulations or added to the ready-to-use preparations using the tank mix method.
  • the lauric acid esters of the formula (I) can be used either as such or in the form of solutions in surface-active substances.
  • the formulations and the ready-to-use preparations are prepared by customary methods.
  • Y is the efficiency, expressed in% of the untreated control, when substance B is used in a concentration of n ppm, and
  • E means the efficiency, expressed in% of the untreated control, when using substances A and B in concentrations of m and n ppm, then
  • the combination of the effects is superadditive, which means that there is an effect increasing the effect.
  • the actually observed efficiency must be greater than the value for the expected efficiency (E) calculated from the above formula.
  • Adipic acid di (2-ethylhexyl) ester according to the invention
  • Botrytis test (bean) / protective
  • Plasmopara test (vine) / protective / outdoor spray sequence To prepare the preparations to be tested, a) 1 part by weight of active ingredient with 0.059 part by weight of fatty alcohol (C 10 - C 16 ) -3-glycol ether and 0.041 part by weight of calcium n-dodecyl-benzenesulfonate and butanol are mixed to a 67% solution, b) 1 part by weight of fungicidal active ingredient is mixed with 4.7 parts by weight of acetone and 0.3 part by weight of alkylaryl polyglycol ether, and c) under (a ) and (b) listed mixtures and water combined in the desired proportions
  • a) 1 part by weight of active ingredient with 0.059 part by weight of fatty alcohol (C 10 -C 16 ) -3-glycol ether and 0.041 part by weight of calcium-n-dodecyl-benzenesulfonate and butanol are to a 67% strength Solution mixed
  • the herbicidal activity is visually assessed 14 days after the treatment
  • the plants are covered with spores from Erysiphe graminis f.sp. tritici pollinated.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation.
  • a) 1 part by weight of active ingredient with 0.059 part by weight of fatty alcohol (C 10 -C 16 ) -3-glycol ether and 0.04 1 part by weight of calcium-n-dodecylbenzenesulfonate and butanol form one 67% solution mixed
  • the plants are sprayed with a conidia suspension of Pyrenophora teres.
  • the plants remain in an incubation cabin for 48 hours at 20 ° C. and 100% relative atmospheric humidity
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%
  • a) 1 part by weight of activity promoter with 0.059 parts by weight of fatty alcohol (C 10 -C 16 ) -3-glycol ether and 0.04 1 part by weight of calcium n-dodecylbenzenesulfonate and butanol are added mixed in a 67% solution, b) 1 part by weight of fungicidal active ingredient in the form of a commercially available formulation and c) mixtures and water listed in a) and b) in the desired proportions.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.
  • Evaluation is carried out 7 days after the inoculation.

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  • 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

Des esters d'acide laurique répondant à la formule (I) CH3-(CH2)11-COO-R, dans laquelle R désigne 2-éthylhexyle ou isopropyle, sont très utiles comme renforçateurs de la puissance de principes actifs agrochimiques.
PCT/EP1995/004828 1994-12-20 1995-12-07 Utilisation d'esters d'acide laurique comme renforcateurs de la puissance de principes actifs WO1996019111A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU43407/96A AU4340796A (en) 1994-12-20 1995-12-07 Use of lauric acid esters as potency increasing agents for active substances

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944445546 DE4445546A1 (de) 1994-12-20 1994-12-20 Verwendung von Laurinsäureestern als wirkungssteigernde Stoffe
DEP4445546.1 1994-12-20

Publications (1)

Publication Number Publication Date
WO1996019111A1 true WO1996019111A1 (fr) 1996-06-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/004828 WO1996019111A1 (fr) 1994-12-20 1995-12-07 Utilisation d'esters d'acide laurique comme renforcateurs de la puissance de principes actifs

Country Status (4)

Country Link
AU (1) AU4340796A (fr)
DE (1) DE4445546A1 (fr)
WO (1) WO1996019111A1 (fr)
ZA (1) ZA9510785B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1151667A3 (fr) * 2000-04-28 2003-01-29 Kao Corporation Agent d'activation de plantes
EP1151668A3 (fr) * 2000-04-28 2003-07-02 Kao Corporation Agent d'activation de plantes
EP2258181A3 (fr) * 2004-04-27 2011-05-25 Bayer CropScience AG Utilisation de carboxamides en tant qu'agents favorisant la pénétration
WO2012123904A1 (fr) * 2011-03-17 2012-09-20 Ica Laboratories Cc Composition fongicide
US20170094965A1 (en) * 2014-03-26 2017-04-06 Oleon Nv Use of one or more fatty acid esters as insectidicde and/or arachnicide
EP3771335A1 (fr) 2019-07-31 2021-02-03 Athenion AG Composition répulsive
WO2021064075A1 (fr) * 2019-10-02 2021-04-08 Bayer Aktiengesellschaft Combinaisons de composés actifs comprenant des acides gras
WO2024194047A1 (fr) 2023-03-22 2024-09-26 Mbp 4 Life Sl Procédé d'élicitation pour stimuler une réponse du système immunitaire de plantes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2756464B1 (fr) * 1996-12-02 1998-12-31 Rhone Poulenc Agrochimie Association fongicide a effet synergique a base d'huile d'origine vegetale transformee
US7041624B2 (en) 2001-04-12 2006-05-09 Basf Aktiengesellschaft Bioregulatory combination of active agents

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2341271A1 (fr) * 1976-02-20 1977-09-16 Airwick Ag Procede de potentialisation d'esters phosphoriques insecticides et nouvelles compositions insecticides
FR2377154A1 (fr) * 1977-01-17 1978-08-11 Block Drug Co Insecticide contre les poux
DE3247050A1 (de) * 1982-12-20 1984-06-20 Bayer Ag, 5090 Leverkusen Herbizide mittel
EP0128351A1 (fr) * 1983-05-17 1984-12-19 Bayer Ag Agent pesticide
GB2243297A (en) * 1990-04-24 1991-10-30 Sumitomo Chemical Co Insecticidal compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2341271A1 (fr) * 1976-02-20 1977-09-16 Airwick Ag Procede de potentialisation d'esters phosphoriques insecticides et nouvelles compositions insecticides
FR2377154A1 (fr) * 1977-01-17 1978-08-11 Block Drug Co Insecticide contre les poux
DE3247050A1 (de) * 1982-12-20 1984-06-20 Bayer Ag, 5090 Leverkusen Herbizide mittel
EP0128351A1 (fr) * 1983-05-17 1984-12-19 Bayer Ag Agent pesticide
GB2243297A (en) * 1990-04-24 1991-10-30 Sumitomo Chemical Co Insecticidal compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1151667A3 (fr) * 2000-04-28 2003-01-29 Kao Corporation Agent d'activation de plantes
EP1151668A3 (fr) * 2000-04-28 2003-07-02 Kao Corporation Agent d'activation de plantes
US6849576B2 (en) 2000-04-28 2005-02-01 Kao Corporation Plant-activating agent
US7829500B2 (en) 2000-04-28 2010-11-09 Kao Corporation Plant-activating agent
EP2258181A3 (fr) * 2004-04-27 2011-05-25 Bayer CropScience AG Utilisation de carboxamides en tant qu'agents favorisant la pénétration
WO2012123904A1 (fr) * 2011-03-17 2012-09-20 Ica Laboratories Cc Composition fongicide
US20170094965A1 (en) * 2014-03-26 2017-04-06 Oleon Nv Use of one or more fatty acid esters as insectidicde and/or arachnicide
US10045531B2 (en) * 2014-03-26 2018-08-14 Oleon Nv Use of one or more fatty acid esters as insecticide and/or arachnicide
AU2015238060B2 (en) * 2014-03-26 2018-11-29 Oleon Nv Use of one or more fatty acid esters as insecticide and/or arachnicide
EP3771335A1 (fr) 2019-07-31 2021-02-03 Athenion AG Composition répulsive
EP3771336A1 (fr) 2019-07-31 2021-02-03 Athenion AG Composition répulsive
WO2021064075A1 (fr) * 2019-10-02 2021-04-08 Bayer Aktiengesellschaft Combinaisons de composés actifs comprenant des acides gras
WO2024194047A1 (fr) 2023-03-22 2024-09-26 Mbp 4 Life Sl Procédé d'élicitation pour stimuler une réponse du système immunitaire de plantes

Also Published As

Publication number Publication date
DE4445546A1 (de) 1996-06-27
ZA9510785B (en) 1996-06-20
AU4340796A (en) 1996-07-10

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