EP2117319A2 - Activateur de penetration pour fongicides - Google Patents

Activateur de penetration pour fongicides

Info

Publication number
EP2117319A2
EP2117319A2 EP07856450A EP07856450A EP2117319A2 EP 2117319 A2 EP2117319 A2 EP 2117319A2 EP 07856450 A EP07856450 A EP 07856450A EP 07856450 A EP07856450 A EP 07856450A EP 2117319 A2 EP2117319 A2 EP 2117319A2
Authority
EP
European Patent Office
Prior art keywords
fungicides
tbep
components
harmful organisms
penetration
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Withdrawn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
EP07856450A
Other languages
German (de)
English (en)
Inventor
Peter Baur
Ronald Vermeer
Rainer Süssmann
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 CropScience AG
Original Assignee
Bayer CropScience 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 CropScience AG filed Critical Bayer CropScience AG
Priority to EP07856450A priority Critical patent/EP2117319A2/fr
Publication of EP2117319A2 publication Critical patent/EP2117319A2/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Withdrawn legal-status Critical Current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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N25/02—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 liquids as carriers, diluents or solvents
    • 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
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention relates to the field of chemical crop protection, in particular the use of a special compound as a penetration promoter for agrochemical active substances from the group of fungicides and pesticides containing this compound.
  • the compound is tributoxyethyl phosphate (CAS Regno: 78-51-3, hereinafter referred to as TBEP).
  • Substances which increase the penetration of fungicides through the cuticle of the plant are valuable auxiliaries in chemical crop protection.
  • Various classes of substances are already known as penetration enhancers (see for example WO 2005/104844 A).
  • DE 3513889 A1 generally treats penetration promoters as "activators" for biocides and
  • EP 579052 A2 describes compounds from the group of alkyl phosphates, such as tributyl phosphate and tripropyl phosphate, as penetration promoters. Nevertheless, there is still a need for further compounds with more advantageous properties from a variety of viewpoints.
  • the object of the invention is therefore to provide further advantageous substances with penetration-promoting properties for agrochemical active ingredients. It has now surprisingly been found that the solvent TBEP, in contrast to many other solvents in certain application rates and certain mixing ratios to the active ingredient for increasing the penetration of fungicides through the cuticle of the plant and thus for biological enhancement of pesticides.
  • TBEP is already known as a solvent in correspondingly high application rates in crop protection, as in herbicides (see, for example, WO 01/47356 A1, EP 1251736 B1, WO 00/56146 A1, EP 1164842 B1) and insecticides (see, for example, JP 08291004 A 1 US 5674517 A). From GB 2022070 A TBEP is known for
  • the invention therefore relates to a crop protection agent containing the components
  • TEP Tributoxyethyl phosphate
  • C optionally one or more emulsifiers, preferably from
  • Another object of the invention is the use of the components of the plant protection agent described herein, which is applied to the attacked by the harmful organisms and threatened plants.
  • the invention also provides a method for promoting penetration, wherein the components
  • TEP Tributoxyethyl phosphate
  • C optionally one or more emulsifiers, preferably from
  • the invention likewise relates to the use of the process described here, wherein the components are applied simultaneously or sequentially to the plants attacked and threatened by the harmful organisms.
  • active compounds from the group of fungicides which also include bactericides, as well as plant nutrients which have systemic properties, and contact agents which are suitable as combination partners.
  • fungicides includes both fungicides and bactericides and viricides, unless the context otherwise indicates.
  • systemic active substances ie those taken up by the plant through the leaves or over the roots and passed on in the juice stream, the transport system or plant.
  • active ingredients which have a Log P value of ⁇ 4 (determined according to EEC Directive 79/831 Annex V. A8 by HPLC, Gradient method, acetonitrile / 0.1% aqueous phosphoric acid), in particular those with a Log P value of ⁇ 4 and> 0.1.
  • Examples of individual active compounds from the group of fungicides, which also include bactericides and / or viricides are:
  • Inhibitors of the respiratory chain complex I in particular diflumetorim
  • Respiratory chain complex II particularly boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin,
  • Azoxystrobin Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximethyl, Metominostrobin, Orysastrobin, Pyraclostrobin,
  • Fentin acetate Fentin chloride, fentin hydroxide, silthiofam Inhibitors of amino acid and protein biosynthesis, in particular
  • Inhibitors of signal transduction in particular fenpiclonil, fludioxonil, quinoxyfen
  • Inhibitors of fat and membrane synthesis in particular chlozolinate, iprodione, procymidone, vinclozolin
  • Ampropylfos potassium ampropylfos, edifenphos, lprobenfos (IBP), isoprothiolane,
  • Difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquincx) niesole, flusilazole, flutriafol, furconazole, furconazole-cis,
  • Paclobutrazole penconazole, propiconazole, prothioconazole, simeconazole,
  • Tebuconazole Tetraconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole,
  • the agrochemically active compounds may also be bactericides, for example bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • bactericides for example bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • the fungicides listed above are known, for example, from "The Pesticide Manual”, 12th edition (2000) to 14th edition (2006), The British Crop Protection Council or the references listed for the individual active ingredients.
  • Preferred fungicides are selected from the group of inhibitors of ergosterol biosynthesis, in particular prothioconazole and tebuconazole, and from the group of fungicides with unknown mechanism, in particular fluopicolide.
  • the crop protection agents according to the invention generally contain 0.01 to 99 wt .-%, in particular 0.1 to 95 wt .-%, of the active ingredients from the group of fungicides.
  • Tributoxyethyl phosphate (TBEP) as component (B) has the CAS Regno: 78-51 -3 and is described in detail in this entry in the literature in its other properties.
  • the plant protection agents according to the invention contain 1 to 50% by weight, in particular 5 to 20% by weight, of TBEP (B).
  • the area-related application rates for TBEP (B) are generally between 2.5 and 150 g / ha, preferably 20 to 150? g / ha, more preferably 50 to 150 g / ha, wherein the volume of the spray mixture is usually between 100-1000 L / ha.
  • the content of TBEP (B) for the preparation of an application solution, for example a spray mixture, when using the method according to the invention depends on the desired area-related application amount per hectare (ha) and must therefore be adjusted accordingly in the approach.
  • emulsifiers may be necessary as component (C) in the preparation of the crop protection agent according to the invention and / or the application of the process according to the invention, preferably in the form of spray liquors.
  • Suitable emulsifiers are made the group of ionic and nonionic emulsifiers and their mixtures with HLB values of 10 to 17 (eg emulsifier 1371B). They may be added either directly and / or by the formulation of components (A) and / or (B).
  • auxiliaries and additives which may be present in the preferably liquid formulations according to the invention are all customary formulation auxiliaries, such as organic solvents, defoamers, emulsifiers other than component (C), dispersants, preservatives, acids and Bases, dyes, fillers and even water.
  • Suitable organic solvents are all customary organic solvents which readily dissolve the agrochemical active ingredients used.
  • Aliphatic and aromatic, optionally halogenated hydrocarbons such as toluene, xylene, Solvesso ®, vegetable and mineral oils, such as white spirit, kerosene, alkylbenzenes and spindle oil, furthermore propylene carbonate, carbon tetrachloride, chloroform, methylene chloride and methylene chloride, and also esters, such as ethyl acetate, Lactates of further lactones, such as butyrolactone, as well as lactams, such as N-methylpyrrolidone, N-octylpyrrolidone, N-dodecylpyrrolidone N-octylcaprolactam and N-methylcaprolactam, ⁇ -butyrolactone, dimethylformamide and tributyl phosphate.
  • Suitable defoamers are conventional defoamers present in formulations of agrochemical active compounds. Examples include silicone oils, dispersions of silicone oils, magnesium stearate, phosphinic and phosphonic acids, in particular Fluowet PL 80 ® .
  • Suitable emulsifiers other than component (C) are customary surface-active substances present in formulations of agrochemical active compounds. Examples which may be mentioned are ethoxylated nonylphenols,
  • Suitable dispersants are all substances customarily used in crop protection agents for this purpose.
  • preference is given to natural and synthetic water-soluble polymers such as gelatin, starch and cellulose derivatives, in particular cellulose esters and cellulose ethers, furthermore polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, ligninsulfonates, polymethacrylic acid and co-polymers.
  • Suitable preservatives are all substances usually present in plant treatment compositions for this purpose. Be mentioned as examples Preventol® ® and Proxel ®.
  • Suitable dyes are all customary for the production of pesticides inorganic or organic dyes. Examples include titanium dioxide, carbon black, zinc oxide and blue pigments.
  • Suitable fillers are all substances normally used for this purpose in crop protection agents.
  • inorganic particles such as carbonates, silicates and oxides having an average particle size of 0.005 to 10 .mu.m, more preferably from 0.02 to 2 microns.
  • Silica so-called highly disperse silica, silica gels, as well as natural and synthetic silicates and aluminosilicates.
  • Suitable compounds which act as emulsion stabilizers and / or crystallization inhibitors are all substances conventionally used for this purpose in crop protection agents.
  • the content of the individual components in the crop protection agents according to the invention and the area-related application amount when using the method according to the invention can be varied within a substantial range.
  • all formulations which are suitable for the crop protection agents according to the invention with the components (A) and (B) and optionally the components (C) and / or (D) include all formulations which are applied to plants or their propagation material.
  • the processes used to prepare them are generally known to the person skilled in the art and are described, for example, in Winnacker-Kuchler, "Chemische Technologie” Volume 7, C. Hanser Vertag Kunststoff, 4th ed., 1986, JW van Valkenburg, "Pesticide Formulations", Marcel Dekker NY, 1973, K. Martens, “Spray Drying Handbook", 3rd Ed., 1979, G. Goodwin Ltd., London, or Mollet, Grubenmann, "Formulation Technology", Wiley-VCH-Verlag, Weinheim, 2000.
  • formulation types are those mentioned in the "Manual on development and use of FAO and WHO specifications for pesticides" (FAO and WHO, 2002, appendix E) (each using the GCPF formulation codes with English abbreviation and designation): AL Any other liquid; AP Capsule Suspension; DC Capsule Suspension; DC Capsule Suspension; DC Capsule Suspension; concentrate; DP Dustable powder; DS Powder for dry seed treatment; EC Emulsifiable concentrate; ED Electrochargeable liquid; EC Emulsifiable Granules; EO emulsion, water in oil; EP emulsifiable powder; ES Emulsion for seed treatment; EW emulsion, oil in water; FG fine granule; FS Flowable concentrate for seed treatment; GF Gel for Seed Treatment; GG Macrogranule; GL emulsifiable gel; GP flo-dust; GR Granule; GS Grease;
  • liquid formulation types Preference is given to liquid formulation types. These include the formulation types OD OiI dispersion; DC (dispersible concentrate GCPF formulation code); EC (GCPF Formulation Code for Emulsion Concentrate); EW (GCPF formulation code for oil-in-water emulsion); ES (GCPF Formulation Code for Emulsion Stain); FS (GCPF Formulation Code for Multiphase Concentrate to
  • EO GCPF formulation code for water in oil emulsion
  • ME GCPF Formulation Code for Microemulsion
  • SE GCPF formulation code for suspoemulsion
  • SL GCPF formulation code for water-soluble concentrate
  • CS Capsule Suspension GCPF Formulation Code
  • AL GCPF Formulation Code for ready-to-use liquid formulation, other liquids for undiluted use
  • oil dispersions Syn. Oil dispersion, formulation type OD
  • emulsion concentrates formulation type EC
  • the active ingredient concentration z. B. about 10 to 90 wt .-%; the remainder to 100% by weight consists of TBEP (B) and conventional ones
  • Formulation ingredients (emulsifier, auxiliaries and additives), which applies to all formulations.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • concentration of active ingredient may be about 1 to 50, preferably 3 to 30,% by weight.
  • the invention furthermore relates to a method for controlling harmful organisms, preferably harmful microorganisms, preferably fungi or bacteria, particularly preferably fungi, wherein the crop protection agent according to the invention or the components used in the process according to the invention, preferably in an effective amount, to those affected by the harmful organisms and threatened plants is applied.
  • harmful organisms preferably harmful microorganisms, preferably fungi or bacteria, particularly preferably fungi
  • the crop protection agent according to the invention or the components used in the process according to the invention preferably in an effective amount, to those affected by the harmful organisms and threatened plants is applied.
  • the invention further relates to pesticides according to the invention and to processes comprising at least the components (A) and (B) which, in a preferred embodiment, have superadditive effects (synergism). Due to the improved control of harmful organisms by the plant protection products and methods according to the invention, it is possible to reduce the application rate and / or to increase the safety margin. Both are economically as well as ecologically sensible.
  • the choice of the components (A) and (B) to be used Quantities and the ratio of components (A): (B) depend on a whole series of factors.
  • agrochemical active ingredient is a solid substance, it is generally employed either in finely ground form or in the form of a solution or suspension in an organic solvent or water. If the agrochemical active ingredient is liquid, then the use of an organic is often unnecessary
  • Solvent It is also possible to use a solid agrochemical active ingredient in the form of a melt.
  • the temperatures can be varied within a certain range when carrying out the process. It generally works at temperatures between 0 0 C and 80 0 C, preferably between 10 0 C and 60 ° C.
  • the procedure is generally such that TBEP (B) with one or more of the agrochemical active compounds (A) and optionally with the emulsifier (C) and the auxiliary and
  • Additives (D) mixed.
  • the order in which the components are mixed together depends on the type of formulation.
  • customary devices come into consideration, which are used for the production of agrochemical formulations.
  • the respective surface and / or object-related application rate of the plant protection agents according to the invention of the most varied formulation types and of the method according to the invention for controlling said harmful organisms varies greatly.
  • the application media known to those skilled in the art as customary for the respective field of application are generally used in the customary amounts; for example, from several hundred liters of water per hectare in standard spraying over a few liters of oil per hectare in the "Ultra Low Volume" aircraft application to a few milliliters of a physiological solutions in injection procedures.
  • concentrations of the crop protection agents according to the invention in the corresponding application media therefore vary within a wide range and are dependent on the respective field of use. In general will be
  • Concentrations used which are known to those skilled in the art for the respective field of application. Preference is given to concentrations of from 0.01% by weight to 99% by weight, particularly preferably from 0.1% by weight to 90% by weight.
  • Formulation types as well as the components necessary for carrying out the method according to the invention, can e.g. in the preparation forms customary for liquid preparations, either as such or after prior dilution with water, e.g. as emulsions, suspensions or solutions.
  • the application is carried out by conventional methods, e.g. by spraying, pouring or injecting.
  • the application rate of the crop protection agents of various formulation types according to the invention, as well as the components necessary for carrying out the process according to the invention, can be varied within a substantial range. It depends on the respective fungicides and their content in the formulations.
  • the TBEP (B) to be used is generally applied together with the active substance (A) or directly after one another, preferably in the form of a spray mixture containing TBEP (B) in inventive amounts and the active ingredient (s) in effective amounts and optionally one or more emulsifiers (C).
  • other customary auxiliaries and additives can be added.
  • the spray mixture is preferably prepared based on water and / or an oil, for example a high-boiling hydrocarbon such as kerosene or paraffin.
  • the components for the process according to the invention can be realized either as a tank mixture or via a "ready-to-use formulation" (co-formulation).
  • the plants treated according to the invention are all types of crop plants.
  • the application in economically important, for example, transgenic crops of useful and ornamental plants, e.g. of cereals, such as wheat, barley, rye, oats, millet, rice, cassava and maize, or else cultures of peanut, sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
  • the crop protection agents according to the invention have a number of advantages.
  • the general penetration of the active ingredients into the plant tissue by TBEP is significantly improved.
  • the faster onset of penetration thus also causes a higher rainfastness.
  • the penetration is improved at lower temperatures (for example less than 15 ° C.).
  • TBEP proved to be more tolerable in trials other alkyl ester additives.
  • the use of TBEP thus allows savings on the active ingredients used.
  • TBEP is less harmful to the environment as it has a reduced volatility.
  • the penetration of drugs was measured by enzymatically isolated cuticle of apple tree leaves.
  • the cuticles represent all green parts of plants, such as leaf blade, petiole, stalk, stem, Hypocotyl and many fruits.
  • Sheets were used, which were cut in the fully developed state of apple trees of the variety Golden Delicious. The isolation of the cuticles took place in such a way that
  • the cuticles were placed with tweezers in the middle of the silicone grease-coated edges of the diffusion cells and sealed with a likewise greased ring.
  • the arrangement was chosen so that the morphological outside of the cuticles was directed outwards, ie towards the air, while the original inside side was facing the inside of the diffusion cell.
  • the diffusion cells were filled with water or with a mixture of water and solvent.
  • the TBEP according to the invention leads to an advantageously higher absorption increase of active substances than the penetration promoters of the prior art. This result is surprising and was not expected in view of the prior art.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention se rapporte au domaine de la phytoprotection chimique, en particulier à l'utilisation d'un composé particulier comme activateur de pénétration pour des principes actifs agrochimiques appartenant au groupe des fongicides, ainsi que des agents phytoprotecteurs contenant ce composé. Le composé est du tributoxyéthylphosphate (TBEP).
EP07856450A 2006-12-18 2007-12-07 Activateur de penetration pour fongicides Withdrawn EP2117319A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07856450A EP2117319A2 (fr) 2006-12-18 2007-12-07 Activateur de penetration pour fongicides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06026143A EP1938687A1 (fr) 2006-12-18 2006-12-18 Promoteur de pénétration pour des fongicides
PCT/EP2007/010645 WO2008074408A2 (fr) 2006-12-18 2007-12-07 Activateur de pénétration pour fongicides
EP07856450A EP2117319A2 (fr) 2006-12-18 2007-12-07 Activateur de penetration pour fongicides

Publications (1)

Publication Number Publication Date
EP2117319A2 true EP2117319A2 (fr) 2009-11-18

Family

ID=38052408

Family Applications (2)

Application Number Title Priority Date Filing Date
EP06026143A Withdrawn EP1938687A1 (fr) 2006-12-18 2006-12-18 Promoteur de pénétration pour des fongicides
EP07856450A Withdrawn EP2117319A2 (fr) 2006-12-18 2007-12-07 Activateur de penetration pour fongicides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP06026143A Withdrawn EP1938687A1 (fr) 2006-12-18 2006-12-18 Promoteur de pénétration pour des fongicides

Country Status (6)

Country Link
US (1) US20100048733A1 (fr)
EP (2) EP1938687A1 (fr)
JP (1) JP2010513340A (fr)
KR (1) KR20090100395A (fr)
BR (1) BRPI0720402A2 (fr)
WO (1) WO2008074408A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1938688A1 (fr) * 2006-12-18 2008-07-02 Bayer CropScience AG Promoteur de pénétration pour des insecticides
EP1938689A1 (fr) * 2006-12-18 2008-07-02 Bayer CropScience AG Promoteur de pénétration pour des herbicides
AR114466A1 (es) * 2018-04-04 2020-09-09 Fmc Corp Formulaciones de concentrados emulsionables de fungicidas de sdhi

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2022070A (en) * 1978-04-12 1979-12-12 Sandoz Ltd Defoliation compositions
JPS5724303A (en) * 1980-07-21 1982-02-08 Mitsui Toatsu Chem Inc Insecticidal composition
JPS60224606A (ja) * 1984-04-23 1985-11-09 Kao Corp 農薬組成物
DE4319263A1 (de) * 1992-07-03 1994-01-05 Schoenherr Joerg Pflanzenbehandlungsmittel
US5385604A (en) * 1993-12-20 1995-01-31 Huntington Laboratories, Inc. Germicide resistant floor finish
JPH08291004A (ja) * 1995-04-24 1996-11-05 Nippon Kayaku Co Ltd 害虫防除剤組成物
US5674517A (en) * 1996-04-26 1997-10-07 Henkel Corporation Emulsifier for pesticide concentrates
DE19913036A1 (de) * 1999-03-23 2000-09-28 Aventis Cropscience Gmbh Flüssige Zubereitungen und Tensid/Lösungsmittel-Systeme
DE19963381A1 (de) * 1999-12-28 2001-07-12 Aventis Cropscience Gmbh Tensid/Lösungsmittel-Systeme
DE102004020840A1 (de) * 2004-04-27 2005-11-24 Bayer Cropscience Ag Verwendung von Alkylcarbonsäureamiden als Penetrationsförderer

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008074408A2 *

Also Published As

Publication number Publication date
WO2008074408A3 (fr) 2009-04-09
WO2008074408A2 (fr) 2008-06-26
BRPI0720402A2 (pt) 2014-01-21
KR20090100395A (ko) 2009-09-23
JP2010513340A (ja) 2010-04-30
US20100048733A1 (en) 2010-02-25
EP1938687A1 (fr) 2008-07-02

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