WO2007112905A1 - Penetrationsförderer für insektizide wirkstoffe - Google Patents
Penetrationsförderer für insektizide wirkstoffe Download PDFInfo
- Publication number
- WO2007112905A1 WO2007112905A1 PCT/EP2007/002743 EP2007002743W WO2007112905A1 WO 2007112905 A1 WO2007112905 A1 WO 2007112905A1 EP 2007002743 W EP2007002743 W EP 2007002743W WO 2007112905 A1 WO2007112905 A1 WO 2007112905A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- alkyl
- polyalkylene oxide
- integer
- penetration
- Prior art date
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
- 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
Definitions
- the invention relates to the field of chemical crop protection, in particular the use of special surfactants as penetration promoters for insecticidal active ingredients and insecticidal agents containing these surfactants.
- penetration promoters are valuable auxiliaries in chemical crop protection.
- various classes of substances are already known as penetration enhancers (see, for example, WO 2005/104844), there is a further need for compounds having such properties from a variety of viewpoints.
- the object of the invention is therefore to provide further substances with penetration-promoting properties for insecticidal active ingredients.
- Surfactants from the group of polyalkylene oxide dialkanoates and their use in crop protection are known: in the field of herbicides, for example from WO 01/97614 A, WO 01/97615 A2 and WO 02/49432 A1, the latter two documents surfactants with at least 10 or Use 12 alkylene oxide units; in the field of fungicides from WO 98/48628 A1 as wetting agent; in the field of insecticides from JP 3272105 B2 as wetting agent in an aerosol application.
- Microemulsion concentrates (WO 02/45507 A2), for the preparation of storage-stable solid formulations (JP 11100301 A) 1 for the emulsification of externally applied adjuvants based on oil (WO 94/24858 A1, WO 03/094613 A1). It has now been found that special surfactants from this group are suitable as penetration promoters for insecticidal active ingredients.
- the invention therefore provides the use of polyalkylene oxide derivatives of the formula (I)
- R a is a Cs-Cao-hydrocarbon radical, preferably C 8 -C 3 -alkyl, C 8 -C 3 O- alkenyl or C 8 -C 3 o alkynyl;
- R b is a Cs-Cso-hydrocarbon radical, such as C 8 -C 3 -alkyl, C 8 -C 3 -alkenyl, C 8 - C 30 alkynyl; a is 0 or 1; b is 0 or 1; c is 0 or 1 and
- A is one or more alkylene oxide units.
- Hydrocarbon radical preferably denotes an aliphatic, saturated or presaturated hydrocarbon radical, more preferably alkyl, alkenyl and
- Alkynyl in particular alkyl, having preferably 4 to 24, particularly preferably 8 to 18 C-atoms, which is optionally substituted by halogen, preferably F and Cl, or (CrC 4 ) - alkoxy groups.
- alkylene oxide units is preferably understood as meaning units of C 2 -C 10 -alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or hexylene oxide, it being possible for the units within the surfactant to be identical or different from one another. Particularly preferred are units of ethylene oxide and propylene oxide, most preferably ethylene oxide. If the surfactant (I) contains different alkylene oxide units, these may be arranged alternately, in blocks or randomly.
- the surfactant of the formula (I) preferably contains alkylene oxide units A of the formula
- EO is an ethylene oxide unit
- RO is a unit - CHR x -CHR y -O -, where R x , R y independently of one another are H or (C 1 -C 4 ) alkyl, preferably H, methyl, ethyl, in particular RO is a propylene oxide unit (PO)
- x is an integer from 0 to 600, preferably from 1 to 50
- y is an integer from 0 to 600
- z is an integer from 0 to 600, where the sum (x + y + z)> 2 and ⁇ 600, preferably> 3 and ⁇ 400, more preferably> 5 and ⁇ 100.
- EO and PO in formula (II) mean an ethylene oxide unit and a propylene oxide unit, respectively, also as far as they are used elsewhere in the description.
- surfactants (I) are surfactants of the following formulas 1-1) to
- R a -OAR b wherein R a, A and R b are as defined in formula (I), preferably (C 8 -C 3 o) alkyl-O - [(EO) x (PO) y] - (C 8 -C 3 o) alkyl, 1-2) R a CO-OAR, b wherein R a, A and R b are as defined in formula (I), preferably (C 8 -C 3 o) alkyl-CO-0 - [(EO) ⁇ ( PO) x HC 8 -C 3 O ) AIkVl,
- R a -CO-OA-CO-R b wherein R a, A and R b are as defined in formula (I), preferably (C 8 -C 3 o) alkyl-CO-O - [( EO) x (PO) y ! -CO- (C 8 -C 30 ) alkyl, where x is an integer from 0 to 600, y is an integer from 0 to 600, and x + y is an integer> 1 and ⁇ 600, preferably from 3 to 400, more preferably 5 to 100, most preferably from 5 to 80.
- surfactants are incorporated herein by reference.
- surfactants of formula (I) are also commercially available, for. B. under the brand names
- Particularly preferred polyalkylene oxide derivatives of the formula (I) are those of the formula (III). O
- R is an oleyl, stearyl or lauryl radical
- n is a natural number from 2 to 20
- X is H or -C (O) R.
- Such compounds are for example commercially available from the Cithrol ® series from Croda.
- Preferred compounds of the formula (III) are, for example:
- polyalkylene oxide derivatives of the formula I where the indices a and b are equal to one.
- the commercially available products are generally mixtures of compounds of the formula (I), in particular with different contents of alkylene oxide groups A, so that the value n usually represents an average value.
- surfactants of the formula (I) are listed in Tables 1 to 3 below:
- penetration enhancer is understood to mean compounds which promote the uptake of insecticidal substances through the cuticle of a plant into the plant, i. Accelerate the rate of absorption and / or increase the amount of drug absorbed into the plant.
- insecticides Preferably mentioned are insecticides, acaricides, nematicides, molluscicides, rodenticides and repellents, which have systemic properties, as well as combination partners in question contact agents.
- insecticides includes insecticides as well as acaricides, nematicides, molluscicides, rodenticides and repellents - unless the context otherwise indicates.
- systemic active substances ie those which are taken up by the plant through the leaves or via the roots and passed on in the juice stream, the transport system or plant.
- active substances which have a log P value of ⁇ 4 (determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC 1 gradient method, acetonitrile / 0.1% aqueous phosphoric acid), in particular those with a Log P value of ⁇ 4 and> 0.1.
- Acetylcholinesterase (AChE) inhibitors carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendodi carb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime,
- Oxadiazines for example Indoxacarb Semicarbazone, for example Metaflumizone (BAS3201)
- Chloronicotinyls for example acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam nicotine, bensultap, cartap
- Acetylcholine receptor modulators Spinosyne, for example spinosad GABA-Directed Chloride Channel Antagonists Organochlorines, for example, Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor Fiprole, for example, Acetoprole, Ethiprole, Fipronil, Pyrafluprole, Pyriprole, Vaniliprole
- Chloride channel activators Mectins for example Abamectin, Emamectin, Emamectin benzoate, Ivermectin, Lepimectin, Milbemycin
- Juvenile hormone mimetics for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprene,
- Diacylhydrazines for example chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide
- Inhibitors of chitin biosynthesis Benzoylureas, for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, fiucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron buprofezin cyromazine
- Organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxides
- Pyrroles for example Chlorfenapyr dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC
- METI 1 S for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad hydramethylnone dicofol
- Inhibitors of fatty synthesis tetronic acids for example spirodiclofen, spiromesifen Tetramic acids, for example spirotetramat
- Carboxamides for example flonicamide
- Octopaminergic agonists for example, amitraz
- Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium
- Agonists of the ryanodine receptor benzoic acid dicarboxamides, for example flubendiamide
- Anthranilamides for example DPX E2Y45 (3-bromo-N- ⁇ 4-chloro-2-methyl-6-)
- feed inhibitors for example cryolites, flonicamide, pymetrozine mite growth inhibitors, for example, clofentezine, etoxazole, hexythiazox
- Metoxadiazone Petroleum, Piperonyl butoxide, Potassium oleate, Pyralidyl, Sulfluramid, Tetradifon, Tetrasul, Triarathene.Verbutin.
- the invention further relates to insecticidal compositions containing at least one insecticidal active ingredient (A) and at least one surfactant (B) of the formula (I).
- the insecticidal compositions according to the invention exhibit an excellent action and in a preferred embodiment superadditive effects. Due to the improved control of the harmful organisms by the insecticidal compositions 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 amounts to be used by components (A) + B) and the ratio of components (A): (B) depend on a whole series of factors.
- the formulation types in question include all formulations which are applied to plants or their propagation material.
- the processes used for their preparation are generally known to the person skilled in the art and are described, for example, in Winnacker-Kuchler, "Chemische Technologie” Volume 7, C. Hanser Verlag 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 Any other Powder; CF Capsule Suspension for Seed Treatment; CG Encapsulated Granule; CL Contact liquid or gel; CP contact powder; CS capsule suspension; DC Dispersible 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 Gran
- liquid formulation types Preference is given to liquid formulation types. These include the formulation types DC (GCPF Formulation Code for Dispersible Concentrate); 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 for Seed Treatment); EO (GCPF formulation code for water in oil emulsion); OD (GCPF formulation code for oil dispersions); SE (GCPF formulation code for suspoemulsion); SL (GCPF formulation code for water-soluble concentrate); CS (Capsule Suspension GCPF Formulation Code) and AL (GCPF Formulation Code for ready-to-use liquid formulation, other liquids for undiluted use). Particular preference is given to emulsion concentrates (formulation type EC) and oil dispersions (formulation type OD).
- Suitable 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, dispersants, preservatives, acids and bases, dyes, fillers and also water.
- customary formulation auxiliaries such as organic solvents, defoamers, emulsifiers, dispersants, preservatives, acids and bases, dyes, fillers and also water.
- 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 organic solvents or dispersants are all customary organic solvents.
- Aliphatic and aromatic, optionally halogenated hydrocarbons such as toluene, xylene, Solvesso ®, mineral oils such as white spirit, petroleum, alkylbenzenes and spindle oil, still carbon tetrachloride, chloroform, methylene chloride and methylene chloride, and also esters, such as ethyl acetate, lactates further lactones such as Butyrolactone, also lactams, such as N-methylpyrrolidone, N-octylpyrrolidone, N-dodecylpyrrolidone N-octylcaprolactam and N-methylcaprolactam, ⁇ -butyrolactone, dimethylformamide and tributyl phosphate, triglycerides, such as animal and vegetable fats and oils, and their transesterification products, such as fatty acid alkyl esters
- Active substances existing surface-active substances in question are ethoxylated nonylphenols, polyethylene glycol ethers of linear alcohols, end-capped and non-end-capped alkoxylated linear and branched, saturated and unsaturated alcohols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethylene oxide-propylene oxide block copolymers, polyethylene glycols and polypropylene glycols Fatty acid esters, end-capped and non-endcapped alkoxylated linear and branched, saturated and unsaturated fatty acids, alkyl sulfonates, alkyl sulfates, aryl sulfates, ethoxylated arylalkylphenols, such as tristyrylphenol ethoxylate having an average of 16 ethylene oxide units per molecule, ethoxylated and propoxylated arylalkylphenols and sulfated or phosphated arylalkyl
- Suitable dispersants are all substances customarily used in crop protection agents for this purpose.
- Suitable preservatives are all substances usually present in plant treatment compositions for this purpose. As examples may be mentioned 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. Preference is given to inorganic particles, such as carbonates, silicates and oxides having an average particle size of 0.005 to 5 .mu.m, more preferably from 0.02 to 2 microns. Examples include silicon dioxide, so-called highly disperse silica, silica gels, and 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 can be varied within a substantial range in the formulations according to the invention.
- the preparation of the plant protection agents according to the invention is carried out, for example. in such a way that the components are mixed together in the desired ratios.
- the insecticidal active ingredient is a solid, 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 insecticidal active ingredient is liquid, it is often unnecessary to use an organic solvent. It is also possible to use a solid insecticidal 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 0 C.
- the preparation of agents according to the invention is carried out by mixing the polyalkylene derivatives (I) with one or more active ingredients and optionally with additives.
- the order in which the components are mixed together is arbitrary.
- customary devices are used, which are used for the preparation of insecticidal formulations.
- Pesticides of different types of formulations for controlling the mentioned 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.
- insecticidal formulations according to the invention may 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 insecticidal formulations according to the invention can be varied within a relatively wide range. It depends on the particular insecticidal active ingredients and their content in the formulations.
- the invention further provides a process for promoting the penetration of insecticidal active substances into plants, wherein the insecticidally active substance is applied simultaneously or sequentially applied to the plant with one or more polyalkylene oxide derivatives of formula (I).
- the crop protection agents according to the invention are partly known and partly new.
- the invention also relates to a crop protection agent containing
- Preferred insecticides are those from the group of chloronicotinyls, in particular imidacloprid.
- the insecticidal compositions according to the invention generally contain from 0.01 to 99% by weight, in particular from 0.1 to 95% by weight, of one or more insecticidal active compounds (A).
- the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components and optionally surfactants (B).
- the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
- Dusty 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 .-% of 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.
- the surfactants (B) to be used according to the invention are generally applied together with the insecticidal active ingredient (A) or directly after one another, preferably in the form of a spray mixture containing the surfactants (B) and the insecticidal active compounds (A) in effective amounts and optionally contains other conventional auxiliaries.
- the spray mixture is preferably based on water and / or an oil, for.
- a high-boiling hydrocarbon such as kerosene or paraffin produced.
- the compositions according to the invention can be realized as a tank mixture or via a "finished formulation".
- the weight ratio of insecticidal active ingredients (A) to surfactant (B) can vary within a wide range and depends, for example, on B. on the effectiveness of the insecticidal active ingredient. It is usually in the range of 10: 1 to 1: 5000, preferably 4: 1 to 1: 2000, 4: 1 to 1: 200, 4: 1 to 1:50, 2: 1 to 1: 10, 2 : 1 to 1: 5, 2: 1 to 1: 2.
- Application rates of surfactants (B) are generally between 1 and 5000 g of surfactant / ha, preference is given to 10 and 2000 g of surfactant / ha, in particular 20 to 1000 g of surfactant / ha, 20 to 500 g / ha, 50 to 500 g / ha.
- the concentration of the surfactants (B) to be used according to the invention in a spray mixture is generally from 0.05 to 4% by weight, preferably 0.1 to 1% by weight, in particular 0.1 to 0.3% by weight.
- % Surfactant In the case of harmful animals, application to plants to be protected from these harmful organisms is preferred. Methods for therapeutic use in humans and animals are excluded.
- the invention further relates to a method for controlling harmful animals, preferably harmful arthropods, such as insects and arachnids, helminths and molluscs, particularly preferably harmful arthropods and helminths, wherein
- harmful arthropods such as insects and arachnids, helminths and molluscs, particularly preferably harmful arthropods and helminths, wherein
- the crops treated according to the invention are all 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.
- 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
- Leaf discs were filled by means of vacuum infiltration with a pectinase solution (0.2 to 2%) buffered to a pH between 3 and 4,
- Leaf tops continue to be used. They were washed several times alternately with water and a pH 7 buffer solution. The resulting clean cuticles were finally grown on Teflon flakes and smoothed with a gentle jet of air and dried.
- 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 outer side of the cuticles was directed outwards, ie towards the air, while the original inner side faces the interior of the diffusion cell was.
- the diffusion cells were filled with water or with a mixture of water and solvent.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catching Or Destruction (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/294,921 US20110021575A1 (en) | 2006-03-29 | 2007-03-28 | Penetration enhancers for insecticidal agents |
JP2009501940A JP2009531362A (ja) | 2006-03-29 | 2007-03-28 | 殺虫剤のための浸透増強剤 |
EP07723689A EP2001291A1 (de) | 2006-03-29 | 2007-03-28 | Penetrationsförderer für insektizide wirkstoffe |
BRPI0709632-1A BRPI0709632A2 (pt) | 2006-03-29 | 2007-03-28 | uso de derivados de poli(óxido de alquileno), processo para a promoção da penetração de substáncias ativas inseticidas em plantas, agente de proteção de plantas e processo para o combate de animais nocivos |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06006505A EP1844654A1 (de) | 2006-03-29 | 2006-03-29 | Penetrationsförderer für agrochemische Wirkstoffe |
EP06006505.9 | 2006-03-29 | ||
DE200710013360 DE102007013360A1 (de) | 2007-03-16 | 2007-03-16 | Penetrationsförderer für insektizide Wirkstoffe |
DE102007013360.1 | 2007-03-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007112905A1 true WO2007112905A1 (de) | 2007-10-11 |
Family
ID=38335687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/002743 WO2007112905A1 (de) | 2006-03-29 | 2007-03-28 | Penetrationsförderer für insektizide wirkstoffe |
Country Status (5)
Country | Link |
---|---|
US (1) | US20110021575A1 (de) |
EP (1) | EP2001291A1 (de) |
JP (1) | JP2009531362A (de) |
BR (1) | BRPI0709632A2 (de) |
WO (1) | WO2007112905A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012532161A (ja) * | 2009-07-08 | 2012-12-13 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 農業用組成物 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11100301A (ja) * | 1997-07-30 | 1999-04-13 | Nissan Chem Ind Ltd | 農薬固形組成物 |
JP3272105B2 (ja) * | 1993-05-25 | 2002-04-08 | アース製薬株式会社 | エアゾール殺虫剤及び殺虫方法 |
WO2002045507A2 (en) * | 2000-12-04 | 2002-06-13 | Syngenta Participations Ag | Microemulsifiable agrochemical concentrate |
WO2005084435A2 (de) * | 2004-03-06 | 2005-09-15 | Bayer Cropscience Ag | Suspensionskonzentrate auf ölbasis |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2653026A1 (de) * | 1975-06-30 | 1978-05-24 | Edward C Wenzel | Als kraftstoff fuer verbrennungsmotoren verwendbares fluessigkeitsgemisch |
US5631205A (en) * | 1993-05-05 | 1997-05-20 | Victorian Chemical International Pty. Ltd. | Herbicide, crop desiccant and defolliant adjuvants comprising an unsaturated fatty acid ethyl ester and a non-ionic emulsifier |
JP4053131B2 (ja) * | 1997-04-25 | 2008-02-27 | 石原産業株式会社 | 有害生物防除剤組成物、有害生物の防除方法ならびに有害生物防除効果を増強する方法 |
NZ500548A (en) * | 1997-04-25 | 2002-08-28 | Ishihara Sangyo Kaisha | Biocidal compositions comprising in imidazole derivative, and a synergyst selected form inorganic phosphorus, a fungicide from Phycomycetes and a spreader |
KR20030017549A (ko) * | 2000-06-19 | 2003-03-03 | 바이엘 크롭사이언스 게엠베하 | 제초제 |
DE10029169A1 (de) * | 2000-06-19 | 2002-01-03 | Aventis Cropscience Gmbh | Herbizide Mittel |
US6441003B1 (en) * | 2000-10-04 | 2002-08-27 | Bayer Corporation | Process for the application of systemic pesticides to asexual plant propagules |
DE10063960A1 (de) * | 2000-12-20 | 2002-06-27 | Aventis Cropscience Gmbh | Herbizide Mittel |
AUPS222802A0 (en) * | 2002-05-10 | 2002-06-06 | Victorian Chemicals International Pty Ltd | Adjuvant composition |
DE10223916A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Mikrokapsel-Formulierungen |
WO2005024435A1 (ja) * | 2003-08-27 | 2005-03-17 | Nittec Co., Ltd | 血液自動分析装置 |
DE102004020840A1 (de) * | 2004-04-27 | 2005-11-24 | Bayer Cropscience Ag | Verwendung von Alkylcarbonsäureamiden als Penetrationsförderer |
-
2007
- 2007-03-28 JP JP2009501940A patent/JP2009531362A/ja active Pending
- 2007-03-28 US US12/294,921 patent/US20110021575A1/en not_active Abandoned
- 2007-03-28 BR BRPI0709632-1A patent/BRPI0709632A2/pt not_active IP Right Cessation
- 2007-03-28 EP EP07723689A patent/EP2001291A1/de not_active Withdrawn
- 2007-03-28 WO PCT/EP2007/002743 patent/WO2007112905A1/de active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3272105B2 (ja) * | 1993-05-25 | 2002-04-08 | アース製薬株式会社 | エアゾール殺虫剤及び殺虫方法 |
JPH11100301A (ja) * | 1997-07-30 | 1999-04-13 | Nissan Chem Ind Ltd | 農薬固形組成物 |
WO2002045507A2 (en) * | 2000-12-04 | 2002-06-13 | Syngenta Participations Ag | Microemulsifiable agrochemical concentrate |
WO2005084435A2 (de) * | 2004-03-06 | 2005-09-15 | Bayer Cropscience Ag | Suspensionskonzentrate auf ölbasis |
Non-Patent Citations (4)
Title |
---|
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1999, N. HAYAKAWA ET AL.: "Preservation of solid pesticides", XP002397650, retrieved from STN accession no. 1999:241919 Database accession no. 130:292808 * |
DATABASE WPI Section Ch Week 200227, Derwent World Patents Index; Class A97, AN 1995-048730, XP002397690 * |
RALPH C.KIRKWOOD: "Recent developments in our understanding of the plant cuticle as a barrier to the foliar uptake of pesticides", PESTIC. SCI., vol. 55, 1999, pages 69 - 77, XP002397649 * |
RAMSEY R J L ET AL: "A review of the effects of humidity, humectants, and surfactant composition on the absorption and efficacy of highly water-soluble herbicides", PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, ACADEMIC PRESS, US, vol. 82, no. 2, June 2005 (2005-06-01), pages 162 - 175, XP004888030, ISSN: 0048-3575 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012532161A (ja) * | 2009-07-08 | 2012-12-13 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 農業用組成物 |
Also Published As
Publication number | Publication date |
---|---|
US20110021575A1 (en) | 2011-01-27 |
JP2009531362A (ja) | 2009-09-03 |
EP2001291A1 (de) | 2008-12-17 |
BRPI0709632A2 (pt) | 2011-07-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1926369B1 (de) | Verwendung von laktatestern zur verbesserung der wirkung von pflanzenschutzmitteln | |
EP1937074B1 (de) | Suspensionskonzentrate auf ölbasis | |
EP1742533A1 (de) | Verwendung von alkylcarbonsäureamiden als penetrationsförderer | |
WO2006111279A1 (de) | Suspensionskonzentrate auf ölbasis | |
EP1926380B1 (de) | VERWENDUNG VON CNI-OD-FORMULIERUNGEN ZUR BEKÄMPFUNG DER WEIßEN FLIEGE | |
EP1996015B1 (de) | Köder auf invertzuckersirup basis | |
DE60007165T2 (de) | Pestizide und/oder pflanzenwuchsregulierende zusammensetzungen mit nichtionischer tenside | |
EP1928233A2 (de) | Nikotinyle, pyrethroide und ketoenole als gel- oder schaumformulierung für mehrjährige kulturen | |
EP2117318B1 (de) | Penetrationsförderer für insektizide | |
WO2007112905A1 (de) | Penetrationsförderer für insektizide wirkstoffe | |
DE102007013360A1 (de) | Penetrationsförderer für insektizide Wirkstoffe | |
EP1926373B1 (de) | Verwendung von cni-sl-formulierungen zur bekämpfung der weissen fliege | |
CN101410011A (zh) | 用于杀虫活性物质的渗透促进剂 | |
CN107821451A (zh) | 一种含黄杜鹃提取物与苯菌灵的农药组合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 07723689 Country of ref document: EP Kind code of ref document: A1 |
|
DPE1 | Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2007723689 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 8021/DELNP/2008 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009501940 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200780011464.0 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12294921 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: PI0709632 Country of ref document: BR Kind code of ref document: A2 Effective date: 20080929 |