WO2011035873A1 - Pestizidzubereitungen enthaltend derivate von pyrrolidon-4-carbonsäure - Google Patents
Pestizidzubereitungen enthaltend derivate von pyrrolidon-4-carbonsäure Download PDFInfo
- Publication number
- WO2011035873A1 WO2011035873A1 PCT/EP2010/005737 EP2010005737W WO2011035873A1 WO 2011035873 A1 WO2011035873 A1 WO 2011035873A1 EP 2010005737 W EP2010005737 W EP 2010005737W WO 2011035873 A1 WO2011035873 A1 WO 2011035873A1
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- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- pyrrolidone
- carboxylic acid
- acid derivatives
- alkyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 71
- 239000000575 pesticide Substances 0.000 title claims abstract description 65
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical class OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 title description 10
- -1 N-substituted 2-pyrrolidone-4-carboxylic acid Chemical class 0.000 claims abstract description 66
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- BYCRWNBZOPQYJR-UHFFFAOYSA-N octan-3-yl(octan-3-yloxy)phosphinic acid Chemical compound CCCCCC(CC)OP(O)(=O)C(CC)CCCCC BYCRWNBZOPQYJR-UHFFFAOYSA-N 0.000 description 1
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- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
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- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
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- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229930185156 spinosyn Natural products 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
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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
- 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
- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
Definitions
- the present invention relates to pesticide preparations which
- Pesticides are commonly used in the form of a preparation to achieve better utilization of the active ingredient. Such preparations are also referred to as formulations and are generally present in solid or in liquid form. The formulations contain at least one but mostly several excipients that take on a variety of functions.
- auxiliaries examples include solvents, emulsifiers, and others.
- Humectants are understood to mean auxiliaries which increase the biological effectiveness of the active ingredient without itself having a biological effect, for example by improving wetting, retention or uptake into the plant or the target organism.
- formulation types are aqueous
- SL suspension concentrates
- SE suspo-emulsions
- EC emulsifiable concentrates
- OD oil dispersions
- EW emulsions in water
- ME microemulsions
- formulation types are water-soluble powders or granules (SP, SG) or water-dispersible powders or granules (WP, WDP, WG, WDG).
- SP, SG water-soluble powders or granules
- WP, WDP, WG, WDG water-dispersible powders or granules
- Many effective adjuvants used in pesticide preparations are of concern from a toxicological or ecotoxicological point of view, such as
- Nonylphenol ethoxylates due to their endocrine effect, fatty amine ethoxylates (ecotoxic properties) or N-methylpyrrolidone (reprotoxic)
- Pesticidal preparations are those that have no harmful effect on the crop (phytotoxicity). This is especially important for fungicides, insecticides and selective herbicides, but also for non-selective ones
- 2-pyrrolidone-4-carboxylic acids and their salts, esters and amides are useful as active adjuvants for pesticide preparations.
- the present invention therefore relates to pesticide preparations containing
- N-substituted 2-pyrrolidone-4-carboxylic acid derivatives include both the N-substituted 2-pyrrolidone-4-carboxylic acids and also other derivatives, in particular the salts, esters and amides of the N-substituted 2 Pyrrolidone-4-carboxylic acids understood.
- No. 3,224,975 describes lubricant compositions comprising N-alkyl-4-carboxy-2-pyrrolidone in which the alkyl radical comprises 8-25 C atoms.
- GB 1323061 discloses certain N-substituted-4-carboxy-2-pyrrolidones and their use in functional fluids such as
- EP 2 022 781 describes dimeric N-alkyl-4-carboxy-2-pyrrolidone derivatives which are linked via a bridge to the carboxy group and their use as gas hydrate inhibitors.
- EP 2 028 247 describes the use of N-alkyl-2-pyrrolidone-4-carboxylic acid esters as gas hydrate inhibitors.
- WO 2009/086872 and WO 2009/086873 describe the use of N-alkyl-2-pyrrolidone-4-carboxylic acid ammonium salts as corrosion inhibitors.
- pesticides are herbicides, fungicides, insecticides, acaricides, bactericides, molluscides, nematicides and
- physiological reactions such as growth, stinging rhythm, cell division and
- Pesticidal preparations according to the invention are preferably selected from the group consisting of herbicides, insecticides and fungicides.
- Preferred fungicides are aliphatic nitrogen fungicides, amide fungicides such as acylamino acid fungicides or anilide fungicides or benzamide fungicides or strobilurin fungicides, aromatic fungicides, benzimidazole fungicides,
- Benzothiazole fungicides carbamate fungicides, conazole fungicides such as imidazoles or triazoles, dicarboximide fungicides, dithiocarbamate fungicides, imidazole fungicides, morpholide fungicides, oxazole fungicides, pyrazole fungicides, pyridine fungicides,
- Pyrimidine fungicides Pyrole fungicides, quinone fungicides.
- Preferred herbicides are amide herbicides, anilide herbicides, aromatic
- Acid herbicides such as benzoic acid herbicides or picolinic acid herbicides,
- Benzoylcyclohexanedione herbicides benzofuranyl alkyl sulfonate herbicides,
- Cyclohexenoxime herbicides cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides,
- Dithiocarbamate herbicides imidazolinone herbicides, nitrile herbicides,
- Organophosphorus herbicides oxadiazolone herbicides, oxazole herbicides,
- Phenoxy herbicides such as phenoxyacetic acid herbicides or
- Phenoxybutanoic acid herbicides or phenoxypropionic acid herbicides Phenoxybutanoic acid herbicides or phenoxypropionic acid herbicides
- Benzoylpyrazole herbicides or phenylpyrazole herbicides pyridazinone herbicides, pyridine herbicides, thiocarbamate herbicides, triazine herbicides, triazinone herbicides, Triazole herbicides, triazolone herbicides, triazolopyrimidine herbicides, uracil herbicides, urea herbicides such as phenylurea herbicides or sulfonylurea herbicides.
- Preferred insecticides are carbamate insecticides, such as
- Lactone insecticides such as avermectin insecticides or milbemycin insecticides or spinosyn insecticides, nereistoxin analogous insecticides, nicotinoid insecticides such as nitroguanidine nicotinoid insecticides or pyridylmethylamino nicotinoid insecticides, organophosphorus insecticides such as organophosphate insecticides or
- Organothiophosphate insecticides or phosphonate insecticides Organothiophosphate insecticides or phosphonate insecticides
- Phosphoramidothioate insecticides oxadiazine insecticides, pyrazoline insecticides, pyrethroid insecticides such as pyrethroid ester insecticides or pyrethroid ether insecticides or pyrethroid oxime insecticides, tetramic acid insecticides,
- Tetrahydrofurandione insecticides Tetrahydrofurandione insecticides, thiazoline insecticides.
- the one or more pesticides of component a) of the pesticide preparations according to the invention are particularly preferably selected from the group consisting of aryloxyphenoxypropionic acid herbicides,
- Benzoylcyclohexanedione herbicides triazolopyrimidine herbicides, strobilurin fungicides, triazole fungicides, nicotinoid insecticides and pyrethroid insecticides.
- the one or more pesticides of component a) of the pesticide formulations according to the invention are selected from the group consisting of malathion, cypermethrin, glyphosate in the acid form and glyphosate in the form of salts.
- preferred are glyphosate in the acid form and in the form of salts.
- salts of glyphosate glyphosate isopropylammonium is preferred.
- the biological activity of a pesticide can be determined by the plant growth or the damage to the plants by the action of the active ingredient on the leaf as a function of the time of action and the active ingredient concentration.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal preparations according to the invention are preferably the N-substituted, preferably N-alkyl or N-alkenyl-substituted, 2 Pyrrolidone-4-carboxylic acids and their salts, esters and amides.
- R1 Cs to C 30 alkyl or C 8 - to C ß o-alkenyl
- Y is OM, -O- [AO] n is -X or NR2R3,
- M is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted
- Ammonium are in turn selected from alkyl groups having 1 to 4 carbon atoms and CH 2 CH 2 OH,
- n is a number from 0 to 100
- X is C to C 2 o-alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl, the is substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the event that n is not 0, X can also be hydrogen,
- R 2 and R 3 independently of one another are hydrogen, C 1 - to C 2 o-alkyl or
- p is a number from 1 to 20.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal formulations according to the invention are selected from the compounds of the formula (1)
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (2)
- C 8 is - to C 30 -alkyl or C 30 - to C 30 -alkenyl
- C is C 2 to C 20 alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the If n is not 0, then X can also be hydrogen.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (3)
- R 1 is C 8 - to C 30 -alkyl or C 8 - to C 30 -alkenyl
- R2 and R3 are independently hydrogen, C to C 2 o-alkyl or
- p is a number from 1 to 20.
- R1 is preferably a linear or branched alkyl or alkenyl group having 8 to 24 carbon atoms
- R1 particularly preferably represents a linear or branched octyl radical, a cocoyl radical or an oleyl radical.
- M is preferably hydrogen, Na, K, Ca,
- A is preferably ethylene or propylene and particularly preferably ethylene.
- X is preferably hydrogen (when n is not zero), C 4 -C 4 -alkyl and particularly preferably methyl, n is preferably from 1 to 40 and particularly preferably from 5 to 25. If X in the formulas (Z) and ( 2) represents a substituted aryl radical, this is preferably 2,4,6-tri-secondary-butylphenyl or 2,4,6-tristyrylphenyl.
- R 2 and R 3 are preferably hydrogen
- R2 and R3 is methyl or -CH 2 -CH 2 -OH.
- 2-pyrrolidone-4-carboxylic acid derivatives of component b) to vary and thus adapt the physical and physico-chemical properties of the molecules, the N-substituted 2-pyrrolidone-4-carboxylic acid derivatives in the inventive preparations can perform a variety of tasks ,
- N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide preparations according to the invention and in particular the compounds of the formulas (Z) and (1) to (3) are preferably suitable as adjuvants,
- Emulsifiers, dispersants or wetting agents Another object of the present invention is therefore the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as adjuvant,
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as an emulsifier, preferably in a pesticide preparation according to the invention.
- Particularly preferred emulsifiers are compounds of the formula (1) in which M is not hydrogen (anionic emulsifiers) or compounds of the formula (2) in which n is 5 (nonionic emulsifiers).
- Compounds of formula (2) wherein X is other than hydrogen and n is 5 are particularly preferred as emulsifiers for pesticide formulations containing an active ingredient which is sensitive to water or to OH groups, such as sulfonylureas (SUs).
- SUs sulfonylureas
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as a wetting agent, preferably in a pesticide preparation according to the invention.
- Another object of the present invention is the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid Derivatives selected from the formulas (Z) and (1) to (3) as a dispersant, preferably in a pesticide preparation according to the invention.
- SC Suspension concentrates
- SE suspo-emulsions
- EC Concentrates
- OD oil dispersions
- EW emulsions in water
- ME microemulsions
- n ⁇ 9 or compounds of the formula (3) have a low solubility in water and are therefore particularly preferably used as auxiliaries for solvent- or oil-containing preparations such as ECs, EWs, SEs, MEs and ODs.
- solvent- or oil-containing preparations such as ECs, EWs, SEs, MEs and ODs.
- Formulation types selected from water-soluble powders or granules (SP, SG) or water-dispersible powders or granules before (WP, WDP, WG, WDG).
- Compounds of the formulas (Z) and (1) to (3) which are distinguished by a melting point of preferably> 30 ° C. and particularly preferably> 40 ° C., are particularly preferably suitable for use in solid preparations.
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) for the preparation of pesticide preparations according to the invention.
- the preparation of the pesticide formulations according to the invention is possible in various ways and is well known to the person skilled in the art.
- N-substituted 2-pyrrolidone-4-carboxylic acids of component b) of the pesticide formulations according to the invention are obtained by reacting
- Itaconic acid with primary amines can be prepared as described in EP 0 069 512, US 3,224,975 and US 4,127,493.
- N-substituted 2-pyrrolidone-4-carboxylic acids with a base possible.
- Suitable bases are preferably NaOH, Ca (OH) 2 , CaC0 3 , KOH and amines such as
- Ammonia iso-propylamine, mono-, di- or triethanolamine.
- the preparation of the corresponding esters can, for example, by addition of alkylene oxides to the N-substituted 2-pyrrolidone-4-carboxylic acids or by condensation of N-substituted 2-pyrrolidone-4-carboxylic acids with
- polyglycol ethers optionally substituted polyglycol ethers. It may, for example, by the skilled artisan esterifications of N-substituted
- the pesticide preparations of the invention contain one or the a plurality of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b), preferably in amounts of from 0.1 to 50% by weight, more preferably from 0.5 to 30% by weight and especially preferably from 1 to 20 wt .-%. These quantities are based on the entire pesticide preparation according to the invention.
- the pesticidal preparations according to the invention contain the one or more pesticides of component a), preferably in amounts of from 1 to 90% by weight, more preferably from 2 to 80% by weight and especially preferably from 4 to 70% by weight. These quantities are based on the entire pesticide preparation according to the invention.
- the pesticide preparations according to the invention are particularly suitable for controlling and / or controlling weeds, fungal diseases or insect infestation.
- Another object of the present invention is therefore also the use of a pesticide preparation according to the invention for the control and / or control of weeds, fungal diseases or insect infestation.
- the pesticide preparations according to the invention are preferably applied to the fields in the form of spray liquors.
- a spray mixture is prepared by dilution of the concentrate formulation with a defined amount of water.
- the pesticide preparation according to the invention is present as a spray mixture and contains from 0.001 to 10% by weight, preferably from 0.02 to 3% by weight and particularly preferably from 0.025 to
- 2-pyrrolidone-4-carboxylic acid derivatives of component b) to the one or more pesticides of component a) in the spray mixture is preferably from 1: 100 to 10: 1 and more preferably from 1:20 to 4: 1.
- Pesticide amounts are preferably applied in the range of 0.005 to 5 kg per hectare.
- the proportion of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives is in the range of preferably 0.002 to about 2.0 kg / ha.
- the volume of the spray mixture used for the application is preferably in the range from 50 to 1000 l / ha.
- the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives may also be present in the form of a so-called "tank-mix" preparation
- both the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are initially present separately from each other. Both preparations are before
- one or more pesticides are present before mixing as a formulation in water and / or in a solvent or as a solid formulation.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are present before mixing in solution in water or in a solvent or a water-solvent mixture.
- the preparations according to the invention may contain thickeners, solvents, dispersants, emulsifiers, preservatives, adjuvants, binders, thinners, disintegrants, wetting agents, penetrants, cold stabilizers, colorants, defoamers and antioxidants.
- thickening agents all commonly used for this purpose in agrochemical formulations substances such as xanthan gum and / or cellulose, for example carboxy, methyl, ethyl or propyl cellulose or (optionally modified) bentonites in the amounts by weight of 0.01 to 5%, based on the finished agent, are used.
- Suitable solvents are all substances customarily usable for this purpose in agrochemical formulations, such as, for example, aromatic and aliphatic hydrocarbons, N-methylpyrrolidone, cyclohexanone, butyrolactone,
- Acetophenone lactic acid esters such as ethyl hexyllactate, esters of carbonic acid such as propylene carbonate, fatty acid amides such as decanoic acid, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonklare- (ethylhexyl) ester or tris (ethylhexyl) phosphate, glycols, polyethylene glycols, propylene glycol, natural and mineral oils and Esters of fatty acids.
- Suitable dispersants and emulsifiers are all substances customarily usable for this purpose in agrochemical formulations, such as nonionic, amphoteric, cationic and anionic (polymeric) surfactants.
- Preservatives can all usually be used for this purpose
- substances which can be used in agrochemical formulations such as organic acids and their esters, for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1,2-benzisothiazolin-3-one, formaldehyde, Sulfurous acid and its salts are used.
- organic acids and their esters for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1,2-benzisothiazolin-3-one, formaldehyde, Sulfurous acid and its salts are used.
- substances which can be used in agrochemical formulations such as organic acids and their esters, for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates
- alkyl polysaccharides As alcohol ethoxylates, alkyl polysaccharides, fatty amine ethoxylates, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonklare- bis (ethylhexyl) ester or tris (ethylhexyl) phosphate, sorbitan and
- Sorbitolethoxylatderivate and derivatives of alk (en) ylsuccinic be used.
- Suitable penetration enhancers are all substances that are commonly used to prevent the penetration of pesticides into plants or in plants
- Penetration enhancers can be defined, for example, by adding them from the aqueous spray mixture and / or from a spray coating on the plant surface into the cuticle of the plant and thereby increase the tissue mobility (mobility) of active ingredients in the cuticle.
- the method described in the literature can be used to determine this property (Baur et al., 1997, Pesticide Science 51, 131-152).
- Polyvinyl pyrrolidone polyvinyl alcohol, carboxymethyl cellulose, sugar,
- sucrose sorbitol or starch.
- Suitable thinners, absorbers or carriers are all substances customarily usable for this purpose in agrochemical formulations, such as carbon black, tallow, kaolin, aluminum, calcium or magnesium stearate, sodium tripolyphosphate,
- Sodium tetraborate, sodium sulphate, silicates and sodium benzoate As disintegrants, it is possible to use all substances customarily usable for this purpose in agrochemical formulations, such as cellulose, for example carboxymethylcellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulphate or potassium hydrogenphosphate.
- cellulose for example carboxymethylcellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulphate or potassium hydrogenphosphate.
- wetting agents it is possible to use all substances customarily used for this purpose in agrochemical formulations, such as alcohol ethoxylates,
- Alcohol alkoxylates, EO / PO block copolymers (EO: ethylene oxide unit; PO:
- Propylene glycol unit or optionally ethoxylated alkylsulfonic acids.
- cold stabilizers it is possible to use all substances which can usually be used for this purpose in agrochemical formulations.
- Examples include urea, glycerol and propylene glycol. Suitable colorants are all usually in agrochemical for this purpose
- Formulations usable substances such as water or oil-soluble dyes, as well as organic or inorganic pigments.
- Suitable defoamers are all substances customarily usable for this purpose in agrochemical formulations, such as fatty acid alkyl ester alkoxylates; Organopolysiloxanes such
- the preparations according to the invention may additionally contain one or more agrochemical salts, preferably potassium or ammonium salts. Examples:
- phytotoxicity is made on tomato plants (cv.Astona F1), a species known to be sensitive to phytotoxic substances absorbed via the leaf surface ("Phytotoxicity of different classes of adjuvants", H. de Ruiter, et al., Proceedings Fifth International
- Tomato plants (cv. Astona F1) are housed in a greenhouse
- the pots are placed on an underwater watering mat that has been moistened daily with a medium nutrient solution.
- the plants are treated 28 days after seeding at the 4-leaf stage at a size of 15 - 7 cm per plant.
- the content of excipient in the spray solution is 0.5% (v / v or volume%).
- the spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results.
- DAT days after treatment
- the plant mass produced is not reduced when using Compounds 1 and 5 compared to the untreated plant, while the plants treated with the reference substance are weaker, i. H. have a lower plant mass.
- Triethanolamine added to bring the acid into solution.
- glyphosate isopropylammonium with 62% by weight of active ingredient glyphosate IPA salt, IPA: isopropylammonium
- a preparation according to the invention is formed.
- the ratio of glyphosate (based on the acid equivalent) to adjuvant corresponds to that which is also to be found quite thoroughly in commercially available glyphosate formulations.
- the application amount is 135.2 g a.e./ha glyphosate IPA salt (corresponding to 4.0 mmol or 0.68 g a.e./l at a liquid volume of 200 l / ha).
- the abbreviation "a.e.” means "acid equivalent”.
- the spray solutions contain the following concentrations of adjuvant: 0.0141% (v / v).
- Wild oats (Avena Fatua, AVEFA) are exposed to light irradiation in a greenhouse under 14 hours light at a temperature of 18/12 ( ⁇ 0.5) ° C (day / night) and a relative humidity of 70/80 ( ⁇ 5)% (day / Night).
- the light is supplied via high-pressure mercury lamps and fluorescent tubes, so that an output of 70 W / m 2 (PAR, photosynthetically active radiation (400-700 nm)) results at the leaf level.
- the plants are in plastic pots with 11 cm diameter, filled with a mixture of sand and soil (Soil no. 12, Colent bv, Lent, Netherlands) in volume ratio
- the pots are placed on an underwater watering mat, which is moistened daily with a medium nutrient solution. After emergence, the AVEFA sprouts are thinned to six plants per pot for efficacy testing.
- the spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results.
- Wild oat (AVEFA) is treated after reaching the 2-3 leaf stage. Results
- Compound 3 and compound 5 are tested for their suitability as emulsifier in EC emulsions (emulsifiable concentrates).
- pesticide preparations according to the invention are prepared with the active ingredients malathion and cypermethrin (Table 4).
- Table 4 Malathion and cypermethrin EC formulations
- Phenylsulfonate CA (Clariant): calcium dodecylbenzenesulfonate in iso-butanol
- Emuslogen ® 3510 (Clariant): EO / PO block copolymer
- Emuisogen ® EL 360 (Clariant): Castor oil ethoxylate
- 5% aqueous emulsions are prepared in soft (20 ppm) and hard (342 ppm) CIPAC standard water and evaluated at 30 ° C for a period of 2, 4, and 24 hours. All emulsions are stable over this period of time, no phase separation is observed.
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2010297634A AU2010297634A1 (en) | 2009-09-25 | 2010-09-18 | Pesticide preparations containing derivatives of pyrrolidone-4-carboxylic acid |
CN2010800427242A CN102595883A (zh) | 2009-09-25 | 2010-09-18 | 含有吡咯烷酮-4-羧酸衍生物的农药制剂 |
EP10755112A EP2480071A1 (de) | 2009-09-25 | 2010-09-18 | Pestizidzubereitungen enthaltend derivate von pyrrolidon-4-carbonsäure |
US13/497,975 US20120264611A1 (en) | 2009-09-25 | 2010-09-18 | Pesticide Preparations Containing Derivatives Of Pyrrolidone-4-Carboxylic Acid |
BR112012006569A BR112012006569A2 (pt) | 2009-09-25 | 2010-09-18 | preparados pesticidas contendo derivados de ácido pirrolidona-4-carboxílico. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102009043122 | 2009-09-25 | ||
DE102009043122.5 | 2009-09-25 |
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WO2011035873A1 true WO2011035873A1 (de) | 2011-03-31 |
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PCT/EP2010/005737 WO2011035873A1 (de) | 2009-09-25 | 2010-09-18 | Pestizidzubereitungen enthaltend derivate von pyrrolidon-4-carbonsäure |
Country Status (6)
Country | Link |
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US (1) | US20120264611A1 (de) |
EP (1) | EP2480071A1 (de) |
CN (1) | CN102595883A (de) |
AU (1) | AU2010297634A1 (de) |
BR (1) | BR112012006569A2 (de) |
WO (1) | WO2011035873A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010046679A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Ltd. | Pestizidzubereitungen enthaltend N-substituierte 2-Pyrrolidon-4-carbonsäureester |
DE102010046680A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Limited | Verwendung von N-substituierten 2-Pyrrolidon-4-carbonsäureestern als Lösemittel |
DE102012017739A1 (de) | 2012-09-07 | 2014-03-13 | Clariant International Ltd. | Verfahren zur Herstellung von N-substituierten Pyrrolidoncarbonsäureestern |
CN112430156A (zh) * | 2020-12-04 | 2021-03-02 | 中诚国联(河南)生物科技有限公司 | 一种防治刺吸式害虫的高塔药肥颗粒剂制备方法及其应用 |
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2010
- 2010-09-18 WO PCT/EP2010/005737 patent/WO2011035873A1/de active Application Filing
- 2010-09-18 CN CN2010800427242A patent/CN102595883A/zh active Pending
- 2010-09-18 EP EP10755112A patent/EP2480071A1/de not_active Withdrawn
- 2010-09-18 BR BR112012006569A patent/BR112012006569A2/pt not_active IP Right Cessation
- 2010-09-18 US US13/497,975 patent/US20120264611A1/en not_active Abandoned
- 2010-09-18 AU AU2010297634A patent/AU2010297634A1/en not_active Abandoned
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Cited By (4)
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DE102010046679A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Ltd. | Pestizidzubereitungen enthaltend N-substituierte 2-Pyrrolidon-4-carbonsäureester |
DE102010046680A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Limited | Verwendung von N-substituierten 2-Pyrrolidon-4-carbonsäureestern als Lösemittel |
DE102012017739A1 (de) | 2012-09-07 | 2014-03-13 | Clariant International Ltd. | Verfahren zur Herstellung von N-substituierten Pyrrolidoncarbonsäureestern |
CN112430156A (zh) * | 2020-12-04 | 2021-03-02 | 中诚国联(河南)生物科技有限公司 | 一种防治刺吸式害虫的高塔药肥颗粒剂制备方法及其应用 |
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US20120264611A1 (en) | 2012-10-18 |
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CN102595883A (zh) | 2012-07-18 |
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