EP2424353A2 - Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiol - Google Patents
Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiolInfo
- Publication number
- EP2424353A2 EP2424353A2 EP10714005A EP10714005A EP2424353A2 EP 2424353 A2 EP2424353 A2 EP 2424353A2 EP 10714005 A EP10714005 A EP 10714005A EP 10714005 A EP10714005 A EP 10714005A EP 2424353 A2 EP2424353 A2 EP 2424353A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- weight
- preservative
- composition according
- alkanediol
- 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- Withdrawn
Links
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- 239000003755 preservative agent Substances 0.000 title claims abstract description 51
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- 239000012872 agrochemical composition Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 241000233866 Fungi Species 0.000 claims abstract description 9
- 241000238631 Hexapoda Species 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
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- 201000002266 mite infestation Diseases 0.000 claims abstract description 7
- 230000001105 regulatory effect Effects 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 10
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims description 9
- 230000001276 controlling effect Effects 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
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- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 229960005323 phenoxyethanol Drugs 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 3
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 3
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- PETXWIMJICIQTQ-UHFFFAOYSA-N phenylmethoxymethanol Chemical compound OCOCC1=CC=CC=C1 PETXWIMJICIQTQ-UHFFFAOYSA-N 0.000 claims description 3
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- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 claims description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 2
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- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 2
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- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 19
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- KANAPVJGZDNSCZ-UHFFFAOYSA-N 1,2-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)N=CC2=C1 KANAPVJGZDNSCZ-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 3
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- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Definitions
- the present invention is an agrochemical composition containing pesticide, preservative and unbranched 1, 2-alkanediol having 5 to 10 carbon atoms. Furthermore, the invention relates to a process for the preparation of this composition by mixing pesticide, preservative and unbranched 1, 2-alkanediol having 5 to 10 carbon atoms.
- the invention relates to a use of the composition for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, as well as a use of the composition for controlling unwanted insect or M aufbenfall on plants and or to control phytopathogenic fungi and / or to control undesired plant growth, treating crop seeds with the composition, and finally seeds treated with the composition.
- Combinations of preferred features with other preferred features are encompassed by the present invention.
- EP 1 201 125 A1 discloses an endermic ointment composition containing 3-methoxybutanol and 1, 2-pentanediol. Furthermore, it is disclosed that the joint use of these products leads to a superior antiseptic effect.
- EP 1 426 029 A1 discloses an emulsion composition containing 1,2-alkanediol, surfactant, oily substance and water as essential components.
- WO 2003/069994 discloses the use of a mixture of two, three or more unbranched 1, 2-alkanediols as antimicrobial agent.
- an antimicrobial agent can be used in an amount, wherein the antimicrobial effect of the alkanediol mixture is synergistically enhanced.
- 1,2-pentanediol has the preservative effect of a mixture of the preservatives phenoxyethanol, methylparaben , Butylparaben, propylparaben and isobutylparaben in cosmetic formulations.
- preservatives in agrochemical compositions has long been known. Without the addition or with too little addition of preservative, there are various problems, mainly due to the growth of microorganisms: formation of gas, so that the plastic cans or metal drums can burst with the agrochemical compositions; Formation of unpleasant odors associated with insecticidal or rodenticidal compositions could cause a repellent effect on insects or rodenticides; discoloration; pH changes to which some pesticides are sensitive; Change in viscosity caused by degradation of polysaccharide-containing thickeners, so that there may be problems in the spray application; or phase separation or sedimentation of emulsions or suspensions by microbial degradation of surfactants, which can lead to problems in the preparation of the tank mix and the application.
- the object of the present invention was therefore to find an agrochemical composition comprising pesticide and preservative which has a reduced concentration of preservative. Another object was that the antimicrobial effect of the preservative in the agrochemical composition is very high even at a reduced concentration. Furthermore, it was an object that the agrochemical composition to be found can continue to formulate problem-free, the usual agrochemical formulation adjuvants can be used, the usual agrochemical application techniques such as spraying or pickling can be used and / or the insecticidal or rodenticidal effect by unwanted odor or Taste is not affected.
- the object has been achieved by an agrochemical composition comprising pesticide, preservative and unbranched 1, 2 alkanediol having 5 to 10 carbon atoms.
- Preferred unbranched 1, 2 alkanediols having 5 to 10 carbon atoms are 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol and 1, 2-decanediol. Particular preference is 1, 2-pentanediol.
- 1, 2-pentanediol is commercially available in various purities, for example, from at least 70 wt.% To at least 99.95 wt.%.
- the composition according to the invention comprises from 0.01 to 10% by weight, preferably from 0.1 to 8% by weight, particularly preferably from 0.5 to 3% by weight, of the alkanediol.
- pesticide denotes at least one active substance selected from the group of fungicides, insecticides, nematicides, herbicides, rodenticides, safeners and / or growth regulators, preferably insecticides, nematicides, herbicides, rodenticides, safeners and / or growth regulation tors.
- the expert understands pesticides usually those agents that are used in agrochemical compositions.
- plant protection products are substances which are intended to: a) protect plants or living parts of plants and plant products from harmful organisms; (b) protect plants or living parts of plants and plant products from animals, plants or micro-organisms which are not harmful organisms; c) to influence the life processes of plants without serving their diet (such as growth regulators); and d) kill plants or inhibit or prevent the growth of plants.
- plant protection products are clearly defined and regulated by law, for example in legislation on the authorization of plant protection products, for the limitation of residues in food or in drinking water, for the protection of bees, for the correct application, for the prohibition of dangerous plant protection products such as DDT or lindane.
- pesticides such as funigzide
- drugs such as antimycotics, antibiotics or disinfectants
- Preferred pesticides are fungicides, insecticides, rodenticides and herbicides, more preferably insecticides, rodenticides and herbicides. Also, mixtures of pesticides of two or more of the above classes may be used. One skilled in the art will be familiar with such pesticides as described, for example, in Pesticide Manual, 14th Ed. (2006), The British Crop Protection Council, London.
- Suitable insecticides are insecticides of the class of carbamates, organophosphates, organochlorine insecticides, phenylpyrazoles, pyrethroids, neonicotinoids, spinosines, avermectins, milbemycins, juvenile hormone analogs, alkylhalides, organotin compounds, nereistoxin analogues, benzoylureas, diacylhydrazines, METI antibodies.
- insecticides such as chloropicrin, pymetrozine, flonicamide, clofentezine, hexythiazox, etoxazole, diafenthiuron, propargite, tetradifon, chlorfenapyr, DNOC, buprofezin, cyromazine, amitraz, hydramethylnone, acequinocyl, fluacrypyrim, rotenone, or their derivatives.
- insecticides such as chloropicrin, pymetrozine, flonicamide, clofentezine, hexythiazox, etoxazole, diafenthiuron, propargite, tetradifon, chlorfenapyr, DNOC, buprofezin, cyromazine, amitraz, hydramethylnone, acequinocyl, fluacrypyrim, rotenone, or their derivatives.
- Suitable fungicides are fungicides of the classes dinitroanilines, allylamines, anilinopyrimidines, antibiotics, aromatic hydrocarbons, benzenesulfonamides, benzimidazoles, benzisothiazoles, benzophenones, benzothiadiazoles, benzotriazines, benzylcarbamates, carbamates, carboxamides, carboxylic acid amides, chloronitriles, cyanoacetamides, cyanoimidazoles, cyclopropanecarboxamides, dicarboximides, di hydroxides, dinitrophenyl crotonates, dithiocarbamates, dithiolanes, ethylphosphonates, ethylaminothiazolecarboxamides, guanidines, hydroxy (2-amino) pyrimidines, hydroxyanilides, imidazoles, imidazolinones, inorganics, isobenzo
- phthalimides piperazines, piperidines, propionamides, pyridazinones, pyridines, pyridinylmethylbenzamides, pyrimidinamines, pyrimidines, pyrimidinone-dehydrazone, pyrroloquinolinones, quinazolinones, quinolines, quinones, sulfamides, sulfamoyltriazoles, thiazole-carboxamides, thiocarbamates, thiophanates, thiophenecarboxamides, toluamides, Triphenyltin compounds, triazines, triazoles.
- Suitable herbicides are herbicides of the classes of acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ethers, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides , Oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamides, phosphorodithioates, phthalamates,
- rodenticides include anticoagulants, inorganic rodenticides, organochlorine rodenticides, organophosphorus rodenticides, pyrimidinamine rodenticides, thiourea rodenticides, urea rodenticides.
- the pesticide contains an insecticide, preferably the pesticide is at least one insecticide.
- the pesticide contains a fungicide, preferably the pesticide consists of at least one fungicide.
- Preferred fungicides are pyraclostrobin, metconazole and epoxiconazole.
- the pesticide comprises a herbicide, preferably the pesticide consists of at least one herbicide.
- the pesticide comprises a rodenticide, preferably an anticoagulant, in particular coumarin derivatives, particularly preferably flocoumafen and difenacoum. Also preferred are mixtures of an anticoagulant with ergocalciferol or vitamin D3.
- the composition according to the invention usually comprises 0.1 to 70% by weight of pesticide, preferably 1 to 50% by weight, in particular 3 to 30% by weight, based on the composition.
- Preservatives are generally those compounds added to agrochemical compositions to increase their shelf life against the action of microorganisms (such as bacteria and fungi), insects and other microorganisms.
- Preferred preservatives have a bactericidal and fungicidal, particularly bactericidal action.
- preservatives examples include benzoic acid, its esters and salts, para-hydroxybenzoic acid (paraben), their esters and salts, propionic acid and its salts, Salicylic acid and its salts, 2,4-hexadienoic acid (sorbic acid) and its salts, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and its salts, 2-zincsulfidopyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanol, dehydroacetic acid, formic acid , 1, 6-bis (4-amidino-2-bromophenoxy) -n-hexane and its salts, 10-undecylenic acid and its salts, 5-amino-1,3-bis (2-ethylhexyl) -5-methyl-hexahydropyrimidine , 5-Bromo-5-nitro-1,3-dioxane, 2-
- octane 3- (4-chlorophenoxy) -1,2-propanediol, hyamine, alkyl (C8-Ci8) -dimethylbenzyl-ammonium chloride, alkyl- (C8-Ci8) -dimethylbenzylammoniumbromide, alkyl- (C8-Ci8) dimethylbenzylammonium saccharinate, benzylhemiformal, 3-iodo-2-propynyl-butylcarbamate, sodium hydroxymethylaminoacetate, cetyltrimethylammonium bromide, cetylpyridinium chloride, and derivatives of 2H-isothiazol-3-one (so-called isothiazolone derivatives), such as alkylisothiazolones (eg 2 Methyl-2H-isothiazol-3-one, MIT; chloro-2-methyl-2H-isothiazol-3-one, CIT),
- Preferred preservatives are propionic acid and its salts, sorbic acid and its salts, benzoic acid, its esters and salts, para-hydroxybenzoic acid and its salts, C 1 -C 4 -alkyl-para-hydroxybenzoate (alkylparabens) and isothiazolone derivatives and mixtures thereof, 2-phenoxyethanol , Cetyltrimethylammonium bromide, cetylpyridinium chloride, benzylhemiformal and dichlorophen. Particularly preferably Ci-C 4 -AIkVl- para-hydroxybenzoate (alkyl parabens) and isothiazolone derivatives, and mixtures thereof, and 2-phenoxyethanol.
- isothiazolone derivatives and mixtures thereof such as alkylisothiazolones (eg MIT, CIT), benzisothiazolones (eg BIT), MTIT, mixtures of MIT and CIT or of MIT and BIT.
- alkylisothiazolones eg MIT, CIT
- benzisothiazolones eg BIT
- MTIT mixtures of MIT and CIT or of MIT and BIT.
- mixtures of isothiazolone derivatives such as mixtures of MIT and CIT or MIT and BIT, especially MIT and BIT.
- Such mixtures are generally in a weight ratio of from 10: 1 to 1:10, preferably from 5: 1 to 1: 5 and especially from 3: 1 to 1: 3.
- concentration of preservative to be used depends on the particular preservative used. Suitable concentrations are therefore mentioned by the manufacturer or in the prior art, for example:
- the concentration of preservative to be used in the composition of the invention therefore also depends on the particular preservative used, but it is usually lower than recommended by the manufacturer of the preservative or in the lower part of the manufacturer's recommendation.
- the skilled artisan can determine a suitable concentration of the preservative in simple preliminary experiments: To test the durability of a composition without the addition of 1, 2-alkanediol, as well as with the addition of alkanediol and reduced concentrations of preservative. Then one selects that reduced concentration of preservative which has the same high durability as the composition without alkanediol.
- the composition according to the invention comprises less than 0.5% by weight, preferably less than 0.1% by weight, more preferably less than 0.05% by weight and in particular less than 0.02% by weight of preservative based on the composition.
- Concentration information for mixtures of preservatives refers to the
- the concentration refers to the pure preservatives.
- the composition according to the invention usually contains formulation auxiliaries, wherein the choice of auxiliaries usually depends on the specific application form or the active ingredient.
- suitable auxiliaries are solvents, solid Carriers, surface-active substances (such as surfactants, solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, antifreeze agents, defoamers, if necessary dyes and adhesives (eg for seed treatment), or bait materials and attractants (eg for baits).
- surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphthalene (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® types, BASF, Germany), and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulf
- Suitable surfactants are, in particular, anionic, cationic, nonionic and amphoteric surfactants, block polymers and polyelectrolytes.
- Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates or carboxylates.
- sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefinsulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of condensed naphthalene, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
- Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
- Examples of phosphates are phosphate esters.
- Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.
- Suitable nonionic surfactants are alkoxylates, N-alkylated fatty acid amides, amine oxides, esters or sugar-based surfactants.
- alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated.
- ethylene oxide and / or propylene oxide can be used, preferably ethylene oxide.
- N-alkylated fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
- esters are fatty acid esters, glycerol esters or monoglycerides.
- sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkyl polyglucosides.
- Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic
- Suitable amphoteric surfactants are alkyl betaines and imidazolines.
- Suitable block polymers are block polymers of A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
- Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid. Examples of polybases are polyvinylamines or polyethylene amines.
- composition of the invention may comprise various amounts of surfactants and surfactants. It can comprise from 0.1 to 40% by weight, preferably from 1 to 30 and in particular from 2 to 20% by weight, of the total amount of surface-active substances and surfactants, based on the total amount of the composition.
- adjuvants examples include organically modified polysiloxanes such as BreakThruS 240 ®; Alcohol alkoxylates such as Atplus ® 245 ® Atplus MBA 1303 ®, Plurafac LF and Lutensol ® ON; EO-PO block polymers, eg. B. Pluronic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. B. Lutensol ® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ® RA.
- organically modified polysiloxanes such as BreakThruS 240 ®
- Alcohol alkoxylates such as Atplus ® 245 ® Atplus MBA 1303 ®, Plurafac LF and Lutensol ® ON
- EO-PO block polymers eg. B. Pluronic RPE 2035 ® and Genapol B ®
- Alcohol ethoxylates e
- thickeners ie, compounds that give the composition a modifiable tes flow behavior, ie high viscosity at rest and low viscosity in motion
- thickeners are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco), Rhodopol ® 23 (Rhodia) or Veegum ® (RT Vanderbilt) or attaclay ® (Engelhard Corp.).
- Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
- defoamers examples include silicone emulsions (such as, for example, silicone ® SRE, Wacker, Germany or Rhodorsil ®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
- colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are those under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, Pigment blue 15: 4, Pigment blue 15: 3, Pigment blue 15: 2, Pigment blue 15: 1, Pigment blue 80 , Pigment yellow 1, Pigment yellow 13, Pigment red 48: 2, Pigment red 48: 1, Pigment red 57: 1, Pigment red 53: 1, Pigment orange 43, Pigment orange 34, Pigment orange 5, Pigment green 36, Pigment green 7, Pigment white 6, Pigment brown 25, Basic violet 10, Basic violet 49, Acid red 51, Acid red 52, Acid red 14, Acid blue 9, Acid yellow 23, Basic red 10, Basic red 108 known dyes and pigments.
- adhesives examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and CEI luloseether (Tylose ®, Shin-Etsu, Japan).
- vegetable or animal food and feed are generally used. Suitable are, for example, cereal, grains, flakes or flours (for example, oats, wheat, barley, corn, soy, rice), coconut flakes u. flour, sugar syrups (obtained, for example, by hydrolysis of starch (glucose syrup), invert sugar syrup, beet sugar syrup, maple syrup), sugars (for example sucrose, lactose, fructose, glucose), nutcracker and the like.
- flour for example hazelnut, walnut, almond
- vegetable fat / oils for example rapeseed oil, soy butter, sunflower oil, cocoa butter, peanut oil, peanut butter, corn oil
- animal fats oil, butter,
- Lard fish oil
- proteins for example skimmed milk powder, egg powder, protein hydrolysates
- minerals for example table salt
- attractants are pheromones, yeast, ground crustaceans, feces, berries, chocolate, fish meal, meat, black pepper and flavor enhancers such as glutamates, especially sodium glutamate and disodium glutamate.
- compositions according to the invention are usually present in compositions customary for agrochemical application: 1.
- Compositions for dilution in water i) Water-soluble concentrates (SL, LS): 10 parts by weight of the active compounds are dissolved with 90 parts by weight of water or a water-soluble solvent , Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a composition with 10 wt .-% active ingredient content.
- Dispersible Concentrates DC: 20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, for.
- B. dissolved polyvinylpyrrolidone dissolved polyvinylpyrrolidone.
- Dilution in water gives a dispersion.
- the active ingredient content is 20% by weight iii) Emulsifiable Concentrates (EC): 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
- Dilution in water results in an emulsion.
- the composition has 15% by weight of active ingredient content, iv) emulsions (EW, EO, ES): 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5
- composition has an active ingredient content of 25 wt .-%.
- Suspensions SC, OD, FS: 20 parts by weight of the active ingredients are mixed with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine
- Water-dispersible and water-soluble powders (WP, SP, SS, WS): 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the composition is 75% by weight.
- Gels (GF): In a ball mill, 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of swelling agent (“gelling agent”) and 70 parts by weight of water or an organic solvent are added Dilution with water results in a stable suspension with 20% by weight of active ingredient content 2.
- compositions for direct application ix) Dusts (DP, DS): 5 parts by weight of the active ingredients are finely ground and mixed with This gives a dust with 5 wt .-% active ingredient, x) granules (GR, FG, GG, MG): 0.5 parts by weight of the active ingredients are finely ground and with Common processes are extrusion, spray-drying or fluidized bed, resulting in a granulate for direct application with 0.5% by weight active ingredient, xi) ULV solutions (UL): 10% by weight. Parts of the active ingredients are in 90 parts by weight of a organic solvents z. B. XyIoI solved. This gives a composition for the direct application with 10 wt .-% active ingredient content.
- liquid compositions such as water-soluble concentrates, emulsions or suspensions, which comprise at least 10% by weight, preferably 20% by weight, particularly preferably at least 40% by weight, of water.
- solid compositions such as baits, granules or gels, which comprise at least 1% by weight, preferably at least 3% by weight, particularly preferably at least 5% by weight of water, are preferred.
- the composition of the invention is usually diluted before use to produce the so-called tank mix.
- mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalene or its derivatives, methanol, Ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration. Preferably, water is used.
- the diluted composition is usually applied by spraying or atomizing.
- wetting agents can be added immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
- the pesticide concentration in the tank mix can be varied in larger areas. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the application rates in the application in crop protection, depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
- the present invention also relates to the use of a composition of the invention for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, wherein the composition of the respective pests, their habitat or the plants to be protected from the respective pest, the soil and / or undesirable plants and / or the crops and / or their habitat. Furthermore, the invention relates to the use of a composition according to the invention for controlling unwanted insect or mite infestation on plants and / or for controlling phytopathogenic fungi and / or for controlling unwanted plant growth, treating crop seeds with the composition.
- the invention relates to seed treated with a composition according to the invention, preferably pickled.
- the skilled person understands by the treatment of seeds the dressing of seeds, wherein the composition remains on the seed.
- the seed particularly preferably contains the composition according to the invention.
- This composition can be applied to the seed undiluted or, preferably, diluted.
- the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of pesticide is present in the compositions to be used for the stain.
- the application can be done before sowing.
- the treatment of plant propagation material in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, Pelleting, dipping or soaking the plant propagating material, wherein the treatment is preferably carried out by pelleting, coating and dusting, so that z. B. premature germination of the seed is prevented.
- pesticide quantities of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of propagating material or seed are generally used.
- the invention further relates to a process for the preparation of a composition according to the invention by mixing pesticide, preservative and unbranched 1, 2-alkanediol having 5 to 10 carbon atoms.
- Preferred pesticides, preservatives and 1,2-alkanediols are as described above.
- the components are blended by methods known to those skilled in the art and commonly used to prepare the desired composition.
- the invention further relates to a use of unbranched 1, 2-alkanediol having 5 to 10 carbon atoms for use in compositions comprising pesticide and preservative.
- the alkanediol is preferably used to increase the bactericidal effect of the preservative.
- the composition additionally contains a formulation aid.
- the pesticide is a herbicide, insecticide or rodenticide, more preferably a herbicide or rodenticide.
- the alkanediol is used in the composition to increase the preservative's preservative effect.
- the alkanediol is used in the composition to enhance the preservative effect of isothiazolone derivatives and mixtures thereof, such as alkylisothiazolones (e.g., MIT, CIT), benzisothiazolones (e.g., BIT), MTIT, mixtures of MIT and CIT, or MIT and BIT.
- alkylisothiazolones e.g., MIT, CIT
- benzisothiazolones e.g., BIT
- MTIT mixtures of MIT and CIT
- MIT and BIT MTIT
- mixtures of MIT and CIT or MIT and BIT
- mixtures of isothiazolone derivatives such as mixtures of MIT and CIT or MIT and BIT, especially MIT and BIT.
- the agrochemical composition has a reduced concentration of preservative; that the antimicrobial effect of the preservative in the agrochemical composition is very high even at a reduced concentration; that the agrochemical composition continues to be easily formulated; that the usual agrochemical formulation adjuvants can be used; that the usual agrochemical application techniques such as spraying or pickling can be used; and that the insecticidal or rodenticidal effect is not impaired by undesirable odor or taste.
- Preservative An aqueous formulation of 2.35-2.65 weight percent 2-methyl-4-isothiazolin-3-one (MIT) and 2.35-2.65 weight percent 1,2-benzisothiazolin-3-one (BIT), commercially available from Thor as Acticide® MBS. The manufacturer recommends using a concentration of 0.2-0.4% by weight in aqueous products.
- MIT 2-methyl-4-isothiazolin-3-one
- BIT 1,2-benzisothiazolin-3-one
- suspension concentrate A 400 g / l pyrimethanil (fungicide)
- SC B Suspension Concentrate B
- F Suspension Concentrate B
- fungicide 150 g / l pyrimethanil
- each of the samples 1 to 16 was inoculated with a germ mixture consisting of various bacterial species (such as Bacillus subtilis, Escherchia coli, Pseudomonas aeruginosa, Staphylococcus aureus), homogenized and incubated at 23 ° C.
- the number of bacteria per gram of sample (cfu / g) was determined immediately and after 24, 48 and 72 hours. In each case, about 1 g of the loaded sample was weighed exactly and spiked out in appropriate dilutions on 2% malt extract agar. The dilution of the loaded sample was carried out by homogenization with sterile water. To detect the bacteria, the malt plates were incubated for 3 days at 23 ° C. The control without preservative and without PDO showed a very high bacterial count of well over 50,000 cfu / g. The results are summarized in Table 1.
- Example 2 The investigation was carried out as in Example 2, wherein instead of suspension concentrate A now suspension concentrate B was used. The results are summarized in Table 2. It has been shown that the addition of 1, 2-pentanediol to the agrochemical formulation, the effect of the preservative could be increased.
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10714005A EP2424353A2 (de) | 2009-04-27 | 2010-04-21 | Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiol |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09158855 | 2009-04-27 | ||
| PCT/EP2010/055241 WO2010124973A2 (de) | 2009-04-27 | 2010-04-21 | Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiol |
| EP10714005A EP2424353A2 (de) | 2009-04-27 | 2010-04-21 | Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2424353A2 true EP2424353A2 (de) | 2012-03-07 |
Family
ID=40941500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP10714005A Withdrawn EP2424353A2 (de) | 2009-04-27 | 2010-04-21 | Zusammensetzung enthaltend pestizid, konservierungmittel und unverzweigtes 1,2-alkandiol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120046167A1 (de) |
| EP (1) | EP2424353A2 (de) |
| JP (1) | JP2012525327A (de) |
| CN (1) | CN102413684B (de) |
| BR (1) | BRPI1007608A2 (de) |
| WO (1) | WO2010124973A2 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013223792A1 (de) * | 2013-11-21 | 2015-05-21 | Henkel Ag & Co. Kgaa | Verwendung kosmetischer Zusammensetzungen für die Inaktivierung und/oder Eliminierung von Hautmilben |
| US10610611B2 (en) * | 2015-07-20 | 2020-04-07 | S. C. Johnson & Son, Inc. | Water-based fragrance composition, fragrance delivery device, and method of providing a long-lasting scent |
| CN105439782B (zh) * | 2015-12-14 | 2019-02-19 | 中国科学院南京土壤研究所 | 癸二醇作为硝化抑制剂的应用 |
| CN107736357A (zh) * | 2017-11-13 | 2018-02-27 | 江苏艾津农化有限责任公司 | 一种农药悬浮剂用防腐组合物及其使用方法 |
| JP2020063363A (ja) * | 2018-10-17 | 2020-04-23 | 三菱鉛筆株式会社 | 筆記具用水性インク組成物 |
| BE1027768B1 (fr) | 2019-11-19 | 2021-06-21 | Minafin Sprl | Compositions agrochimiques à propriétés conservatrices |
| CN112336706A (zh) * | 2020-04-21 | 2021-02-09 | 江苏南京农大动物药业有限公司 | 一种兽用双甲脒溶液增效剂及其制备方法 |
| BE1029367B1 (fr) * | 2021-05-03 | 2022-12-05 | Minagro Srl | Utilisation des 1,2-alcanediols comme adjuvant en agriculture |
| BE1030000B1 (fr) * | 2022-07-11 | 2023-07-03 | Apeo – Agronomical Plant Extracts & Essential Oils | Utilisation d'un compose de la famille des alcanediols comme herbicide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3523121A (en) * | 1967-03-09 | 1970-08-04 | Rohm & Haas | Certain 2-carbamoyl-3-isothiazolenes |
| EP0542721A3 (en) * | 1990-04-27 | 1993-08-25 | Imperial Chemical Industries Plc | Biocide composition and its use |
| JP3657395B2 (ja) * | 1996-05-27 | 2005-06-08 | 株式会社資生堂 | 外用組成物 |
| CA2261362A1 (fr) * | 1998-02-12 | 1999-08-12 | L'oreal | Utilisation du 1,2-pentanediol dans une composition cosmetique ou dermatologique contenant une dispersion aqueuse de particules de polymere filmogene, et composition cosmetique oudermatologique comprenant ces constituants |
| DE69900119T2 (de) * | 1998-02-12 | 2001-10-18 | L'oreal, Paris | Verwendung von 1,2-Pentandiol in kosmetischen oder dermatologischen Zusammensetzungen, die eine wäßrige Dispersion von Partikeln eies filmbildenden Polymers enthalten, und kosmetische und/oder dermatologische Zusammensetzungen, die diese Bestandteile enthalten |
| JP4418976B2 (ja) * | 1998-02-24 | 2010-02-24 | 株式会社マンダム | 防腐殺菌剤及び化粧料組成物 |
| JP5062708B2 (ja) * | 1998-02-24 | 2012-10-31 | 株式会社マンダム | 防腐殺菌剤及び人体施用組成物 |
| US6503904B2 (en) * | 1998-11-16 | 2003-01-07 | Syngenta Crop Protection, Inc. | Pesticidal composition for seed treatment |
| TW592711B (en) | 1999-03-30 | 2004-06-21 | Shiseido Co Ltd | Antiseptic/antifungal agent and endermic liniment composition which contains the same |
| JP3649619B2 (ja) * | 1999-03-30 | 2005-05-18 | 株式会社資生堂 | 外用組成物 |
| GT200100026A (es) * | 2000-02-18 | 2002-02-21 | Composiciones fungicidas tolerantes a inoculos. | |
| JP2003081761A (ja) | 2001-06-27 | 2003-03-19 | Mandom Corp | 乳化組成物 |
| DE10206759A1 (de) | 2002-02-19 | 2003-08-28 | Dragoco Gerberding Co Ag | Synergistische Mischungen von 1,2-Alkandiolen |
| JP2004352688A (ja) * | 2003-05-30 | 2004-12-16 | Kao Corp | 防腐剤組成物 |
| ES2361030T3 (es) * | 2004-07-06 | 2011-06-13 | Basf Se | Composiciones pesticidas líquidas. |
| EP1804580A1 (de) * | 2004-10-22 | 2007-07-11 | Symrise GmbH & Co. KG | Synergistische mischungen aus 1,2-hexanediol und 1,2-octanediol sowie einem weiteren konservierungsmittel |
| US7468384B2 (en) * | 2004-11-16 | 2008-12-23 | Rohm And Haas Company | Microbicidal composition |
| EP1924140A4 (de) * | 2005-07-08 | 2012-06-06 | Isp Investiments Inc | Mikrobizidzusammensetzung |
| EP1906734A1 (de) * | 2005-07-11 | 2008-04-09 | Thor Specialities (UK) Lmited | Mikrobizide zusammensetzung |
| EP1772055A1 (de) * | 2005-10-04 | 2007-04-11 | Rohm and Haas France SAS | Synergistische Mikrobizidzusammensetzungen enthaltend N-Alkyl-1,2-benzoisothiazolin-3-on |
| JP4999321B2 (ja) * | 2005-11-28 | 2012-08-15 | 株式会社マンダム | 防腐殺菌剤を配合した医薬品、及び防腐殺菌方法 |
| UA106213C2 (ru) * | 2008-10-10 | 2014-08-11 | Басф Се | Жидкие препараты для защиты растений, содержащие пираклостробин |
-
2010
- 2010-04-21 EP EP10714005A patent/EP2424353A2/de not_active Withdrawn
- 2010-04-21 JP JP2012506476A patent/JP2012525327A/ja active Pending
- 2010-04-21 US US13/266,262 patent/US20120046167A1/en not_active Abandoned
- 2010-04-21 CN CN201080018511.6A patent/CN102413684B/zh not_active Expired - Fee Related
- 2010-04-21 WO PCT/EP2010/055241 patent/WO2010124973A2/de not_active Ceased
- 2010-04-21 BR BRPI1007608-5A patent/BRPI1007608A2/pt active Search and Examination
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2010124973A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010124973A2 (de) | 2010-11-04 |
| CN102413684B (zh) | 2015-01-21 |
| JP2012525327A (ja) | 2012-10-22 |
| CN102413684A (zh) | 2012-04-11 |
| BRPI1007608A2 (pt) | 2015-09-01 |
| US20120046167A1 (en) | 2012-02-23 |
| WO2010124973A3 (de) | 2011-01-06 |
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