CA2265548C - Fungicidal mixture, its use and agents containing the same - Google Patents
Fungicidal mixture, its use and agents containing the same Download PDFInfo
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- CA2265548C CA2265548C CA002265548A CA2265548A CA2265548C CA 2265548 C CA2265548 C CA 2265548C CA 002265548 A CA002265548 A CA 002265548A CA 2265548 A CA2265548 A CA 2265548A CA 2265548 C CA2265548 C CA 2265548C
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- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
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- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
- C05D9/00—Other inorganic fertilisers
- C05D9/02—Other inorganic fertilisers containing trace elements
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- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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Abstract
A mixture is composed of a preparation of the plant Reynoutria sachalinensis and of a nitrogen fertiliser with 1 to 10 wt.% plant available magnesium and 0.001 to 5 wt.% of one or more of the elements boron, copper, iron, manganese, molybdenum and zinc.
Description
?102030CA 02265548 l999-03- 15lFUNGICIDAL MIXTURE, ITS USE AND AGENTS CONTAINING THE SAMEThe present invention relates to a mixture, composed essentiallyofa) a ready-toâuse preparation of the plant Reynoutriasachalinensis "andb) a nitrogen fertilizer which comprises from 1 to 10% by weightof plantâavailable magnesium and in each case from 0.001 to5% by weight of one or more of the elements boron, copper,iron, manganese, molybdenum and zinc in water-soluble form,in a synergistically active amount.Moreover, the invention relates to compositions which comprisethis mixture, to a method of preventing infection by phytopatho-genic fungi and for controlling phytopathogenic fungi using com-ponent (a) and component (b), and to the use of component (a) andcomponent (b) for the preparation of such mixtures.The fungicidal action of component (a) is disclosed inEPâA 307 510.Nothing has been known to date about component (b) having anaction against phytopathogenic fungi.It was an object of the present invention to provide mixtureswhich have a synergistically improved activity against phytopa-thogenic fungi combined with a reduced total amount of activeingredients applied with a view to reducing the rates of applica-tion and to improving the spectrum of action of component (a).Accordingly, we have found that this object is achieved by themixture defined at the outset. Moreover, we have found a methodof preventing infection by phytopathogenic fungi and for control-ling phytopathogenic fungi using component (a) and component (b)and the use of component (a) and of component (b)ration of such mixtures.for the prepa-Readyâtoâuse preparations of the plant Reynoutria sachalinensiscan be prepared by a variety of known processes (cf.EP~A 307 510). Liquid formulations, which can be obtained byextracting the plant, are preferred for the mixture according to?1015202530354045CA 02265548 l999-03- l50050/4.73282the invention. Very specially preferred are ethanolic or aqueous/ethanolic extracts.Component (b) can be composed from known chemicals by routineprocesses.The trace elements copper, iron, manganese and zinc are prefer-ably employed in the form of their chlorides, nitrates, sulfatesor carbonates which are readily soluble in water, e.g. copper(II)sulfate, iron(III) sulfate or iron(II) sulfate, manganese carbo-nate and zinc sulfate. The nature of the anions is normally of noimportance.Boron is added mostly in the form of sodium tetraborate, mainlyas boric acid. Molybdenum is normally employed in the form of anammonium molybdate.The preferred quantitative ranges of the trace nutrients in com-ponent (b) are (in % by weight based on solid (b)):Boron: 0.03 to 0.1, mainly 0.05 to 0.08,Copper: 0.3 to 1, mainly 0.5 to 0.8,Iron: 0.03 to 0.1, mainly 0.05 to 0.08,Manganese: 1 to 5, mainly 2 to 4,Molybdenum:0.005 to 0.03, mainly 0.01 to 0.025,Zinc: 0.01 to 0.05, mainly 0.02 to 0.04.The plant-available magnesium, which, in the case of fertilizers,is usually shown converted into waterâsoluble magnesium oxide, isnormally employed in the form of a waterâsoluble magnesium com-pound, preferably as magnesium oxide, magnesium chloride, magne-sium nitrate or magnesium sulfate, or mixtures of these.The magnesium amounts to preferably from 3 to 9, mainly from 4.5to 7.5, % by weight in component (b).Substances which are suitable as nitrogen fertilizers are thosewhich comprise nitrogen in the form of ammonium, nitrate or car-bamide nitrogen, such as ammonia, nitric acid, ammonium chloride,ammonium sulfate, ammonium carbonate, ammonium nitrate, urea andmagnesium nitrate, or mixtures of these.The nitrogen fertilizer normally amounts to from S0 to 98, pre-ferably from 70 to 94 and mainly from 80 to 90% by weight in com-ponent (b).Suitable solid or liquid preparations which comprise the nitrogen?1015202530354045CA 02265548 l999-03- l50050/47328. 3 Afertilizer and the plantâavailable magnesium can also first beprepared separately (following DEâA 31 46 015).Moreover, complexing agents which support the solubility of thestarting materials with metal cations in water and absorption ofthe trace elements through the plantsâ cuticula can also be addedto component (b).Suitable complexing agents are Nâcarboxyalkylamino acids such asnitrilotriacetic acid (H3NTA), hydroxyethylethylenediaminetetra-acetic acid (H3EDTA), cyclohexaneâl,2âdiaminetetraacetic acid(H4CDTA), preferably diethylenetriaminepentaacetic acid (H5DPTA)and mainly ethylenediaminetetraacetic acid (H4EDTA) and saltsthereof, in particular the sodium salts, and mixtures of these.Preferred complexing agents are tetrasodium ethylenediamineâN,N,N',N'âtetraacetate and trisodium N-(2âhydroxyethyl)ethylene-diaminetriacetate, in particular in a mixture, and mainly in aweight ratio of from 4:1 to 2:1. 'The complexing agents normally amount to from 1 to 7, preferablyfrom 2 to 6 and mainly from 3 to 5% by weight in components (b),based on component (b).To prepare component (b), the constituents may be combined in therelevant amounts, and mixed and ground by customary techniquesuntil homogeneous.For safety reasons when using ammonium nitrate and also on ac-count of the improved meterability it can be advantageous firstto take up some or all of the constituents of components (b) inwater and then to combine them to form an aqueous formulation ofcomponent (b), which if desired can be dried to give a storableproduct.With a view to the use of the mixture according to the inventionin liquid form, it is preferred to use such an amount of waterthat the constituents are dissolved completely.Advantageously, the pH of the resulting solutions or suspensionsis brought to a value of from 3.5 to 6. Suitable bases are alkalimetal hydroxides, alkali metal carbonates, alkaline earth metalhydroxides and alkaline earth metal carbonates. Suitable acidsare sulfuric acid, nitric acid and phosphoric acid.Besides, the nitrogen fertilizers and trace element fertilizers,in particular their handling and the preparation of their solu-tions and suspensions, are known to those skilled in the art and.?1015202530354045CA 02265548 1999-03-150050/473284therefore require no further comments (cf., for example, DE-AEPâA 53 246 and EPâA 173 069).Component (a) and component (b) preferably amount to from 93 to100, mainly from 95 to 98, % by weight of the mixtures accordingto the invention.However, the mixtures may also comprise further active ingredi-ents against phytopathogenic fungi or against other pests such asinsects, arachnids or nematodes, or herbicidal or growth-regulating active ingredients or further fertilizers which do notadversely affect the balance of the constituents of component (b)may be admixed with them.The mixtures according to the invention, or the simultaneous,that is, joint or separate, use of the components (a) and (b),are distinguished by an outstanding activity against a broadspectrum of phytopathogenic fungi, in particular from the classesof the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromy-cetes. some of them act systemically and can therefore beemployed as foliar-and soilâacting fungicides.They are especially important for preventing (preventativeaction) and controlling (curative action) a large number of phy-topathogenic fungi in a variety of crop plants such as cotton,vegetable species (eg. cucumbers, beans and cucurbits). barley,grass, oats, coffee, maize, fruit species, rice, rye, soybeans,grapevine, wheat, ornamentals, sugar cane, and a variety ofseeds.They are particularly suitable for controlling the followingphytopathogenic fungi: Erysiphe graminis (powdery mildew) oncereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cu-curbits, Podosphaera leucotricha on apples, Uncinula necator ongrapevines, Puccinia species on cereals, Rhizoctonia species oncotton, rice and lawn, Ustilago species on cereals and sugarcane, Venturia inaequalis (scab) on apples, Helminthosporiumspecies on cereals, Septoria nodorum on wheat, Botrytis cinerea(gray mold) on strawberries and grapevines, Cercospora arachidi-cola on peanuts, Pseudocercosporella herpotrichoides on wheat andbarley, Pyricularia oryzae on rice, Phytophthora infestans onpotatoes and tomatoes, Plasmopara viticola on grapevines, Alter-naria species on vegetables and fruit, and Fusarium and Verticil-lium species.Furthermore, they can be used in the protection of materials (eg.in the protection of wood), for example against Paecilomyces?1015202530354045CA 02265548 1999-03-150050/4.7328variotii.The components (a) and (b) can be applied simultaneously, thatis, jointly or separately, or in succession, the sequence, in thecase of separate application, generally not having any effect onthe result of the prevention and control measures.The components (a) and (b) are normally used in a weight ratio offrom 10:1 to 0.1:l, preferably 5:1 to O.l:l, in particular 5:1 toO.2:1.In the case of agricultural cultivation areas, the applicationrates of the mixtures according to the invention are from 0.5 to80, preferably 1 to 30, and in particular 2 to 15 kg/ha, depend-ing on the nature of the desired effect.In the case of the component (a), the application rates are from0.5 to 60, preferably 1 to 20, and in particular 2 to 10 kg/ha.correspondingly, in the case of component (b), the applicationrates are from 0.2 to 20, preferably 0.5 to 10,1 to 5 kg/ha.and in particularIn seed treatment the mixture application rates are generallyfrom 0.001 to 50 g, preferably from 0.001 to 10 g and,ular, 0.1 to 5 g per kg of seed.in partic-The phytopathogenic fungi are prevented and controlled by theseparate or joint application of components (a) and (b) or of themixtures of components (a) and (b) by spraying or dusting theseeds, the plants or the soils before or after the plants aresown, or before or after plant emergence.In addition to the mixture, the compositions according to theinvention comprise at least one customary formulation auxiliary,such as solid or liquid carriers, surfactants and tackifiers.Liquid carriers are to be understood as meaning liquid solventssuch as water and organic solvents,liary solvent,the latter acting as an auxi-above all when the solvent used is water. Organicsolvents which can be used are: aromatics such as xylene, tolueneand alkylnaphthalenes, chlorinated aromatics or chlorinated ali-phatic hydrocarbons such as chlorobenzenes, chloroethylenes andmethylene chloride, aliphatic hydrocarbons such as cyclohexaneand paraffins, e.g. mineral oil fractions, alcohols such as buta-nol, isobutanol, cyclohexanol and glycol and the correspondingethers and esters, ketones such as acetone, methyl ethyl ketone,?1015202530354045CA 02265548 l999-03- l50050/473286methyl isobutyl ketone and cyclohexanone, aprotic dipolar sol-vents such as dimethylformamide, N-methy1â2-pyrrolidone and dime-thyl sulfoxide.Examples of suitable solid carriers are mineral earths such assilicas, silica gels, silicates, talc, limestone, lime,chalk, bole, loess, clay, dolomite, diatomaceous earth, calciumsulfate, magnesium oxide, ground synthetic materials, andproducts of vegetable origin, such as cereal meal, tree barkmeal, wood meal and nutshell meal, cellulose powders, or othersolid carriers.kaolin,Suitable surfactants are nonionic and anionic emulsifiers/foam-formers and dispersants:â fatty acid polyoxyethylene esters such as lauryl alcoholpolyoxyethylene ether acetate,â alkyl polyoxyethylene ethers or alkyl polyoxypropyleneethers, such as of isotridecyl alcohol, and fatty alcoholpolyoxyethylene ethers,â alkylaryl alcohol polyoxyethylene ethers such as octylphenylpolyoxyethylene ether,â tributylphenol polyoxyethylene ether,â ethoxylated isooctylphenol, octylphenol or nonylphenol orcastor oil,- sorbitol esters,â arylsulfonic acids, alkylsulfonic acids, alkylsulfuric acids,â alkali metal, alkaline earth metal and ammonium salts ofarylsulfonic acids, e.g. lignoâ, phenolâ, naphthalene- anddibutylnaphthalenesulfonic acid, of alkylsulfonic acids, ofalkylarylsulfonic acids, of alkylsulfuric acids, of laurylether sulfuric acids and of fatty alcohol sulfuric acids, offatty acids, of sulfated hexaâ, heptaâ and octadecanols andof fatty alcohol glycol ethers,â condensates of sulfonated naphthalene and its derivativeswith formaldehyde,â condensates of naphthalenesulfonic acids with phenol and for-maldehyde,â protein hydrolysates andâ in particular as dispersants: liqninâsulfite waste liquorsand methylcellulose.?1015202530354045CA 02265548 l999-03- 150050/473287Examples of suitable tackifiers are: carboxymethylcellulose;natural and synthetic polymers in the form of powders, granulesor latices such as gum arabic, polyvinyl alcohol, polyvinylacetate, natural phospholipids such as cephalins and lecithins,synthetic phospholipids.The mixtures according to the invention or the components (a) and(b) can be formulated for example in the form of readyâtoâspraysolutions, powders and suspensions or in the form of highly con-centrated aqueous, oily or other suspensions, dispersions, emul-sions, oil dispersions, pastes, dusts, materials for spreading orgranules, and applied by spraying, atomizing, dusting, spreadingâor pouring. The use form depends on the intended purpose; in anycase, it should guarantee as fine and uniform as possible a dis-tribution of the mixture according to the invention, or of thecomponents (a) and (b).Powders, materials for spreading and dusts can be prepared bymixing or concomitantly grinding components (a) and (b) or themixture of the components (a) and (b) together with a solid car-rier, as defined above.The formulations are prepared in a manner known per se, for exam-ple by adding solvents and/or carriers. Inert additives such asemulsifiers or dispersants are normally admixed with the formula-tions.Granules (eg. coated granules, impregnated granules or homoge-neous granules) are normally prepared by binding the activeingredient, or active ingredients, to a solid carrier as definedabove.In general, the formulations comprise from 0.1 to 95% by weight,preferably 0.5 to 90% by weight, of one of the components (a) and(b), or of the mixture of components (a) and (b).The components (a) and (b), the mixtures or the correspondingformulations are applied by treating the phytopathogenic fungi,their environment, or the plants, seeds or soil to be kept freefrom them, with a fungicidally effective amount of the mixture,or of the components (a) and (b) in the case of separate applica-tion.A preferred method of applying an active ingredient mixture com-prising at least in each case one of these components (a) and (b)is to apply it to the aerial parts of the plant, mainly to thefoliage (foliar application). The number of applications and the?1015202530354045CA 02265548 1999-03-150050/473288application rates depend on the biological and climatic environ-ment of the pathogen. Alternatively, the active ingredients canreach the plant through the soil via the root system (systemicaction), by drenching the site of the plant with a liquid prepa-ration or by incorporating the substances into the soil in solidform, e.g. in the form of granules (soil application).The mixture according to the invention or the components (a) andthe component (b) can also be applied to seed kernels (coating),either by soaking the kernels in succession with a liquid prepa-ration of in each case a component (a) and (b) or by coating themwith the mixture.In addition, other types of application to plants are possible inspecific cases, e.g. the targeted treatment of the buds or thefruiting parts of the plants.Use ExamplesThe following substances were employed:Solution 1 (Component (a)): An extract of Reynoutria sachalinen-sis was prepared by coarsely comminuting 100 g of fresh plantmaterial and extracting it with 750 ml of ethanol for 4 hours inan extraction apparatus. The resulting crude extract was concen-trated on a rotary evaporator to 95 ml and subsequently treatedwith 4 ml of acetone and 1 ml of emulsifier (cf. EEâA 307 S10).Solution 2 (Component (b)):The following were dissolved in 100 g of water:40.0 g of urea,8.5 g of ammonia,2.08 g of nitric acid,5.0 g of magnesium oxide,0.11 g of boric acid,0.8 g of copper sulfate,0.01 g of iron sulfate,2.1 g of manganese carbonate,0.009 g of ammonium molybdate,0.04 g of zinc sulfate,1.0 g of tetrasodium ethy1enediamineâN,N,N',N'âtetraacetate(molecular weight: 380)and?1015202530354045CA 02265548 l999-03- 150050/4732890.31 g of trisodium Nâ(2âhydroxyethyl)ethylenediaminetriacetate(molecular weight: 344).This gave a fertilizer solution which was composed as follows:bybybybybybybybybybybybyofofofofofofofofofofweightweighttotal nitrogen:carbamide nitrogen2 .l .weightweightweightweightweightweightweightweightweightweightammonium nitrogennitrate nitrogenwaterâsoluble magnesium oxidewaterâsoluble boronwaterâsoluble copperwaterâsoluble ironwaterâsolublewaterâsolublewaterâsoluble zinctetrasodium ethylenediamineâN,N,N',N'âtetraacetate andtrisodium N-(2âhydroxyethyl)ethylene-diaminetriacetate-O\'lG\\'lOnO|.\JoL\)O[0manganesemolybdenumP-âOUâ!ofof1-â $ 3 Fâ 3 3 3 ULâ I5 ()3 00 Q. .3 C C 3c\° o\° o\° o\° o\° n\° o\° o\° o\° o\° o\° câ?0.31a\°by weight ofand water as remainder to l00% by weight.In the following experiments, a mixture was used which had beenprepared from suitable amounts of solutions 1 and 2 and water.A mixture of spores of Erysiphe cichoracaerum and Sphaerothecafuliginea was obtained by rinsing cucumber leaves (cultivar: Chi-nese snake cucumber) which were severely infected with these phy-topathogenic fungi with copious quantites of water. Per liter ofwater, in each case 20 cucumber leaves were used, which wereimmersed by hand in each case 10 times while squeezing gently.Cucumbers of cultivar "Chinese snake_cucumber" in the first true-leaf stage were sprayed to runâoff with the aqueous preparationsgiven below in the tables. One day after the preparation of themixture had been applied, the first true leaf of the cucumberswas inoculated with the above-described spore suspension. Incuba-tion and infection of the inoculated plants was carried out in agreenhouse cabinet at 20 to 25°C and a relative atmospheric humid-ity of 50 to 80% for the periods given in the tables. Theinfected leaf area was determined visually relative to the totalleaf area.These visually determined values for the percentage of infectedleaf area were converted into efficacies, as percentages of theuntreated control. An efficacy of 0 means the infection level ofthe treated plants equals that of the untreated control, an effi-?1015202530354045CA 02265548 l999-03- l50050/4732810cacy of 100 means 0% infection. The expected efficacies of thecombinations of the active ingredients were determined usingColby's formula [S. R. Colby, "Calculating synergistic and antag-onistic responses of herbicide combinations", Weeds 15, 20-22(1967)) and compared with the observed efficacies.Colby's formula:E = X + y - X-y/100E expected efficacy. expressed in % of the untreated control,when using the mixture of two active ingredients A and B atconcentrations of a and bx efficacy, expressed in % of the untreated control, when usingactive ingredient A at a concentration of ay efficacy, expressed in % of the untreated control, when usingactive ingredient B at a concentration of bAn efficacy of 0 means that the infection level of the treatedplants corresponds to that of the untreated control plants; anefficacy of 100 means that the treated plants were not infected.It can be seen from the tables which follow that the experimen-tally determined, actual efficiacies of the mixtures of the com-ponents (a) and (b) exceed those previously calculated usingColby's formula.Use Example 1Untreated control: 26% infection of the untreated sample 7 daysafter treatment with the sporesTable 1.1. Efficacy of the individual active ingredientsComponent Active ingredient content Efficacy based on thein the spray mixture untreated control [%][% by weight](@ 15 881 62O5 35(b) 1 3505 23?1015202530354045CA0050/4.732811Table 1.2: Efficacy of the mixture02265548 1999-03-l5Mixture: Content of (a) and Observed ef?cacy Expected ef?cacy [%](b) [% by weight] [%] as per Colby (see above)(a) Cb)1 1 100 750.5 1 100 571 0.5 92 700.5 0.5 88 50Use Example 2Untreated control: 8 0%the sporesTable 2.1â: Efficacy of the individualinfection, 14 days after treatment withactive ingredientsTable 2.2: Efficacy of the mixtureComponent Active lngredient content Ef?cacy based on thein the spray mixture untreated control [%][% by weight](a) 1.5 781 400.5 25(b) 1 100.5 4âxture: Content of (a) and Observed ef?cacy Expected ef?cacy [%](b) [% by weight] [%] as per Colby (see above)(a) (b)1 1 89 460.5 1 86 331 0.5 76 420.5 0.5 64 28Use Example 3Untreated controlafter treatment with the spores: 25% infection of the untreated sample 7 days?0050/47328 CA 02265548 1999-03-1512Table 3.1: Efficacy of the individual active ingredientsComponent Active ingredient content in the Efficacy based on the untreatedspray mixture [% by weight] control [%]5 (a) 1.5 921 720.5 56(b) 1 600.5 5210Table 3.2: Efficacy of the mixtureMixture: Content of (a) and Observed ef?cacy Expected ef?cacy [%]Cb) [% by weight] [%] as per Colby (see above)15(a) (b)1 1 100 890.5 1 100 822 O 1 0.5 96 870.5 0.5 92 79Use Example 425 Untreated control : 80% infection of the untreated sample 14 daysafter treatment with with the sporesTable 4.1: Efficacy of the individual active ingredients30 Component Active ingredient content in the Efficacy based on the untreatedspray mixture [% by weight] control [%](a) 1,5 841 y 44= 0,5 2535 ( ) 1 340,5 25Table 4.2: Efficacy of the mixture: o a an cacy o cacy as perCb) [% by weight] Colby (see above)
Claims (10)
1. A mixture, comprising:
a) an extract of the plant Reynoutria sachalinensis and b) a nitrogen fertilizer which comprises from 1 to 10% by weight of plant-available magnesium and in each case from 0.001 to 5% by weight of one or more of the elements boron, copper, iron, manganese, molybdenum and zinc in water-soluble form, in a weight ratio of component (a) to component (b) from 10:1 to 0.1:1 to control phytopathogenic fungi.
a) an extract of the plant Reynoutria sachalinensis and b) a nitrogen fertilizer which comprises from 1 to 10% by weight of plant-available magnesium and in each case from 0.001 to 5% by weight of one or more of the elements boron, copper, iron, manganese, molybdenum and zinc in water-soluble form, in a weight ratio of component (a) to component (b) from 10:1 to 0.1:1 to control phytopathogenic fungi.
2. A mixture as claimed in claim 1, comprising, in addition, complexing agents selected from the group consisting of N-carboxylalkylamino acids.
3. A mixture as claimed in claim 1 or 2, in which the components (a) and (b) amount to 95 to 98% by weight.
4. A composition for preventing infection by phytopathogenic fungi and for controlling phytopathogenic fungi, comprising the mixture as claimed in claim or 2 and at least one customary formulation auxiliary which is inert to phytopathogenic fungi.
5. A method of preventing infection by phytopathogenic fungi or of controlling phytopathogenic fungi, which comprises treating the fungi, their environment, or the plants, seeds or soils to be kept free from them with component (a) as set forth in claim 1 and component (b) as set forth in claim 1.
6. A method as claimed in claim 6, wherein component (a) as set forth in claim 1 and component (b) as set forth in claim 1 are applied simultaneously or in succession.
7. A method as claimed in claim 6 or 7, wherein component (a) as set forth in claim 1 is applied in an amount of from 0.5 to 60 kg/ha.
8. A method as claimed in any of claims 6 to 8, wherein component (b) as set forth in claim 1 is applied in an amount of from 0.2 to 20 kg/ha.
9. Use of component (a) as set forth in claim 1 for the preparation of a mixture as claimed in claim 1.
10. Use of component (b) as set forth in claim 1 for the preparation of a mixture as claimed in claim 1.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19638021A DE19638021A1 (en) | 1996-09-18 | 1996-09-18 | Fungicidal mixture, its use and agents containing it |
DE19638021.9 | 1996-09-18 | ||
PCT/EP1997/004904 WO1998011782A1 (en) | 1996-09-18 | 1997-09-09 | Fungicidal mixture, its use and agents containing the same |
Publications (2)
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CA2265548A1 CA2265548A1 (en) | 1998-03-26 |
CA2265548C true CA2265548C (en) | 2007-11-27 |
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CA002265548A Expired - Fee Related CA2265548C (en) | 1996-09-18 | 1997-09-09 | Fungicidal mixture, its use and agents containing the same |
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EP (1) | EP0930824B1 (en) |
JP (1) | JP4028600B2 (en) |
AT (1) | ATE221315T1 (en) |
CA (1) | CA2265548C (en) |
DE (2) | DE19638021A1 (en) |
DK (1) | DK0930824T3 (en) |
ES (1) | ES2181027T3 (en) |
PT (1) | PT930824E (en) |
WO (1) | WO1998011782A1 (en) |
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AT4759U1 (en) * | 2000-09-12 | 2001-11-26 | Karner Robert | NITROGEN-FREE FABRIC FOR USE AS FERTILIZER |
AR077432A1 (en) * | 2009-07-30 | 2011-08-24 | Marrone Bio Innovations | INHIBITOR COMBINATIONS OF PLANT PATHOGENS AND METHODS OF USE |
AR080551A1 (en) | 2009-10-05 | 2012-04-18 | Marrone Bio Innovations | DERIVATIVES CONTAINING ANTRAQUINONE AS BIOCHEMICAL AGRICULTURAL PRODUCTS |
PE20140769A1 (en) | 2010-11-04 | 2014-07-13 | Marrone Bio Innovations Inc | COMPOSITIONS CONTAINING ANTHRAQUINONE DERIVATIVES AS GROWTH PROMOTERS AND ANTIFUNGAL AGENTS |
CN103338635A (en) * | 2011-02-02 | 2013-10-02 | 马罗内生物创新公司 | Anthraquinone containing preparations/lignin formulations |
WO2015039983A1 (en) * | 2013-09-20 | 2015-03-26 | Bayer Cropscience Ag | Active compound combinations |
ITBO20130607A1 (en) * | 2013-11-05 | 2015-05-06 | Chemia S P A | FORMULA BIOSTIMULANTE, CORROBORANTE AND CONCANTANTE BASED ON ZEOLITE AND NATURAL VEGETABLE EXTRACTS |
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DE3044903A1 (en) * | 1980-11-28 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING MULTIPLE TRACK NUTRIENT FUELS |
DE3427980A1 (en) * | 1984-07-28 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | MULTIPLE TRACK NUTRIENT |
DE3731239A1 (en) * | 1987-09-17 | 1989-03-30 | Basf Ag | METHOD FOR CONTROLLING MUSHROOMS |
-
1996
- 1996-09-18 DE DE19638021A patent/DE19638021A1/en not_active Withdrawn
-
1997
- 1997-09-09 ES ES97942002T patent/ES2181027T3/en not_active Expired - Lifetime
- 1997-09-09 CA CA002265548A patent/CA2265548C/en not_active Expired - Fee Related
- 1997-09-09 DK DK97942002T patent/DK0930824T3/en active
- 1997-09-09 PT PT97942002T patent/PT930824E/en unknown
- 1997-09-09 JP JP51424598A patent/JP4028600B2/en not_active Expired - Lifetime
- 1997-09-09 WO PCT/EP1997/004904 patent/WO1998011782A1/en active IP Right Grant
- 1997-09-09 DE DE59707878T patent/DE59707878D1/en not_active Expired - Lifetime
- 1997-09-09 AT AT97942002T patent/ATE221315T1/en active
- 1997-09-09 EP EP97942002A patent/EP0930824B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0930824A1 (en) | 1999-07-28 |
JP4028600B2 (en) | 2007-12-26 |
PT930824E (en) | 2002-10-31 |
WO1998011782A1 (en) | 1998-03-26 |
DE59707878D1 (en) | 2002-09-05 |
CA2265548A1 (en) | 1998-03-26 |
ATE221315T1 (en) | 2002-08-15 |
EP0930824B1 (en) | 2002-07-31 |
DK0930824T3 (en) | 2002-09-02 |
JP2001500518A (en) | 2001-01-16 |
ES2181027T3 (en) | 2003-02-16 |
DE19638021A1 (en) | 1998-03-19 |
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