WO2008135480A2 - Method for controlling specific fungal pathogen in soybeans by employing benodanil - Google Patents

Method for controlling specific fungal pathogen in soybeans by employing benodanil Download PDF

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Publication number
WO2008135480A2
WO2008135480A2 PCT/EP2008/055312 EP2008055312W WO2008135480A2 WO 2008135480 A2 WO2008135480 A2 WO 2008135480A2 EP 2008055312 W EP2008055312 W EP 2008055312W WO 2008135480 A2 WO2008135480 A2 WO 2008135480A2
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WIPO (PCT)
Prior art keywords
benodanil
active compound
cercospora
seed
fungicide
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PCT/EP2008/055312
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French (fr)
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WO2008135480A3 (en
Inventor
Ulrich Schöfl
Michael Vonend
Siegfried Strathmann
Egon Haden
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Basf Se
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Publication of WO2008135480A2 publication Critical patent/WO2008135480A2/en
Publication of WO2008135480A3 publication Critical patent/WO2008135480A3/en

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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides

Definitions

  • the invention relates to a method for controlling Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybeans.
  • benodanil exhibits excellent activity against Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybean crops.
  • the activity is increased considerably by the joint application, in synergistically effective amounts, of benodanil and a second carboxamide fungicide (I) or an azole fungicide (II).
  • Suitable carboxamide fungicides (I) are selected from the group consisting of flutolonil, mepronil, carboxin, fenfuram and furametpyr.
  • Suitable azole fungicides (II) are selected from the group consisting of azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusil- azole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thi
  • Benodanil, the carboxamide and the azole fungicides mentioned above, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); many of them are commercially available. Benodanil and the azole fungicides can be present in various crystal modifications which may differ in their biological activity. Their use also forms part of the subject matter of the present invention.
  • azole fungicide selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam.
  • an azole fungicide selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon,
  • mixtures of benodanil with an azole fungicide (II) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl and carbendazim.
  • an azole fungicide selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadi
  • an azole fungicide selected from the group consisting of epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim, especially an azole fungicide selected from epoxiconazole and metconazole.
  • benodanil and the fungicide I or Il in pure form, to which further compounds active against other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers can be added.
  • mixtures of benodanil and one fungicide I or Il are employed.
  • mixtures of benodanil with two or, if appropriate, more active components may be advantageous.
  • the further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to benodanil.
  • the invention also relates to fungicidal mixtures for controlling Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines, which mixtures comprise, as active components,
  • Benodanil alone or in combination with a fungicide I or II, is preferably suitable for controlling the pathogens Phakopsora pachyrhizi and Phakopsora meibomiae, in particular Phakopsora pachyrhizi, in soybeans.
  • benodanil alone or in combination with a fungicide I or II, is suitable for controlling the pathogens Alternaria spp., Cerco- spora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa and Septoria glycines, in particular Cercospora kikuchi, Cerco- spora sojina, Colletotrichum truncatum, Corynespora cassiicola and Microsphaera diffusa , even more preferred Microsphaera diffusa.
  • Benodanil and the fungicide I or Il can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the harmful fungi are controlled by applying benodanil by treating the seed, by spraying or dusting the plants or the soil before or after sowing of the plants, or before or after emergence of the plants.
  • the fungal pathogens in soybeans are controlled advantageously by applying an aqueous preparation of a formulation comprising benodanil to the above-ground parts of the plants, in particular the leaves, or, as a prophylactic on account of the high systemic effectiveness, by treating the seed or the soil.
  • Benodanil and the fungicide I or Il mentioned above are usually applied in a weight ratio of from 100:1 to 1 :100, preferably from 20:1 to 1 :20, in particular from 10:1 to 1 :10.
  • benodanil can advantageously be applied together with other active compounds, in addition to the abovementioned fungicides I or Il also with herbicides, insecticides, growth regulators or else with fertilizers.
  • Suitable further mixing partners of this nature are in particular: • herbicides such as glyphosate, sulfosate, gluphosinate, tefluthrin, terbufos, chlor- pyrifos, chlorethoxyfos, tebupirimfos, phenoxycarb, diofenolan, pymetrozine, imazethapyr, imazamox, imazapyr, imazapic or dimethenamid-P;
  • insecticides such as fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, car- bosulfan, benfuracarb, dinotefuran, thiacloprid, thiamethoxam, clothianidin, diflubenzuron, flufenoxuron, teflubenzuron and alpha-cypermethrin.
  • Benodanil and the other active compounds mentioned above are usually employed in a weight ratio of from 100:1 to 1 :100, preferably from 20:1 to 1 :20, in particular from 10:1 to 1 :10.
  • mixtures, described above, of benodanil with herbicides are used in particular in a soybean variety, in which the sensitivity of the plants to these herbicides is reduced, for example as a result of breeding, including genetic engineering methods.
  • benodanil When benodanil is used in soybeans, the yields are increased considerably. Thus, benodanil may also be used to increase the yield. By virtue of the yield increase in combination with the excellent action of benodanil against fungal diseases in soybean crops, the method according to the invention is of particular benefit to the farmer. Ex- cellent results can be achieved by using benodanil in combination with at least one second fungicidally active compound I or II.
  • Benodanil or its mixtures with fungicidally, insecticidally and/or herbicidally active compounds is/are applied by treating the fungi or the soybean plants, materials or seeds to be protected against fungal attack or the soil with a fungicidally effective amount of the active compounds.
  • Application can be both before and after the infection of the materials or plants with the fungi.
  • the application rates in the method according to the invention are from 0.01 to 1.5 kg of active compound per ha, depending on the type of effect desired.
  • the amounts of active compound required are generally from 1 to 1500 g of benodanil preferably from 10 to 500 g, per 100 kilograms of seed.
  • the application rates of the mixtures according to the invention are from 10 g/ha to 2500 g/ha, preferably from 50 to 2000 g/ha, in particular from 100 to 1500 g/ha.
  • the application rates for benodanil are correspondingly generally from 1 to 1000 g/ha, preferably from 10 to 750 g/ha, in particular from 20 to 500 g/ha.
  • the application rates for the further fungicidally, insecticidally and/or herbicidally active compound are generally from 1 to 1500 g/ha, preferably from 10 to 1250 g/ha, in particular from 20 to 1000 g/ha.
  • application rates of mixture are generally from 1 to 2000 g/100 kg of seed, preferably from 1 to 1500 g/100 kg, in particular from 5 to 1000 g/100 kg.
  • the compounds can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.
  • the formulations are prepared in a known manner [cf., for example, US 3,060,084, EP-A 707 445 (liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th edition, McGraw- Hill, New York, 1963, pages 8-57, WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961 , Hance et al., Weed Control Handbook, 8th edition, Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001 , 2.
  • Solvents/auxiliaries suitable for this purpose are essentially:
  • aromatic solvents for example Solvesso ® products, xylene
  • paraffins for example mineral oil fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • pyrrolidones N-methylpyrrolidone, N-octylpyrrolidone
  • acetates glycols
  • fatty acid dimethylamides for fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • ground natural minerals for example kaolins, clays, talc, chalk
  • ground synthetic minerals for example finely divided silicic acid, silicates
  • emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
  • Suitable for use as surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributy
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin
  • Suitable antifreeze agents are, for example, glycerol, ethylene glycol and propylene glycol.
  • Suitable antifoams are, for example, silicon stearates or magnesium stearates.
  • a suitable swelling agent is, for example, carrageen (Satiagel ® ).
  • Binders serve to improve the adhesion of the active compound or the active compounds on the seed.
  • Suitable binders are, for example, polyethylene oxide/polypropylene oxide copolymers, polyvinyl alcohol, polyvinylpyrrolidone, poly(meth)acraylate, polybutene, polyisobutylene, polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine (Lupasol ® , Polymin ® ), polyethers, polyure- thanes, polyvinyl acetate and the copolymers of the above polymers.
  • Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth
  • the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s).
  • the active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the formulations can be diluted 2 to 10 times, resulting in ready-to- use preparations comprising from 0.01 to 60% by weight of the active compound(s), preferably from 0.1 to 40% by weight of the active compound(s).
  • active compound(s) 10 parts by weight are dissolved with 90 parts by weight of water or a water-soluble solvent.
  • wetting agents or other auxiliaries are added.
  • the active compound dissolves upon dilution with water. This gives a formula- tion having an active compound content of 10% by weight.
  • active compound(s) 20 parts by weight are dissolved in 70 parts by weight of cyclo- hexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyr- rolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyr- rolidone. Dilution with water gives a dispersion.
  • the active compound content is 20% by weight.
  • active compound(s) 15 parts by weight are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion.
  • the formulation has an active compound content of 15% by weight.
  • Emulsions EW, EO, ES 25 parts by weight of active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.
  • an emulsifying machine e.g. Ultraturrax
  • active compound(s) 20 parts by weight are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
  • the active compound content in the formulation is 20% by weight.
  • Water-dispersible granules and water-soluble granules 50 parts by weight of active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetting agents and made into water-dispersible or water- soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
  • the formulation has an active compound content of 50% by weight.
  • active compound(s) 75 parts by weight of active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
  • the active compound content of the formulation is 75% by weight.
  • active compound(s) 20 parts by weight are, with addition of 10 parts by weight of dispersants, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent, comminuted in a bead mill to give a fine active compound suspension. Dilution with water affords a stabile suspension of the active compound.
  • the formulation has an active compound content of 20 parts by weight.
  • active compound(s) 0.5 part by weight is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules with an active compound content of 0.5% by weight to be applied undiluted.
  • ULV solutions 10 parts by weight of active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product with an active compound content of 10% by weight to be applied undiluted.
  • Suitable for seed treatment are in particular FS formulations.
  • such an FS formulation comprises 1 to 800 g of active compound(s)/l, 1 to 200 g of surfactant/I, 0 to 200 g of antifreeze/I, 0 to 400 g of binder/I, 0 to 200 g of color pigment/I and ad 1 liter of a solvent, preferably water.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring.
  • the use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • a wetting agent e.g., tackifier, dispersant or emulsifier
  • concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, with these concentrates being suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.
  • the active compounds may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active compounds even, if appropriate, not until immediately prior to use (tank mix). These agents are typically admixed with the compositions according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1.
  • Benodanil was employed as a commercial finished formulation and diluted with water to the stated concentration of active compound.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of Colleotrichum truncatum in an aqueous biomalt solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. In this test the sample - treated with 63 ppm of benodanil - showed 69 % efficacy.
  • Example 2 Activity against Septoria glycines
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • a spore suspension of Septoria glycines in an aqueous biomalt solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C.
  • the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.
  • the sample - treated with 63 ppm of benodanil - showed 100 % efficacy.
  • MTP Alter- naria solani
  • a spore suspension of Alter- naria solani in an aqueous biomalt solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C.
  • the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. In this test the sample - treated with 63 ppm of benodanil - showed 79 % efficacy.
  • Example 4 Activity against Cercospora sojina
  • a solution containing 10 mg a.i. per 1 ml dimethyl sulfoxide is prepared.
  • the stock solution is pipetted onto a microtiter plate (MTP) and diluted with water.
  • MTP microtiter plate
  • a spore suspension of Cercospora sojina (containing a biomalt-based aqueous nutrient medium) was given to the stated benodanil concentration.
  • the plates were placed in a water vapor-saturated chamber at temperatures of 18 0 C. Using an absorp- tion photometer, the MTPs were measured at 405 nm on day 7 after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds.
  • Example 5 Curative activity against soybean rust caused by Phakopsora pachyrhizi Leaves of potted soybean seedlings were inoculated with a spore suspension of soybean rust (Phakopsora pachyrhizi). The pots were then placed into a chamber with high atmospheric humidity (90-95%) at 23 to 27°C for 24 hours. After 2 days, the infected plants were sprayed to runoff point with the benodanil solution at the concentration of active compound stated below. After the spray coating had dried on, the test plants were cultivated in a greenhouse at temperatures between 23 and 27°C and at 60 to 80% relative atmospheric humidity for 14 days. The extent of the rust fungus development on the leaves was then determined.
  • Example 6 Seed dressing trial, activity against soybean rust
  • Soybean seeds of the cultivar BRS 133 were treated with 1000 g of benodanil / 100 kg of seed, formulated as SC with 250 g of active compound per liter, as liquid dressing, then sown into pots and cultivated in a greenhouse at about 22°C. 3 weeks after sowing, the plants were inoculated with soybean rust, incubated at 100 % relative atmospheric humidity for 24 hours and then again cultivated in the greenhouse. At the time of inoculation, the first pair of leaves and one subsequent leaf had developed. The infection of the leaves was assessed 1 1 days after the inoculation.
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the product benodanil was used as commercial finished formulation and diluted with water to the stated concentration of the active compound.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of Sep- toria glycines in an aqueous biomalt solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.
  • An efficacy of 0 means that the growth level of the pathogens corresponds to that of the untreated control; an effi- cacy of 100 means that the pathogens were not growing.
  • the efficacy (E) is calculated as follows using Abbot's formula:
  • ⁇ corresponds to the fungicidal infection of the treated plants in % and ⁇ corresponds to the fungicidal infection of the untreated (control) plants in %

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Abstract

A method for controlling Alternaria spp., Cercospora kikuchi, Cercospora sojina, CoIIetotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybeans by employing an effective amount of benodanil, or a mixture thereof with fungicidally, herbicidally and/or insecticidally active compounds according to the description, and seed comprising these mixtures, and compositions containing benodanil.

Description

Method for controlling specific fungal pathogen in soybeans by employing benodanil
Description
The invention relates to a method for controlling Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybeans.
Over recent years, there has been an increase in severe infections of soybean crops in South America by the harmful fungi Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and Septoria glycines, resulting in considerable harvest and yield losses. Most customary fungicides are unsuitable for controlling the abovementioned pathogens in soybeans, or their action against those pathogens is unsatisfactory.
Surprisingly, it has now been found that benodanil exhibits excellent activity against Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybean crops.
In the method according to the invention, the activity is increased considerably by the joint application, in synergistically effective amounts, of benodanil and a second carboxamide fungicide (I) or an azole fungicide (II). Suitable carboxamide fungicides (I) are selected from the group consisting of flutolonil, mepronil, carboxin, fenfuram and furametpyr. Suitable azole fungicides (II) are selected from the group consisting of azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusil- azole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, eth- aboxam, etridiazole, hymexazole oxpoconazol, paclobutrazol, uniconazol, 1-(4-chloro- phenyl)-2-([1 ,2,4]triazol-1-yl)-cycloheptanol and imazalilsulfphate.
Benodanil, the carboxamide and the azole fungicides mentioned above, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); many of them are commercially available. Benodanil and the azole fungicides can be present in various crystal modifications which may differ in their biological activity. Their use also forms part of the subject matter of the present invention.
Preference is given to mixtures of benodanil with a carboxamide fungicide (I).
In another aspect of the invention, preference is given to mixtures of benodanil with an azole fungicide (II).
Preference is also given to mixtures of benodanil with an azole fungicide (II) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam.
Particular preference is also given to mixtures of benodanil with an azole fungicide (II) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl and carbendazim.
Very particular preference is also given to mixtures of benodanil with an azole fungicide (II) selected from the group consisting of epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim, especially an azole fungicide selected from epoxiconazole and metconazole.
When preparing the mixtures, it is preferred to employ benodanil and the fungicide I or Il in pure form, to which further compounds active against other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers can be added.
Usually, mixtures of benodanil and one fungicide I or Il are employed. However, in certain cases mixtures of benodanil with two or, if appropriate, more active components may be advantageous.
The further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to benodanil.
Accordingly, the invention also relates to fungicidal mixtures for controlling Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines, which mixtures comprise, as active components,
1 ) benodanil and
2) a fungicide I or Il as defined above in synergistically effective amounts.
Benodanil, alone or in combination with a fungicide I or II, is preferably suitable for controlling the pathogens Phakopsora pachyrhizi and Phakopsora meibomiae, in particular Phakopsora pachyrhizi, in soybeans.
In another preferred embodiment of the invention, benodanil, alone or in combination with a fungicide I or II, is suitable for controlling the pathogens Alternaria spp., Cerco- spora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa and Septoria glycines, in particular Cercospora kikuchi, Cerco- spora sojina, Colletotrichum truncatum, Corynespora cassiicola and Microsphaera diffusa , even more preferred Microsphaera diffusa.
Benodanil and the fungicide I or Il can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The harmful fungi are controlled by applying benodanil by treating the seed, by spraying or dusting the plants or the soil before or after sowing of the plants, or before or after emergence of the plants.
The fungal pathogens in soybeans are controlled advantageously by applying an aqueous preparation of a formulation comprising benodanil to the above-ground parts of the plants, in particular the leaves, or, as a prophylactic on account of the high systemic effectiveness, by treating the seed or the soil.
Benodanil and the fungicide I or Il mentioned above are usually applied in a weight ratio of from 100:1 to 1 :100, preferably from 20:1 to 1 :20, in particular from 10:1 to 1 :10.
In the method according to the invention, benodanil can advantageously be applied together with other active compounds, in addition to the abovementioned fungicides I or Il also with herbicides, insecticides, growth regulators or else with fertilizers. Suitable further mixing partners of this nature are in particular: • herbicides such as glyphosate, sulfosate, gluphosinate, tefluthrin, terbufos, chlor- pyrifos, chlorethoxyfos, tebupirimfos, phenoxycarb, diofenolan, pymetrozine, imazethapyr, imazamox, imazapyr, imazapic or dimethenamid-P;
• insecticides such as fipronil, imidacloprid, acetamipird, nitenpyram, carbofuran, car- bosulfan, benfuracarb, dinotefuran, thiacloprid, thiamethoxam, clothianidin, diflubenzuron, flufenoxuron, teflubenzuron and alpha-cypermethrin.
Benodanil and the other active compounds mentioned above are usually employed in a weight ratio of from 100:1 to 1 :100, preferably from 20:1 to 1 :20, in particular from 10:1 to 1 :10.
The mixtures, described above, of benodanil with herbicides are used in particular in a soybean variety, in which the sensitivity of the plants to these herbicides is reduced, for example as a result of breeding, including genetic engineering methods.
When benodanil is used in soybeans, the yields are increased considerably. Thus, benodanil may also be used to increase the yield. By virtue of the yield increase in combination with the excellent action of benodanil against fungal diseases in soybean crops, the method according to the invention is of particular benefit to the farmer. Ex- cellent results can be achieved by using benodanil in combination with at least one second fungicidally active compound I or II.
Benodanil or its mixtures with fungicidally, insecticidally and/or herbicidally active compounds, is/are applied by treating the fungi or the soybean plants, materials or seeds to be protected against fungal attack or the soil with a fungicidally effective amount of the active compounds. Application can be both before and after the infection of the materials or plants with the fungi.
If benodanil is used on its own, the application rates in the method according to the invention are from 0.01 to 1.5 kg of active compound per ha, depending on the type of effect desired.
In the treatment of seed, the amounts of active compound required are generally from 1 to 1500 g of benodanil preferably from 10 to 500 g, per 100 kilograms of seed.
Depending on the desired effect and the growth stage of the plants, the application rates of the mixtures according to the invention are from 10 g/ha to 2500 g/ha, preferably from 50 to 2000 g/ha, in particular from 100 to 1500 g/ha. When using the mixtures, the application rates for benodanil are correspondingly generally from 1 to 1000 g/ha, preferably from 10 to 750 g/ha, in particular from 20 to 500 g/ha.
Correspondingly, the application rates for the further fungicidally, insecticidally and/or herbicidally active compound are generally from 1 to 1500 g/ha, preferably from 10 to 1250 g/ha, in particular from 20 to 1000 g/ha.
In the treatment of seed, application rates of mixture are generally from 1 to 2000 g/100 kg of seed, preferably from 1 to 1500 g/100 kg, in particular from 5 to 1000 g/100 kg.
For use in the method according to the invention, the compounds can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.
The formulations are prepared in a known manner [cf., for example, US 3,060,084, EP-A 707 445 (liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th edition, McGraw- Hill, New York, 1963, pages 8-57, WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961 , Hance et al., Weed Control Handbook, 8th edition, Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001 , 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8)], for example by extending the active com- pound with solvents and/or carriers, if desired using emulsifiers, surfactants, dispers- ants, stabilizers, antifoams and antifreeze agents. For formulations for treating seed, color pigments (for example rhodamine B), binders and/or swelling agents may additionally be considered.
Solvents/auxiliaries suitable for this purpose are essentially:
- water, aromatic solvents (for example Solvesso® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used. - carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silicic acid, silicates); emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
Suitable for use as surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearyl phenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Suitable antifreeze agents are, for example, glycerol, ethylene glycol and propylene glycol.
Suitable antifoams are, for example, silicon stearates or magnesium stearates.
A suitable swelling agent is, for example, carrageen (Satiagel®).
Binders serve to improve the adhesion of the active compound or the active compounds on the seed. Suitable binders are, for example, polyethylene oxide/polypropylene oxide copolymers, polyvinyl alcohol, polyvinylpyrrolidone, poly(meth)acraylate, polybutene, polyisobutylene, polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine (Lupasol®, Polymin®), polyethers, polyure- thanes, polyvinyl acetate and the copolymers of the above polymers.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
For seed treatment, the formulations can be diluted 2 to 10 times, resulting in ready-to- use preparations comprising from 0.01 to 60% by weight of the active compound(s), preferably from 0.1 to 40% by weight of the active compound(s).
The following are examples of formulations: 1. Products for dilution with water
A) Water-soluble concentrates (SL, LS)
10 parts by weight of active compound(s) are dissolved with 90 parts by weight of water or a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound dissolves upon dilution with water. This gives a formula- tion having an active compound content of 10% by weight.
B) Dispersible concentrates (DC)
20 parts by weight of active compound(s) are dissolved in 70 parts by weight of cyclo- hexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyr- rolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.
C) Emulsifiable concentrates (EC)
15 parts by weight of active compound(s) are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.
D) Emulsions (EW, EO, ES) 25 parts by weight of active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.
E) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of active compound(s) are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.
F) Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetting agents and made into water-dispersible or water- soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight.
G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.
H) Gels (GF)
20 parts by weight of active compound(s) are, with addition of 10 parts by weight of dispersants, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent, comminuted in a bead mill to give a fine active compound suspension. Dilution with water affords a stabile suspension of the active compound. The formulation has an active compound content of 20 parts by weight. 2. Products to be applied undiluted
J) Dustable powders (DP, DS)
5 parts by weight of active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product with an active compound content of 5% by weight.
K) Granules (GR, FG, GG, MG)
0.5 part by weight of active compound(s) is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules with an active compound content of 0.5% by weight to be applied undiluted.
L) ULV solutions (UL) 10 parts by weight of active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product with an active compound content of 10% by weight to be applied undiluted.
Suitable for seed treatment are in particular FS formulations. Typically, such an FS formulation comprises 1 to 800 g of active compound(s)/l, 1 to 200 g of surfactant/I, 0 to 200 g of antifreeze/I, 0 to 400 g of binder/I, 0 to 200 g of color pigment/I and ad 1 liter of a solvent, preferably water.
The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, with these concentrates being suitable for dilution with water. The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.
The active compounds may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active compounds even, if appropriate, not until immediately prior to use (tank mix). These agents are typically admixed with the compositions according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1.
Use examples
Benodanil was employed as a commercial finished formulation and diluted with water to the stated concentration of active compound.
Example 1 - Activity against Colleotrichum truncatum
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Colleotrichum truncatum in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. In this test the sample - treated with 63 ppm of benodanil - showed 69 % efficacy.
Example 2 - Activity against Septoria glycines The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria glycines in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. In this test the sample - treated with 63 ppm of benodanil - showed 100 % efficacy.
Example 3 - Activity against Alternaria solani
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate
(MTP) and diluted with water to the stated concentrations. A spore suspension of Alter- naria solani in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. In this test the sample - treated with 63 ppm of benodanil - showed 79 % efficacy.
Example 4 - Activity against Cercospora sojina A solution containing 10 mg a.i. per 1 ml dimethyl sulfoxide is prepared. The stock solution is pipetted onto a microtiter plate (MTP) and diluted with water. In a second step a spore suspension of Cercospora sojina (containing a biomalt-based aqueous nutrient medium) was given to the stated benodanil concentration. The plates were placed in a water vapor-saturated chamber at temperatures of 180C. Using an absorp- tion photometer, the MTPs were measured at 405 nm on day 7 after the inoculation.
The measured parameters were compared to the growth of the active compound-free control variant and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds.
Example 5 - Curative activity against soybean rust caused by Phakopsora pachyrhizi Leaves of potted soybean seedlings were inoculated with a spore suspension of soybean rust (Phakopsora pachyrhizi). The pots were then placed into a chamber with high atmospheric humidity (90-95%) at 23 to 27°C for 24 hours. After 2 days, the infected plants were sprayed to runoff point with the benodanil solution at the concentration of active compound stated below. After the spray coating had dried on, the test plants were cultivated in a greenhouse at temperatures between 23 and 27°C and at 60 to 80% relative atmospheric humidity for 14 days. The extent of the rust fungus development on the leaves was then determined. Example 6 - Seed dressing trial, activity against soybean rust
Soybean seeds of the cultivar BRS 133 were treated with 1000 g of benodanil / 100 kg of seed, formulated as SC with 250 g of active compound per liter, as liquid dressing, then sown into pots and cultivated in a greenhouse at about 22°C. 3 weeks after sowing, the plants were inoculated with soybean rust, incubated at 100 % relative atmospheric humidity for 24 hours and then again cultivated in the greenhouse. At the time of inoculation, the first pair of leaves and one subsequent leaf had developed. The infection of the leaves was assessed 1 1 days after the inoculation.
Example 7 - Synergistic activity of benodanil mixtures against Septonia glycines
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
The product benodanil was used as commercial finished formulation and diluted with water to the stated concentration of the active compound. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Sep- toria glycines in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies. An efficacy of 0 means that the growth level of the pathogens corresponds to that of the untreated control; an effi- cacy of 100 means that the pathogens were not growing.
The efficacy (E) is calculated as follows using Abbot's formula:
E = (1 - α/β) - 100
α corresponds to the fungicidal infection of the treated plants in % and β corresponds to the fungicidal infection of the untreated (control) plants in %
The expected efficacies of active compound combinations were determined using Colby's formula (Colby, S. R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, ^5, pp. 20-22, 1967) and compared with the observed efficacies.
Colby's formula: E = x + y - x °y/100
E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b
Figure imgf000014_0001
All microtiter tests make it clear that, by virtue of the synergism, the mixtures according to the invention are considerably more active than had been predicted using Colby's formula.

Claims

Claims
1. A method for controlling at least one fungal pathogen, selcted from Alternaria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynes- pora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora mei- bomiae and/or Septoria glycines in soybeans, wherein the plants, the seed and/or the soil are treated by spraying or dusting a fungicidally effective amount of benodanil.
2. The method according to claim 1 , wherein the fungal pathogen Phakopsora pachyrhizi and/or Phakopsora meibomiae is controlled.
3. The method according to claim 1 , wherein Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola and/or Microsphaera diffusa is controlled.
4. The method according to claim 1 , wherein an aqueous preparation of benodanil is applied to the above-ground parts of the plants.
5. The method according to claim 1 , wherein the fungal pathogen(s) is/are controlled by seed treatment or soil treatment.
6. The method according to any of claims 1 to 5, wherein a combination of benodanil and a carboxamide fungicide (I), selected from the group consisting fo car- boxin, fenfuram, flutolanil, furametpyr and mepronil, is employed.
7. The method according to any of claims 1 to 5, wherein a combination of benodanil and an azole fungicide (II), selected from the group consisting of azacona- zole, bitertanol, bromu-conazole, cypro-conazole, difenoconazole, diniconazole, diniconazole-M, enilconazole, epoxiconazole, fluquin-conazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, pencon-azole, propiconazole, prothiocon-azole, simeconazole, tri- adimefon, triadimenol, tebuconazole, tetraconazole, triti-conazole, prochloraz, pe- furazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabenda- zole, fuberidazole, ethaboxam, etridiazole, hymexazole oxpoconazol, pa- clobutrazol, uniconazol, 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1-yl)-cycloheptanol and imazalil-sulfphate, is employed.
8. The method according to any of claims 1 to 7, wherein a combination of beno- danil and at least one commercial herbicide tolerated by a soybean variety is em- ployed.
9. The method according to any of claims 1 to 7, wherein a combination of beno- danil and at least one commercial insecticide is employed.
10. The method according to any of claims 1 to 7, wherein a combination of beno- danil and at least one active compound selected from the following groups is employed:
• glyphosate, sulphosate, gluphosinate, tefluthrin, terbufos, chlorpyrifos, chloroethoxyfos, tebupirimfos, phenoxycarb, diofenolan, pymetrozine, imazethapyr, imazamox, imazapyr, imazapic or dimethenamid-P;
• fipronil, imidacloprid, acetamiprid, nitenpyram, carbofuran, carbosulfan, benfuracarb, dinotefuran, thiacloprid, thiamethoxam, clothianidin, diflubenzuron, flufenoxuron, teflubenzuron and alpha-cypermethrin.
1 1. The method according to any of claims 7 to 10, wherein benodanil and the second active compound are applied simultaneously, that is jointly or separately, or in succession.
12. The method according to any of claims 7 to 10, wherein the mixture according to any of claims 7 to 10 is applied in an amount of from 5 g/ha to 2500 g/ha.
13. A fungicidal mixture for controlling Alternaria spp., Cercospora kikuchi, Cerco- spora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakopsora meibomiae and/or Septoria glycines in soybeans which comprises, as active components,
1 ) benodanil and
2) at least one fungicide I or Il according to claim 6 or 7, in synergistically effective amounts.
14. The fungicidal mixture according to claim 13, comprising benodanil and the fungicide I or Il in a weight ratio of from 100:1 to 1 :100.
15. A fungicidal mixture comprising, as active components, A) benodanil and
B) glyphosate, sulphosate, gluphosinate, tefluthrin, terbufos, chlorpyrifos, chloroethoxyfos, tebupirimfos, phenoxycarb, diofenolan, pymetrozine, imazethapyr, imazamox, imazapyr, imazapic or dimethenamid-P; in a weight ratio of from 100:1 to 1 :100.
16. A fungicidal agent comprising a liquid or solid carrier and a mixture according to any of claims 13 to 15.
17. The method according to claim 1 , wherein benodanil is applied in an amount of from 1 to 2000 g/100 kg of seed.
18. The method according to any of claims 7 to 10, wherein a mixture of benodanil and the further active compound is applied in an amount of in total from 1 to 2000 g/100 kg of seed.
19. Seed comprising the mixture according to any of claims 13 to 15 in an amount of from 1 to 2000 g/100 kg.
20. The use of benodanil according to claim 1 and, if desired, a fungicide I or Il ac- cording to claim 6 or 7, for preparing a composition suitable for controlling Alter- naria spp., Cercospora kikuchi, Cercospora sojina, Colletotrichum truncatum, Corynespora cassiicola, Microsphaera diffusa, Phakopsora pachyrhizi, Phakop- sora meibomiae and/or Septoria glycines in the crop soja.
PCT/EP2008/055312 2007-05-02 2008-04-30 Method for controlling specific fungal pathogen in soybeans by employing benodanil WO2008135480A2 (en)

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CN102017958B (en) * 2009-09-22 2013-06-19 南京华洲药业有限公司 Composite insecticidal composition containing pymetrozine and propylene glycol alginate and application thereof
CN103766387A (en) * 2014-01-26 2014-05-07 江西农业大学 Suspended seed coating as well as preparation method and application thereof
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