AU2005253726B8 - Use of (E)-5-(4-chlorbenzyliden)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl) cyclopentanol for combating rust attacks on soya plants - Google Patents

Abstract

The invention relates to the use of triticonazole for combating rust attacks on soya, in addition to a method for combating rust attacks on soya, wherein the soya plants and/or the seeds thereof are treated with an effective amount of triticonazole.

Description

1 Use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1 -(I H-1,2,4-triazol-1 -yl methyl)cyclopentanol for controlling rust disease on soybean plants The invention relates to the use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1 5 (IH-1,2,4-triazol-1-ylmethyl)cyclopentanol for controlling rust disease on soybean plants. Until recently, the main growing areas for soybean cultures were free from diseases caused by harmful fungi, such as rust, which were of economical 10 importance. However, in 2001 and 2002, South America saw increasingly serious rust diseases in soybean cultures caused by the harmful fungi Phakopsora pachyrhizi and Phakopsora meibomiae. The results were considerable harvest and yield losses. 15 Most current fungicides are not suitable for controlling rust diseases in soybean cultures because they do not sufficiently inhibit the multiplication of the harmful fungi which cause the rust disease, such as Phakopsora pachyrhizi and Phakopsora meiborniae. Moreover, there is a risk of the fungicidal active ingredient adversely affecting the symbiosis of root nodule bacteria (Rhizobium 20 and Bradyrrhizobium) and soybean plants, thus causing yield loss. CA 2,437,183 describes the use of strobilurins for the treatment of rust diseases on legumes. 25 However, there is a basic need for providing further active ingredients against certain fungal diseases to avoid the development of resistance. It was therefore an object of the invention to provide a further agent which aims to make possible an effective control of rust diseases on soybean plants. In 30 particular, the agent should have no adverse effect on the symbiosis of root nodule bacteria and soybean plants. Surprisingly, it has now been found that (E)-5-(4-chlorobenzylidene)-2,2-dimethyl 1 -(1 H-1,2,4-triazol-1 -ylmethyl)cyclopentanol efficiently inhibits the multiplication of 35 the abovementioned harmful fungi and is thus suitable for controlling the rust disease on soybean plants which is caused by these harmful fungi.

1a The invention therefore relates to the use of (E)-5-(4-chlorobenzylidene)-2,2 dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanoI for controlling rust disease on soybean plants and to a method for controlling rust disease on these plants in which the plant which requires such a treatment, or parts of this plant or the soil 5 which is intended for culturing or growing the plant, is treated with (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -ylmethyl)cyclopentanol. In a first aspect of the invention there is provided the use of (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-I -ylmethyl)cyclopentanol for 10 controlling rust disease on soybean plants, wherein the rust disease is caused by Phakopsora pachyrhizi or Phakopsora meibomiae. In a further aspect of the invention there is provided a method for controlling rust disease on soybeans, wherein the soybean plants, the soil in which the soybean 15 plants are gowen or their seed are treated with an effective amount of (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -ylmethyl)cyclopentanol before or after attack by rust. Yet a further aspect of the invention provides for a fungicidal mixture of (E)-5-(4 20 chlorobenzylidene)-2 ,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanoI with at least one strobilurin selected from the group consisting of trifloxystrobin, pyraclostrobin, orysastrobin, fluxastrobi and azoxystrobin.

2 The use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl)cyclopentanol efficiently prevents infection of the soybean plants with rust disease (protective treatment) and, moreover, also leads to a cure for plants which are already diseased (curative treatment). 5 Surprisingly, rust disease of soybean plants can also be prevented efficiently by treating the seed with (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl)cyclopentanol. 10 Moreover, it has unexpectedly emerged that the symbiosis of the root nodule bacteria with the soybean plants is not, or at least not substantially, adversely affected by the application of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl)cyclopentanol. 15 Both the racemate of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl)cyclopentanol and its enantiomers and nonracemic mixtures of these enantiomers are suitable in accordance with the invention. (E)-5-(4 Chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol is known to the skilled worker under the name triticonazole and commercially available. 20 The term "plant parts" here and hereinbelow comprises not only the aerial plant parts such as foliage, but also the subterranean plant parts, i.e. the root system, and the fruits and seeds. 25 To control the rust disease, the soybean plants, or the plant parts to be protected from rust attack, or the soil, are treated with such an amount of an active ingredient preparation comprising triticonazole as is necessary for controlling the rust disease. The way in which the active ingredient preparation is applied depends in a known manner on the intended use and the type of application. Expediently, the type of active 30 ingredient preparation is chosen in such a way that a fine and uniform distribution of the active ingredient(s) is ensured. In a first preferred embodiment of the invention, the aerial plant parts of the soybean plants, in particular the leaves, are treated with a suitable preparation of the active 35 ingredient. Preferably, triticonazole is employed in an aqueous spray mixture. As a rule, the triticonazole application rates required for protective treatment of the aerial plant parts amount to 10 to 1000 g/ha, in particular to 20 to 500 g/ha. 40 As a rule, the triticonazole application rates required for curative treatment of the aerial plant parts amount to 10 to 1000 g/ha, in particular to 20 to 500 g/ha.

3 In another embodiment of the invention, the seed is treated with a preparation of the active ingredient which is suitable for seed treatment. Active ingredient preparations for seed treatment are, in particular, aqueous spray mixtures, ready-to-use dusts and ULV solutions. In the case of seed treatment, triticonazole is generally employed in an 5 amount of from 1 to 500 g, preferably 10 to 200 g, per 100 kilograms of seed. Moreover, other harmful fungi which are frequently found in soybean plants can also be controlled very effectively with the method according to the invention. The most important fungal diseases in soybeans are listed hereinbelow: 10 * damping-off caused by Rhizoctonia solani, * stem rot caused by Fusarium solani, * stem rot caused by Fusarium spp., * stem and pod blight caused by Phomopsis phaseoli + spp., 15 e purple blotch caused by Cercospora kikuchi, * frogeye leaf spot caused by Cercospora sojina, * seedling blight caused by Pythium spp., e stem antrachnose caused by Colletotrichum demativum var. truncata, * brown spot caused by Septoria glycines, 20 * leaf spot caused by Cercospora spp., * powdery mildew caused by Erysiphe polygoni. To widen the spectrum of action, triticonazole can also be employed together with other active ingredients which are used in soybean growing, for example together with 25 herbicides, insecticides, nematicides, growth regulators, fungicides or else fertilizers. The following list of active ingredients with which triticonazole can be used in accordance with the invention is intended to illustrate the possible combinations, but not to impose any limitation: 30 Fungicides: * acylalanines, in particular oxadixyl; e amine derivatives, in particular guazatine, iminoctadine; " azoles, in particular difenoconazole, epoxyconazole, fenbuconazole, 35 fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole; * dicarboximides such as iprodion, procymidon, vinclozolin; 4 * heterocylic compounds such as anilazin, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dithianon, famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, 5 thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazol, triforine; * nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthal isopropyl; e phenylpyrroles such as fenpiclonil or fludioxonil; * sulfur; 10 * other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl aluminum, iprovalicarb, hexachlorobenzene, metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, 15 zoxamid; * strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin; * sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid cinnamamides and analogs such as dimethomorph, flumetover or flumorph. 20 Insecticides/acaricides: " organo(thio)phosphates, in particular acephate; " carbamates, in particular alanycarb, benfuracarb, bendiocarb, carbosulfan, 25 fenoxycarb, furathiocarb, methiocarb, methomyl, thiodicarb, triazamate; * pyrethroids such as allethrin, bifenthrin, cyfluthrin, cyphenothrin, cypermethrin and the alpha-, beta-, theta- and zeta isomers, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda-cyhalothrin, imiprothrin, permethrin, prallethrin, pyrethrin I, pyrethrin 1l, silafluofen, tau 30 fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, zeta-cypermethrin; " neonicotinoids such as flonicamid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nithiazin, acetamiprid, thiacloprid; * pyrazole insecticides such as acetoprole, ethiprole, fipronil, tebufenpyrad, tolfenpyrad and vaniliprole; 35 e and also spinosad and thiamethoxam. Growth regulators such as chlormethquat and mepiquat. Mixtures of triticonazole with a further fungicide from the azole fungicide group have 40 proved to be very especially suitable for the use according to the invention. Preferred 5 azole fungicides are epoxyconazole, tebuconazole, fluquinconazole, flutriafol, metconazole, myclobutanil, cycproconazole, prothioconazole and propiconazole. By applying triticonazole jointly with a further azole fungicide, an increased activity is obtained so that in total lower application rates of fungicides are required for obtaining 5 the desired fungicidal effect. If triticonazole is employed together with an azole fungicide, the active ingredients will preferably be employed in a triticonazole to azole fungicide weight ratio of from 1:100 to 100:1 and in particular 1:20 to 20:1. In this case, the application rates of further azole 10 fungicide preferably amount to from 1 to 500 g/ha and in particular to 5 to 300 g/ha. Likewise especially suitable for the use according to the invention are mixtures of triticonazole with at least one further fungicide from the strobilurin group which is selected from among trifloxystrobin, pyraclostrobin, orysastrobin, fluoxastrobin and 15 azoxystrobin. If triticonazole is employed together with one of the abovementioned strobilurins, the active ingredients will preferably be employed in a triticonazole to strobilurin weight ratio of from 1:100 to 100:1 and in particular 1:20 to 20:1. In this case, the application 20 rates of strobilurin preferably amount to from 1 to 500 kg/ha and in particular to 5 to 300 kg/ha. If triticonazole is employed jointly with a further fungicidal active ingredient, the latter can be applied simultaneously with triticonazole or after a short time interval, for 25 example within a few days before or after the triticonazole treatment. In the case of simultaneous application, the treatment of the soybean plant can be effected in one pass where a composition comprising triticonazole and the further fungicidal active ingredient are applied, or else in separate passes where different compositions of the individual active ingredients are applied. 30 It has furthermore been proved to be particularly advantageous to employ triticonazole together with at least one active ingredient which is effective against stinging or sucking insects and other arthropods, for example of the order * Coleoptera, in particular Phyllophaga sp. such as Phyllophaga cuyabana, 35 Sternechus sp. such as Sternechus pingusi, Sternechuns subsignatus, Promecops sp. such as Promecops carinicollis, Aracanthus sp. such as Aracanthus morei, and Diabrotica sp. such as Diabrotica speciosa, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, * Lepidoptera in particular Elasmopalpus sp. such as Elasmopalpus lignosellus, 40 * Isoptera, in particular Rhinotermitida, * Homoptera, in particular Dalbulus maidis 6 or against nematodes, including root knot nematodes, for example Meloidogyne spp. such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes such as Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera 5 schachtii, Heterodera trifolii, and other Heterodera species; gall nematodes, for example Anguina species; stem eel worms and foliar nematodes such as Aphelenchoides species. In particular, it has proved useful to employ triticonazole together with at least one 10 insecticide from the neonicotinoid group, specifically with imidacloprid, thiametoxam or clothiamidin, or an insecticide from the group of the pyrazole insecticides, specifically with fipronil. In particular, it has proved useful to employ triticonazole together with an insecticide, in 15 particular a neonicotinoid or pyrazole insecticide, for the treatment of seed or the treatment of seedlings of the soybean plants. If triticonazole is employed jointly with a further insecticidal active ingredient, the latter can be applied simultaneously with triticonazole or after a short time interval, for 20 example within a few days before or after the triticonazole treatment. In the case of simultaneous application, the treatment of the soybean plant can be effected in one pass where a composition comprising triticonazole and the further insecticidal active ingredient are applied, or else in separate passes where different compositions of the individual active ingredients are applied. 25 Since triticonazole has no adverse effect on the symbiosis of the root nodule bacteria and the soybean plants, the treatment of the seed with the active ingredient can be carried out simultaneously or within a narrow time interval around the infection of the seed with the root nodule bacteria. For example, the active ingredient can be applied to 30 the seed jointly with a suitable preparation of the root nodule bacteria, for example an aqueous suspension of the root nodule bacteria. Triticonazole and if appropriate the further active ingredient(s) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the 35 form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, compositions for broadcasting, or granules. The use is typically carried out by means of spraying, atomizing, dusting, broadcasting or pouring. In any case, the use forms and methods should ensure the finest possible distribution of the active ingredients according to the invention. 40 7 Aqueous use forms of the active ingredients can be prepared from commercially available formulations of the active ingredients, for example from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions), by addition of water. To prepare emulsions, pastes or oil dispersions, the substances, as 5 such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, sticker, dispersant or emulsifier. However, it is also possible to prepare concentrates which consist of active substance, wetter, sticker, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water. 10 The concentrations of triticonazole and if appropriate further active ingredient(s) in the ready-to-use preparations can vary within substantial ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1% (% by weight of total active ingredient content, based on the total weight of the ready-to-use formulation). 15 Triticonazole and if appropriate the further active ingredient(s) can also be used successfully in the ultra-low-volume method (ULV), it being possible to apply formulations comprising more than 95% by weight of active ingredient, or indeed the active ingredient without additives. 20 Various types of oils or wetters, adjuvants, herbicides, fungicides, insecticides, nematicides, but also other pesticides, for example bactericides, can be added to the active ingredients, if appropriate also immediately prior to application (tank mix). These agents can be admixed to the compositions according to the invention in a weight ratio 25 of from 1:10 to 10:1. The formulations are prepared in the known manner, for example by extending the active ingredient with solvents and/or carriers, if appropriate using surfactants, i.e. emulsifiers and dispersants. Solvents/carriers which are suitable are essentially: 30 - water, aromatic solvents (e.g. Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, methyl hydroxybutyl ketone, diacetone alcohol, mesityl oxide, isophorone), lactones (for example gamma 35 butyrolactone), pyrrolidones (pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, n-octylpyrrolidone), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, 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 highly-disperse silica, silicates); 40 emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene -8 fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants such as lignin-sulfite waste liquors and methylcellulose. Suitable surfactants are alkali metal salts, alkaline earth metal salts and ammonium 5 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 10 and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, tristerylphenyl 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, 15 lignin-sulfite waste liquors and methylcellulose. 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 and animal origin, aliphatic, 20 cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, mesityl oxide, isophorone, strongly polar solvents, for example dimethyl sulfoxide, 2-pyrrolidone, N-methylpyrrolidone, butyrolactone, or water. 25 Powders, materials for spreading and dusts can be prepared by mixing or jointly grinding the active substances with a solid carrier. Granules, for example coated granules, impregnated granules and homogeneous 30 granules, can be prepared by binding the active ingredients onto solid carriers. Solid carriers are, for example, mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, less, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium 35 nitrate, ureas and plant products such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powder and other solid carriers. In general, the formulations comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, in particular from 5 to 50% by weight, of the active 9 ingredient. In this context, the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum). Examples of formulations are: 5 1. Products for dilution in water A) Water-soluble concentrates (SL) 10 parts by weight of triticonazole are dissolved in water or a water-soluble 10 solvent. Alternatively, wetters or other adjuvants are added. Upon dilution in water, the active ingredient dissolves. B) Dispersible concentrates (DC) 20 parts by weight of triticonazole are dissolved in cyclohexanone with addition of 15 a dispersant, for example polyvinylpyrrolidone. Upon dilution in water, a dispersion results. C) Emulsifiable concentrates (EC) 15 parts by weight of triticonazole are dissolved in xylene with addition of calcium 20 dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Upon dilution in water, an emulsion results. D) Emulsions (EW, EO) 40 parts by weight of triticonazole are dissolved in xylene with addition of calcium 25 dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced into water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Upon dilution in water, an emulsion results. E) Suspensions (SC, OD) 30 20 parts by weight of triticonazole are comminuted in a stirred ball mill with addition of dispersants, wetters and water or an organic solvent to give a fine suspension of active ingredient. Upon dilution in water, a stable suspension of the active ingredient results.

10 F) Water-dispersible and water-soluble granules (WG, SG) 50 parts by weight of triticonazole are ground finely with addition of dispersant and wetters and made into water-dispersible or water-soluble granules by means of technical apparatuses (for example extrusion, spray tower, fluidized bed). 5 Upon dilution in water, a stable dispersion or solution of the active ingredient results. G) Water-dispersible and water-soluble powders (WP, SP) 75 parts by weight of triticonazole are ground in a rotor-stator mill with addition of 10 dispersants, wetters and silica gel. Upon dilution in water, a stable dispersion or solution of the active ingredient results. 2. Products for direct application 15 H) Dusts (DP) 5 parts by weight of triticonazole are ground finely and mixed intimately with 95% finely particulate kaolin. This gives a dust. I) Granules (GR, FG, GG, MG) 20 0.5 part by weight of triticonazole is ground finely and combined with 95.5% carriers. Current methods are extrusion, spray drying or the fluidized bed. This gives granules for direct application. J) ULV solutions (UL) 25 10 parts by weight of triticonazole are dissolved in an organic solvent, for example xylene. This gives a product for direct application. Examples of suitable formulations for the treatment of seeds are: A soluble concentrates (SL, LS) 30 D emulsions (EW, EO, ES) E suspensions (SC, OD, FS) F water-dispersible and water-soluble granules (WG, SG) G water-dispersible and water-soluble powders (WP, SP, WS) H dusts and dust-like powders (DP, DS) 35 Preferred FS formulations of triticonazole for the treatment of seed usually comprise 0.5 to 80% of active compound, 0.05 to 5% of wetter, 0.5 to 15% of dispersant, 0.1 to 5% of thickener, 5 to 20% of antifreeze agent, 0.1 to 2% of antifoam, 1 to 20% of 11 pigment and/or dye, 0 to 15% of adhesive or tackifier, 0 to 75% of filler/vehicle, and 0.01 to 1% of preservative. Suitable pigments or dyes for formulations of triticonazole for the treatment of seed are 5 Pigment blue 15:4, Pigment blue 15:3, Pigment blue 15:2, Pigment blue 15:1, Pigment blue 80, Pigment yellow 1, Pigment yellow 13, Pigment red 112, Pigment red 48:2, Pigment red 48:1, Pigment red 57:1, Pigment red 53:1, Pigment orange 43, Pigment orange 34, Pigment orange 5, Pigment green 36, Pigment green 7, Pigment white 6, Pigment brown 25, Basic violet 10, Basic violet 49, Acid red 51, Acid red 52, Acid red 10 14, Acid blue 9, Acid yellow 23, Basic red 10, Basic red 108. Suitable wetters and dispersants which are used are in particular the abovementioned surface-active substances. Preferred wetters are alkyinaphthalenesulfonates such as diisopropyl- or diisobutylnaphthalenesulfonates. Preferred dispersants are nonionic or 15 anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants which may be mentioned are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ether, for example polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, 20 tristerylphenyl 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 and methylcellulose. Suitable anionic dispersants are, in particular, alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, 25 phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore arylsulfonate-formaldehyde condensates, for example condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and 30 formaldehyde, lignosulfonates, lignin-sulfite waste liquors, phosphated or sulfated derivatives of methylcellulose and polyacrylic acid salts. Antifreeze agents which can be employed are, in principle, all those substances which lower the melting point of water. The suitable antifreeze agents include alkanols such 35 as methanol, ethanol, isopropanol, butanols, glycol glycerol, diethylene glycol and the like. Thickeners which are suitable are all those substances which can be employed for such purposes in agrochemical compositions, for example cellulose derivatives, 40 polyacrylic acid derivatives, xanthan, modified clays and highly-dispersed silica.

12 Antifoams which can be employed are all those foam-inhibiting substances which are conventional for the formulation of agrochemical active substances. Silicone antifoams and magnesium stearate are especially suitable. 5 Preservatives which can be employed are all those preservatives which are employed for such purposes in agrochemical compositions. Examples which may be mentioned are dichlorophene, isothiazolenes such as 1,2-benzisothiazol-3(2H)-one, 2-methyl-2H isothiazol-3-one hydrochloride, 5-chloro-2-(4-chlorobenzyl)-3(2H)-isothiazolone, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro 10 2-methyl-2H-isothiazol-3-one hydrochloride, 4,5-dichloro-2-cyclohexyl-4-isothiazolin-3 one, 4,5-dichloro-2-octryl-2H-isothiazol-3-one, 2-methyl-2H-isothiazol-3-one, 2-methyl 2H-isothiazol-3-one/calcium chloride complex, 2-octyl-2H-isothiazol-3-one and benzyl alcohol hemiformal. 15 Adhesives/tackifiers are added to improve the adhesion of the active components to the seed after treatment. Suitable adhesives are surface-active EO/PO block copolymers, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol@, Polymin@, polyethers and 20 copolymers which are derived from these polymers. To treat the seed, it is possible, in principle, to employ all customary seed treatment or seed dressing methods. Specifically, a procedure is followed in the treatment in which the seed is mixed with the desired amount of seed-dressing agent formulations, either 25 as such or after previous dilution with water, using a suitable device, for example a mixing device, for solid or solid/liquid mixing partners until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying procedure. Use examples 30 Example 1: Curative treatment of diseased soybean plants In field experiments, different varieties of soybean plants whose leaves were already infested with Phakopsora pachyrhizi were treated with an aqueous triticonazole 35 preparation using equipment conventionally used under practice conditions. The application rates were from 20 to 200 g/ha. 25 days after the treatment, the disease level on the untreated, but infested, leaves had developed to such an extent that it covered 50% of the leaf area. In the treated plants, in contrast, Phakopsora pachyrhizi disease had only reached a maximum of 25%. This reduced disease level resulted in 40 markedly improved yield in comparison with the untreated control.

13 Example 2: Protective treatment of diseased soybean plants In field experiments, different varieties of soybean plants were treated with an aqueous triticonazole preparation. The application rates amounted to 20 to 200 g/ha. Thereafter, 5 the plants were inoculated with Phakopsora pachyrhizi. 25 days after the treatment, the disease level on the untreated, but infested, leaves had developed to such an extent that it covered 50% of the leaf area. In the treated plants, in contrast, Phakopsora pachyrhizi disease had only reached a maximum of 25%. This reduced disease level resulted in markedly improved yield in comparison with the untreated control. 10 Example 3: Seed treatment Seed of soybean plants c.v. "Embrapa 48" were treated with a composition suitable for seed treatment, comprising triticonazole as active substance, at application rates in the 15 range of from 12.5 g, 25 g, 50 g, 100 g and 250 g of triticonazole per 100 kg of seed. Thereafter, the seed was sown. The soybean plants thus grown were then inoculated with Phakopsora pachyrhizi. After 50 days, the level of rust disease of the leaf areas was determined. The disease level in the plants from untreated seed was at least 50%, whereas the disease level of the leaf area in plants from treated seed was less than 20 25% in all cases. Example 4: Protective activity of triticonazole via seed treatment against soybean rust caused by Phakopsora pachyrhizi 25 A defined amount of commercially available ready-to-use formulation of triticonazole (suspension concentrate, active substance content 200 g/l) was diluted with water to a total volume of 1 liter/1 00 kg soybeans, corresponding to the desired application rates (ARs) of 5, 15, 30 and 50 g of ai/100 kg of soybeans. 30 Soybean seeds cd. "IAC 8.2" were treated with the resulting aqueous triticonazole suspension in a commercial seed-dressing apparatus and subsequently sown in a field trial in Brazil. The leaves of the Soya plants thus grown were inoculated with a spore suspension of soybean rust (Phakopsora pachyrhizi) when they had reached a suitable growth stage. Thereafter, the plants were kept humid overnight for 6-8 hours, using an 35 irrigation system with fine droplets. During this time, the spores germinated, and the germ tubes penetrated the leaf tissue. 60 days after the treatment (60 DAT) or sowing, the extent of the development of the rust fungus on the leaves of the infected plants was determined. 40 The results are compiled in Table 1: 14 Table 1: AR % infected leaf area g/100 kg (60 DAT) 0 (untreated) 40 5 23 15 11 30 9 50 3 Example 5: Curative activity of triciconazole via spray application against soybean rust caused by Phakopsora pachyrhizi 5 A commercially available ready-to-use formulation of triticonazole (suspension concentrate, active substance content 200 g/l) was diluted with water to the active substance concentration (Asconc.) stated in Table2 and applied. 10 Leaves of pot-grown soybean seedlings cd. "Hutcheson" were inoculated with a spore suspension of soybean rust (Phakopsora pachyrhizi). Thereafter, the pots were placed for 24 hours into a chamber with high atmospheric humidity (90 to 95%) and 22 to 24 0 C. During this time, the spores germinated and the germ tubes penetrated the leaf tissue. 3 days later, the infected plants were sprayed to run off with an aqueous 15 suspension of the active substance concentration stated in Table 2. The suspension or emulsion was compared as described above. After the spray coating has dried on, the test plants were grown for 17 days in the greenhouse at temperatures of between 22 and 24 0 C and a relative atmospheric humidity of 80 to 90%. The extent of the development of the rust fungus on the leaves was then determined. The results are 20 compiled in Table 2: Table 2: Asconc. % infected leaf area ppm (17 DAT)' 0 (untreated) 80 15 9 4 1 14a The following investigations relate to determining the efficacy of triticonazole in controlling rust diseases on soybeans in comparison with other fungicides that are known to be active against rust diseases on cereals. Example 6: Efficacy of triticonazole in controlling rust diseases on soybeans The tests were conducted with the following fungicidal compounds which are known to be active against rust diseases in cereals: triticonazole , azoxystrobin, trifloxystrobin, carboxin, fludioxonil, mefenoxam, metalaxyl, prochloraz, thiophanate-methyl and thiram. The effect of the different fungicides was investigated in seed-treatment trials using seeds of susceptible soybean varieties. A stock solution containing 10,000 ppm of the active ingredient was prepared by dissolving the active ingredient in dimethysulfoxide. The stock solutions were diluted with water to the final concentrations featuring application rates in g/100 kg seed. The active ingredients triticonazole and mefenoxam were used as commercial formulations which were diluted with water accordingly. 1 ml of each dilution was pipetted to soybean seedlings grown in vermiculite. The soybean plants were kept at 21 0 C and at a humidity of ca 70%. 7 days after the treatment the soybean plants were inoculated with an aqueous spore suspension of Phakopsora pachyrhizi. Disease levels were assessed as the % of the infected leaf area 14 days after inoculation. The results are presented in the following Table A: 14b Table A Application rate [g/100 kg seed] Disease level [%Jl) Control 0 80 Triticonazole 25 0 Azoxystrobin 25 63 Trifloxystrobin 25 70 Carboxin 25 70 Fludioxonil 25 70 Mefenoxam 25 63 Metalaxyl 25 70 Prochloraz 25 67 Thiophanate-methyl 25 73 Thiram 25 73 1) % infected leaf area The results summarized in Table A show that triticonazole is the only fungicide which provides effective control of soybean rust, caused by Phakopsora pachyrizi. Example 7: Synerglistic action of triticonazole /strobilurin compositions These experiments relate to examining the synergistic action of triticonazole with strobilurins. The investigations were run as Green House Trials. In the first series, aerial parts of the plants were treated. In the second series, seedlings were treated. Green House Tests: Treatment of aerial parts of soybean plants Preparation of Spray solutions: A stock solution was prepared as follows. A mixture of acetone and/or dimethylsulfoxide and the wetting agentlemulsifier Wettol, which is based on ethoxylated alkyphenoles, in a relation (volume) solvent-emulsifier of 99 to 1, was added to 25mg of the compound to give a total of 10mi.

14c Water was then added to total volume of 1 00mI. This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration. Curative control of soybean rust on soybeans caused by Phakopsora pachyrhizi (Phakpa K3) Leaves of pot-grown soybean seedlings were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and a temperature of 20 to 241C for 24 h. The next day the plants were cultivated for 2 days in a greenhouse chamber at a temperature of 23-27cC and a relative humidity between 60 and 80%. The plants were then sprayed to run-off, with an aqueous suspension, containing the concentration of active ingredient or the mixture as described below. The plants were allowed to air-dry. The trial plants were then cultivated for 14 days in a greenhouse chamber at a temperature of 23-27 0 C and a relative humidity of between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as a % diseased leaf area. The % disease was converted into an efficacy measure using the following formula: Efficacy (%) = 100% (1 - D/Do) D= observed diseases for treated plant Do= observed disease for untreated plant An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected. The expected efficacies of active compound mixtures were determined from the observed efficacies of single treatments using Colby's formula [R.S. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", weeds 15, 20-22 (1967)]. The calculated efficacies were compared with the observed efficacies for combined treatments. Synergism is the difference 14d between calculated efficacy and observed efficacy. The results are presented in the following Table B. Table B: Active Concentration Mixture Observed Calculated Synergism compound/ (ppm) efficacy efficacy (%) active according mixture to Colby (%) Untreated 90% control disease Triticonazole 0.016 - 71 Fluoxastrobin 0.25 - 17 Trixloxystrobin 0.25 - 0 Triticonazole 0.016 1 :16 93 76 17 Fluoxastrobin 0.25 Triticonazole 0.016 1 : 16 95 71 24 Trixloxystrobin 0.25 14e Greenhouse Drench Test Protective control of soybean rust on soybeans caused by Phakopsora pachyrhizi (Phakpa P7) The active compounds were separately dissolved in dimethyl sulfoxide as a stock solution having a concentration of 10,000 ppm and were afterwards diluted with water to their final concentration, respectively, All solutions were applied to the roots of 7 days old soybean seedlings, growing in vermiculite. The following incubation period took a further 7 days at 22*C and an air humidity of 55%. One week later, the primary foliage leaves of the plants were collected and placed onto water agar plates. Subsequently, they were inoculated with a spore suspension of Phakopsora pachyrhizi. To ensure the success of the artifical inoculation, the agar plates were transferred to a humid chamber without light and a relative humidity of 95 to 99% and a temperature of 20 to 221C for about 24 h. The plates were then were incubated for 10 to 12 days in daylight and at a room temperature of about 20 to 24 0 C. The fungal attack on the primary leaves was visually assessed as % diseased leaf area. The disease values were converted into efficacy-data as described above. The expected efficacies of active compound mixtures were determined using Colby's formula [R.S. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, 20-22 (1967)] and compared with the observed efficacies. The results are summarised in Table C.

14f Table C: Active Application Mixture Observed Calculated Synergism Compound/ rate of the efficacy efficacy (%) active active (%) according mixture compound in to Colby g to 100kg (%) seed Untreated 83 (% control affection) Triticonazole 1 - 8 0.25 0 Azoxystrobin 16 - 4 Fluoxastrobin 63 - 8 Orysastrobin 16 - 8 Pyraclostrobin 250 - 28 Triticonazole 1 1: 16 93 12 81 Azoxystrobin 16 Triticonazole 1 1: 63 76 15 61 Fluoxastrobin 63 Triticonazole 0.25 1: 63 66 8 58 Orysastrobin 16 Triticonazole 1 1: 250 90 34 56 Pyracolstrobin 250

Claims (19)

1. The use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1 ylmethyl)cyclopentanol for controlling rust disease on soybean plants, wherein the rust disease is caused by Phakopsora pachyrhizi or Phakopsora meibomiae.

2. The use according to claim 1, wherein the seed is treated.

3. The use according to claim 2, wherein (E)-5-(4-chlorobenzylidene)-2,2 dimethyl-1-(1H--1,2,4-triazol-1-ylmethyl)cyclopentanol is employed in an amount of from 1 to 500 g per 100 kilograms of seed.

4. The use according to claim 1, wherein the aerial plant parts of the soybean plants are treated.

5. The use according to claim 4, wherein (E)-5-(4-chlorobenzylidene)-2,2 dimethyl-l-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol is employed in an amount of from 10 to 1000 g/ha.

6. The use according to any one of claims 1 to 5, wherein (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -yl methyl)cyclopentanol is employed jointly with at least one further fungicide selected from the group of the azole fungicides consisting of epoxyconazole, tebuconazole, fluquinconazole, flutriafol, metconazole, myclobutanil, cycproconazole, prothioconazole and propiconazole.

7. The use according to any one of claims 1 to 6, wherein (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -yl methyl)cyclopentanol is employed jointly with at least one further fungicide selected from the group of the strobilurins consisting of trifloxystrobin, pyraclostrobin, orysastrobin, fluoxastrobin and azoxystrobin.

8. The use according to any one of claims 1 to 7, wherein (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -yl methyl)cyclopentanol is employed jointly with at least one insecticide selected from the pyrazole insecticides and the neonictotinoid group. 16

9. A method for controlling rust disease on soybeans, wherein the soybean plants, the soil in which the soybean plants are grwen or their seed are treated with an effective amount of (E)-5-(4-ch lorobenzyl idene)-2,2-di methyl 1 -(1 H-1,2,4-triazol-1 -ylmethyl)cyclopentanol before or after attack by rust.

10. A fungicidal mixture of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4 triazol-1-ylmethyl)cyclopentanol with at least one strobilurin selected from the group consisting of trifloxystrobin, pyraclostrobin, orysastrobin, fluxastrobi and azoxystrobin.

11. The mixture as claimed in claim 10, wherein the weight ratio of (E)-5-(4 chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4-triazol-1 -yl methyl)cyclopentanol to strobilurin is from 1 : 100 to 100 : 1.

12. The mixture as claimed in claim 10 or 11, wherein the stobilurin is pyraclostrobin.

13. A formulation containing a mixture as claimed in any one of claims 10 to 12.

14. The formulation as claimed in claim 13, which is in the form of a directly sprayable solution, a powder, a suspension, an emulsion and oil dispersion, a paste, a dust or granules.

15. An aqueous ready-to-use preparation containing a mixture as claimed in any one of claims 10 to 12 in a total amount of 0.0001 to 10% by weight of active ingredient based on the total weight of the ready-to-use preparation.

16. The use of E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl)cyclopentanol for controlling rust disease on soybean plants according to claim 1 substantially as hereinbefore described with reference to Examples I to 5.

17. A method for controlling rust disease on soybeans according to claim 9 substantially as hereinbefore described with reference to Examples 1 to 5.

18. The use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1 -(1 H- 1,2,4-triazol-1 -yl methyl)cyclopentanol with at least one strobilurin, for controlling rust disease 17 on soybean plants substantially as hereinbefore described with reference to Examples 1 to 5.

19. A fungicidal mixture of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1 -(1 H-1,2,4 triazol-1-ylmethyl)cyclopentanol with at least one strobilurin substantially as hereinbefore described with reference to Example 7. WATERMARK PATENT AND TRADE MARKS ATTORNEYS BASF SE P28078AU00