ZA200700415B - 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

Description

4 1 * PF 00000556658 =

Use of (E)-5-(4- chlorobenzylidene)-2,2-dimeathyl-1-(1H-1,2,4-triazol- #8 -yl- methyl)cyclopertanol for controlling rust dise2ase on soybean plants

The invention realates to the use of (E)-5-(4-chlorobenzylidene)-2,2-d imethyl-1-(1H- 1,2.4-triazol-1-y Imethyl)cyclopentanol for co mtrolling 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, whick were of economical imgoortance. However, in 2001 and 2002, South America saw incre asingly serious rust dise=ases in soybean cultures caused by the harmful fungi Phakogosora pachyrhizi and Phaakopsora meibomiae. Thea results were considerable Marvest and yield losses.

Most current furgicides are not suitable for controlling rust diseases in soybean cultures becausse they do not sufficiently inh ibit the multiplication of t he harmful fungi which cause thea rust disease, such as Phak=opsora pachyrhizi and PPhakopsora meibomiae. Mo reover, there is a risk of the #ungicidal active ingredie=nt adversely affecting the symmbiosis of root nodule bactemria (Rhizobium and Brad—yrrhizobium) and soybean plants _, thus causing yield loss.

CA 2,437,183 dRescribes the use of strobilurilins for the treatment of r_ist diseases on legumes.

However, there is a basic need for providing further active ingredien—ts against certain fungal diseasess to avoid the development of resistance.

Therefore a nee=d exists to provide a further agent which makes posssible an effective control of rust dlliseases on soybean plants. [In particular, the agent s hould have no adverse effect on the symbiosis of root nodule bacteria and soybear plants.

Surprisingly, it Fas now been found that (£)—5-(4-chlorobenzylidene)—2,2-dimethy!-1- (1H-1,2 4-triazol-1-yimethyl)cyclopentanol e=fficiently inhibits the muliiplication of the abovementione=d harmful fungi and is thus ssuitable for controlling thes rust disease on soybean plants which is caused by these hamful fungi.

The invention tierefore relates to the use of (F)-5-(4-chlorobenzylide=ne)-2,2-dimethyl- 1-(1H-1,2,4-tria zol-1-yimethyl)cyclopentanol for controlling rust dise=ase on soybean plants and to a method for controlling rust d isease on these plants ir which the plant which requires -such a treatment, or parts of this plant or the soil whiach is intended for culturing or growwing the plant, is treated with (£)-5-(4-chlorobenzylid ene)-2,2-dimethyl- 1-(1H-1,2,4-tria zol-1-ylmethyl)cyclopentanoll. 40

AMENDED SHEET

— ’ ", PF 00000556655

The use of (£)-25-(4-chlorobenzylidene)-2,2-dimeethyl-1-(1H-1,2,4-triazol-1~yl- methyl)cyclopemntanol efficiently prevents infectieon of the soybean plants with rust disease (protective treatment) and, moreover, aalso leads to a cure for pla nts which are already disease=d (curative treatment).

Surprisingly, ru=st disease of soybean plants car also be prevented efficie=ntly by treating the seed with (E)-5-(4-chlorobenzyliderme)-2,2-dimethyl-1-(1H-1,22 4-triazol-1-yl- methyl)cyclope ntanol.

Moreover, it ha s unexpectedly emerged that thes symbiosis of the root nocdule bacteria with the soybean plants is not, or at least not substantially, adversely affe=cted by the application of (&&)-5-(4-chlorobenzylidene)-2,2-dlimethyl-1-(1H-1,2,4-triazcal-1-yl- methyl)cyclope ntanol.

Both the racenmmate of (E)-5-(4-chlorobenzyliden e)-2,2-dimethyl-1-(1H-1,2 ,4-triazol-1-yl- methyl)cyclope ntanol and its enantiomers and ronracemic mixtures of these enantiomers are suitable in accordance with thes invention. (E£)-5-(4-

Chlorobenzylid ene)-2,2-dimethyl-1-(1H-1,2,4-trliazol-1-yimethyl)cyclopenttanol is known to the skilled we=orker under the name triticonazoole and commercially avail able.

The term “plant parts” here and hereinbelow co- mprises not only the aerizl plant parts such as foliage=, but also the subterranean plant parts, i.e. the root systerm, and the fruits and seed s.

To control the t—ust disease, the soybean plants , or the plant parts to be p=rotected from rust attack, or t=he soil, are treated with such an amount of an active ingredient preparation comprising triticonazole as is necesssary for controling the ru st disease.

The way in whilich the active ingredient preparation is applied depends in a known manner on the intended use and the type of ap- plication. Expediently, the= type of active ingredient preparation is chosen in such a way thata fine and uniform disstribution of the active ingreadient(s) is ensured.

In a first prefer-red 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 ingredient. Pre=ferably, triticonazole is employecd in an aqueous spray mixture.

As a rule, the toriticonazole application rates recguired for protective treatment of the aerial plant pamrts amount to 10 to 1000 g/ha, ime particular to 20 to 500 g/ka. 40 As a rule, the toriticonazole application rates required for curative treatme nt of the aerial plant parts am ount to 10 to 1000 g/ha, in particcular to 20 to 500 g/ha.

ere ———— . PF 0000055665 ol TR CE

In another embodirmnent of the invention, the seed is treated with a prepoaration of the active ingredient which is suitable for seed treatment. Active ingredient preparations for seed treatment are , in particular, aqueous spray rixtures, ready-to-us e dusts and ULV solutions. In the casse of seed treatment, triticona=ole is generally emp loyed in an amount of from 1 to 500 g, preferably 10 to 200 g , per 100 kilograms of seed.

Moreover, other ha rmful fungi which are frequently found in soybean olants can also be controlled very effe ctively with the method according to the invention. ~The most important fungal diseases in soybeans are listed &hereinbelow: 40 e damping-off caused by Rhizoctonia solani, e stem rot caused by Fusarium solani, e stem rot caused by Fusarium spp., + stem and pod belight caused by Phomopsis ptaaseoli + spp., “15 eo purple blotch caused by Cercospora kikuchi, e frogeye leaf spot caused by Cercospora sojin a, e seedling blight caused by Pythium spp., e stem antrachnosse caused by Collefotrichurn cdemativurn var. trunceata, e brown spot caused by Septoria glycines, eo leaf spot causesd by Cercospora spp., e powdery mildevv caused by Erysiphe polygond.

To widen the spect rum of action, triticonazole car also be employed tcogether with other active ingredients v=vhich are used in soybean gro-wing, for example together with herbicides, insectic ides, nematicides, growth regulators, fungicides or else fertilizers.

The following list of" active ingredients with which triticonazole can be Lised in accordance with thee invention is intended to illustrate the possible conbinations, but not to impose any | imitation:

Fungicides: e acylalanines, in particular oxadixyl; e amine derivativees, in particular guazatine, imi noctadine; e azoles, in particular difenoconazole, epoxycomnazole, fenbuconazotie, fluquiconazole, flusilazole, flutriafol, hexacon=zole, imazalil, metcconazole, myclobutanil, peenconazole, propiconazole, pr-ochioraz, prothiocon=azole, tebuconazole; e dicarboximides such as iprodion, procymidon , vinclozolin;

ee etter reese SAMS APE ————"———————— ro ———————————————— ". PF 0000055665 * heterocylic cosmpounds such as anilazin, ben omyl, boscalid, carbendazim, carboxin, oxyc=arboxin, cyazofamid, dithianon , famoxadon, fenamidon, #enarimol, fuberidazole, —flutolanil, furametpyr, isoprothio»lane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquil on, quinoxyfen, silthiofam_, thiabendazole2, thifluzamid, thiophanate-meth yl, tiadinil, tricyclazol, trifomrine,; « nitrophenyl derivatives such as binapacryl, di nocap, dinobuton, nitroph®hal- isopropyl; « phenyipyrrole:s such as fenpiclonil or fludioxo nit; eo sulfur; eo other fungicid- es such as acibenzolar-S-methyl, benthiavalicarb, carprogoamid, chlorothalonil .. cyflufenamid, cymoxanil, dazo smet, diclomezin, diclocymeet, diethofencarb , edifenphos, ethaboxam, fenh<examid, fentin-acetate, fernoxanil, ferimzone, flu. azinam, fosetyl, fosety! aluminu m, iprovalicarb, hexachior-obenzene, metrafenon, paencycuron, propamocarb, phthalide, toloclofos-methyl, guintozene, zoxamid; eo strobilurins stmch as azoxystrobin, dimoxystro bin, fluoxastrobin, kresoxiem-methyl, metominostro-bin, orysastrobin, picoxystrobin , pyraclostrobin or trifloxysstrobin; e sulfenic acid derivatives such as captafol, ca ptan, dichlofluanid, folpet, tolylfluanid cinnamamide=s and analogs such as dimethommorph, flumetover or flumeorph.

Insecticides/acari cides: e organo(thio)pohosphates, in particular acephaxte; e carbamates, in particular alanycarb, benfuraccarb, bendiocarb, carbosu Ifan, fenoxycarb, faurathiocarb, methiocarb, metho amyl, thiodicarb, triazamate; « pyrethroids smuch as allethrin, bifenthrin, cyfluathrin, cyphenothrin, cypermethrin and the alpha-, be=ta-, theta- and zeta isomers, desltamethrin, esfenvalerate ethofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda-cyhalothri n, imiprothrin, p- ermethrin, prallethrin, pyrethrin 1, pyrethrin Il, silafluofen, tau- fluvalinate, te=fluthrin, tetramethrin, tralomethwrin, transfluthrin, zeta-cypesrmethrin; e neonicotinoidis such as flonicamid, clothianid in, dinotefuran, imidaclopr—id, thiamethoxarn, nitenpyram, nithiazin, acetamiprid, thiacloprid; « pyrazole inse=cticides such as acetoprole, ethiprole, fipronil, tebufenpyr-ad, tolfenpyrad a nd vaniliprole; e and also spirmosad and thiamethoxam.

Growth regulators such as chlormethquat and m-epiquat.

Mixtures of tritico nazole 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 a ". PF 0000055665 azole fungicides are efooxyconazole, tebuconazole, #luquinconazole, flutriezfol, metconazole, myclobutanil, cycproconazole, prothioaconazole and propicornazole. By applying triticonazole jointly with a further azole fungmicide, an increased activity is obtained so that in totam! lower application rates of furgicides are required f~or obtaining 5 the desired fungicidal effect.

If triticonazole is employed together with an azole fumngicide, the active ing redients will preferably be employeed in a triticonazole to azole furgicide weight ratio of from 1:100 ' to 100:1 and in particular 1:20 to 20:1. In this case, t he application rates off further azole fungicide preferably armnount to from 1 to 500 g/ha ard in particular to § to - 300 g/ha.

Likewise especially sui table for the use according to the invention are mixtures of triticonazole with at leamst one further fungicide from &he strobilurin group which is selected from among twrifloxystrobin, pyraclostrobin, corysastrobin, fluoxastr—obin and azoxystrobin.

If triticonazole is empicyed together with one of the &abovementioned strobeilurins, the active ingredients will preferably be employed in a triiticonazole to strobilurin weight ratio of from 1:100 to 1 00:1 and in particular 1:20 to 20:1. In this case, the application rates of strobilurin pref-erably amount to from 1 to 50 Okg/ha and in particu lar to 5 to 300 kg/ha.

If triticonazole is employed jointly with a further fungicidal active ingredient, the latter can be applied simuita neously with triticonazole or asfter a short time interval, for example within a few dllays before or after the triticormazole treatment. In thee case of simultaneous applicaticon, the treatment of the soybe=an plant can be effectzed in one pass where a composition comprising triticonazole amnd the further fungicicdal active ingredient are applied, or else in separate passes wknere different compos itions of the individual active ingredients are applied. it has furthermore beemn proved to be particularly advantageous to employ triticonazole together with at least cene active ingredient which is effective against stinging or sucking insects and other arthr-opods, for example of the ord er e Coleoptera, in particular Phyllophaga sp. such as Phyllophaga cuy—~abana,

Sternechus sp. such as Sternechus pingusi, Sternechuns subsignaatus,

Promecops sp. such as Promecops carinicol lis, Aracanthus sp. suech as

Aracanthus mowrei, and Diabrotica sp. such a s Diabrotica speciosa. , Diabrotica longicornis, Dizabrotica 12-punctata, Diabrotica virgifera, e Lepidoptera in particular Elasmopalpus sp. s uch as Elasmopalpus lignoselius, 40 e lIsoptera, in particular Rhinotermitida, e Homoptera, in particular Dalbulus maidis ee ——— ". PF.0000055665 or against nematodes, including root knot nematodes, for exeample Meloidogyne spp. such as Meloidogyne hapla, Mexloidogyne incognita, Meloido&gyne javanica, and other

Meloidogyne species; cyst-formaing nematodes such as Globsodera rostochiensis and other Globodera species; Heter odera avenae, Heterodera glwycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; ggall 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 insecticide from the neonicotinoid group, specifically with imiedacloprid, 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 togesther with an insecticide, in particular a neonicotinoid or pyrazole insecticide, for the trea—tment of seed or the treatment of seedlings of the soybean plants. if triticonazole is employed jointly with a further insecticidal a-ctive ingredient, the latter can be applied simultaneously with triticonazole or after a sh ort time interval, for example within a few days befo re or after the triticonazole treeatment. In the case of simultaneous application, the tresatment 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.

Since triticonazole has no adve rse 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 areound the infection of the seed with the root nodule bacte ria. For example, the active irgredient can be applied tom 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(ss) can be used as such, in the form of their formulations or the use forms prepared thereefrom, for example in the form of directly sprayable soluti ons, powders, suspensions o-r dispersions, emulsions, oil dispersions, pastes, dusts, compositions for broadcasting , or granules. The use is typically carried out by means of spraying, atomizing, dustingg, broadcasting or pouring.

In any case, the use forms and methods should ensure the finest possible distribution of the active ingredients accord ing to the invention.

I —————————— ". PF DOM00055665

Aqueaus use forms of the active ingredients can be prepared from commercially availaable formulations of the active irgredients, for example frorm emulsion concentrates, pastes or wettable povevders (sprayable powders, «oil dispersions), bly additieon of water. To prepare emulsicons, pastes or oil dispersiors, the substancess, as such «or dissolved in an oil or solvent , can be homogenized in waater by means of wetter, sticker, dispersant or emulsifier. However, it is also poss-ible to prepare concentrates which consist of active substance, wetter, sticker, dispersant or emu 1isifier and, if appropriate, solvent or oil, anc such concentrates are suitable for dilution v=vith water .

The concentrations of triticonazole a nd if appropriate further active ingredient(s) ir the ready-to-use preparations can vary within substantial ranges. Ine general, they are= between 0.0001 and 10%, preferably, between 0.01 and 1% (% by weight of total active ingreclient content, based on the totaal weight of the ready-to-use formulation).

Triticoonazole and if appropriate the faurther active ingredient(s) c=an also be used successfully in the ultra-low-volume method (ULV), it being posssible to apply formulations comprising more than 25% by weight of active ingredient, or indeed the actives ingredient without additives.

Variows types of oils or wetters, adju vants, herbicides, fungicide=s, insecticides, nemanticides, but also other pesticide=s, for example bactericides-, can be added to the actives 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 of fromm 1:10 to 10:1.

The formulations are prepared in the= known manner, for examp le by extending thse actives ingredient with solvents and/o r carriers, if appropriate usi ng surfactants, i.e=. emulssifiers and dispersants. Solvent. sicarriers which are suitable are essentially: - water, aromatic solvents (e.g. Sclvesso products, xylene), paraffins (for exanple mineral oil fractions), alcohols (feor example methanol, butarol, pentanol, ben—=yl a lcohol), ketones (for example cyclohexanone, methyi hydreoxybutyl ketone, d iacetone alcohol, mesityl oxide , isophorone), lactones (for example gamma— b-utyrolactone), pyrrolidones (pyrrolidone, N-methylpyrrolidcone, N-ethylpyrroli=done, re-octylpyrrolidone), acetates (glwycol diacetate), glycols, dimmethy! fatty acid andes, fatty acids and fatty acid esters. In principle, solvent mixtures may also be us ed. . Carriers such as ground natural minerals (for example kaol-ins, clays, talc, ch ak) zand ground synthetic minerals (for example highly-disperse= silica, silicates); 40 e=mulsifiers such as nonionic anc anionic emulsifiers (for ex ample polyoxyeth ylene

E— = . PF.0 000055665 fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispearsants such as

Iagnin-sulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal salts, alkaline earth metal salts arnd ammonium salts of lignosulfonic acid, naphthalene sulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkyla rylsulfonates, alkyl sulfates, alk ylsulfonates, fatty alcool sulfates, fatty acids and sulfated fatty alcohol glycol ethers, fur—thermore condi ensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and Formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isomoctylphenol, octyl phenol, nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, triste=rylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol ard fatty alcohol ethyl ene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl a cohol polyglycol ether acetal, s=orbitol esters, lignim-sulfite waste liquors and methylcellulose.

Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispearsions are mineral oil fractions of medium to high boiling point, stich as kerosene or diesel oil, furthermore coal tar oils a nd oils of vegetable and animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetralhydronaphthalene, alkylated naph thalenes or their derivatives, meethanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, mesityl oxide, isopheorone, strongly polar solvents, for example dimethyl sulfoxide, 2-pyrrolidone, N-methywIpyrrolidone, butyr—olactone, or water.

Powders, materials for spreading and dusts can be prepared by mixin g or jointly grindlling the active substances with a solid carrier.

Grarmules, for example coated granuless, impregnated granules and hosmogeneous granmules, can be prepared by binding the active ingredients onto solidi carriers. Solid carriers are, for example, mineral earths such as silica gels, silicates, talc, kaolin,

Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomacesous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthestic materials, fertili zers such as, for example, ammonium sulfate, ammonium phosp- hate, ammonium nitrate, ureas and plant products such as cereal meal, tree bark meal, wood meal and nutsknell meal, cellulose powder and other solid carriers.

In general, the formulations comprise between 0.01 and 95% by weig ht, preferably betwween 0.1 and 90% by weight, in pa rticular from 5 to 50% by weigh-t, of the active

A —

PF 0000055665 ingredient. In thisz context, the active ingredients are employed in a purity oif from 90% to 100%, preferaboly 95% to 100% (according to NMIR spectrum).

Examples of formulations are: 1. Products foer dilution in water

A) Watemr-soluble concentrates (SL) parts by weight of triticonazole are dissolved in water or a water-seciuble 10 solvent. Alteemnatively, wetters or other adjuvants are added. Upon dilttion in water, the active ingredient dissolves.

B) Dispe=rsible concentrates (DC) 20 parts by weight of triticonazole are dissolved in cyclohexanone wit=h addition of a dispersarnt, for example polyvinylpyrrolidone. Upon dilution in water—, a dispersion results.

C) Emuissifiable concentrates (EC) 15 parts by weight of triticonazole are dissolved in xylene with additio=n of calcium dodecylben. zenesulfonate and castor oil ethoxylate (in each case 5%). Upon dilution in water, an emulsion results.

D) Emulssions (EW, EO) 40 parts by weight of triticonazole are dissolved in xylene with additio-n of calcium dodecylben:zenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is imtroduced into water by means of an emulsifier (Ultraturra>=x) and made into a homogeneous emulsion. Upon dilution in water, an emulsion ressults.

E) Suspe=nsions (SC, OD) 20 parts by weight of triticonazole are comminuted in a stirred ball mi Hwith addition of edispersants, wetters and water or an organic solvent to give a fine suspension of active ingredient. Upon dilution in water, a stable suspeension of the active ingredient results.

EE

PF .0000055665

F) Water-dispersible and water-soluble granules (WG, S G) 50 parts by weight of triticonazo Ye are ground finely with adcdition of dispersant and wetters and made into wate r-dispersible or water-soluble granules by means of technical apparatuses (for example extrusion, spray towe=r, fluidized bed).

S Upon dilution in water, a stable dispersion or solution of the active ingredient results.

G) Water-dispersible and wat er-soluble powders (WP, SF) 75 parts by weight of triticonazolle are ground in a rotor-stateor mill with addition of 10 dispersants, wetters and silica g el. Upon dilution in water, a stable dispersion or solution of the active ingredient mesulits. 2. Products for direct application 15 H) Dusts (DP) parts by weight of triticonazole= are ground finely and mixe=d intimately with 95% finely particulate kaolin. This giv es a dust. )} Granules (GR, FG, GG, M G) 0.5 part by weight of triticonazoles is ground finely and comb ined with 95.5% carriers. Current methods are ex<trusion, spray drying or the fluidized bed. This gives granules for direct application.

J) ULV solutions (UL) 10 parts by weight of triticonazolle are dissolved in an organ ic 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)

D emulsions (EW, EO, ES)

E suspensions (SC, OD, FS)

F water-dispersible and water-soluble granules (WG, SG)

G water-dispersible and water-soltuble powders (WP, SP, WSD

H dusts and dust-like powders (DF, DS)

Preferred FS formulations of triticonazzole for the treatment of see d usually comprise 0.5 to 80% of active compound, 0.05 to 5% of wetter, 0.5 to 15% of dispersant, 0.1 to 59, of thickener, 5 to 20% of antifreeze agent, 0.1 to 2% of antifozam, 1 to 20% of

—_— . PF.000000 55665 pigment aand/or dye, 0 to 15% of adhesives or tackifier, 0 to 75% of filler/vehicle, and 0.01 to 1% of preservative.

Suitable pigments or dyes for formulation s of triticonazole for the treatment of seed are

Pigment blue 15:4, Pigment blue 15:3, Pigment blue 15:2, Pigmertblue 15:1, Pigment blue 80, Pigment yellow 1, Pigment yelioww 13, Pigment red 112, Pigment red 48:2,

Pigment red 48:1, Pigment red 57:1, Pigrment red 53:1, Pigment o range 43, Pigment orange 34, Pigment orange 5, Pigment green 36, Pigment green #, Pigment white 6,

Pigment brown 25, Basic violet 10, Basic violet 49, Acid red 51, Aacid red 52, Acid red 14, Acid blue 9, Acid yellow 23, Basic red 10, Basic red 108.

Suitable vevetters and dispersants which awe used are in particular #he abovementioned surface-asctive substances. Preferred wetters are alkylnaphthalenesulfonates such as diisopropy/I- or diisobutyinaphthalenesulfonates. Preferred dispers ants are nonionic or anionic di=spersants or mixtures of nonion ic or anionic dispersants — Suitable nonionic dispersarmts which may be mentioned are , in particular, ethylene o=xide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylpheno! [oolyglycol ether, for example polyoxyethylene octylphenol eth er, ethoxylated isooctylp Thenol, octylphenol, nonylpherol, alkylphenol polyglycol ethers, tributylphenyl polyglyc ol ether, tristerylph enyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethyle une alkyl ethers, ethoxylatead polyoxypropylene, lauryl alco hol polyglycol ether acetal, sorbitol esters and methylcel3ulose. Suitable anionic dispersaants are, in particular, alkzali metal, alkaline earth metal and ammonium salts of lignossulfonic acid, naphthalen esuilfonic acid, phenolsul—fonic acid, dibutyinaphthalenesuiifonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatt=y alcohol glycol ethers, furthermore arylsulfonate-formald €hyde condensates, for example condensates of sulfonauted naphthalene and naphthale me derivatives with formaldehyde, condensates of naphthalene or of naphth alenesulfonic acid with p henol and formaldehyde, lignosulfonates, lignin-sulfiite waste liquors, phosphs ated or sulfated derivative s of methylcellulose and polyac rylic 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 ineclude alkanols such as methamol, ethanol, isopropanol, butanls, glycol glycerol, diethylene glycol and the like.

Thickenee's which are suitable are all thosse substances which can be employed for such purposes in agrochemical composit fons, for example cellulosse derivatives, 40 polyacryli-c acid derivatives, xanthan, modified clays and highly-disspersed silica.

i —— = . PF 0000055665

Antifoams which can be employed are all those fcam-inhibiting substance s which are conventional for the formulation of agrochemical &=ctive substances. Silico ne antifoams and magnesium stearate are especially suitable.

Preservatives which can be employed are all thosse preservatives which amre employed for such purpose=s in agrochemical compositions. Examples which may bez mentioned are dichloropherme, isothiazolenes such as 1,2-bemnzisothiazol-3(2H)-one, 22-methyl-2H- isothiazol-3-one hydrochloride, 5-chloro-2-(4-chlomrobenzyl)-3(2H)-isothiazeolone, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2—methyl-2H-isothiazol-3-«one, 5-chioro- 2-methyl-2H-isothhiazol-3-one hydrochloride, 4,5-d ichloro-2-cyclohexyl-4-isscthiazolin-3- one, 4,5-dichloro--2-octryl-2H-isothiazol-3-one, 2-ranethyl-2H-isothiazol-3-ore, 2-methyl- 2H-isothiazol-3-cane/calcium chloride complex, 2-octyl-2H-isothiazol-3-one= and benzyl alcohol hemifornal.

Adhesives/tackifi ers are added to improve the adiesion of the active components to the seed after tre=atment. Suitable adhesives are ssurface-active EO/PO block copolymers, but also polyvinyl alcohols, polyvinylpoyrrolidones, polyacrylatess, polymethacrylate=s, polybutenes, polyisobutenes, goolystyrene, polyethylen eamines, polyethyleneamices, polyethyleneimines (LupasoB®, Polymin®, polyethers and copolymers whic h are derived from these polymers.

To treat the seed, it is possible, in principle, to em ploy all customary seed treatment or seed dressing methods. Specifically, a procedure is followed in the treatm ent in which the seed is mixed with the desired amount of seeci-dressing agent formulations, either as such or after previous dilution with water, usingg a suitable device, for exxample a mixing device, fo r solid or solid/liquid mixing partn ers until the compositior is distributed uniformly on the =seed. If appropriate, this is follow ed by a drying proceduree.

Use examples

Example 1: Cura tive treatment of diseased soybeaan plants in field experimemts, different varieties of soybean plants whose leaves were already infested with Phaakopsora pachyrhizi were treated with an aqueous triticon azole preparation using equipment conventionally used under practice conditionzs. The application rates were from 20 to 200 g/ha. 25 daw/s after the treatment, th e disease level on the untresated, but infested, leaves had desveloped to such an exte=nt that it covered 50% of the leaf area. In the treated plants, in contrast, Phakopsor—a pachyrhizi disease had only~ reached a maximum of 25%. Th is reduced disease level resulted in 40 markedly improveed yield in comparison with the umntreated control.

ee et AraP TEAS ——————————————————————————————————————— EE ————— ) . PF.00000556655

Example 2: Protective treatment of diseased ssoybean plants

In field experiments, different varieties of soyb ean plants were treated wwith an aqueous triticonazole preparation. The application ratess amounted to 20 to 200 g_/ha. Thereafter, the plants were inoculated with Phakopsora paachyrhizi. 25 days after thes treatment, the disease level on the untreated, but infested, le=aves had developed to sumch an extent that it covered 50% of the leaf area. In the treated plants, in contrast, PFiakopsora pachyrhizi dise=ase had only reached a maximmum of 25%. This reduced disease level resulted in markedly improved yield in compar-ison with the untreated control.

Example 3: Se ed treatment

Seed of soybeaan plants c.v. “Embrapa 48” wewme treated with a composition suitable for seed treatment, comprising triticonazole as active substance, at application rates in the range of from “12.5 g, 25 g, 50 g, 100 g and 25=0 g of triticonazole per 10-0 kg of seed.

Thereafter, the: seed was sown. The soybean plants thus grown were th en inoculated with Phakopso ra pachyrhizi. After 50 days, thes level of rust disease of the leaf areas was determine d. The disease level in the plants from untreated seed waas at least 50%, whereas the di sease level of the leaf area in p lants from treated seed waas less than 25% in all cases.

Example 4: Protective activity of triticonazole wia seed treatment against soybean rust caused by Phamkopsora pachyrhizi

A defined amo ‘unt of commercially available re=ady-to-use formulation of triticonazole (suspension concentrate, active substance comtent 200 g/l) was diluted =with water to a total volume of 1 liter/100 kg soybeans, corres ponding to the desired ap plication rates (ARs) of 5, 15, 30 and 50 g of ai/100 kg of soy beans.

Soybean seedss cd. "IAC 8.2" were treated with the resulting aqueous tri—ticonazole suspension in & commercial seed-dressing ap gparatus and subsequently— sown in a field trial in Brazil. T he leaves of the Soya plants thus grown were inoculated with a spore suspension of ssoybean rust (Phakopsora pactayrhizi) when they had rea ched a suitable growth stage. “Thereafter, the plants were kept humid overnight for 6-8 hmours, using an irrigation system with fine droplets. During this time, the spores germina ted, and the germ tubes pemetrated the leaf tissue. 60 days after the treatment (60 D AT) or sowing, the extent of thee development of the rust fungts on the leaves of the infected plants was determine d. 40 The results ares compiled in Table 1:

SS

’ ". PF.0000055665

Table 1:

AR ) % infected leaf area 9/100 kg (60 DAT) ones

EC LI

EI CE

Example 5: Curative activity of triciconazole via spray appl#ication against soybear rust caused by Phakopsora pachwrhizi

A commercially available rea«dy-to-use formulation of triticomnazole (suspension concentrate, active substances content 200 g/l) was diluted with water to the actives substance concentration (Asconc.) stated in Tabie2 and applied.

Leaves of pot-grown soybear seedlings cd. "Hutcheson" were inoculated with a sspore suspension of soybean rust (_Phakopsora pachyrhizi). Thereafter, the pots were p laced for 24 hours into a chamber v=ith high atmospheric humiditsy (90 to 95%) and 22 to 24°C. During this time, the spores germinated and the gerrm tubes penetrated the leaf tissue. 3 days later, the infectted plants were sprayed to rur off with an aqueous suspension of the active subsstance concentration stated in Table 2. The suspension or emulsion was compared as diiescribed above. After the spraay coating has dried or, the test plants were grown for 17 days in the greenhouse at temperatures of betweerm 22 and 24°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 a re compiled in Table 2:

Table 2:

Asconc. % infected leaf area ppm (17 DAT) © riveted) w

DE EE

Claims (9)

et ——————— ete ett ———————————_—————————————————————— er ———————_— ee —— v= — efi te — I ——— —.. ’ . PF.0 000055665 We claim:

1. The use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-tmriazol-1- yimethyl)cyclopentanol for controlling rust disease on soybean pla.nts.

2. The use according to claim 1, which is rust disease caused by Ph=kopsora pachyrhizi or Phakopsora meibomiae.

3. The use according to one of the preceding claims, wherein the see=d is treated.

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

5. The use according to either of claims 1 or 2, wherein the aerial plant parts of the soybean plants are treated.

6. The use according to claim 5, wherein (E)-5-(4-chlorobenzylidene )-2,2-dimethyl- 1-(1H-1,2,4-triazoi-1-yimethyl)cyclopentanol is employed in an arrmount of from 10 to 1000 g/ha.

7. The use according to one of the preceding claims, wherein (£)-5-(C4- chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol is employed jointly with at least one further fungicide from the group of the azole fungicides selected from among epoxyconazole, tebuconazole, flLuquinconazole, flutriafol, metconazole, myclobutanil, cycproconazole, prothioconzazole and propi- conazole.

8. The use according to one of the preceding claims, wherein (E)-5-C4- chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1 -yimethyl)cyclopentanol is employed jointly with at least one further fungicide from the group of the stro- bilurins selected from among trifloxystrobin, pyraclostrobin, orysasstrobin, fluox- astrobin and azoxystrobin.

9. The use according to one of the preceding claims, wherein (E)-5-a(4- chiorobenzylidene)-2,2-dimethyi-1-(1H-1,2,4-triazol-1 -yimethyl)cysclopentanol is employed jointly with at least one insecticide from the group of thes pyrazole in- secticides and the neonictotinoid group.

g PF 0000055665 We claim:

1. The use of (4£)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2 4-triazcOkH1- yimethyl)cyc=lopentanol for controlling rust dissease on soybean plants.

2. The use acc=ording to claim 1, which is rust dilisease caused by Phakorosora pachyrhizi omr Phakopsora meibomiae.

3. The use acc-ording to any one of the precedi ng claims, wherein the se ed is treated.

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

5. The use acc=ording to either of claims 1 or 2 _, wherein the aerial plant poarts of the soybean pla nts are treated.

6. The use acc=ording to claim 5, wherein (E)-5—(4-chlorobenzylidene)-2, 2-dimethyl- 1-(1H-1,2,4-triazol-1-yimethyl)cyclopentanol is employed in an amount of from 10 to 1000 g/hem.

7. The use acc-ording to any one of the precedi ng claims, wherein (E)-5-C4- chiorobenzy lidene)-2,2-dimethyl-1-(1H-1,2,4 -triazol-1-ylmethyl)cyclopentanol is employed jo intly with at least one further fun=gicide from the group of tte azole fungicides selected from among epoxyconaz=ole, tebuconazole, fluquiriconazole, flutriafol, me tconazole, myclobutanil, cycprocconazole, prothioconazole= and propi- conazole.

8. The use acc ording to any one of the precedi ng claims, wherein (E)-5-C4- chlorobenzy Rfidene)-2,2-dimethyl-1-(1H-1,2 4—triazol-1-ylmethyi)cyclope=ntanoi is employed jo intly with at least one further fun=gicide from the group of tte stro- bilurins selected from among trifloxystrobin, goyraclostrobin, orysastrobmin, fluox- astrobin and azoxystrobin.

9. The use acc ording to any one of the precedismng claims, wherein (E)-5-C 4 chlorobenzy lidene)-2,2-dimethyi-1-(1H-1,2,4 -triazol-1-ylmethyl)cyclopentanol is employed jozintly with at least one insecticide= from the group of the pyr azole in- secticides ard the neonictotinoid group. 40 AMENDED SHEET