WO2007071656A1

WO2007071656A1 - Method for controlling rusting in leguminous plants

Info

Publication number: WO2007071656A1
Application number: PCT/EP2006/069864
Authority: WO
Inventors: Jochen Dietz; Siegfried Strathmann; Thomas Grote; Reinhard Stierl
Original assignee: Basf Aktiengesellschaft
Priority date: 2005-12-20
Filing date: 2006-12-18
Publication date: 2007-06-28

Abstract

Disclosed are a method for controlling rusting in leguminous plants by utilizing pyrazolyl carboxylic acid anilides of formula (I), wherein R1 = H, halogen, CH3, or C1-C2 alkyl halide; R2 = H, F, Cl, or CH3; R3 = F, Cl, CH3, C1-C2 alkyl halide, -CH=N-OR5, or -C(CH3)=N-OR5; R4 = H, F, Cl, CH3, or C1-C2 alkyl halide; R5 = H, CH3, or C2H5; mixtures of pyrazolyl carboxylic acid anilides of formula (I) and a fungicidal agent II from the group comprising azoles, acylalanines, amine derivatives, anilinopyrimidines, dicarboximides, dithiocarbamates, heterocylic compounds, phenylpyrroles, cinnamamides, and analogs, or other active substances according to the description. Also disclosed are agents and seeds containing said mixtures.

Description

Method of controlling rust in legume

description

The invention relates to a method for controlling rust attack in legumes.

Until recently, there was hardly any infestation of harmful fungi in the most important legume production areas (especially soya), which was of economic importance. In recent years, however, there has been an increase in soybean rust in South America due to the harmful fungi Phakopsora pachyrhizi and Phakopsora meibomiae. There were considerable crop and yield losses.

Most common fungicides are not suitable for controlling rust in soybeans or their action against the rust fungus is unsatisfactory.

Surprisingly, it has now been found that pyrazolylcarboxylic anilides of the formula I

in which the substituents have the following meanings: R ^{1 is} hydrogen, halogen, methyl or C ₁ -C ₂ -haloalkyl;

R ^{2 is} hydrogen, fluorine, chlorine or methyl;

R ^{3 is} fluorine, chlorine, methyl, C ₁ -C ₂ -haloalkyl, -CH = N-OR ⁵ or -C (CH ₃ ) = N-OR ⁵ , where R ^{5 is} hydrogen, methyl or ethyl;

R ^{4 is} hydrogen, fluorine, chlorine, methyl or C ₁ -C ₂ -haloalkyl;

are extremely effective against rust fungus diseases of legumes.

The pyrazolylcarboxylic anilides I are e.g. from EP-A 589 301, WO 03/70705, WO 2004/103975, WO 2005/34628 and WO 2006/092213 or can be prepared in the manner described therein.

The active substances described as mixing partners in the present invention are generally known to the person skilled in the art (cf., http://www.hclrss.demon.co.uk/) and are commercially available. In formula I, C 1 -C 2 -haloalkyl represents a partially or completely halogenated C 1 -C 2 -alkyl radical, where the halogen atom (s) is / are in particular fluorine and / or chlorine, ie, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl , Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-ethyl, 2-bromo-2,2 -difluoroethyl, 1, 1, 2,2-tetrafluoroethyl, 1, 1, 2-trifluoro-2-chloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2 fluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl or pentafluoroethyl, in particular for halomethyl, more preferably CH ₂ -CI, CH (Cl) ₂ , CH ₂ -F, CH (F) ₂ , CF ₃ , CHFCI, CF ₂ CI or CF (CI) ₂ .

Particularly preferred are those compounds I in which the variables follow

Meanings, both on their own and in any combination with each other:

R ^{1 is} methyl or C ₁ -C ₂ -haloalkyl, in particular methyl or halomethyl, particularly preferably methyl, CHF ₂ or CF ₃ ;

R ^{2 is} hydrogen or fluorine, in particular hydrogen;

R ^{3 is} fluorine, chlorine or methyl, in particular fluorine or chlorine; most preferably chlorine;

R ^{4 is} hydrogen, fluorine or chlorine, in particular hydrogen or chlorine.

Also particularly preferred are the pyrazolylcarboxylic anilides of the formula Ia

in particular the compounds listed in the following Table A):

Table A)

Furthermore, anilides of the formula Ib

in particular the compounds listed in the following Table B):

Table B)

Also particularly preferred are the pyrazolylcarboxylic anilides of the formula Ic

in particular the compounds listed in the following Table C):

Table C)

Very particular preference is given to the following compounds I: 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-3-fluoro-biphenyl-2-yl) -amide,

1-Methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-3-fluoro-biphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole 4-carboxylic acid (3 ', 4'-difluoro-3-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-difluoro-3-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3'-chloro-4'-fluoro-3-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide,

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-difluoro-4-fluoro-biphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole 4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-difluoro-4-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3'-chloro-4'-fluoro-4-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide,

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-difluoro-5-fluoro-biphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole 4-carboxylic acid (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-difluoro-5-fluoro-biphenyl-2-yl) -amide,

1, 3-Dimethyl-1H-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4 -carboxylic acid (3'-chloro-4'-fluoro-5-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-fluoro-4-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-fluoro-5-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chloro-5-fluoro-biphenyl-2-yl) -amide,

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-methyl-5-fluorobiphenyl-2-yl) -amide,

1, 3-Dimethyl-1H-pyrazole-4-carboxylic acid (4'-fluoro-5-fluoro-biphenyl-2-yl) -amide,

1, 3-Dimethyl-1H-pyrazole-4-carboxylic acid (4'-chloro-5-fluorobiphenyl-2-yl) -amide, 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid (4 ' methyl-5-fluoro-biphenyl-2-yl) -amide,

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-fluoro-6-fluoro-biphenyl-2-yl) -amide and 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chloro-6-fluoro-biphenyl-2-yl) -amide.

A significant increase in activity in the process according to the invention is achieved by the combined use of a Heterocyclylcarbonsäureanilids I with at least one active ingredient II from the following group in synergistically effective amounts:

Azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazole, prothioconazole, tebuconazole, tetraconazole,

Triadimefon, Triadimenol, Triticonazole,

Acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl,

• amine derivatives such as guazatine,

Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil, dicarboximides such as iprodione, procymidone, vinclozolin,

Dithiocarbamates such as Mancozeb, Metiram, Thiram,

Heterocyclic compounds such as benomyl, boscalid, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazide, thiabendazole, thiophanate-methyl, phenylpyrroles such as fenpiclonil or fludioxonil,

Other fungicides such as benthiavalicarb, cyflufenamid, fosetyl, fosetyl-aluminum, phosphorous acid or its salts, iprovalicarb, metrafenone and 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6 trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine,

• strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxazirbin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrinbin, trifloxystrobin, (2-chloro-5- [1 - (3-methyl-benzyloxyimino) -ethyl ] benzyl) - carbamic acid methyl ester, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester and 2-ortho - [(2,5-dimethylphenyl oxymethylene ) phenyl] -3-methoxy-methyl acrylate; Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.

It has been found that, with simultaneous simultaneous or separate application of a Pyrazolylcarbonsäureanilids I and at least one compound II or when using a Pyrazolylcarbonsäureanilids I and an active ingredient Il consecutive rust attack in legumes can fight even better than with the individual compounds (synergistic mixtures).

The invention therefore also relates to fungicidal mixtures for controlling rust fungi, containing as active components A) a Pyrazolylcarbonsäureanilid I, and

B) an active ingredient II as defined above in synergistically effective amounts.

The pyrazolylcarboxylic acid anilide I and the active compound II can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally having no effect on the control result. The control of harmful fungi takes place by application of the pyrazolylcarboxylic acid anilides I by seed treatment, spraying or dusting of the plants or the soil before or after sowing of the plants, or before or after emergence of the plants.

The control of rust diseases in legumes is advantageously carried out by the application of an aqueous treatment of a formulation containing a Pyrazolylcarbonsäureanilid I on the above-ground parts of plants, especially the leaves, or, as prophylaxis due to the high systemic effect, by seed or soil treatment done.

The compounds I and II are usually employed in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 10: 1 to 1:10.

The Pyrazolylcarbonsäureanilids I can be used in the process according to the invention advantageously together with other active ingredients IM, in addition to the active ingredients II also with herbicides, insecticides, growth regulators, other fungicides or with fertilizers. Particularly suitable as these further mixing partners IM are: imazethapyr, imazamox, imazapyr, imazapic, or dimethenamid-p;

Fipronil, Imidacloprid, Acetamipird, Nitenpyram, Carbofuran, Carbosulfan, Benfurabarb, Thiacloprid, Clothianidin, MTI 446 and CGA 293343.

The compounds I and IM are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 10: 1 to 1:10 applied.

The above-described mixtures of a pyrazolylcarboxylic anilide I with herbicides are used in particular in crops in which the plants have a reduced sensitivity to them, in particular the imidazolinone active ingredients.

The use of pyrazolylcarboxylic anilides I in soybeans has led to a significant increase in yield. The application of the pyrazolylcarboxylic anilides I can thus also be carried out for the purpose of increasing the yield. The increase in yield in combination with the excellent effect of pyrazolylcarboxylic acid Nilides I against rust diseases in legumes makes the process according to the invention valuable for the farmer. Excellent results can be achieved by using a Pyrazolylcarbonsäureanilids I in combination with an active ingredient II.

Furthermore, with the method according to the invention, other harmful fungi, which frequently occur in legumes, can be combated very well. The main fungal diseases in soy are the following:

• Microsphaera diffusa • Cercospora kikuchi

• Cercospora sojina

• Septoria glycines

Colletotrichum truncatum

The pyrazolylcarboxylic anilides I and the above-described mixtures of I and II are also suitable for controlling the above-mentioned. Diseases.

The pyrazolylcarboxylic anilides I or the mixtures of I and II are used by treating the fungi or the plants, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active compounds. The application can take place both before and after the infection of the materials or plants by the fungi. The treatment preferably takes place before the infection.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.

When using a Pyrazolylcarbonsäureanilids I alone, the application rates in the process according to the invention, depending on the nature of the desired effect between 0.01 and 1, 5 kg of active ingredient per ha.

In the seed treatment are generally required drug amounts of 1 to 1500 g of Pyrazolylcarbonsäureanilid I, preferably 10 to 500 g, per 100 kilograms of seed.

The application rates of the mixtures according to the invention are, depending on the nature of the active compound II and the desired effect at 10 g / ha to 2500 g / ha, preferably 50 to 2000 g / ha, in particular 100 to 1500 g / ha. When applying the mixtures, the application rates for the pyrazolylcarboxylic acid anilide I are accordingly 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 active compound II are accordingly generally 1 to 1500 g / ha, preferably 10 to 1250 g / ha, in particular 20 to 1000 g / ha.

In seed treatment, application rates of mixture of 1 to 2000 g / 100 kg of seed, preferably 1 to 1500 g / 100 kg, in particular 5 to 1000 g / 100 kg, are generally used.

For use in the process of the invention, the compounds may be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, e.g. by stretching the active compound with solvents and / or excipients, if desired with use of emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:

- water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), Acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.

In principle, solvent mixtures can also be used

Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin

Sulfite liquors and methylcellulose.

The surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene glycol octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, tristerylphenyl polyglycol ethers, alkyl arylpolyether alcohols, alcohol and fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulphite liquors and methylcellulose.

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, there are mineral oil fractions of medium to high boiling point, such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

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

A) Water Soluble Concentrates (SL)

10 parts by weight of a compound according to the invention are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with an active ingredient content of 10% by weight. B) Dispersible Concentrates (DC)

20 parts by weight of a compound according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion. The active ingredient content is 20% by weight

C) Emulsifiable Concentrates (EC)

15 parts by weight of a compound according to the invention 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 in water results in an emulsion. The formulation has an active ingredient content of 15% by weight.

D) Emulsions (EW, EO)

25 parts by weight of a compound according to the invention 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 water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.

E) suspensions (SC, OD)

20 parts by weight of a compound according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine Wirkstoffsuspension sion. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.

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

50 parts by weight of a compound according to the invention are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The formulation has an active ingredient content of 50% by weight.

G) Water-dispersible and water-soluble powders (WP, SP)

75 parts by weight of a compound according to the invention are ground with the addition of 25 parts by weight of dispersants and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight. 2. Products for direct application

H) dusts (DP)

5 parts by weight of a compound according to the invention are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with an active ingredient content of 5 wt .-%.

J) Granules (GR, FG, GG, MG)

0.5 parts by weight of a compound according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.

K) ULV solutions (UL) 10 parts by weight of a compound of the invention are dissolved in 90 parts by weight of an organic solvent e.g. XyIoI solved. This gives a product for direct application with an active ingredient content of 10 wt .-%.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring. The forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable 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 wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.

To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.

applications

The active compounds were prepared separately or together as a stock solution with 25 mg Pyrazolylcarbonsäureanilid I, which with a mixture of acetone and / or dimethyl sulfoxide (DMSO) and the emulsifier Wettol ^® EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in Volume ratio of solvent-emulsifier of 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the concentration of active substance indicated below.

1) Curative efficacy against soybean rust caused by Phakopsora pachyrhizi

Leaves of potted "Oxford" soybean seedlings were inoculated with a spore suspension of soybean rust (Phakpsora pachyrhizi) and then placed in a high humidity chamber (90-95%) and 23-27 ° C for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue.The infected plants were sprayed to drip point after 3 days with the above-described active ingredient solution in the concentration of active compound specified below

Test plants in the greenhouse at temperatures between 23 and 27 ° C and 60 to 80% relative humidity cultured for 14 days. Then the extent of rust fungus development on the leaves was determined. While the untreated plants had 95% infestation, no soybean rust (0% infestation) developed on the plants treated with 63 ppm of the compound lc.24 and on the plants treated with 250 ppm of the compound No. lc.7.

The plants treated with 250 ppm of Compound No. 1a.21 were 15% infested, the plants treated with 250 ppm of Compound No. lc.20 5%, and the plants treated with 250 ppm Compound No. lc.38 3% and the plants treated with 250 ppm of compound no. Lc.43 to 20%. 2) pickling test for action against soybean rust

Seeds of soybean BRS 133 were treated with 1000 g of a pyrazolecarboxylic acid anilide I / 100 kg of seed, formulated as SC with 250 g of active ingredient per liter, as wet-sponges, then seeded in pots and cultivated in a greenhouse at ca. 22 ° C. 3 weeks after sowing, the plants were inoculated with soybean rust, for 24 hours at 100% rel. Humidity incubated and then cultivated again in the greenhouse. At the time of inoculation, the first pair of leaves and a follow-up blade were developed. 1 1 days after the inoculation, the infestation of the leaves was evaluated.

3) Root uptake and biological activity against Phakopsora pachyrhizi on soybean

By dissolving the active ingredient in DMSO, a stock solution of 10,000 ppm was prepared. The stock solution was diluted with water to the concentrations to be tested. The concentrations used are in g a.i. given per 100 kg of seed. 1 ml of the respective solution was pipetted into vermiculite soybean seedlings. Seven days after application of the treatments, the soybean plants were inoculated with a spore suspension of Phakopsora pachyrhizi. After an incubation period of 14 days, the first pair of leaves were scored (% infected leaf area).

While the leaf areas of the untreated plants were 100% infected, the plants treated with 250 g of Compound No. Ic.24 per 100 kg seed showed only 17% infected leaf area. After treatment with 125 g of Compound No. Ic.24 per 100 kg of seed, the plants had 53% of infected leaf area.

4) Biological activity against Phakopsora pachyrhizi on soybean as a seed treatment

By dissolving the active ingredient in DMSO, a stock solution of 10,000 ppm was prepared. The stock solution was diluted with water to the concentrations to be tested. The concentrations used are given in grams per 100 kg of seed. 1 ml of the respective solution was pipetted into vermiculite soybeans. 14 days after sowing or after application of the treatments, the soybean plants were inoculated with a spore suspension of Phakopsora pachyrhizi. After an incubation period of 14 days, the first pair of leaves were scored (% infected leaf area). While the leaf area of the untreated plants was 83% infected, the leaves of those plants whose seeds had been treated with 250 g of compound No. Ia.24 per 100 kg of seed had no infestation.

Claims

claims

1. A method for controlling rust attack in legumes, characterized in that the plants, the seeds or the soil by spraying or dusting with a fungicidally effective amount of a Pyrazolylcarbonsäure- anilide of the formula I.

in which the substituents have the following meanings: R ^{1 is} hydrogen, halogen, methyl or C ¹ -C ² -haloalkyl; R ^{2 is} hydrogen, fluorine, chlorine or methyl;

R ^{3 is} fluorine, chlorine, methyl, C ₁ -C ₂ -haloalkyl, -CH = N-OR ⁵ or -C (CH ₃ ) = N-OR ⁵ ; wherein R ^{5 is} hydrogen, methyl or ethyl; R ^{4 is} hydrogen, fluorine, chlorine, methyl or C 1 -C ² -haloalkyl;

be treated.

2. The method according to claim 1, characterized in that R ^{1 is} methyl or Ci-C2-haloalkyl.

3. The method according to claim 1, characterized in that R ^{2 is} hydrogen or fluorine.

4. The method according to claim 1, characterized in that R ^{3 is} fluorine, chlorine or methyl.

5. The method according to claim 1, characterized in that R ^{4 is} hydrogen, fluorine or chlorine.

6. The method according to claim 1, characterized in that an aqueous preparation of a formulation containing a Pyrazolylcarbonsäureanilid I is applied to the above-ground parts of plants.

7. The method according to claim 1, characterized in that the rust attack is controlled by seed treatment or soil treatment.

8. The method according to any one of claims 1 to 7, characterized in that the harmful fungi Phakopsora pachyrhizi or Phakopsora meibomiae are combated.

9. The method according to any one of claims 1 to 7, characterized in that a combination of a Pyrazolylcarbonsäureanilid I is used with at least one commercial fungicide.

10. The method according to any one of claims 1 to 7, characterized in that a combination of a Pyrazolylcarbonsäureanilid I with at least one

Active ingredient II selected from the following group is used:

Azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluconconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobananil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimol, triticonazole,

Acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl,

• amine derivatives such as guazatine,

Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,

Dicarboximides such as iprodione, procymidone, vinclozoline, dithiocarbamates such as mancozeb, metiram, thiram,

Heterocyclic compounds such as benomyl, boscalid, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazide, thiabendazole, thiophanate-methyl,

• phenylpyrroles such as fenpiclonil or fludioxonil, • other fungicides such as benthiavalicarb, cyflufenamid, fosetyl, fosetyl

Aluminum, phosphorous acid or its salts, iprovalicarb, metrafenone and 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1, 5-a] pyrimidine,

Strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,

Picoxystrobin, pyraclostrobin, trifloxystrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1- (6-methylpyridine-2 -ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester and 2-ortho - [(2,5-dimethylphenyl-oxymethylene) -phenyl] -3-methoxy-acrylic acid methyl ester;

Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.

1 1. A method according to any one of claims 1 to 7, characterized in that a combination of Pyrazolylcarbonsäureanilid I with at least one commercially available herbicide, which is tolerant to legumes, is used.

12. The method according to any one of claims 1 to 7, characterized in that a combination of Pyrazolylcarbonsäureanilid I is used with at least one commercially available insecticide.

13. The method according to any one of claims 1 to 7, characterized in that a combination of Pyrazolylcarbonsäureanilid I is used with at least one active ingredient selected from the following group:

Imazethapyr, imazamox, imazapyr, imazapic, and dimethenamid-p;

Fipronil, Imidacloprid, Acetamipird, Nitenpyram, Carbofuran, Carbosulfan, Benfuracarb, Thiacloprid, Clothianidin, MTI 446 and CGA 293343.

14. The method according to claims 9 to 13, characterized in that the Pyrazolylcarbonsäureanilid I and the second active ingredient at the same time, in common or separately, or sequentially ausbringt.

15. The method according to claims 9 to 13, characterized in that one expends the mixture according to claims 9 to 13 in an amount of 5 g / ha to 2500 g / ha.

16. Fungicidal mixtures for controlling rust fungi, containing as active components

A) a Pyrazolylcarbonsäureanilid I according to claim 1, and

B) at least one further active ingredient II according to claim 9 or 10 in synergistically effective amounts.

17. Fungicidal mixtures according to claim 16, containing as active ingredient II an azole according to claim 10.

18. Fungicidal mixtures according to claim 16 or 17, comprising a pyrazolylcarboxylic anilide I and the active ingredient II in a weight ratio of 100: 1 to 1: 100.

19. Fungicidal mixtures containing as active components A) a Pyrazolylcarbonsäureanilid I according to claim 1, and B) Imazethapyr, Imazamox, Imazapyr, Imazapic, or Dimethenamid-p in a weight ratio of 100: 1 to 1: 100.

20. A composition containing a liquid or solid carrier and a mixture according to any one of claims 16 to 19.

21. The method according to any one of claims 1 to 5, characterized in that one applies a Pyrazolylcarbonsäureanilid I according to claim 1 or a mixture according to claims 9 to 13 in an amount of 1 to 2000 g / 100 kg of seed.

22. Seed containing the mixture according to any one of claims 16 to 19 in an amount of 1 to 2000 g / 100 kg.

23. Use of at least one Pyrazolylcarbonsäureanilid I according to claim 1 and, if desired, a further active ingredient according to claims

9 to 13 for the preparation of an agent suitable for combating rust in legumes.