MXPA00001332A - Fluoropyrazole-biphenylamide fungicides - Google Patents

Abstract

The invention relates to biphenylamides having general formula (I), and their salts, in which R1 is H or F;R2 is H, halogen, alkyl, halogen methyl, alkoxy, alkylthio;R3 is CH3, CHF2, CF3. The invention also relates to agents containing biphenylamides, the production of biphenylamides and their use in combating parasitic fungus.

Description

"BIFENILAMIDAS" The present invention relates to a biphenylamide of the formula I and the salts thereof, wherein the radicals R1, R2 and R3 have the following meanings: R1 is hydrogen or fluorine; R 2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, halomethyl, in particular, fluoro- or chloro-methyl, such as, for example, trifluoromethyl, trichloromethyl, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4. carbon atoms; R3 is methyl, difluoromethyl or trifluoromethyl. In addition, the invention relates to a process for preparing compounds I, with compositions comprising I and a method for controlling harmful fungi and with the use of compounds I, their salts or compositions for this purpose. Type I fungicidal biphenylamides are disclosed in the following publications: Patent No. 5,438,070, DE-A 24 17 216, EP-A 545 099 and EP-A 589 301. However, all the compounds mentioned in these publications are unsatisfactory with respect to their activity. ~ - An object of the present invention is to provide biphenylamides which have better activity against harmful fungi. We have found that this object is achieved by the compounds I defined in the beginning. In addition, we have found that the compositions comprising the compounds I or salts thereof and a process for preparing I and the compositions. In addition, we have found a method for controlling harmful fungi, and the use of compounds I, their salts or compositions for this purpose. The compounds I are capable of being obtained in a manner known per se from the corresponding acyl halides II and biphenylamines III, with the aid of a base such as, for example, triethanolamine.

II III - Hal is halogen, preferably chlorine or bromine; R is hydrogen, or fluorine; R 2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, halomethyl, in particular fluoro or chloromethyl such as, for example, trifluoromethyl, trichloromethyl, alkoxy of 1 to 4 carbon atoms, or alkylthio of 1 to 4 carbon atoms; R3 is methyl, difluoromethyl or trifluoromethyl. For the reaction conditions for preparing the compounds I and for the origin of the starting materials II, see for example, Patent Number WO 93/11117, pages 17 to 19. The biphenylamines III are generally known or can be obtained from known manner by se (see for example Tetrahedron Letters 28 (1987), 5093-5096). The salts of acid stable compounds I containing basic centers, especially basic nitrogen atoms, and in particular with mineral acid salts such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride, are also part of the subject matter of the present invention. Generally, the salt class does not matter. For the purposes of the invention, preference is given to those salts that do not damage the plants, areas, materials or spaces that are to be kept free of harmful fungi and that do not affect - - detrimentally the activity of the compounds I. Salts of this kind which are suitable for agricultural purposes are particularly important. The salts of the compounds I are capable of being obtained in a manner known per se, such as, in particular, by reacting the corresponding biphenylalides I with the aforementioned acids in water or an inert organic solvent at temperatures from -80 ° C to 1Z0 ° C. from 0 ° C to 60 ° C. The definitions of the compounds I to III that are given at the beginning, used joint terms that are representative of the following substituents: halogen, fluorine, chlorine, bromine and iodine; alkyl: straight or reacted chain alkyl groups having 1 to 4 carbon atoms, for example, alkyl of 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl , 1-ethylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl; alkoxy: straight or branched chain alkyl groups having from 1 to 4 carbon atoms, for example alkoxy of 1 to 3 carbon atoms such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy: alkylthio: alkyl groups of chain straight or branched that have 1 to 4 carbon atoms (as mentioned above) that are bonded to the skeleton through the sulfur atom (-S-), for example methylthio, ethylthio, propylthio, 1-methylethylthio, n-butylthio and tertiary butylthio. With respect to their biological activity against harmful fungi, preference is given to compounds I and wherein R2 is halogen, in particular, fluorine, chlorine or bromine; - alkyl of 1 to 4 carbon atoms, in particular methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; - alkoxy of 1 to 4 carbon atoms, in particular methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; alkylthio, in particular methylthio, ethylthio, n-propylthio or isopropylthio. With respect to its use to control the percutaneous fungi, preference is given, very specific to the compounds I compiled in Table I presented below.

Table I Number Rl R2 R3 1. 1 H H CH3 1. 2 H 3'-CH 3 CH 3 1. 3 H 3'-F CH3 1. 4 H 3'-Cl CH 3 1. 5 H _3'-CH3 CH3 1. 6 H 3 '-0CH3 CH3 1. 7 H 3'-OCH (CH 3) 2 CH 3 1. 8 H 3'-Br CH3 1. 9 H 4'-F CH3 1., if desired using emulsifiers and dispersants. If the diluent used is water, other organic solvents can be used as auxiliary solvents. Suitable auxiliaries are essentially: solvents, such as aromatics (for example xylene), chlorinated aromatics (for example chlorobenzenes), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol), ketones (for example cyclohexanone), amines (for example ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and synthetic ground minerals (e.g. finely divided silica, silicates); emulsifiers, such as non-anionic and anonic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants, such as residual liquids of lignosulfite and methylcellulose. Suitable surfactants are alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example, ligno-, phenol-, naphthalene- and dibutyl-naphthalenesulfonic acid, and of fatty acids, alkylsulfonates and alkylarylsulfonates. , alkyl sulphates, lauryl ether sulfates and fatty alcohol sulfates and salts of the sulfated hexa-, hepta- and octa-decanoles, or the fatty alcohol glycol ethers, sulfonated naphthalene condensates and their derivatives with formaldehyde, naphthalene condensates or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyphenol ether, isooctyl-, octyl- or nonylphenol ethoxylated, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol / ethylene oxide condensates, oil of ethoxylated castor, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, polyether ether acetate licol of lauryl alcohol, sorbitol esters, residual liquids of lignosulfite or methylcellulose. Powders, dispersing materials and fine powders can be prepared by mixing or milling together the active compounds with a solid carrier.

- - Granules, for example coated granules, impregnated granules or homogeneous granules, can be prepared by linking the active compounds with solid carriers. Solid carriers are mineral stones such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, chalk, clay, calcinoferruginous, clay, dolomite, diatomaceous earth, calcium sulfate, sulfate of magnesium, magnesium oxide, ground synthetic materials, and fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of vegetable origin such as cereal flour, tree bark flour, wood flour and nut shell flour, cellulose powder or other solid carriers. Examples of these preparations are: I. a solution of 90 parts by weight of a compound I according to the invention and 10 parts by weight of N-methyl-2-pyrrolidone, which is suitable for use in the form of microdroplets; II. a mixture of 10 parts by weight of a compound I according to the invention, 70 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate, 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil; a dispersion is obtained by distributing finely the solution in water; III. an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct and 40 moles of ethylene oxide to 1 mole of oil of castor; IV: an aqueous dispersion of 10 parts by weight of a compound I according to the invention, 25 parts by weight of cyclohexanol, 55 parts by weight of a petroleum fraction of boiling temperature of 210 ° C to 280 ° C and parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil; V: a mixture, milled in a hammer mill, of 80 parts by weight of a compound I according to the invention, preferably in solid form, 3 parts by weight of sodium diisobutyl naphthalene-2-sulfonate, parts by weight of the sodium salt of a lingosulfonic acid of a residual sulphite liquid and 7 parts by weight of pulverulent silica; a Spraying mixture is obtained by finely distributing the mixture in water; SAW. an intimate mixture of 3 parts by weight of a compound I according to the invention and 97 parts by weight of finely divided kaolin; this fine powder comprises 3 weight percent of the active compound; VITT an intimate mixture of 30 parts by weight of compound I according to the invention, 62 parts by weight of pulverulent silica gel and 8 parts by weight of a paraffin oil which has been sprayed onto the surface of this silica gel; this formulation imparts good adhesion to the active compound; VIII. a stable aqueous dispersion of 40 parts by weight of a compound I according to the invention, 10 parts by weight of the sodium salt of a condensate of phenolsulfonic acid / urea / formaldehyde, 2 parts by weight of silica gel and 48 parts by weight of water, it being possible for this dispersion to be further divided; IX. a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight, - I weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid / urea / formaldehyde condensate and 50 parts by weight of a paraffinic mineral oil. The novel compounds have a remarkable activity against a wide range of phytopathogenic fungi, in particular, of the Deutero ycetes, Ascomycetes, Phycomycetes and Basidiomycetes classes. Some of them act systematically and can be used as foliar fungicides and ground drive. They are especially important for controlling a large number of fungi in a variety of crops, such as wheat, rye, barley, oats, rice, corn, lawns, cotton, soybeans, coffee, sugarcane, vines, fruit species, ornamental and vegetable species for example, cucumbers, beans and cucurbits as well as seeds of these plants. The compounds are applied by treating the fungi, their region where they grow or the plants, areas or materials that are to be kept free thereof with an effective amount of the active compounds. The application is made before or after the infection of the materials, plants or seeds by fungi.

- Specifically, the novel compounds are suitable for controlling the following plant diseases: Erysiphe graminis (powdered powder) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbiters, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in cereals, Rhizoctonia species in cotton and lawns, species, Ustilago in cereals and sugarcane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis cinerea (gray mold) in strawberries, vines, ornamental plants and vegetables, Monilinia species in fruit, Cercospora arachidicola in walnuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, species Fusarium and Verticillium in a variety of plants, Plasmopara viticulture in vines, species Alternaria in legumes and fruits. In general, the fungicidal compositions comprise from 0.1 percent to 95 percent, preferably from 0.5 percent to 90 percent by weight of the active compound. Dependent on the nature of the desired effect, the application regimes are 0.025 to 2 kilograms, 0.1 to 1, kilogram preference of the active compound per hectare. In the treatment of seeds, the amounts of 0. 001 to 50 grams, preferably 0.01 to 10 grams, of the active compound are usually required per kilogram of seed. The novel compounds can also be used in the protection of materials (Wood foot protection), for example against Paecilomyces variotii. The compositions according to the invention in the form of use as fungicides can be present together with other active compounds, eg, with herbicides, insecticides, growth regulators, fungicides or also with fertilizers.In many cases, a mixture with fungicides gives as a result a broader spectrum of fungicidal action The following list of fungicides together with which of the compounds according to the invention can be used, is proposed to illustrate the possible combinations, but not to impose any limitations: sulfur, dithiocarbamates and their derivatives, such as iron dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylenebisdithiocarbamate, zinc manganese ethylene diamine bis-dithiocarbamate, zinc disulfide - tetramethylthiuram, zinc complex (N, N-ethylene-bis-dithiocarbamate), zinc ammonia complex (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bisdithiocarbamate), N, N -polypropylenebis (thiocarba oil) disulfure- nitro derivatives, such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3, 3'-dimethylacrylate, 2-sec-butyl carbonate -4,6-dinitrophenylisopropyl, diisopropyl-5-nitroisophthalate; heterocyclic substances, such as acetate 2-heptadecyl-2-imidazoline, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethylphtali idhophosphonothialate, 5-amino-l- [bis (dimethylamino) -phosphinyl] -3- phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4, 5-b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazolcarbamate methyl, 2-methoxycarbonylaminobenzyl imidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benzimidazole, N- (1,1, 2,2, -tetrachloroethylthio) tetrahydroftali ida, N-trichloromethyl thiotetrahydroftalimide , N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulphuric diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2, 5 -diraethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, 1-pyridin-2-thione oxide, 8-hydroxyquinoline - or its copper salt, 2, 3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiane, 2,3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiaine-4, 4- dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methyl-furan-3-carboxanilide, 2,5-dimethyl-purap-3-carboxanilide, 2,4,5-trimethyl-furan-3-carboxanilide, N-cyclohexyl-2,5-dimethyl-furan-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2, 2, 2-trichloroethyl acetal, piperazine-1, -diylbis-1- (2, 2, 2-trichloroethyl) formamide, 1- (3,4-dichloroanilino) -l-formylamino-2,2,2-trichloroethane, 2 , 6-dimethyl-N-tridecyl-morpholine_ or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2, 6 -dimethylmorpholine, N- [3- (p-tert-butylphenyl) -2-methyl-propyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-l, 3-dioxolan-2-ylethyl ] -1H-1, 2,4-triazole, 1- [2- (2,4-dichloro-phenyl) -4-n-propyl-l, 3-dioxolan-2-ylethyl] -1H-1, 2, 4-triazole, N- (n-propi l) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazolylurea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) ) -2-butanone, (2-chlorophenyl) - (4-chlorophenyl) -5-pyrimidine-methanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis (p-chlorophenyl) -3-pyridinemethanol , 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2-thioureido) -benzene, [2- (4-chlorophenyl) ethyl] - (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol, 1- [3- (2-chlorophenyl) -1- (4-fluorophenyl) -oxiran-2-ylmethyl] -1H-1, 2,4-triazole, and a variety of fungicides, such as dodecylguanidine acetate, 3- [3- (3, 5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, N- (2,6-dimethylphenyl) -N- (2-furoyl) -DL-alaninate methyl, DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) -alanine in methyl ester, N - (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine in methyl ester, 5-methyl-5- vinyl-3- (3, 5-dichlorophenyl) -2,4-dioxo-l, 3-oxazolidine, 3- (3,5-dichlorophenyl) -5-methyl-5-methoxymethyl-l, 3-oxazolidine-2, 4-dione, 3- (3,5-dichlorophenyl) -1-iso-propylcarba oilhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano- [N-] (ethylaminocarbonyl) -2-methoximino] -acetamide, 1- [2- (2,4-dichlorophenyl) entyl] -1H-1,2,4-triazole, 2,4-difluoro-alpha- (1H-1) alcohol , 2, 4-triazolyl-1-methyl) benzhydryl, N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoro-methyl-3-chloro-2-aminopyridine, 1- ((bis- (4 -fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole. strobilurins, such as methyl E-methoximino- [alpha- (o-tolyloxy) -o-tolyl] acetate, E-2-. { 2- [6- (2-cyanophenoxy) iridimin-4-yl-oxy] phenyl} -3-methoxyacrylate methyl, N-methyl-E-methoxyimino- [alpha- (2,5-dimethyloxy [sic.].) -o-tolyl] acetamide. The anilinopyrimidines, such as N- (4,6-dimethylpyrimidin-2-yl) -aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl- 6-cyclopropyl-pyrimidin-2-yl) aniline. Phenylpyrroles, such as 4- (2, 2-difluoro-1,3-benzodioxol-4-yl) -pyrrole-3-carbonitrile. The cinnamamides, such as 3- (4-chlorophenyl) -3- (3, -dimethoxyphenyl) -acyloyl orfolide.

Synthesis Examples The procedures for preparing the compounds I and III that are provided in the synthesis examples given below can be used to obtain further representatives of the formula I or III by modification of the starting materials. Some of the physical data of the products prepared in this way are also provided in Tables 2 and 3, which will be given below.

Example 1 (intermediate of type III) 2-Amino-5, 4'-difluorobiphenyl (number 2.3 in Table 2) Under nitrogen, a solution of 2.4 grams of tetrakis (triphenylphosphine) palladium, 15.1 grams (0.108 mole) of 4-fluorophenylboronic acid and a solution of 30 grams (0.282 mole of sodium carbonate in 120 milliliters of water to a solution) were added to a solution. of 11.4 grams (0.060 mole) of 2-bromo-4-fluoroaniline in 120 milliliters of 1,2-dimethoxyethane, and the mixture was heated to reflux for 8 hours, after cooling, 200 milliliters of tertiary butyl ether were added. methyl and 100 milliliters of water The organic phase was washed with water, dried and concentrated, chromatography of the residue through 50 grams of silica gel using cyclohexane as the eluent gave 12.4 grams of the title compound ( melting: 67 ° C to 69 ° C).

Table 2 Number RJ R Fusing Temperature [° C] 2. 1 5-F H Oil 2.2 5-F 4'-Cl 75-80 2. 3 5-F 4'-F 67-69 2. 4 5-F 4'-CH3 73-76 2. 5 3-F H 2. 6 3-F 4T-C1 2. 7 3-F 4'-F 2.8 3-F 4'-CH3 2. 9 4-F H 2.10 * 4-F 4'-F 2.11 4-F 4 * -Cl 2. 12 4-F 4'-CH3 2.13 6-F H 2.14 6-F 4'-F 2.15 6-F 4'-Cl 2.16 6.F 4'-CH3 * Alternative synthesis: reduction of the corresponding nitro compound (see Chem. Ber. 64 (1931), page 1332 ff., J. Chem. Soc. (1930), page 1159 ff_; Chem. Ber. 61 (1928), page 1407 ff.) Example 2 (active compound of type I) N- (4'-chlorobiphenyl) -1,3-dimethyl-5-fluoropyrazole-4-carboxamide A + 5 ° C, a solution of 1.15 grams (7 millimoles) of 1,3-dimethyl-5-fluoropyrazole- 4-carbonyl in 3 milliliters of tetrahydrofuran was added dropwise to a solution of 1.42 grams (7 millimoles) of 2-amino-4'-chlorobiphenyl and 0.71 gram (7 millimoles) of triethylamine in 7 milliliters of tetrahydrofuran, and then mixing it was stirred for 20 minutes at + 5 ° C and for 2 hours at room temperature. The mixture is stirred in 140 milliliters of water and the precipitated material is filtered by suction. Digestion with a mixture of ether, diisopropyl and cyclohexane (1: 2) yielded 1.5 grams of the header compound (melting point: 146 ° C-150 ° C, number 1.10 in the table below).

Table [lacuna] (I) Number R R2 R ~ Melting Temperature [° C! 1. 1 H H CH3 147 - 150 1. 9 H 4'-F CH3 138 - 139 1. 10 H 4'-Cl CH3 -135-139 1. 11 H 4'-CH 3 CH 3 113 - 114 1. 59 H 4'-F CF3 - 1. 60 H '4'-Cl CF3 - 1. 61 H 4'-CH 3 CF 3 (- 1 t Examples of use - - The following tests of the fungicidal activity of the compounds I were carried out using an emulsion consisting of 10 weight percent of the active compound and 90 weight percent of a mixture of 70% by weight of cyclohexane1 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, alcohol-based emulsifier fatty acids).

The concentrations of the desired active compound were obtained by diluting this emulsion with water. The 2 t Ethyl-2-chloronicotinanilide served as a comparison compound "A", the 2'-phenyl-2-chloronicotinanilide served as the comparison compound "B". Both compounds are given by conox in Patent Number DE-A-24 17 216. " Example 1 of use Botrytis cinerea - - The fruit discs of green peppers were sprayed to run with the aqueous preparation that had been prepared according to the above procedure and each consisted of 250 parts per million of a single active compound. The active compound used was compound 1.10 according to the invention. 2 Hours after the spray coating had dried, the fruit discs were inoculated with a spore suspension of the Botrytis cinerea fungus containing 1.7 x 106 spores per milliliter of a Bio alz solution of 2 percent concentration. The fruit discs were subsequently incubated for 4 days at 18 ° C in chambers of high atmospheric humidity. The visual classification showed a fungal infection of 0 percent to 15 percent of the disk surface for the compound mentioned above. In the case of compound "A", the fungal infection, under otherwise identical test conditions, was 100 percent. Discs that had not been treated with a compound I or compound "A" showed 100 percent infection.

Example 2 of use Erysiphe graminis var. tritici The leaves of the wheat shoots (cv. "Frühgold") that had been grown in pots were sprayed with an aqueous preparation that had been prepared according to the previous procedure which consisted in each case of 250 parts per million of a single active compound The active compound used was compound 1.10 according to the invention, or 24 hours after the coating had dried by spraying, the leaves were sprinkled with oidia (spores) of wheat blight (Erysiphe graminis var. Tritici). The plants were subsequently incubated for 7 days at a temperature of 20 ° C-22 ° C and a relative atmospheric humidity of 75 percent to 80 percent. The visual classification showed a fungal infection of 5 percent to 25 percent of the leaf surface for the aforementioned compound. In the case of compound "A", the fungal infection, under otherwise identical test conditions, was 60 percent. An infection of 80 percent was determined for "B". Leaves that had not been treated with compound I, * B 'showed 80 percent infection.

Claims (6)

1. CLAIMS: A biphenylamide of the formula I and the salts thereof, wherein the radicals R *, R2 and R3 have the following meanings: R1 is hydrogen or fluorine; R2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, halomethyl, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms; R3 is methyl, difluoromethyl or trifluoromethyl.
2. 2. A process for preparing biphenylsides of the formula I according to claim 1, which comprises reacting an acyl halide of the formula in which Hal is halogen, with an inlet of the formula III with the help of a base.
3. 3. A composition suitable for controlling harmful fungi, comprising an effective amount of at least one compound of the formula I or a salt thereof according to claim 1, and at least one auxiliary of the customary formulation.
4. 4. A process for preparing the composition according to claim 3, which comprises processing together, in a manner known per se, a fungicidally effective amount of at least one compound of the formula I or a salt thereof in accordance with claim 1, with at least one auxiliary of the customary formulation.
5. A method for controlling harmful fungi comprising treating the deleterious fungi, their region where they grow or the plants, spaces, areas or "materials to be kept free of them with an effective amount of at least one compound of the formula I or a salt thereof according to claim 1, or with a composition comprising I or a salt thereof according to claim 3. '
6. 6. The use of the compound of the formula I or a salt thereof according to claim 1, or of the composition according to claim 3 for controlling harmful fungi.