Use of Arylcarboxylic Acid Biphenylamides for Seed Treatment

A method for protecting plants after germination from the attack of foliar phytopathogenic fungi comprising,

• treating the seed from which the plants are to grow with an effective amount of at least one arylcarboxylic acid biphenylamide of the formula I
• wherein
• X is halogen or methyl;
• n is zero, 1 or 2, wherein when n is 2, the radicals X may have the same or different meanings;
• Y is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy-iminomethyl or allyloxyiminomethyl;
• m is zero to 5, wherein when m is 2, 3, 4 or 5, the radicals Y may have the same or different meanings;
• Ar is an aryl radical of the formula IIa, IIb or IIc
• wherein
• R1 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl,
• R1 is C1-C4-alkyl,
• R2 is hydrogen, halogen or methyl,
• R3 is hydrogen, halogen or C1-C4-alkyl,
• R4 is C1-C4-alkyl or C1-C4-haloalkyl,
• Z is CH or N and
• is halogen, C1-C4-alkyl or C1-C4-haloalkyl
• or an agriculturally acceptable salt thereof.

A seed treatment formulation comprising at least one arylcarboxylic acid biphenylamide of the formula I

• wherein
• X is halogen or methyl;
• n is zero, 1 or 2, wherein when n is 2, the radicals X may have the same or different meanings;
• Y is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy-iminomethyl or allyloxyiminomethyl;
• m is zero to 5, wherein when m is 2, 3, 4 or 5, the radicals Y may have the same or different meanings;
• Ar is an aryl radical of the formula IIa, IIb or IIc
• wherein
• R1 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl,
• R2 is C1-C4-alkyl,
• R3 is hydrogen, halogen or methyl,
• R4 is hydrogen, halogen or C1-C4-alkyl,
• R5 is C1-C4-alkyl or C1-C4-haloalkyl,
• Z is CH or N and
• R6 is halogen, C1-C4-alkyl or C1-C4-haloalkyl
• or an agriculturally acceptable salt thereof, and
• at least one seed treatment auxiliary agent.

A seed comprising at least one arylcarboxylic acid biphenylamide of the formula I

• wherein
• X is halogen or methyl;
• n is zero, 1 or 2, wherein when n is 2, the radicals X may have the same or different meanings;
• Y is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy-iminomethyl or allyloxyiminomethyl;
• m is zero to 5, wherein when m is 2, 3, 4 or 5, the radicals Y may have the same or different meanings;
• Ar is an aryl radical of the formula IIa, IIb or IIc
• wherein
• R1 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl,
• R2 is C1-C4-alkyl,
• R3 is hydrogen, halogen or methyl,
• R4 is hydrogen, halogen or C1-C4-alkyl,
• R5 is C1-C4-alkyl or C1-C4-haloalkyl,
• Z is CH or N and
• R6 is halogen, C1-C4-alkyl or C1-C4-haloalkyl
• or with an agriculturally acceptable salt thereof,
• and optionally at least one fungicidal active ingredient, selected from the group consisting of
• azoles selected from the group consisting of bromoconazole, cyproconazole, difenoconazole, epoxyconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol and triticonazole;
• acylalanines selected from the group consisting of benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl;
• guazatine;
• anilinopyrimidines selected from the group consisting of pyrimethanil, mepanipyrim or cyprodinil;
• dicarboximides selected from the group consisting of iprodione, procymidon and vinclozolin;
• dithiocarbamates selected from the group consisting of mancozeb, metiram and thiram;
• heterocyclic compounds selected from the group consisting of benomyl, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazid, thiabendazol and thiophanate-methyl;
• phenylpyrroles selected from the group consisting of fenpiclonil and fludioxonil;
• other fungicides, for example benthiavalicarb, cyflufenamide, fosetyl, fosetyl-aluminium, phosphoric acid and 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;
• strobilurines such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxa-strobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclo-strobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methyl-benzyloxyimino)-ethyl]-benzyl)-carbamate, methyl (2-chloro-5-[1-(6-methyl-pyridin-2-ylmethoxyimino)-ethyl]-benzyl)-carbamate and 2-ortho-[(2,5-dimethylphenyl-oxymethylen)phenyl]-3-methoxy-acrylate;
• and
• cinnamic acid amides and analogous selected from the group consisting of dimethomorph, flumetover and flumorph,
• and/or at least one insecticidal active ingredient, selected from the group consisting of acetamiprid, alpha-cypermethrin, beta-cypermethrin, bifenthrin, carbofuran, carbosulfan, clothianidin, cycloprothrin, cyfluthrin, cypermethrin, deltamethrin, diflubenzuron, dinotefuran, etofenprox, fenbutatin-oxide, fenpropathrin, fipronil, flucythrinate, imidacloprid, lambda-cyhalothrin, nitenpyram, pheromones, spinosad, teflubenzuron, tefluthrin, terbufos, thiacloprid, thiamethoxam, thiodicarb, tralomethrin, triazamate, zeta-cypermethrin, spirotetramat, flupyrazofos, tolfenpyrad, flubendiamide, bistrifluoron, benclothiaz, pyrafluprole, pyriprole, amidoflumet, flufenerim, cyflumetofen, cyenopyrafen, the anthranilamide compound of formula Γ2
• where B1 is Cl, B2 is Br and RB is CH3,
• and the anthranilamide compound of formula Γ2 where B is CN, B2 is Br and RB is CH3.