Indian Patents. 224838:A SYNERGISTIC FUNGICIDAL MIXTURE OF PHENYLACETIC ACID DERIVATIVES AND RHIZOCTONIA FUNGICIDES

Title of Invention	A SYNERGISTIC FUNGICIDAL MIXTURE OF PHENYLACETIC ACID DERIVATIVES AND RHIZOCTONIA FUNGICIDES
Abstract	ABSTRACT IN/PCT/2000/00535/CHE A synergistic fungicidal mixture of phenylacetic acid derivatives and Rhizoctonia fungicides A synergestic fungicidal mixture, comprising as active components a) phenylacetic acid derivatives of the formula I in which the substituents are as described in the description. b) at least one compound of the formula II to VII in a synergistically active amount.

Full Text	The present invention relates to fungiC1dal mixtures for controlling harmful fungi, comprising a) phenylaC6tic aC1d derivatives of the formula I in which the substituents and the index have the following meaning: X is HOCH3, CHOCH3 or CHCH3; Y is oxygen or NR; R1, R independently of one another are each hydrogen or C1-C4-allcyl; Ra is cyano, nitro, trifluoromethyl, halogen, C1-C^-alkyl or C1-C4-alkoxy; m is 0, 1 or 2, where the radicals R2 may be different if m is 2; R3 is hydrogen, cyano, C1-C^alkyl, C1-c4-haloalkyl or C3-C6-cycloalkyl; R4, R6 independently of one another are each hydrogen, are C1-C1o-alkyl, C3-C6-cycloalkyl, C2-C1o-alkenyl, C1-C1o-al^ynyl, C1-C1o-alkylcarbonyl, Cz-C1o-alkenyl-carbonyl, C3-C1o-alkynylcarbonyl or C1-C1o-alkyl-sulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto. amino, carboxyl, aminocarbonyl, aminothiocarbony1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl-sulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-Cfi-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, Ca-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino¬carbonyl, aminothiocarbony1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, Cx-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-Cfi-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkyl-thio, C1-Cfi-alkylamino, di-C1-C6-alkylamino, Cx-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothio-carbonyl, C1-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C{»NOR7>-An-RB; are aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetaryl-carbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothio¬carbony 1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-c6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C1-halo-alkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkyl-aminathiocarbonyl, di-C1-C«-alkylaminothiocarbonylf C1-Cs-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C {=N0R7)-Aj,-R8; R5 is hydrogen, is C1-Cfi-alkyl, C1-C6-alkenyl, C2-C«-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto. amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, di-C1-c«~alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkyl-aminotfC1ocarbonyl, C1-Cs-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1.-C6-alkoxy-carbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, Ca-Cs-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-c4-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C^-alkoxy, hetarylthio, hetaryl-C1-C^-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3C6-cycloalkyl [sic], C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-Cfi-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-Cft-alkylamino-carbony1, di-C1-Cfi-alkylaminac&rbony 1, C1-C6-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C{=NOR7)-An-R8; is Ca-C6-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothio¬carbonyl, halogen, C1-C6-alkyl, C1-Cfi-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, Ca-C6-cyclo-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-carbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-Cs-alkylaminocarbonyl, C1-C6-alkylaminothio-carbonyl, di-C1-C6-alkylaminothiocarbonyl, Ca-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C^-alkyl; n is 0 or 1; R7 is hydrogen or C1-C6-allcyl and R8 is hydrogen or C1-C6-alkyl, and their salts, and b) at least one fungiC1de selected from fungiC1des of the formulae II to VII It is an object of the present invention to provide fungiC1dal mixtures having good fungiC1dal activity, in particular against fungal diseases in riC6, exC6eding the activity of the mixture components on their own. We have found that this object is achieved by the mixtures as claimed in claim 1. The compounds of the formula I are known per se and are described in the literature (WO 97/15552). The fungiC1des of the formulae II to VII are also known and described in the literature. In addition, they axe commerC1ally available under the trade names mentioned below in brackets: II: DE-A 27 32 257, common name: pencycuron III:JP 01/104,514, common name: flutolanil (trade name: Moncut, from Ninon Noyaku); IV: US 3,937,840, common name: mepronil (trade name: Basitac®, from Kumiai); V: common name; thifluzamide (trade name: Greatam®, from Monsanto); VI: GB-A 1,312,536, OS 3,755,350; common name: iprodione (trade name: Rovral®, from Rhone-Poulenc); VII: AG Chem New Compound Review, Vol. 15 (1997), 50; common name: furametpyr (trade name: Limber®, from Sumitomo). Owing to their C=C and C=N double bonds, the preparation of the compounds I may yield E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, for example by crystallization or chromatography. However, if the synthesis yields isomer mixtures, a separation is generally not neC6ssarily required sinC6 in some cases the individual isomers can be converted into one another during the preparation for use or upon use (for example under the action of light, aC1ds or bases). Similar conversions may also occur after the use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled. With regard to the C=X double bond, preferenC6 is given to the E isomers of the compounds I (configuration based on the -0CH3 or the -CH3 group in relation to the -CO2R1 group) with respect to their activity. With regard to the -C(R3)»NOCH2- double bond, preferenC6 is given to the C1s isomers of the compounds I (configuration based on the radical R3 in relation to the -OCH2- group) with respect to their activity. In the definitions of the compounds I given at the outset, collective terms were used which generally represent the following groups: Halogen: fluorine, chlorine, bromine and iodine; Alky!' straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, for example C1-C6-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methyl-pentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methyl¬propyl and l-ethyl-2-methylpropyl; Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for some or all of the hydrogen atoms in these groups to be replaC6d by halogen atoms as mentioned above, for example d-C2-haloalkyl, such as chloromethy1, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro-fluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl,• Cyeloalkvl; monocyclic alkyl groups having 3 to 6 carbon ring members, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; Alkenyli straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any position, for example C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-1-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, l,2-dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, 1,l-di-methyl-3-butenyl, 1,2-dimethyl-1-butenyl, l,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, 1,3-dimethyl- 3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,l,2-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl; Alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any position, for example C2-C6-alkynyl, such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, 1-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, 1,2-dimethyl-3-butyny1, 2,2-dimethy1-3-butyny1, 1-ethy1-2-butyny1, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; Hateraevclvl or hetarocrclvloxv. hafcarocvelvlthio and heterocvclvlamino: three- to six-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur and which are attached to the skeleton directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example, 2-tetrahydrofuranyl, oxirany1, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydro-thienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazoli-dinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazol-idin-3-yl, 1,3,4-oxadia-zolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydro-thien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydro-pyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydro- isoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol- 5-yl, 4,5-dihydroisoxazol-3-y1, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-y1, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydraisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,S-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,S-dihydrooxazol-5-y1, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-y1, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydro- pyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-y 1, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-l,3-thiazin-2-yl, 4H-3,l-benzothiazin-2-yl, 1,l-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydro- oxazin-2-yl, 1,3-dithian-2-yl; Arvl or arvloxy. arylthio. arvlcarbonyl and arvlaulfonvl: aromatic mono- or polycyclic hydrogen radicals which are attached to the skeleton directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-S02-)» for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals; Hatayyl or hetarvloxv, hatarvlthio. hatarvlcarbonvl and hetarylaulfonvli aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which are attached to the skeleton directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-J, (hetaryl-carbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (-SO2-), for example 5-memhered heteroarvl. containing one to three nitrogen atoms: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, l,2,4-triazol-3-yl and l,3,4-triazol-2-yl; 5-membered heteroarvl. containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxvaen or one sulfur atom; 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, l,2,4-oxadiazol-5-yl, l,2,4-thiadiazol-3-yl, l,2,4-thiadiazol-5-yl, l,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl; benzo-fused 5-membered heteroarvl. containing one to three nitrogen atoms or one nitrogen atom and/or one oxvaen or sulfur atom: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom as ring members, and in which two adjaC6nt carbon ring members or one nitrogen and one adjaC6nt carbon ring member may be bridged by a buta-l,3-dien-l,4-diyl group; 5-membered heteroarvl bonded via nitrooen and containing one to four nitrogen atoms, or benzo-fuaed 5-membered heteroarvl, bonded via nitrogen and containing one to three nitrogen atoms: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms and one to three nitrogen atoms, respectively, as ring members, and in which two adjaC6nt carbon ring members or one nitrogen and one adjaC6nt carbon ring member can be bridged by a buta-l,3-dien-l,4-diyl group, these rings being attached to the skeleton via one of the nitrogen ring members; 6-TMWBherBd heteroaryl containing nne to three and one to four njfrroqen atpms. respectively: 6-membered heteroaryl groups which, beside carbon atoms, can contain one to three nitrogen atoms and one to four nitrogen atoms, respectively, as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidiny1, 2-pyraziny1, 1,3,5-triazin-2-yl, l,2,4-triazin-3-yl and l,2,4,5-tetrazin-3-yl; benzo-fused fi-rngmberad heteroaryl containing one to fr.nr nitrooen atoms: 6-membered heteroaryl groups in which two adjaC6nt carbon ring members can be bridged by a buta-l,3-dien-l,4-diyl group, for example quinoline, isoquinoline, guinazoline and quinoxaline, i the corresponding oxy, thio, carbonyl or sulfonyl groups. HetarvlqmJ,np- aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are attached to the skeleton via a nitrogen atom. The speC1fication "partially or fully halogenated" is meant to express that some or all of the hydrogen atoms in the groups thus characterized may be replaC6d by identical or different halogen atoms as mentioned above. with respect to their biological activity, preferenC6 is given to compounds of the formula I in which m is 0. Likewise, preferenC6 is given to compounds of formula I in which Ri is methyl. Besides, preferenC6 is given to compounds I in which R3 is hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF3. Moreover, preferenC6 is given to compounds I in which R3 is methyl. Besides, preferenC6 is given to compounds I in which R3 is cyano. Furthermore, preferenC6 if given to compounds I in which R3 is cyclopropyl. Additionally, preferenC6 is given to compounds I in which R3 is CF3. Additionally, preferenC6 is given to compounds I in which R5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, unsubstituted or substituted aryl or hetaryl. Moreover, preferenC6 is given to compounds I in which R5 is methyl. Additionally, preferenC6 is given to compounds I in which R5 is ethyl. Moreover, preferenC6 is given to compounds I in which R5 is isopropyl. Moreover, preferenC6 is given to compounds I in which R5 is cyclopropyl. Moreover, preferenC6 is given to compounds I in which R5 is CF3. Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted aryl or hetaryl. Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl. Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted furyl, thienyl or pyrrolyl. Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl. Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted oxdiazolyl [sic], thiadiazolyl or triazolyl. Moreover, preferenC6 is given to compounds I in which R5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy1, amino, aminocarbonyl, aminothiocarbonyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alJcoxy, C1-C4-haloalJcoxy, C1-c4-aUylamino, di-C1-C4-alkylamino, C1-Ct-alkylsulfonyl, C1-C-i-alkoxycarbonyl, C1-C4-alkylaminocarbonyl or di-C1-C^-alkylaminocarbonyl. Moreover, preferenC6 is given to compounds I in which R4 is hydrogen, C1-C6-alkyl, C2-c6-alkenyl, C2-C6-alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl. Additionally, preferenC6 is given to compounds I in which R4 is C1-C6-alkyl. Further preferred compounds I are disclosed in WO 97/15,552. The compounds I which are contained in the mixtures according to the invention have exC6llent activity against a broad range of phytopathogenic fungi, in particular against fungi from the classes of the AscomyC6tes, DeuteromyC6tes, PhycornyC6tes and BasidiomyC6tes. They are espeC1ally important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable speC1es (for example cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, maize, fruit speC1es, riC6, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds. They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) in C6reals, Erysiphe C1choraC6arum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, UnC1nula necator in grapevines, FucC1nia speC1es in C6reals, Rhizoctonia speC1es in cotton, riC6 and lawns, Ustilago speC1es in C6reals and sugar cane, venturia inaegualis (scab) in apples, Helminthosporium speC1es in C6reals and riC6, Septoria nodorum in wheat, Botrytis C1nera [sic] (gray mold) in strawberries, vegetables, ornamentals and grapevines, C6rcospora arachidicola in groundnuts, PseudoC6rcosporella herpotrichoides in wheat and barley, Pyricularia oryzae in riC6 and lawns, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapevines, Pseudoperonospora speC1es in hops and cucumbers, Alternaria speC1es in vegetables and fruit, Mycosphaerella speC1es in bananas and Fusarium and VertiC1llium speC1es. The compounds II to VII are commerC1ally available as fungiC1des. when preparing the mixtures, it is preferred to employ the pure active ingredients I and II to vii, with which further active ingredients against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbiC1dal or growth-regulating active ingredients or fertilizers can be admixed. The mixtures of the compounds I and at least one compound II to VII can be applied simultaneously, that is joined or separately, and have outstanding action against a wide range of phytopathogenic fungi, in particular from the classes of the AscomyC6tes, BasidiomyC6tes, PhycomyC6tes and DeuteromyC6tes. Some of them act systematically and are therefore also suitable for use as foliar and soil-acting fungiC1des. They are espeC1ally important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable speC1es (for example cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, maize, fruit speC1es, riC6, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds. They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) in C6reals, Erysiphe C1choraC6arum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, UnC1nula necator in grapevines, PucC1nia speC1es in C6reals, Rhizoctonia speC1es in cotton, riC6 and lawns, Ustilago speC1es in C6reals and sugar cane, Venturia inaegualis (scab) in apples, Helminthosporium speC1es in C6reals and riC6, Septoria nodorum in wheat, Botrytis C1nera [sic] (gray mold) in strawberries, vegetables, ornamentals and grapevines, C6rcospora arachidicola in groundnuts, PseudoC6rcosporella herpotrichoides in wheat and barley, Pyricularia oryzae in riC6 and lawns, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapevines, Pseudoperonospora speC1es in hops and cucumbers, Alternaria speC1es in vegetables and fruit, Mycosphaerella speC1es in bananas and Fusarium and VertiC1llium speC1es. The mixtures according to the invention are particularly preferably utilizable for controlling Pyricularia oryzae. The compounds I and at least one of the compounds II to VII can be applied simultaneously, either together or separately, or in sucC6ssion, the sequenC6, in the case of separate application, generally not having any effect on the control results. Depending on the nature of the desired effect, the application rates of the mixtures according to the invention are, in particular in areas under agricultural cultivation, from 0.01 to 8 kg/ha, preferably from 0.1 to 5 kg/ha, in particular from 0.5 to 3.0 kg/ha. In the case of the compounds I, the application rates are from 0.01 to 2.5 kg/ha, preferably from 0.05 to 2.5 kg/ha, in particular from 0.1 to 1.0 kg/ha. Correspondingly, in the case of the compounds II to VII, the application rates are from 0.001 to 5 kg/ha, preferably from 0.005 to 2 JC6/ha, in particular from 0.01 to 1.0 kg/ha. For seed treatment, the application rates of the mixture are generally from 0.001 to 250 g/kg of seed, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg. If phytopathogenic harmful fungi are to be controlled, the separate or joint application of the compounds I and at least one of the compounds II to vii is effected by spraying or dusting the seeds, the plants or the soils before or after sowing the plants, or before or after plant emergenC6. The fungiC1dal synergistic mixtures according to the invention can be formulated for example in the form of ready-to-spray solutions, powder and suspensions or in the form of highly conC6ntrated aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, and applied by spraying, atomizing, dusting, broadcasting or watering. The use form depends on the intended purpose; in any case, it should ensure as fine and uniform as possible a distribution of the mixture according to the invention. The formulations are prepared in a known manner, for example by expanding the active ingredient with solvents and/or carriers, if desired by use of emulsifiers and dispersants. If the diluent used is water, it is also possible to use other organic solvents as auxiliary solvents. Suitable auxiliaries are essentially: solvents, such as aromatics {for example xylene), chlorinated aromatics (for example chlorobenzenes), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol), ketones (for example cyclohexanone), amines (for example ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silica gel, silicates); emulsifiers, such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants, such as ligninsulfite waste liquors and methylC6llulose. Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic aC1ds, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic aC1d, and of fatty aC1ds, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, or of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic aC1ds with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene [sic], lauryl alcohol polyglycol ether aC6tate, sorbitol esters, lignosulfite waste liquors or methylC6llulose. Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to VII or the mixture of the compounds I and at least one of the compounds II to VII with a solid carrier. Granules {eg. coated granules, impregnated granules or homogeneous granules) are usually prepared by binding the active ingredient, or active ingredients, to a solid carrier. Fillers or solid carriers are, for example, mineral earths, such as silica gel, siliC1c aC1ds, silica gels [sic], silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaC6ous earth, calC1um sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, and fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as C6real meal, tree bark meal, wood meal and nutshell meal, C6llulose powders or other solid carriers. The formulations generally comprise 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to VII or of the mixture of the compounds I and at least one of the compounds II to VII. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum [sic]). The corresponding formulations are applied by treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaC6s to be kept free from them with a fungiC1dally effective amount of the mixture, or of the compounds 1 and at least one of the compounds II to VII in the case of separate application. Application can be effected before or after infection by the harmful fungi. Examples of such preparations comprising the active ingredients are: I. A solution of 90 parts by weight of the active ingredients and 10 parts by weight of N-methylpyrrolidone; this solu¬tion is suitable for use in the form of microdrops; II. A mixture of 20 parts by weight of the active ingredients, 80 parts by weight of xylene, 10 parts by weight of the ad-duct of 8 to 10 mol of ethylene oxide and 1 mol of oleic aC1d N-monoethanolamide, 5 parts by weight of the calC1um salt of dodecylbenzenesulfonate, 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil; a dispersion is obtained by finely distributing the solu¬tion in water; III. An aqueous dispersion of 20 parts by weight of the active ingredients, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil; IV. An aqueous dispersion of 20 parts by weight of.the active ingredients, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280°C, and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil; V. A mixture, ground in a hammer mill, of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic aC1d, 10 parts by weight of the sodium salt of a lignosulfonic aC1d from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel; a spray mixture is obtained by finely distribu¬ting the mixture in water; VI. An intimate mixture of 3 parts by weight of the active in¬gredients and 97 parts by weight of finely divided kaolin; this dust comprises 3% by weight of active ingredient; vii. An intimate mixture of 30 parts by weight of the active In¬gredients, 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surfaC6 of this silica gel) this formulation im¬parts good adhesion to the active ingredient; VIII. A stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenolsulfonic aC1d/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of wa¬ter; this dispersion may be diluted further; IX. A stable oily dispersion of 20 parts by weight of the acti¬ve ingredients, 2 parts by weight of the calC1um salt of dodecylbenzenesulfonic aC1d, 8 parts by weight of fatty al¬cohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic aC1d/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. The synergistic activity of the mixtures according to the invention can be demonstrated by the following experiments: The active ingredients, separately or together, are formulated as a 10% emulsion in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier, and correspondingly diluted with water to the desired conC6ntration. Evaluation is carried out by determining the infected leaf areas in perC6nt. These perC6ntages are converted into efficaC1es. The efficacy (H) is calculated as follows using Abbot's formula: W - (1 - a)-100/p a corresponds to the fungal infection of the treated plants in % and P corresponds to the fungal infection of the untreated (control) plants in % An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected. The expected efficaC1es of the mixtures of the active ingredients were determined using Colby's formula [R.S. Colby, Heeds J£, 20-22 (1967)] and compared with the observed efficaC1es. eolbv's formula E= E expected efficacy, expressed in % of the untreated control, when using the mixture of the active ingredients A and B at the conC6ntrations a and b x efficacy, expressed in * of the untreated control, when using active ingredient A at the conC6ntration a y efficacy, expressed in % of the untreated control, when using active ingredient B at the conC6ntration b * Use Examples - Activity against Pyricularia oryzae (protective) Leaves of potted riC6 seedlings cv "Tai-Nong 67" were sprayed to runoff point with an aqueous preparation of active ingredient which had been prepared from a stock solution comprising 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were subsequently plaC6d in climatized chambers at 22-24°C and 95-99% relative atmospheric humidity for 6 days. The extent of the development of the disease on the leaves was then determined visually. The visually determined values for the perC6ntage of infected leaf area were converted into efficaC1es as perC6nt of the untreated control. An efficacy of 0 means the same infection as in the untreated control, an efficacy of 100 means 0% infection. The expected efficaC1es for active compound combinations were determined using Colby's formula (Colby, S.R.: "Calculating synergistic and antagonistic responses of herbiC1de combinations", Weeds 15. 20-22, 1967) and compared with the observed efficaC1es. The following compound I' was used as component a): The test results are shown in Tables 1 and 2 below: *) calculated using Colby'8 formula The test results show that the observed efficacy for all mixing ratios is higher than the efficacy which had been calculated beforehand using Colby's formula. We claim: X. A synergestic fungiC1dal mixture, comprising as active components a) phenylatic aC1d derivatives of the formula I in which the substituents and the index have the following meanings X is NOCH3, CHOCB3 or CHCH3; Y is oxygen or NR; Rl, R independently of one another are each hydrogen or C1-C4-alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl or C1-C4-alkoxy; m is 0, 1 or 2, where the radicals R2 may be different if m is 2; R3 is hydrogen, cyano, C1-Cj-alkyl, C1-C4-haloalkyl or C3-C6-cycloalkyl; R4, R6 independently of one another are each hydrogen, are C1-C1o-alkyl, C3-Cfi-cycloalkyl, Cj-C1o-alkenyl, C2-C1o-alkynyl, C1-C1o-alkylcarbonyl, C2-C1o-alkenylcarbonyl, Cs-C1o-alkynylcarbonyl or C1-C1o-alkylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups; cyano, nitro, hydroxy1, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, Cj-Cfi-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, Cx-C6-haloalkoxy, C1-C6-alkoxycarbonyl, Cj-C6-alkylthio, C1-Cfi-alkylamino, di-C1-C6-alxylamino, C1-C6-alkylaminocarbony1, di -C i -Cfi - alky 1 aminocarbony 1, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cyclo-alkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-Ct-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkyl-amino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkyl-aminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C«-alky 1 aminothiocarbonyl, cz-c$-alkenyl, C2-Cfi-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(-NOR7)-An-R8; are aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-Cfi-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-Cfi-alkylsulfony 1, C1-C6-alk.ylsulfoxyl, Ca-Cj-cycloalkyl, C1-C6-alkoxy, C1-c6-haloalkoxy, C1-c6-alkyloxycarbonyl, C1-c6-alkylthio, Cj-C6-alkylamino, di-Cj-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-Ct-alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NOR7J-An-R8; R5 is hydrogen, is C1-C6-alkyl, C2-C6-alkenyl, C2-c6-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxy1, mereapto, amino, carboxyl, amino-carbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl-aminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylamino-thiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C1-C6-alkoxy, C1-Cs-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkyl-amino, di-C1-C6-alkylamino, C2-Cs-alkenyloxy, Ca-C6-cycloalkyl, Cs-C6-cycloalkyloxy, hetero-cyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C$-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C4-alkoxy, hetarylthio, hetaryl-C1-C4-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, CjC6-cycloalkyl [sic], C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C«-alkylthio, C1-C6-alkyl-amino, di-C1-C6-alkylamino, C1-C$-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, Cj,-C$-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, Cj-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C is C3-Cfi-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1~C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkyl-thio, C1-C6-alkylamino, di-Cj-C6-alkylamina, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl, di-Cj-C«-alJcylaminothiocarbonyl, C2-C6-alkenyl, C2-Cfi-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; where A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C6-alxyl; n is 0 or 1; R7 is hydrogen or C1-C6-alxyl and R8 is hydrogen or C1-C6-alkyl, and their salts, and b) at least one compound of the formulae II to VII in a synergistically effective amount, wherein ratio range of compounds of formula I and compounds II to VII is 250:1 to 1:500. 2. The fungiC1dal mixture as claimed in claim 1 wherein ratio range of compounds of formula I and compounds II to VII is 100:1 to 1:10. The fungiC1dal composition as claimed in claim 1, which is conditioned in two parts, one part comprising the compound I in a solid or liquid carrier and the other part comprising at least one of the compounds II to VII in a solid or liquid carrier. I. The fungiC1dal mixture as claimed in claim 1 wherein the compound of formula I is 5. The composition as claimed in claim 3 wherein the compound of formula I is 6. A proC6ss for preparing a fungiC1dal composition as claimed in claim 2 comprising adding the compounds of formula I and II to VII with solid or liquid carriers.

Full Text

The present invention relates to fungiC1dal mixtures for controlling harmful fungi, comprising
a) phenylaC6tic aC1d derivatives of the formula I

in which the substituents and the index have the following meaning:
X is HOCH3, CHOCH3 or CHCH3;
Y is oxygen or NR;
R1, R independently of one another are each hydrogen or C1-C4-allcyl;
Ra is cyano, nitro, trifluoromethyl, halogen, C1-C^-alkyl or C1-C4-alkoxy;
m is 0, 1 or 2, where the radicals R2 may be different if m is 2;
R3 is hydrogen, cyano, C1-C^alkyl, C1-c4-haloalkyl or C3-C6-cycloalkyl;
R4, R6 independently of one another are each hydrogen,
are C1-C1o-alkyl, C3-C6-cycloalkyl, C2-C1o-alkenyl, C1-C1o-al^ynyl, C1-C1o-alkylcarbonyl, Cz-C1o-alkenyl-carbonyl, C3-C1o-alkynylcarbonyl or C1-C1o-alkyl-sulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto.

amino, carboxyl, aminocarbonyl, aminothiocarbony1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl-sulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-Cfi-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, Ca-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino¬carbonyl, aminothiocarbony1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, Cx-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-Cfi-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkyl-thio, C1-Cfi-alkylamino, di-C1-C6-alkylamino, Cx-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothio-carbonyl, C1-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C{»NOR7>-An-RB;
are aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetaryl-carbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothio¬carbony 1, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-c6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C1-halo-alkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkyl-aminathiocarbonyl, di-C1-C«-alkylaminothiocarbonylf C1-Cs-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C {=N0R7)-Aj,-R8;
R5 is hydrogen,
is C1-Cfi-alkyl, C1-C6-alkenyl, C2-C«-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto.

amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, di-C1-c«~alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkyl-aminotfC1ocarbonyl, C1-Cs-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1.-C6-alkoxy-carbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, Ca-Cs-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-c4-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C^-alkoxy, hetarylthio, hetaryl-C1-C^-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3C6-cycloalkyl [sic], C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-Cfi-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-Cft-alkylamino-carbony1, di-C1-Cfi-alkylaminac&rbony 1, C1-C6-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C{=NOR7)-An-R8;
is Ca-C6-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothio¬carbonyl, halogen, C1-C6-alkyl, C1-Cfi-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, Ca-C6-cyclo-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-carbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-Cs-alkylaminocarbonyl, C1-C6-alkylaminothio-carbonyl, di-C1-C6-alkylaminothiocarbonyl, Ca-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C^-alkyl;

n is 0 or 1;
R7 is hydrogen or C1-C6-allcyl and
R8 is hydrogen or C1-C6-alkyl,
and their salts,
and
b) at least one fungiC1de selected from fungiC1des of the formulae II to VII

It is an object of the present invention to provide fungiC1dal mixtures having good fungiC1dal activity, in particular against fungal diseases in riC6, exC6eding the activity of the mixture components on their own.
We have found that this object is achieved by the mixtures as claimed in claim 1.
The compounds of the formula I are known per se and are described in the literature (WO 97/15552).
The fungiC1des of the formulae II to VII are also known and described in the literature. In addition, they axe commerC1ally available under the trade names mentioned below in brackets:

II: DE-A 27 32 257, common name: pencycuron III:JP 01/104,514, common name: flutolanil (trade name: Moncut*, from Ninon Noyaku);
IV: US 3,937,840, common name: mepronil (trade name: Basitac®, from Kumiai);
V: common name; thifluzamide (trade name: Greatam®, from Monsanto);
VI: GB-A 1,312,536, OS 3,755,350; common name: iprodione (trade name: Rovral®, from Rhone-Poulenc);
VII: AG Chem New Compound Review, Vol. 15 (1997), 50; common name: furametpyr (trade name: Limber®, from Sumitomo).
Owing to their C=C and C=N double bonds, the preparation of the compounds I may yield E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, for example by crystallization or chromatography.
However, if the synthesis yields isomer mixtures, a separation is generally not neC6ssarily required sinC6 in some cases the individual isomers can be converted into one another during the preparation for use or upon use (for example under the action of light, aC1ds or bases). Similar conversions may also occur after the use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
With regard to the C=X double bond, preferenC6 is given to the E isomers of the compounds I (configuration based on the -0CH3 or the -CH3 group in relation to the -CO2R1 group) with respect to their activity.
With regard to the -C(R3)»NOCH2- double bond, preferenC6 is given to the C1s isomers of the compounds I (configuration based on the radical R3 in relation to the -OCH2- group) with respect to their activity.
In the definitions of the compounds I given at the outset, collective terms were used which generally represent the following groups:
Halogen: fluorine, chlorine, bromine and iodine;

Alky!' straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, for example C1-C6-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methyl-pentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methyl¬propyl and l-ethyl-2-methylpropyl;
Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for some or all of the hydrogen atoms in these groups to be replaC6d by halogen atoms as mentioned above, for example d-C2-haloalkyl, such as chloromethy1, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro-fluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl,•
Cyeloalkvl; monocyclic alkyl groups having 3 to 6 carbon ring members, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Alkenyli straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any position, for example C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-1-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, l,2-dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, 1,l-di-methyl-3-butenyl, 1,2-dimethyl-1-butenyl, l,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, 1,3-dimethyl-

3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,l,2-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl;
Alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any position, for example C2-C6-alkynyl, such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l,l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, 1-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, 1,2-dimethyl-3-butyny1, 2,2-dimethy1-3-butyny1, 1-ethy1-2-butyny1, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Hateraevclvl or hetarocrclvloxv. hafcarocvelvlthio and heterocvclvlamino: three- to six-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur and which are attached to the skeleton directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example, 2-tetrahydrofuranyl, oxirany1, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydro-thienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazoli-dinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazol-idin-3-yl, 1,3,4-oxadia-zolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydro-thien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydro-pyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydro-

isoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-
5-yl, 4,5-dihydroisoxazol-3-y1, 4,5-dihydroisoxazol-4-yl,
4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl,
2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,
2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-y1,
2,3-dihydroisopyrazol-5-yl, 4,5-dihydraisopyrazol-3-yl,
4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl,
2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl,
2,S-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl,
2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,
4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl,
4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl,
2,5-dihydrooxazol-4-yl, 2,S-dihydrooxazol-5-y1,
2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl,
2,3-dihydrothiazol-5-y1, 4,5-dihydrothiazol-2-yl,
4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,
2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,
2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl,
2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl,
4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl,
4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl,
2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,
2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl,
4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl,
2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydro-
pyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl,
1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-y 1,
1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl,
3,4,5,6-tetrahydropyridin-2-yl, 4H-l,3-thiazin-2-yl,
4H-3,l-benzothiazin-2-yl, 1,l-dioxo-2,3,4,5-tetrahydrothien-2-yl,
2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydro-
oxazin-2-yl, 1,3-dithian-2-yl;
Arvl or arvloxy. arylthio. arvlcarbonyl and arvlaulfonvl:
aromatic mono- or polycyclic hydrogen radicals which are attached to the skeleton directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-S02-)» for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
Hatayyl or hetarvloxv, hatarvlthio. hatarvlcarbonvl and hetarylaulfonvli aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which are

attached to the skeleton directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-J, (hetaryl-carbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (-SO2-), for example
5-memhered heteroarvl. containing one to three nitrogen atoms: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, l,2,4-triazol-3-yl and l,3,4-triazol-2-yl;
5-membered heteroarvl. containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxvaen or one sulfur atom; 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, l,2,4-oxadiazol-5-yl, l,2,4-thiadiazol-3-yl, l,2,4-thiadiazol-5-yl, l,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;
benzo-fused 5-membered heteroarvl. containing one to three nitrogen atoms or one nitrogen atom and/or one oxvaen or sulfur atom: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom as ring members, and in which two adjaC6nt carbon ring members or one nitrogen and one adjaC6nt carbon ring member may be bridged by a buta-l,3-dien-l,4-diyl group;
5-membered heteroarvl bonded via nitrooen and containing one to four nitrogen atoms, or benzo-fuaed 5-membered heteroarvl, bonded via nitrogen and containing one to three nitrogen atoms: 5-membered heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms and one to three nitrogen atoms, respectively, as ring members, and in which two adjaC6nt carbon ring members or one nitrogen and one adjaC6nt carbon ring member can be bridged by a

buta-l,3-dien-l,4-diyl group, these rings being attached to the skeleton via one of the nitrogen ring members;
6-TMWBherBd heteroaryl containing nne to three and one to four njfrroqen atpms. respectively: 6-membered heteroaryl groups which, beside carbon atoms, can contain one to three nitrogen atoms and one to four nitrogen atoms, respectively, as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidiny1, 2-pyraziny1, 1,3,5-triazin-2-yl, l,2,4-triazin-3-yl and l,2,4,5-tetrazin-3-yl;
benzo-fused fi-rngmberad heteroaryl containing one to fr.nr nitrooen atoms: 6-membered heteroaryl groups in which two adjaC6nt carbon ring members can be bridged by a buta-l,3-dien-l,4-diyl group, for example quinoline, isoquinoline, guinazoline and quinoxaline,
i the corresponding oxy, thio, carbonyl or sulfonyl groups.
HetarvlqmJ,np- aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are attached to the skeleton via a nitrogen atom.
The speC1fication "partially or fully halogenated" is meant to express that some or all of the hydrogen atoms in the groups thus characterized may be replaC6d by identical or different halogen atoms as mentioned above.
with respect to their biological activity, preferenC6 is given to compounds of the formula I in which m is 0.
Likewise, preferenC6 is given to compounds of formula I in which Ri is methyl.
Besides, preferenC6 is given to compounds I in which R3 is hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF3.
Moreover, preferenC6 is given to compounds I in which R3 is methyl.
Besides, preferenC6 is given to compounds I in which R3 is cyano.

Furthermore, preferenC6 if given to compounds I in which R3 is cyclopropyl.
Additionally, preferenC6 is given to compounds I in which R3 is CF3.
Additionally, preferenC6 is given to compounds I in which R5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, unsubstituted or substituted aryl or hetaryl.
Moreover, preferenC6 is given to compounds I in which R5 is methyl.
Additionally, preferenC6 is given to compounds I in which R5 is ethyl.
Moreover, preferenC6 is given to compounds I in which R5 is isopropyl.
Moreover, preferenC6 is given to compounds I in which R5 is cyclopropyl.
Moreover, preferenC6 is given to compounds I in which R5 is CF3.
Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted aryl or hetaryl.
Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.
Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted furyl, thienyl or pyrrolyl.
Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
Additionally, preferenC6 is given to compounds I in which R5 is unsubstituted or substituted oxdiazolyl [sic], thiadiazolyl or triazolyl.
Moreover, preferenC6 is given to compounds I in which R5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy1, amino, aminocarbonyl, aminothiocarbonyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alJcoxy, C1-C4-haloalJcoxy, C1-c4-aUylamino,

di-C1-C4-alkylamino, C1-Ct-alkylsulfonyl, C1-C-i-alkoxycarbonyl, C1-C4-alkylaminocarbonyl or di-C1-C^-alkylaminocarbonyl.
Moreover, preferenC6 is given to compounds I in which R4 is hydrogen, C1-C6-alkyl, C2-c6-alkenyl, C2-C6-alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
Additionally, preferenC6 is given to compounds I in which R4 is C1-C6-alkyl.
Further preferred compounds I are disclosed in WO 97/15,552.
The compounds I which are contained in the mixtures according to the invention have exC6llent activity against a broad range of phytopathogenic fungi, in particular against fungi from the classes of the AscomyC6tes, DeuteromyC6tes, PhycornyC6tes and BasidiomyC6tes.
They are espeC1ally important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable speC1es (for example cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, maize, fruit speC1es, riC6, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds.
They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) in C6reals, Erysiphe C1choraC6arum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, UnC1nula necator in grapevines, FucC1nia speC1es in C6reals, Rhizoctonia speC1es in cotton, riC6 and lawns, Ustilago speC1es in C6reals and sugar cane, venturia inaegualis (scab) in apples, Helminthosporium speC1es in C6reals and riC6, Septoria nodorum in wheat, Botrytis C1nera [sic] (gray mold) in strawberries, vegetables, ornamentals and grapevines, C6rcospora arachidicola in groundnuts, PseudoC6rcosporella herpotrichoides in wheat and barley, Pyricularia oryzae in riC6 and lawns, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapevines, Pseudoperonospora speC1es in hops and cucumbers, Alternaria speC1es in vegetables and fruit, Mycosphaerella speC1es in bananas and Fusarium and VertiC1llium speC1es.
The compounds II to VII are commerC1ally available as fungiC1des.

when preparing the mixtures, it is preferred to employ the pure active ingredients I and II to vii, with which further active ingredients against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbiC1dal or growth-regulating active ingredients or fertilizers can be admixed.
The mixtures of the compounds I and at least one compound II to VII can be applied simultaneously, that is joined or separately, and have outstanding action against a wide range of phytopathogenic fungi, in particular from the classes of the AscomyC6tes, BasidiomyC6tes, PhycomyC6tes and DeuteromyC6tes. Some of them act systematically and are therefore also suitable for use as foliar and soil-acting fungiC1des.
They are espeC1ally important for controlling a large number of fungi in a variety of crop plants, such as cotton, vegetable speC1es (for example cucumbers, beans, tomatoes, potatoes and cucurbits), barley, grass, oats, bananas, coffee, maize, fruit speC1es, riC6, rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety of seeds.
They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) in C6reals, Erysiphe C1choraC6arum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, UnC1nula necator in grapevines, PucC1nia speC1es in C6reals, Rhizoctonia speC1es in cotton, riC6 and lawns, Ustilago speC1es in C6reals and sugar cane, Venturia inaegualis (scab) in apples, Helminthosporium speC1es in C6reals and riC6, Septoria nodorum in wheat, Botrytis C1nera [sic] (gray mold) in strawberries, vegetables, ornamentals and grapevines, C6rcospora arachidicola in groundnuts, PseudoC6rcosporella herpotrichoides in wheat and barley, Pyricularia oryzae in riC6 and lawns, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapevines, Pseudoperonospora speC1es in hops and cucumbers, Alternaria speC1es in vegetables and fruit, Mycosphaerella speC1es in bananas and Fusarium and VertiC1llium speC1es.
The mixtures according to the invention are particularly preferably utilizable for controlling Pyricularia oryzae.
The compounds I and at least one of the compounds II to VII can be applied simultaneously, either together or separately, or in sucC6ssion, the sequenC6, in the case of separate application, generally not having any effect on the control results.

Depending on the nature of the desired effect, the application rates of the mixtures according to the invention are, in particular in areas under agricultural cultivation, from 0.01 to 8 kg/ha, preferably from 0.1 to 5 kg/ha, in particular from 0.5 to 3.0 kg/ha.
In the case of the compounds I, the application rates are from 0.01 to 2.5 kg/ha, preferably from 0.05 to 2.5 kg/ha, in particular from 0.1 to 1.0 kg/ha.
Correspondingly, in the case of the compounds II to VII, the application rates are from 0.001 to 5 kg/ha, preferably from 0.005 to 2 JC6/ha, in particular from 0.01 to 1.0 kg/ha.
For seed treatment, the application rates of the mixture are generally from 0.001 to 250 g/kg of seed, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg.
If phytopathogenic harmful fungi are to be controlled, the separate or joint application of the compounds I and at least one of the compounds II to vii is effected by spraying or dusting the seeds, the plants or the soils before or after sowing the plants, or before or after plant emergenC6.
The fungiC1dal synergistic mixtures according to the invention can be formulated for example in the form of ready-to-spray solutions, powder and suspensions or in the form of highly conC6ntrated aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, and applied by spraying, atomizing, dusting, broadcasting or watering. The use form depends on the intended purpose; in any case, it should ensure as fine and uniform as possible a distribution of the mixture according to the invention.
The formulations are prepared in a known manner, for example by expanding the active ingredient with solvents and/or carriers, if desired by use of emulsifiers and dispersants. If the diluent used is water, it is also possible to use other organic solvents as auxiliary solvents. Suitable auxiliaries are essentially: solvents, such as aromatics {for example xylene), chlorinated aromatics (for example chlorobenzenes), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol), ketones (for example cyclohexanone), amines (for example ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silica

gel, silicates); emulsifiers, such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants, such as ligninsulfite waste liquors and methylC6llulose.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic aC1ds, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic aC1d, and of fatty aC1ds, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, or of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic aC1ds with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene [sic], lauryl alcohol polyglycol ether aC6tate, sorbitol esters, lignosulfite waste liquors or methylC6llulose.
Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to VII or the mixture of the compounds I and at least one of the compounds II to VII with a solid carrier.
Granules {eg. coated granules, impregnated granules or homogeneous granules) are usually prepared by binding the active ingredient, or active ingredients, to a solid carrier.
Fillers or solid carriers are, for example, mineral earths, such as silica gel, siliC1c aC1ds, silica gels [sic], silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaC6ous earth, calC1um sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, and fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as C6real meal, tree bark meal, wood meal and nutshell meal, C6llulose powders or other solid carriers.
The formulations generally comprise 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to VII or of the mixture of the compounds I and at least one of the compounds II to VII. The

active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum [sic]).
The corresponding formulations are applied by treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaC6s to be kept free from them with a fungiC1dally effective amount of the mixture, or of the compounds 1 and at least one of the compounds II to VII in the case of separate application.
Application can be effected before or after infection by the harmful fungi.
Examples of such preparations comprising the active ingredients are:
I. A solution of 90 parts by weight of the active ingredients and 10 parts by weight of N-methylpyrrolidone; this solu¬tion is suitable for use in the form of microdrops;
II. A mixture of 20 parts by weight of the active ingredients, 80 parts by weight of xylene, 10 parts by weight of the ad-duct of 8 to 10 mol of ethylene oxide and 1 mol of oleic aC1d N-monoethanolamide, 5 parts by weight of the calC1um salt of dodecylbenzenesulfonate, 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil; a dispersion is obtained by finely distributing the solu¬tion in water;
III. An aqueous dispersion of 20 parts by weight of the active ingredients, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil;
IV. An aqueous dispersion of 20 parts by weight of.the active ingredients, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280°C, and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil;
V. A mixture, ground in a hammer mill, of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic aC1d, 10 parts by weight of the sodium salt of a lignosulfonic aC1d from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel; a spray mixture is obtained by finely distribu¬ting the mixture in water;
VI. An intimate mixture of 3 parts by weight of the active in¬gredients and 97 parts by weight of finely divided kaolin; this dust comprises 3% by weight of active ingredient;

vii. An intimate mixture of 30 parts by weight of the active In¬gredients, 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surfaC6 of this silica gel) this formulation im¬parts good adhesion to the active ingredient;
VIII. A stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenolsulfonic aC1d/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of wa¬ter; this dispersion may be diluted further;
IX. A stable oily dispersion of 20 parts by weight of the acti¬ve ingredients, 2 parts by weight of the calC1um salt of dodecylbenzenesulfonic aC1d, 8 parts by weight of fatty al¬cohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic aC1d/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
The synergistic activity of the mixtures according to the invention can be demonstrated by the following experiments:
The active ingredients, separately or together, are formulated as a 10% emulsion in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier, and correspondingly diluted with water to the desired conC6ntration.
Evaluation is carried out by determining the infected leaf areas in perC6nt. These perC6ntages are converted into efficaC1es. The efficacy (H) is calculated as follows using Abbot's formula:
W - (1 - a)-100/p
a corresponds to the fungal infection of the treated plants in
% and P corresponds to the fungal infection of the untreated
(control) plants in %
An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficaC1es of the mixtures of the active ingredients were determined using Colby's formula [R.S. Colby, Heeds J£, 20-22 (1967)] and compared with the observed efficaC1es.
eolbv's formula* E=
E expected efficacy, expressed in % of the untreated control,
when using the mixture of the active ingredients A and B at
the conC6ntrations a and b x efficacy, expressed in * of the untreated control, when using
active ingredient A at the conC6ntration a y efficacy, expressed in % of the untreated control, when using
active ingredient B at the conC6ntration b * Use Examples - Activity against Pyricularia oryzae (protective)
Leaves of potted riC6 seedlings cv "Tai-Nong 67" were sprayed to runoff point with an aqueous preparation of active ingredient which had been prepared from a stock solution comprising 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were subsequently plaC6d in climatized chambers at 22-24°C and 95-99% relative atmospheric humidity for 6 days. The extent of the development of the disease on the leaves was then determined visually.
The visually determined values for the perC6ntage of infected leaf area were converted into efficaC1es as perC6nt of the untreated control. An efficacy of 0 means the same infection as in the untreated control, an efficacy of 100 means 0% infection. The expected efficaC1es for active compound combinations were determined using Colby's formula (Colby, S.R.: "Calculating synergistic and antagonistic responses of herbiC1de combinations", Weeds 15. 20-22, 1967) and compared with the observed efficaC1es.
The following compound I' was used as component a):

The test results are shown in Tables 1 and 2 below:

*) calculated using Colby'8 formula
The test results show that the observed efficacy for all mixing ratios is higher than the efficacy which had been calculated beforehand using Colby's formula.

We claim:
X. A synergestic fungiC1dal mixture, comprising as active components
a) phenylatic aC1d derivatives of the formula I

in which the substituents and the index have the following meanings
X is NOCH3, CHOCB3 or CHCH3;
Y is oxygen or NR;
Rl, R independently of one another are each hydrogen or C1-C4-alkyl;
R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl or C1-C4-alkoxy;
m is 0, 1 or 2, where the radicals R2 may be different if m is 2;
R3 is hydrogen, cyano, C1-Cj-alkyl, C1-C4-haloalkyl or C3-C6-cycloalkyl;
R4, R6 independently of one another are each hydrogen,
are C1-C1o-alkyl, C3-Cfi-cycloalkyl, Cj-C1o-alkenyl, C2-C1o-alkynyl, C1-C1o-alkylcarbonyl, C2-C1o-alkenylcarbonyl, Cs-C1o-alkynylcarbonyl or C1-C1o-alkylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups; cyano, nitro,

hydroxy1, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, Cj-Cfi-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, Cx-C6-haloalkoxy, C1-C6-alkoxycarbonyl, Cj-C6-alkylthio, C1-Cfi-alkylamino, di-C1-C6-alxylamino, C1-C6-alkylaminocarbony1, di -C i -Cfi - alky 1 aminocarbony 1, C1-C6-alkylaminothiocarbonyl,
di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cyclo-alkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups for their part may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-Ct-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkyl-amino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkyl-aminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C«-alky 1 aminothiocarbonyl, cz-c$-alkenyl, C2-Cfi-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(-NOR7)-An-R8;
are aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-Cfi-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-Cfi-alkylsulfony 1, C1-C6-alk.ylsulfoxyl, Ca-Cj-cycloalkyl, C1-C6-alkoxy, C1-c6-haloalkoxy, C1-c6-alkyloxycarbonyl, C1-c6-alkylthio, Cj-C6-alkylamino, di-Cj-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-Ct-alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(=NOR7J-An-R8;

R5 is hydrogen,
is C1-C6-alkyl, C2-C6-alkenyl, C2-c6-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxy1, mereapto, amino, carboxyl, amino-carbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl-aminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylamino-thiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkyl-sulfoxyl, C1-C6-alkoxy, C1-Cs-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkyl-amino, di-C1-C6-alkylamino, C2-Cs-alkenyloxy, Ca-C6-cycloalkyl, Cs-C6-cycloalkyloxy, hetero-cyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C$-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C4-alkoxy, hetarylthio, hetaryl-C1-C4-alkylthio, where the cyclic radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, CjC6-cycloalkyl [sic], C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C«-alkylthio, C1-C6-alkyl-amino, di-C1-C6-alkylamino, C1-C$-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, Cj,-C$-alkyl-aminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, Cj-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C is C3-Cfi-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1~C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkyl-thio, C1-C6-alkylamino, di-Cj-C6-alkylamina, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylamino-carbonyl, C1-C6-alkylaminothiocarbonyl,

di-Cj-C«-alJcylaminothiocarbonyl, C2-C6-alkenyl, C2-Cfi-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C6-alxyl;
n is 0 or 1;
R7 is hydrogen or C1-C6-alxyl and
R8 is hydrogen or C1-C6-alkyl,
and their salts,
and b) at least one compound of the formulae II to VII

in a synergistically effective amount, wherein ratio range of compounds of formula I and compounds II to VII is 250:1 to
1:500.
2. The fungiC1dal mixture as claimed in claim 1 wherein ratio range of compounds of formula I and compounds II to VII is 100:1 to 1:10.

The fungiC1dal composition as claimed in claim 1, which is conditioned in two parts, one part comprising the compound I in a solid or liquid carrier and the other part comprising at least one of the compounds II to VII in a solid or liquid carrier.
I. The fungiC1dal mixture as claimed in claim 1 wherein the compound of formula I is

5. The composition as claimed in claim 3 wherein the compound
of formula I is

6. A proC6ss for preparing a fungiC1dal composition as claimed
in claim 2 comprising adding the compounds of formula I and II to VII with solid or liquid carriers.

Documents:

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Patent Number

224838

Indian Patent Application Number

IN/PCT/2000/535/CHE

PG Journal Number

49/2008

Publication Date

05-Dec-2008

Grant Date

23-Oct-2008

Date of Filing

17-Oct-2000

Name of Patentee

BASF AKTIENGESELLSCHAFT

Applicant Address

D-67056 LUDWIGSHAFEN,

Inventors:

#	Inventor's Name	Inventor's Address
1	THOMAS GROTE	BRESLAUER STR. 6, 67105 SCHIFFERSTADT,
2	EBERHARD AMMERMANN	VON-GAGERN-STR. 2, 64646 HEPPENHEIM,
3	SIEGFRIED STRATHMANN	DONNERSBERGSTR. 9, D-67117 LIMBURGERHOF,
4	HUBERT SAUTER	NECKARPROMENADE 20, 68167 MANNHEIM,
5	GISELA LORENZ	ERLENWEG 13, 67434 NEUSTADT,
6	KLAUS SCHELBERGER	TRAMINERWEG 2, 67161 GONNHEIM,

PCT International Classification Number

A01N37/50

PCT International Application Number

PCT/EP99/01907

PCT International Filing date

1999-03-22

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	198 12 763.4	1998-03-24	Germany