A method for combating sudden death syndrome in soybeans using substituted pyrazolamides

Abstract

"METHOD FOR COMBATING SOYBEAN SUDDEN DEATH SYNDROME USING SUBSTITUTED PYRAZOLAMIDES". The present invention relates to a method for reducing the occurrence of phytopathogenic fungi selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae in plants, comprising applying an effective amount of a composition comprising a compound of formula (I) (I), to a plant seed before planting, to the soil in which a plant is growing or in which it is desired to grow, to the roots of the plant or to combinations thereof, wherein said plant seed or said plant roots are infected with a fungal strain selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae.

Description

Descriptive report of the invention patent for a METHOD OF COMBATING SUDDEN DEATH SYNDROME IN SOYBEANS USING SUBSTITUTED PYRAZOLAMIDES.

[01] The present invention relates to a method for reducing the occurrence of sudden death syndrome in useful plant crops, in particular soybeans, which method comprises applying a pyrazolyl-carboxamide to the plant, seed and / or soil.

[02] Sudden Death Syndrome (SDS) is a fungal disease, especially of soybeans, found in North America caused by Fusarium virguliforme (Fusarium solani f.sp. glycines). Similarly, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov., and Fusarium tucumaniae are known precursors to SDS in other regions of the world, for example, in South America. Fusarium virguliforme produces toxins that are translocated from the primary root to the foliage. Infected plants will begin to show distinct yellow speckles or spots between the veins (interveinal chlorosis). As the disease progresses, these areas become larger and, in severe cases, the entire area between the veins becomes brown and dry. The disease is of major concern due to its potential to reduce yield, from a slight yield loss to 100%, depending on the soybean variety. The pathogen was isolated from soybean roots and lower stems, but not from leaves.Therefore, it is not possible to combat this disease by applying a fungicide to the leaves.

[03] Solutions to this problem are currently rare. Document WO 2012 / 071520 describes a method for reducing the occurrence of Sudden Death Syndrome, comprising the application of an ethylbenzamide pyridinyl to the seeds, soil or roots of plants. Document WO 2011 / 163474 describes a method for reducing the occurrence of Sudden Death Syndrome, comprising the application of thiabendazole to the seeds of plants. 2 / 56

[04] It is therefore proposed, according to the present invention, a method for reducing the occurrence of phytopathogenic fungi selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae in plants, comprising the application of an effective amount of a composition comprising a compound of formula I in what R is hydrogen or methoxy; in what R1 is hydrogen, halogen, or C1-C6 alkyl; R2 is hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, cycloalkyl(C3-C6)-alkynyl(C3-C6), halophenoxy, halophenyl-alkynyl(C3-C6), C(C1-C4 alkyl)=NO-alkyl(C1-C4), C1C6 haloalkyl, C1-C6 haloalkoxy, C2-C6 haloalkenyl or C2-C6 haloalkenyloxy; R3 is hydrogen, halogen, or C1-C6 alkyl; provided that at least one of R1, R2, and R3 is not hydrogen; 3 / 56 R4, R5, and R6, independently of each other, are hydrogen, halogen, or R7; provided that at least one of R4, R5, and R6 is not hydrogen; R7 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C4 alkoxyalkyl; and R8 is hydrogen or methoxy; and agrochemically acceptable salts, isomers, stereoisomers, diastereomers, enantiomers and tautomers of these compounds; to a plant seed before planting, to the soil in which a plant is growing, or in which it is desired to grow, to the roots of the plant, or to combinations thereof, wherein said plant seed or said plant roots are infected with a fungal strain selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov., and Fusarium tucumaniae.

[05] Alkyl groups occurring in substituent definitions may have a linear or branched chain and are, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, or tert-butyl. Alkoxy, alkenyl, and alkynyl radicals are derived from the aforementioned alkyl radicals. Alkenyl and alkynyl groups may be mono- or di-unsaturated. Cycloalkyl groups occurring in substituent definitions are, for example, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. The halogen is generally fluorine, chlorine, bromine, or iodine, preferably fluorine, bromine, or chlorine. This also applies correspondingly to halogen in combination with other terms, such as halogenalkyl or halogenalkoxy. Haloalkyl groups preferably have a chain length of 1 to 4 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl 4 / 56 romethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl. The alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy. Halogenalkoxy compounds are, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

[06] Compounds of formula I can occur in two enantiomeric forms with formulas Ia and Ib: ch3 CH3(Ib).

[07] The invention encompasses both enantiomeric forms of the compounds of formula I. The compounds of formula I and their preparation are described in documents WO 2010 / 063700, WO 2010 / 084078 and WO 2008 / 151828.

[08] A preferred embodiment of the invention comprises a method for reducing the occurrence of phytopathogenic fungi selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae in plants, comprising applying an effective amount of a composition comprising a compound of formula I to a plant seed before planting, wherein said plant seed is infected with a fungal strain selected from the group consisting of Fusarium virguliforme, Fusarium brasili 5 / 56 ense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae. In this preferred embodiment, the phytopathogenic fungus is preferentially Fusarium virguliforme.

[09] Another preferred embodiment of the invention is a method for suppressing, controlling or reducing Sudden Death Syndrome in plants comprising planting in the soil a plant seed treated with a compound of formula I and wherein said plant seeds or soil contain a precursor for Sudden Death Syndrome, in particular Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae.

[010] A further preferred embodiment of the invention is a method for reducing damage to a plant or plant seed caused by Sudden Death Syndrome comprising applying a compound of formula I to a plant seed before planting, wherein said plant seed contains a precursor to Sudden Death Syndrome; and sowing said plant seed.

[011] The plant seed is preferably soybean seed.

[012] A further preferred embodiment of the invention is a soybean seed treated with a composition comprising a compound of formula I in an amount to reduce the occurrence of phytopathogenic fungi selected from the group consisting of Fusarium virguliforme, Fusarium brasiliense sp. nov., Fusarium cuneirostrum sp. nov. and Fusarium tucumaniae in plants.

[013] The compounds of [2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid and methoxy-[1-methyl-2-(2,4,5-trichlorothiopheno-3-yl)-ethyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid are especially useful for the methods according to the present invention, including all preferred embodiments of the methods. 6 / 56

[014] In a further preferred group of compounds of formula I, which is especially useful for the methods according to the present invention, including all preferred embodiments of the methods, R is methoxy and Q is Q1. In this preferred group, R1, R2, and R3 are, independently of each other, either hydrogen or chlorine, provided that at least one of R1, R2, and R3 is not hydrogen. In this preferred group, R1, R2, and R3 are all preferably chlorine, and R8 represents hydrogen.

[015] The preferred compounds of formula I for the method of the present invention, including all the preferred embodiments mentioned above, are listed in the following Table 1: Table 1: Compounds with formula Ic: (Ic), Compound No. Ri R2 R3 Q R4 R5 R6 R8 1.001 Cl Cl Cl Qi - - - H 1.002 Cl H Cl Qi - - - H 7 / 56 Composto No. Ri R2 R3 Q R4 R5 R6 R8 1.003 Cl Cl H Qi - - - H 1.004 Cl Br Cl Qi - - - H 1.005 Br Br Br Qi - - - H 1.006 H Cl H Qi - - - H 1.007 H Br H Qi - - - H 1.008 H CF3 H Qi - - - H 1.009 - - - Q2 Cl Cl Cl H 1.010 - - - Q2 Cl H Cl H 1.011 - - - Q2 H Cl Cl H 1.012 - - - Q2 Cl Cl Br H 1.013 - - - Q2 Cl H Br H 1.014 - - - Q2 H Cl Br H 1.015 - - - Q2 H Cl H H 1.016 - - - Q2 Cl H H H 1.017 Cl Cl Cl Qi - - - OCH3 1.018 Cl H Cl Qi - - - OCH3 1.019 Cl Cl H Qi - - - OCH3 1.020 Cl Br Cl Qi - - - OCH3 1.021 Br Br Br Qi - - - OCH3 1.022 H Cl H Qi - - - OCH3 1.023 H Br H Qi - - - OCH3 1.024 H CF3 H Qi - - - OCH3 1.025 - - - Q2 Cl Cl Cl OCH3 1.026 - - - Q2 Cl H Cl OCH3 1.027 - - - Q2 H Cl Cl OCH3 1.028 - - - Q2 Cl Cl Br OCH3 1.029 - - - Q2 Cl H Br OCH3 8 / 56 Composto No. Ri R2 R3 Q R4 R5 R6 R8 1.030 - - - Q2 H Cl Br OCH3 1.031 - - - Q2 H Cl H OCH3 1.032 - - - Q2 Cl H H OCH3

[016] Componentes (A) adicionais preferidos são listados na Table 2 following: Table 2: Compounds of formula Id: (Id), in which Q is (Q2); Compound no. Ri R2 R3 Q R4 R5 R6 R8 2.001 Cl Cl Cl Q1 - - - H 2.002 Cl H Cl Qi - - - H 2.003 Cl Cl H Qi - - - H 2.004 Cl Br Cl Qi - - - H 2.005 Br Br Br Qi - 0 Qi - H - 0 Qi - H H 2.007 H Br H Qi - - - H 2.008 H CF3 H Qi - - - H 9 / 56 Composto No. Ri R2 R3 Q R4 R5 R6 Rs 2.009 - - - Q2 Cl Cl Cl H 2.010 - - - Q2 Cl H Cl H 2.011 - - - Q2 H Cl Cl H 2.012 - - - Q2 Cl Cl Br H 2.013 - - - Q2 Cl H Br H 2.014 - - - Q2 H Cl Br H 2.015 - - - Q2 H Cl H H 2.016 - - - Q2 Cl H H H 2.017 Cl Cl Cl Q1 - - - OCH3 2.018 Cl H Cl Qi - - - OCH3 2.019 Cl Cl H Qi - - - OCH3 2.020 Cl Br Cl Qi - - - OCH3 2.021 Br Br Br Qi - - - OCH3 2.022 H Cl H Qi - - - OCH3 2.023 H Br H Qi - - - OCH3 2.024 H CF3 H Qi - - - OCH3 2.025 - - - Q2 Cl Cl Cl OCH3 2.026 - - - Q2 Cl H Cl OCH3 2.027 - - - Q2 H Cl Cl OCH3 2.028 - - - Q2 Cl Cl Br OCH3 2.029 - - - Q2 Cl H Br OCH3 2.030 - - - Q2 H Cl Br OCH3 2.031 - - - Q2 H Cl H OCH3 2.032 - - - Q2 Cl H H OCH3

[017] The term plants or useful plants is to be understood as also including useful plants that have been made tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, e.g., primis10 / 56 sulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enolpyrovylshikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors) as a result of conventional breeding or genetic engineering methods. An example of a crop that has been made tolerant to imidazolinones, e.g., imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (Canola).Examples of crops that have been made tolerant to herbicides or herbicide classes through genetic engineering methods include commercially available glyphosate- and glufosinate-resistant corn varieties under the trademarks RoundupReady®, Herculex I®, and LibertyLink®.

[018] The term useful plants is to be understood as also including useful plants that have been so transformed by the use of recombinant DNA techniques that they are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[019] Examples of such plants are: YieldGard® (a variety of maize that expresses a CryIA(b) toxin); YieldGard Rootworm® (a variety of maize that expresses a CryIIIB(b1) toxin); YieldGard Plus® (a variety of maize that expresses a CryIA(b) toxin and a CryIIIB(b1) toxin); Starlink® (a variety of maize that expresses a Cry9(c) toxin); Herculex I® (a variety of maize that expresses a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a variety of cotton that expresses a CryIA(c) toxin); Bollgard I® (a variety of cotton that expresses a CryIA(c) toxin); Bollgard II® (a variety of cotton that expresses a CryIA(c) toxin and a CryIIA(b) toxin); 11 / 56 VIPCOT® (a cotton variety that expresses a VIP toxin); NewLeaf® (a potato variety that expresses a CryIIIA toxin); NatureGard® Agrisure® GT Advantage (glyphosate tolerance trait GA21), Agrisure® CB Advantage (corn borer (CB) trait Bt11), Agrisure® RW (corn rootworm trait) and Protecta®.

[020] The term plants or useful plants is to be understood as also including useful plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing antipathogenic substances having a selective action, such as, for example, the so-called pathogenesis-related proteins (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to a person skilled in the art and are described, for example, in the publications mentioned above.

[021] According to the invention, plants or useful plants typically comprise the following plant species: grapevines; cereals, such as wheat, barley, rye or oats; beets, such as sugar beets or fodder beets; fruits, such as pomes, stone fruits or soft fruits, for example, apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soybeans; oilseed plants, such as rapeseed, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or peanuts; cucumber plants, such as zucchini, cucumbers or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruits or tangerines; vegetables and greens, such as spinach, 12 / 56 lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits or paprika; laurel plants, such as avocados, cinnamon or camphor; corn; tobacco; nuts; coffee; sugar cane; tea; grapevines; hops; durian; bananas; natural rubber plants; grass or ornamental plants, such as flowers, shrubs, broad-leaved or evergreen trees, for example, conifers. This list does not represent any limitation.

[022] The compounds of formula I can be used in unmodified form or, preferably, in conjunction with carriers and adjuvants conventionally employed in the formulation technique.

[023] For this purpose, the compounds of formula I and the inert carriers are conveniently formulated in known ways into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations e.g. in polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomizing, dusting, dispersing, coating or pouring, are chosen according to the intended objectives and the prevailing circumstances. The compositions may also contain other adjuvants such as stabilizers, antifoaming agents, viscosity regulators, binders or adhesives, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[024] Suitable carriers and adjuvants may be solid or liquid and are substances useful in formulation technology, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890. 13 / 56

[025] Compounds of formula I or compositions comprising a compound of formula I, as the active ingredient, and an inert carrier may be applied to the plant site or to the plant to be treated, simultaneously or in succession with additional compounds. These additional compounds may be, for example, fertilizers or micronutrient donors or other preparations that influence plant growth.

[026] The frequency of application and the application rate will depend on the risk of infestation by the corresponding pathogen. Compounds of formula I can penetrate the plant through the roots via the soil (systemic action) by soaking the plant locus with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). Compounds of formula I can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[027] A formulation, that is, a composition comprising the compound of formula I and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimate mixing and / or trituration of the compound with diluents, for example, solvents, solid carriers and, optionally, compounds with surface activity (surfactants).

[028] Agrochemical formulations will normally contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. 14 / 56

[029] Although it is preferable to formulate commercial products as concentrates, the end user will normally use diluted formulations.

[030] Advantageous application rates typically range from 5 g to 2 kg of active ingredient (AI) per hectare (ha), preferably from 10 g to 1 kg AI / ha, more preferably from 20 g to 600 g AI / ha. When used as a seed soaking agent, suitable application rates range from 10 mg to 1 g of active substance per kg of seeds. The application rate for the desired action can be determined by experimentation. This depends, for example, on the type of action, the developmental stage of the useful plant, and the application (location, timing, application method) and, due to these parameters, can vary within wide limits.

[031] Formulation examples for compounds of formula I: Examples F-1.1 to F-1.2: Emulsifiable concentrates Components F-1.1 F-1.2 compound of Tables 1-2 25% 50% calcium dodecylbenzenesulfonate 5% 6% castor oil polyethylene glycol ether (36 mol ethylene oxy units) tributylphenol polyethylene glycol ether 5% - (30 mol ethylene oxy units) - 4% cyclohexanone - 20% xylene mixture 65% 20%

[032] Emulsions of any desired concentration can be prepared by diluting these concentrates with water. Example F-2: Emulsifiable concentrate 15 / 56 Components F-2 compound from Tables 1-2 octylphenol polyethylene glycol ether (4 to 5 mol ethylene oxy units) calcium dodecylbenzene sulfonate polyglycol castor oil ether (36 mol ethylene oxy units) cyclohexanone 10% 3% 3% 4% 30% xylene mixture 50%

[033] Emulsions of any desired concentration can be prepared by diluting these concentrates with water. Examples F-3.1 through F-3.4: Solutions Components F-3.1 F-3.2 F-3.3 F-3.4 compound from Tables 1-2 80% propylene glycol monomethyl ether 20% polyethylene glycol (relative molecular weight: 400 atomic mass units) 10% 5% 95% - - - - - N-methylpyrrolid-2-one - epoxidized coconut oil - benzine (boiling range: 160-190°) 70% - - 20% - - - 1% 5% - - 94% -

[034] The solutions are suitable for use in microdrop form. Examples F-4.1 to F-4.4: Granules 16 / 56 Components F-4.1 F-4.2 F-4.3 F-4.4 compound from Tables 1-2 5% kaolin 94% highly dispersed silicic acid 10% 8% 21% - 79% 54% 1% attapulgite - - 13% 7% 90% - 18%

[035] The new compound is dissolved in dichloromethane, the solution is sprayed onto the vehicle and the solvent is then removed by vacuum distillation. Examples F-5.1 and F-5.2: Dusts Components F-5.1 F-5.2 compound from Tables 1-2 highly dispersed silicic acid talc 2% 5% 1% 5% 97% - kaolin - 90%

[036] Ready-to-use powders are obtained by intimate mixing of all components. Examples F-6.1 to F-6.3: Wettable powders Components F-6.1 F-6.2 F-6.3 compound from Tables 1-2 lignin sodium sulfonate sodium lauryl sulfate 25% 50% 75% 5% 5% - 3% - 5% 17 / 56 sodium diisobutylnaphthalene sulfonate - 6% 10% octylphenol polyethylene glycol ether (7 to 8 mol ethyleneoxy units) - 2% - highly dispersed silicic acid 5% 10% 10% kaolin 62% 27% -

[037] All components are mixed and the mixture is extensively ground in a suitable mill to give rise to wettable powders which can be diluted with water to form suspensions of any desired concentration. Example F7: Flowable concentrate for seed treatment composed of the ingredients in Tables 1 to 2: 40% propylene glycol, 5% butanol PO / EO copolymer, 2% tristenephenol with 10-20 moles of EO. 1,2-benzisothiazolin-3-one (in the form of a 0.5% solution in water) calcium salt of monoazo pigment 5% Silicone oil (in the form of a 75% emulsion in 0.2% water) Water 45.3%

[038] The finely ground active ingredient is intimately mixed with the adjuvants, giving a concentrated suspension from which suspensions of any desired dilution can be obtained by dilution with water. Using these dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. 18 / 56

[039] The methods according to the invention can also be used in combination with other additional pesticides in order to increase the spectrum of pest control.

[040] The said combination may contain components (A) and (B), wherein component (A) is the compound of formula I and component (B) is a compound selected from the group consisting of (B1) a strobilurin fungicide, (B2) an azole fungicide, (B3) a morpholine fungicide, (B4) an anilinopyrimidine fungicide, (B5) a fungicide selected from the group consisting of:

[041] anilazine, arsenates, benalaxyl, benalaxyl-M, benodanil, benomyl, bentiavalicarb, bentiavalicarb-isopropyl, biphenyl, bitertanol, blasticidin-S, Bordeaux mixture, boscalid, bupirimate, cadmium chloride, captafol, captan, carbendazim, carbon disulfide, carboxin, carpropamide, cedar leaf oil, quinomethionate, chlorine, chloroneb, chlorothalonil, clozolinate, cinnamaldehyde, copper, copper ammonium carbonate, copper hydroxide, copper octanoate, copper oleate, copper sulfate, cyazofomide, cycloheximide, cymoxanil, diclofluanide, diclone, dichloropropene, diclocimeth, diclomezine, dichloran, dietofencarb, diflumetorim, dimethylimoyl, dimethomorph, dinocap, dithianon, dodine, edifenfos, etaboxam, etirimol, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamifos, fenarimol, fenfuran, fenhexamide, fenoxanil, fenpiclonil, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flusulfamide, flutolanil, folpet,formaldehyde, fosetyl-aluminum, phthalide, fuberidazole, furalaxyl, furamethpyr, fliodine, fuazatin, hexachlorobenzene, himhexazole, iminoctadine, iodocarb, iprobenfos, iprodione, iprovalicarb, isoprothiolan, kasugamycin, mancozeb, maneb, manganous dimethyldithiocarbamate, 19 / 56 mefenoxam, mepronil, mercuric chloride, mercury, metalaxyl, metasulfocarb, metiram, metrafenone, nabam, bitterberry oil (hydrophobic extract), nuarimol, octilinone, ofurace, oxadixil, copper oxin, oxolinic acid, oxycarboxin, oxytetracycline, paclobutrazol, paraffin oil, paraformaldehyde, pencicuron, pentachloronitrobenzene, pentachlorophenol, penthiopyrade, perforazoate, phosphoric acid, polyoxin, polyoxin D zinc salt, potassium bicarbonate, probenazole, procymidone, propamocarb, propineb, proquinazid, prothiocarb, pyrazofos, pirifenox, piroquilon, quinoxifene, quintozene, silthiofam, sodium bicarbonate, sodium diacetate, sodium propionate, streptomycin, sulfur, TCMTB, tecloftalam, technazene, thiabendazole, tifluzamide, thiophanate, thiophanatemethyl, thiram, tolclofos-methyl, tolifluanide, triazoxide, Trichoderma harzianum, tricyclazole, triforin, triphenyltin hydroxide, validamycin, vinclozoline, zineb, ziram, zoxamide, 1,1-bis(4-chlorophenyl)-2ethoxyethanol, benzenosulfonate of 2,4-dichlorophenyl, 2-fluoro-N-methyl-N-, 1-naphthyl acetamide, 4-chlorophenyl phenyl sulfone, a compound of formula B-5.1 CH OH / VyNxZWo^ch3 í 1 li II I 3 <NxSfr N N Cl (B-5.2) um composto de fórmula B-5.3 (B-5.1) 20 / 56 A compound of formula B-5.4 (B-5.4), a compound of formula B-5.5 (B-5.5), a compound of formula B-5.6 (B-5.6), a compound of formula B-5.7 (B-5.7),

[042] (2-bicyclopropyl-2-yl-phenyl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.8), (9-isopropyl-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl)-amide of 3-difluoromethyl-121 / 56 methyl-1H-pyrazole-4-carboxylic acid (compound B-5.9), [2-(1,3-dimethylbutyl)phenyl]-amide of 1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid (compound B-5.10), (3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-yl)amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.11), N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2(trifluoromethyl)benzamide (compound B-5.12), N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.13), N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.14), N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.15), N-(4'-trifluoromethyl-biphen-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B5.16), N-(2'-trifluoromethyl-biphen-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.17) and N-(2'-trifluoromethylbiphen-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.18);. (B6) a plant bioregulator selected from the group consisting of acibenzolar-S-methyl, chlormequat chloride, ethephon, mepiquat chloride and trinexapac ethyl; (B7) an insecticide selected from the group consisting of abamectin, clothianidin, emamectin benzoate, imidacloprid, tefluthrin, thiamethoxam, a compound of formula B-7.1 22 / 56 a compound with formula B-7.2; (B-7.2); a compound with formula B-7.3 (B8) glyphosate, a compound with formula V fomesafen, and (B9) isopyrazam, sedaxane, a compound of formula (VI) (VI), a compound with formula (VII) 23 / 56 ch3 (VII),

[043] 1 -[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1yl]ethanone, 1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1yl]ethanone [1003318-67-9], and 3-Difluoromethyl-1-methyl-1 acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide H-pyrazole-4-carboxylic acid.

[044] According to the present invention, preferred glyphosate salts are potassium, isopropylammonium, sodium, trimesium, ammonium and diammonium salts. Preferred glufosinate salts are disclosed in US-A-4, 168,963, a preferred salt being the ammonium salt.

[045] According to the present invention, a racemic compound means a mixture of at least two enantiomers in a ratio of substantially 50:50.

[046] In general, the weight ratio between component (A) and component (B) ranges from 2000:1 to 1:1000. A non-limiting example of such weight ratios of formula I compound: formula B-2 compound is 10:1. The weight ratio between component (A) and component (B) is preferably 100:1 to 1:100; more preferably 20:1 to 1:50.

[047] The mixture of active ingredients of component (A) and component (B) comprises compounds of formula I and other active ingredients or compositions from a biocidal point of view or, preferably, in a mixing ratio of 1000:1 to 1:1000, particularly 50:1 to 1:50, more particularly in a ratio of 20:1 to 1:20, even more particularly 10:1 to 1:10, most particularly 24 / 56 from 5:1 to 1:5, with particular preference given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 being equally preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. It is understood that such mixing ratios include, on the one hand, weight ratios and also, on the other hand, molar ratios.

[048] It has been surprisingly discovered that certain weight ratios between component (A) and component (B) are capable of giving rise to synergistic activity. This synergistic activity is clear from the fact that the fungicidal activity of the composition comprising component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and component (B). This synergistic activity extends the range of action of component (A) and component (B) in two ways. Firstly, the application rates of component (A) and component (B) are reduced while the action remains equally good, meaning that the mixture of active ingredients still achieves a high degree of control of phytopathogens even where the two individual components have become totally ineffective at such a low range of application rates. Secondly, there is a substantial broadening of the spectrum of phytopathogens that can be controlled.

[049] However, in addition to the actual synergistic action with respect to fungicidal activity, the compositions according to the invention may also have other surprisingly advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of 25 / 56 useful plant benefits including: emergence, crop yields, more developed root system, increased tillering, increased plant height, larger leaf blade, fewer dead basal leaves, stronger shoots, greener leaf color, less fertilizer needed, fewer seeds needed, more productive shoots, earlier flowering, earlier grain maturity, less plant tilting (lodging), increased shoot growth, improved plant vigor, and earlier germination.

[050] Components (B) are known. Where components (B) are included in The Pesticide Manual [The Pesticide Manual - A World Compendium; Thirteenth Edition; Publisher: CDS Tomlin; The British Crop Protection Council], they are described therein with the entry number referred to above in parentheses in this document for the particular component (B); for example, the compound abamectin is described with entry number (1). In this document, most of the components (B) described above are referred to by a said common name, the relevant ISO common name or another common name that is used in particular cases.If the designation is not a common name, the nature of the alternative designation used is given in parentheses for the particular component (B); in this case, the IUPAC name, the Chemical Abstracts / IUPAC name, a chemical name, a traditional name, a compound name, or a development code is used, or, if none of these designations or a common name is used, an alternative name is used.

[051] The following components (B) are registered with a CAS Registry No. aldimorph (CAS 91315-15-0); arsenates (CAS 1327-53-3); benalaxyl-M (CAS 98243-83-5); bentiavalicarb (CAS 413615-35-7); cadmium chloride (CAS 10108-64-2); cedar leaf oil (CAS 8007-20-3); chlorine (CAS 7782-50-5); cinnamaldehyde (CAS: 26 / 56 104-55-2); copper ammonium carbonate (CAS 33113-08-5); copper oleate (CAS 1120-44-1); iodocarb (3-iodo-2-propynylbutyl carbamate) (CAS 55406-53-6); himexazole (CAS 10004-44-1); manganous dimethyldithiocarbamate (CAS 15339-36-3); mercury (CAS 7487-94-7; 21908-53-2; 7546-30-7); metrafenone (CAS 220899-03-6); bitter oil (hydrophobic extract) (CAS 8002-65-1); orisastrobin (CAS 248593-16-0); paraformaldehyde (CAS 30525-89-4); penthiopyrad (CAS 183675-82-3); phosphoric acid (CAS 7664-38-2); potassium bicarbonate (CAS 298-14-6); sodium bicarbonate (CAS 144-55-8); sodium diacetate (CAS 127-09-3); sodium propionate (CAS 137-40-6); TCMTB (CAS 21564-17-0); and tolifluanide (CAS 731-27-1).

[052] Compound B-1.1 (“enestrobin”) is described in EP-0-936213; compound B-3.1 (“flumorph”) in US-6,020,332, CN-1-167-568, CN-1-155-977 and in EP-0-860-438; compound B-5.1 (“mandipropamide”) in WO 01 / 87822; compound B-5.2 in WO 98 / 46607; compound B-5.3 (“fluopicolide”) in WO 99 / 42447; compound B-5.4 (“cyflufenamide”) in WO 96 / 19442; compound B-5.5 in WO 99 / 14187; compound B-5.6 (“piribencarb”) is registered with CAS Registry Number 325156-49-8; Compound B-5.7 (“amisulbrom” or “ambromdol”) is registered under CAS Registry Number 348635-87-0; Compound B-5.8 ((2-bicyclopropyl-2-ylphenyl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid) is described in WO 03 / 74491; Compound B-5.9 ((9-isopropyl-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid) is described in WO 04 / 35589 and in WO 06 / 37632; Compound B-5.10 ([2-(1,3-dimethylbutyl)phenyl]-amide of 1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid) is described in WO 03 / 10149; compound B-5.11 ((3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid; “bixaphene”) is registered with CAS Registry Number: 581809-46-3 and is described in document WO 03 / 70705;. Compound B-5.12 (N-{2-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2(trifluoromethyl)benzamide; “fluopiram”) is registered under CAS Registry Number 658066-35-4 and is described in WO 04 / 16088; compounds B-5.13, B-5.14 and B-5.15 are described in WO 2007 / 17450; compounds B-5.16, B-5.17 and B-5.18 are described in WO 2006 / 120219. The compound with formula B-7.1 is described in document WO 03 / 015519, the compound with formula B-7.2 is described in document WO 2004 / 067528, the compound with formula B-7.3 is described in document WO 2007 / 115644. The compound with formula V is described in document WO 2001 / 094339. Isopirazam (3-(difluoromethyl)1-methyl-N-[1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4-methanonaphthalen-5-yl]-1-pyrazol-4-carboxamide) is described in document WO 2004 / 035589, in document WO 2006 / 037632 and in document EP 1556385 and is registered with CAS Registry Number 881685-58-1.Sedaxane (N-[2-[1bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazol-4carboxamide) is described in WO document 2003 / 074491 and is registered with CAS Registry 874-967; The formula compound (VI) is described in WO paper 2008 / 014870; and compounds of formula (VII) as described in WO document 2007 / 0 Fomesafen is registered under Registration No. CAS 72178-02-0 1-[4-[4-[(5S)5-(2,6difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-yl]-2-[5methyl-3-(trifluoromethyl)-nane H-pyrazolane -[4-[4-[5-(2,6difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5methyl-3-(trifluoromethyl)-1H-pyrazol-ethano31,1]-yl both disclosed in our papers WO 2010 / 123791, WO 2008 / 013925, WO 2008 / 013622 and WO 2011 / 051243 page 20), and (3',4',5'-trifluoroyl acido)amide-2 3-difluoromethyl-1-methyl-1H-pyrazol-4carboxylic is disclosed in WO paper 2006 / 087343.

[053] Throughout this document, the term composition refers to the various mixtures or combinations of components (A) and (B), 28 / 56 for example, in a simple “ready-mix” form, in a combined spray mixture prepared from separate formulations of the individual active ingredient components, such as a “tank mix”, and in a combined use of the individual active ingredients when applied sequentially, i.e., one after the other in a relatively short period of time, such as a few hours or days. The order of application of components (A) and (B) is not essential to the operation of the present invention.

[054] The compositions according to the invention may also comprise more than one of the active components (B), if, for example, it is desired to increase the spectrum of disease control. For example, it may be advantageous in agricultural practice to combine two or three components (B) with component (A). An example is a composition comprising a compound of formula (I), azoxystrobin and cyproconazole.

[055] The following mixtures of components (A) with components (B) are preferred (the abbreviation TX means: a compound selected from the group consisting of the compounds specifically described in Tables 1 and 2 of this invention): (B1) a strobilurin + TX fungicide, (B2) an azole + TX fungicide, (B3) a morpholine + TX fungicide, (B4) an anilinopyrimidine + TX fungicide, (B5) a fungicide selected from the group consisting of:

[056] anilazine + TX, arsenates + TX, benalaxyl + TX, benalaxylM + TX, benodanil + TX, benomyl + TX, bentiavalicarb + TX, bentiavalicarb-isopropyl + TX, biphenyl + TX, bitertanol + TX, blasticidin-S + TX, bordeaux mixture + TX, boscalid + TX, bupirimate + TX, cadmium chloride + TX, captafol + TX, captana + TX, carbendazim + TX, dis 29 / 56 carbon disulfide + TX, carboxin + TX, carpropamide + TX, cedar leaf oil + TX, quinomethionate + TX, chlorine + TX, chloroneb + ​​TX, chlorothalonil + TX, clozolinate + TX, cinnamaldehyde + TX, copper + TX, copper ammonium carbonate + TX, copper hydroxide + TX, copper octanoate + TX, copper oleate + TX, copper sulfate + TX, cyazofamid + TX, cycloheximide + TX, cymoxanil + TX, diclofluanide + TX, diclone + TX, dichloropropene + TX, diclocimeth + TX, diclomezine + TX, dicloran + TX, dietofencarb + TX, diflumetorim + TX, dimethimol + TX, dimethomorph + TX, dinocap + TX, dithianon + TX, dodina + TX, edifenfos + TX, etaboxam + TX, ethyrimole + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenaminosulf + TX, fenamiphos + TX, fenarimol + TX, fenfuram + TX, fenhexamide + TX, fenoxanil + TX, fenpiclonil + TX, fentin acetate + TX, fentin chloride + TX, fentin hydroxide + TX, ferbam + TX, ferimzone + TX, fluazinam + TX, fludioxonil + TX, flusulfamide + TX,flusulfamide + TX, flutolanil + TX, folpet + TX, formaldehyde + TX, fosetyl-aluminum + TX, phthalide + TX, fuberidazole + TX, furalaxyl + TX, furamethpyr + TX, fliodin + TX, fuazatin + TX, hexachlorobenzene + TX, himhexazole + TX, iminoctadine + TX, iodocarb + TX, iprobenfos + TX, iprodione + TX, iprovalicarb + TX, isoprothiolan + TX, kasugamycin + TX, mancozeb + TX, maneb + ​​TX, manganous dimethyldithiocarbamate + TX, mefenoxam + TX, mepronil + TX, mercuric chloride + TX, mercury + TX, metalaxyl + TX, metasulfocarb + TX, metiram + TX, metrafenone + TX, nabam + TX, bitterwood oil (hydrophobic extract) + TX, nuarimol + TX, octilinone + TX, ofurace + TX, oxadixil + TX, copper oxin + TX, oxolinic acid + TX, oxycarboxin + TX, oxytetracycline + TX, paclobutrazol + TX, paraffin oil + TX, paraformaldehyde + TX, pencicuron + TX, pentachloronitrobenzene + TX, pentachlorophenol + TX, penthiopyrad + TX, perforazoate + TX, phosphoric acid + TX, polyoxin + TX,zinc salt of polyoxin D + TX, potassium bicarbonate + TX, probenazole + TX, procymidone + TX, propamo 30 / 56 carbe + TX, propineb + ​​TX, proquinazid + TX, protiocarb + TX, pyrazophos + TX, pirifenox + TX, piroquilon + TX, quinoxifene + TX, quintozene + TX, siltiofam + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin + TX, sulfur + TX, TCMTB + TX, tecloftalam + TX, tecnazine + TX, thiabendazole + TX, tifluzamide + TX, thiophanate + TX, thiophanate-methyl + TX, thiram + TX, tolclofos-methyl + TX, tolifluanide + TX, triazoxide + TX, trichoderma harzianum + TX, tricyclazole + TX, triforin + TX, hydroxide triphenyltin + TX, validamycin + TX, vinclozolin + TX, zineb + ​​TX, ziram + TX, zoxamide + TX, 1 + TX, 1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2-benzenesulfonate + TX,4-dichlorophenyl + TX, 2-fluoro-N-methyl-N-1naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, compound of formula B-5.1 + TX one a compound with the formula B-5.2 + TX a compound with the formula B-5.3 + TX (B-5.3) + TX, a compound with the formula B-5.4 + TX 31 / 56 (B-5.4) + TX, a compound with the formula B-5.5 + TX (B-5.5) + TX, a compound with the formula B-5.6 + TX CH3 (B-5.6) + TX, a compound with the formula B-5.7 + TX (B-5.7) + TX,

[057] (2-bicyclopropyl-2-yl-phenyl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.8) + TX, (9-isopropyl-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.9) + TX, [2-(1,3-dimethylbutyl)phenyl]-amide of 1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid (compound B-5.10) + TX, (3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid 32 / 56 (compound B-5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2(trifluoromethyl)benzamide (compound B-5.12) + TX, N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.13) + TX, N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.14), N-[2-(2-chloro-1 + TX,1,2-trifluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.15) + TX, N-(4'-trifluoromethyl-biphen-2-yl)amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.16) + TX, N-(2'-trifluoromethyl-biphen-2-yl)amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.17) and N-(2'-trifluoromethyl-biphen-2-yl)amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.18) + TX; (B6) a plant bioregulator selected from the group consisting of

[058] acibenzolar-S-methyl + TX, chlormequat chloride + TX, ethephon + TX, mepiquat chloride and trinexapac ethyl;

[059] (B7) an insecticide selected from the group consisting of

[060] abamectin + TX, clothianidin + TX, emamectin benzoate + TX, imidacloprid + TX, tefluthrin + TX, thiamethoxam + TX, a compound of formula B-7.1 (B-7.1) + TX; a compound with formula B-7.2; 33 / 56 (B-7.2) + TX; and a compound with formula B-7.3 THE Cl O(B-7.3) + TX and (B8) glyphosate + TX, a compound with the formula V + TX fomesafen + TX, and (B9) isopyrazam + TX, sedaxane + TX, a compound of formula (VI) + TX (VI), a compound with formula (VII) + TX (VII), 34 / 56 [061 ] 1 -[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1yl]ethanone + TX, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1yl]ethanone + TX, and (3',4',5'-trifluoro-biphenyl-2-yl)-amide of 3difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid + TX.

[062] The following mixtures of components (A) with components (B) are especially preferred: (B1) a strobilurin + TX fungicide, (B2) an azole + TX fungicide, (B3) a morpholine + TX fungicide, (B4) an anilinopyrimidine + TX fungicide, (B5) a fungicide selected from the group consisting of:

[063] anilazine (878) + TX, arsenates + TX, benalaxyl (56) + TX, benalaxyl-M + TX, benodanil (896) + TX, benomyl (62) + TX, bentiavalicarb + TX, bentiavalicarb-isopropyl (68) + TX, biphenyl (81) + TX, bitertanol (84) + TX, blasticidin-S (85) + TX, bordeaux mixture (87) + TX, boscalid (88) + TX, bupirimate (98) + TX, cadmium chloride + TX, captafol (113) + TX, captan (114) + TX, carbendazim (116) + TX, carbon disulfide (945) + TX, carboxin (120) + TX, carpropamide (122) + TX, cedar leaf oil + TX, quinomethionate (126) + TX, chlorine + TX, chloroneb (139) + TX, chlorothalonil (142) + TX, clozolinate (149) + TX, cinnamaldehyde + TX, copper + TX, copper ammonium carbonate + TX, copper hydroxide (169) + TX, copper octanoate (170) + TX, copper oleate + TX, copper sulfate (87) + TX, ciazofamid (185) + TX, cycloheximide (1022) + TX, cymoxanil (200) + TX, diclofluanide (230) + TX, diclone (1052) + TX, dichloropropene (233) + TX, diclocimet (237) + TX,diclomezina (239) + TX, dicloran (240) + TX, dietofencarb (245) + TX, diflumetorim (253) + TX, dimethirimol (1082) + TX, 35 / 56 dimethomorph (263) + TX, dinocap (270) + TX, dithionone (279) + TX, dodina (289) + TX, edifenphos (290) + TX, etaboxam (304) + TX, ethymol (1133) + TX, etridiamozole (321) + TX (322) + TX, phenamidone (325) + TX, fenaminosulf (1144) + TX, fenamiphos (326) + TX, phenarimol (327) + TX, fenfuram (333) + TX, fenhexamide (334) + TX, phenoxanil (338) + TX, phenyl (34) + TX fentine acetate (347) + TX, fentine chlorate + TX, fentine hydroxide (347) + TX, ferbam (350) + TX, ferrimzone (351) + TX, fluazinam (363) + TX, fludioxonil (368) + TX, fluosulfomide (349) + TX (396) + TX, folpet (400) + TX, formaldehyde (404) + TX, fosetyl-aluminum (407) + TX, phthalide (643) + TX, fuberidazole (419) + TX, furaloxyl (410) + TX, furametpyr (411) + TX, fluodine (400) + TX (125) (422) + TX, hexachlorobenzene (434) + TX, himexazol + TX, iminoctadine (459) + TX, iodocarbe (3-iodo-2-propynyl and butyl carbamate) + TX, iprobenphos (IBP) (469) + TX, hyprodione (470) + TXiprovalicarb (471) + TX, isoprothiolan (474) + TX, kasugamycin (483) + TX, mancozeb (496) + TX, maneb (497) + TX, manganous dimethyldithiocarbamate + TX, mefenoxam (Metalaxyl-M) (517) + TX, mepronil (510) + TX, mercuric chloride (511) + TX, mercury + TX, metalaxyl (516) + TX, metasulfocarb (528) + TX, metiram (546) + TX, metrafenone + TX, nabam (566) + TX, bitter oil (hydrophobic extract) + TX, nuarimol (587) + TX, octilinone (590) + TX, ofurace (592) + TX, oxadixil (601) + TX, copper oxine (605) + TX, oxolinic acid (606) + TX, oxycarboxin (608) + TX, oxytetracycline (611) + TX, paclobutrazole (612) + TX, paraffin oil (628) + TX, paraformaldehyde + TX, pencicuron (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopryde + TX, perforazoate + TX, phosphoric acid + TX, polyoxin (654) + TX, zinc salt of polyoxin D (654) + TX, potassium bicarbonate + TX, probenazole (658) + TX, procymidone (660) + TX, propamocarb (668) + TX,propineb (676) + TX, proquinazid (682) + TX, protiocarb (1361) + TX, pirazo36 / 56 fos (693) + TX, pirifenox (703) + TX, piroquilon (710) + TX, quinoxifene (715) + TX, quintozene (PCN(B) (716) + TX, siltiofam (729) + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin (744) + TX, sulfur (754) + TX, TCMTB + TX, tecloftalam + TX, tecnazine (TCN(B) (767) + TX, thiabendazole (790) + TX, tifluzamide (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, tolclofos-methyl (808) + TX, tolylfluanid (810) + TX, triazoxide (821) + TX, trichoderma harzianum (825) + TX, tricyclazole (828) + TX, triforin (838) + TX, triphenyltin hydroxide (347) + TX, validamycin (846) + TX, vinclozolin (849) + TX, zineb (855) + TX, ziram (856) + TX, zoxamide (857) + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, benzenesulfonate of 2 + TX,4-dichlorophenyl (IUPAC Name / Chemical Abstracts) (1059) + TX,2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, a compound of formula B-5.1 + TX, (B-5.1) a compound with the formula B-5.2 + TX (B-5.2) a compound with the formula B-5.3 + TX (B-5.3) + TX, 37 / 56 a compound with the formula B-5.4 + TX (B-5.4) + TX, a compound with the formula B-5.5 + TX (B-5.5) + TX, a compound with the formula B-5.6 + TX CH3 (B-5.6), a compound with the formula B-5.7 + TX (B-5.7) + TX,

[064] (2-bicyclopropyl-2-yl-phenyl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.8) + TX, (9-isopropyl1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.9) + TX, [2-(1,3-dimethylbutyl)phenyl]-amide of 1,3-dimethyl-5-fluoro-1H-pyrazole4-carboxylic acid (compound B-5.10) + TX, (3',4'-dichloro-5-fluoro-1,1'-biphenyl38 / 56 2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (compound B-5.12) + TX, N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.13) + TX, N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.14) + TX, N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.15) + TX, N-(4'-trifluoromethyl-biphen-2-yl)amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.16) + TX, N-(2'-trifluoromethyl-biphen-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.17) and N(2'-trifluoromethyl-biphen-2-yl)-amide of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (compound B-5.18);

[065] (B6) a plant bioregulator selected from the group consisting of

[066] acibenzolar-S-methyl (6) + TX, chlormequat chloride (137) + TX, ethephon (307) + TX, mepiquat chloride (509) and trinexapac ethyl (841);

[067] (B7) an insecticide selected from the group consisting of

[068] abamectin (1) + TX, clothianidin (165) + TX, emamectin benzoate (291) + TX, imidacloprid (458) + TX, tefluthrin (769) + TX, thiamethoxam (792) + TX, a compound of formula B-7.1 + TX a compound with the formula B-7.2 + TX 39 / 56 a compound with formula B-7.3 (B8) glyphosate (419) + TX. Examples of particularly suitable mixtures selected from the following group P: Group P: mixtures especially suitable according to the invention:

[069] a strobilurin fungicide selected from azoxystrobin (47) + TX, dimoxystrobin (226) + TX, fluoxastrobin (382) + TX, cresoxim-methyl (485) + TX, methominostrobin (551) + TX, oryzastrobin + TX, picoxystrobin (647) + TX, pyraclostrobin (690); trifloxystrobin (832) + TX, a compound of formula B-1.1 + TX

[070] a selected azole fungicide of azaconazole (40) + TX, bromuconazole (96) + TX, ciproconazole (207) + TX, difenoconazole (247) + TX, diniconazole (267) + TX, diniconazole-M (267) + TX, epoxiconazole (298) + TX, fenbuconazole (329) + TX, fluquinconazole (385) + TX, flusilazole (393) + TX, flutriafol (397) + TX, hexaconazole (435) + TX, imazalil (449) + TX, imibenconazole (457) + TX, ipconazole (468) + TX, metcon 40 / 56 zol (525) + TX, myclobutanil (564) + TX, oxpoconazole (607) + TX, pefurazoate (618) + TX, penconazole (619) + TX, prochloraz (659) + TX, propiconazole (675) + TX, prothioconazole (685) + TX, simeconazole (731) + TX, tebuconazole (761) + TX, tetraconazole (778) + TX, triadimefon (814) + TX, triadimenol (815) + TX, triflumizole (834) + TX, triticonazole (842) + TX, diclobutrazol (1068) + TX, etaconazole (1129) + TX, furconazole (1198) + TX, furconazole-cis (1199) and quinconazole (1378);

[071] a fungicidal mixture of morpholine selected from aldimorph + TX, dodemorph (288) + TX, fenpropimorph (344) + TX, tridemorph (830) + TX, fenpropidine (343) + TX, spiroxamine (740) + TX, piperaline (648) and a compound of formula B-3.1 +TX N. O (B-3.1);

[072] an aniline-pyrimidine fungicide selected from cyprodinil (208) + TX, mepanipyrim (508) and pyrimethanil (705);

[073] a fungicidal mixture selected from the group consisting of

[074] anilazine (878) + TX, arsenates + TX, benalaxyl (56) + TX, benalaxyl-M + TX, benodanyl (896) + TX, benomyl (62) + TX, bentiavalicarb + TX, bentiavalicarb-isopropyl (68) + TX, biphenyl (81) + TX, bitertanol (84) + TX, blasticidin-S (85) + TX, bordeaux mixture (87) + TX, boscalid (88) + TX, bupyrimate (98) + TX, cadmium chloride + TX, capitafol (113) + TX,

[075] captan (114) + TX, carbendazim (116) + TX, carbon disulfide (945) + TX, carboxin (120) + TX, carpropamide (122) + TX, cedar leaf oil + TX, quinomethionate (126) + TX, chlorine + TX, chloroneb (139) + TX, chlorothalonil (142) + TX, clozolinate (149) + TX, ci 41 / 56 namaldehyde + TX, copper + TX, copper ammonium carbonate + TX, copper hydroxide (169) + TX, copper octanoate (170) + TX, copper oleate + TX, copper sulfate (87) + TX, cyazofamid (185) + TX, cycloheximide (1022) + TX, cymoxanil (200), dimetirimol (1082) + TX, dimethomorph (263) + TX, dinocap (270) + TX, dithianon (279) + TX, dodine (289) + TX, edifenfos (290) + TX, etaboxam (304) + TX, etirimol (1133) + TX, etridiazole (321) + TX, famoxadone (322) + TX, fenamidone (325) + TX, fenaminosulf (1144) + TX, fenamifos (326) + TX, fenarimol (327) + TX, fenfuran (333) + TX, fenhexamid (334) + TX, fenoxanil (338) + TX, fenpiclonil (341) + TX, fentin acetate (347) + TX, fentin chloride + TX, hydroxide of fentin (347) + TX, ferbam (350) + TX, ferimzone (351) + TX,fluazinam (363) + TX, fludioxonil (368) + TX, flusulfamide (394) + TX, flutolanil (396) + TX, folpet (400) + TX, formaldehyde (404) + TX, fosetyl-aluminum (407) + TX, phthalide (643) + TX, fuberidazole (419) + TX, furalaxyl (410) + TX, furamethpir (411) + TX, fliodin (1205) + TX, fuazatin (422) + TX, hexachlorobenzene (434) + TX, himexazole + TX, iminoctadine (459) + TX, iodocarb (3-iodo-2-propynyl butyl carbamate) + TX, iprobenfos (IBP) (469) + TX, iprodione (470) + TX, iprovalicarb (471) + TX, isoprothiolan (474) + TX, kasugamycin (483) + TX, mancozeb (496) + TX, maneb (497) + TX, manganous dimethyldithiocarbamate + TX, mefenoxam (Metalaxyl-M) (517) + TX, mepronil (510) + TX, mercuric chloride (511) + TX, mercury + TX, metalaxyl (516) + TX, metasulfocarb (528) + TX, metiram (546) + TX, metrafenone + TX, nabam (566) + TX, bitter oil (hydrophobic extract) + TX, nuarimol (587) + TX, octilinone (590) + TX, ofurace (592) + TX, oxadixil (601) + TX, copper oxine (605) + TX,oxolinic acid (606) + TX, oxycarboxin (608) + TX, oxytetracycline (611) + TX, paclobutrazole (612) +, 42 / 56 TX, paraffin oil (628) + TX, paraformaldehyde + TX, pencycuron (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopyrad + TX, perforazoate + TX, phosphoric acid + TX, polyoxin (654) + TX, polyoxin D zinc salt (654) + TX, potassium bicarbonate + TX, probenazole (658) + TX, procymidone (660) + TX, propamocarb (668) + TX, propineb (676) + TX, proquinazide (682) + TX, prothiocarb (1361) + TX, pyrazophos (693) + TX, pyrifenox (703) + TX, pyroquilon (710) + TX, quinoxifene (715) + TX, quintozene (PCN(B) (716) + TX, siltiofam (729) + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin (744) + TX, sulfur (754) + TX, TCMTB + TX, tecloftalam + TX, tecnazine (TCN(B) (767) + TX, thiabendazole (790) + TX, tifluzamide (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, tolclofos-methyl (808) + TX, tolilfluanid (810) + TX, triazoxide (821) + TX, trichoderma harzianum (825) + TX,tricyclazole (828) + TX, triforine (838) + TX, triphenyltin hydroxide (347) + TX, validamycin (846) + TX, vinclozolin (849) + TX, zineb (855) + TX, ziram (856) + TX, zoxamide (857) + TX, 1 + TX, 1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2 + TX,4-dichlorophenyl benzenesulfonate (IUPAC name / Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N-1naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX,

[076] one compound of the formula B-5.1 + TX, one compound of the formula B-5.2 + TX, one compound of the formula B-5.3 + TX, one compound of the formula B-5.4 + TX, one compound of the formula B-5.5 + TX, one compound of the formula B-5.6 + TX, one compound of the formula B-5.7 + TX, compound B-5.8 + TX, compound B-5.9 + TX, compound B-5.10 + TX, compound B-5.11 + TX, compound B-5.12 + TX, compound B-5.13 + TX, compound B-5.14 + TX, compound B-5.15 + TX, compound B-5.16 + TX, compound B-5.17 from compound B-5.18; 43 / 56

[077] a plant bioregulator selected from the group consisting of

[078] acibenzolar-S-methyl (6) + TX, chlormequat chloride (137) + TX, ethephon (307) + TX, mepiquat chloride (509) and trinexapac ethyl (841);

[079] an insecticide selected from the group consisting of

[080] abamectin (1) + TX, clothianidin (165) + TX, emamectin benzoate (291) + TX, imidacloprid (458) + TX, tefluthrin (769) + TX, thiamethoxam (792) + TX, and glyphosate (419) + TX, a compound of formula V

[081] medosafen + TX, and (B9) isopyrazam + TX, sedaxane + TX, a compound of formula (VI) + TX (VI), and a compound of formula (VII) + TX (VII). Other examples of particularly suitable mixtures selected from the following group Q: 44 / 56 Group Q: compositions particularly suitable according to the invention:

[082] a strobilurin fungicide selected from the group consisting of azoxystrobin + TX, dimoxystrobin + TX, fluoxastrobin + TX, cresoxim-methyl + TX, metominostrobin + TX, orisastrobin + TX, picoxystrobin + TX, pyraclostrobin; trifloxystrobin and a compost of formula B-1.1;

[083] an azole fungicide selected from the group consisting of azaconazole + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazol + TX, diniconazol-M + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazol + TX, flutriafol + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, oxpoconazole + TX, pefurazoate + TX, penconazole + TX, prochloraz + TX, propiconazole + TX, prothioconazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, diclobutrazol + TX, etaconazole + TX, furconazole + TX, furconazole-cis and quinconazole;

[084] a morpholine fungicide selected from the group consisting of aldimorph + TX, dodemorph + TX, fenpropimorph + TX, tridemorph + TX, fenpropidine + TX, spiroxamine + TX, piperaline and a compound of formula B-3.1;

[085] an aniline-pyrimidine fungicide selected from the group consisting of cyprodinil + TX, mepanipyrim and pyrimethanil;

[086] a fungicide selected from the group consisting of benalaxyl + TX, benalaxyl-M + TX, benomyl + TX, bitertanol + TX, boscalid + TX, captan + TX, carboxin + TX, carpropamide + TX, chlorothalonil + TX, copper + TX, cyazofamid + TX, cymoxanil + TX, dietofencarb + TX, dithianon + TX, famoxadone + TX, fenamidone + TX, fenhexamide + TX, fenoxycarb + TX, fenpiclonil + TX, fluazinam + TX, 45 / 56 fludioxonil + TX, flutolanil + TX, folpete + TX, guazatine + TX, himexazol + TX, iprodione + TX, lufenuron + TX, mancozeb + TX, metalaxyl + TX, mefenoxam + TX, metrafenone + TX, nuarimol + TX, paclobutrazol + TX, pencycuron + TX, penthiopyrad + TX, procymidone + TX, proquinazid + TX, pyroquilon + TX, quinoxifen + TX, siltiofam + TX, sulfur + TX, thiabendazole + TX, thiram + TX, triazoxide + TX, tricyclazole + TX, a compound of formula B-5.1 + TX, a compound of formula B-5.2 + TX, a compound of formula B-5.3 + TX, a compound of formula B5.4 + TX, a compound with formula B-5.5 + TX, a compound with formula B-5.6 + TX, a compound with formula B-5.7 + TX, a compound with formula B-5.8 + TX, a compound with formula B-5.9 + TX, a compound with formula B-5.10, and a compound with formula B-5.12;

[087] a plant bioregulator selected from acibenzolar-S-methyl + TX, chlormequat chloride + TX, ethephon + TX, mepiquat chloride and trinexapac ethyl;

[088] an insecticide selected from aabamectin + TX, emamectin + TX, tefluthrin + TX, thiamethoxam + TX, and glyphosate + TX, a compound of formula V (V) + TX, fomesafen + TX, and (B9) isopyrazam + TX, sedaxane + TX, a compound of formula (VI) + TX (VI), and a compound of formula (VII) + TX 46 / 56 ch3(VII).

[089] The mixture of active ingredients of the components of formula I selected from Tables 1 and 2 with active ingredients B described above comprises a compound selected from Tables 1 and 2 and an active ingredient as described above, preferably in a mixing ratio from 1000:1 to 1:1000, especially from 50:1 to 1:50, more especially in a ratio from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, with particular preference given to a ratio from 2:1 to 1:2, and a ratio from 4:1 to 2:1 being equally preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.It is understood that such mixing ratios include, on the one hand, proportions by weight and also, on the other hand, molar proportions.

[090] Mixtures comprising a compound of formula I selected from Tables 1 and 2 and one or more active ingredients as described above may be applied, for example, in a simple “ready-mix” form, in a combined spray mixture prepared from separate formulations of the individual active ingredient components, such as a “tank mix”, and in a combined use of the individual active ingredients when applied sequentially, i.e., one after the other in a period of time. 47 / 56 of a relatively short time, such as a few hours or days. The order of application of the compounds of formula I selected from table 1 and the active ingredients as described above is not essential for the realization of the present invention.

[091] When applied to useful plants, the compound of formula I is applied at a rate of 5 to 2,000 g ai / ha, particularly 10 to 1,000 g ai / ha, for example 50, 75, 100 or 200 g ai / ha, in combination with 1 to 5,000 g ai / ha, particularly 2 to 2,000 g ai / ha, for example 100, 250, 500, 800, 1000, 1500 g ai / ha of a component compound (B), depending on the class of chemical used as component (B).

[092] In agricultural practice, the application rates of the combination according to the invention depend on the type of effect desired, and typically range between 20 and 4,000 g of the total combination per hectare.

[093] When the combinations of the present invention are used for seed treatment, rates of 0.001 to 50 g of a compound of formula I per kg of seeds, preferably 0.01 to 10 g per kg of seeds, and 0.001 to 50 g of a compound of component (B), per kg of seeds, preferably 0.01 to 10 g per kg of seeds, are generally sufficient.

[094] The compositions of the invention can be used in any conventional form, for example, in the form of a double package, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water-dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a granule 48 / 56 a water-dispersible lo (WG), an emulsifiable granule (EG), a water-in-oil emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[095] Such compositions may be produced conventionally, for example, by mixing the active ingredients with appropriate inert formulation agents (diluents, solvents, fillers and, optionally, other formulation ingredients such as surfactants, biocides, antifreeze, adhesives, thickeners and compounds that provide adjuvant effects). Conventional slow-release formulations may also be used where long-lasting efficacy is desired.In particular, formulations to be applied in spray forms, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvant effects, for example, the condensation product of formaldehyde with naphthalene sulfonate, an alkylaryl sulfonate, a lignin sulfonate, an alkyl fatty sulfate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[096] A seed treatment formulation is applied in a manner known per se to the seeds by employing the combination of the invention and a diluent in a suitable seed treatment formulation form, for example, as an aqueous suspension or in a dry powder form having good adherence to the seeds. 49 / 56 tes. Such seed treatment formulations are known in the art. Seed treatment formulations may contain single active ingredients or a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[097] In general, formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of an agriculturally acceptable surfactant and 10 to 99.99% of solid or liquid formulation inerts and adjuvant(s), the active agent consisting at least of the compound of formula I together with a compound of component (B), and optionally other active agents, particularly microbiocides or preservatives or the like. Concentrated forms of the compositions generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of the formulation may, for example, contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. While commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

[098] The following Examples serve to illustrate the invention, wherein active ingredient denotes a mixture of compound I and a compound of component (B) in a specific proportion of the mixture. Formulation Examples Wettable powders: a) b) c) active ingredient [I : comp (B) = 1:3(a), 25% 50% 75% 1:2(b), 1:1(c)] sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% sodium diisobutylnaphthalenesulfonate - 6% 10% 50 / 56 polyethylene glycol phenol ether - 2% (7-8 mol ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27%

[099] The active ingredient is thoroughly mixed with the adjuvants and the mixture is completely ground in a suitable mill, resulting in wettable powders that can be diluted with water. to produce suspensions of the desired concentration. Powders for dry seed treatment a) b) c) active ingredient [I : comp (B) = 1:3(a), 1:2(b), 1:1(c)] 25% 50% 75% light mineral oil 5% 5% 5% highly dispersed silicic acid 5% 5% - Kaolin 65% 40% - Talc - 20

[0100] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, resulting in powders that can be used directly for seed treatment. Emulsifiable concentrate active ingredient (I : comp (B) = 1:6) 10% octylphenol ether of polyethylene glycol 3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3% polyglycol ether of castor oil (35 mol of 4% ethylene oxide) Cyclohexanone 30% mixture of xylenes 50% 51 / 56

[0101] Emulsions of any required dilution, which can be used for plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c) Active ingredient [I : comp (B) = 1:6(a), 1:2(b), 5% 1:10(c)] 6% 4% Talc 95% - - Kaolin - 94% - Mineral filler - - 96%

[0102] Ready-to-use powders are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry coatings for seeds. Extruder granules Active ingredient (I : comp (B) = 2:1) 15% sodium lignosulfonate 2% carboxymethylcellulose 1% Kaolin 82%

[0103] The active ingredient is mixed and ground with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in an air stream. Coated granules Active ingredient (I : comp (B) = 1:10) 8% polyethylene glycol (mol. wt. 200) 3% Kaolin 89%

[0104] The finely ground active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained. Active ingredient suspension concentrate (I : comp (B) = 1:8) 40% 52 / 56 propylene glycol 10% polyethylene glycol nonylphenol ether (15 mol of 6% ethylene oxide) Sodium lignosulfonate 10% carboxymethylcellulose 1% silicone oil (in the form of a 75% emulsion in 1% water) Water 32%

[0105] The finely ground active ingredient is intimately mixed with the adjuvants, giving a concentrated suspension from which suspensions of any desired dilution can be obtained by dilution with water. Using these dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms by spraying, pouring or immersion. Concentrate suitable for flowable seed treatment active ingredient (I : comp (B) = 1:8) 40% propylene glycol 5% butanol PO / EO copolymer 2% tristenephenol with 10-20 moles of EO 2% 1,2-benzisothiazolin-3-one (in the form of a 0.5% solution in water) calcium salt of monoazo pigment 5% Silicone oil (in the form of a 75% emulsion in 0.2% water) Water 45.3%

[0106] The finely ground active ingredient is intimately mixed with the adjuvants, giving a concentrated suspension from which suspensions of any desired dilution can be obtained by dilution with water. Using these dilutions, the plants 53 / 56 live plants as well as plant propagation material can be treated and protected against infestation by microorganisms by spraying, pouring or immersion. Slow-Release Capsule Suspension

[0107] 28 parts of a combination of compound of formula I and a compound of component (B) or of each of these compounds separately, are mixed with 2 parts of an aromatic solvent and 7 parts of a mixture of toluene diisocyanate / polymethylene polyphenyleneisocyanate (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent and 51.6 parts water until the desired particle size is achieved. To this emulsion is added a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water. The mixture is stirred until the polymerization reaction is complete.

[0108] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The average capsule diameter is 8-15 microns.

[0109] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for that purpose. Biological Examples Example B1: Sensitivity of Fusarium virguliforme isolates to compound No. 1001:

[0110] The sensitivity of 4 F. virguliforme isolates to compound No. 1.001 was determined by comparing the inhibition of mycelial growth of potato dextrose on agar plates altered or without compound No. 1.001. Compound No. 1.001 was tested at the following concentrations: 0, 0.001, 0.01, 0.1, 1 and 10 mg ai. / L. The product fludioxonil (commercial formulation Maxim 4 FS) was included in the study. 54 / 56 sensitivity tests. Plates were incubated at 20 °C for 9 days. The sensitivity test was defined in a completely randomized design, with two replicates for each fungicide concentration tested. The data obtained for each isolate were transformed using an arcsine transformation. The effective dose for 50% inhibition of fungal growth (ED50 values) was calculated by regression of the transformed growth inhibition data against the log of the fungicide concentration.

[0111] Compound No. 1001 showed excellent intrinsic activity against F. virguliforme. One isolate was sensitive to fludioxonil. There was no dose response of the other 3 isolates to fludioxonil.

[0112] Table 1. Sensitivity of 4 isolates of F. virguliforme to compound No. 1.001: Composite isolate No. 1.001 ED50 (mg ai / L) Fludioxonil ED50 (mg ai / L) 10-118 0.163 0.206 10-119 0.137 >10 10-120 0.041 >10 10-230 0.117 >10 Example B2: Evaluation of the efficacy of compound No. 1001 against Fusarium virguliforme, the causative agent of sudden death syndrome in soybeans:

[0113] A study was conducted to determine the efficacy of compound No. 1001 against Fusarium virguliforme, the causal agent of soybean sudden death syndrome. Soybean seeds of the cultivar S36B6 were treated with compound No. 1001 at a rate of 5 and 10 grams of active ingredient per 100 kilograms of seeds. The product fludioxonil (commercial formulation Maxim 4 FS) was also included in the test at a rate of 2.5 grams of active ingredient per 100 kilograms of seeds. 55 / 56 lograms of seeds. Ten soybean seeds were placed on a paper towel (Scotts paper towels, 25.4 cm x 33.02 cm in size) that had been previously moistened with 40 milliliters of water. The seeds were inoculated with 100 microliters of a conidial suspension of F. virguliforme adjusted to 100,000 conidia per milliliter of water. In this study, the isolate with the identification number 10-118 of F. virguliforme was used, since it is sensitive to fludioxonil. The inoculated seeds were then covered with another paper towel. Starting from one end, the paper towels with seeds were rolled into a cylindrical shape. The rolled paper towels with the inoculated seeds were placed in a closed plastic bag. The bags were labeled with the fungicide treatment and dated. The bags containing the seeds were then placed in a growth chamber at a temperature of 18 °C and a photoperiod of 12 hours for 19 days.The study was conducted using a completely randomized experimental design with 3 replicates. Disease severity was assessed in the hypocotyls and roots and measured as a percentage. a. The severity of the disease in untreated inoculated plants was 57.9% and was not detected in untreated non-inoculated plants. The disease was completely controlled with compound No. 1001, at rates of 5 and 10 grams of active ingredient per 100 kilograms of seeds. Maxim 4 FS was only able to reduce the severity of the disease to 20.9%.

[0114] Table 2. Control of sudden death syndrome caused by Fusarium verguliforme with compound No. 1001: Fungicide rate mg ai / 100 kg of seed % disease severity ab Average separation c 56 / 56 Fungicide Fungicide rate mg ai / 100 kg of seed % disease severity ab Average separation c Non-inoculated untreated - 0.0 C Inoculated untreated - 57.9 A Fludioxonil (Maxim 4 FS) 2.5 20.9 B Compound No. 1.001 5 0.0 C Compound No. 1.001 10 0.0 C a. Average of 3 repetitions b. % disease severity was performed on hypocotyls and roots c. % averages with a column followed by the same letter are not significantly different (p<0.001)

Claims

1. Method for reducing the occurrence of Fusarium virguliforme phytopathogenic fungi in plants, characterized by comprising applying an effective amount of a composition comprising a compound of formula (I), or a salt, isomer, stereoisomer, diastereoisomer, enantiomer or agrochemically acceptable tautomers thereof, wherein R is methoxy; Q is wherein R1, R2 and R3 are all chlorine; and R8 is hydrogen; to a plant seed before planting, to the soil in which a plant is growing or in which it is desired to grow, to the roots of the plant or to combinations thereof, wherein said plant seed or said plant roots are infected with a Fusarium virguliforme fungal strain.

2. Method according to claim 1, characterized by comprising applying an effective amount of a composition comprising a compound of formula (I) to a plant seed before planting, wherein said plant seed is infected with a fungal strain Fusarium virguliforme.

3. Method for suppressing, controlling or reducing Sudden Death Syndrome in plants, characterized by comprising planting in the soil a plant seed treated with a compound of formula (I), as defined in claim 1, and wherein said plant seeds or soil contain a precursor to Sudden Death Syndrome.

4. Method for reducing damage to a plant or plant seed caused by Sudden Death Syndrome, characterized by comprising applying a compound of formula (I), as defined in claim 1, to a plant seed before planting, wherein said plant seed contains a precursor to Sudden Death Syndrome; and sowing said plant seed.

5. Coated soybean seed characterized by comprising a composition comprising a compound of formula (I), as defined in claim 1, in an amount to reduce the occurrence of Fusarium virguliforme phytopathogenic fungi in plants.