Abstract:
The present invention relates to the use of specific imidazole and/or triazole derivatives for combating pests on plants and/or crops, and/or for preparing a fungicide/insecticide/herbicide/nematicide useful in the treatment of seeds, foliar and/or soil diseases against attacks of pests in plants. A further objective of the present invention is to provide methods of applying said imidazole and/or triazole derivatives in the control of diseases/insects/mites/nematodes and weeds, particularly foliar and/or soil diseases.

Description:
FIELD OF THE INVENTION 
       [0001]    The present invention relates to the use of imidazole and/or triazole derivatives for controlling fungus diseases and combating pests and weeds in the agricultural environment, and/or for preparing a fungicide/insecticide/herbicide/nematicide useful in the treatment of seeds, foliar and/or soil diseases against attacks of pests in plants. 
         [0002]    Damages caused by diseases, pests and weeds to crops, particularly in Brazil, have been generating great losses, proportional to the amount of capital spend in combating them, particularly in view of the increase in plantation areas and the expansion of agriculture in Brazil. Besides, the group of agrochemically effective control agents for combating diseases/pathogens on plants and/or seeds is becoming more and more restrict. 
         [0003]    To give an idea of the magnitude of the losses caused by diseases affecting crops, the so-called “soybean rust”, caused by the fungus  Phakopsora pachyrhizi , has caused great damages to the soybean business. In the latest harvest the values reached the amount around US$ 3 billion, including the expenditure with fungicides for controlling it. 
       PRIOR ART 
       [0004]    The utilization of antifungal agents in agriculture, with pharmaceutical directions for use, indicated for human use, is not novel. Many triazoles were initially discovered and patented for use in antifungal treatment in humans. Later, one realized the importance of this group in controlling diseases of plants, especially cereals, horticulture and fruit growing. 
         [0005]    Application BR 0307334-3 describes the use of alkoxylated amines for enhancing the activity of fungicidal formulations containing triazoles, and also of formulations containing one or more fungicidal triazoles and alcokxylated amines. These formulations are useful for protecting any living or non-living material such as crops, plants, fruits, seeds, objects made of wood, roofs or the like, biodegradable and textile materials, from deterioration due to the action of fungi. 
         [0006]    Document WO 91/01640 describes combined compositions for combating pests on plants, animals and sanitary compositions, for use in forests, horticulture and silos. These compositions contain a pyrethrum-type insecticide with an active insecticidal ingredient and at least one fungicidal ingredient that inhibits the biosynthesis of ergosterol, as an active enhancing agent, as well as, optionally, piperonylbutoxide and other actives. 
         [0007]    Document WO 2004/089396 describes compounds including peptides and peptidomimetics having antifungal activity alone and in combination with other agents that exhibit antifungal activity. 
         [0008]    Document WO 2003/051116 discloses a microencapsulated insecticide that is prepared by oil-in-water interfacial polymerization, said insecticide being solid at room temperature and pressure and having limited solubility ion organic solvents. Various release systems for dispensing the microencapsulated insecticide to a field animal are also described. A preferred release system is an organic dispersion of the microencapsulated insecticide, an oil-in-water emulsion being prepared by emulsifying the product of the oil-in-water interfacial polymerization method to a continuous organic phase. 
         [0009]    Document WO 01/95723 discloses parasiticidal compositions comprising an imidazole and/or triazole and a physiologically acceptable carrier, the imidazole being selected from one or more groups consisting of clotrimazole, ketoconazole and miconazole, and the triazole being selected from one or more groups consisting of fluconazole and itraconazole. 
         [0010]    Document WO 03/007878 discloses sordarin derivatives prepared from C-11-hydroxysordarin as antifungal agents useful in the treatment and/or prevention of infections in humans and animals, as well as in controlling phytopathogenic fungus in plantations. 
         [0011]    Document WO 03/051889 disclose novel solidarin derivatives isolated from fungus culture. The compound is useful ion the treatment and/or prevention of infections in humans and animals, as well as in controlling phytopathogenic fungus in plantations. Two new culture of fungus, ATCC No. PTA-3862 and ATCC No. PTA-3861 may be employed to ferment and produce the compound disclosed in this document. 
         [0012]    Although various methodologies and compositions have been disclosed for the use of imidazole and/or triazole derivatives for fungicidal/insecticidal/herbicidal/nematicidal control in mammals and even in determined agricultural cultivations, there is still the need to create more effective means in the area of agrochemical agents for combating pests on plants. 
         [0013]    Therefore, one of the objectives of the present invention is to provide the use of specific imidazole and/or triazole derivatives for combating pests on plants and/or cultures thereof and/or for preparing a fungicide/insecticide/herbicide/nematicide useful in the treatment of seeds, foliar and/or soil diseases against attacks of pests in plants. 
         [0014]    Another objective of the present invention is to provide methods of applying said imidazole and/or triazole derivatives in the control of diseases/insects/mites/nematodes and weeds, particularly foliar and/or soil diseases. 
     
    
     DETAILED DESCRIPTION OF THE INVENTION 
       [0015]    The present invention discloses the use of specific imidazole and/or triazole derivatives, selected from the group consisting of: 
         [0016]    (i) cis-1-acetyl-4-(4-((2-(2,4-dichloro-phenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxyl)phenyl)piperazine, namely ketoconazole, of the structural formula: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0017]    (ii) alpha-(2,4-difluorophenyl)-alpha-(1H-1,2,4-trizole-1-ylmethyl)-1H-1,2,4-trizole-1-ethanol, namely fluconazole, of structural formula 
         [0000]    
       
                 
         
             
             
         
       
     
         [0018]    (iii) 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl) 3H-1,2,4-triazol-3-one, namely, itraconazole, of structural formula: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0019]    (iv) 4-[2-[(1R,2R)-2-(2,4-difluor-phenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]4-thiazolyl]-benzonitriyl, namely, ravuconazole, of structural formula 
         [0000]    
       
                 
         
             
             
         
       
     
         [0020]    (v) alpha-(2,4-difluorophenyll)-5-fluor-beta-methyl-alpha-(1H-1,2,4-triazol-1-yllmethyl)-(R—(R*,S*))-4-pirimidinetanole, namely voriconazole of structural formula 
         [0000]    
       
                 
         
             
             
         
       
     
         [0021]    (vi) 1-((1S,2S)-1-ethyl-2-hydroxypropyl)-4-{4-[4-(4-{[(5S,3R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazolylmethyll)oxolan-3-yl]methoxy}phenyl)pipera-zinyl]phenyl}-1,2,4-triazolin-5-one, namely, posaconazole, of structural formula 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    and/or mixtures thereof, for treating seeds, foliar and/or soil diseases against attacks of pests in plants, as well as for preparing fungicides/insecticides/herbicides/nematicides useful in the treatment of seeds, foliar and/or soil diseases against attacks of pests in plants. 
         [0022]    The use of fluconazole is particularly preferred. 
         [0023]    The active compounds ketoconazole, fluconazole, itraconazole, voriconazole, ravuconazole and posaconazole, applied either in isolation of in mixture with each other, have a broad spectrum of action as antifungal agents and are also effective for phytopathogenic fungi; particularly for those that belong to the classes of: Deuteromicetos ( Botrytis  spp,  septoria  spp,  Pyricularia  spp,  Stagnospora  spp,  Hetminthosporum  spp,  Fusarium  spp,  Cerospora  spp,  Rhynchosporium  spp,  Alternaria  spp,  Colletotrichum  spp and  Isariopsis  spp); Basidioomicetos ( Phakopsora  spp,  Puccinia  spp,  Rhizoctonia  spp,  U - romyces  spp and  Hemileia  spp); Ascomicetos ( Venturia  spp,  Ppdosphaera  spp,  Erysiphe  spp,  Monilinia  spp and  Uncinula  spp); Oomicetos ( Phytophthora  spp,  Peronospora  spp,  Bremia  spp,  Pythium  spp and  Plasmopara  spp),  Sclerotina  spp,  Alternaria  spp,  Drechslera  spp,  Penicilium  spp e  Apsergillus  spp,  Collectotrichum  spp,  Phomopsis  spp,  Pestalotia  sp and  Ramularia  spp. 
         [0024]    These compounds exhibit healing, preventive and eradicative properties for protecting plants, and may be used for inhibiting or destructing infections caused in an isolated way or concomitantly by fungi on plants or parts thereof (flowers, fruits, tubercles or roots) of different crops. They may also be used for treating plant-propagation material, specially seeds, fruits, tubercles and grains with a view to protect them against soil fungi. Particularly the compositions of the present invention are effective against the attack by  Phakopsora pachyrhizi, Pyricularia  ssp,  Helminthosporium  spp,  Fusarium  ssp,  Septoria  spp,  Cercospora  ssp,  Rhynchosporium  spp,  Collectotrichum  spp,  Pythium  spp,  Phomopsis  spp,  Phytophthora  spp,  Peronospora  spp,  Pestalotia  spp,  Sclerotina  spp,  Alternaria  spp,  Drechslera  spp,  Penicilium  spp,  Apsergillus  spp or  Ramularia  spp. 
         [0025]    Based on the spectrum of activity, the active compounds of the present invention may be used for protecting or eradicating phytopathogenic fungi, which affect various crops. The species of crops that can be embraced by the scope of protection of the present invention may be selected from: cereals (wheat, rye, oats, barley, rice, transgenic rice, mutagenic rice and sorghum); fruits (apple, pear, peach, strawberry, mulberry, citrus, mango, papaya, banana, grape); leguminous plants (beans, transgenic beans, soybeans, peas, transgenic soybeans); oleaginous plants (canola, sunflower, coconut), cucurbitaceous (cucumber, pumpkin, melon and water-melon); fibrous plants (cotton, transgenic cotton and jute); vegetables (lettuce, cabbage, spinach, carrot, asparagus, onion, garlic, tomato, potato) or plants such as corn, transgenic corn, tobacco, coffee, sugar-cane, tea, rubber tree, eucalyptus, pinus, as well as ornamental plants (flowers). Particularly, crops of wheat, soybean, rice, cotton and potato are preferred. However, this list does not constitute any limit for the non-mentioned species, especially as far as the spectrum of activity of the active cited compounds is concerned. 
         [0026]    The method of controlling diseases/insects/mites/nematodes and weeds, particularly foliar diseases and/or soil diseases, according to the pre-sent invention, comprise the preventive and/or healing treatment and/or the application of effective amounts of said imidazole and/or triazole derivatives to the place (crop of target) to be protected and/or to the insect of pest itself. The ranges employed vary according to the crop. For the treatment of seeds, one recommends from 5 to 500 grams of the active compound(s) for 100 kg of seed. For foliar treatment, each crop requires a specific dose of the active compound(s), generally from 20 to 500 grams of the active compound(s) per hectare. For use in the soil, the amount may range from 100 to 500 grams of active compound(s) per hectare. 
         [0027]    The illustrative examples given hereinafter will serve for describing the invention in a better way. However, the formulations described herein merely refer to some embodiments of the present invention and do should not be taken as being limitative of the scope of the invention. 
       EXAMPLE 1 
       [0028]    Recent tests carried out in greenhouses the laboratory of FMC Quimica do Brasil Ltda. in Uberaba, MG, Brazil, show the highly fungicidal effect of said specific imidazole and/or triazole derivatives in combating diseases of plants, particularly against the attack by the fungus  Phakopsora pachyrhizi  on soybeans, as described hereinafter. 
       i) Active Compound: Ketoconazole 
     Materials and Methods 
       [0029]    Crop: soybeans 
         [0030]    Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants 
         [0031]    Time of Application of the Active Compound: 
         [0032]    a) Preventive Mode: 40 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0033]    b) Healing Mode: 40 days after plantation of the soybeans in 2-liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0034]    Equipment: a manual sprayer commonly used in agriculture with 2-litre capacity. 
         [0035]    Dosages: 200 to 500 grams per hectare of the active compound ketoconazole per liter diluted in water. 
         [0036]    Evaluation of the Effectiveness of the Product: The evaluations were made every 5 days after application of the product, in a total of 4 evaluations. As an evaluation parameter, one has utilized the severity of the disease (percentage of the foliar area attacked by the rust) according to the Diagrammatic Scale for Evaluation of Severity of Soybean Rust—Embrapa, Centro Nacional de Pesquisa de Soja (CNPSo) (=National Center for Soybean Research), in Londrina, PR, Brazil ( FIG. 1 ). 
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 1 
               
             
             
               
                   
               
               
                 Response of Doses of Ketoconazole for Control of the “Soybean Rust” 
               
             
          
           
               
                   
                 DOSAGES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENT 
                 (g ac/ha) 
                 5 DAT* 
                 10 DAT 
                 5 DAT 
                 20 DAT 
               
               
                   
               
             
          
           
               
                 Ketoconazole 
                 100 
                 15 
                 20 
                 27 
                 45 
               
               
                 ketoconazole 
                 200 
                 5 
                 8 
                 10 
                 18 
               
               
                 ketoconazole 
                 300 
                 3 
                 6 
                 10 
                 16 
               
               
                 ketoconazole 
                 400 
                 3 
                 7 
                 11 
                 15 
               
               
                 ketoconazole 
                 500 
                 2 
                 4 
                 8 
                 11 
               
               
                 Blank 
                 — 
                 33 
                 49 
                 67 
                 79 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0037]    Ketoconazole, from the dose of 200 grams of active ingredients per hectare (Table 1), imparts effectiveness for controlling soybean rust and exhibited potential to be used as an alternative in controlling soybean rust. 
       ii) Active Compound: Fluconazole 
     Materials and Methods 
     Crop: Soybean 
       [0038]    Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants. 
         [0039]    Time of Application of the Active Compound: 
         [0040]    a) Preventive Mode: 40 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0041]    b) Healing mode: 40 days after plantation of the soybeans in 2 liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0042]    Equipment: a manual sprayer commonly used in agriculture with 2-liter capacity. 
         [0043]    Dosages: 50 to 500 grams per hectare of the active compound Fluconazole per liter diluted in water. 
         [0044]    Evaluations of the Effectiveness of the Product: The evaluations were made every 5 days after application of the product, in a total of 4 evaluations. As an evaluation parameter one utilized the severity of the disease (percentage of foliar area attacked by rust) according to the diagrammatic scale of the EMBRAPA ( FIG. 1 ). 
       Results 
       [0045]      
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 2 
               
             
             
               
                   
               
               
                 Response of Doses of Fluconazole for Control of Soybean Rust 
               
             
          
           
               
                   
                 DOSES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENTS 
                 (g ac/ha) 
                 5 DAT* 
                 10 DAT 
                 15 DAT 
                 20 DAT 
               
               
                   
               
             
          
           
               
                 Fluconazole 
                  50 
                 5 
                 10 
                 12 
                 12 
               
               
                 Fluconazole 
                 100 
                 5 
                 7 
                 10 
                 11 
               
               
                 Fluconazole 
                 150 
                 4 
                 6 
                 9 
                 10 
               
               
                 Fluconazole 
                 250 
                 3 
                 7 
                 11 
                 10 
               
               
                 Fluconazole 
                 500 
                 0 
                 0 
                 2 
                 4 
               
               
                 Blank 
                 — 
                 34 
                 48 
                 88 
                 75 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0046]    Fluconazole, from 50 grams of active ingredients per hectare (Table 2) proved to be effective in controlling soybean rust and exhibited potential for use as a fungicide in controlling this disease. 
         [0000]    iii) Active Compound: Itraconazole 
       Materials and Methods 
       [0047]    Crop: soybean 
         [0048]    Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants. 
         [0049]    Time of Application of the Active Compound: 
         [0050]    a) Preventive Mode: 40 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0051]    b) Healing mode: 40 days after plantation of the soybeans in 2-liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V6 stage with seven expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0052]    Equipment: a manual sprayer commonly used in agriculture with 2-liter capacity. 
         [0053]    Dosages: 50 to 500 grams per hectare of the active compound Itraconazole per liter diluted in water. 
         [0054]    Evaluations of the Effectiveness of the Product: The evaluations were made every 5 days after application of the product, in a total of 4 evaluations. As an evaluation parameter one utilized the severity of the disease (percentage of foliar area attacked by rust) according to the diagrammatic scale of the EMBRAPA ( FIG. 1 ). 
       Results 
       [0055]      
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 3 
               
             
             
               
                   
               
               
                 Response of Doses of Itraconazole for Control of Soybean Rust 
               
             
          
           
               
                   
                 DOSES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENTS 
                 (g ac/ha) 
                 5 DAT* 
                 10 DAT 
                 15 DAT 
                 10 DAT 
               
               
                   
               
             
          
           
               
                 Itraconazole 
                  50 
                 6 
                 10 
                 11 
                 12 
               
               
                 Itraconazole 
                 100 
                 5 
                 8 
                 10 
                 13 
               
               
                 Itraconazole 
                 150 
                 5 
                 8 
                 10 
                 13 
               
               
                 itraconazole 
                 250 
                 3 
                 5 
                 10 
                 14 
               
               
                 itraconazole 
                 500 
                 0 
                 2 
                 0 
                 10 
               
               
                 Blank 
                 — 
                 29 
                 51 
                 54 
                 75 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0056]    Itraconazole, from 50 grams of active ingredient per hectare (Table 3) proved to be effective in controlling soybean rust and exhibited potential for use as a fungicide in controlling this disease. 
       iv) Active Compound: Ravuconazole 
     Materials and Methods 
     Crop: Soybean 
       [0057]    Experimental Outline Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants. 
       Time of Application of the Active Compound: 
       [0058]    a) Preventive Mode: 30 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0059]    b) Healing mode: 30 days after plantation of the soybeans in 2-liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0060]    Equipment: a manual sprayer commonly used in agriculture with 2-liter capacity. 
         [0061]    Dosages: 50 to 300 grams per hectare of the active compound Itraconazole per liter diluted in water. 
         [0062]    Evaluations of the Effectiveness of the Product: The evaluations were made every 7 days after application of the product, in a total of 4 evaluations. As an evaluation parameter one utilized the severity of the disease (percentage of foliar area attacked by rust) according to  FIG. 1 ). 
       Results 
       [0063]      
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 4 
               
             
             
               
                   
               
               
                 Response of Doses of Ravuconazole for Control of Soybean Rust 
               
             
          
           
               
                   
                 DOSES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENTS 
                 (g ca/ha) 
                 7 DAT* 
                 14 DAT 
                 21 DAT 
                 28 DAT 
               
               
                   
               
             
          
           
               
                 Ravuconazole 
                  50 
                 15 
                 16 
                 16 
                 18 
               
               
                 Ravuconazole 
                 100 
                 12 
                 12 
                 14 
                 18 
               
               
                 Ravuconazole 
                 150 
                 9 
                 11 
                 11 
                 16 
               
               
                 Ravuconazole 
                 200 
                 3 
                 7 
                 11 
                 15 
               
               
                 Ravuconazole 
                 300 
                 2 
                 3 
                 9 
                 11 
               
               
                 Blank 
                 — 
                 36 
                 48 
                 59 
                 69 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0064]    Ravuconazole, from 50 grams of active ingredient per hectare (Table 4) proved to be effective ion controlling soybean rust and exhibited potential for use as a fungicide in controlling this disease. 
       v) Active Compound: Voriconazole 
     Materials and Methods 
     Crop: Soybean 
       [0065]    Experimental Outline Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants. 
       Time of Application of the Active Compound: 
       [0066]    a) Preventive Mode: 30 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0067]    b) Healing mode: 30 days after plantation of the soybeans in 2-liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0068]    Equipment: a manual sprayer commonly used in agriculture with 2-liter capacity. 
         [0069]    Dosages: 50 to 300 grams per hectare of the active compound Itraconazole per liter diluted in water. 
         [0070]    Evaluations of the Effectiveness of the Product: The evaluations were made every 7 days after application of the product, in a total of 4 evaluations. As an evaluation parameter one utilized the severity of the disease (percentage of foliar area attacked by rust) according to  FIG. 1 ). 
       Results 
       [0071]      
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                 Response of Doses of Voriconazole for Control of Soybean Rust 
               
             
          
           
               
                   
                 DOSES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENTS 
                 (g ac/ha) 
                 7 DAT* 
                 14 DAT 
                 21 DAT 
                 28 DAT 
               
               
                   
               
             
          
           
               
                 Voriconazole 
                  50 
                 8 
                 10 
                 10 
                 13 
               
               
                 Voriconazole 
                 100 
                 8 
                 8 
                 11 
                 18 
               
               
                 Voriconazole 
                 150 
                 8 
                 8 
                 10 
                 18 
               
               
                 Voriconazole 
                 200 
                 4 
                 7 
                 11 
                 11 
               
               
                 Voriconazole 
                 300 
                 2 
                 0 
                 1 
                 5 
               
               
                 Blank 
                 — 
                 33 
                 50 
                 68 
                 74 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0072]    Voriconazole, from 50 grams of active ingredient per hectare (Table 5) proved to be effective in controlling soybean rust and exhibited potential for use as a fungicide in controlling this disease. 
       v) Active Compound: Voriconazole 
     Materials and Methods 
     Crop: Soybean 
       [0073]    Experimental Outline Experimental Outline: entirely made with five repetitions, two plants per repetition, totaling 10 plants. 
       Time of Application of the Active Compound: 
       [0074]    a) Preventive Mode: 30 days after plantation of the soybeans in plastic 2-liter pots and with corresponding volumes of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, the compounds were sprayed and then, 48 hours afterwards, inoculation of the rust was effected. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0075]    b) Healing mode: 30 days after plantation of the soybeans in 2-liter plastic pots and with a corresponding volume of soil, the soybean plants were at the V5 stage with six expanded folioles. At this moment, one effected the inoculation of the rust and then, 48 hours afterwards, the compounds were sprayed. To effect the inoculation, one prepared a suspension of  Phakopsora  uredospores at the concentration of 2×10 4  spores/milliliters. 
         [0076]    Equipment: a manual sprayer commonly used in agriculture with 2-liter capacity. 
         [0077]    Dosages: 50 to 300 grams per hectare of the active compound Voriconazole per liter diluted in water. 
         [0078]    Evaluations of the Effectiveness of the Product: The evaluations were made every 7 days after application of the product, in a total of 4 evaluations. As an evaluation parameter one utilized the severity of the disease (percentage of foliar area attacked by rust) according to  FIG. 1 ). 
       Results 
       [0079]      
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 6 
               
             
             
               
                   
               
               
                 Response of Doses of Posaconazole for Control of Soybean Rust 
               
             
          
           
               
                   
                 DOSES 
                 SEVERITY OF RUST (% IFA**) 
               
             
          
           
               
                 TREATMENTS 
                 (g ac/ha) 
                 7 DAT* 
                 14 DAT 
                 21 DAT 
                 28 DAT 
               
               
                   
               
             
          
           
               
                 Posaconazole 
                  50 
                 11 
                 13 
                 15 
                 14 
               
               
                 Posaconazole 
                 100 
                 5 
                 8 
                 12 
                 13 
               
               
                 Posaconazole 
                 150 
                 0 
                 6 
                 9 
                 12 
               
               
                 Posaconazole 
                 200 
                 3 
                 0 
                 6 
                 9 
               
               
                 Posaconazole 
                 300 
                 0 
                 0 
                 3 
                 7 
               
               
                 Blank 
                 — 
                 16 
                 54 
                 64 
                 75 
               
               
                   
               
               
                 *DAT = Days after treatment 
               
               
                 **IFA = Infected foliar area 
               
             
          
         
       
     
         [0080]    Pozaconazole, from 50 grams of active ingredient per hectare (Table 6) proved to be effective in controlling soybean rust and exhibited potential for use as a fungicide in controlling this disease. 
       EXAMPLE 2 
       [0081]    The following tests aim at testing the efficiency of compounds Ketoconazole (indicated as compound FF-4800), Fluconazole (indicated as compound FF-4900) and Itraconazole (indicated as compound FF-4901) against pests selected from  Phakopsora pachyrhizi, Pyricularia  ssp,  Helminthosporium  spp,  Fusarium  ssp,  Septoria  spp,  Cercospora  ssp,  Rhynchosporium  spp,  Collectotrichum  spp,  Pythium  spp,  Phomopsis  spp,  Phytophthora  spp,  Peronospora  spp,  Pestalotia  spp,  Sclerotina  spp,  Alternaria  spp,  Drechslera  spp,  Penicilium  spp,  Apsergillus  spp and  Ramularia  spp in crops of wheat, soybean, rice, cotton and potato. 
         [0082]    Objectives (see  FIGS. 2A and 2B ) 
         [0083]    Test in vitro—1 st  step; 
         [0084]    Tests in vitro with defined crops—2 nd  step; 
         [0085]    To optimize tests in vivo:
       (i) tests in greenhouse;   (ii) stability of formulations in planta;   (iii) phytotoxicity tests of formulations;   (iv) potentiality tests for TS.       
 
       Methodology 
       [0090]    Tests in vitro in laboratory (see  FIGS. 3A and 3B ): 
         [0091]    Preparing the solution:
       Dissolution;   Dillution.       
 
         [0094]    Culturing the phytyopathogens (BDA) 
         [0095]    Tests in vitro in greenhouse (see  FIGS. 5A and 5C ): 
         [0096]    Collecting the uredospores directly from the infected leaves (see  FIG. 5A ); 
         [0097]    Microspraying spores (see  FIG. 5B );
       CO 2  propelled;   Possibility of adjusting the amount of sprayed liquid (suspension of inoculus and fungicide broth)       
 
         [0100]    Microsprayer: directed jet (see  FIG. 5C ) 
         [0101]    Tests in vivo: 
         [0102]    Action is spores; 
         [0103]    Preventive/curative action; 
         [0104]    Methodology. 
         [0105]    Preparing the solution 
         [0106]    Dissolution:
       FF4800       
 
         [0108]    Weighted (0.1205 g); 
         [0109]    Dissolved in 20 mL of pure methanol; 
         [0110]    Dilluted in 80 mL of distilled water; 
         [0111]    Stock solution in the concentration of 1000 ppm.
       FF4900       
 
         [0113]    Weighted (0.1205 g); 
         [0114]    Dissolved in 20 mL of pure methanol; 
         [0115]    Dilluted in 80 mL of distilled water; 
         [0116]    Stock solution in the concentration of 1000 ppm.
       FF4901       
 
         [0118]    Weighted (0.4545 g); 
         [0119]    Dissolved in 40 mL of a 50% acetic acid/50% distilled water solution, plus 20 mL of pure methanol; 
         [0120]    Dilluted in 40 mL of distilled water, with the aid of ultrasound (15 min); 
         [0121]    Stock solution in the concentration of 1000 ppm. 
         [0122]    Inhibition Index 
         [0123]    Relationship between the fungi growing area in the solvent alone, blank (agar) and product+solvent; 
         [0124]    The higher the inhibition index, the higher the efficiency of the product. 
         [0000]    The inhibition index results are shown in  FIGS. 4A to 4X .
 
Results of the 2 nd  step with defined crops (Evaluation of efficiency of fungicides for controlling soybean asian rust caused by  Phakopsora pachyrhizi  in the State of Mato Grosso, Brazil)
 
       Materials and Methods 
       [0125]    Several fungicides were evaluated in the control of soybean asian rust (Table 1A). The experiment was effected in Rondonópolis, MT, Brazil, harvest 2005/06, in a commercial area with soybean cultivar. The experiment consisted of 13 treatments (Table 1A). 
         [0000]    
       
         
               
             
               
               
             
               
               
               
               
             
           
               
                 TABLE 1A 
               
             
             
               
                   
               
               
                 Characterization of the evaluated fungicides and doses in the 
               
               
                 control of the soybean asian rust, Rondonópolis, MT, Brazil. 
               
             
          
           
               
                 Treatments 
                 Dose 
               
             
          
           
               
                 Trade Name 
                 Common Name 
                 i.a g ha −1   
                 P.C. mL ha −1   
               
               
                   
               
               
                 Domark + Derosal 
                 Tetraconazole + 
                  50 + 250 
                 500 + 500 
               
               
                   
                 Carbendazin 
               
               
                 Domark + Derosal 
                 Tetraconazole + 
                  40 + 200 
                 400 + 400 
               
               
                   
                 Carbendazin 
               
               
                 Domark 
                 Tetraconazole 
                 50 
                 500 
               
               
                 Elite + Derosal 
                 Tebuconazole + 
                 100 + 250 
                 500 + 500 
               
               
                   
                 Carbendazin 
               
               
                 Elite 
                 Tebuconazole 
                 100 
                 500 
               
               
                 Opera 
                 Pyraclostrobin + 
                 66.5 + 25   
                 500 
               
               
                   
                 Epoxiconazole 
               
               
                 PrioriXtra 
                 Azoxystrobin + 
                 60 + 24 
                 300 
               
               
                   
                 Cyproconazole 
               
               
                 Impact 
                 Flutriafol 
                 62.5 
                 500 
               
               
                 FF-4900 
                 — 
                 — 
                 500 
               
               
                 FF-4900 
                 — 
                 — 
                 750 
               
               
                 FF-4900 
                 — 
                 — 
                 1000 
               
               
                 FF-4800 
                 — 
                 — 
                 1000 
               
               
                 Blank 
                 — 
                 — 
                 — 
               
               
                   
               
             
          
         
       
     
         [0126]    The experimental outlining was random, in blocks, with 13 treatments and 4 repetitions. Each plot consisted of 6 lines of 6 m, spaced 0.45 m. 
         [0127]    The culture traits were suited to the good development of the soybean crop, uniformly applied in the whole experiment. 
         [0128]    The spraying was effected in stadiums R3 and R5.1, with coast CO 2  sprayer provided with a JA-02-type beak, under a pressure of 0.31 MPa (45 psi), using 110 L of broth per ha. At the first application, the plants were presenting the beginning of rust symptoms at their foliar areas. 
         [0129]    The rust was evaluated by analysing the percentage of foliar area affected by the disease, according to Godoy et al., in the plants of the three central lines. Evaluationa related to soybean injury and severity were effected in 14 and 21 days after the first application (DDA), by means of visual observation of the leaves of the plot plants. 
       Results 
       [0130]    The results are shown in Table 2A. 
         [0000]    
       
         
               
             
               
               
             
               
               
               
               
             
               
               
               
               
             
           
               
                 TABLE 2A 
               
             
             
               
                   
               
               
                 Effect of fungicides, evaluated in 14 and 21 days after the first 
               
               
                 application, on the severity caused by the soybean rust 
               
               
                 ( Phakopsora pachyrhizi ), Rondonópolis, MT, Brazil. 
               
             
          
           
               
                   
                 Severity - affected foliar 
               
               
                 Treatments 
                 area (%) 
               
             
          
           
               
                 Trade Name 
                 Dose (P.C. mL ha −1 ) 
                 14 DAA 
                 21 DAA 
               
               
                   
               
             
          
           
               
                 Domark + Derosal 
                 500 + 500 
                 0.3 
                 0.9 
               
               
                 Domark + Derosal 
                 400 + 400 
                 0.4 
                 1.5 
               
               
                 Domark 
                 500 
                 0.3 
                 1.0 
               
               
                 Elite + Derosal 
                 500 + 500 
                 0.3 
                 0.9 
               
               
                 Elite 
                 500 
                 0.3 
                 0.9 
               
               
                 Opera 
                 500 
                 0.5 
                 2.0 
               
               
                 PrioriXtra 
                 300 
                 0.6 
                 2.0 
               
               
                 Impact 
                 500 
                 0.3 
                 1.1 
               
               
                 FF-4900 
                 500 
                 0.6 
                 4.0 
               
               
                 FF-4900 
                 750 
                 0.5 
                 2.0 
               
               
                 FF-4900 
                 1000 
                 0.4 
                 1.5 
               
               
                 FF-4800 
                 1000 
                 2.0 
                 7.0 
               
               
                 Blank 
                 — 
                 8.3 
                 19.2 
               
               
                   
               
             
          
         
       
     
         [0131]    Examples of embodiment having been described, it should be understood that the present invention embraces other configurations, being limited only by the scope of the accompanying claims.