Patent Publication Number: US-6699874-B2

Title: Fungicidal mixtures

Description:
CROSS-REFERENCE TO RELATED APPLICATION(S) 
     This is a Divisional of application Ser. No. 09/809,512, filed Mar. 15, 2001, now U.S. Pat. No. 6,518,275 which is a dicisional of application Ser. No. 09/404,910, filed Sep. 24, 1999 (U.S. Pat. No. 6,277,856 B1), the entire disclosure of which is hereby incorporated by reference. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates to a fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent and synergistically effective amounts of 
     (a) at least one azolopyrimidine of formula I                    
      in which 
     R 1  represents a C 1-6  alkyl, C 3-6  alkenyl or C 1-6  haloalkyl group, or 
     R 2  represents a hydrogen atom or a C 1-6  alkyl group, or 
     R 1  and R 2  taken together represent a C 1-6  alkylene group, 
     L 1  represents a halogen atom; 
     L 2  and L 3  each independently represent a hydrogen or a halogen atom; and 
     and at least one fungicidal active ingredient selected from the following classes (A), (B) and (C): 
     (A) a compound selected from the group consisting of benomyl, carboxin, captan, chlorothalonil, copper oxychloride, cyprodinil, dimethomorph, dithianon, dodine, famoxadone, fenpiclonil, fenpropimorph, fluazinam, mancozeb, metalaxyl, pyrimethanil, quinoxifen, sulfur, triforine and vinclozolin; 
     (B) a fungicidal triazole derivative; and 
     (C) a synthetic strobilurine derivative. 
     The fungicidal compounds of formula I to be used according to the present invention are known from U.S. patent U.S. Pat. No. 5,593,996. The compounds of the classes (A) and (B) are known from “The Pesticide Manual”, 11 th  edition (1997), Editor Clive Tomlin. Fenhexamid is known from AGROW No. 287, p. 21. The synthetic strobilurines are known, for example, from WO 92/08703, EP 0 253 213 and EP 0 398 692. 
     However, none of the above mentioned prior art references teaches a combination of compounds of formula I with any of the fungicidal active ingredients selected from the classes (A), (B) and (C) as described above, nor that such mixtures show synergistic effects and can advantageously be used for controlling diseases such as wheat powdery mildew, barley powdery mildew, wheat leaf rust, barley net blotch and wheat Septoria leaf blotch, Botrytis diseases and others. 
     Surprisingly, when compounds of formula I were tank mixed with compounds from classes (A), (B) and (C) and used in greenhouse and field trials, a synergistic increases in activity were observed, compared to the activity expected based on the activities of the individual active ingredients. 
     A mixture of fungicides shows synergistic effect if the fungicidal activity of the mixture is larger than the sum of activities of the separately applied compounds. The expected fungicidal activity for a given mixture of two fungicides can also be calculated as follows (See Colby, S. R., “Calculating synergistic and antagonistic response of herbicide combinations”, Weeds 15, pp 20-22 (1967): 
     
       
           EE=x+y−x·y /100 
       
     
     wherein 
     x is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient A at a dose rate a; 
     y is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient B at a dose rate b; 
     EE is the expected efficacy with a combination of fungicidal active ingredients A and B at a dose of a+b, respectively. 
     If the actual efficacy (E) exceeds the expected (calculated) one (EE), the mixture displays a synergistic effect. 
     SUMMARY OF THE INVENTION 
     The present invention includes a fungicidal composition comprising an acceptable carrier and/or surface active agent and synergistically effective amounts of at least one compound of formula I, and at least one fungicidal active ingredient selected from the following classes (A), (B) and (C): 
     (A) a compound selected from the group consisting of benomyl, carboxin, captan, chlorothalonil, copper oxychloride, cyprodinil, dimethomorph, dithianon, dodine, famoxadone, fenpiclonil, fenpropimorph, fluazinam, mancozeb, metalaxyl, pyrimethanil, quinoxifen, sulfur, triforine and vinclozolin; 
     (B) a fungicidal triazole derivative; and 
     (C) a synthetic strobilurine derivative. 
     The present invention also includes a method of controlling the growth of phytopathogenic fungi at a locus which comprises applying synergistically effective amounts of at least one azolopyrimidine of formula I and at least one fungicidally active ingredient selected from classes (A), (B) and (C) defined above to the locus. 
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     Preferred compounds of formula I are those wherein 
     R 1  and R 2  together with the interjacent nitrogen atom represent a 4-methylpiperidine ring, or wherein 
     R 1  represents a C 1-6  alkyl, in particular an isopropyl group, a C 1-6  haloalkyl, in particular a 2,2,2-trifluoroethyl or a 1,1,1-trifluoroprop-2-yl group, or a C 3-8  cycloalkyl group, in particular a cyclopentyl or cyclohexyl group and R 2  represents a hydrogen atom, and/or 
     wherein L 1  represents a fluorine or chlorine atom and L 2  and L 3  each independently represent a hydrogen atom or a fluorine atom, in particular 
     wherein L 1  represents fluorine, L 2  represents hydrogen and L 3  represents chlorine or wherein L 1  through L 3  represent fluorine. 
     Particularly preferred are the following azolopyrimidines: 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine A, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine B and 5-chloro-6-(2,4,6-trifluorophenyl)-7-(1,1,1-trifluoroprop-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine C. Azolopyrimidine C due to the chirality of its 1,1,1-trifluoroprop-2-yl group may be applied as a racemic mixture or in the form of an enantiomeric enriched compound, in particular as (S)-enantiomer coded (S)-Azolopyrimidine C. 
     Preferred triazole derivatives in the practice of this invention are the compounds of formula II,                    
     wherein 
     L represents a linking group selected from the groups (a), (b), (c) and (d)                    
      in which 
     X 1  represents an alkyl or an optionally substituted phenyl group; 
     X 2  and X 3  each independently represent a hydrogen atom or an alkyl group; 
     X 4  represents an alkyl or cyclopropylalkyl group; 
     q is 1 or 2; and 
     n is 0 or 2. 
     Particularly preferred are the triazoles selected from the group consisting of cyproconazole, epoxiconazole, metconazole, propiconazole and tebuconazole. 
     Preferred strobilurine derivatives in the practice of this invention are the compounds of formula III,                    
     wherein 
     A represents N or CH; 
     B represents a —O—, —OCH 2 —, a —CH 2 O—, a pyrimid-4,6-dioxydiyl group or a group of formula                    
     R 3  represents a C 1-4  alkyl group; 
     R 4  represents a C 1-6  alkoxy or a C 1-6  alkylamino group; 
     R 5  represents a hydrogen or halogen atom or a cyano, a C 1-4  alkyl or a C 1-4  haloalkyl group; and 
     m is 0, 1 or 2; 
     in particular azoxystrobin, kresoxim methyl, CGA-279202 (AGROW 279, p.17 1998) or SSF126 (Pesticide Manual, loc. cit., page 1114) 
     Preferred compositions of this invention comprise the following constituents: 
     a carrier agent; 
     at least one azolopyrimidine of formula I, 
     at least one compound selected from the classes (A), (B) and (C) as defined above; 
     optionally an adjuvant selected from the group consisting of polyalkoxylated alcohols, triglycerides and amines, in particular Synperonic 91-6, which is commercially available from ICI Surfactants; 
     optionally a foam breaking agent, in particular a mixture of perfluoroalkyphosphonic acids and/or perfluoroalkylphosphinic acids, in particular Defoamer SF or Fluowett PL, which are commercially available from Clariant GmbH. 
     The compound of formula I and the compound selected from the classes (A), (B) and (C) as defined above are to be applied together, in synergistically effective amounts. These synergistic mixtures exhibit an extraordinary efficacy against a broad range of phytopathogenic fungi, in particular against fungi from the classes ascomycetes, basidiomycetes, oomycetes and deuteromycetes. Therefore, they can be applied advantageously against a broad range of diseases in different crops. They may be applied as leaf, stem, root, into-water, seed dressing, nursery box or soil fungicides. 
     The composition according to the invention may be preferably applied for controlling phytopathogenic fungi of the genera: Achlya, Alternaria, Balansia, Bipolaris, Blumeria (Erysiphe), Cercospora, Cochliobolus, Curvularia, Cylindrocladium, Drechslera, Entyloma, Fusarium, Gaeumannomyces, Gerlachia, Gibberella, Guignardia, Leptosphaeria, Magnaporthe, Mucor, Mycosphaerella, Myrothecium, Nigrospora, Peronospora, Phoma, Pseudoperonospora, Pseudocercosporella, Phytophthora, Puccinia, Pyricularia, Pythium, Rhizoctonia, Rhizopus, Sarocladium, Sclerophthora, Sclerotium, Septoria, Tilletia, Uncinula, Ustilago, Ustilaginoidea, and Venturia, in particular the species  Blumeria graminis  f. sp. tritici,  Botrytis cinerea, Septoria tritici Erysiphe cichoracearum  and  Puccinia recondita.    
     The compositions according to the invention are preferably applied for controlling the above phytopathogenic fungi on monocotylydoneous plants, such as barley and wheat, rice and turf grases, or fruit crops such as pomefruits, stonefruits and vines, as well as all kinds of vegetables, oil and oil seed crops, and ornamentals. 
     The application rate of the compound of formula I according to this invention is suitably in the range of 1 to 2000 grams of active ingredient (g a.i.) per hectare, with rates between 20-500 g a.i./ha often achieving satisfactory control. The optimal rate for a specific application will depend on the crop(s) under cultivation and the predominant species of infesting fungi, and readily may be determined by established biological tests known to those skilled in the art. 
     In general, the preferred application rate of the compounds of formula I is in the approximate range of 10 to 500 g a.i./ha, more preferably 20-300 g a.i./ha. 
     The optimal rate for the compounds of classes (A), (B) and (C), will, however, depend on the crop(s) under cultivation and the level of infestation by the fungus, and can readily be determined by established biological tests. 
     The approximate ratio (by weight) of the compound of formula I to the fungicidal active ingredient of the classes (A), (B) and (C) is suitably from 1:100 to 100:1. The preferred ratio formula I: (A), (B) or (C) may vary, e.g., from about 1:50 to about 50:1, in particular from about 1:4 to about 4:1, most preferably from 1:1.5 to 1.5:1. 
     The active compounds can be co-formulated together in a suitable ratio according to the present invention, together with carriers and/or additives known in the art. 
     A method of making such a composition is also provided which comprises bringing the compound of formula I and the fungicidal active ingredient selected from the classes (A), (B) and (C) as defined above into association with at least one carrier. It is also envisaged that different isomers or mixtures of isomers of formula I and/or the fungicidal active ingredient selected from the classes (A), (B) and (C) may have different levels or spectra of activity and thus compositions may comprise individual isomers or mixtures of isomers. 
     A composition according to the invention preferably contains from 0.1% to 99.9%, preferably 0.2 to 80% by weight (w/w) of active ingredients. 
     A carrier in a composition according to the invention may be any material with which the active ingredients may be formulated to facilitate application to the locus to be treated (which may, for example, be a plant, seed, foliage, soil, or into the water where the plant grow or to the roots), or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including material which is normally a gas but which has been compressed to form a liquid. 
     The compositions may be manufactured into, e.g., emulsion or emulsifiable concentrates, solutions, oil in water emulsions, wettable powders, soluble powders, suspension concentrates, dusts, granules, aerosols, water dispersible granules, tablets, micro-capsules, gels and other formulation types by well-established procedures. These procedures may include intensive mixing and/or milling of the active ingredients with other substances, such as fillers, solvents, solid carriers, surface active compounds (surfactants), and, optionally solid and/or liquid auxilaries and/or adjuvants. The form of application such as spraying, atomizing, dispersing or pouring may be chosen like the compositions according to the desired objectives and the given circumstances. 
     Solvents used in the composition of this invention may be aromatic hydrocarbons, e.g. Solvesso® 200, substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, alcohols and glycols as well as their ethers and esters, e.g. ethanol, ethyleneglycol mono- and dimethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, or γ-butyrolactone, higher alkyl pyrrolidones, e.g. n-octylpyrrolidone or cyclohexylpyrrolidone, epoxidized plant oil esters, e.g. methylated coconut or soybean oil ester and water. Mixtures of different solvents may be suitable. 
     Solid carriers used in the composition of this invention which may be used for dusts, wettable powders, water dispersible granules, or granules, may be mineral fillers, such as calcite, talc, kaolin, montmorillonite or attapulgite or others. The physical properties may be improved by addition of highly dispersed silica gel or polymers. Carriers for granules may be porous material, e.g., pumice, kaolin, sepiolite, bentonite; non-sorptive carriers may be calcite or sand or others. Additionally, a multitude of pre-granulated inorganic or organic materials may be used, such as dolomite or crushed plant residues. 
     Pesticidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surfactant facilitates this process of dilution. Thus, preferably at least one carrier in a composition according to the invention is a surfactant. For example, the composition may contain two or more carriers, at least one of which is a surfactant. 
     Surfactants may be nonionic, anionic, cationic or zwitterionic substances with good dispersing, emulsifying and wetting properties, depending on the nature of the active ingredients to be formulated. Surfactants may also include mixtures of individual surfactants. 
     Wettable powders in this invention suitably may contain about 5 to 90% w/w of active ingredient and, in addition to solid inert carrier, about 3 to 10% w/w of dispersing and wetting agents and, where necessary, 0 to 10% w/w of stabilizer(s) and/or other additives such as penetrants or stickers. Dusts may be formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and may be diluted in the field with further solid carrier to give a composition containing about 0.5 to 10% w/w of active ingredient. Water dispersible granules and granules may have a size approximately between 0.15 mm and 2.0 mm, and may be manufactured by a variety of techniques known in the art. These granules suitably will contain about 0.5 to 90% w/w active ingredient and 0 to 20% w/w of additives such as stabilizer, surfactants, slow release modifiers and binding agents. Emulsifiable concentrates suitably may contain, in addition to a solvent or a mixture of solvents, approximately 1 to 80% w/v active ingredient, 2 to 20% w/v emulsifiers and 0 to 20% w/v of other additives, such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates may be milled so as to obtain a stable, non-sedimenting flowable product and suitably contain about 5 to 75% w/v active ingredient, and 0.5 to 15% w/v of dispersing agents, 0.1 to 10% w/v of suspending agents such as protective colloids and thixotropic agents, 0 to 10% w/v of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation and crystalization or as antifreeze agents. 
     Aqueous dispersions and emulsions, for example compositions obtained by diluting the formulated product according to the invention with water, also lie within the scope of the invention. 
     The invention also encompasses the use of a carrier which will provide slow release of the pesticidal compounds into the environment of a plant which is to be protected, to extend the duration of the protective activity of the composition. 
     The biological activity of the active ingredients may be increased by including an adjuvant in the formulation or a spray dilution. An adjuvant is defined here as a substance which can increase the biological activity of an active ingredient but is not itself significantly biologically active. The adjuvant can either be included in the formulation as a coformulant or carrier, or can be added to the spray tank together with the formulation containing the active ingredient. 
     As a commodity, the compositions may preferably be in a concentrated form whereas the end user generally employs diluted compositions. The compositions may be diluted to a concentration down to about 0.001% of active ingredient. The doses preferably are in the approximate range from 0.01 to 10 kg a.i./ha. 
     Examples of formulations useful in the practice of the invention are: 
     
       
         
           
               
               
               
               
             
               
                   
               
             
            
               
                 SC-I 1 
                   
                   
                   
               
               
                 active ingredient 
                 Azolopyrimidine C 
                 100.0 
                 g 
               
               
                 Dispersing agent 
                 Morwet D425 1)   
                 25.0 
                 g 
               
               
                 Dispersing agent 
                 Pluronic ® PE 10500 2)   
                 5.0 
                 g 
               
               
                 Antifoaming agent 
                 Rhodorsil ® 426R 3)   
                 1.5 
                 g 
               
               
                 Dispersing agent 
                 Rhodopol ® 23 3)   
                 2.0 
                 g 
               
               
                 Antifreezing agent 
                 Propylene glycol 
                 80.0 
                 g 
               
               
                 Biocidal agent 
                 Proxel ® GXL 4)   
                 1.0 
                 g 
               
               
                 Water 
                   
                 to 1000 
                 ml 
               
               
                 SC-I 2 
               
               
                 active ingredient 
                 Azolopyrimidine C 
                 100.0 
                 g 
               
               
                 Dispersing agent 
                 Soprophor ® FL 3)   
                 30.0 
                 g 
               
               
                 Antifoaming agent 
                 Rhodorsil ® 426R 3)   
                 1.5 
                 g 
               
               
                 Dispersing agent 
                 Rhodopol ® 23 3)   
                 2.0 
                 g 
               
               
                 Antifreezing agent 
                 Propylene glycol 
                 80.0 
                 g 
               
               
                 Biocidal agent 
                 Proxe I ® GXL 4)   
                 1.0 
                 g 
               
               
                 Water 
                   
                 to 1000 
                 ml 
               
               
                 SC-A/B/C 
               
               
                 active ingredient 
                 selected from classes (A), (B), (C) 
                 200.0 
                 g 
               
               
                 Dispersing agent 
                 Soprophor ® FL 3)   
                 25.0 
                 g 
               
               
                 Antifoaming agent 
                 Rhodorsil ® 426R 3)   
                 1.5 
                 g 
               
               
                 Dispersing agent 
                 Rhodopol ® 23 3)   
                 2.0 
                 g 
               
               
                 Antifreezing agent 
                 Propylene glycol 
                 80.0 
                 g 
               
               
                 Biocidal agent 
                 Proxel ® GXL 4)   
                 1.0 
                 g 
               
               
                 Water 
                   
                 to 1000 
                 ml 
               
               
                 SC-I + A/B/C 
               
               
                 active ingredient 
                 Azolopyrimidine C 
                 60.0 
                 g 
               
               
                 active ingredient 
                 selected from classes (A), (B) and 
                 120.0 
                 g 
               
               
                   
                 (C) 
               
               
                 Dispersing agent 
                 Soprophor ® FL 3)   
                 25.0 
                 g 
               
               
                 Antifoaming agent 
                 Rhodorsil ® 426R 3)   
                 1.5 
                 g 
               
               
                 Dispersing agent 
                 Rhodopol ® 23 3)   
                 2.0 
                 g 
               
               
                 Antifreezing agent 
                 Propylene glycol 
                 80.0 
                 g 
               
               
                 Biocidal agent 
                 Proxel ® GXL  4)   
                 1.0 
                 g 
               
               
                 Water 
                   
                 to 1000 
                 ml 
               
               
                 DC-I 1 
               
               
                 active ingredient 
                 Azolopyrimidine A 
                 100.0 
                 g 
               
               
                 Wetting agent 
                 Pluronic ® PE6400 2)   
                 50.0 
                 g 
               
               
                 Dispersing agent 
                 Lutensol ® TO 12 2)   
                 50.0 
                 g 
               
               
                 Solvent 
                 benzyl alcohol 
                 to 1000 
                 ml 
               
               
                   
               
               
                   1) Product commercially available from Witco  
               
               
                   2) Product commercially available from BASF AG, Germany  
               
               
                   3) Product commercially available from Rhone-Poulenc  
               
               
                   4) Product commercially available from Zeneca  
               
            
           
         
       
     
     The formulation SC-A/B/C,comprising a compound selected from the classes (A), (B) and (C), may be mixed with any of the other formulations SC-I 1, SC-I 2, SC-I 3, or DC-I which comprise the Azolopyrimidine C to produce a composition of this invention. 
     In a preferred embodiment of the invention, each active ingredient is added to a tank mix in a separate formulation, to form a composition of this invention. 
     The present invention also relates to a kit for the preparation of a spray mixture consisting of two separate units: 
     (i) a unit which comprises at least one azolopyrimidine of formula I, in particular one or more compounds selected from the Azolopyrimidines A, B or C, conventional carriers and optionally adjuvants; 
     (ii) a unit which comprises at least one active ingredient selected from the classes (A), (B) and (C), preferably one or more compounds selected from the group consisting of carboxin, fluazinam, quinoxifen, metalaxyl, famoxadone, metconazole, epoxiconazole, propiconazole, azoxystrobin or kresoxim methyl conventional carriers and optionally adjuvants. 
     In a preferred embodiment, the kit includes two bottles with dispensing means which allow the easy and correct addition of the active ingredients to the tank mix. 
     A composition according to the invention preferably contains from about 0.5% to 95% by weight of active ingredients. 
     The compositions of this invention may be diluted down to a concentration of about 0.0001% of active ingredients. 
     The compositions of this invention can be applied to the plants or their environment simultaneously with or in succession with other active substances. These other active substances can be either fertilizers, agents which donate trace elements, or other preparations which influence plant growth. However, they can also be other fungicides, selective herbicides, insecticides, bactericides, nematicides, algicides, molluscidides, rodenticides, virucides, compounds inducing resistance into plants, biological control agents such as viruses, bacteria, nematodes, fungi and other microorganisms, repellents of birds and animals, and plant growth regulators, or mixtures of several of these preparations, if appropriate together with other carrier substances conventionally used in the art of formulation, surfactants or other additives which promote application. 
     Examples of insecticidal compounds useful in this invention are alpha-cypermethrin, benfuracarb, BPMC, buprofezine, carbosulfan, cartap, chlorfenvinphos, chlorpyrifos-methyl, cycloprothrin, cypermethrin, esfenvalerate, ethofenprox, fenpropathrin, flucythrinate, flufenoxuron, hydramethylnon, imidacloprid, isoxathion, MEP, MPP, nitenpyram, PAP, permethrin, propaphos, pymetrozine, silafluofen, tebufenozide, teflubenzuron, temephos, terbufos, tetrachlorvinphos and triazamate. 
     Examples of biological control agents useful in this invention are:  Bacillus thuringiensis, Verticillium lecanii, Autographica californica  NPV,  Beauvaria bassiana, Ampelomyces quisqualis, Bacilis subtilis, Pseudomonas fluorescens, Steptomyces griseoviridis  and  Trichoderma harzianum.    
     Examples of chemical agents that induce systemic acquired resistance in plants are: isonicotinic acid or derivatives thereof, 2,2-dichloro-3,3-dimethylcyclopropylcarboxylic acid and BION. 
     The present invention is of wide applicability in the protection of crops, trees, residential and ornamental plants against fungal attack. Preferred crops are cereals, such as wheat and barley, rice, vines, and apples. The duration of the protection is normally dependent on the individual compound selected, and also a variety of external factors, such as climate, the impact of which may be mitigated by the use of a suitable formulation. 
     The following examples further illustrate the present invention. It should be understood, however, that the invention is not limited solely to the particular examples given below. 
    
    
     EXAMPLES 
     General Methods 
     The trials are carried out under greenhouse (Examples 1 to 32) or field conditions (Examples 33 to 40) in residual or curative applications. The fungicides are applied in single treatments, or in a combination comprising an azolopyrimidine of formula I and a compound selected from the classes (A), (B) and (C) as defined above. The compounds are applied in form of an aqueous spray mix obtained from a concentrated formulation or the technical material. 
     I. Cereals and Dicots—Greenhouse 
     1. Seed is planted in 6 cm diameter plastic pots and maintained in the greenhouse. 
     2. When the primary leaf is fully expanded in the case of cereals or several leaves are present in the case of dicots, formulated test compounds are sprayed with a three nozzle overhead fungicide sprayer to near run-off. Alternatively, a single nozzle overhead track sprayer is used for application of the compounds to cereals at a rate of 200 l/ha. Plants are then allowed to air-dry. 
     3. Inoculation precedes treatment in the case of curative evaluations and follows treatment in case of residual evaluations. For inoculation of powdery mildew disease, plants are set up on greenhouse benches with bottom watering mats and inoculated by dusting them with conidia from infected plants. Between inoculation and treatment for curative evaluations and between treatment and inoculation for residual evaluations, plants are maintained in the greenhouse with bottom watering. 
     For inoculation of non-powdery mildew diseases, an aqueous spore suspension of the pathogen is applied to the plant and the plants are kept 1-2 days in a moist infection chamber before being returned to the greenhouse where they are maintained by bottom watering. 
     4. Disease on the foliage as percent leaf area with disease symptoms/signs is evaluated about 7 days after inoculation. In the case of wheat, the tips and bases of the leaves are excluded from the evaluation.          %                 disease                 control     =     100   -         %                 disease                 in                 treated                 plants       %                 disease                 in                 untreated                 plants       ×   100      %                       
     FORMULATION, REFERENCE COMPOUNDS AND CONTROLS 
     1. Technical compounds are formulated in a solvent/surfactant system consisting of 5% acetone and 0.05% Tween 20 in deionized water. Compounds are dissolved in acetone prior to addition of the water; the Tween 20 can be added through either the acetone or the water. Dilutions are made using the solvent/surfactant system. Formulated compounds are prepared using deionized water. 
     2. Two kinds of controls are included: 
     Plants treated with the solvent/surfactant solution and inoculated (Solvent Blank). 
     Untreated plants which are inoculated (Inoculated Control). 
     For the field study formulated Azolopyrimidine A, B or C and formulated compounds from the classes (A), (B) and (C) were used. 
     Evaluation of the Disease 
     Assessments of the diseases took place at the indicated day after the application of the compounds. Per cent infected leaf area infected was evaluated. The efficacy of the compounds/compounds mixtures to control the diseases was calculated by using the formula given above under item 4: 
     II. Apple Fruit Botrytis 
     1. Apples (Malus X domestica Borkh.) variety Golden Delicious are disinfected by washing them briefly in 70% ethanol. After drying the apples are marked with four short equal-distant lines indicating the positions to be wounded. 
     2. Corresponding with the marks, four holes are poked around the apple equator with a pipette tip. 10 μl of the treatment solution are pipetted into each hole. 
     3. Three hours after application, 10 μl of a conidial suspension of  Botrytis cinerea  are pipetted into each. For incubation, the treated/inoculated apples are set up for five days. 
     4. Disease occurs as rotten apple tissue surrounding the inoculated wounds. The diameter of the rotten zone around each wound is measured. 
     FORMULATION, REFERENCE COMPOUNDS AND CONTROLS 
     1. Technical compounds are formulated in a solvent system consisting of 5% acetone and 0.05% Tween 20 in deionized water. Compounds are dissolved in acetone prior to dilution with water. Formulated compounds are prepared using deionized water. 
     2. Three kinds of controls are included: 
     Apples treated with the solvent solution and inoculated (Solvent Blank). 
     Untreated apples which are inoculated (Inoculated Control). 
     Untreated apples which are not inoculated (Uninoculated Control). 
     Evaluation of the Disease 
     Assessments of the diseases took place at the indicated day after the application of the compounds. Per cent infected leaf area infected was evaluated. The efficacy of the compounds/compounds mixtures to control the diseases was calculated by using the formula:          %                 disease                 control     =     100   -         mean                 of                 diameters                 on                 treated                 apples       mean                 of                 diameters                 on                 untreated                 apples       ×   100      %                       
     Determination of Synergy 
     Synergy was calculated using the % disease control values of specific treatments for the two COLBY formula given hereinabove 
     III. Field Tests 
     The compounds are applied according to good agricultural practice in the form of an aqueous spray mix obtained from a concentrated formulation or the technical material at a rate of 400 l/ha. The disease control is evaluated according to the formula given for the greenhouse tests. 
     A Greenhouse Tests 
     Example 1 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+fenpropimorph (3 day residual) against  Leptosphaeria nodorum  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine A and an EC formulation containing 750 g fenpropimorph per liter. The observed and expected efficacies with different rates are given in Table I: 
     
       
         
           
               
               
               
               
             
               
                 TABLE I 
               
             
            
               
                   
               
               
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 Azolopyrimidine A 
                 fenpropimorph 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 100 
                 0 
                 40 
                 — 
               
               
                 10 
                 0 
                 35 
                 — 
               
               
                 0 
                 5 
                 15 
                 — 
               
               
                 0 
                 0.5 
                 19 
                 — 
               
               
                 100 
                 5 
                 71 
                 49 
               
               
                 100 
                 0.5 
                 80 
                 51 
               
               
                 10 
                 5 
                 55 
                 45 
               
               
                 10 
                 0.5 
                 50 
                 47 
               
               
                   
               
            
           
         
       
     
     Example 2 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+tebuconazole (3 day residual) against  Leptosphaeria nodorum  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine A and an EC formulation containing 250 g tebuconazole per liter. The observed and expected efficacies with different rates are given in Table II: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE II 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 tebuconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 100 
                 0 
                 40 
                 — 
               
               
                   
                 0 
                 0.2 
                 19 
                 — 
               
               
                   
                 0 
                 0.02 
                 25 
                 — 
               
               
                   
                 100 
                 0.2 
                 88 
                 51 
               
               
                   
                 100 
                 0.02 
                 87 
                 55 
               
               
                   
                   
               
            
           
         
       
     
     Example 3 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+tebuconazole (2 day residual) against  Blumeria graminis  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine A and an EC formulation containing 250 g tebuconazole per liter. The observed expected efficacies with different rates are given in Table III: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE III 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 tebuconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 10 
                 0 
                 14 
                 — 
               
               
                   
                 0 
                 0.2 
                 9 
                 — 
               
               
                   
                 0 
                 0.02 
                 2 
                 — 
               
               
                   
                 10 
                 0.2 
                 52 
                 22 
               
               
                   
                 10 
                 0.02 
                 33 
                 16 
               
               
                   
                   
               
            
           
         
       
     
     Example 4 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+vinclozolin (3 day residual) against  Botrytis cinerea  on apple fruits. 
     The tank mix was obtained from technical material of Azolopyrimidine A and a WG formulation containing 500 g vinclozolin per kg. The observed and expected efficacies with different rates are given in Table IV: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE IV 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 vinclozolin 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 10 
                 0 
                 33 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 10 
                 8 
                 — 
               
               
                   
                 10 
                 10 
                 54 
                 38 
               
               
                   
                 1 
                 10 
                 31 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 5 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+cyprodinil (3 day residual) against  Botrytis cinerea  on apple fruits. 
     The tank mix was obtained from technical material of Azolopyrimidine A and a WG formulation containing 750 g cyprodinil per kg. The observed and expected efficacies with different rates are given in Table V: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE V 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 cyprodinil 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 10 
                 0 
                 33 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 1 
                 46 
                 — 
               
               
                   
                 0 
                 0.1 
                 2 
                 — 
               
               
                   
                 10 
                 1 
                 66 
                 64 
               
               
                   
                 10 
                 0.1 
                 61 
                 34 
               
               
                   
                 1 
                 0.1 
                 3 
                  2 
               
               
                   
                   
               
            
           
         
       
     
     Example 6 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+benomyl (3 day residual) against  Botrytis cinerea  on apple fruits. 
     The tank mix was obtained from technical material of Azolopyrimidine A and a WP formulation containing 500 g benomyl per kg. The observed and expected efficacies with different rates are given in Table VI: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE VI 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 benomyl 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 10 
                 0 
                 25 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 10 
                 13 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 10 
                 10 
                 87 
                 35 
               
               
                   
                 10 
                 1 
                 38 
                 25 
               
               
                   
                 1 
                 10 
                 35 
                 13 
               
               
                   
                 1 
                 1 
                 15 
                  0 
               
               
                   
                   
               
            
           
         
       
     
     Example 7 
     Fungicidal efficacy of the mixture of Azolopyrimidine A+vinclozolin (3 day residual) against  Botrytis cinerea  on apple fruits. 
     The tank mix was obtained from technical material of Azolopyrimidine A and a WG formulation containing 500 g vinclozolin per kg. The observed and expected efficacies with different rates are given in Table VII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE VII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine A 
                 Vinclozolin 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 10 
                 0 
                 25 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 10 
                 17 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 10 
                 10 
                 57 
                 38 
               
               
                   
                 1 
                 1 
                 4 
                  0 
               
               
                   
                   
               
            
           
         
       
     
     Example 8 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metconazole (1 day residual) against  Rhynchosporium secalis  on barley. 
     The tank mix was obtained from technical materials of Azolopyrimidine C and metconazole. The observed and expected efficacies are given in Table VIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE VIII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 100 
                 0 
                 15 
                 — 
               
               
                   
                 0 
                 100 
                 87 
                 — 
               
               
                   
                 100 
                 100 
                 100 
                 89 
               
               
                   
                   
               
            
           
         
       
     
     Example 9 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metconazole (1 day residual) against  Septoria tritici  on wheat. 
     The tank mix was obtained from a SC formulation containing 100 g Azoplopyrimidine C per liter and an EC containing 100 g metconazole per liter. The observed and expected efficacies with different rates are given in Table IX: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE IX 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 40 
                 0 
                 91 
                 — 
               
               
                   
                 25 
                 0 
                 68 
                 — 
               
               
                   
                 8 
                 0 
                 0 
                 — 
               
               
                   
                 5 
                 0 
                 0 
                 — 
               
               
                   
                 2 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 25 
                 0 
                 — 
               
               
                   
                 0 
                 10 
                 0 
                 — 
               
               
                   
                 0 
                 8 
                 0 
                 — 
               
               
                   
                 0 
                 5 
                 0 
                 — 
               
               
                   
                 0 
                 2 
                 0 
                 — 
               
               
                   
                 40 
                 10 
                 92 
                 91  
               
               
                   
                 25 
                 25 
                 89 
                 68  
               
               
                   
                 8 
                 2 
                 11 
                 0 
               
               
                   
                 5 
                 5 
                 16 
                 0 
               
               
                   
                 2 
                 8 
                 28 
                 0 
               
               
                   
                   
               
            
           
         
       
     
     Example 10 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metconazole (1 day residual) against  Pyrenophora teres  on barley. 
     The tank mix was obtained from a SC formulation containing 100 g Azolopyrimidine C per liter and an EC containing 100 g metconazole per liter. The observed and expected efficacies with different rates are given in Table X: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE X 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 Metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 125 
                 0 
                 0 
                 — 
               
               
                   
                 50 
                 0 
                 0 
                 — 
               
               
                   
                 40 
                 0 
                 0 
                 — 
               
               
                   
                 25 
                 0 
                 0 
                 — 
               
               
                   
                 10 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 200 
                 73 
                 — 
               
               
                   
                 0 
                 125 
                 68 
                 — 
               
               
                   
                 0 
                 40 
                 34 
                 — 
               
               
                   
                 0 
                 25 
                 9 
                 — 
               
               
                   
                 0 
                 10 
                 4 
                 — 
               
               
                   
                 125 
                 125 
                 69 
                 68 
               
               
                   
                 50 
                 200 
                 82 
                 73 
               
               
                   
                 25 
                 25 
                 46 
                  9 
               
               
                   
                 40 
                 10 
                 9 
                  4 
               
               
                   
                 10 
                 40 
                 51 
                 34 
               
               
                   
                   
               
            
           
         
       
     
     Example 11 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metconazole (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from from a SC formulation containing 100 g Azolopyrimidine C per liter and an EC containing 100 g metconazole per liter. The observed and expected efficacies with different rates are given in Table XI: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XI 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 200 
                 0 
                 35 
                 — 
               
               
                   
                 125 
                 0 
                 20 
                 — 
               
               
                   
                 40 
                 0 
                 10 
                 — 
               
               
                   
                 25 
                 0 
                 5 
                 — 
               
               
                   
                 10 
                 0 
                 3 
                 — 
               
               
                   
                 8 
                 0 
                 1 
                 — 
               
               
                   
                 2 
                 0 
                 2 
                 — 
               
               
                   
                 0 
                 125 
                 97 
                 — 
               
               
                   
                 0 
                 50 
                 72 
                 — 
               
               
                   
                 0 
                 40 
                 31 
                 — 
               
               
                   
                 0 
                 25 
                 14 
                 — 
               
               
                   
                 0 
                 10 
                 8 
                 — 
               
               
                   
                 0 
                 8 
                 0 
                 — 
               
               
                   
                 0 
                 2 
                 0 
                 — 
               
               
                   
                 200 
                 50 
                 86 
                 82 
               
               
                   
                 125 
                 125 
                 99 
                 98 
               
               
                   
                 40 
                 10 
                 25 
                 17 
               
               
                   
                 25 
                 25 
                 22 
                 18 
               
               
                   
                 10 
                 40 
                 70 
                 33 
               
               
                   
                 8 
                 2 
                 1 
                  1 
               
               
                   
                 2 
                 8 
                 8 
                  2 
               
               
                   
                   
               
            
           
         
       
     
     Example 12 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+kresoxim methyl (1 day curative) against  Puccinia recondita  on wheat. 
     Plants sprayed twice, once with each compound. The tank mixes were obtained from a SC formulation containing 100 g Azolopyrimidine C per liter and a WG containing 500 g kresoxim methyl per kg. The observed and expected efficacies with different rates are given in Table XII: 
     
       
         
           
               
               
               
             
               
                 TABLE XII 
               
             
            
               
                   
               
               
                 dose rate (ppm) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 kresoxim methyl 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 400 
                 0 
                 99 
                 — 
               
               
                 200 
                 0 
                 97 
                 — 
               
               
                 100 
                 0 
                 79 
                 — 
               
               
                 50 
                 0 
                 66 
                 — 
               
               
                 25 
                 0 
                 25 
                 — 
               
               
                 0 
                 400 
                 5 
                 — 
               
               
                 0 
                 200 
                 1 
                 — 
               
               
                 0 
                 100 
                 0 
                 — 
               
               
                 0 
                 50 
                 1 
                 — 
               
               
                 0 
                 25 
                 0 
                 — 
               
               
                 400 
                 400 
                 99 
                 99 
               
               
                 200 
                 200 
                 94 
                 97 
               
               
                 100 
                 100 
                 86 
                 79 
               
               
                 50 
                 50 
                 84 
                 66 
               
               
                 25 
                 25 
                 29 
                 25 
               
               
                   
               
            
           
         
       
     
     Example 13 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+carboxin (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and WP formulation containing 750 g carboxin per kg. The observed and expected efficacies with different rates are given in Table XIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XIII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 carboxin 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 100 
                 — 
               
               
                   
                 1 
                 0 
                 71 
                 — 
               
               
                   
                 0.25 
                 0 
                 41 
                 — 
               
               
                   
                 0.06 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 4 
                 4 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 0 
                 0.25 
                 0 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 100 
                 100  
               
               
                   
                 1 
                 1 
                 89 
                 71 
               
               
                   
                 0.25 
                 0.25 
                 66 
                 49 
               
               
                   
                 0.06 
                 0.06 
                 59 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 14 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+fluazinam (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and a SC formulation containing 500 g fluazinam per liter. The observed and expected efficacies with different rates are given in Table XIV: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XIV 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 fluazinam 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 100 
                 — 
               
               
                   
                 1 
                 0 
                 71 
                 — 
               
               
                   
                 0.06 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 4 
                 17 
                 — 
               
               
                   
                 0 
                 1 
                 4 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 100 
                 100  
               
               
                   
                 1 
                 1 
                 92 
                 72 
               
               
                   
                 0.06 
                 0.06 
                 24 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 15 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+quinoxyfen (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and quinoxyfen. The observed and expected efficacies with different rates are given in Table XV: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XV 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 quinoxyfen 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 100 
                 — 
               
               
                   
                 1 
                 0 
                 71 
                 — 
               
               
                   
                 0.25 
                 0 
                 49 
                 — 
               
               
                   
                 0.06 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 4 
                 0 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 0 
                 0.25 
                 0 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 100 
                 100  
               
               
                   
                 1 
                 1 
                 95 
                 71 
               
               
                   
                 0.25 
                 0.25 
                 54 
                 49 
               
               
                   
                 0.06 
                 0.06 
                 23 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 16 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+quinoxyfen (1 day residual)) against  Blumeria graminis  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and quinoxyfen. The observed and expected efficacies with different rates are given in Table XVI: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XVI 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 quinoxyfen 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 96 
                 — 
               
               
                   
                 1 
                 0 
                 42 
                 — 
               
               
                   
                 0.25 
                 0 
                 19 
                 — 
               
               
                   
                 0.06 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 4 
                 99 
                 — 
               
               
                   
                 0 
                 1 
                 73 
                 — 
               
               
                   
                 0 
                 0.25 
                 18 
                 — 
               
               
                   
                 0 
                 0.06 
                 8 
                 — 
               
               
                   
                 4 
                 4 
                 100 
                 100  
               
               
                   
                 1 
                 1 
                 87 
                 85 
               
               
                   
                 0.25 
                 0.25 
                 53 
                 33 
               
               
                   
                 0.06 
                 0.06 
                 24 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 17 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metalaxyl (1 day residual) against  Blumeria graminis  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and metalaxyl. The observed and expected efficacies with different rates are given in Table XVII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XVII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 metalaxyl 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 96 
                 — 
               
               
                   
                 1 
                 0 
                 42 
                 — 
               
               
                   
                 0.25 
                 0 
                 19 
                 — 
               
               
                   
                 0.06 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 4 
                 0 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 0 
                 0.25 
                 0 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 92 
                 96 
               
               
                   
                 1 
                 1 
                 45 
                 42 
               
               
                   
                 0.25 
                 0.25 
                 34 
                 19 
               
               
                   
                 0.06 
                 0.06 
                 21 
                  0 
               
               
                   
                   
               
            
           
         
       
     
     Example 18 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+famoxadone (1 day residual) against  Blumeria graminis  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and famoxadone. The observed and expected efficacies with different rates are given in Table XVIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XVIII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 Famoxadone 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 96 
                 — 
               
               
                   
                 1 
                 0 
                 42 
                 — 
               
               
                   
                 0.25 
                 0 
                 19 
                 — 
               
               
                   
                 0.06 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 4 
                 0 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 0 
                 0.25 
                 0 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 96 
                 96 
               
               
                   
                 1 
                 1 
                 53 
                 42 
               
               
                   
                 0.25 
                 0.25 
                 34 
                 19 
               
               
                   
                 0.06 
                 0.06 
                 9 
                  0 
               
               
                   
                   
               
            
           
         
       
     
     Example 19 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+famoxadone (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and famoxadone. The observed and expected efficacies with different rates are given in Table XIX: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XIX 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 famoxadone 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 100 
                 — 
               
               
                   
                 1 
                 0 
                 71 
                 — 
               
               
                   
                 0.25 
                 0 
                 49 
                 — 
               
               
                   
                 0.06 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 4 
                 61 
                 — 
               
               
                   
                 0 
                 1 
                 31 
                 — 
               
               
                   
                 0 
                 0.25 
                 0 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 4 
                 4 
                 100 
                 100  
               
               
                   
                 1 
                 1 
                 87 
                 80 
               
               
                   
                 0.25 
                 0.25 
                 52 
                 49 
               
               
                   
                 0.06 
                 0.06 
                 29 
                  8 
               
               
                   
                   
               
            
           
         
       
     
     Example 20 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+dodine (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and a WP containing 650 g dodine per kg. The observed and expected efficacies with different rates are given in Table XX: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XX 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 dodine 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 0.86 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 0.06 
                 0.06 
                 28 
                 8 
               
               
                   
                   
               
            
           
         
       
     
     Example 21 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+copper oxychloride (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and a WP containing 450 g copper oxychloride per kg. The observed and expected efficacies with different rates are given in Table XXI: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE XXI 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
               
            
           
           
               
               
               
               
            
               
                   
                 copper 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 oxychloride 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 0.06 
                 0 
                 8 
                 — 
               
               
                   
                 0 
                 0.06 
                 0 
                 — 
               
               
                   
                 0.06 
                 0.06 
                 18 
                 8 
               
               
                   
                   
               
            
           
         
       
     
     Example 22 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+sulfur (1 day residual) against  Puccinia recondita  on wheat. 
     The tank mix was obtained from technical material of Azolopyrimidine C and sulfur. The observed and expected efficacies with different rates are given in Table XXII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 sulfur 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 1 
                 0 
                 71 
                 — 
               
               
                   
                 0 
                 1 
                 0 
                 — 
               
               
                   
                 1 
                 1 
                 86 
                 71 
               
               
                   
                   
               
            
           
         
       
     
     Example 23 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+triforine (1 day residual) against  Erysiphe cichoracearum  on cucumbers. 
     The tank mix was obtained from a SC formulation containing 100 g of Azolopyrimidine C per liter and an DC formulation containing and 190 g of triforine per liter. The observed and expected efficacies with different rates are given in Table XXIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXIII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 triforine 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 7 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 16 
                 15 
                 — 
               
               
                   
                 0 
                 4 
                 0 
                 — 
               
               
                   
                 4 
                 16 
                 47 
                 34 
               
               
                   
                 1 
                 4 
                 12 
                  0 
               
               
                   
                   
               
            
           
         
       
     
     Example 24 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+cyprodinil (1 day residual) against  Erysiphe cichoracearum  on cucumbers. 
     The tank mix was obtained from a SC formulation containing 100 g of Azolopyrimidine C per liter and a WG formulation containing and 750 g of cyprodinil per kg. The observed and expected efficacies with different rates are given in Table XXIV: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXIV 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (ppm) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 cyprodinil 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 4 
                 0 
                 7 
                 — 
               
               
                   
                 1 
                 0 
                 0 
                 — 
               
               
                   
                 0 
                 16 
                 29 
                 — 
               
               
                   
                 0 
                 4 
                 0 
                 — 
               
               
                   
                 4 
                 16 
                 41 
                 34 
               
               
                   
                 1 
                 4 
                 10 
                 0 
               
               
                   
                   
               
            
           
         
       
     
     Example 25 
     Fungicidal efficacy of the mixture of Azolopyrimidine C and different fungicides (1 day residual) against  Alternaria solani  on tomatoes. 
     The tank mix was obtained from an SC formulation containing 100 g Azolopyrimidine A per liter and WP formulations of dithianon (750 g/kg), captan (500 g/kg), cyprodinil (750 g/kg), mancozeb (800 g/kg), or a SC formulation of chlorothalonil (500 g/l), or a FS formulation of fenpiclonil (400 g/l), respectively. The observed and expected efficacies with different rates are given in Table XXV: 
     
       
         
           
               
               
               
               
               
             
               
                 TABLE XXV 
               
               
                   
               
               
                 Azolopyrimidine C 
                 Cereal 
                 rate 
                 Observed 
                 Expected 
               
               
                 (g/ha) 
                 Fungicide 
                 (g/ha) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                 4 
                 — 
                  0 
                 25 
                 — 
               
               
                 0 
                 dithianon 
                 16 
                 50 
                 — 
               
               
                 0 
                 captan 
                 16 
                 18 
                 — 
               
               
                 0 
                 cyprodinil 
                 16 
                 13 
                 — 
               
               
                 0 
                 mancozeb 
                 16 
                 27 
                 — 
               
               
                 0 
                 chlorothalonil 
                 16 
                 13 
                 — 
               
               
                 0 
                 fenpiclonil 
                 16 
                 76 
                 — 
               
               
                 4 
                 dithianon 
                 16 
                 76 
                 63 
               
               
                 4 
                 captan 
                 16 
                 60 
                 38 
               
               
                 4 
                 cyprodinil 
                 16 
                 50 
                 35 
               
               
                 4 
                 mancozeb 
                 16 
                 62 
                 45 
               
               
                 4 
                 chlorothalonil 
                 16 
                 57 
                 35 
               
               
                 4 
                 fenpiclonil 
                 16 
                 91 
                 82 
               
               
                   
               
            
           
         
       
     
     Example 26 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Fenhexamid (2 days curative) against  Blumeria graminis  on barley. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Fenhexamid. The active ingredients, the observed and expected efficacies with different rates are given in Table XXVI: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXVI 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 180 
                 86 
                   
               
               
                   
                 60 
                 60 
               
               
                   
                 20 
                 37 
               
               
                   
                 6.7 
                 29 
               
               
                   
                 2.2 
                 8 
               
               
                   
                 0.74 
                 0 
               
               
                 Fenhexamid 
                 180 
                 39 
               
               
                   
                 60 
                 7 
               
               
                   
                 20 
                 1 
               
               
                   
                 6.7 
                 0 
               
               
                   
                 2.2 
                 0 
               
               
                   
                 0.74 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 180 + 180 
                 95 
                 91 
               
               
                 Fenhexamid 
                 60 + 60 
                 70 
                 63 
               
               
                   
                 20 + 20 
                 42 
                 38 
               
               
                   
                 6.7 + 6.7 
                 36 
                 29 
               
               
                   
                 2.2 + 2.2 
                 18 
                 8 
               
               
                   
                 0.74 + 0.74 
                 8 
                 0 
               
               
                   
               
            
           
         
       
     
     Example 27 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin or Trifloxystrobin (2 days curative) against  Blumeria graminis  on wheat. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin or Trifloxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXVII: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXVII 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 50 
                 81 
                   
               
               
                   
                 25 
                 61 
               
               
                   
                 12.5 
                 40 
               
               
                   
                 6.3 
                 10 
               
               
                   
                 3.1 
                 0 
               
               
                   
                 1.6 
                 0 
               
               
                 Azoxystrobin 
                 50 
                 61 
               
               
                   
                 25 
                 48 
               
               
                   
                 12.5 
                 28 
               
               
                   
                 6.3 
                 21 
               
               
                   
                 3.1 
                 2 
               
               
                   
                 1.6 
                 0 
               
               
                 Trifloxystrobin 
                 50 
                 99 
               
               
                   
                 25 
                 98 
               
               
                   
                 12.5 
                 89 
               
               
                   
                 6.3 
                 78 
               
               
                   
                 3.1 
                 55 
               
               
                   
                 1.6 
                 34 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 95 
                 93 
               
               
                 Azoxystrobin 
                 25 + 25 
                 79 
                 80 
               
               
                   
                 12.5 + 12.5 
                 62 
                 57 
               
               
                   
                 6.3 + 6.3 
                 30 
                 29 
               
               
                   
                 3.1 + 3.1 
                 20 
                 2 
               
               
                   
                 1.6 + 1.6 
                 14 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 100 
                 100 
               
               
                 Trifloxystrobin 
                 25 + 25 
                 100 
                 99 
               
               
                   
                 12.5 + 12.5 
                 93 
                 93 
               
               
                   
                 6.3 + 6.3 
                 75 
                 80 
               
               
                   
                 3.1 + 3.1 
                 67 
                 55 
               
               
                   
                 1.6 + 1.6 
                 45 
                 34 
               
               
                   
               
            
           
         
       
     
     Example 28 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin or Trifloxystrobin (2 days curative) against  Puccinia recondita  on wheat. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin or Trifloxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXVIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXVIII 
               
               
                   
                   
               
               
                   
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                   
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 S)-Azolopyrimidine C 
                 25 
                 54 
                   
               
               
                   
                 12.5 
                 23 
               
               
                   
                 6.3 
                 8 
               
               
                   
                 3.1 
                 0 
               
               
                   
                 1.6 
                 0 
               
               
                 Azoxystrobin 
                 25 
                 95 
               
               
                   
                 12.5 
                 85 
               
               
                   
                 6.3 
                 48 
               
               
                   
                 3.1 
                 25 
               
               
                   
                 1.6 
                 0 
               
               
                 Trifloxystrobin 
                 25 
                 0 
               
               
                   
                 12.5 
                 0 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                   
                 1.6 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 25 + 25 
                 99 
                 98 
               
               
                 Azoxystrobin 
                 12.5 + 12.5 
                 87 
                 88 
               
               
                   
                 6.3 + 6.3 
                 81 
                 52 
               
               
                   
                 3.1 + 3.1 
                 45 
                 25 
               
               
                   
                 1.6 + 1.6 
                 18 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 25 + 25 
                 53 
                 54 
               
               
                 Trifloxystrobin 
                 12.5 + 12.5 
                 36 
                 23 
               
               
                   
                 6.3 + 6.3 
                 15 
                 8 
               
               
                   
                 3.1 + 3.1 
                 5 
                 0 
               
               
                   
                 1.6 + 1.6 
                 0 
                 0 
               
               
                   
               
            
           
         
       
     
     Example 29 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin or Trifloxystrobin (2 days curative) against  Blumeria graminis  on barley. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin or Trifloxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXIX: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXIX 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 50 
                 73 
                   
               
               
                   
                 25 
                 54 
               
               
                   
                 12.5 
                 31 
               
               
                   
                 6.3 
                 15 
               
               
                   
                 3.1 
                 1 
               
               
                   
                 1.6 
                 0 
               
               
                 Azoxystrobin 
                 50 
                 87 
               
               
                   
                 25 
                 73 
               
               
                   
                 12.5 
                 49 
               
               
                   
                 6.3 
                 21 
               
               
                   
                 3.1 
                 10 
               
               
                   
                 1.6 
                 0 
               
               
                 Trifloxystrobin 
                 50 
                 96 
               
               
                   
                 25 
                 89 
               
               
                   
                 12.5 
                 74 
               
               
                   
                 6.3 
                 59 
               
               
                   
                 3.1 
                 36 
               
               
                   
                 1.6 
                 22 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 98 
                 96 
               
               
                 Azoxystrobin 
                 25 + 25 
                 90 
                 88 
               
               
                   
                 12.5 + 12.5 
                 75 
                 65 
               
               
                   
                 6.3 + 6.3 
                 51 
                 33 
               
               
                   
                 3.1 + 3.1 
                 18 
                 11 
               
               
                   
                 1.6 + 1.6 
                 1 
                 1 
               
               
                 (S)-Azotopyrimidine C + 
                 50 + 50 
                 100 
                 99 
               
               
                 Trifloxystrobin 
                 25 + 25 
                 98 
                 95 
               
               
                   
                 12.5 + 12.5 
                 87 
                 82 
               
               
                   
                 6.3 + 6.3 
                 61 
                 65 
               
               
                   
                 3.1 + 3.1 
                 46 
                 37 
               
               
                   
                 1.6 + 1.6 
                 28 
                 22 
               
               
                   
               
            
           
         
       
     
     Example 30 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin or Trifloxystrobin (4 days residual) against  Blumeria graminis  on wheat. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin or Trifloxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXX: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXX 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 50 
                 34 
                   
               
               
                   
                 25 
                 11 
               
               
                   
                 12.5 
                 3 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                 Azoxystrobin 
                 50 
                 9 
               
               
                   
                 25 
                 9 
               
               
                   
                 12.5 
                 7 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                 Trifloxystrobin 
                 50 
                 14 
               
               
                   
                 25 
                 0 
               
               
                   
                 12.5 
                 0 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 49 
                 40 
               
               
                 Azoxystrobin 
                 25 + 25 
                 25 
                 19 
               
               
                   
                 12.5 + 12.5 
                 18 
                 10 
               
               
                   
                 6.3 + 6.3 
                 1 
                 0 
               
               
                   
                 3.1 + 3.1 
                 0 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 51 
                 43 
               
               
                 Trifloxystrobin 
                 25 + 25 
                 27 
                 11 
               
               
                   
                 12.5 + 12.5 
                 29 
                 3 
               
               
                   
                 6.3 + 6.3 
                 7 
                 0 
               
               
                   
                 3.1 + 3.1 
                 9 
                 0 
               
               
                   
               
            
           
         
       
     
     Example 31 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin or Trifloxystrobin (4 days residual) against  Puccinia recondita  on wheat. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin or Trifloxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXXI: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXXI 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 50 
                 50 
                   
               
               
                   
                 25 
                 27 
               
               
                   
                 12.5 
                 16 
               
               
                   
                 6.3 
                 9 
               
               
                   
                 3.1 
                 0 
               
               
                 Azoxystrobin 
                 50 
                 8 
               
               
                   
                 25 
                 0 
               
               
                   
                 12.5 
                 0 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                 Trifloxystrobin 
                 50 
                 0 
               
               
                   
                 25 
                 0 
               
               
                   
                 12.5 
                 0 
               
               
                   
                 6.3 
                 0 
               
               
                   
                 3.1 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 63 
                 54 
               
               
                 Azoxystrobin 
                 25 + 25 
                 28 
                 27 
               
               
                   
                 12.5 + 12.5 
                 21 
                 16 
               
               
                   
                 6.3 + 6.3 
                 10 
                 9 
               
               
                   
                 3.1 + 3.1 
                 6 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 59 
                 50 
               
               
                 Trifloxystrobin 
                 25 + 25 
                 35 
                 27 
               
               
                   
                 12.5 + 12.5 
                 15 
                 16 
               
               
                   
                 6.3 + 6.3 
                 10 
                 9 
               
               
                   
                 3.1 + 3.1 
                 1 
                 0 
               
               
                   
               
            
           
         
       
     
     Example 32 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C in admixture with Azoxystrobin (4 days residual) against  Blumeria graminis  on barley. 
     The tank mixes were obtained from technical material of (S)-Azolopyrimidine C and Azoxystrobin. The active ingredients, the observed and expected efficacies with different rates are given in Table XXXII: 
     
       
         
           
               
               
               
               
             
               
                 TABLE XXXII 
               
               
                   
               
               
                   
                 dose rate 
                 Observed 
                 Expected 
               
               
                 Compound 
                 (ppm) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 50 
                 28 
                   
               
               
                   
                 25 
                 22 
               
               
                   
                 12.5 
                 17 
               
               
                   
                 6.3 
                 8 
               
               
                   
                 3.1 
                 3 
               
               
                   
                 1.6 
                 0 
               
               
                 Azoxystrobin 
                 50 
                 9 
               
               
                   
                 25 
                 2 
               
               
                   
                 12.5 
                 3 
               
               
                   
                 6.3 
                 3 
               
               
                   
                 3.1 
                 3 
               
               
                   
                 1.6 
                 0 
               
               
                 (S)-Azolopyrimidine C + 
                 50 + 50 
                 39 
                 34 
               
               
                 Azoxystrobin 
                 25 + 25 
                 34 
                 24 
               
               
                   
                 12.5 + 12.5 
                 27 
                 19 
               
               
                   
                 6.3 + 6.3 
                 20 
                 11 
               
               
                   
                 3.1 + 3.1 
                 20 
                 6 
               
               
                   
                 1.6 + 1.6 
                 14 
                 0 
               
               
                   
               
            
           
         
       
     
     B Field Tests 
     Example 33 
     Fungicidal efficacy of the mixture of Azolopyrimidine B+pyrimethanil in the field against  Botrytis cinerea  in vines 
     The tank mix was obtained from a SC formulation containing 100 g of Azolopyrimidine B per liter and a SC formulation containing 400 g of pyrimethanil per liter. The observed and expected efficacies are given in Table XXXIII: 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXXIII 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (g/ha) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine B 
                 pyrimethanil 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 250 
                 0 
                 58 
                 — 
               
               
                   
                 0 
                 500 
                 66 
                 — 
               
               
                   
                 250 
                 500 
                 92 
                 86 
               
               
                   
                   
               
            
           
         
       
     
     Example 34 
     Fungicidal efficacy of the mixture of Azolopyrimidine C+metconazole in the field against  Septoria tritici  on wheat. 
     The tank mix was obtained from an EC formulation containing 150 g Azolopyrimidine C per liter and a SL formulation containing 60 g metconazole per liter. The observed and expected efficacies with different rates are given in Table XXXIVa (19 days after application) and Table XXXIVb (25 days after application): 
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXXIVa 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (g/ha) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 Metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 25 
                 0 
                 48 
                 — 
               
               
                   
                 0 
                 15 
                 9 
                 — 
               
               
                   
                 0 
                 30 
                 36 
                 — 
               
               
                   
                 0 
                 45 
                 24 
                 — 
               
               
                   
                 25 
                 15 
                 73 
                 53 
               
               
                   
                 25 
                 30 
                 74 
                 67 
               
               
                   
                 25 
                 45 
                 76 
                 60 
               
               
                   
                   
               
            
           
         
       
     
     
       
         
           
               
               
               
               
               
             
               
                   
                 TABLE XXXIVb 
               
             
            
               
                   
                   
               
               
                   
                 dose rate (g/ha) 
                   
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
               
            
               
                   
                 Azolopyrimidine C 
                 Metconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
                   
               
            
           
           
               
               
               
               
               
            
               
                   
                 50 
                 0 
                 61 
                 — 
               
               
                   
                 75 
                 0 
                 13 
                 — 
               
               
                   
                 0 
                 15 
                 33 
                 — 
               
               
                   
                 0 
                 60 
                 48 
                 — 
               
               
                   
                 50 
                 15 
                 82 
                 74 
               
               
                   
                 75 
                 60 
                 66 
                 55 
               
               
                   
                   
               
            
           
         
       
     
     Example 35 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C+kresoxim methyl in the field against  Septoria tritici  on wheat. 
     The tank mix was obtained from a SC formulation containing 100 g (S)-Azolopyrimidine C per liter and a WG formulation containing 500 g kresoxim methyl per kg. The observed and expected efficacies with different rates are given in Tables XXXVa (7 days after application), XXXVb (22 days after application), XXXVc (34 days after application), and XXXVd (41 days after application): 
     
       
         
           
               
               
               
             
               
                 TABLE XXXVa 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 kresoxim methyl 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 25 
                 0 
                 34 
                 — 
               
               
                 0 
                 100 
                 40 
                 — 
               
               
                 25 
                 100 
                 70 
                 60 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
               
               
             
               
                 TABLE XXXVb 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 kresoxim methyl 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 25 
                 0 
                 74 
                 — 
               
               
                 100 
                 0 
                 87 
                 — 
               
               
                 0 
                 100 
                 64 
                 — 
               
               
                 25 
                 100 
                 92 
                 87 
               
               
                 100 
                 100 
                 99 
                 96 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
               
               
             
               
                 TABLE XXXVc 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 kresoxim methyl 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 50 
                 0 
                 53 
                 — 
               
               
                 100 
                 0 
                 70 
                 — 
               
               
                 0 
                 50 
                 44 
                 — 
               
               
                 0 
                 100 
                 59 
                 — 
               
               
                 50 
                 100 
                 88 
                 83 
               
               
                 100 
                 50 
                 84 
                 83 
               
               
                 100 
                 100 
                 92 
                 88 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
               
               
             
               
                 TABLE XXXVd 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 kresoxim methyl 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 75 
                 0 
                 92 
                 — 
               
               
                 0 
                 100 
                 92 
                 — 
               
               
                 75 
                 100 
                 100 
                 98 
               
               
                   
               
            
           
         
       
     
     Example 36 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C+cyproconazole in the field against  Blumeria graminis  on wheat 17 days after application. 
     The tank mix was obtained from a SC formulation containing 100 g (S)-Azolopyrimidine C per liter and an EC formulation containing 60 g cyproconazole per liter. The observed and expected efficacies with different rates are given in Table XXXVI: 
     
       
         
           
               
               
               
             
               
                 TABLE XXXVI 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 cyproconazole 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 25 
                 0 
                 63 
                 — 
               
               
                 50 
                 0 
                 78 
                 — 
               
               
                 75 
                 0 
                 74 
                 — 
               
               
                 0 
                 15 
                 86 
                 — 
               
               
                 0 
                 30 
                 82 
                 — 
               
               
                 25 
                 15 
                 96 
                 95 
               
               
                 25 
                 30 
                 98 
                 93 
               
               
                 50 
                 30 
                 100 
                 96 
               
               
                 75 
                 30 
                 98 
                 95 
               
               
                   
               
            
           
         
       
     
     Example 37 
     Fungicidal efficacy of the mixture of (S)-Azolopyrimidine C+azoxystrobin in the field against  Blumeria graminis  on wheat 17 days after application. 
     The tank mix was obtained from a SC formulation containing 100 g (S)-Azolopyrimidine C per liter and a SC formulation containing 250 g azoxystrobin per kg. The observed and expected efficacies with different rates are given in Table XXXVII: 
     
       
         
           
               
               
               
             
               
                 TABLE XXXVII 
               
             
            
               
                   
               
               
                 dose rate (g/ha) 
                 Observed 
                 Expected 
               
            
           
           
               
               
               
               
            
               
                 (S)-Azolopyrimidine C 
                 Azoxystrobin 
                 Efficacy 
                 Efficacy 
               
               
                   
               
            
           
           
               
               
               
               
            
               
                 25 
                 0 
                 63 
                 — 
               
               
                 50 
                 0 
                 78 
                 — 
               
               
                 75 
                 0 
                 74 
                 — 
               
               
                 100 
                 0 
                 96 
                 — 
               
               
                 0 
                 75 
                 49 
                 — 
               
               
                 25 
                 75 
                 92 
                 81 
               
               
                 50 
                 75 
                 94 
                 89 
               
               
                 75 
                 75 
                 92 
                 86 
               
               
                 100 
                 75 
                 100 
                 98 
               
               
                   
               
            
           
         
       
     
     Example 38 
     Fungicidal efficacy of the mixture of Azolopyrimidine A and different cereal fungicides in the field against  Blumeria graminis  on wheat 15 days after application. 
     The tank mix was obtained from an SC formulation containing 100 g Azolopyrimidine A per liter and commercially available formulations of metconazole, epoxiconazole or kresoxim methyl, respectively. The observed and expected efficacies with different rates are given in Table XXXVIII: 
     
       
         
           
               
               
               
               
               
             
               
                 TABLE XXXVIII 
               
               
                   
               
               
                   
                 Cereal 
                 rate 
                 Observed 
                 Expected 
               
               
                 Azolopyrimidine A 
                 Fungicide 
                 (g/ha) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
            
               
                 125 
                 — 
                 0 
                 22 
                 — 
               
               
                 0 
                 metconazole 
                 45 
                 54 
                 — 
               
               
                 0 
                 epoxiconazole 
                 63 
                 40 
                 — 
               
               
                 0 
                 kresoxim methyl 
                 100 
                 85 
                 — 
               
               
                 125 
                 metconazole 
                 45 
                 79 
                 64 
               
               
                 125 
                 epoxiconazole 
                 63 
                 74 
                 53 
               
               
                 125 
                 kresoxim methyl 
                 100 
                 92 
                 88 
               
               
                   
               
            
           
         
       
     
     Example 39 
     Fungicidal efficacy of the mixture of Azolopyrimidine A and different cereal fungicides the field against  Septoria tritici  on wheat 15 days after application. 
     The tank mix was obtained from an SC formulation containing 100 g Azolopyrimidine A per liter and commercially available formulations of metconazole, epoxiconazole or propiconazole, respectively. The observed and expected efficacies with different rates are given in Table XXXIX: 
     
       
         
           
               
               
               
               
               
             
               
                 TABLE XXXIX 
               
               
                   
               
               
                   
                 Cereal 
                 rate 
                 Observed 
                 Expected 
               
               
                 Azolopyrimidine A 
                 Fungicide 
                 (g/ha) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
            
               
                 125 
                 — 
                  0 
                 63 
                 — 
               
               
                 0 
                 metconazole 
                 45 
                 77 
                 — 
               
               
                 0 
                 epoxiconazole 
                 63 
                 93 
                 — 
               
               
                 0 
                 propiconazole 
                 63 
                 72 
                 — 
               
               
                 125 
                 metconazole 
                 45 
                 99 
                 91 
               
               
                 125 
                 epoxiconazole 
                 63 
                 97 
                 97 
               
               
                 125 
                 propiconazole 
                 63 
                 93 
                 90 
               
               
                   
               
            
           
         
       
     
     Example 40 
     Fungicidal efficacy of the mixture of Azolopyrimidine A and different cereal fungicides in the field against  Puccinia recondita  on wheat 50 days after application. 
     The tank mix was obtained from an SC formulation containing 100 g Azolopyrimidine A per liter and commercially available formulations of metconazole, epoxiconazole, propiconazole or kresoxim methyl, respectively. The observed and expected efficacies with different rates are given in Table XXXX: 
     
       
         
           
               
               
               
               
               
             
               
                 TABLE XXXX 
               
               
                   
               
               
                   
                 Cereal 
                 rate 
                 Observed 
                 Expected 
               
               
                 Azolopyrimidine A 
                 Fungicide 
                 (g/ha) 
                 Efficacy 
                 Efficacy 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
            
               
                 125 
                 — 
                 0 
                 0 
                 — 
               
               
                 0 
                 metconazole 
                 45 
                 75 
                 — 
               
               
                 0 
                 epoxiconazole 
                 63 
                 95 
                 — 
               
               
                 0 
                 propiconazole 
                 63 
                 49 
                 — 
               
               
                 0 
                 kresoxim methyl 
                 100 
                 0 
                 — 
               
               
                 125 
                 metconazole 
                 45 
                 85 
                 75 
               
               
                 125 
                 epoxiconazole 
                 63 
                 97 
                 95 
               
               
                 125 
                 propiconazole 
                 63 
                 67 
                 49 
               
               
                 125 
                 kresoxim methyl 
                 100 
                 64 
                 0