MXPA00005362A - FUNGICIDAL COMBINATIONS COMPRISING THIENO[2,3-d]PYRIMIDIN-4-ONE - Google Patents

Abstract

The invention relates to novel fungicidal compositions having a synergistically increased action, wherein component a) is a thieno[2,3-d]pyrimidin-4-one of formula (I) wherein R1 is halogen, R2 is C1-C5alkyl, -CH2-cyclopropyl and R3 is C1-C5alkyl, -CH2-cyclopropyl;in association with b) either an anilinopyrimidine fungicide (II), or an azole fungicide (III), or a morpholine fungicide (IV), or a strobilurin compound (V), or a pyrrole compound (VI), a phenylamide (VII), or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram and zineb, or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate and oxine-copper, or a phthalimide coumpound (VIII), or prochloraz, or triflumizole, or pyrifenox, or acibenzolar-S-methyl, or chlorothalonil, or cymoxanil, or dimethomorph, or famoxadone, or fenhexamide, or fenarimol, or fluazinam, or fosetyl-aluminium, or quinoxyfen, or fenpropidine, or spiroxamine, or carbendazime, or thiabendazole, or ethirimol, or triazoxide, or guazatine.

Description

CnMRTW? CTQNF.S FITNGTCTnAS QÜF, UNDERSTAND ttv. * Wn [2, ^ -rf] Pt? Tntnt -? -.? - r > wa The present invention relates to novel fungicidal compositions for the treatment of phytopathogenic diseases of crop plants, and against infestation in the propagation supply of plants or other plant material, especially phytopathogenic fungi, and to a method for combating diseases phytopathogens in crop plants or for seed coatings. It is known that certain pyrimidin-4-one derivatives have biological activity against phytopathogenic fungi, for example, as they are known in International Publication Number WO 97/33890, where their properties and methods of preparation are described. On the other hand, anilinopyrimidines, azole fungicides, phthalimides, phenylamides, strobilurins, pyrroles, dithiocarbamates, and morpholines are widely known as plant fungicides to be applied in different crops of cultivated plants. However, the tolerance of the crop and the activity against the phytopathogenic fungi of the plant, do not always satisfy the needs of the agricultural practice in many cases and aspects.

The hour has been discovered that the use of: a) a thieno [2,3-d] pyrimidin-4-one of the formula I where: R? is halogen, R2 is alkyl of 1 to 5 carbon atoms, -CH2-cyclopropyl, and R3 is alkyl of 1 to 5 carbon atoms, -CH2-cyclopropyl; in association with: b) either an anilinopyrimidine of formula II: wherein: R4 is methyl, 1-propynyl, or cyclopropyl; or an azole of the formula III: from: A is selected from: -O-CH- (xv) CH- OH CR7R8R9 wherein the carbon atom is attached to the benzene ring of formula III, and wherein: R5 is H, F, Cl, phenyl, 4-fluorophenoxy, or 4-chlorophenoxy; R5 is H, Cl, or F; R7 and R8 are independently H or CH3; R9 is alkyl of 1 to 4 carbon atoms or cyclopropyl; R10 is 4-chlorophenyl or 4-fluorophenyl; Rii is phenyl, and R12 is allyloxy, alkyl of 1 to 4 carbon atoms, or 1,1,2,2-tetrafluoroethoxymethyl, and the salts of this azole fungicide; or a morpholine fungicide of formula IV: wherein: RX3 is cycloalkyl of 8 to 15 carbon atoms, alkyl of 8 to 15 carbon atoms, or alkyl of 1 to 4 carbon atoms-phenylalkyl of 1 to 4 carbon atoms, and the salts of this morpholine fungicide; or a strobilurin compound of the formula V: wherein: X is NH or O, Y is CH or N, and Ri4 is 2-methylphenoxymethyl, 2,5-dimethylphenoxymethyl, 4- (2-cyanophenoxy) pyrimidin-6-yloxy, or 4- (3-trifluoromethylphenyl) - 3-aza-2-oxa-3-pentyl; or a pyrrole compound of the formula VI wherein: R15 and Ri6 are independently halogen, or together form a perhalomethylenedioxo bridge; or a phenylamide of formula VII: wherein: R17 is benzyl, methoxymethyl, 2-furanyl, chloromethyl, Z is CH or N, R2? is hydrogen or methyl, R22 is hydrogen or methyl; or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram, and zineb; or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate, and oxine-copper; or azu re; or a phthalimide compound of the formula VIII: wherein: R19 and R2o together form a bridge of four members -CH2-CH = CH-CH2- or = CH-CH = CH-CH =; or with a compound of formula IX: or with a compound of formula X: or with a compound of formula XI: or with a compound of formula XII: or with a compound of the formula XIII or with a compound of the formula XIV: O CN (XIV) H3C-CH2 NH-C NH C C = N-OCH3 or with a compound of the formula XV: or with a compound of formula XVI: with a compound of formula XVII fifteen or with a compound of formula XVIII: (XVIII) or with a compound of formula XIX: or with a compound of the formula XX: or with a compound of formula XXI: or with a compound of formula XXII: or with a compound of the formula XXIII: (XXIII) or with a compound of the formula XXIV: or with a compound of formula XXV: or with a compound of formula XXVI: or with a compound of the formula XXVII: (XXVII) or with a compound of the formula XXVIII R R R-NH- (CH 2) 8-N- | (CH 2) 8-NJ-H (XXVIII! wherein: n is 0 or 1 or 2, et cetera, and R is hydrogen or -C (= NH) NH 2; It is particularly effective in combating or preventing fungal diseases of crop plants. These combinations exhibit a synergistic fungicidal activity. The combinations according to the invention can also comprise more than one of the active components b), if it is desired to widen the spectrum of disease control. For example, it may be convenient, in agricultural practice, to combine two or three components b) with any of the compounds of the formula I, or with any preferred member of the group of compounds of the formula I.

From the International Publication Number WO 97/33890, the following specific species of the formula I are known.

Compound No. Ri R2 R3 I.01 Cl normal propyl normal propyl 1.02 Br normal propyl normal propyl 1.03 Cl propyl normal normal butyl 1.04 Br propyl normal butyl normal 1.05 Cl butyl normal normal propyl 1.06 Br butyl normal propyl normal 1.07 Cl isobutyl propium normal 1.08 Br isobutyl propyl normal 1.09 Cl propyl normal isobutyl 1.10 Br normal propyl isobutyl A preferred embodiment of the present invention is represented by those combinations comprising, as component a), a compound of formula I wherein Ri is chlorine or bromine, and R2 is normal propyl, normal butyl, isobutyl, and R3 is normal propyl, normal butyl, isobutyl. Among the mixtures of the present invention, preference is given to the mixture of compounds 1.01, 1.02, 1.03, 1.04, 1.05, 1.06, 1.07, or 1.08, with the compounds of component b), especially the commercially available products that fall within the given ranges, that is, the commercial products mentioned throughout this document.

The salts of the active ingredients of azole, amine, and morpholine, are prepared by their reaction with acids, for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid, or sulfuric acid, phosphoric acid, or nitric acid, or organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzenesulfonic acid, p-acid toluenesulfonic, methanesulfonic acid, salicylic acid, p-aminosalicylic acid, and 1,2-naphthalenedisulfonic acid. The combinations of active ingredients are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (for example, Venturia, Podosphaera, Erysiphe, Monilinia, Sclerotinia, Mycosphaerella, Uncinula); Basidiomycetes (for example, the genus Hemileia, Rhizoctonia, Tilletia, Puccinia); Imperfect fungus (for example, Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternarla, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (for example, Phytophthora, Peronospora, Premia, Py hium, Plasmopara). The target crops for the indication areas disclosed herein, comprise, within the scope of this invention, for example, the following plant species: cereals (wheat, barley, rye, oats, rice, sorghum, and related crops). ), beet (sugar beet and fodder beet); grapefruit, hard fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rapeseed, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa seeds, peanuts); cucumber plants (courgettes, cucumbers, melons); fiber plants (cotton, linen, hemp, jute); citrus fruit (oranges, lemons, grapefruit, tangerines); vegetables (spinach, lettuce, asparagus, pumpkins, cts, onions, tomatoes, potatoes, paprika); lauraceae (avocados, cinnamon, camphor); or plants such as corn, tobacco, nuts, coffee, sugar cane, tea, vines, hops, peat, bananas and natural rubber plants, as well as ornamentals (flowers, shrubs, broadleaf trees and evergreen trees, such as conifers) and its seeds. The list does not represent any limitation. The combinations of the present invention can also be used in the area of protection of technical material against fungal attack. Technical areas include wood, paper, leather, constructions, cooling and heating systems, ventilation and air conditioning systems, and the like. The combinations according to the present invention can prevent the inconvenient effects, such as decay, discoloration, or mold.

The combinations according to the present invention are particularly effective against oxidations and dusty molds, pyrenophora, rhynchosporium, and Liposhoperia fungi, in particular against pathogens of monocotyledonous plants, such as cereals, including wheat and barley. They are also particularly effective against velvety mold species, especially plasma on vines. The amount of combination of the invention to be applied will depend on different factors, such as the compound employed, the subject of the treatment (plant, soil, seeds), the type of treatment (for example, spraying, dusting, coating of seeds), the purpose of the treatment (prophylactic or therapeutic), the type of fungus to be treated, and the time of application. Particularly preferred mixing components of the compounds of formula II are those wherein R 4 is methyl or cyclopropyl. These compounds are commonly known as pyrimethanil and cyprodinil. Particularly preferred mixing components of the compounds of formula III are those wherein R5 is Cl, R6 and R7 are H, R8 is CH3, and Rg is cyclopropyl, and A is fraction (i) (commonly known as cyproconazole); those in which R5 and R6 are Cl, R7 and R8 are H, R9 is propyl, and A is the fraction (i) (commonly known as hexaconazole); those wherein R5 is 4-chlorophenoxy, R6 is Cl, R7 / R8, and R9 are H, and A is the fraction (ii) (commonly known as difenoconazole); those wherein R5 and Re are Cl, R7 and Rs are H, R9 is ethyl, and A is the fraction (ii) (commonly known as etaconazole); those in which R5 and R6 are Cl, R7 and Re are H, R9 is propyl, and A is the fraction (ii) (commonly known as propiconazole); those in which R5 is Cl, Rs is H, R7, Rs, and Rg are CH3, and A is the fraction (iii) (commonly known as tebuconazole); those where R5 is Cl, R6 is H, and A is the fraction (iv) (commonly known as triticonazole); those where R5 is H, R6 is F, Ri0 is 4-fluorophenyl, and A is the fraction (v) (commonly known as flutriafol); those where R5 is H, R6 is Cl, Rio 4-fluorophenyl, and A is the fraction (vi) (commonly known as epoxiconazole); those where R5 is Cl, R6 is H, Rn is phenyl, and A is the fraction (vii) (commonly known as fenbuconazole); those where R5 and R6 are Cl, and A is the fraction (viii) (commonly known as bromuconazole); those where R5 and Re are Cl, Ri2 is propyl, and A is the fraction (ix) (commonly known as penconazole); those wherein R 5 and Re are Cl, R 2 is allyloxy, and A is the fraction (ix) (commonly known as imazalil); those where R5 and Re are Cl, R12 is 1, 1, 2, 2-tetrafluoroethoxymethyl, and A is the fraction (ix) (commonly known as tetraconazole); those where R5 is H, R6 is H, R9 is CH3, Rio is 4-fluorophenyl, and A is the fraction (x) (commonly known as flusilazole); those in which R5 is chloro, R6 is hydrogen, R7 and Rs are methyl, and A is the fraction (xi) (commonly known as metconazole); those in which R5 and R6 are chloro, R7 and Rs are H, R9 is tertiary butyl, and A is the fraction (xii) (commonly known as diniconazole); those where R5 and Re are chlorine, and A is the fraction (xiii) (commonly known as fluquinconazole); those in which R5 is chloro, Re, R7, and Rs are H, R9 is normal butyl, and A is the fraction (xiv) (commonly known as myclobutanil); those where R5 is chlorine, R6 is H, R7 / Re, and g are methyl, and A is the fraction (xv) (commonly known as triadimenol); and those in which R5 is phenyl, R7, Rs, and R9 are methyl, and A is the fraction (xv) (commonly known as bitertanol). Particularly preferred mixing components of the compounds of formula IV are those wherein Ri3 is cyclododecyl (commonly known as dodemorf), or alkyl of 10 to 13 carbon atoms (commonly known as tridemorph), or 3- (4- tertiary butyl phenyl) -2-methylpropyl (commonly known as phenpropimorph). In a predominant manner, the cis position of the methyl groups in the morpholine ring is present in the compounds of the formula IV when used in the combinations of the invention. Particularly preferred blending components of the compounds of formula V are those wherein X and Y are O, and R14 is 2-methylphenoxymethyl (commonly known as cresoxim-methyl); or wherein X is NH, Y is N, and R 4 is 2,5-dimethylphenoxymethyl; or wherein X is O, Y is CH, and R 4 is 4- (2-cyanophenoxy) -pyrimidin-6-yloxy (commonly known as azoxyestrobin); or wherein X is O, Y is N, and R14 is 4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl. Particularly preferred mixing components of the compounds of formula VI are those wherein R 5 and R 6 are both chlorine (commonly known as phenpiclonil); or where R? 5 and Rie together form a bridge -0-CF2-0- (commonly known as fludioxonil). Particularly preferred mixing components of the compounds of formula VII are those wherein Ri7 is benzyl, R2i and R22 are methyl, and Ri8 is 1-methoxycarbonylethyl (commonly known as benalaxyl); or wherein Ri7 is 2-furanyl, R2i and R22 are methyl, and R? 8 is 1-methoxycarbonylethyl (commonly known as furalaxyl); or wherein Ri7 is methoxymethyl, R2? and R22 are methyl, and R8 is 1-methoxycarbonylethyl, or is (R) -1-methoxycarbonylethyl (commonly known as metalaxyl and R-metalaxyl); or wherein Ri7 is chloromethyl, R2? and R22 are methyl, and R? 8 is 1 A in where Z is CH (commonly known as orfurace); or wherein R17 is methoxymethyl, R2i and R22 are methyl, and Laugh is,? , wherein Z is N (commonly known as or oxadixyl); or where Ri7 is and Rie, R21 / and R •: 22 they are hydrogen (commonly known as carboxy). Particularly preferred blending components of the compounds of formula VIII are those in which Ri9 and R20 together form the bridge -CH2-CH = CH-CH2- (commonly known as captan); or where Ri9 and R20 together form the bridge = CH- CH = CH-CH = (commonly known as folpet). The compound of formula IX is commonly known as prochloraz. The compound of formula X is commonly known as triflümizole. The compound of the formula XI is commonly known as pirifenox. The compound of formula XII is commonly known as acibenzolar-S-methyl. The compound of the formula XIII is commonly known as chlorothalonil. The compound of the formula XIV is commonly known as cymoxanil. The compound of the formula XV is commonly known as dimetomorph. The compound of formula XVI is commonly known as famoxadone.

The compound of formula XVII is commonly known as fenhexamide. The compound of formula XVIII is commonly known as fenarimol. The compound of formula XIX is commonly known as fluazinam. The compound of the formula XX is commonly known as fosetyl-aluminum. The compound of formula XXI is commonly known as quinoxifene. The compound of formula XXII is commonly known as phenpropidine. The compound of formula XXIII is commonly known as spiroxamine. The compound of formula XXIV is commonly known as carbendazim. The compound of the formula XXV is commonly known as thiabendazole. The compound of formula XXVI is commonly known as etirimol. The compound of the formula XXVII is commonly known as triazoxide. The compound of formula XXVIII is commonly known as guazatine. The specific compounds b) mentioned in the preceding paragraphs are commercially available. Other compounds falling under the scope of the different groups of component b) can be obtained, according to procedures analogous to those known for the preparation of commercially available compounds. It has been found that the use of the compounds of the formulas II to XXVIII, in combination with the compound of the formula I, in a surprising and substantial manner, improve the effectiveness of the latter against fungi, and vice versa. Additionally, the method of the invention is effective against a broad spectrum of these fungi, which can be combated with the active ingredients of this method, when used exclusively. It is understood that the specific preferred mixtures according to the present invention are represented by the combinations of active ingredients of the formula I, or any of the subgroups of the formula I, or the specifically mentioned members of the subgroups with a second selected fungicide at from the group comprising pyrimethanil, cyprodinil, ciproconazole, hexaconazole, difenoconazole, etaconazole, propiconazole, tebuconazole, triticonazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, imazalil, tetraconazole, flusilazole, metconazole, diniconazole, fluquinconazole, myclobutanil, triadimenol, bitertanol , dodemorf, tridemorph, fenpropimorf, mancozeb, maneb, metiram, zineb, copper hydroxid, copper oxychloride, copper sulfate, oxina-copper, sulfur, cresoxime-methyl, azoxyestrobin, 2- [2- (2,5-dimethylphenoxymethyl) -phenyl] -2-methoximino-acetic acid N-methylamide, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, orfurace, oxadixyl, carboxy, captan, folpet, prochloraz, triflumizole, pirifenox, acibenzolar-S-methyl, chlorothalonil, cymoxanil , dimetomorf, famoxadona, fenhexamida, fenarimol, fluazinam, fosetil-aluminio, quinoxifeno, fenpropidina, espiroxamina, carbendazima, thiabendazol, etirimol, triazóxido, and guazatina. Of this group, a subgroup bl comprising combinations with ciproconazole, hexaconazole, difenoconazole, propiconazole, tebuconazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, tetraconazole, flusilazole, metconazole, diniconazole, triadimenol, fluquinconazole, and prochloraz is preferred. Of this group, combinations with propiconazole, difenoconazole, penconazole, tebuconazole, prochloraz, epoxiconazole, and ciproconazole are of particular interest, as the preferred embodiments of this invention as the bla subgroup. An additional preferred subgroup b2 comprises combinations with cyprodinil, tridemorph, phenpropimorf, cresoxim-methyl, azoxyestrobin, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, chlorothalonil, famoxadone, quinoxifene, fenpropidine, and carbendazim. Of this group, the * combinations with ciprodinil, fenpropimorf, cresoxima-methyl, azoxiestrobina, 2- are of particular interest. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-4-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, and phenpropidine, as the preferred embodiments of this invention, as subgroup b2a. Other combinations of interest are the following: The compound 1.01 with any group of members bl and b2, or with any member of the groups bla and b2a; Compound 1.02 with any group of members bl and b2, or with any member of groups bla and b2a; Compound 1.03 with any group of members bl and b2, or with any member of groups bla and b2a; Compound 1.04 with any group of members bl and b2, or with any member of groups bla and b2a; The compound 1.05 with any group of members bl and b2, or with any member of the groups bla and b2a; The compound 1.06 with any group of members bl and b2, or with any member of the groups bla and b2a; The compound 1.07 with any group of members bl and b2, or with any member of the groups bla and b2a; The compound 1.08 with any group of members bl and b2, or with any member of the groups bla and b2a.

The weight ratio of a): b) is selected such that a synergistic fungicidal action is given. In general, the weight ratio of a): b) is between 100: 1 and 1: 400. The synergistic action of the composition can be seen from the fact that the fungicidal action of the composition of a) + b) is greater than the sum of the fungicidal actions of a) and b). When component b) is an anilinopyrimidine of formula II, the weight ratio of a): b) is, for example, between 1: 2 and 1:36, especially between 1: 2 and 1:18, and more preferably between 1: 3 and 1: 8. When component b) is an azole fungicide of formula III, the weight ratio of a): b) is, for example, between 10: 1 and 1:20, especially between 5: 1 and 1:10, and more preferably between 2: 1 and 1: 4. When component b) is a morpholine fungicide of formula IV, the weight ratio of a): b) is, for example, between 1: 2 and 1:30, especially between 1: 3 and 1:15, and more preferably between 1: 3 and 1:10. When component b) is a strobilurin fungicide of formula V, the weight ratio of a): b) is, for example, between 2: 1 and 1:10, especially between 1: 1 and 1: 8, and more preferably between 1: 2 and 1: 5. When component b) is a pyrrole fungicide of formula VI, the weight ratio of a): b) is, for example, between 1: 3 and 1:30, especially between 1: 1.5 and 1: 7, and preferably between 1: 2 and 1: 5. When component b) is a phenylamide fungicide of formula VII, the weight ratio of a): b) is, for example, between 3: 1 and 1:12, especially between 2.5: 1 and 1: 6, more preferably between 2: 1 and 1: 3. When component b) is a dithiocarbamate fungicide, the weight ratio of a): b) is, for example, between 1: 3 and 1: 120, especially between 1: 4 and 1:60, and preferably between 1: 7 and 1:25. When component b) is a copper compound fungicide, the weight ratio of a): b) is, for example, d between 1: 1.5 and 1: 100, especially between 1: 2 and 1:50, and preferably between 1: 5 and 1:30. When component b) is a sulfur fungicide, the weight ratio of a): b) is, for example, between 1: 6 1: 400, especially between 1: 8 and 1: 200, and more preferably between 1 : 10 and 1: 100. When component b) is a phthalimide fungicide of formula VIII, the weight ratio of a): b) is, for example, between 1: 3 and 1:80, especially between 1: 4 and 1:40, more preferably between 1: 8 and 1:20. When component b) is the compound of formula IX, the weight ratio of a): b) is, for example, between 1: 2 and 1:25, especially between 1: 4 and 1:12, and more preferably between 1: 5 and 1: 8. When component b) is the compound of the formula X, the weight ratio of a): b) is, for example, between 3: and 1:16, especially between 2.5: 1 and 1: 8, and more preferably between 1: 1 and 1: 4. When component b) is the compound of the formula XI, the weight ratio of a): b) is, for example, between 8: 1 and 1: 4, especially between 2.5: 1 and 1: 2, and more preferably between 2: 1 and 1: 1. When component b) is the compound of the formula XII, the weight ratio of a): b) is, for example, between 6: 1 and 1: 2, especially between 6: 1 and 2: 1, and more preferably between 5: 1 and 2: 1. When component b) is the compound of the formula XIII, the weight ratio of a): b) is, for example, between 1: 3 and 1:40, especially between 1: 4 and 1:20, and more preferably between 1: 5 and 1:10. When component b) is the compound of formula XIV, the weight ratio of a): b) is, for example, between 3: 1 and 1: 8, especially between 2.5: 1 and 1: 4, and more preferably between 2: 1 and 1: 2. When component b) is the compound of the formula XV, the weight ratio of a): b) is, for example, between 1.5: 2 and 1:12, especially between 1: 1 and 1: 6, and more preferably between 1: 1 and 1: 4. When component b) is the compound of the formula XVI, the weight ratio of a): b) is, for example, between 1.5: 1 and 1:10, especially between 1: 1 and 1: 5, and more preferably between 1: 1 and 1: 3. When component b) is the compound of the formula XVII, the weight ratio of a): b) is, for example, between 2: 1 and 1:30, especially between 1.5: 1 and 1:15, and more preferably between 1: 1 and 1: 5. When component b) is the compound of the formula XVIII, the weight ratio of a): b) is, for example, between 8: 1 and 1: 4, especially between 2.5: 1 and 1: 2, and more preferably between 2: 1 and 1: 1. When component b) is the compound of formula XIX, the weight ratio of a): b) is, for example, between 1.5: 1 and 1:12, especially between 1: 1 and 1: 6, and more preferably between 1: 1 and 1: 4. When component b) is the compound of the formula XX, the weight ratio of a): b) is, for example, between 1: 3 and 1:80, especially between 1: 4 and 1:40, and more preferably between 1: 1 and 1:25. When component b) is the compound of the formula XXI, the weight ratio of a): b) is, for example, between 2: 1 and 1: 5, especially between 1.5: 1 and 1: 2.5, and more preferably between 1: 1 and 1: 2.

When component b) is the compound of the formula XXII, the weight ratio of a): b) is, for example, between 1: 2 and 1:30, especially between 1: 3 and 1:15, and more preferably between 1: 3 and 1:10. When component b) is the compound of the formula XXIII, the proportion in 'weight of a): b) is, for example, between 1: 2.5 and 1:30, especially between 1: 3 and 1:15, and more preferably between 1: 3 and 1:10. When component b) is the compound of formula XXIV, the weight ratio of a): b) is, for example, between 1.5: 1 and 1:10, especially between 1: 1 and 1: 5, and more preferably between 1: 2 and 1: 4. When component b) is the compound of the formula XXV, the weight ratio of a): b) is, for example, between 40: 1 and 1:10, especially between 20: 1 and 1: 5, and more preferably between 10: 1 and 1: 2. When component b) is the compound of the formula XXVI, the weight ratio of a): b) is, for example, between 1: 1 and 1:10, especially between 1: 1 and 1: 5, and more preferably between 1: 1 'and 1: 2. When component b) is the compound of the formula XXVII, the weight ratio of a): b) is, for example, between 10: 1 and 100: 1, especially between 5: 1 and 50: 1, and more preferably between 2: 1 and 20: 1. When component b) is the compound of formula XXVIII, the weight ratio of a): b) is, for example, between 5: 1 and 1: 4, especially between 3: 1 and 1: 2, and more preferably between 2: 1 and 1: 1. The method of the invention comprises applying to the plants to be treated, or to the place thereof, in mixture or separately, a fungicidally effective accumulated amount of a compound of the formula I, and a compound of the component b). The term "place", as used herein, is intended to encompass the fields in which the treated crop plants are being grown, or where the seeds of the cultivated plants are sown, or the place where the seeds will be placed. on earth. The term "seeds" is intended to encompass propagation material of plants, such as cuttings, seedlings, seeds, sprouted or soaked seeds. The novel combinations are extremely effective on a broad spectrum of phytopathogenic fungi, in particular of the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action, and can be used as foliar and earth fungicides. Fungicidal combinations are of particular interest to control a large number of fungi in different crops or their seeds, especially wheat, rye, barley, oats, rice, corn, meadows, cotton, soybeans, coffee, sugar cane, fruit , and ornamentals in horticulture and viticulture, and in vegetables, such as cucumbers, beans, and cucurbits. The combinations are applied by the treatment of fungi or seeds, plants or materials threatened by fungal attack, or soil, with a fungicidally effective amount of the active ingredients. The agents can be applied before or after the infection of the materials, plants, or seeds by fungi. The novel combinations are particularly useful to control the following plant diseases: Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea e cucurbitaceae, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in cereals, Species of Rhizoctonia in cotton, rice, and meadows, Species of Ustilago in cereals and sugar cane, Vanturia inaequalis (scab) in apples, Species of Helminthosporium in cereals, Septoria nodorum in wheat, Septoria tritici in wheat, Bhynchosporium secalis in barley, Pseudocercosporella herpotrichoides in wheat and barley , Pyricularia in rice, Phytophthora infestans in potatoes and tomatoes, Species of Fusarium and Verticillium in different plants, Plasmopara viticola in grapes, Species of Alternating in fruits and vegetables.

When applied to plants, the compound of formula I is applied in a concentration of 25 to 150 grams / hectare, particularly 20 to 125 grams / hectare, for example 75, 100, or 125 grams / hectare, in association with 20 to 3000 grams / hectare, particularly with 20 to 2,000 grams / hectare, for example, with 20 grams / hectare, 30 grams / hectare, 40 grams / hectare, 75 grams / hectare, 80 grams / hectare, 100 grams / hectare , 125 grams / hectare, 150 grams / hectare, 175 grams / hectare, 200 grams / hectare, 300 grams / hectare, 500 grams / hectare, 1,000 grams / hectare, 1,200 grams / hectare, 1,500 grams / hectare, 2,000 grams / hectare , or in some cases as sulfur up to 10,000 grams / hectare of a compound of component b), depending on the kind of chemical used as component b). When component b) is an anilinopyrimidine of formula II, for example, 300 to 900 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is an azole fungicide of the Formula III, for example, apply from 20 to 350 grams of active ingredient / hectare in association with the compound of formula I. When component b) is a morpholine of formula IV, for example, 300 to 750 are applied grams d active ingredient / hectare in association with the compound of formula I. When component b) is a strobilurin of formula V, for example, 75 to 250 grams of active ingredient / hectare are applied in combination with the compound of I formula I. When component b) is a pyrrole of formula VI, for example, 200 to 750 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is a phenylamide of formula VII, for example, 50 to 300 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is a dithiocarbamate, for example, from 500 to 3,000 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is a copper compound, for example, 250 to 2,500 grams of active ingredient are applied in association with the compound of formula I. When component b) is sulfur, for example, 1,000 to 10,000 grams of active ingredient in association with the compound of formula I. When component b) is a phthalimide of formula VIII, for example, 500 to 2,000 grams of active ingredient / hectare are applied in association with the compound of Formula I. When component b) is a compound of formula IX, for example, 400 to 600 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of Formula X, for example, are applied from 50 to 400 grams of active ingredient / hectare in association with the compound of formula I. When component b) is the compound of formula XI, for example, 20 to 100 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XII, for example, 20 to 40 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XIII , for example, 500 to 1,000 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XIII, for example, 500 to 1,000 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula Formula XIV, for example, 50 to 200 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XV, for example, 100 to 300 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XVI, for example, 125 to 250 grams of active ingredient / hectare in association with the compound of the formula I. When the component b) is the compound of the formula XVII, for example, 100 to 750 grams of active ingredient / hectare and association with the compound of the formula are applied I. When component b) is the compound of formula XVIII, for example, 20 to 100 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XIX, for example, 100 to 300 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XX, for example, 500 to 2,000 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XXI , for example, 75 to 125 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XXII, for example, 300 to 750 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XXIII, for example, 375 to 750 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XXIV, for example, 125 to 250 grams of active ingredient / hectare are applied in association with the compound of formula I. When component b) is the compound of formula XXV, for example, 5 to 200 grams of active ingredient / 100 kilograms are applied for seed coating in association with the compound of formula I. When component b) is the composed of formula XXVI, for example, 200 grams of active ingredient / 100 kilograms are applied for seed coating in association with the compound of formula I. When component b) is the compound of formula XXVII, for example, 2 grams of active ingredient / 100 kilograms are applied for seed coating in association with the compound of formula I. When component b) is the compound of formula XXVIII, for example, 40 to 80 grams of active ingredient / 100 kilograms are applied for seed coating in association with the compound of formula I. In agricultural practice, the application concentrations of the combination depend on the type of effect desired, and are from 0.02 to 4 kilograms of active ingredient per hectare. When the active ingredients are used for the treatment of seeds, in general, concentrations of 0.001 to 50 grams of active ingredient per kilogram, and preferably 0.01 to 10 grams per kilogram of seeds are sufficient. The invention also provides fungicidal compositions comprising a compound of the formula I and a compound of the component b).

The composition of the invention can be used in any conventional form, for example, in the form of a double pack, an instant granulate, a flowable or wettable powder in combination with agriculturally acceptable auxiliaries. These compositions can be produced in a conventional manner, for example, by mixing the active ingredients with the appropriate auxiliaries (diluents or solvents, and optionally other ingredients of formulations, such as surfactants). The term "diluent", as used herein, means any agriculturally acceptable liquid or solid material, including carriers that can be added to the active constituents to put them in an easier or better applicable form, respectively, up to a concentration of activity useful or desirable. Suitable solvents are: aromatic hydrocarbons, preferably fractions containing from 8 to 12 carbon atoms, for example mixtures of xylene or substituted naphthalenes, phthalates, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, or dimethylformamide, as well as vegetable oils, or epoxidized vegetable oils, such as coconut oil or epoxidized soybean oil; or water. The solid carriers used, for example, paw dry powders and dispersible powders, are usually natural mineral fillers, such as calcite, talc, kaolin, montmorillonite or attapulgite. In order to improve the physical properties, it is also possible to add highly dispersed salicylic acid or highly dispersed absorbent polymers. Suitable granular adsorbent carriers are porous types, for example pumice, broken septum, sepiolite or bentonite, and suitable nonabsorbent carriers are, for example, calcite or sand. In addition, a large number of materials of an inorganic or organic nature can be used, for example, especially dolomite or pulverized plant residues. Depending on the nature of the compounds of formula I and component b) to be formulated, suitable surface active compounds are nonionic, cationic, and / or anionic surfactants having good emulsifying, dispersing, and wetting properties. It will also be understood that the term "surfactants" comprises mixtures of surfactants. Particularly convenient promoters of the application are also natural or synthetic phospholipids of the cephalin and lecithin series, for example phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, and lysolecithin. Particularly, the formulations to be applied in spraying forms, such as water-dispersible concentrates or wettable powders, may contain surfactants, such as wetting and dispersing agents, for example, the condensation product of formaldehyde with naphthalenesulfonate, a sulfonate of alkylaryl, a lignin sulfonate, a fatty alkyl sulfate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol. A seed coating formulation is applied in a manner known per se to the seeds, using the combination of the invention and a diluent in a suitable seed coating formulation form, for example, as an aqueous suspension, or a form of dry powder that has good adhesion to the seeds. These seed coating formulations are known in the art. Seed coating formulations may contain the simple active ingredients, or the combination of active ingredients in an encapsulated form, for example, as slow-release capsules or microcapsules. In general, the formulations include 0.01 to 90 weight percent active agent, from 0 to 20 percent of agriculturally acceptable surfactant, and from 10 to 99.99 percent of solid or liquid auxiliaries, the active agent consisting of at least the compound of formula I together with a compound of component b), and optionally other active agents, particularly microbicides or preservatives, or the like. The concentrated forms of the compositions generally contain between about 2 and 80 percent, preferably between about 5 and 70 percent by weight of active agent. Forms of application of the formulation, for example, may contain 0.01 to 20 weight percent, preferably 0.01 to 5 weight percent active agent. The following Examples serve to illustrate the invention, by denoting "active ingredient" a mixture of compound I and a compound of component b) in a specific mixing ratio. The formulations can be prepared in a manner analogous to that described, for example, in International Publication Number WO 97/33890.

Slow Release Capsule Suspension 28 parts of a combination of the compound of the formula I and a compound of component b), or of each of these compounds separately, are mixed with two parts of an aromatic solvent and 7 parts of a mixture of toluene di-isocyanate / polymethylene polyalkylene isocyanate (8: 1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water, until the desired particle size is reached. To this emulsion. a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is completed. The capsule suspension obtained is stabilized by the addition of 0.25 parts of a thickener, and 3 parts of a dispersing agent. The capsule suspension formulation contains 28 percent of the active ingredients. The average capsule diameter is 8 to 15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a suitable apparatus for this purpose.

Pnrmnl ani? N Ht »• Rg reg-hi my ant -.o? A Seal 25 parts of a combination of the compounds of the formulas I and II, 15 parts of dialkylphenoxypoly (ethyleneoxy) ethanol, 15 parts of fine silica , 44 parts of fine kaolin, 0.5 parts of rhodamine B as a dye, and 0.5 parts of Xanthan Gum, are mixed and ground in a Contraplex mill at approximately 10,000 rpm, to an average particle size of less than 20 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a suitable apparatus for that purpose. Although the commercial products of preference will be formulated as concentrates, the end user will usually employ diluted formulations.

Biological Examples There is a synergistic effect provided that the action of the combination of active ingredients is greater than the sum of the actions of the individual components. The action to be expected E for a given combination of active ingredients, obeys the so-called formula of COLBY, and can be calculated as follows (COLBY, S.R. "Calculating t synergistic and antagonistic responses of herbicide combination", Weeds, Volume 15, pages 20-22, 1967): ppm = milligrams of active ingredient (= ia) per liter of spray mixture, X = Percentage of action per active ingredient I using p ppm of active ingredient, Y = Percentage of action per active ingredient II using q ppm of active ingredient .

According to COLBY, the expected action (additive) of the active ingredients I + II, using p + q ppm of active ingredient, is E = X + Y - X. And 100 If the actually observed action (O) is greater than the expected action (E), then the action of the combination is superadditive, that is, there is a synergistic effect. Alternatively, the synergistic action can also be determined from the dose response curves according to the so-called WADLEY method. With this method, the effectiveness of the active ingredient is determined by comparing the degree of fungal attack on the treated plants, with that on the untreated control plants, similarly inoculated and incubated. Each active ingredient is tested in four to five concentrations. Dose response curves are used to establish the EC90 (ie, the concentration of active ingredient that provides 90 percent disease control) of single compounds, as well as combinations (EC90 Observed). experimentally found in this manner of the mixtures in a given proportion by weight, are compared with the values that would have been found if only a complementary efficacy of the components was present (EC 90 (A + B) esaraa) • The EC 90 (A + B) esarada is calculated according to Wadley (Levi et al., EPPO Bulletin, 1986, 651-657): a + b EC 90 (A + B) expected = EC90 (A) observed EC90 (B) observed where a and b are the proportions by weight of compounds A and B in the mixture, and the indices (A), (B), (A + B) refer to the values of EC 90 observed of the compounds A, B, or of the given combination A + B thereof. The EC90 (A + B) e3perated / EC90 (A + B) proportion obserada expresses the interaction factor (F). In the case of synergism, F is > 1.

Example B-l: Efi pa .i a-contra- Érys ± phe-grramxn-a- f sp ~ tri tici The wheat plants, variety "Arina", approximately 10 days old, are sprayed with aqueous suspensions of the active ingredients or mixtures thereof. One day later, the plants are inoculated by sprinkling with spores of Erysiphe graminis. The tests can also be carried out with curative applications, that is, application of 1 to 3 days after the artificial inoculation of the plants. The plants are incubated in the greenhouse or in climatic chambers at 20 ° C with 70 percent relative humidity. From 7 to 10 days after the inoculation, the fungal attack on the primary leaves is evaluated.

Results: Table 1. Mixture I.01 + fludioxonil (compound VI, where R? 5 and íe together form a bridge -OCF2-0-) Table 2: Mixture of 1.01 + cyproconazole (compound III, wherein R5 is Cl, R6 and R7 are H, R8 is CH3, R9 is cyclopropyl, and A is fraction (i)) Table 3; Mixture of 1.01 + propiconazole (compound III, where Rs and R6 are Cl, R7 and R8 are H, R9 is propyl, and A is the fraction (ii)) Table 4; Mixture of 1.01 + fenpropidine (compound XXII) Example B-2: Efficacy against Erysiphe gramiriis f. sp. hardei in barley a_) Protective or decorative activity Barley plants, variety "Golden Promise" are used. The test procedure is the same as that described in Example Bl. * b Achí vi dad siaté-mi ca Aqueous spray mixtures of the active ingredients or mixtures thereof are then watered from the barley plants approximately 8 centimeters high. Care is taken that the spray mixture does not come into contact with the aerial parts of the plants. 48 hours later, the plants are sprinkled with conidia of the fungus. The infected plants are placed in a greenhouse at 22 ° C. The attack of the disease on the foliage is evaluated 12 days after infection.

Example B-3: Activity against Podosphaera le cotricha in apples The apple seedlings with fresh sprouts 10 centimeters long, are sprayed with aqueous spray mixtures of the active ingredients or mixtures thereof. The treated plants are inoculated 24 hours later with a suspension of conidia of the fungus, and are placed in a climatic chamber with 70 percent relative humidity and at 20 ° C. The test can also be performed with curative application 2 days after the inoculation. The attack of the disease is evaluated 12-14 days after the inoculation.

Example B-4: Activity against Oncinula. necator in grapes Grape plants grown from seeds (variety "Gutedel"), in the 4- to 5-leaf stage, are sprayed with aqueous spray mixtures of the active ingredients or mixtures thereof. One day later, the treated plants are inoculated with a spore suspension of Uncinula necator, and then incubated in a culture chamber at + 24 ° C and with 70 percent relative humidity. The test can also be performed using curative application 2 days after inoculation. The attack of the disease is evaluated 14 days after the inoculation.

Example B-5: Activity against Sphaerotheca fuliginea on cucumbers The cucumber seedlings, variety "chinesische Schlan-ge", about 2 weeks old (cotyledon stage), are sprayed with aqueous spray mixtures of the active ingredients or of the mixtures thereof. One day later, the treated plants are inoculated with a spore suspension of Sphaerotheca fuliginea, and then incubated in a culture chamber at + 24 ° C and with 70 percent relative humidity. The test can also be performed using curative application 2 days after inoculation. The attack of the disease is evaluated 10 days after inoculation.

Example B-fí: -Activity against non-organic water in apples The apple seedlings, with fresh shoots of approximately 10 centimeters long, are sprayed with aqueous spray mixtures of the active ingredients or mixtures thereof. The treated plants are inoculated 24 hours later with a suspension of conidia of the fungus. The plants are incubated for 2 days at + 20 ° C and with 95-100 percent relative humidity, then another 10 days in the greenhouse at 20-24 ° C and with 80 percent relative humidity. The attack of the disease is evaluated on the younger treated leaves.

• R-7 • An +? H HaH rv-m-t-r »T inn-t ni a ror? N i f-a < * r? + -. t »i gr > The wheat plants, variety "Arina", of approximately 10 days of age, are sprayed with aqueous suspensions of the active ingredients or mixtures thereof. One day later, the plants are inoculated with a spore suspension of the fungus. The test can also be performed with healing applications, that is, application of 1 to 3 days after the artificial inoculation of the plants. The plants are incubated in a culture chamber for 2 days at 20 ° C and at 95-100 percent relative humidity, and then for another 10 days at 20 ° C and at 70 percent relative humidity. The fungal attack on the primary leaves is evaluated.

Ta »i» * • Mixture of 1.01 + Compound V, where X is O, Y is N, Example B-8: Activity against Septoria nadorxim fvn wheat Wheat plants, variety "Zenith", approximately 10 days old, are sprayed with aqueous suspensions of the active ingredients or mixtures thereof. One day later, the plants are inoculated with a spore suspension of the fungus. The tests can also be done with healing times, that is, application of 1 to 3 days after the artificial inoculation of the plants. The plants are subsequently incubated in a culture chamber with a relative atmospheric humidity of 95 to 100 percent. The attack of the disease is evaluated 10 days after the inoculation. • p. tain lo BQ: Acti i ad against Plasmopara I saw tícola in vines Grape plants cultivated from seeds (variety "Gutedel"), in the stage of 4 to 5 leaves, are sprayed with aqueous spray mixtures of the active ingredients or the mixtures thereof. One day later, the treated plants are inoculated with a spore suspension of the fungus. The plants are incubated in a culture chamber for 2 days at + 22 ° C, and with a relative humidity of 95 to 100 percent, then 4 days at 22 ° C and 70 percent relative humidity, followed again by a day with high humidity, to induce sporulation. The attack of the disease is evaluated 7 days after the inoculation.

EjsHn l "* R-1 f) t ArrH vi aH cmni-.ra Vhyr-nph + ihnr-a íp-Ft * a j? T? S in j i tomatoes The tomato plants, variety "Baby", of approximately 4 weeks of age, are sprayed with aqueous spray mixtures of the active ingredients or mixtures thereof. One day later, the treated plants are inoculated with a suspension of zoospores of the fungus. The plants are incubated for 6 days in humidity chambers at 18 ° C and with 100 percent relative humidity. After this period, the attack of the disease is evaluated.

The efficacy of the test combinations and the simple active ingredients in the above tests is determined by comparing the degree of fungal attack with that on the untreated control plants, similarly inoculated.

Example B-ll: Activity against Gerlachia níval is in wheat Wheat seeds, which are infected with G. nivalis, are harvested from the field. These seeds are treated with one of the ingredients I or b), or with mixtures of the active ingredients. The active components are first dispersed in water, and this dispersion is then sprayed onto the seeds, which are on a rotating disk. This procedure corresponds to the conditions found in practice. Untreated seeds of the same origin are used for comparison purposes.

Seeds of 100 grains are planted in seed trays (45 x 35 x 10 centimeters) in sterile soil at a depth of 2 centimeters. Three replicas of the test are made. The seed trays are kept moist for 21 days at 5 ° C with the exclusion of light. Then they are transferred to a control environment cabinet with lighting (day / night: 16/8 hours, IOCJC), where the emergence takes place. Germination does not take place in the case of those grains that are very infected with G. nivalis. After 10 days, the trays are covered with a plastic film, and kept at 10 ° C without light. Due to the high atmospheric humidity below the cover, the fungal mycelium becomes apparent on the base of the stem of those plants that are infected with G. nivalis. Approximately 60 days after sowing, the number of existing plants and the number of infected plants are determined. The sum of the number of ungerminated grains and the number of infected plants forms the total infection rate. This index is compared with the total infection rate in the seed trays of comparison with untreated seeds, and is expressed as the total percentage of infection index.

Example B-12: Activity against H 7 mi nthosporitpn grami evaa in barley Barley seeds, which are infected with H. grami -neum, are harvested from the field. These seeds are treated with one of the active ingredients I or b), or with mixtures of the active ingredients. The active components are first dispersed in water, and this dispersion is then sprayed onto the seeds, which are on a rotating disk. This procedure corresponds to the conditions found in practice. Untreated seeds of the same origin are used for comparison purposes. Seeds of 100 grains are planted in seed trays (45 x 35 x 10 centimeters) in sterile soil at a depth of 2 centimeters. Three replicas of the test were made. The seed trays are kept moist for 28 days at 2 ° C with the exclusion of light. Then they are transferred to a greenhouse (day / night: 18/12 ° C). Approximately 60 days after sowing, the number of existing plants and the number of infected plants are determined. Symptoms are expressed as typical spots in the form of stripes on the first leaf. The total infection rate is compared to the total infection rate in the seed trays of comparison with untreated seeds, and is expressed as the total percentage of infection index.

Mixture of 1.01 + triticonazole (compound III where Rs is Cl, Re is H, and A is fraction (iv)) v.j «atnpl r, * R-13: rj-h-ivi ad pr > n-t-a Septoria nndornm in wheat Wheat seeds infected with S. nodoru are harvested from the field. These seeds are treated with one of the active ingredients I or b), or with mixtures of the active ingredients. The active components are first dispersed in water, and this dispersion is then sprayed onto the seeds that are on a rotating disk. This procedure corresponds to the conditions found in practice. Untreated seeds of the same origin are used for comparison purposes.

The test method used is based on the one published by Holmes and Colhoun (Ann. Of appl. Biol., 1973, 225-232). Seeds of 100 grains are planted in seed trays (45 x 35 x 10 centimeters) in sterile soil at a depth of 2 centimeters. Three replicas of the test are made. The seed trays are kept moist for 14 days at 8-10 ° C with the exclusion of light. They are then transferred to a greenhouse (20 ° C) for a period of another 14 days. After that, the seedlings are removed from the soil, and washed with water before the infection is evaluated. The total infection rate is compared to the total infection rate in the seed trays of comparison with untreated seeds, and is expressed as the total percentage of infection index.

Example B-14 Ac vi ity with 7-3- Erysiphe gram ± xx ± -in barley or wheat The cereal seeds are treated with one of the active ingredients I or b), or with mixtures of the active ingredients. The active components are first dispersed in water, and this dispersion is then sprayed onto the seeds that are on a rotating disk. This procedure corresponds to the conditions found in practice. Untreated seeds of the same origin are used for comparison purposes. Seeds of 100 grains are planted in seed trays (45 x 35 x 10 centimeters) in sterile soil at a depth of 2 centimeters. Three replicas of the test are made. Seeds emerge under controlled conditions (day / night: 15/10 ° C). In the 2 to 3 leaf stage, the plants are inoculated artificially by shaking the highly infected plants on the test trays. Then the seed trays are kept at high temperatures (day / night: 22/18 ° C). Evaluations of the percentage of area of the infected leaf are made at regular intervals. The total infection rate is compared with the total infection rate e? the seed trays for comparison with untreated seeds, and is expressed as the total percentage of infection index.

The mixtures according to the invention exhibit good activity in these Examples.

Claims (10)

BETVTNnTCACTONES

1. A method for combating phytopathogenic diseases in crop plants, which comprises applying to the crop plants or to the place thereof which is infested with the phytopathogenic disease, an effective amount of: a) a thieno derivative [2, 3 d] pyrimidin-4-one of the formula I: wherein: Ri is halogen, R2 is alkyl of 1 to 5 carbon atoms, -CH2-cyclopropyl, and R3 is alkyl of 1 to 5 carbon atoms, -CH-cyclopropyl; in association with an amount of: b) either an anilinopyrimidine of formula II: wherein: R4 is methyl, 1-propynyl, or cyclopropyl; or an azole of the formula III: where: A is selected from: CN (xiii) C-CH2- and, CRy ßRg wherein the β-carbon atom is attached to the benzene ring of the formula III, and wherein: R 5 is H, F, Cl, phenyl, 4-fluorophenoxy, or 4-chlorophenoxy; R5 is H, Cl, or F; R7 and Re are independently H or CH3; R9 is alkyl of 1 to 4 carbon atoms or cyclopropyl; Rio is 4-chlorophenyl or 4-fluorophenyl; Rn is phenyl, and R12 is allyloxy, alkyl of 1 to 4 carbon atoms, or ljl, 2, 2-tetrafluoroethoxymethyl, and the salts of this azole fungicide; or a morpholine fungicide of formula IV: H3C NR 13 (IV) H3C wherein: R13 is cycloalkyl of 8 to 15 carbon atoms, alkyl of 8 to 15 carbon atoms, or alkyl of 1 to 4 carbon atoms-phenylalkyl of 1 to 4 carbon atoms, and the salts of this morpholine fungicide; or a strobilurin compound of the formula V: wherein: X is NH or O, Y is CH or N, and Ri4 is 2-methylphenoxymethyl, 2,5-dimethylphenoxymethyl, 4- (2-cyanophenoxy) pyrimidin-6-yloxy, or 4- (3-trifluoromethylphenyl) - 3-aza-2-oxa-3-pentenyl; or a pyrrole compound of the formula VI: wherein: Ris and Rie are independently halogen, or together form a perhalomethylenedioxo bridge; or a phenylamide of formula VII: wherein: R 7 is benzyl, methoxymethyl, 2-furanyl, chloromethyl, Ris is 1-methoxycarbonylethyl, or? Or Z is CH or N, R2? is hydrogen or methyl, R22 is hydrogen or methyl; or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram, and zineb; or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate, and oxine-copper; or sulfur; or a phthalimide compound of the formula VIII: wherein: R-19 and R2o together form a four-membered bridge -CH2-CH = CH-CH2- or = CH-CH = CH-CH =; or with a compound of the formula IX: Cl? 3H7-n / ^ N c? - w // - ° - ° H ~ CH-N-CO-N (IX) Cl or with a compound of the formula X: or with a compound of formula XI or with a compound of formula XII: COSCH3 (XII) or with a compound of formula XIII: or with a compound of the formula XIV: CN (XIV) H3C-CH2- NH- NH- "N-OCH, or with a compound of the formula XV: or with a compound of formula XVI: or with a compound of formula XVII: or with a compound of formula XVIII (XVIII) or with a compound of formula XIX: or with a compound of the formula XX: or with a compound of formula XXI or with a compound of formula XXII or with a compound of formula XXIII: (XXIII) or with a compound of formula XXIV: or with a compound of formula XXV: or with a compound of formula XXVI: or with a compound of formula XXVII (XXVII) or with a compound of formula XXVIII: (XXVIII) wherein: n is 0 or 1 or 2, et cetera, and R is hydrogen or -C (= NH) NH 2; which synergistically improves activity against phytopathogenic diseases. A method according to claim 1, wherein component a) comprises a compound of formula I wherein Ri is chlorine or bromine, and R2 is normal propyl, normal butyl, isobutyl, and R3 is normal propyl, butyl normal, isobutyl. 3. A method according to any of claims 1 to 2, wherein component b) is selected from the group comprising pyrimethanil, ciprodinil, ciproconazole, hexaconazole, difenoconazole, etaconazole, propicone-zol, tebuconazole, triticonazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, imazalil, tetraconazole, flusilazole, metconazole, diniconazole, fluquinconazole, myclobutanil, triadimenol, bitertanol, dodemorf, tridemorph , fenpropimorf, mancozeb, maneb, metiram, zineb, copper hydroxide, copper oxychloride, copper sulfate, oxina-copper, sulfur, cresoxim-methyl, azoxyestrobin, N-methylamide of 2- [2- (2,5- dimethylphenoxymethyl) -phenyl] -2-methoximino-acetic, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, orfurace, oxadixyl, carboxy, captan, folpet, prochloraz, triflumizole, pirifenox, acibenzolar-S-methyl, chlorothalonil, cymoxanil , dimetomorf, famoxadone, fenhexamide, fenarimol, fluazinam, fosetil-aluminum, quinoxifen, fenpropidin, spiroxamine, carbendazim, thiabendazole, etirimol, triazoxide, and guazatine, preferably selected from the group comprising ciproconazole, hexaconazole, difenoconazole, propiconazole, tebuconazole , flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, tetraconazole, flusilazole, metconazole, diniconazole, triadimenol, fluquinconazole, and prochloraz; and especially propiconazole, difenoconazole, penconazole, tebuconazole, prochloraz, epoxiconazole, and ciproconazole, more specifically selected from a group comprising cyprodinil, tridemorph, fenpropimorf, cresoxim-methyl, azoxyestrobin, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, chlorothalonil, famoxadone, quinoxifene, fenpropidine, and carbendazim; and especially ciprodinil, fenpropimorf, cresoxima-methyl, azoxyestrobina, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-4-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, and phenpropidine. 4. A method according to claim 3, wherein component a) is selected from the group comprising compound I.01, compound 1.02, compound 1.03, compound 1.04, compound 1.05, compound 1.06 , compound 1.07, and compound 1.08. A fungicidal composition comprising a fungicidally effective combination of component a) and component b) as defined in claim 1, wherein the components are present in amounts that synergistically improve activity against phytopathogenic diseases. 6. A composition according to claim 5, wherein the weight ratio of a) to b) is between 100: 1 and 1: 400 A composition according to claim 5, wherein component a) comprises a compound of formula I, wherein R x is chlorine or bromine, R 2 is normal propyl, normal butyl, isobutyl, and R 3 is normal propyl, butyl normal, isobutyl. A composition according to any of claims 6 or 7, wherein component b) is selected from the group comprising pyrimethanil, cyprodinil, ciproconazole, hexaconazole, difenoconazole, ethaconazole, propiconazole, tebuconazole, triticonazole, flutriafol, epoxiconazole , fenbuconazole, bromuconazole, penconazole, imazalil, tetraconazole, flusilazole, metconazole, diniconazole, fluquinconazole, myclobutanil, triadimenol, bitertanol, dodemorf, tridemorph, phenpropimorf, mancozeb, maneb, metiram, zineb, copper hydroxide, copper oxychloride, copper sulfate , oxine-copper, sulfur, cresoxim-methyl, azoxyestrobin, 2- [2- (2,5-dimethylphenoxymethyl) -phenyl] -2-methoximino-acetic acid N-methylamide, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, orfurace, oxadixyl, carboxy, captan, folpet, prochloraz, triflumizole, pirifenox, acibenzolar-S-methyl, chlorothalonil, cymoxanil , dimetomorf, fa oxadone, fenhexamide, fenarimol, fluazinam, fosetyl-aluminum, quinoxifen, fenpropidine, spiroxamine, carbendazim, thiabendazole, etirimol, triazoxide, and guazatine, preferably selected from the group comprising ciproconazole, hexaconazole, difenoconazole, propiconazole, tebuconazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, tetraconazole, flusilazole, metconazole, diniconazole, triadimenol, fluquinconazole, and prochloraz; and especially propiconazole, difenoconazole, penconazole, tebuconazole, prochloraz, epoxiconazole, and ciproconazole, more specifically selected from a group comprising cyprodinil, tridemorph, fenpropimorf, cresoxim-methyl, azoxyestrobin, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-3-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, chlorothalonil, famoxadone, quinoxifene, fenpropidine, and carbendazim; and especially ciprodinil, fenpropimorf, cresoxima-methyl, azoxyestrobina, 2-. { 2- [4- (3-trifluoromethylphenyl) -3-aza-2-oxa-4-pentenyl] -phenyl} -2-methoxy-imino-methyl acetate, acibenzolar-S-methyl, and phenpropidine. A composition according to claim 8, wherein component a) is selected from the group comprising compound I.01, compound 1.02, compound 1.03, compound 1.04, compound 1.05, compound 1.06 , compound 1.07, and compound 1.08. 10. A method according to claim 1, I for the treatment of propagation material of plants, preferably seeds.