NZ263170A

NZ263170A - Fungicidal mixture of a methoxyimino phenylacetic acid derivative, a morpholine or piperidine derivative and one of a series of azole derivatives

Info

Publication number: NZ263170A
Application number: NZ263170A
Authority: NZ
Inventors: Reinhold Saur; Manfred Hampel; Klaus Schelberger; Eberhard Ammermann; Gisela Lorenz
Original assignee: Basf Ag
Priority date: 1993-03-23
Filing date: 1994-03-10
Publication date: 1996-04-26
Also published as: JPH08508019A; CZ245695A3; HU9502779D0; RU2129371C1; AU676031B2; PL173281B1; HUT72732A; ATE144371T1; EP0690672A1; CZ288340B6; JP3611572B2; HU216718B; IL108653A0; UA29473C2; CN1119824A; KR100316043B1; EP0690672B1; IL108653A; DE4309272A1; ES2092903T3

Abstract

The invention concerns a fungicidal mixture comprising (a) alpha -methoximino-2-[(2-methylphenoxy)methyl]-phenylacetic acid methyl ester represented by formula (I) and (b) 4-(2-methyl-3-[4-tert.-butylphenyl]-propyl)-2,6-dimethylmorpholine (fenpropimorph) represented by formula (II) or the active substance tridemorph or the active substance fenpropidin and (c) the active substance prochloraz or another azol active substance. The invention also concerns a method of controlling fungi using this mixture.

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £63170 New Zeeiand No. 263170 International No. PCT/EP94/00741 i Priority Da! :f3): v. ;u i'oJ: ].o|'3. |94r. ....... ■;.) toQxti.&i/sa't AOI.to.|S#rtlfPrfcS^.SjWi QP.\ftl.5£/.J&; ..Ao>..N.Ha./.a5i ...2.6 APR. 1936 V\ f.4r!Q3. , •• NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION Title of Invention: Fungicidal mixture Name, address and nationality of applicant(s) as in international application form: BASF AG, of D-67056 Ludwigshafen, Federal Republic of Germany A G-&rnr\cyir\ 0050/43931 263170 Fungicidal composition The present invention relates to fungicidal compositions having a 5 synergistic fungicidal action and methods of combating fungi with these compositions. It is known (EP 253 213) to use methyl a-methoximino-2-[(2-me-thylphenoxy)-methyl]-phenylacetate 10 0— ch2 c=noch3 15 ^ H3COOC as a fungicide. It is also known (DE 26 56 747) to use the active ingredient 4-(2-methyl-3-[4-tert.-butylphenyl]-propyl)-2,6-dime-thylmorpholine 20 ch3 ch3 /ch3 I /=\ I / ( ch3 c—^ a ch2—ch—ch2— n o 25 I ^ CH3 CH3 or the active ingredient tridemorph or the active ingredient fen-propidin or salts thereof as fungicides. 30 It is further known (EP 72 156) to use N-propyl-N-[2,4,6-trichlo-rophenoxy)-ethyl]imidazole-l-carboxamide 35 r~L r CI V \—O [CH2]2 N C—N || V=N CI 40 as a fungicide. Furthermore, numerous azole active ingredients are known which have a fungicidal action, namely 45 263170 (Z)-2-[1,2,4-triazol-l-ylmethyl)-2-(4-fluorophenyl)-3- (2-chloro-phenyl)-oxirane of the formula 1-butyl-l-(2,4-dichlorophenyl)-2-(1,2,4-triazol-l-yl)-ethanol (common name hexaconazole) , 1-(4-fluorophenyl)-1-(2-fluorophenyl)-2-(1,2,4-triazol-l-yl)-ethanol (common name flu-triafol), (RS)-4-(4-chlorophenyl)-2-phenyl-2-(lH-l,2,4-triazol-l-ylmethyl ) -butyronitrile, 1— E(2 RS, 4 RS; 2 rs, 4 sr)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofurfuryl]-1H-1,2,4-triazole, 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-tria-zol-l-yl)-quinazolin-4(3H)-one, (rs)-2,2-dimethyl-3-(2-chloroben« zyl)-4-(1H-1,2,4-triazol-l-yl)-butan-3-ol, bitertanol, triadime-fon, triadimenol, cyproconazole, dichlobutrazol, difenoconazole, diniconazole, etaconazole, propiconazole, flusilazole, tebucona-zole, imazalil, penconazole, tetraconazole or a salt of such an azole active ingredient. We have now found that a composition of a) methyl o-methoximino-2-[ (2-methylphenoxy) -methyl] -phenylace-tate jp ch2 j H3 coof c=noch3 N.Z. PATENT OFF»Ce 2 2 FEB 1998 RECEIVED and b) 4-(2-methyl-3-[4-tert.-butylphenyl]-propyl)-2,6-dimethylmor-pho1ine (fenprop imorph) CH3 CHj—C-T. /J ch3 ch3 r-( CH2 CH CH2— N 0 ch3 ch3 263170 or the active ingredient tridemorph or the active ingredient fenpropidin and c) an azole active ingredient selected from the group consisting of N-propyl-N- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1-carboxamide Pr I /=] [CH2] 2 N C—N I \=N (Z)-2-(1,2,4-triazol-l-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane of the formula N.Z. PATHMT OFRCt" 2 2 FEB 1996 RECEIVED 1-butyl-l- (2,4-dichlorophenyl) -2- (1,2,4-triaz.ol-l-yl) -ethanol (common name hexaconazole), 1-(4-fluorophenyl)-1-(2-fluorophenyl)-2-(1,2,4-tri-azol-l-yl) -ethanol (common name flutriafol), (RS)-4- (4-chlo-rophenyl)-2-phenyl-2-(1H-1,2,4-triazol-l-ylmethyl)-butyroni-trile, 1-t(2 RS, 4 RS; 2 RS, 4 SR)-4-bromo-2-(2,4-dichlorophenyl )-tetrahydrofurfuryl]-1H-1,2,4-triazole, 3-(2,4-dichlorophenyl )-2-(1H-1,2,4-triazol-l-yl)-quinazolin-4(3H)-one, (RS)-2,2-dimethyl-3-(2-chlorobenzyl)-4-(1H-1,2,4-tria-zol-l-yl)-butan-3-ol, bitertanol, triadimefon, triadimenol, cyproconazole, dichlobutrazol, difenoconazole, diniconazole, etaconazole, propiconazole, flusilazole, tebuconazole, imaza-lil» penconazole, tetraconazole and a salt of such an azole active ingredient, has a synergistic fungicidal action. The weight ratio of compounds a), b) and c) is selected in such a way as to give a synergistic fungicidal action, for example a) :b) :c) of from 0050/43931 263170 4 10 to 1:10 to 1:10 to 1, for instance 5 to 1:5 to 1:5 to 1, especially 3 to 1:3 to 1:3 to 1, and preferably 2 to 1:2 to 1:2 to 1. The ratio of a):b):c) may for example be 10:1:1 to 1:10:1 to 1:1:10. The synergistic action of the composition 5 is apparent from the fact that the fungicidal action of the composition of a) + b) + c) is greater than the sum of the fungicidal actions of a), of b) and of c). With regardd to the -C=N double bond, component a) may be 10 present in two stereoisomeric forms. The (E) isomer is preferred. The invention embraces compositions containing the pure isomers of compound a), especially the (E) isomer, and composi-15 tions containing mixtures of the isomers. 20 25 The component fenpropimorph may be present in two stereoisomeric forms (morpholine ring), the cis isomer being preferred. The invention embraces compositions containing the pure isomers of the compound fenpropimorph, especially the cis isomer, and'compositions containing mixtures of the isomers. Compositions containing component a) predominantly as (E) isomer and at the same time component b) predominantly as cis isomer are preferred. 30 o— ch2 och3 H3COOC a, (E) isomer 35 40 ch3 ch3 -'c-J/ w ch3 ch3 ch2 ch ch2 rt 0 ch3 ch3 b, cis isomer 45 The active ingredient fenpropimorph b) may also be present in the form of its salts. These compositions too are embraced by the invention. 0050/43931 26 3 1 7 Salts are produced by reaction with acids, e.g., hydrohalo acids such as hydrofluoric acid, hydrochloric acid, hydro-bromic acid and hydroiodic acid, or sulfuric acid, phosphoric acid, nitric acid, or organic acids such as acetic acid, tri-5 fluoracetic acid, trichloroacetic acid, propionic acid, gly-colic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzenesul-fonic acid, p-toluenesulfonic acid, methanesulfonic acid, salicylic acid, p-aminosalicylic acid or 1,2-naphthalenedi-10 sulfonic acid. In practice, the pure active ingredients a), b) and c) are advantageously used, to which further active ingredients such as insecticides, acaricides, nematicides, herbicides, other 15 fungicides, growth regulatores and/or fertilizers may be added. The fungicidal compositions according to the invention may be applied for instance in the form of directly sprayable solutions, 20 powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are 25 being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible. Normally, the plants are sprayed or dusted with the compositions or the seeds of the plants are treated with the compositions. 30 The formulations are.produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic 35 solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatic s (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylforma-40 mide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dis-45 persants such as lignin-sulfite waste liquors and methylcellu-lose. 0050/43931 26 3 1 6 Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsul-fonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and 5 alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naph-10 thalenesulfonic acids with phenol and formaldehyde, polyoxyethy-lene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide 15 condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose. 20 Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier. Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. 25 Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, lov.'s, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium 30 phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc. The compositions are extremely effective on a broad spectrum of 35 phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and may be used as foliar and soil fungicides. The fungicidal compositions are of particular interest for con-40 trolling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits. 45 0050/43931 26 3 170 7 The compounds are applied by treating the seeds, plants, materials or soil to be protected against fungus attack with a fungi-cidally effective amount of the active ingredients. 5 The compounds may be applied before or after infection of the materials, plants or seeds by the fungi. The compositions are particularly useful for controlling the following plant diseases: 10 Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Oncinula necator in vines, 15 Puccinia species in cereals, Rhizoctonia solani in cotton, Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, 20 Septoria nodorum in wheat, Rhynchosporium in cereals, Botrytis cinerea (gray mold) in strawberries and grapes, Cercospora arachidicola in groundnuts, Pseudocercosporella herpotrichoides in wheat and barley, 25 Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, Fusarium and Verticillium species in various plants, Plasmopara viticola in grapes, Alternaria species in fruit and vegetables. 30 The novel compositions may also be used for protecting materials (timber), for example against Paecilomyces variotii. The fungicidal agents generally contain from 0.1 to 95, and pre-35 ferably from 0.5 to 90, wt% of active ingredient. The application rates depend on the type of effect desired, but are generally from 0.01 to 3 kg of active ingredient composition per hectare. 40 When the compositions are used for treating seed, application rates of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required. 45 0050/43931 26 3 170 Biological experiments Example 1 5 Eradicative action on wheat mildew Wheat plants of the "Kanzler" variety were inoculated at the 3-leaf stage with triazole-resistant wheat mildew (Erysiphe gra-minis var. tritici) and treated at a degree of fungus attack of 10 about 30% with aqueous active ingredient formulations in the concentrations given. The amount of water corresponded to 200 1/h. The plants were cultivated in the greenhouse for 20 days at 10 to 22°C. The experiment was then evaluated by determining the leaf area under attack in percent. These figures were converted into 15 degrees of action. The expected degrees of action of the active ingredient composition were determined by the Colby formula (Colby, S.R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, S.. 20-22, 1967) and compared with the degrees of action observed. 20 The values for the fungicidal action varied between the various experiments because the plants exhibited varying degrees of attack, which meant that' the figures for the fungicidal action vary too. For this reason, only the results within the same experiment 25 can be compared with one another. Colby formula E = x + y - x-y/100 E = expected degree of action, expressed in % of the untreated 30 control, when active ingredients A and B are used in concentrations of m and n x = degree of action, expressed in % of the untreated control, when active ingredient A is used in a concentration of m 35 y = degree of action, expressed in % of the untreated control, when active ingredient B is used in a concentration of n 40 45 0050/43931 2 6 3 1 7 Active ingredient I. methyl a -methoximino-2- [ (2-methylphenoxy) -methyl] -pheny- lacetate 10 15 20 25 30 35 h3coo<5^ II. (±)-cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-di- methylmorpholine (fenpropimorph) ch3 ch3 ch3 / \ ch3 c—v v ch2 ch ch2 n 0 ch3 ch3 III. 2-(1,2,4-triazol-l-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane (epoxiconazol) XT - =. IV. 1-(N-propyl-N-2-(2,4,6-trichlorophenoxy)ethylcarba- moyl)imidazole (prochloraz) 40 V. Active ingredient combination Active ingredient I 45 + fenpropimorph 105 : 210 0050/43931 10 VI. Active ingredient combination Active ingredient I + epoxiconazol 1 : 1 ■26 3 1 7 0 10 15 20 VII. Active ingredient combination Active ingredient I + prochloraz 1:1 VIII. Active ingredient combination fenpropimorph + prochloraz 281 : 200 IX. Active ingredient combination f enpr op imorph + epoxiconazol 3 : 1 Table 1 Erysiphe graminis test (wheat) eradicative Triazole-resistant Erysiphe graminis 25 Active ingredient (a.i.) Active ingredient concentration in the spray liquor in % Degree of action in % of the untreated control Control (untreated) - 0 I. prior art a.i. EP 253 213 0.05 50 II. prior art a.i. fenpropimorph, DE 2 656 747 0.05 47 III. prior art a.i. epoxiconazol 0.05 26 IV. prior art a.i. prochloraz, EP 72 156 0.05 24 V. prior art a.i. combination a.i. I + fenpropimorph EP 524 496 0.05 65 VI. prior art a.i. combination a.i. I + epoxiconazol EP 531 837 0.05 52 VII. prior art a.i. combination a.i. I + prochloraz EP 531 837 0.05 52 30 35 40 45 0050/43931 263170 5 Active ingredient (a.i.) Active ingredient concentration in the spray liquor in % Degree of action in % of the untreated control VIII. prior art a.i. combination fenpropimorph + prochloraz 0.05 48 IX. prior art a.i. combination fenpropimorph + epoxiconazol EP 425 857 0.05 50 10 Compositions according to the invention 15 20 I. + VIII. ratio 1:3 0.01 + 0.03 58 I. + IX. ratio 1:3 0.01 + 0.03 62 II. + VI. ratio 1:3 0.01 + 0.03 61 II. + VII. ratio 1:3 0.01 + 0.03 59 III. + V. ratio 1:3 0.01 + 0.03 71 IV. + V. ratio 1:3 0.01 + 0.03 69 The results show that 0.04% (0.01 + 0.03) of the compositions containing three active ingredients has a better fungicidal ac-25 tion than 0.05% of the individual active ingredients and the two-component active ingredient composition. The same experiment, carried out with triazole-sensitive Erysiphe graminis, confirmed the results given in Table 1. 30 Table 2 Erysiphe graminis test (wheat) eradicative Triazole-resistant Erysiphe graminis 35 40 45 Active ingredient (a.i.) Active ingredient con Degree of action centration in the spray in % of the un liquor in % treated control Control (untreated) - 0 I. prior art a.i. 0.1 55 0.01 29 II. prior art a.i. 0.1 52 fenpropimorph 0.01 25 III. prior art a.i. 0.1 36 epoxiconazol 0.01 10 IV. prior art a.i. 0.1 29 prochloraz 0.01 5 V. prior art a.i. 0.1 83 a.i. I + fenpropimorph 0.01 55 0050/43931 12 26 3 1 Active ingredient (a.i.) Active ingredient concentration in the spray liquor in * Degree of action in % of the untreated control VI. prior art a.i. combination a.i. I + epoxiconazol 0.1 0.01 67 38 VII. prior art a.i. combination a.i. I + prochloraz 0.1 0.01 65 34 VIII. prior art a.i. combination fenpropimorph + prochloraz 0.1 0.01 55 38 IX. prior art a.i. composition fenpropimorph + epoxiconazol 0.1 0.01 60 42 Compositions according to the invention 20 degree of action observed degree of action calculated*) I. + VIII. 0.01 + 0.01 ratio 1:1 69 55.98 I. + VIII. 0.1 + 0.1-ratio 1:1 93 79.75 25 I. + VIII. 0.01 ratio 10:1 81 72.10 I. + VIII. 0.01+0.1 ratio 1:10 73 60.05 30 I. + IX. 0.01 + 0.01 ratio 1:1 71 58.85 I. + IX. 0.1 + 0.1 ratio 1:1 100 82.00 I. + IX. 0.1 + 0.01 ratio 10:1 88 73.90 35 I. + IX. 0.01 + 0.1 ratio 1:10 83 71.60 I. + VI. 0.01 + 0.01 ratio 1:1 64 53.50 40 I. + VI. 0.1+0.1 ratio 1:1 100 84.16 I. + VI. 0.1 + 0.01 ratio 10:1 86 70.24 I. + VI. 0.01 + 0.1 ratio 1:10 88 75.25 45 I. + VII. 0.01 + 0.01 ratio 1:1 62 50.50 *) calculated by the Colby formula </div>

Claims

<div class="application article clearfix printTableText" id="claims"> 0050/43931 26 3 1 7 13 degree of action observed degree of action calculated* ) I. + VII. 0.1 + 0.1 ratio 1:1 100 83.20 I. + VII. 0.1 + 0.01 ratio 10:1 83 68.32 I. + VII. 0.01 + 0.1 ratio 1:10 86 73.75 III. + V. 0.01 + 0.01 ratio 1:1 71 59.50 III. + V. 0.1 + 0.1 ratio 1:1 100 89.12 III. + V. 0.1 + 0.01 ratio 10:1 100 84.70 III. + V. 0.01 +0.1 ratio 1:10 86 71.20 IV. + V. 0.01 + 0.01 ratio 1:1 69 57.25 IV. + V. 0.1 + 0.1 ratio 1:1 100 87.93 IV. + V. 0.1 + 0.01 ratio 10:1 83 68.05 IV. + V. 0.01 + 0.1 ratio 1:10 98 83.85 In these results for various three-component active ingredient compositions, the observed degrees of action were always greater than the degrees of action calculated by the Colby formula. 30 The same experiment, carried out with triazole-resistant Erysiphe graminis, confirmed the results given in Table 2. 35 40 45 14 We claim: 263170

1. A fungicidal agent containing a fungicidally effective amount of a composition of a) methyl o -methoximino-2-[ (2-methylphenoxy) -methyl]-phenyl-acetate I -O 0— ch2 | ^,c=noch3 h3cooc " and b) 4-(2-methyl-3-[4-tert-butylphenyl]-propyl)-2,6-dimethyl-morpholine (fenpropimorph) - ch3 ch3 ych3 I _/=\_ I ^ ch3 c a ch2 ch ch2— n 0 I — ^ ( CH3 CH3 or the active ingredient tridemorph-or the active ingredient fenpropidin and c) an azole active ingredient selected from the following group N-propyl-N- [2- (2,4, 6-trichlorophenoxy) ethyl] imidazole-1-carboxamide 263170 IS (Z)—2—(1,2,4-triazol-l-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane of the formula 1-butyl-l-(2,4-dichlorophenyl)-2-(1,2,4-triazol-l-yl)-ethanol (common name hexaconazole), 1- (4-fluorophenyl) t1- (2-fluorophenyl) -2- (1,2,4-triazol-l-yl)-ethanol (common name flutriafol), (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-l-ylme-thyl)-butyronitrile, 1—[(2 RS, 4 RS; 2 RS, 4 SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofurfu-ryl]-1H-1,2,4-triazole, 3-(2,4-dichlorophenyl )-2-(1H-1,2,4-triazol-l-yl)-quinazolin-4(3H)-one, (RS)-2,2-dimethyl-3-(2-chlorobenzyl)-4- (1H-1,2,4-tria-zol-l-yl)-butan-3-ol, bitertanol, triadimefon, triadime-nol, cyproconazole, dichlobutrazol, difenoconazole, diniconazole, etaconazole, propiconazole, flusilazole, tebu-conazole, imazalil, penconazole, tetraconazole and a salt of such an azole active ingredient, wherein ccmpounds a), b) and c) are present in synergistic proportions A method of combating fungi, wherein a fungicidally effective amount of a composition of a) methyl a -methoximino-2- [ (2-methylphenoxy) -methyl] -phenyl-acetate x—-9 ^ =noch3 H3COOC and b) 4-(2-methy1-3-[4-tert-butylphenyl]-propyl)-2,6-dimethyl-morpholine (fenpropimorph) ch3 ch3 / l_y=\ I f—( ch3—- c—ft~~~ ch2~" ch— ch2— n c I ^ ( ch3 x 3n.z. patient o.-.: re ! 2 2 FEB 1996 RECEIVLU ch3 16 263170 or the active ingredient tridamorph or the active ingredient fenpropidin c) an azole active ingredient selected from the following group N-propyl-N- [2- (2,4, 6-trichlorophenoxy) ethyl] imidazole-1-carboxamide (Z)-2-(1,2,4-triazol-l-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane of the formula 1-butyl-l-(2,4-dichlorophenyl)-2-(1,2,4-triazol-l-yl)- ethanol (common name hexaconazole), 1- (4-f luorophenyl) rl- (2-f luorophenyl) -2- (1,2,4-triazol-l-yl)-ethanol (common name flutriafol), (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-l-ylmethyl) -butyronitrile, 1-[(2 RS, 4 RS; 2 RS, 4 SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofurfu-ryl]-1H-1,2,4-triazole, 3-(2,4-dichlorophenyl )-2-(1H-1,2,4-triazol-l-yl)-quinazolin-4(3H)-one, (RS)-2,2-dimethy1-3-(2-chlorobenzy 1)-4- (1H-1,2,4-triazol-l-yl) -but an-3-ol, bitertanol, triadimefon, triadime-nol, cyproconazole, dichlobutrazol, difenoconazole, diniconazole, etaconazole, propiconazole, flusilazole, tebu- and 2

2 FEB 1996 RECEIVED 263170 17 conazole, imazalil, penconazole, tetraconazole and a salt of such an azole active ingredient, wherein compounds a), b), and c) are in synergistic proportions, is allowed to act on the fungi or the materials, areas, plants or seed threatened by fungus attack.

3. A fungicidal agent as claimed in claim 1, containing ccnpounds a), b) and c) in a weight ratio of a:b:c of from 10 to 1:10 to 1:10 to 1.

4. A fungicidal agent of claim 1 or claim 3 substantially as herein described with reference to the Example.

5. A method for combating fungi according to claim 2 substantially as herein described. 2 2 FEB 1996 RECEIVED </div>