DE3102590A1 - Microbicides - Google Patents

Abstract

The novel compounds of the formula I <IMAGE> defined herein are potent microbicides. They can be used by themselves or in the form of compositions, in particular for controlling phytopathogenic fungi and bacteria.

Description

Microbicidal agents

The present invention relates to compounds of the formula I. wherein R1, R2, R3 and R4 independently of one another are hydrogen, halogen. C1-C4 alkyl. C1-C8-alkoxy optionally substituted by halogen or C1-C4-alkoxy, optionally substituted by halogen C3-C6 alkenyloxy, or benzyloxy or phenoxy optionally substituted by halogen, cyano, C1-C4-alkyl or C 1-C4-alkoxy , for CH or N or and m is 0 or 1, while R5 is hydrogen, C1-C3-alkyl or phenyl, R6 is optionally substituted by halogen, C1-C4-alkoxy or phenyl, C1-C6-alkyl or optionally by halogen-substituted C3-C6-alkenyl, C3-C6 -Alkynyl or C3-C6 cycloalkyl and R7 denotes hydrogen or methyl, processes for the preparation of these compounds and agents and use for combating microorganisms.

Under alkyl or as an alkyl part of an alkoxy group are depending on the number the specified carbon atom to understand the following groups: methyl, ethyl, Propyl, butyl, pentyl hexyl, heptyl or octyl and their isomers, e.g.

iso-propyl, iso-, sec- or tert-butyl, l-methylbutyl, etc.

The following groups are to be understood by alkenyl: propenyl, allyl, Methallyl, butenyl, 4-pentenyl or hexenyl.

The term halogen includes fluorine, chlorine, bromine or iodine.

As cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl and Meant cyclohexyl.

The most common C3-C6-alkynyl are prop-2-ynyl (propargyl) and but-2-ynyl mentioned.

The compounds of the formula I can be prepared according to the invention by a) a compound of the formula II with a compound of the formula III acylated or b) a compound of the formula IV with a compound of the formula V. reacted, where in the formulas II to V R1, R2, R3, R4, X and Y have the meanings given for formula t, while Hal is halogen, preferably chlorine or bromine, and W is hydrogen or a metal atom, preferably sodium or potassium represents.

The reactions can take place in the presence or absence of the reactants inert solvents or diluents. For example, there are the following in question: aliphatic or aromatic hydrocarbons such as benzene, Toluene, xylenes, petroleum ether; halogenated hydrocarbons such as chlorobenzene, methylene chloride, Ethylene chloride, chloroform; Ethers and ethereal compounds such as dialkyl ethers, Dioxane, tetrahydrofuran; Nitriles like Acetonitrile; N, N-dialkylated Amides such as dimethylformamide; Dimethyl sulfoxide, ketones such as methyl ethyl ketone and mixtures such solvents among themselves.

The reaction temperatures are between -200 and 1600 ° C., preferably between -100 and 1200. In the reactions, the use of acid-binding Means or

Condensing agents advantageous. Tertiary amines come as such such as trialkylamines (e.g. triethylamine), pyridine and pyridine bases, or inorganic ones Bases such as the oxides, hydroxides and hydrides, hydrogen carbotates and carbonates of Alkali and alkaline earth metals as well as sodium acetate into consideration. As an acid-binding In addition, in the first process a) an excess of the respective aniline derivative can be used of formula II or in process b) (if W is hydrogen) an excess on the compound of formula V serve. The connection V can only then serve as an acid-binding agent if it has sufficient basicity.

Details on the preparation of the precursors of the formula II can be found in the methods as generally given for the preparation of anilino-alkanoic acid esters in the following publications: J.Org. Chem. 30, 4101 (1965), Tetrahedron 1967, 487, The compounds of the formula I have a center of asymmetry in group X (adjacent to the anilide nitrogen) (exception R5-H) and can be used in the usual way (eg use of already separated Starting materials) as optical antipodes. The two configurations of such a compound of the formula I have different levels of microbicidal activity. The influence of other possible centers of asymmetry in the molecule and the atropisomerism around the phenyl Ach8e have little influence on the microbicidal effectiveness of the entire molecule. If no specific synthesis is carried out to isolate pure isomers of the formula I or the precursors used, a product is normally obtained as a mixture of isomers.

The compounds of formula 1 indicate a practical requirement very favorable microbicide spectrum for the protection of crops. Crops Set within the scope of the present invention, for example, cereals, maize, rice, vegetables, Sugar beet, soy, peanuts, fruit trees, ornamental plants, but above all vines, hops, Cucumber plants (cucumbers, pumpkins, melons), Solanaceae such as potatoes, tobacco and tomatoes, as well as avocado, banana, cocoa and natural rubber plants. With the active ingredients of formula I can be applied to plants or parts of plants (fruits, flowers, foliage, Stems, tubers, roots) of these and related crops, the fungi that occur be contained or destroyed, with later overgrown parts of plants of such mushrooms are spared. The active ingredients are against the following Classes of phytopathogenic fungi Xsam: Ascomycetes (e.g., Erysiphaceae as well as Fusarium spp.) Basidiomycetes such as especially rust fungi (e.g. Puccinia); Fungi imperfecti (e.g. Moniliales and others Cercospora and Piricularia); then against the Class of the Oomycetes belonging to Peronosporales such as Phytophthora, Pythium or Plasmopara. They also know as a dressing agent for the treatment of seeds (fruits, Tubers, Kerner) and plant cuttings to protect against fungal infections and against Phytopathogenic fungi occurring in the soil are used will.

Interesting compounds of the formula I are, for example, those in which R1 is 2-methyl, R2 is hydrogen or methyl, R3 is hydrogen and R4 is hydrogen, 4-C3-C8-alkoxy or represent 4-methyl.

Those compounds are preferred in which R2 is hydrogen and R4 4-C3-C8 branched alkoxy e.g.

mean s-butoxy or 4-methyl.

Also of interest are compounds of the formula I in which R1 and R4 are halogen and R2 and R3 are hydrogen.

R1 and R2 are preferably each in the ortho position to the Nitrogen.

Within the abovementioned groups, compounds are preferred in which X is stands.

Y = CH- is preferred, combinations of these preferred compound groups are also to be regarded as preferred.

The following should be mentioned as a preferred individual compound: N- (1-methoxycarbonyl -ethyl) -N- (imidazolcarbamoyl) -2-methyl-4-sec-butoxy-aniline.

The compounds of the formula I are known alone or together be used with suitable supports and / or other aggregates. Suitable Carriers and aggregates can be solid or liquid and correspond to those in the Formulation technology common substances such as

natural or regenerated mineral substances, Ventilation, Dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. The production such agents are carried out in a manner known per se by intimate mixing and grinding of the components. For application, the compounds of the formula I can be used in the following Forms of work-up are available (the percentages by weight being advantageous amounts of active ingredient).

Solid forms of processing: dust, grit, (up to 10) grains, Granules, coated granules, impregnation granules and homogeneous granules; Pellets (kernel) (1 to 80%) liquid preparation forms: a) dispersible in water Active ingredient concentrates: wettable powders (wettab le powders) pastes, 25-90 7. in the retail pack, 0.01 to 15% in ready-to-use solution, emulsions; Solution concentrates (10 to 50%; 0.01 to 15 7. in ready-to-use solution) b) Solutions: Aerosols: The content the active ingredient in the agents described above is between 0.1 and 95 percent by weight.

The compounds of formula I can adapt to them under the given circumstances adapt, of course to broaden their range of effects with others suitable pesticides, such as fungicides, bactericides, insecticides, acaricides, Herbicides or active ingredients influencing plant growth are used together will.

The following examples serve to explain the invention in more detail, without restricting the same. The temperature data relate to degrees Celsius. Unless otherwise noted, an active ingredient is named using the formula I always meant the racemic mixture of possible isomers.

Preparation examples Preparation of N- (1'-methoxycarbonylethyl) -N- (imidazolcarbamoyl) -2-methyl-4-sec-butoxy-aniline of the formula I. (Comp. No. 55) 550 g (1.68 mol) of N- (1'-methoxycarbonyl-ethyl) -N-2-methyl-4-sec-butoxy-aniline-carbamoyl chloride were dissolved in 500 ml of tetrahydrofuran at room temperature and added dropwise to the sodium salt of imidazole suspended in the 3000 ml of tetrahydrofuran. This sodium salt was prepared under a nitrogen atmosphere by adding dropwise a solution of 143 g (2.1 mol) of imidazole in 2000 ml of tetrahydrofuran to a suspension of 82.5 g (1.9 mol) of 55% sodium hydride dispersion in oil in 1000 ml of tetrahydrofuran. The reaction mixture was stirred at room temperature for 24 hours, filtered and concentrated under reduced pressure. The oily residue was then dissolved in ether and washed with water. The ether solution was dried over sodium sulfate, filtered and evaporated.

After separating off the paraffin oil in a separating funnel, 452 is obtained g product of nD5 1.5295.

In this way or by one of the methods described herein e.g. the following compounds of formula I can be prepared.

Table I. Y = N) II No. 2 R2 R3 R4 5 6 Pbysical. Verb. 11 RRKRR constant 1 2-CH3 6-CH3 HH CH3 CH3 m.p. 98-99 ° 2 2-CH3 6 -CH, 4-CR3 II CH3 CH3 m.p. 152-1580 3 2-CH3 6-C2115 II H CH3 CH3 m.p. 82-850 4 2-i-C3117 6-i-C3117 HH CH3 CH3 nD .5 1.5041 5 2-i-C3H7 6 4 C3H7 4-Br ii CH3 CH3 n 4'5 1.4311 nD 6 2-CR3 4-0C4E9 (s HH CH3 CH3 m.p. 61-65 ° 7 2Ca3 4-OC2H40CX 3 HH CH3 CH3 32, Ii 1.5224 8 2-CH3 4-OCH2C'CH2 HH CR3 CH3 m.p. 70-74 LI IL 9 2 -CF, 4 -OH, 2-013 H CH3 CH3 CH3 34 4-oCR2CaflC? CR3H H CR3 013 nD 1.5450 C1 10 2 -CH3 4-OCH2 t HH CH3 CH3 m.p. 90-920 11 2-CH3 4-OCHZCCH HH CH3 CH3 n 9 1.4819 C1 C1 12 2-CH3 4-OCH2CH "CHC1.HH Ca3 CH3 Oil 13 2 -CH3 4-OC4H9 (s) 6-CH, CH3 14 2-CH3 4-OC3H7 (i) HH CH3 CH3 m.p. 93-950 15 2-CH3 4-OC5HII (n) HH CH3 CH3 m.p. 68-730 16 2-013 4-OC8H17 (n) HH CH3 CR3 Conn. R1 R2 R3 R4 R5 R6 Physical. No constant 17 2-CH3 4 4cm2 4-0Ca2 3 HH CH3 CH3 18 2-CH3 4-0CR2βCOil HH CH3 CH3 C1 19 2-CH3 4-OCH3- @ C: H5 HH CH3 CH3 20 2-C1 4-C1 HH CH3 CH3 oil 21 2-CH3 4-OCH2 4 HH CH3 CH3 m.p. 89-92 ° 22 2-CH3 4-CH3 HH CH3 CH3 21 1.5342 nD 23 HHHH CH3 CH3 oil 24 2-CF3 HHH CH3 CH3 25 3-CF3 5-CF3 HH Ca3 Ca3 26 2-013 4-0 - HH CH3 CH3 27 2-OCE 4-0-QO to HH CH3 CH3 Oel 28 H 4-0Cl to C1 HH CH3 CR3 29 H 4-0 + C1 HH CH3 CH3 C1 30 H 4 0 4-0Ca3 CH3 HH CH3 CH3 31 2-CH3 4-0- zuH HR CH3 CH3 Oel 32 2-CH3 4-0 -C4H9 (s) HH C2H5 CH3 33 2-CH3 3-CH3 5-C! 6-CHJ CH3 34 2-CH3 4-OC4H9 (s) HH C6H5 CH3 m.p. 98-100 ° C 35 2-C1 4-C1 HH C6H5 CH3 36 2-CH3 4-OC4Hg (s) HH CH3 C2H5 37 2-CH3 4 -OC4H9 (S) HH CH3 CH2CH20CH3 38 2-013 4-OC4H9 (s) HH Ca3 Ca2-QO Conn. R1 R2 R3 R4 R5 6 Physical. No constant 39 2-C1 4-Cl II II 013 - 40 2-CH3 4-C1 HH CH3 C) L -C4tCH-CH2 41 2-CH3 4-OC4H9 (8) HH CH3 -CC ^ CH 42 H 4-0-QO HH CH3 -Ca2 i) 43 2-Cl 4-Cl H ii CH3 -C3H7 (i) 44 2-CH3 4-OC4H9 (8) HHH -C2H5 45 2-C1 4-C1 HHH -CH3 46 II 4-0 HH C6H5 3W n 1.5580 47 2 <13 4-CH3 II H C6H5 C3H7 (i) m.p. 117 1190 48 2-C1 4-C1 HH C6H5 C3H7 (i) m.p. 38-390 49 2-CH3 4-0C4119 (s) HH C6R5 C3H7 (i) Table II Conn. R1 RRRRR Physical. No. 1 2 3 4 5 6 constant 50 2-CH3 6-ClI3 HH CH3 CH3 m.p. 118-1220 51 2-CH3 4-CH3 6-CES H CH3 CH3 m.p. 120-1240 52 2-CH3 6-C2H5 HH CH3 CH3 m.p. 67-680 53 2-CsH7 (i) 6-C3H7 (i) HH CH3 CH3 m.p. 123-126 54 2 nH7 (i) 6-C3H7 (i) 4-Br H CH3 CH3 m.p. 25th 55 2-013 4-OC4H9 (ß) HH cH3 CH3 n25 1.5295 56 2-CH3 4-OC2H40CH3 HH CH3 CH3 nD2C5 1.5180 57 2 -CH3 4-oCH2CtCH2 HH CH3 CH3 n32X5 1.5373 013 Conn. R1 R2 R3 R4 R5 R6 Physical. Wr ~ ~ constant 58 2-CH3 4-oCH2CH'CCH lI H CH3 CH3 nD9 1.5382 59 2-CH3 4-OCH22 II U 013 CH3 42s5 1.554 60 2-CH3 $ -OCH, C C1 C1 HH CH3 CH3 0.1 Cl Cl 61 2-CH3 4-0CR2Ca-01C HH CH3 CH3 Oil 62 2-013 4-OC4Hg (8) 6.% H CH3 CH3 63 2-CA3 4-OC3H7 (i) HH CH3 CH3 m.p. 65-680 64 2-CH3 4-OC5HII (n) HH CH3 CH3 oil 65 2-C1 4-C1 HH CH3 CE3 Oel 66 2-CH3 4-OCH26 RH CH3 CH3 oil 67 2-CH3 443 HH CH3 CH3 21 1.5397 68 HHHH CH3 CH3 oil 69 2-CF3 HHH CH3 CH3 70 3-CF3 1 5-CF3 HH CH3 CR3 71 2-CH3 4-0-Qo RH CH3 CH3 72 H 4 «0 -6> cl HH CH3 CH3 73 H 4-0Cf KH CH3 CH3 Cl 74 2-OCH3 4-0 HH CH3 CH3 oil 75 2-OCH3 4-0 - HH CH3 CH3 oil 76 2-CH3 4-OC4H, (s) HH C2H5 C1I3 Verb. RRR To R5 Physical. No. | 5 6 constant 77 2-CH3 3-CH3 5- 6- CH3 13 CH3 21 78 2-CH3 4 «OC4H9 (s) HH C6115 CH3 nD 1.5566 79 2-C1 4-C1 HH C6R5 CH3 80 2-CH3 4-OC4H9 (s) RH CH3 C2E5 81 2-013 4-0C4R9 (s) HH CH3 C3H7 (t) 82 2-013 4-0C4H9 (s) HH CH3 -CH2CHCH3 83 2 413 4-0C4U9 (s) HH CH3 42 -0120 84 2-Cl 4-C1 HH CH3 f 85 2-CH3 4-C1 HH CH3 -CZCHICH2 86 2-CH3 4-0C4H9 (β) HH CH3 -CH2CCH 87 H 4-OKH CH3 -CH24) 88 2-C1 4-C1 HH CH3 -C3H7 (i) 89 2-CH3 4-OC4Hg (s) II H II -C2H5 90 2-C1 4-C1 HHH CH3 91 H 4 «0- @ HRH CH3 92 2-CH3 4-0C4119 (s) HH C3II7 (0 CH3 93 H 4-0 HH C6H5 C3H7 (i) n231.5670 94 2-CH3 4-OC4H9 (s) HH C6115 C3H7 (i) 95 H4-C4Hg (t) HH CH3 CH3 96 H 4 -C 4 H 9 (t) H H C 6 H 5 CH 3 97 H4-C4H9 (t) HH CH3 C2H5 98 H 4 -C 4 Hg (t) HHH C2H5 99 2-C3H7 (i) 6-C3H7 (ff) HHH CH3 100 2-C3H7 (i) 6-C3H7 (i) HHI: H3 -C3H7 (i) 101 2-C3H7 (L) 6-C3H7 (i) HHH -CH2 w 102 2-CH3 6 43 4-C1 H CH3 CH3 103 2-CH3 4-CH3 HH C6H5 C3H7 (i) Z ID 1.5490 104 2-C1 4-C1 ~ H C6H5 C3H7 (i) m.p.> 50 ° Table III - - - Verb J 4 R6 No . 105 2 -CE3 6-OC, H, (s) EI HH Cti3 106 2-013 4-oC4H9 (s) H II H C2115 107 2-013 44C4H9 (8) HH CE3 CH3 108 2-CH3 4z0C4Hg (s) HH CH3-012OO 109 2-C1 4 «C1 HHH C2H5 110 2C1 4-C1 HH 013 CH3 111 H 444 HHH C2H5 112 2-CH3 4-CH3 HHH CB nD ° l 5295 113 2 «cm3 4-OCt5- HH 114 2 EI3 4 "0C3H7 (i) HH CH3 CE3 115 2-013 4-C1 6-013 H Ii C2H5 116 HHHRH C2H5 Table IV Connection R1 R2 R3 R4 R5 I R6 No. 117 2-CH3 4-oc4Hg (s) HHH CH3 118 2-CH3 4-OC4H9 (s) HHH C2H5 119 2-CH3 4-0C4H9 (s) HH CH3 CH3 120 2-CH3 4-OC4H9 (s) HH 013 121 2-C1 4-C1 HHH C2115 122 2-C1 4-C1 HH CH3 CH3 Conn. To R1 - R2 R3 R4 R5 R6 No. 123 H 4-0- @ II II H C2R5 124 2-CH3 4-CH3 HHH C2H5 nD11,5415 125 r 2-Cli3 4-OCH2- @ HHH C2115 126 i 2013 4-oC3H7ti) II II 013 Ca3 127 2 <13 4-C1 6-CH3 HH C2H5 128 HHHHH C2R5 129 2-CH3 4-C1 RHH C5 130 2 - (: H3 4-0-C1 HH CH3 CH3 131 2-013 4-0Ca2cPO HHH C2H5 C. 132 H 4-0Ct Cl HHH C2R3 Table V Conn. R1 R2 R3 R7 Y Physical. No. (s) HHN constant 133 2-CH3 4-oc4H9 (s) HHN m.p. 160-1620C 134 2 <13 4zOC4H9 (S) HH CH m.p. 134-136 ° 135 2-CH3 6-CH3 HHN m.p. 148-154 ° 136 2-CH3 6-CH3 HH CH m.p. 146-1500 137 2-CH3 3-ca3 6-CEE HN m.p. 160-168 ° 138 2 <13 3-CH3 6-CH3 H CH m.p.121 -1290 139 2-C1 4-C1 HHN 140 2-C1 4-Cl HH Approx 141 U 4-0iS II HHN Connection R1 R, No. L42 | H 44 4-0CF3 II ä approx 143 2-CH3 4-0-CH2-i> HUN 144 2 -CH3 4-0CR2 HH Approx 145 2-CH3 4-0Ca2CaCR2 HHN 146 2-CE3 4Z0CH2CH-CH2 HH Approx 147 2 -CH3 4-0C3H7 (r> u HN 148 2013 4-0C3117 (i) HH Approx 149 HHHHN 150 R II H II CH 151 H4-C4H9 (t) II HN 152 H 4 <4H9 (t) H II Approx 153 2-CH3 4 "0C4Hg (8) Ii CH3 N L54 2 T13 4-0C4E9 (s) H CH3 -01 155 2-C1 4-C1 H CH3 N 156 2-C1 4-Ci H CH 3 CH 157 H 4-0-Qo H CH 3 N 158 H 44 RH M3 approx Biological B-iswiele Example 2 Action against Erysiphe graminis on barley a) Residual-nrotective action Barley plants about 8 cm high were sprayed with a spray mixture prepared from a wettable powder of the active ingredient (0.02% active ingredient). After 4 hours, the treated plants were dusted with conidia of the fungus.

The infected barley plants were grown in a greenhouse at approx. 22 ° C and assessed the fungal attack after 10 days.

b) Systemic effect On barley plants approx. 8 cm high, a Spray booth made from wettable powder of the active ingredient poured (0.006 Z active ingredient based on the earth's volume). Care was taken that the spray mixture did not came into contact with the above-ground parts of the plant. After 48 hours the treated plants are pollinated with conidia of the fungus. The infected barley plants were placed in a greenhouse at about 220 C, and the fungal attack was assessed after 10 days.

Example 3 Effect of Puccinia graminis genes on wheat a) Residual-protective Effect Wheat plants were made 6 days after sowing with a wettable powder of the active ingredient prepared spray mixture (0.06% active ingredient) sprinkled. To The treated plants were wounded with a uredospore suspension of the fungus for 24 hours infected. After incubation for 48 hours at 95-100 Z relative humidity and about 200 C, the infected plants were in a greenhouse at about 22 ° C set up.

The assessment of the rust pustule development took place 12 days after the Infection.

b) Systemic action Wheat plants became 5 days after sowing a spray mixture made from wettable powder of the active ingredient is poured (0.006% Active substance based on the soil volume). After 3 days they became hairy Plants infected with a uredospore suspension of the fungus. After an incubation for 48 hours at 95-100% relative humidity and approx. 200 ° C. the infected plants are placed in a greenhouse at about 220.degree.

The rust pustule development was assessed 12 days later the infection.

Example 4 Action against Cercospora arachidicola on peanut plants 3-week-old peanut plants were prepared from a wettable powder formulation of the active ingredient Spray liquid (0, O2 7.

Active substance) sprayed, after about 12 days, the treated Plants dusted with a conidia suspension of the fungus. The infected plants were then incubated for about 24 hours at 90% relative humidity and then placed in the greenhouse at approx. 220 ° C.

The fungal attack was evaluated after 12 days.

Example 5 Effect of times Phytophthora infestans on tomatoes a) Curatives Effect tomato plants of the variety "Roter Genom" were grown after three weeks sprayed with a zoospore suspension of the fungus and in a booth at 18 to Incubated 20 ° and saturated humidity. Interruption of humidification after 24 hours. After drying the plants, they were sprayed with a broth, the active substance formulated as a wettable powder in a concentration of 0.06 % contains. After the spray coating had dried on, the plants were again in the Damp cabin set up for 4 days. Number and size of the after this time The typical leaf spots that occurred were the benchmark for the effectiveness of the tested substances.

b) Systemic protective effect The one formulated as a wettable powder Active substance was found in a concentration of 0.006 7. (based on the soil volume) on the soil surface of three-week-old potted tomato plants of the variety "Red Gnome" given.

After a three-day waiting period, the underside of the foliage became with sprayed a zoospore suspension of Phytophthora infestans. They were then 5 Maintained for days in a spray booth at 18 to 200 and saturated humidity. After this time, typical leaf spots formed their number and size were used to evaluate the effectiveness of the substances tested.

Example 6 Action against Piricularia orozae on rice a) Residual protective Effect After two weeks of cultivation, rice plants were made from wettable powder of the active ingredient prepared spray mixture (0.02% active ingredient) sprayed. After 48 The treated plants were treated with a conidia suspension of the fungus for hours infected. After 5 days of incubation at 95-100 7. relative humidity and The fungal attack was assessed at 240 C.

b) Systemic action One of two rice plants was used for two-leaf rice plants Wettable powder of the active ingredient, poured spray mixture (0.006: active ingredient based on the earth's volume). The bowls were then filled with water to the extent that that the lowest parts of the stalk of the rice plants were in the water.

After 48 hours, the treated rice plants were sprinkled with a conidia suspension infected by the fungus. After incubation of the infected plants for 5 days The fungal attack was assessed at 95-100% relative humidity and approx. 24 ° C.

Example 7 Action against Fusarium nivale wheat grains were with a Spore suspension of the fungus contaminated and dried again. The contaminated Granules were mixed with a suspension of the test substance made from wettable powder pickled (600 ppm active ingredient based on the weight of the seeds).

After two days, the grains were laid out on suitable agar dishes and after another four days the fungal colonies began to develop around the grains judged around. The number and size of the fungal colonies were used to assess the test products used.

The following compounds showed an inhibition of the in the following fungi Infestation to less than 10% compared to control plants.

at Erysiphe graminis. Compounds No. 1, 6, 12, 14, 21, 22, 50, 51, 53, 55, 59, 61, 63, 64, 65, 66, 105 and 68.

in Puccinia graminis. Compounds No. 1, 2, 52, 53 and 135.

in Cercospora arachidicola. Compounds No. 6, 12, 21, 52, 55, 57, 61, 63, 64, 66, 68 and 135.

in Phytophthora infestans. Compound No. 1, 22, 52, 135, 136 and 137.

in Piricularia oryzae. Compound No. 6 at Fusarium nivale. link No. 52 and 58.

Formulation Examples Example 8 Dusts: For the production of a a) 5 Zigen and b) 2% dust, the following substances are used: a) 5 parts of active ingredient, 95 parts of talc; b) 2 parts of active ingredient, 1 part of highly dispersed silica, 97 parts of talc; The active ingredients are mixed and ground with the carrier substances and can be dusted in this form for use.

Example 9 Granules: To produce 5% granules, the following substances are used: 5 parts of active ingredient, 0.25 parts of epoxidized vegetable oil, 0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (grain size 0.3-0.8 mm).

The active ingredient is mixed with epoxidized vegetable oil and with 6 parts of acetone dissolved, then polyethylene glycol and cetyl polyglycol ether added. The solution obtained in this way is sprayed onto kaolin, and then acetone is evaporated in vacuo. Such microgranules are advantageous for Used to control soil fungi.

Example 10 wettable powder: for producing a) 70% b) 40 Zigen c) and d) 25% e) 10 Zigen wettable powder are the following ingredients used: a) 70 parts of active ingredient, 5 parts of sodium dibutylnaphthylsulfonate, 3 parts Naphthalenesulfonic acids-phenolsulfonic acids-formaldehyde condensate 3: 2: 1, 10 parts Kaolin, 12 parts champagne chalk; b) 40 parts of active ingredient, 5 parts of sodium lignin sulfonic acid, 1 part of dibutylnaphtahlinsulfonic acid sodium salt, 54 parts of silica; c) 25 parts Active ingredient, 4.5 parts of calcium lignosulfonate, 1.9 parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1), 1.5 parts of sodium dibutyl naphthalene sulfonate, 19.5 parts of silica, 19.5 Parts of champagne chalk, 28.1 parts of kaolin; d) 25 parts of active ingredient, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1), 8.3 parts of sodium aluminum silicate, 16.5 parts of kieselguhr, 46 parts of kaolin; e) 10 parts of active ingredient, 3 Parts mixture of the sodium salts of saturated fatty alcohol sulfates, 5 parts naphthalenesulfonic acid / formaldehyde condensate, 82 parts of kaolin; The active ingredients are mixed with the additives in suitable mixers intimately mixed and ground on appropriate mills and rollers. Spray powder is obtained of excellent wettability and suspension, which turns into suspensions with water dilute to the desired concentration and use especially for foliar application permit.

Example 11 Emulsifiable Concentrate: To Make a 25 Zigen emulsifiable concentrate, the following substances are used: 25 parts of active ingredient, 2.5 parts of epoxidized vegetable oil, 10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture, 5 parts of dimethylformamide, 57.5 parts of xylene.

From such concentrates you know emulsions by diluting with water the desired application concentration can be produced 'which is particularly suitable for foliar application are suitable.

Claims (23)

Claims: 1. Compounds of the formula wherein R1, R2, R3 and R4 independently of one another are hydrogen, halogen, C1-C4-alkyl, C1-C8-alkoxy optionally substituted by halogen or C1-C4-alkoxy, C3-C6-alkenyloxy optionally substituted by halogen, or optionally by halogen , Cyano, C1-C4-alkyl or C1-C4-alkoxy-substituted benzyloxy or phenoxy, mean, Y for CH or N, or and m is 0 or 1, while R5 is hydrogen, C1-C3-alkyl or phenyl, R6 is optionally substituted by halogen, C1-C4-alkoxy or phenyl, C1-C6-alkyl or optionally by halogen-substituted C3-C6-alkenyl, C3- C6-alkynyl or C3 -C6 cycloalkyl and R denotes hydrogen or methyl. 7 2. Compounds of formula I according to claim 1, characterized in that that R1 is 2-methyl, R2 is hydrogen or methyl, R3 is hydrogen and R4 is hydrogen, Represent 4-C3-C8-alkoxy or 4-methyl. 3. Compounds of the formula I according to claim 2, characterized in that that R2 is hydrogen and R4 is branched 4-C3-C8-alkoxy, e.g. s-butoxy or 4-methyl mean. 4. Compounds of the formula I according to claim 1, characterized in that that R1 and R4 are halogen and R2 and R3 are hydrogen and R1 and R2 are each other are in the ortho position to the nitrogen. 5. Compounds of formula I according to any one of claims 1 to 4, characterized in that X stands for -CH (CH3> COO-CH3. 6. Compounds of formula I according to one of claims 1 to 5, characterized in that Y stands for = CH-. 7. The compound N- (l'-methoxycarbonyl-ethyl) -N- (imidazolcarbamoyl) -2-methyl-4-sec.butoxy-aniline, according to claim 1. 8. Process for the preparation of compounds according to Claim 1, characterized in that a) a compound of the formula II with a compound of the formula III acylated or b) a compound of the formula IV with a compound of the formula V. reacted, where in the formulas II to V R1, R2, R3, R4, X and Y have the meanings given for formula I, while Hal is halogen, preferably chlorine or bromine, and W is hydrogen or a metal atom, preferably sodium or potassium represents. 9. Microbicidal agent, characterized in that it is in addition to carriers and / or other additives as active ingredients according to at least one compound Claim 1 contains. 10. A microbicidal agent according to claim 9, characterized in that that it contains a compound according to claim 2 as active ingredient. 11. A microbicidal agent according to claim 9, characterized in that that it contains a compound according to claim 3 as active ingredient. 12. A microbicidal agent according to claim 9, characterized in that that it contains a compound according to claim 4 as active ingredient. 13. Microbicidal agent according to claim 9, characterized in that that it contains a compound according to claim 5 as the substance. 14. A microbicidal agent according to claim 9, characterized in that that it contains a compound according to claim 6 as active ingredient. 15. Microbicidal agent according to claim 9, characterized in that that it contains the compound according to claim 7 as active ingredient. 16. Use of a compound according to claim 1 for combating Microorganisms. 17. Use according to claim 16 of a compound according to claim 2. 18. Use according to claim 16 of a compound according to claim 3. 19. Use according to claim 16 of a compound according to claim 4th 20. Use according to claim 16 of a compound according to claim 5. 21. Use according to claim 16 of a compound according to claim 6th 22. Use according to claim 16 of the compound according to claim 7. 23. Use according to claim 16 for combating phytopathogens Mushrooms.