CH653675A5 - Microbicides - Google Patents

Abstract

Novel compounds of the formula I are described <IMAGE> in which A denotes oxygen, sulphur, -CH2-, -CH2CH2- or -CH=CH- and the remaining substituents have the meanings given in Claim 1. Such compounds can be used for controlling microorganisms, in particular against phytopathogenic fungi and bacteria. Compounds of the formula I have a curative, preventive and systemic activity for the protection of crop plants which is highly favourable for practical requirements, without affecting the crop plants by undesired side effects. They can in practice be used by themselves or in the form of compositions.

Description

       

  
 

** WARNING ** beginning of DESC field could overlap end of CLMS **.

 



   PATENT CLAIMS 1. Compounds of Formula I
EMI1.1
 wherein R is a C1-C6-alkyl or C3-C7-cycloalkyl which is optionally substituted by halogen or Cl-C3-alkoxy; a C2-C5-alkenyl optionally substituted by halogen or methyl; C3-C5 alkynyl; a 2-furyl optionally substituted by halogen, methyl or methoxy; or a phenyl optionally substituted by halogen, cyano, C1-C3-alkyl, C1-C3 alkoxy, trifluoromethyl or nitro; n is 0 or 1, X and Y are independently oxygen or sulfur, A is oxygen, sulfur, -CH2-, -CH2CH2- or -CH = CH- and R1 and R2 are independently hydrogen, halogen, methoxy or trifluoromethyl stand.



   2. Compounds of formula I, according to claim 1, wherein A is -CH2-CH2-.



   3. Compounds of the formula according to claim 1, wherein A is -CH = CH-.



   4. Compounds of formula I, according to claim 1, wherein A is sulfur.



   5. Compounds according to any one of claims 1 to 4, wherein R1 = H, F or Cl, R2 = H and X are oxygen.



   6. A process for the preparation of compounds of the formula I according to claim 1, characterized by reaction of a compound of the formula II
EMI1.2
 with a compound of formula III R'-Z (III) where R 'is -COR or -COXR, A, X, R1, R2 and R have the meanings given for formula I and Z is a N-acylation. (Thio) carbamoylation is a reactive leaving group.



   7. Means for combating and / or preventing microorganism infestation, characterized in that it contains, as at least one active ingredient, a compound of the formula I according to claim 1, together with one or more suitable carrier materials and / or distribution agents.



   8. Use of compounds of formula I according to claim 1 for combating microorganisms.



   9. Use according to claim 8, characterized in that it is phytopathogenic microorganisms.



   The present invention relates to compounds of the formula
EMI1.3
 wherein R is a C1-C6-alkyl or C3-C7-cycloalkyl optionally substituted by halogen or C-C3-alkoxy; a C2 C5 alkenyl optionally substituted by halogen or methyl; C3-C5 alkynyl; a 2-furyl optionally substituted by halogen, methyl or methoxy; or a phenyl optionally substituted by halogen, cyano, CI-C3-alkyl, C-C3-alkoxy, trifluoromethyl or nitro; n is 0 or 1, X and Y are independently oxygen or sulfur, A is oxygen, sulfur, -CH2-, -CH2CH2- or -CH = CH- and R1 and R2 are independently hydrogen, halogen, methoxy or trifluoromethyl stand.



   Depending on the number of C atoms specified, alkyl or alkyl moiety of another substituent means, for example, the following groups: methyl, ethyl, propyl, butyl, pentyl or hexyl and their isomers, such as Isopropyl, isobutyl, tert-butyl, isopentyl, etc. alkenyl stands for an unsaturated, aliphatic radical with one or more C = C double bonds, consisting of a maximum of 7 carbon atoms; for example for vinyl, propenyl- (l), allyl, butenyl- (l), butenyl- (2), butenyl- (3), etc. or CH3-CH = CHCH = CH-etc. Cycloalkyl is understood to mean, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Depending on the number of carbon atoms, alkynyl means the following groups:
Propynyl (1), propargyl, butynyl (1), butynyl (2), etc.

  Here and below, halogen represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.



   Compounds of formula I show a very valuable microbicide spectrum. They can e.g. against phytopathogenic microorganisms, especially against plant-damaging fungi and bacteria.



   A preferred group of microbicides consists of compounds of the formula I in which R represents a C2-C4-alkyl group which is optionally substituted by halogen and n denotes 0 or 1.



   Another preferred group of microbicides consists of compounds of the formula I in which R is C3-C4 cycloalkyl, in particular cyclopropyl and n is 0 or 1.



   A further preferred group of microbicides form compounds of the formula I in which R represents a C2-C5-alkenyl radical which is optionally substituted by halogen and n represents 1.



   Microbicides of the formula I with R1 = H. F or Cl, R2 = H and X oxygen are preferred.



   With regard to the ring structure, preference is given to those compounds of the formula I. in which A is -CH.-CH, - or -CH = CH- (iminodibenzyls and dibenzazepines) and those in which A is sulfur (phenothiazines), and especially those of the third Subgroups in which R, R1 and R2 have the narrow meanings given above.



   The following individual compounds are particularly preferred on account of their microbicidal action:
N-cyclopropylcarbonyliminodibenzyl,



  N- (iso-propyloxycarbonyl) -iminodibenzyl, N- (n-propyloxycarbonyl) -iminodibenzyl, N-ethyloxycarbonyl-dibenzazepine, N-ethyloxycarbonyl-iminodibenzyl, N-cyclopropylcarbonyI-dibenzazepine, and the compounds No. 1.22, 1.48 mentioned below, 2.13.3.4.3.5.3.9.4.1, 5.1.5.19 and 7.4.



   Compounds of the formula I can be obtained by reacting a compound of the formula II,
EMI2.1
    (11) prepared with a compound of formula III, wherein R 'is-COR or-COXR; A, X, R1, R2, R have the meanings given under formula I and Z represents a leaving group which is capable of reacting with N-acylation or (thio) carbamoylation.



   Halogen, in particular chlorine, bromine or iodine, for example, comes as the leaving group. or benzenesulfonyl, p-tosyl, trifluoroacetyl, acyl or lower alkylsulfonyl, preferably mesyl.



   In the case of n = 0, the acid RCOOH itself and its esters, but advantageously its acid anhydride or one of its acid halides, preferably the acid chloride or acid bromide, can be used for N-acylation.



   In the case of n = 1, the starting compound of the formula II can first be converted into a carbamoyl chloride of the formula IV by N-acylation with phosgene
EMI2.2
 be transferred. The intermediate of formula IV then reacts with a compound of formula V, in which Me represents hydrogen or a metal cation, preferably an alkali metal cation, and R and X have the meanings given under formula I to give end products of formula I.



   The N-acylation can be carried out in the presence of inert solvents or diluents. For example, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylenes, petroleum ether, halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, tetrachlorethylene; Ethers and ethereal compounds such as dialkyl ether (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.), anisole, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, propionitrile; N, N-dialkylated amides such as dimethylformamide; Dimethyl sulfoxide; Ketones such as acetone, diethyl ketone, methyl ethyl ketone and mixtures of such solvents with one another. In some cases, the xcyclizing agent itself can serve as a solvent.



   In the case of acylation, the presence of a reaction catalyst such as dimethylformamide can be advantageous.



   The reaction temperatures in the case of N-acylation with compounds of the formula III are between 0 and 10 ° C., preferably 0 and 150 ° C. or at the boiling point of the solvent or solvent mixture. When phosgene is used as the acylating agent, it is advantageous to work at lower temperatures of -30 up to + 100 C.



   In some cases, the use of acid-binding agents or condensing agents is advantageous. As such, organic and inorganic bases come into consideration, e.g. tertiary amines such as trialkylamines (trimethylamine, triethylamine, tripropylamine etc.), pyridine and pyridine bases (4-dimethylaminopyridine, 4-pyrrolidylaminopyridine etc.), oxides and hydroxides, carbonates and hydrogen carbonates of alkali and alkaline earth metals and alkali metal acetates.



   In some cases, hydrogen halide formed can also be passed through by passing inert gas, e.g. Nitrogen are expelled from the reaction mixture.



   The reaction of the intermediates IV with compounds of the formula V can in principle be carried out in inert solvents. Aromatic hydrocarbons such as benzene, toluene, xylenes are suitable for this purpose; aliphatic hydrocarbons such as petroleum ether, ligroin cyclohexane, ethers and ethereal compounds such as dialkyl ether (diethyl ether, t-butyl methyl ether, diisopropyl ether), dimethoxyethane, dioxane, tetrahydrofuran, anisole, ketones such as acetone, methyl ethyl ketone; Esters such as ethyl acetate, butyl acetate and mixtures of such and other solvents with one another. The reaction can be carried out at temperatures from -10 to + 180 ° C.



   The starting materials of the formulas II, III and V are known or are prepared by methods known per se. The preparation of the intermediates of formula IV is described herein.

 

   Some compounds of Formula 1 are known: N- (lower acyl) dibenzazepines are disclosed as feed additives in U.S. Patent 3,812,255; however, no action against phytopathogenic microorganisms is mentioned.



   Production and chemical and physical properties of: N-acetyl-iminodibenzyl, N-chloroacetyl-iminodibenzyl, N-ethoxycarbonyl-iminodibenzyl are described in: J. Chem. Soc. Chem. Comm. 1973 (8) page 282 J. Chem. Soc. Perk. Trans. 1974 (2) page 1648.



   A biological effect of these substances is not mentioned there.



   Chemical and physical properties of compounds of the formula
EMI3.1
 where X stands for COC2H5, COCH2CI, COC6Hs, CO2C2Hs are described in J. Chem. Soc. Perk. Trans. 1974 (1) 52.



  Their biological effectiveness has not been investigated.



   N-acylated dibenzazepines are also mentioned as intermediates in DE-OS 2 440 592. An activity against phytopathogenic microorganisms has not been described.



   N-Acryloyldibenzazepines substituted in the 2-position of the acid residue, their preparation and their use as photoconductors in electrophotographic processes are disclosed in DE-OS 2 104 557. A microbicidal action of these substances has not been reported.



   It has surprisingly been found that compounds of the formula I have a microbicide spectrum which is very favorable for practical needs. For example, they can be used to protect crops.



   The main area of application of compounds of the formula I is in the control of harmful microorganisms, in particular phytopathogenic fungi and bacteria. For example, the compounds of the formula I have a curative and preventive action for the protection of crop plants which is very favorable for practical needs without influencing them by undesirable side effects.

  In the context of the present invention, crop plants are, for example: cereals (wheat, barley, rye, oats, rice); Beets (sugar and fodder beets); Pome, stone and berry fruit (apple, pear, plum, peach, almond, cherry, strawberry, raspberry and blackberry); Legumes (beans, lentils, peas, soybeans); Oil crops (rapeseed, mustard, poppy seeds, olives, sunflowers, coconut, castor bean, cocoa, peanuts); Cucumber plants (pumpkin, cucumber, melons); Fiber plants (cotton, flax, hemp, jute); Citrus fruits: oranges, lemons, grapefruit, tangerines); Vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, peppers) or plants such as corn, tobacco, nuts, coffee, sugar cane, tea, grapevines, hops, banana and natural rubber plants and ornamental plants.



   With the active ingredients of the formula I, the microorganisms occurring on plants or on parts of plants (fruits, flowers, leaves, stems, tubers, roots) of these and related crops can be contained or destroyed, with plant parts which are subsequently growing being spared by such microorganisms. Active ingredients of the formula I are active, inter alia, against the following phytopathogenic fungi: e.g. against Helminthosporium and Venturia belonging to the Ascomycetes family, against Fungi imperfecti like Cercospora and Piricularia and against Phycomycetes like Plasmopara. Active ingredients of formula I act in particular against the Puccinia, Tilletia and Rhizoctonia belonging to the Basidiomycetes family; in addition, they are also effective against phytopathogenic bacteria, in particular against the Xanthomonas belonging to the Pseudomonadaceae family.



   They can also be used as dressing agents for the treatment of seeds (fruits, tubers, grains) and plant cuttings for the protection of fungal infections and against microorganisms occurring in the soil.



   The invention thus further relates to the use of the compounds of the formula I for combating phytopathogenic microorganisms or for the preventive prevention of an infection on plants.



   To control these microorganisms, the compounds of the formula I can be used on their own or together with suitable carriers and / or other additives. Suitable carriers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Active ingredients of formula I can also be mixed with e.g. pesticidal or plant growth-improving preparations can be used.



   The active substance content in commercially available agents is generally between 0.1 and 90%.



   In the following examples, temperatures are given in degrees Celsius, parts always mean parts by weight.



      Manufacturing examples:
Example I Preparation of
EMI3.2
   Iv- Qvclopropyharboiiyl-üiftiodll> eizil
12.6 g (0.12 mol) of cyclopropylcarbonyl chloride in 100 ml of anhydrous toluene are added dropwise to a solution of 21.45 g (0.11 mol) of iminodibenzyl in 300 ml of anhydrous toluene with stirring. The reaction mixture is then heated under reflux for a further 20 hours and the hydrogen chloride formed is expelled by passing nitrogen through it. After concentrating the reaction mixture in vacuo, an oily reaction product is obtained. This crystallizes when methanol is added.



  It is filtered. first washed with water, then with n-hexane and dried in vacuo.



   Mp 8687 C. Yield: approx. 97% of theory.



   Example 2 Preparation of
EMI3.3
   Iv-2.2. 1- TrichloracryIoyl-ni'iodibe? Yl
17.5 g (0.09 mol) of 2.2.1-trichloroacrylic acid chloride in 200 ml of anhydrous toluene are added to a solution of 17.6 g (0.09 mol) of iminodibenzyl in 300 ml of anhydrous toluene with stirring within 30 minutes drops. The reaction mixture is then heated under reflux for a further 20 hours and the hydrogen chloride formed is expelled by passing nitrogen through it. After concentrating the reaction mixture in vacuo, a crystalline crude product is obtained; this is washed successively with water and n-hexane and dried in vacuo.



   M.p .: 161-162 "C, yield: about 93% of theory.



   Example 3 Preparation of
EMI4.1
   N-2,4-dichlorophenoxyearbonyl dibenzyl
A solution of 0.1 mol of 2,4-dichlorophenol in 200 ml of ethyl acetate is added to 0.12 mol of NaOCH3 in 50 ml of methanol. Then 0.1 mol of chlorocarbonyliminostilbene, which is obtainable in a known manner from iminostilbene and phosgene, is added and the reaction mixture is heated under reflux for 4 hours. After cooling to room temperature, the mixture is washed successively with 0.5 normal sodium hydroxide solution and water, the organic phase is dried over MgSO4, filtered and concentrated in vacuo. The remaining oil crystallizes after the addition of diethyl ether.



   Mp 153-154 C, yield: about 65% of theory.



   Example 4 Preparation of
EMI4.2
   N-isopropyloxyearbo) lyl-iminodibenzyl
0.1 mol of NaOCH (CH3) 2 in 200 ml of isopropanol is mixed with 0.1 mol of chlorocarbonyliminodibenzyl, which is obtainable from iminodibenzyl and phosgene in a known manner, and the reaction mixture is heated under reflux for 30 minutes. After the isopropanol has been distilled off, the residue is taken up in ethyl acetate and washed with water. The organic phase is dried with MgSO4, filtered and concentrated. The product crystallizes after the addition of petroleum ether.



   105-106, yield: approx. 85% of theory.



   Example 5 Preparation of
EMI4.3
   N-propargyloxycarbonyl iminodibenzyl
0.1 mol of NaOCH2 - C = - CH in 200 ml of propargyl alcohol is mixed with 0.1 mol of chlorocarbonyliminodibenzyl, which is obtainable from iminodibenzyl and phosgene in a known manner, and the reaction mixture is heated under reflux for 30 minutes. After the solvent has been distilled off under reduced pressure, the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo. The oily residue is dissolved in diethyl ether and crystallized by adding petroleum ether.



   Mp 98-99 C, yield: approx. 51% of theory.



   Example 6 Preparation of
EMI4.4

To a solution of 19.9 g of thiodiphenylamine (0.1 mol) in 200 ml of toluene (abs.) Prepared at 70, 11.5 g of cyclopropanecarboxylic acid chloride (0.11 mol) in 100 ml of toluene (abs.) Are added with stirring within 30 minutes. drop.



  The mixture is then heated to reflux, the resulting HCl being expelled using nitrogen. After concentrating the reaction mixture in vacuo, a crystalline product is obtained, which is washed with water and then with n-hexane. Finally, it is dried in a vacuum.



  Yield: 23 g = 86% of theory. M.p. 112-114 C.



   The following compounds of the formula I can be prepared in an analogous manner: (Unless otherwise stated, the physical constants are melting points) Table I
Compounds of the formula
EMI4.5

EMI4.6


 <tb> verb. <SEP> R <SEP> Physical
 <tb> No. <SEP> constant <SEP> [ <SEP> C]
 <tb> 1.1 <SEP> -CH2C1 <SEP> 94-96
 <tb> 1.2 <SEP> -OC2H5 <SEP> 90-92
 <tb> 1.3 <SEP> -OCH3 <SEP> 111-112
 <tb> 1.4 <SEP> cyclopropyl <SEP> 86-87
 <tb> 1.5 <SEP> 2-furanyl <SEP> 173-174
 <tb> 1.6 <SEP> -C6H3 (CH3) 2 (3.5) <SEP> 151-152
 <tb> 1.7 <SEP> CH3 <SEP> 94-9i
 <tb> 1.8 <SEP> -OC6H3Cl2 (2.4) <SEP> 153-154
 <tb> 1.9 <SEP> -OC3H7 (n) <SEP> 80-81
 <tb> 1.10 <SEP> -OC3H7 (iso) <SEP> 104-105
 <tb> 1.11 <SEP> -OC4Hg (n) <SEP> 62-63
 <tb> 1.12 <SEP> -OCHCH2CH3 <SEP> 95-96
 <tb> <SEP> CH3
 <tb> 1.13 <SEP> -OCH2-CH (CH3) 2 <SEP> 89-90
 <tb> 1.14 <SEP> -C (CH3) 3 <SEP> 116
 <tb> 1.15 <SEP> -CHBr-CH3 <SEP>

   108-110
 <tb>
EMI5.1


 <tb> 1.16 <SEP> cyclohexyl <SEP> 118-120
 <tb> 1.17 <SEP> -O (CH2) 11CH3 <SEP> Kp. <SEP> = <SEP> ¯ <SEP> 140 / 0.01 <SEP> mm
 <tb> 1.18 <SEP> -C6H3Cl2 (3.5) <SEP> 170-172
 <tb> 1.19 <SEP> -CH-CH2-CCl3 <SEP> 195-197
 <tb> <SEP> I
 <tb> <SEP> Cl
 <tb> <SEP> C1
 <tb> 1.20 <SEP> -O- <SEP> too <SEP> <* -0- <SEP> \ <SEP> <- <SEP> -1 <SEP> 124-125
 <tb> <SEP> = &commat; <SEP> =
 <tb> 1.21 <SEP> ortho-phenylphenoxy <SEP> 138-139
 <tb> 1.22 <SEP> OCH2-C = -CH <SEP> zuCH <SEP> 98-99
 <tb> 1.23 <SEP> -OCH2CH2Cl <SEP> 77-78
 <tb> 1.24 <SEP> -CCI = <SEP> CCk <SEP> 161-162
 <tb> 1.25 <SEP> cyclohexyl <SEP> 134-135
 <tb> 1.26 <SEP> 3,5-dimethylcyclohexyl <SEP> 130-131
 <tb> 1.27 <SEP> -C5Hll (n) <SEP> Kp. <SEP> 172 "/0.08 <SEP> mm
 <tb> 1.28 <SEP> -CH2CH (CH3) 2 <SEP> Kp. <SEP> 164 "/0.07 <SEP> mm
 <tb> 1.29 <SEP> -CH2CH3 <SEP> 73-74
 <tb> 1.30 <SEP> -C3H7 (n) <SEP> Kp.

   <SEP> 160 "/0.04 <SEP> mm
 <tb> 1.31 <SEP> -C4H9 (n) <SEP> Kp. <SEP> 175 "/0.05 <SEP> mm
 <tb> 1.32 <SEP> -CH2C (CH3) 3 <SEP> 111-112
 <tb> 1.33 <SEP> -CH (CH3) 2 <SEP> 94-95
 <tb> 1.34 <SEP> -CHC12 <SEP> 7678
 <tb> 1.35 <SEP> -C (CH3) 3 <SEP> 83-85
 <tb> 1.36 <SEP> p.Tolyl <SEP> 147-148
 <tb> 1.37 <SEP> m-tolyl <SEP> 128-130
 <tb> 1.38 <SEP> o-tolyl <SEP> 160-161
 <tb> 1.39 <SEP> -C6H4CF3 (3) <SEP> 134-135
 <tb> 1.40 <SEP> -CH2OCH3 <SEP> 64-65
 <tb> 1.41 <SEP> -C <SEP> = <SEP> CH2 <SEP> 94-95
 <tb> <SEP> CH3
 <tb> 1.42 <SEP> -CH <SEP> = <SEP> C (CH3) 2 <SEP> 8082
 <tb> 1.43 <SEP> -C6H4 (OCH3) (2) <SEP> 120-122
 <tb> 1.44 <SEP> cyclopentyl <SEP> 117-118
 <tb> 1.45 <SEP> -CH <SEP> = <SEP> CH2 <SEP> 75-78
 <tb> 1.46 <SEP> cyclobutyl <SEP> 83-84
 <tb> 1.47 <SEP> 2-methyl-cyclopropyl <SEP> Kp.

   <SEP> 170 "/0.05 <SEP> mm
 <tb> 1.48 <SEP> -SC2Hs <SEP> 117-119
 <tb> 1.49 <SEP> -CH = O <SEP> = <SEP> 0 <SEP> 124-127
 <tb> 1.50 <SEP> -OCH2CH2-N / H <SEP> | <SEP> 78-80
 <tb> <SEP> ¯ <SEP> &commat;
 <tb> 1.51 <SEP> -SCH3 <SEP> 100-101
 <tb> <SEP> ¯ <SEP> &commat;
 <tb> 1.52 <SEP> -CH = CH- <SEP> v <SEP> + * - C1 <SEP> 168-170
 <tb> <SEP> \ ¯ /
 <tb> 1.53 <SEP> -CH = CH-c6 = HS <SEP> 176-177
 <tb> 1.54 <SEP> -CCI3
 <tb> 1.55 <SEP> -CH2CH2-CI <SEP> 78
 <tb> 1.56 <SEP> -OCH2CH2CCH
 <tb> 1.57 <SEP> -CH2CH2OCH3
 <tb> 1.58 <SEP> 2,3-dichlorophenyl
 <tb> 1.59 <SEP> 2,3-dimethylphenyl
 <tb> Table II
Compounds of the formula
EMI5.2

EMI5.3


 <tb> verb. <SEP> R <SEP> Physical
 <tb> No.

   <SEP> constant
 <tb> 2.1 <SEP> -CH2Cl <SEP> 141
 <tb> 2.2 <SEP> -CHCl2 <SEP> 140-141
 <tb> 2.3 <SEP> -CC13
 <tb> 2.4 <SEP> -C2H5 <SEP> 8082
 <tb> 2.5 <SEP> -C3H7 (n)
 <tb> 2.6 <SEP> -C3H7 (iso)
 <tb> 2.7 <SEP> -CH3 <SEP> 95-98
 <tb> 2.8 <SEP> -CH2CH2CI
 <tb> 2.9 <SEP> -C4H9 (n)
 <tb> 2.10 <SEP> -OCH3 <SEP> 123
 <tb> 2.11 <SEP> -OC2H5 <SEP> 134
 <tb> 2.12 <SEP> -OC3H7 (n) <SEP> 79
 <tb> 2.13 <SEP> -OC3H7 (iso) <SEP> 109
 <tb> 2.14 <SEP> -OCH2CH (CH3) 2
 <tb> 2.15 <SEP> -OCH2C = -CH
 <tb> 2.16 <SEP> -CH = CH2
 <tb> 2.17 <SEP> -CCl = CCl2 <SEP> 183
 <tb> 2.18 <SEP> -CH = C (CH3) 2 <SEP> 85-87
 <tb> 2.19 <SEP> -C (CH3) = CH2) <SEP> 132-134
 <tb> 2.20 <SEP> -CH2CH (CH3) 2 <SEP> 132
 <tb> 2.21 <SEP> -CH2OCH3
 <tb> 2.22 <SEP> -CH2CH2OCH3
 <tb> 2.23 <SEP> cyclopropyl <SEP> 97-98
 <tb> 2.24 <SEP> -CH2-C (CH3) 3 <SEP> 130-132
 <tb> 2.25 <SEP> 2-furanyl <SEP> 179-180
 <tb> 2.26 <SEP> 2-tetrahydrofuranyl <SEP> 144-146
 <tb> 2.27 <SEP> m-tolyl

    <SEP> 126
 <tb> 2.28 <SEP> o-tolyl <SEP> 154-156
 <tb> 2.29 <SEP> p-tolyl <SEP> 170-172
 <tb> 2.30 <SEP> 3,5-dichlorophenyl <SEP> 178
 <tb> 2.31 <SEP> 2,3-dimethylphenyl
 <tb> 2.32 <SEP> cyclohexyl <SEP> 170-172
 <tb> 2.33 <SEP> 2,4-dichlorophenoxy <SEP> 153-154
 <tb> 2.34 <SEP> 2-methylcyclopropyl <SEP> 98
 <tb> 2.35 <SEP> -CH (Cl) CH2CH3 <SEP> 172
 <tb> 2.36 <SEP> -CH (Br) CH3 <SEP> 124
 <tb> 2.37 <SEP> 2-methoxyphenyl <SEP> 133
 <tb> 2.38 <SEP> cyclopentyl <SEP> 146
 <tb> 2.39 <SEP> -C (CH3) 3 <SEP> 105
 <tb> 2.40 <SEP> C6H4 (CF3) (3) <SEP> 117
 <tb> 2.41 <SEP> 3,5-dimethylphenyl <SEP> 167
 <tb> <SEP> / CH3
 <tb> / <SEP> ¯ <SEP> 128
 <tb> 2.42 <SEP> -. <SEP> H <SEP> \. <SEP> 128
 <tb> <SEP> y
 <tb> 2.43 <SEP> raw3
 <tb> <SEP> - <SEP> OCH (CH3) CH2N (CH3) 2 <SEP> 102-104
 <tb> 2.44 <SEP> -OCH2CH2N (C2H5) 2 <SEP> 205-207
 <tb> <SEP> / ci
 <tb> 2.45 <SEP> -CH2-O- <SEP> // <SEP> <.

   <SEP> 142-143
 <tb> <SEP> \ <SEP> ¯ /
 <tb> 2.46 <SEP> -CH <SEP> = <SEP> CH-C6H5 <SEP> ci <SEP> 145-147
 <tb> 2.47 <SEP> -CH (CI) CH2CCI3 <SEP> 170-172
 <tb> 2.48 <SEP> -S-C2H5 <SEP> 97-98
 <tb> Table III
Compounds of the formula
EMI5.4
   Verb. R R1 Physical No. Constant [C] 3.1 -CH3 Cl 109 3.2 -OCH3 Cl 155-156 3.3 -OC2H5 Cl 75-76 3.4 -OC3H7 (iso) Cl 78 3.5 -OC3H7 (n) Cl 83-84 3.6 Cyclopropyl CF3 3.7 -CH3 NO2 157-159 3.8 -C2H5 CF3 3.9 -OC3H7 (n) F 74-78 Table IV
Compounds of the formula
EMI6.1
 Verb. R R1 Physical No. Constant [C] 4.1 -OC2H5 Cl 88 4.2 -OCH3 Cl 131 Table V
Compounds of the formula
EMI6.2

EMI6.3


 <tb> verb. <SEP> R <SEP> Physical
 <tb> No.

   <SEP> constant <SEP> [C]
 <tb> 5.1 <SEP> cyclopropyl <SEP> 112-114
 <tb> 5.2 <SEP> 3,5-dimethylphenyl <SEP> 117-118
 <tb> 5.3 <SEP> 2-furanyl <SEP> 143-145
 <tb> 5.4 <SEP> 4-anisyl <SEP> 168-169
 <tb> <SEP> / CH3
 <tb> <SEP> 3
 <tb> 5.5 <SEP> -. <SEP> H <SEP> \. <SEP> 129-130
 <tb> <SEP> OH3
 <tb> 5.6 <SEP> cyclohexyl <SEP> 148-150
 <tb> 5.7 <SEP> -C (CI) CCl2 <SEP> 127-129
 <tb> 5.8 <SEP> 3,5-dimethylbenzyl <SEP> 85-86
 <tb> 5.9 <SEP> 4-ethoxyphenyl <SEP> 165-166
 <tb> 5.10 <SEP> 3,5-dichlorophenyl <SEP> 171-172
 <tb> 5.11 <SEP> 2-ethoxyphenyl <SEP> 142-143
 <tb> 5.12 <SEP> 4-methoxybenzyl <SEP> 118-120
 <tb> 5.13 <SEP> -C6H4 (C4H9 <SEP> tert) (4) <SEP> 171-173
 <tb> 5.14 <SEP> -CHCl2 <SEP> 152-153
 <tb> 5.15 <SEP> -CH (Br) CH3 <SEP> 145-146
 <tb> 5.16 <SEP> -CH2CH2CI <SEP> 115-117
 <tb> 5.17 <SEP> -CH (C2H5) 2 <SEP> 85-86
 <tb>
EMI6.4


 <tb> 5.18 <SEP> 2,5-dichlorophenyl <SEP> 159-160
 <tb> 5.19 <SEP>

   -CH (CH3) 2 <SEP> 143-144
 <tb> 5.20 <SEP> -CH (C2H5) C4H9 (n) <SEP> Kp. <SEP> 173 "/0.03 <SEP> mm
 <tb> 5.21 <SEP> -CH (CI) CH2CCI3 <SEP> 156157
 <tb> 5.22 <SEP> -CC13 <SEP> 145-146
 <tb> 5.23 <SEP> -C (CH3) 3 <SEP> 150-152
 <tb> 5.24 <SEP> 3,4-dimethylphenyl <SEP> 196-197
 <tb> 5.25 <SEP> benzyl <SEP> 149-150
 <tb> 5.26 <SEP> -CIH - \ <SEP> / - C1 <SEP> 70
 <tb> <SEP> U <SEP> 'f = <SEP> 70
 <tb> 5.27 <SEP> 2,4-dichlorophenyl <SEP> 113-115
 <tb> 5.28 <SEP> -C3H7 (n)
 <tb> Table VI
Compounds of the formula
EMI6.5

EMI6.6

 Verb. <SEP> R <SEP> Physical
 <tb> No. <SEP> constant <SEP> [ <SEP> C]
 <tb> 6.1 <SEP> 3,5-dimethylphenyl <SEP> oil
 <tb> <SEP> F1
 <tb> 6.2 <SEP> -OH2O- <SEP> // <SEP> 0- * <SEP> 100-101
 <tb> <SEP> L
 <tb> <SEP> \ cl
 <tb> <SEP> OH
 <tb> <SEP> 6.3 <SEP> Kp.

   <SEP> 205 "/ 0.5 <SEP> mm
 <tb> <SEP> ¯ <SEP>
 <tb> \ eck3
 <tb> <SEP> OH3
 <tb> 6.4 <SEP> 3,5-dichlorophenyl <SEP> 145-146
 <tb> 6.5 <SEP> cyclohexyl <SEP> 141-142
 <tb> 6.6 <SEP> 2-furanyl <SEP> 130-132
 <tb> 6.7 <SEP> 4-ethoxyphenyl <SEP> 13S135
 <tb> 6.8 <SEP> 2-ethoxyphenyl <SEP> 118-120
 <tb> 6.9 <SEP> -CH2-O-C6H4C1 (4) <SEP> 8688
 <tb> 6.10 <SEP> -CH2OC6H4Cl (2) <SEP> 142-143
 <tb> 6.11 <SEP> -C (Cl) = CC12 <SEP> 113-115
 <tb> 6.12 <SEP> 3,4-dimethylphenyl <SEP> 10S106
 <tb> 6.13 <SEP> -CH (C2H5) C4H9 (n) <SEP> Kp. <SEP> 186 "/0.04 <SEP> mm
 <tb> 6.14 <SEP> 3,5-dimethylphenyl <SEP> 123-125
 <tb> 6.15 <SEP> 3-methoxybenzyl <SEP> 50
 <tb> 6.16 <SEP> cyclopropyl <SEP> Kp. <SEP> 196 "/ 0.1 <SEP> mm
 <tb> 6.17 <SEP> CH2OC6H4Cl2 (2.4) <SEP> 76-78
 <tb> 6.18 <SEP> -CH- (C2H5) 2 <SEP> Kp.

   <SEP> 185 "/0.05 <SEP> mm
 <tb> 6.19 <SEP> -CH (Br) CH3 <SEP> 135-137
 <tb> 6.20 <SEP> -CH2CH2C1 <SEP> 103-104
 <tb> 6.21 <SEP> CH2OC6H4Br (4) <SEP> 108-110
 <tb> Table VII
Compounds of the formula
EMI7.1

EMI7.2


 <tb> <SEP> verb. <SEP> R <SEP> R2 <SEP> Physical
 <tb> No. <SEP> constant <SEP> [ <SEP> C]
 <tb> 7.1 <SEP> 3,5-dichlorophenyl <SEP> Cl <SEP> 155-156
 <tb> 7.2 <SEP> 2-ethoxyphenyl <SEP> Cl <SEP> 171-173
 <tb> 7.3 <SEP> -CH2OC6H3Cl2 (3.5) <SEP> C1 <SEP> 165-167
 <tb> 7.4 <SEP> cyclopropyl <SEP> Cl <SEP> 86-87
 <tb> 7.5 <SEP> 3,5-dimethylbenzyl <SEP> Cl <SEP> 130-131
 <tb> 7.6 <SEP> 3,5-dimethylphenyl <SEP> Cl <SEP> 147-148
 <tb> 7.7 <SEP> 4-ethoxyphenyl <SEP> Cl <SEP> 181-182
 <tb> 7.8 <SEP> CH2OC6H4Cl (4) <SEP> Cl <SEP> 148-150
 <tb> 7.9 <SEP> -C (CI) = CCI2 <SEP> Cl <SEP> 137-138
 <tb> <SEP> / CH3
 <tb> <SEP> ¯ <SEP> y
 <tb> 7.10 <SEP> -.

   <SEP> H <SEP> ./ <SEP> Cl <SEP> 157-158
 <tb> <SEP> OH3
 <tb> <SEP> J
 <tb> 7.11 <SEP> -CH2-O - \ <SEP> \\
 <tb> \ <SEP> C1 <SEP> 152-153
 <tb> <SEP> lSir
 <tb> 7.12 <SEP> p-anisyl <SEP> Cl <SEP> 149-150
 <tb> 7.13 <SEP> cyclohexyl <SEP> Cl <SEP> 130-131
 <tb> 7.14 <SEP> XC2Hs <SEP> CF3
 <tb> Table VIII
Compounds of the formula
EMI7.3

EMI7.4


 <tb> verb. <SEP> R <SEP> Physical
 <tb> <SEP> no. <SEP> constant <SEP> [ <SEP> Cj
 <tb> <SEP> / CH3
 <tb> <SEP> J
 <tb> <SEP> 8.1 <SEP> -.

   <SEP> H <SEP> 120-122
 <tb> <SEP> CH3
 <tb> 8.2 <SEP> CH2OC6H4Br (4) <SEP> 142-143
 <tb> 8.3 <SEP> 4-ethoxyphenyl <SEP> 134-135
 <tb> 8.4 <SEP> 3,5-dimethylphenyl <SEP> 133-134
 <tb> 8.5 <SEP> cyclohexyl <SEP> 161-162
 <tb> <SEP> ICl
 <tb> <SEP> F1
 <tb> 8.6 <SEP> -CH2-O- * <SEP> -Br <SEP> 104-106
 <tb> 8.7 C6H4 (CF3) (3) 97-98 8.8 2-furanyl 114-115 8.9 CH2OC6H3Cl2 (3.5) 127-128 8.10 4-nitrophenyl 156-157 8.11 cyclopropyl bp. 175 / 0.5mm 8.12 -OC2Hs 8.13 -C3H, (iso) Table IX
Compounds of the formula
EMI7.5
 Verb. R Physical No.

  Constant [Cj 9.1 Cyclopropyl 70-71 9.2 -CH (Br) CH3 120-121 9.3 H3 67-68 9.4 -CH2CI 100-101 9.5 -CH (C2H5) 2 bp 170 / 0.01 mm 9.6 -CH2Br 80-82 9.7 -CH (Br) C2H5 104 105 9.8 -OC2H5 Table X
Compounds of the formula
EMI7.6

EMI7.7


 <tb> verb. <SEP> R <SEP> Physical
 <tb> No.

   <SEP> constant <SEP> [ <SEP> C]
 <tb> 10.1 <SEP> phenoxy <SEP> 129-131
 <tb> 10.2 <SEP> 2,4-dimethylphenoxy <SEP> 137-139
 <tb> 10.3 <SEP> 4-methylphenoxy <SEP> 192-195
 <tb> 10.4 <SEP> -O-C4H9 (n) <SEP> 7072
 <tb> 10.5 <SEP> -O-C3H7 (n) <SEP> 96-98
 <tb> 10.6 <SEP> -O-C2Hs <SEP> 112-114
 <tb> 10.7 <SEP> -O-C3H7 (iso) <SEP> 120-122
 <tb> 10.8 <SEP> O-CH-C2H5 <SEP> 86-87
 <tb> <SEP> CH3
 <tb>
Formulation example
Example F-1: Fixed processing forms
Dusts and flour agents generally contain up to 100% of the active ingredient. A 5% dusting agent can consist, for example, of 5 parts of the active ingredient and 95 parts of an additive such as talc or of 2 parts of active ingredient, 1 part of highly disperse silica and 97 parts of talc.



  In addition, further mixtures with such and other carrier materials and additives customary in formulation technology are conceivable. In the production of these dusts, the active ingredients are mixed and ground with the carriers and additives and can be dusted in this form.



   Granules such as coated granules, impregnated granules, homogeneous granules and pellets (= grains) usually contain 1 to 80% of the active ingredient. A 5% granulate can e.g. from 5 parts of the active ingredient, 0.25 parts of epoxidized vegetable oil, 0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol and 91 parts of kaolin (preferred grain size 0.30.8 mm). One can proceed as follows in the production of the granulate:
The active substance is mixed with epoxidized vegetable oil and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin, and the acetone is then evaporated off in vacuo. Such microgranules are advantageously used to control soil fungi.



   Example F-2 Liquid Forms of Workup
A distinction is generally made between active ingredient concentrates that are dispersible or soluble in water and aerosols. The water-dispersible active ingredient concentrates include e.g. Wettable powders B w (wettable powders) and pastes, which usually contain from 25 to 90% of the active ingredient in commercial packs and from ready-to-use solutions to 0.01 to 15% of the active ingredient, emulsion concentrates contain 10 to 50% and solution concentrates contain 0.0001 in the ready-to-use solution Up to 20% active substance, for example a 70% wettable powder can be made from 70 parts of the active ingredient, 5 parts of sodium dibutylnaphthylsulfonate, and 3 parts of naphthalenesulfonic acids - phenolsulfonic acids - formaldehyde condensate (in a mixing ratio of 3: 2: 1), 10 parts of kaolin and 12 parts Chalk, e.g.

  Champagne chalk made up. A 40% wettable powder can e.g. consist of the following substances: 40 parts of active ingredient, 5 parts of sodium lignin sulfonate, 1 part of sodium dibutylnaphthyl sulfonate and 54 parts of silica. A 25% wettable powder can be produced in different ways. So this can e.g. composed of: 25 parts of the active substance, 4.5 parts of calcium lignin sulfonate, 1.9 parts (chalk e.g. Champagne chalk) / hydroxyethylene cellulose mixture (1: 1) 1.5 parts of sodium dibutylnaphthylsulfonate, 19.5 parts of silica, 19.5 parts of chalk (e.g. champagne chalk) and 28.1 parts of kaolin.

  A 25% wettable powder can e.g. also consist of 25 parts of active ingredient, 2.5 parts of isooctylphenoxypolyoxyethylene-ethanol, 1.7 parts (Champagne) chalk / hydroxyethyl cellulose mixture (1: 1), 8.3 parts of sodium silicate, 16.5 parts of diatomaceous earth and 46 parts of kaolin. A 10% wettable powder can e.g. produce from 10 parts of the active ingredient, 3 parts of a mixture of sodium salts of saturated fatty alcohol sulfonates, 5 parts of naphthalenesulfonic acid / formaldehyde condensate and 82 parts of kaolin. Other wettable powders can be mixtures of 5 to 30% of the active substance together with 5 parts of an absorbent carrier material such as silica, 55 to 80 parts of a carrier material such as kaolin and a dispersant mixture consisting of 5 parts of sodium aryl sulfonate and 5 parts of an alkyl aryl polyglycol ether.

  A 25% emulsion concentrate can e.g. The following emulsifiable substances contain: 25 parts of the active ingredient, 2.5 parts of epoxidized vegetable oil, 10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture, 5 parts of dimethylformamide and 57.5 parts of xylene.



   Such concentrates can be used to produce emulsions of the desired application concentration, which are particularly suitable for foliar application. In addition, other wettable powders with different mixing ratios or other carrier materials and additives commonly used in formulation technology can be produced. The active ingredients are intimately mixed with the additives mentioned in suitable mixers and ground on appropriate mills and rollers. This gives wettable powder and excellent wettability and suspension which can be diluted with water to form suspensions of the desired concentration and can be used in particular for leaf application. Such means also belong to the invention.



     Biological examples
The spray liquors used in the examples below were formulated as described above.



   Example B-1 Effect against Erysphe graminis on barley Residual protective effect
Approx. Barley plants 8 cm high were sprayed with a spray mixture (0.02% active substance) prepared from wettable powder of the active ingredient. After 34 hours, the treated plants were dusted with conidia of the fungus.



  The infected barley plants were placed in a greenhouse at approx. 22 C and the fungal attack was assessed after 10 days. Among other things, compound no. 1.7 completely prevented fungal attack in comparison to untreated control plants (100% attack).



   Example B-2 Action against Cercospora arachidicola on peanut plants Residual protective action
Peanut plants 10-15 cm high were sprayed with a spray mixture (0.02% active substance) made from wettable powder of the active substance and infected with a conidia suspension of the fungus 48 hours later. The infected plants were incubated for 72 hours at about 21 ° C. and high atmospheric humidity and then placed in a greenhouse until the typical leaf spots appeared. The fungicidal activity is assessed 12 days after infection based on the number and size of the spots that appear.



   Peanut plants which have been treated with spray liquors which contain one of the compounds No. 1.1 or 1.2 as active substance showed less than 10% infection compared to untreated control plants (100% attack).



   Example B-3
Effect against Rhizoctonia solani on cabbage Effect after soil application
The mushroom was grown on sterile millet grains and added to a soil-sand mixture. The infected soil was filled into bowls and sown with cabbage seeds. Immediately after sowing, the test preparation formulated as a wettable powder was poured over the earth as an aqueous suspension (20 ppm of active substance based on the volume of the earth). The earth trays were then placed in the greenhouse at approx. 24 C for 2-3 weeks and kept constantly moist by gently showering them over. When evaluating the test, the emergence of the cabbages was determined.

 

   After treatment with wettable powders which contained one of the compounds Nos. 1.2, 1.4, 1.20, 1.21 or 2.29 as active substance, over 80% of the cabbage seeds sprouted and the plants had a healthy appearance.



   Example B-4 Action against Piricularia oryzae on rice plants Residual protective effect
After growing for two weeks, rice plants were sprayed with a spray mixture (0.02% active substance) prepared from wettable powder of the active ingredient. After 48 hours, the treated plants were infected with a conidia suspension of the fungus. After 5 days of incubation at 95-100% relative humidity and 24 C, the fungal attack was assessed.



   Rice plants which have been treated with a spray mixture which contains one of the compounds No. 1.2 or 2.11 as active substance showed less than 10% fungal attack in comparison to untreated control plants (100% attack).



   Example B-5 Action against Phy toph thora infestans on tomato plants Residual protective action
After growing for 3 weeks, tomato plants were sprayed with a spray mixture (0.06% active substance) prepared from wettable powder of the active ingredient. After 24 hours, the treated plants were infected with a sporangia suspension of the fungus. The fungal attack was assessed after incubation of the infected plants for 5 days at 90-100% relative atmospheric humidity and 20 C.



   In the above experiment against Phytophthora pathogens, compounds No. 1.2, 1.4, 1.9 almost completely prevented the fungal attack.



   Example B-6 Residual protective action against ven turle inaequalls on apple shoots
Apple cuttings with 10-20 cm long fresh shoots were sprayed with a spray mixture (0.06% active ingredient) made from wettable powder of the active ingredient. After 24 hours, the treated plants were infected with a conidia suspension of the fungus. The plants were then incubated for 5 days at 90-100% relative atmospheric humidity and placed in a greenhouse at 20-24 C for a further 10 days. Scab infestation was assessed 15 days after infection. Among other things, the compounds nos. 1.9, 1.10 and 1.4 even prevented the disease attack in a concentration of 0.02%.



   Example B-7
Action against Puccin ia graminis on wheat a) Residual protective action
Wheat plants were sprayed 6 days after sowing with a spray mixture (0.06% active ingredient) prepared from wettable powder of the active ingredient. After 24 hours, the treated plants were infected with an uredospore suspension of the fungus. After incubation for 48 hours at 95-100% relative humidity and approx. 20 C, the infected plants were grown in a greenhouse at approx.



  22 C set up.



   The rust pustule development was assessed 12 days after the infection. Compounds No. 1.2, 1.4, 1.9-1.12, 1.22, 1.41,1.42,1.45, 1.48, 1.56,1.57,2.2-2.16, 2,23, 3.43.6,4.1, 5.19, 7.4, 7.14 inhibited the rust pustule attack to less than 10% compared to untreated control plants (100% rust pustules).



  b) Systemic effect
A spray liquor prepared from wettable powder of the active ingredient was poured into wheat plants 5 days after sowing (0.006% of active ingredient based on the volume of the soil). After 3 days, the treated plants were infected with an uredospore suspension of the fungus. After incubation for 48 hours at 95-100% relative atmospheric humidity and approx. 20 C, the infected plants were placed in a greenhouse at approx. 22 C The rust pustule development was assessed 12 days after infection. Compounds of formula I showed strong effects. Compounds No. 1.2, 1.4, 1.9, 1.22.2.11.2.13,4.1,5.19 and 7.4 completely prevented the spread of the disease.



   Example B-8 Action Against Tilletia Caries
Tilletia spores are in a spray mixture containing 600 ppm of active ingredient for 15 min. suspended. The spore-substance mixture is pipetted dropwise onto the surface of finely screened, moistened earth in petri dishes. The earth shells prepared in this way are set up in high humidity and at a temperature of 20 ° C.



  After about 10 days, spore germination is assessed under the magnifying glass. The effect of the test substances is determined based on the number and length of the germ tubes.



   Among other compounds No. 1.1 completely suppressed germination.



   Example B-9 Effect against Hehn üz th osporiuin gramineum
Wheat grains are contaminated with a spore suspension of the mushroom and dried again. The contaminated grains are pickled with a suspension of the test substance made from wettable powder (600 ppm active ingredient based on the weight of the seeds). After two days the grains are placed on suitable agar dishes and after a further four days the development of the fungal colonies around the grains is assessed. The number and size of the fungal colonies are used to assess the test products.



   Among others, the compounds Nos. 1.1, 1.2, 1.9, 1.10 and 2.11 prevented the fungal attack almost completely.



   Example B-10 Action Against Xan th omonas oryzae on Rice Systemic Effect
After growing for 6 weeks in a greenhouse, rice plants of the Caloro or S6 variety were watered with a suspension of the test substance (0.006% active substance based on the volume of the earth). Three days after this treatment, the plants were placed in a climatic room at 24 C and 75-80% relative humidity and infected.

 

  The infection occurred by cutting off the leaf tips with scissors that had previously been immersed in a suspension of Xanthomonas oryzae. After incubation in the same room for 10 days, the cut leaves withered, curled and became necrotic. The extent of these disease symptoms served to assess the systemic effectiveness of the test substance.



   Plants treated with Compound Nos. 1.45 or 2.19 showed less than 10% necrosis compared to untreated control plants (100% necrosis).



   The results of the biological examples B-1 to B-10 demonstrate a high activity and broad activity of the compounds of the formula I against biologically very different phytopathogenic fungi and bacteria.


    

Claims (9)

 PATENT CLAIMS 1. Compounds of Formula I EMI1.1  wherein R is a C1-C6-alkyl or C3-C7-cycloalkyl which is optionally substituted by halogen or Cl-C3-alkoxy; a C2-C5-alkenyl optionally substituted by halogen or methyl; C3-C5 alkynyl; a 2-furyl optionally substituted by halogen, methyl or methoxy; or a phenyl optionally substituted by halogen, cyano, C1-C3-alkyl, C1-C3 alkoxy, trifluoromethyl or nitro; n is 0 or 1, X and Y are independently oxygen or sulfur, A is oxygen, sulfur, -CH2-, -CH2CH2- or -CH = CH- and R1 and R2 are independently hydrogen, halogen, methoxy or trifluoromethyl stand.  2. Compounds of formula I, according to claim 1, wherein A is -CH2-CH2-.  3. Compounds of the formula according to claim 1, wherein A is -CH = CH-.  4. Compounds of formula I, according to claim 1, wherein A is sulfur.  5. Compounds according to any one of claims 1 to 4, wherein R1 = H, F or Cl, R2 = H and X are oxygen.  6. A process for the preparation of compounds of the formula I according to claim 1, characterized by reaction of a compound of the formula II EMI1.2  with a compound of formula III R'-Z (III) where R 'is -COR or -COXR, A, X, R1, R2 and R have the meanings given for formula I and Z is a N-acylation. (Thio) carbamoylation is a reactive leaving group.  7. Means for combating and / or preventing microorganism infestation, characterized in that it contains, as at least one active ingredient, a compound of the formula I according to claim 1, together with one or more suitable carrier materials and / or distribution agents.  8. Use of compounds of formula I according to claim 1 for combating microorganisms.  9. Use according to claim 8, characterized in that it is phytopathogenic microorganisms.  The present invention relates to compounds of the formula EMI1.3  wherein R is a C1-C6-alkyl or C3-C7-cycloalkyl optionally substituted by halogen or C-C3-alkoxy; a C2 C5 alkenyl optionally substituted by halogen or methyl; C3-C5 alkynyl; a 2-furyl optionally substituted by halogen, methyl or methoxy; or a phenyl optionally substituted by halogen, cyano, CI-C3-alkyl, C-C3-alkoxy, trifluoromethyl or nitro; n is 0 or 1, X and Y are independently oxygen or sulfur, A is oxygen, sulfur, -CH2-, -CH2CH2- or -CH = CH- and R1 and R2 are independently hydrogen, halogen, methoxy or trifluoromethyl stand.  Depending on the number of C atoms specified, alkyl or alkyl moiety of another substituent means, for example, the following groups: methyl, ethyl, propyl, butyl, pentyl or hexyl and their isomers, such as Isopropyl, isobutyl, tert-butyl, isopentyl, etc. alkenyl stands for an unsaturated, aliphatic radical with one or more C = C double bonds, consisting of a maximum of 7 carbon atoms; for example for vinyl, propenyl- (l), allyl, butenyl- (l), butenyl- (2), butenyl- (3), etc. or CH3-CH = CHCH = CH-etc. Cycloalkyl is understood to mean, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Depending on the number of carbon atoms, alkynyl means the following groups: Propynyl (1), propargyl, butynyl (1), butynyl (2), etc. Here and below, halogen represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.  Compounds of formula I show a very valuable microbicide spectrum. They can e.g. against phytopathogenic microorganisms, especially against plant-damaging fungi and bacteria.  A preferred group of microbicides consists of compounds of the formula I in which R represents a C2-C4-alkyl group which is optionally substituted by halogen and n denotes 0 or 1.  Another preferred group of microbicides consists of compounds of the formula I in which R is C3-C4 cycloalkyl, in particular cyclopropyl and n is 0 or 1.    A further preferred group of microbicides form compounds of the formula I in which R represents a C2-C5-alkenyl radical which is optionally substituted by halogen and n represents 1.  Microbicides of the formula I with R1 = H. F or Cl, R2 = H and X oxygen are preferred.  With regard to the ring structure, preference is given to those compounds of the formula I. in which A is -CH.-CH, - or -CH = CH- (iminodibenzyls and dibenzazepines) and those in which A is sulfur (phenothiazines), and especially those of the third Subgroups in which R, R1 and R2 have the narrow meanings given above.  The following individual compounds are particularly preferred on account of their microbicidal action: N-cyclopropylcarbonyliminodibenzyl, ** WARNING ** End of CLMS field could overlap beginning of DESC **.