DE4210569A1 - Use of substd. beta-hydroxyethyl-amine(s0 - as fungicides effective against phytopathogenic fungi, e.g. phytophthora infestans and plasmopara vitcola - Google Patents

Abstract

Beta-hydroxyethylamine derivs. of formula (I) and their salts can be used as fungicides in the control of phytopathogenic fungi Aryl = Ph or naphthyl; R1 = H, 1-20C alkyl, 3-20C cycloalkyl, 2-20C alkenyl, Ph, phenyl (1-10C) alkyl, SiR8R9R10 or COR" (each Ph gp. being opt. mono, di or pref. tri-substd. with F, Cl, Br, C3, OH, SH, 1-20C alkyl, 3-20C cyclo-alkyl, 1-20C alkoxy, phenyl-7 and/or Ph); R2 and R3 = each H 1-20C alkyl, 2-20C alkenyl, 3-20C cyclo-alkyl 4 R4 and R5 = each H, 1-16C alkyl, 2-16C alkenyl, 3-20C cyclo-alkyl (opt. mono- or di-substd. with 1-4C alkyl, 1-4C alkoxy, CbF2b+1, F, Cl, Br and/or OH), 1-16C alkyl-Y R6 = H, 1-16C alkyl, 2-16C alkenyl, 1-16C alkyl-Y, 2-16C alkenyl-Y, Ph, phenyl-Y, benzyl, biphenylyl, F, Cl, Br, I, CcF2c+1, CCl3, naphthyl or YH; R7 = 1-20C alkyl, 2-20C alkenyl, 3-20C cycloalkyl, Ph, biphenylyl, phenoxyphenyl, benzylphenyl, etc. R8 = 1-10C alkyl, 2-10C alkenyl, 1-10C alkoxy, Pb, pentafluorophenyl or trityl; R9 and R10 = each 1-10C alkyl, 2-10C alkenyl, 1-10C alkoxy or Ph; R" = H, 1-20C alkyl, 2-20C alkenyl, 3-20C cyclo-alkyl, 1-20C alkyl-2-, 2-20C alkenyl-Z, 3-20C cycloalkyl-Z, Ph, phenyl-Z, phenyl-Y-phenyl-Z, phenyl(1-10C)alkyl, phenyl(1-10C)alkyl-Z or CaF2a+1; Y = O, S, SO or SO2; Z = NH, O or S; a and c = each 1-6; b = 1-4. USE/ADVANTAGE - (I), known to be effective against fungi, worms, algae, bacteria and protozoa (GB1109924, BE678973) are now found to have a fungicidal effect against phytopathogenic fungi, e.g. Plasmopara viticola, Phytophthora infestans, Pyrenophora teres and Botrytis cinerea.

Description

The invention relates to the use of substituted β-hydroxyethylamines and compositions containing such compounds as fungicidal active ingredients to combat phytopathogenic fungi.

Some substituted β-hydroxyethylamines are known. It is described Action against fungi, worms, algae, bacteria and protozoa (GB 11 09 924, BE 6 78 973). The use of the compounds as is not described fungicidal active ingredients to combat phytopathogenic fungi.

GB 11 09 924 describes bis-alkylamines with up to 5 carbon atoms in the alkyl radical, which is also substituted with phenyl or OH, the C atom carrying the OH group carries a hydrogen atom. The compounds are active against protozoa.

BE-PS 6 78 973 also relates to alkylamines with hydrogen on the β-C atom and with a variety of efficacies.

DE-A-34 22 918 describes N-acyl-β-hydroxyethylamines with particular pronounced acaricidal effects.

The task was to control active ingredients with fungicidal properties to find phytopathogenic mushrooms. It was solved by providing substituted β-hydroxyethylamines, which because of their pronounced fungicidal Effect are particularly well suited for the use mentioned.  

The invention therefore relates to the use of substituted β-hydroxyethylamines of the formula I and their salts,

in which
Aryl means phenyl or naphthyl,
R (1) hydrogen, (C₁-C₂₀) alkyl, (C₃-C₂₀) cycloalkyl, (C₂-C₂₀) alkenyl, phenyl, phenyl- (C₁-C₁₀) alkyl, SiR (8) R (9) R (10) or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or substituted one or more times, preferably up to three times, by identical or different radicals from the series fluorine, chlorine, bromine, CF₃, Hydroxy, mercapto, (C₁-C₂₀) alkyl, (C₃-C₂₀) cycloalkyl, (C₁-C₂₀) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, (C₁-C₆) alkoxy- (C₁-C₆) alkyl, phenyl- (C₁ -C₂₀) alkyl, phenyl- (C₂-C₂₀) alkenyl, 1-phenylcyclopropyl, phenylmercapto- (C₁-C₆) alkyl, phenoxy- (C₂-C₆) alkyl or diphenyl- (C₁-C₁₂) alkyl means , where phenyl in the abovementioned radicals is unsubstituted or substituted one or more times, preferably up to three times, by identical or different radicals from the series fluorine, chlorine, bromine, (C₁-C₁₆) alkyl, (C₃-C₁₆) - Cycloalkyl, hydroxy, mercapto, (C₁-C₁₆) alkoxy, phenyl, benzyl, phenethyl, phenylmercapto and C _a F _{2a + 1} , where two of these radicals can also be (C₁-C₄) alkylenedioxy;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning;
R (4) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₂₀) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, C _b F _{2b + 1} , fluorine, chlorine, bromine and hydroxy, (C₁-C₁₆) alkyl-Y, (C₂-C₁₆) alkenyl-Y, (C₃ -C₂₀) cycloalkyl-Y, phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, Bromine, iodine, C _c F _{2c + 1} , YH, naphthyl, CN or NO₂, where phenyl and naphthyl in the abovementioned radicals are unsubstituted or substituted by 1, 2 or 3 identical or different substituents from the series fluorine, chlorine , Bromine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (4) with R (5), in the event that the substituents are bound at adjacent positions on the phenyl ring, together a (CH₂) _p chain with p equal to 3 or 4, or a monounsaturated (C₃ or C₄) - Can form alkenediyl chain;
R (6) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₁-C₁₆) alkyl-Y, (C₂-C₁₆) alkenyl-Y, phenyl, phenyl-Y, benzyl, Biphenylyl, fluorine, chlorine, bromine iodine, C _c F _{2c + 1} , CCl₃, naphthyl or YH;
R (7) (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl, phenylmercaptophenyl, phenylsulfinylphenyl, phenylsulfonylphenyl, naphthyl, naphthyl 3,4-tetrahydronaphthyl, indanyl, fluorenyl, thienyl or furyl, where the ring systems mentioned are unsubstituted or substituted with 1-3 substituents which are the same or different and which are fluorine, chlorine, bromine, iodine, (C₁-C₂₀) -Alkyl, which is optionally substituted with 1 to 9 fluorine and / or chlorine atom, (C₃-C₂₀) -cycloalkyl, which optionally with one or two identical or different radicals from the series (C₁-C₄) -alkyl, (C₁- C₄) alkoxy, CF₃, fluorine, chlorine, bromine and hydroxy is substituted, (C₁-C₂₀) alkyl-Y, (C₃-C₂₀) -cycloalkyl-Y, which is optionally substituted as above cycloalkyl, (C₂-C₁₆) -Alkenyl, (C₂-C₁₆) alkenyl-Y, phenyl-Y, phenyl- (C₁-C₂) alkyl-Y, phenyl- (C₁-C ) -alkyl, biphenylyl, CN, NO₂, phenyloxycarbonyl, benzyloxycarbonyl, (C₁-C₁₆) alkoxycarbonyl or (C₂-C₁₆) alkenyloxycarbonyl, where phenyl is a constituent of the abovementioned radicals by 1, 2 or 3 identical or different radicals from the Series fluorine, chlorine, trifluoromethyl or hydroxy may be substituted;
R (8) is (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkoxy, phenyl pentafluorophenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, (C₁-C₂₀) alkyl-Z, (C₂-C₂₀) alkenyl-Z, (C₃-C₂₀) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₁₀) alkyl, phenyl- (C₁-C₁₀) alkyl-Z or C _a F _{2a +1} means;
Y represents oxygen, sulfur, sulfinyl or sulfonyl;
Z represents NH, oxygen or sulfur;
a is an integer from 1 to 6;
b is an integer from 1 to 4; and
c is an integer from 1 to 6,
as fungicidal active ingredients for combating phytopathogenic fungi.

In the above definitions and below, alkyl, alkenyl and residues derived therefrom, such as alkoxy, alkylmercapto, alkenyloxy and Alkenylmercapto, unless specifically stated otherwise, straight chain or branched. Alkenyl is mono- or polyunsaturated, Cycloalkyl is a mono-, bi- or multicyclic, preferably up to tricyclic  Rest, such as B. cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, decahydronaphthyl and adamantyl, where a cycloalkyl radical is also mono- or polyunsaturated, can be branched or unbranched.

Preference is given to using compounds of the formula I in which aryl is phenyl,
R (1) hydrogen, (C₁-C₁₆) alkyl, (C₃-C₁₆) cycloalkyl, (C₂-C₁₆) alkenyl, phenyl, phenyl- (C₁-C₈) alkyl, SiR (8) R (9) R (10) or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or polysubstituted, preferably up to triply, by identical or different radicals from the series fluorine, chlorine, CF₃, hydroxy, Mercapto, (C₁-C₁₆) alkyl, (C₃-C₁₆) cycloalkyl, (C₁-C₁₆) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, phenyl- (C₁ -C₁₆) alkyl, phenyl- (C₂-C₁₆) alkenyl, 1-phenylcyclopropyl, phenylmercapto- (C₁-C₄) alkyl, phenoxy- (C₂-C₆) alkyl or diphenyl- (C₁-C₁₀) alkyl means , where phenyl in the abovementioned radicals is unsubstituted or substituted one or more times, preferably up to three times, by identical or different radicals from the series, fluorine, chlorine, bromine, (C₁-C₁₂) alkyl, (C₃-C₁₂) -Cycloalkyl, hydroxy, mercapto, (C₁-C₁₂) alkoxy, phenyl, benzyl, phenethyl, phenylmercapto and C _a F _{2a + 1} , where two of these radicals can also be (C₁-C₄) alkylene dioxy;
R (3) is defined like R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₁₂) alkyl, (C₂-C₁₂) alkenyl, (C₃-C₁₆) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, C _b F _{2b + 1} , fluorine, chlorine, bromine and hydroxy, (C₁-C₁₂) alkyl-Y, (C₂-C₁₂) alkenyl-Y, (C₃ -C₁₆) cycloalkyl-Y, phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, C _c F _{2c + 1} , CCl₃, YH, naphthyl, CN or NO₂, where in the above radicals phenyl and naphthyl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents from the series fluorine, chlorine, bromine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (4) with R (5), in the event that the substituents are bound at adjacent positions on the phenyl ring, together a (CH₂) _p chain with p equal to 3 or 4, or a monounsaturated (C₃ or C₄) - Can form alkenediyl chain;
R (6) hydrogen, (C₁-C₁₂) alkyl, (C₂-C₁₂) alkenyl, (C₁-C₁₂) alkyl-Y, (C₂-C₁₂) alkenyl-Y, phenyl, phenyl-Y, benzyl, Biphenylyl, fluorine, chlorine, bromine C _c F _{2c + 1} , CCl₃, naphthyl or YH;
R (7) (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl, phenylmercaptophenyl, phenylsulfinylphenyl, phenylsulfonylphenyl, naphthyl, naphthyl 3,4-tetrahydronaphthyl, indanyl, fluorenyl, thienyl or furyl, where the ring systems mentioned are unsubstituted or substituted with 1-3 substituents which are the same or different and which are fluorine, chlorine, bromine, iodine, (C₁- C₁₆) -alkyl, which is optionally substituted with 1 to 6 fluorine and / or chlorine atoms, (C₃-C₁₆) -cycloalkyl, which optionally with one or two identical or different radicals from the series (C₁-C₄) -alkyl, ( C₁-C₄) alkoxy, CF₃, fluorine, chlorine and hydroxy is substituted, (C₁-C₁₆) alkyl-Y, (C₃-C₁₆) cycloalkyl-Y, which is optionally substituted as above cycloalkyl, (C₂-C₁₂) -Alkenyl, (C₂-C₁₂) -alkenyl-Y, phenyl-Y, phenyl- (C₁-C₂) -alkyl-Y, phenyl- (C₁-C₂) - alkyl, biphenylyl, CN, NO₂, phenyloxycarbonyl, benzyloxycarbonyl, (C₁-C₁₂) alkoxycarbonyl or (C₂-C₁₂) alkenyloxycarbonyl, where phenyl as a component of the above radicals by 1, 2 or 3 identical or different radicals from the series Fluorine, chlorine, trifluoromethyl or hydroxy can be substituted;
R is (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₁-C₈) alkoxy, phenyl, pentafluorophenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₁-C₈) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, (C₁-C₁₆) alkyl-Z, (C₂-C₁₆) alkenyl-Z, (C₃-C₁₆) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₈) alkyl, phenyl- (C₁-C₈) alkyl-Z or C _a F _{2a +1} means;
Y represents oxygen or sulfur;
Z represents NH, oxygen or sulfur;
a is an integer from 1 to 4;
b is an integer from 1 to 4; and
c is an integer from 1 to 6,

Particular preference is given to the use of compounds of the formula I in which
Aryl means phenyl;
R (1) hydrogen, (C₁-C₁₄) alkyl, (C₃-C₁₄) cycloalkyl, (C₂-C₁₄) alkenyl, phenyl, phenyl- (C₁-C₆) alkyl, SiR (8) R (9) R (10) or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or polysubstituted, preferably up to triply, by identical or different radicals from the series fluorine, chlorine, CF₃, hydroxy, Mercapto, (C₁-C₁₄) alkyl, (C₃-C₁₄) cycloalkyl, (C₁-C₁₄) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₁₄) cycloalkyl, (C₁-C₃) alkoxy- (C₁-C₃) alkyl, phenyl- (C₁ -C₁₄) -alkyl, phenyl- (C₂-C₁₄) -alkenyl, phenoxy- (C₂-C₃) -alkyl or diphenyl- (C₁-C₈) -alkyl means, where phenyl is unsubstituted or mono- or in the radicals mentioned above is substituted several times, preferably up to three times, by identical or different radicals from the series, fluorine, chlorine, CF₃, (C₁-C₈) alkyl, (C₃-C₈) cycloalkyl, hydroxy, (C₁-C₈) alkoxy, phenyl , Benzyl and phenethyl;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₂) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, CF₃, fluorine, chlorine and hydroxy, (C₁-C₁₀) alkyl-Y, (C₂-C₁₀) alkenyl-Y, (C₃-C₁₂) cycloalkyl-Y , Phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, CF₃ or YH, where in the above-mentioned radicals phenyl is unsubstituted or is substituted by 1, 2 or 3 identical or different substituents from the series fluorine, chlorine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (6) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkyl-Y, (C₂-C₁₀) alkenyl-Y, phenyl, phenyl-Y, benzyl, Is fluorine, chlorine, CF₃ or YH;
R (7) (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₂₀) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl or phenylmercaptophenyl, means, where the ring systems mentioned are unsubstituted or with 1-3 substituents which are the same or different are substituted, which are fluorine, chlorine, (C₁-C₁₂) alkyl, which is optionally substituted by 1 to 6 fluorine and / or chlorine atoms, (C₃-C₁₂) cycloalkyl, ( Are C₁-C₁₂) alkyl-Y, (C₃-C₁₂) cycloalkyl-Y, (C₂-C₁₀) alkenyl, (C₂-C₁₀) alkenyl-Y, phenyl-Y, benzyl-Y, benzyl or biphenylyl, where phenyl as a constituent of the abovementioned radicals can be substituted by 1, 2 or 3 identical or different radicals from the series fluorine, chlorine or trifluoromethyl;
R is (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy, phenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₁₄) cycloalkyl, (C₁-C₁₄) alkyl-Z, (C₂-C₁₄) alkenyl-Z, (C₃-C₁₄) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₆) alkyl, phenyl- (C₁-C₆) alkyl-Z or CF₃;
Y means oxygen or sulfur and
Z means NH or oxygen.

The use of compounds of the formula I in which
Aryl means phenyl;
R (1) hydrogen, (C₁-C₁₂) alkyl, (C₃-C₁₂) cycloalkyl, (C₂-C₁₂) alkenyl, phenyl, phenyl- (C₁-C₄) alkyl, SiR (8) R (9) R (10) or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or disubstituted by identical or different radicals from the series fluorine, chlorine, CF₃, (C₁-C₁₂) alkyl , (C₃-C₁₂) cycloalkyl, (C₁-C₁₀) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₀) cycloalkyl, phenyl- (C₁-C₆) alkyl, phenyl- (C₂-C₆) alkenyl, 2-phenoxyethyl or diphenyl- (C₁-C₆) alkyl means, where phenyl is unsubstituted or mono- or disubstituted in the abovementioned radicals by identical or different radicals from the series fluorine, chlorine, (C₁-C₈) alkyl , (C₃-C₈) cycloalkyl, (C₁-C₈) alkoxy, phenyl, benzyl and CF₃;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₃-C₁₀) cycloalkyl, (C₁-C₈) alkyl-Y, (C₂-C₈) alkenyl-Y, (C₃-C₈) -cycloalkyl-Y, phenyl, phenyl-Y, benzyl, benzyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine or CF₃ means, with phenyl being unsubstituted or substituted in the radicals mentioned above is with 1, 2 or 3 identical or different substituents from the series fluorine, chlorine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (6) represents hydrogen;
R (7) denotes (C₁-C₁₀) alkyl, (C₂-C₁₂) alkenyl, (C₃-C₁₂) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl or benzyloxyphenyl, the ring systems mentioned being unsubstituted or with 1-2 Substituents which are the same or different are substituted, which are fluorine, chlorine, (C₁-C₁₀) alkyl, (C₃-C₁₂) cycloalkyl, (C₁-C₁₂) alkyl-Y, (C₃-C₁₂) cycloalkyl- Y is (C₂-C₈) alkenyl, (C₂-C₈) alkenyl-Y, phenyl-Y, benzyl or biphenylyl;
R is (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy or phenyl;
R (9) and R (10) are the same or different and are (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₈) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₀) cycloalkyl, (C₁-C₁₀) alkyl-Z, (C₂-C₁₀) alkenyl-Z, Is (C₃-C₁₀) cycloalkyl-Z, phenyl, phenyl-Z, benzyl or benzyl-Z;
Y represents oxygen or sulfur; and
Z means NH or oxygen.

Examples of acceptable salt-forming acids are inorganic acids such as Hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, Phosphoric acid or nitric acid or organic acids such as malonic acid, Oxalic acid, gluconic acid, camphorsulfonic acid, benzenesulfonic acid, acetic acid, Propionic acid, p-toluenesulfonic acid or salicylic acid.

Those compounds that have at least one asymmetric carbon atom can occur as enantiomers and diastereomers. The invention includes both the use of the pure isomers and their Mixtures. Mixtures of diastereomers can be customary Methods, e.g. B. by selective crystallization from suitable solvents or by chromatography on silica gel or aluminum oxide in the components be separated.

Racemates can be separated into the enantiomers by customary methods be, e.g. B. by salt formation with an optically active acid, separation of diastereomeric salts and release of the pure enantiomers using a base. In addition, the enantiomers can also be prepared using chromatography separate chiral phases or by enzymatic means.

The compounds I used according to the invention are prepared by a compound of formula II

in which R (4), R (5), R (6) and R (7) have the meanings mentioned, with a Sulfur ylide of formula III

where p is zero or 1, to a compound of formula IV

implements
and then reacting the compound IV with a nucleophile of the formula MNR (2) R (3), in which R (2) and R (3) have the meanings mentioned and M is hydrogen or a metal equivalent, a compound I having R ( 1) = H is formed, which is isolated in the form of the free base or an acid addition salt.

To prepare the compound of formula I in a first Reaction step for the preparation of the compounds of formula IV a ketone Formula II in which R (4), R (5), R (6) and R (7) have the meanings given above have with a sulfur ylide of the formula III in an inert solvent, preferably dimethyl sulfoxide and tetrahydrofuran, or in mixtures of  Dimethyl sulfoxide with other inert solvents, e.g. B. tetrahydrofuran. When using a sulfur ylide of the formula (III) for which p = zero, a temperature range between -10 ° C and 50 ° C, preferably between 0 and 30 ° C appropriate; when using a sulfur ylide of the formula III, for which p = 1 is a temperature range between 0 and 80 ° C, preferably between 20 and 60 ° C.

The conversion of the intermediates of formula IV into the end products of Formula I with R (1) = H takes place in a second reaction step by reaction with a compound of the formula MNR (2) R (3), in which R (2), R (3) and M are the above have the meanings given.

The aforementioned implementation takes place in a temperature range of 20-160 ° C, optionally in an inert solvent.

Suitable solvents are, for example, N, N-dimethylformamide, N, N-dimethylacetamide, Dimethyl sulfoxide, sulfolane, N-methylpyrrolidone-2, dioxane, Tetrahydrofuran, acetonitrile, 4-methyl-2-pentanone, methanol, ethanol, Isopropyl alcohol, propanol, butanol, pentanol, tert-butyl alcohol, methyl glycol, Methylene chloride or an aromatic hydrocarbon such as benzene, chlorobenzene, Nitrobenzene, toluene or xylene or water. Mixtures of solvents mentioned by way of example can be used.

Suitable bases are, for example, alkali metal or alkaline earth carbonates, hydrogen carbonates, hydroxides, alcoholates or hydrides such as. B. Sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, Sodium methylate or sodium hydride.

The implementation of the compounds of formula II with the compounds of the formula III to the intermediates of formula IV and implementation of these with those of Formula MNR (2) R (3) to compounds of formula I with R (1) = H can also in One-pot procedures are carried out.  

To do this, first, as stated above, implement a Compound of formula II with a compound of formula III a solution of a Compound of formula IV in one of the inert solvents given above forth. Then at least an equivalent amount is added to this solution a compound of the formula HNR (2) R (3).

Compounds of formula I in which R (1) has the meanings mentioned and is not equal to H, are produced by methods known from the literature.

Production of raw materials

Compounds of the formula II are commercially available or known from the literature or can be obtained from commercially available starting materials can be produced according to literature regulations.

The compounds of formula I used according to the invention are notable for an excellent fungicidal effect. Already in the plant tissue invaded fungal pathogens can be successfully curated fight. This is particularly important and beneficial in such fungal diseases, no longer after infection with the usual fungicides can be effectively combated. The spectrum of effects of the claimed Compounds covers a variety of different economically significant, phytopathogenic fungi, such as B. Plasmopara viticola, Phytophthora infestans, Pyrenophora teres and Botrytis cinerea.

The compounds of the invention are also suitable for use in technical areas, for example as wood preservatives, as Preservatives in paints, in cooling lubricants for the Metalworking or as a preservative in drilling and cutting oils.

The invention also relates to agents which in addition to the compounds of formula I. contain suitable formulation aids. The agents according to the invention generally contain from 1 to 95% by weight of the active compounds of the formula I.  

They can be formulated in different ways, depending on how it is done by the biological and / or chemical-physical parameters is specified. As Formulation options are therefore possible: wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), Suspoemulsions (SC), dusts (DP), pickling agents, granules in the form of water-dispersible granules (WG), ULV formulations, microcapsules, Wax or bait.

These individual formulation systems are known in principle and are described, for example, in:
Winnacker-Küchler, "Chemical Technology", Volume 7, C-Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker NY, 2nd Ed. 1972-73; K. Martens, "Spray-Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carrier", 2nd Ed., Darland Books, Caldwell NJ; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley, NY; March, Solvents Guide, 2nd Ed., Interscience, NY 1950; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with others can also be made pesticidal substances, fertilizers and / or growth regulators produce, e.g. B. in the form of a finished formulation or as a tank mix.  

Pointed powders are preparations that are evenly dispersible in water. In addition to the active ingredient, they contain wetting agents such as a diluent or an inert substance. B. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenolsulfonates and dispersants, for. B. sodium lignosulfonate, 2,2'- dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleylmethyl tauric acid sodium. Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. The following can be used as emulsifiers:
Alkylarylsulfonic acid calcium salts such as Ca.-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide-sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays such as kaolin, bentonite, poryhillite or Diatomaceous earth. Granules can either by spraying the active ingredient adsorbable, granulated inert material are produced or by Applying active ingredient concentrates by means of adhesives, e.g. B. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinite or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - granulated.

The active ingredient concentration in wettable powders is e.g. B. about 10 to 90 wt .-% of The remainder to 100 wt .-% consists of conventional formulation components. At emulsifiable concentrates, the active ingredient concentration can be about 5 to 80% by weight be. Dust-like formulations usually contain 5 to 20% by weight. At Granules, the active ingredient content depends in part on whether the effective  Connection is liquid or solid and which connection is liquid or solid and which granulation aids, fillers, etc. are used.

In addition, the active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetration, solvent, Fillers or carriers.

The concentrates available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water.

Dusty and granulated preparations as well as sprayable solutions usually not diluted with other inert substances before use.

With the external conditions such as temperature, humidity and. a. varies the required application rate. It can fluctuate within wide limits, e.g. B. between 0.005 and 10.0 kg / ha or more of active substance, preferably it is however between 0.01 and 5 kg / ha.

The active compounds according to the invention can be in their commercially available formulations either alone or in combination with other fungicides known from the literature be applied.

Fungicides known from the literature, which according to the invention can be combined with the compounds of the formula I, are, for. B. to name the following products:
Anilazines, Benalaxyl, Benodanil, Benomyl, Binapacryl, Bitertanol, Buthiobat, Captafol, Captan, Carbendazim, Carboxin, CGD-94240F, Chlobenzthiazone, Chlorthalonil, Cymoxanil, Cyproconazole, Cyprofuram, Dichlofluanol, Dichlofluanol, Dichlofluanol, Dichlofluanid, Dichl Diniconazole, Dinocap, Dithianon, Dodemorph, Dodine, Edifenfos, Ethirimol, Etridiazol, Fenarimol, Fenfuram, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetate, Fentinhydroxide, Fluaziram, Fluobenzimine, Fluoride, Flutolazolazole, Flutriazolazole, Flusriazolazole, Flusriazolazole Furmecyclox, Guazatine, Hexaconazole, Imazalil, Iprobefos, Iprodione, Isoprothiolane, copper compounds such as Cu-oxychloride, Oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepronil, Metalaxyl, Methasulfocarb, Methfuroxam, Myclobutanil, Nabamyl, Nuuralhalarololidol, Nitrothalyl, Nitrothalo, Nitrothal Oxadixyl, oxycarboxin, penconazole, pencycuron, PP 969, probenazole, probineb, prochloraz, procymidon, propamocarb, prop iconazol, prothiobarb, pyracarbolide, pyrifenox, pyroquilon, rebenzazole, sulfur, tebuconazole, thiabendazole, thiofanatemethyl, thiram, tolclofos-methyl, tolylfluanid, traidimefon, triadimenol, tricyclazole, tridemorph, trififorodoline, sodium, trififorodoline, trififorodoline, sodium, triflorodoline, sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, cetyl trimethyl ammonium chloride, salts of long-chain primary, secondary or tertiary ethylenediamine, methyl aminomethane, methyl aminomethane, methyl aminomethane, methyl aminomethane, aminomethyl aminyl aminomethane, aminomethyl aminyl aminophenyl aminomethane, aminophenyl aminomethyl aminyl aminophenyl aminomethane ammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline.

The above-mentioned combination partners are known active ingredients that are used for large part in CH. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7th ed. (1983), British Crop Protection Council.

In addition, the active ingredient according to the invention in its commercially available Formulations as well as those prepared from these formulations Application forms in a mixture with other active ingredients, such as other fungicides, Insecticides, attractants, sterilants, acaricides, nematicides or herbicides available. Insecticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, formamidines, tin compounds Microorganisms manufactured substances u. a.

Preferred mix partners are:  

1. From the group of phosphorus compounds

Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, Demeton, Demeton-S-methyl, Demeton-S-methyl sulfphone, Dialifos, Diazinon, dichlorvos, dicrotophos, O, O-1,2,2,2- tetrachloroethylphosphorthioate (SD 208 304), dimethoate, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenaminphos, Fenitriothion, Fensulfothion, Fenthion, Fonofos, Formothion, Heptenophos, Isozophos, Isothioates, isoxathion, malathion, methacrifos, methamidophos, methidation, Salithion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemetonmethyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosfolan, Phosmet, Phosphamidon, Phoxim, Pirimiphos-ethyl, Pirimiphosmethyl, Profenofos, Propaphos, Proetamphos, Prothiofos, Pyraclofos, Pyridapenthion, Quinalphos, Sulprofos, Temephos, Terbufos, Tetrachlorvinphos, thiometone, triazophos, trichlorphone, vamidothione;

2. From the group of carbamates

Aldicarb, 2-sec.-butylphenylmethylcarbamate (BPMC), carbaryl, carbofuran, Carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, Isoprocarb, methomyl, 5-methyl-m-cu-menyl-butyryl (methyl) carbamate, Oxamyl, primicarb, propoxur, thiodicarb, thiofanox, ethyl-4,6,9-triaza-4- benzyl-6, 10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1- Methylthio (ethylidenamino) -N-methyl-N- (morpholinothio) carbamate (UC 51 717);

3. From the group of carboxylic acid esters

Allethrin, alphamethrin, 5-benzyl-3-furylmethyl- (E) - (1R) -cis-2,2-dimethyl-3- (2- oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bioallethrin, Bioallethrin ((S) -cyclopentyl isomer), bioresmethrin, biphenates, (RS) -1-cyano- 1- (6-phenoxy-2-pyridyl) methyl (1RS) trans-3- (4-tert-butylphenyl) -2-, 2- dimethyl-cyclopropanecarboxylate (NCI 85 193), cycloprothrin, cyfluthrin, Cyhalothrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin,  Esfenvalerate, Fenfluthrin, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, fluvalinate (D-isomer), permethrin, pheothrin, ((R) -isomer), d- Pralethrin, pyrethrin (natural products), resmethrin, tefluthrin, Tetramethrin, tralomethrin.

4. From the amidine group

Amitraz, chlorordime form.

5. From the group of tin compounds Cyhexatin, fenbutatin oxides. 6. Other

Abamectin, Bacillus thuringiensis, Bensultap, Binapacyl, Bromopropylate, Buprofezin, Camphechlor, Cartap, Chlorbenzialate, Chlorfluazuron, 2- (4- Chlorophenyl) -4,5-diphenylthiophene (UBI-T 930), chlororfentezine, Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromazine, N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl -) - 2-chloro ethyl benzcarboximidate, DDT, dicofol, N- (N- (3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), Diflubenzuron, N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidenes) -2,4-xylidines, Dinobuton, Dinocap, Endosulfan, Ethofenprox, (4-Ethoxyphenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) silane, 4-ethoxyphenyl- (3- (4-fluoro-3- phenoxyphenyl) propyl) dimethylsilane, fenoxycarb, 2-fluoro-5- (4- (4- ethoxyphenyl) -4-methyl-1-pentyl) diphenyl ether (MTI 800), granulosic and Nuclear polyhedron viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, Gamma-HCH, hexythiazox, hydramethylnon (AC 217 300), ivermectin, 2- Nitromethyl-4,5-dihydro-6H-thiazine (SD 52 618), 2-nitromethyl-3,4- dihydrothiazole (SD 35 651), 2-nitromethylene-1,2-thiazinan-3- ylcarbamaldehyde (WL 108 477), propargite, teflubenzuron, tetradifone, Tetrasul, thicyclam, triflumarone.  

The active substance content of those prepared from the commercially available formulations Forms of use can vary widely, ie active substance concentration the use forms can be from 0.0001 to 100% by weight of active compound, are preferably between 0.001 to 1% by weight. The application happens in a usual way adapted to the application forms.

The following examples serve to explain the invention.

A. Examples of formulation

• a) A dusting agent is obtained by adding 10 parts by weight of active ingredient and 90 Mixes parts by weight of talc as an inert substance and crushed them in a hammer mill.
• b) A wettable powder which is readily dispersible in water is obtained by 25 parts by weight of active ingredient, 65 parts by weight of kaolin-containing quartz as Inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight oleoylmethyltauric acid sodium as a wetting and dispersing agent and grinds in a pin mill.
• c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of one Sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid Sodium salt and 51 parts by weight of water and in one Grinding ball mill ground to a fineness of less than 5 microns.
• d) An emulsifiable concentrate can be prepared from 15 parts by weight Active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight Share oxyethylated nonylphenol (10 AeO) as an emulsifier.  
• e) Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or Quartz sand. A suspension of the is expediently used Spray powder from Example b) with a solids content of 30% and sprayed these onto the surface of an attapulgite granulate, dry and mix intimate. The proportion by weight of the wettable powder is about 5% and of the inert carrier material approx. 95% of the finished granulate.

Examples of the compounds of formula I used according to the invention are in the following table is compiled without the invention on the there mentioned connections would be limited.

Biological examples Example 1: Plasmopara viticola

Wine seedlings of the "Riesling / Ehrenfelder" varieties were grown about 6 weeks after the Sowing with aqueous suspensions of the claimed compounds to runoff treated. After the spray coating had dried on, the plants were washed with a Zoosporangia suspension of Plasmopara viticola inoculated and dripping wet for 4-5 h in a climate chamber with 23 ° C and 80-90% rel. Humidity set.

After an incubation period of 7 days in the greenhouse, the plants placed again in the climatic chamber overnight to sporulate the fungus to stimulate. The infestation was then assessed. The degree of infestation was in % infected leaf area compared to the untreated, 100% infected Control plants expressed.

At 500 mg active ingredient / l spray mixture, the following substances show complete suppression of the infection:
Table Ex .: 1, 2, 5, 6, 8, 10, 11, 12, 14, 15, 16, 17, 18, 19, 22, 24, 25, 26, 27, 28, 29, 31.

Example 2: Phytophthora infestans

Tomato plants of the "Rheinlands Ruhm" variety were in the 3-4 leaf stage aqueous suspensions of the claimed compounds evenly dripping wet wetted. After drying, the plants were treated with a zoosporangia Suspension of Phytophthora infestans inoculated and for 2 days under optimal Infection conditions kept in a climatic chamber. After that, the Plants cultivated in the greenhouse until symptoms develop. The Infestation was assessed approximately 1 week after inoculation. The degree of infestation of the plants were in% affected leaf area compared to the untreated, 100% infected control plants.  

At 500 mg active ingredient / l spray mixture, the following substances show complete suppression of the infection:
Example table: 2, 3, 4, 5, 6, 17, 19, 22, 23.

Example 3: Botrytis cinerea

Approx. 14 day old beans of the varieties "Herz Freya" or "Frank's Ackerperle" were dripping wet with aqueous suspensions of the claimed compounds treated. After the spray coating had dried on, the plants were washed with a Spore suspension (1.5 million spores / ml) of Botrytis cinerea inoculated. The Plants were grown in a climatic chamber at 20-22 ° C and approx. 99% rel. Humidity cultivated further. The infection of the plants manifests itself in the formation of black ones Stains on leaves and stems. The evaluation of the tests took place approx. 1 Week after inoculation. The degree of infestation of the plants increased as a percentage untreated, 100% infected control plants rated.

At 500 mg active ingredient / l spray mixture, the following compounds show complete suppression of infestation:
Table Ex .: 1, 2, 3, 5, 6, 11, 12, 14, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26, 27, 28, 29, 30, 31 .

Example 4: Pyrenophora teres

Barley plants of the "Igri" variety were grown in the 2-leaf stage with an aqueous Suspension of the claimed compounds treated to runoff. After this The plants were dried with an aqueous spray coating Spore suspension of Pyrenophora teres and inoculated for 16 h in one Climate chamber at 100% rel. Humidity incubated. Then the infected plants in the greenhouse at 25 ° C and 80% rel. Humidity cultivated further. Approx. The infestation was evaluated 1 week after inoculation and the Degree of infestation in% affected leaf area compared to untreated, 100% infected control plants rated.  

At 500 mg active ingredient / l spray mixture, the following substances show complete suppression of the infection:
Table Ex .: 1, 2, 3, 4, 5, 6, 7, 9, 11, 13, 18, 19, 25, 26, 28, 29.

Claims (9)

1. Use of a compound of the formula I and its salts, in which
Aryl means phenyl or naphthyl,
R (1) hydrogen, (C₁-C₂₀) alkyl, (C₃-C₂₀) cycloalkyl, (C₂-C₂₀) alkenyl, phenyl, phenyl- (C₁-C₁₀) alkyl, SiR (8) R (9) R (10), or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or polysubstituted, preferably up to triply, by identical or different radicals from the series fluorine, chlorine, bromine, CF₃ , Hydroxy, mercapto, (C₁-C₂₀) alkyl, (C₃-C₂₀) cycloalkyl, (C₁-C₂₀) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, (C₁-C₆) alkoxy- (C₁-C₆) alkyl, phenyl- (C₁ -C₂₀) alkyl, phenyl- (C₂-C₂₀) alkenyl, 1-phenylcyclopropyl, phenylmercapto- (C₁-C₆) alkyl, phenoxy- (C₂-C₆) alkyl or diphenyl- (C₁-C₁₂) alkyl means , where phenyl in the abovementioned radicals is unsubstituted or substituted one or more times, preferably up to three times, by identical or different radicals from the series fluorine, chlorine, bromine, (C₁-C₁₆) alkyl, (C₃-C₁₆) - Cycloalkyl, hydroxy, mercapto, (C₁-C₁₆) alkoxy, phenyl, benzyl, phenethyl, phenylmercapto and C _a F _{2a + 1} , where two of these radicals can also be (C₁-C₄) alkylenedioxy;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning;
R (4) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₂₀) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, C _b F _{2b + 1} , fluorine, chlorine, bromine and hydroxy, (C₁-C₁₆) alkyl-Y, (C₂-C₁₆) alkenyl-Y, (C₃ -C₂₀) - cycloalkyl-Y, phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, Bromine, iodine, C _c F _{2c + 1} , CCl₃, YH, naphthyl, CN or NO₂ means, wherein in the above radicals phenyl and naphthyl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents from the fluorine series , Chlorine, bromine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (4) with R (5), in the event that the substituents are bound at adjacent positions on the phenyl ring, together a (CH₂) _p chain with p equal to 3 or 4, or a monounsaturated (C₃ or C₄) - Can form alkenediyl chain;
R (6) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₁-C₁₆) alkyl-Y, (C₂-C₁₆) alkenyl-Y, phenyl, phenyl-Y, benzyl, Biphenylyl, fluorine, chlorine, bromine, iodine, C _c F _{2c + 1} , CCl₃, naphthyl or YH;
R (7) (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl, phenylmercaptophenyl, phenylsulfinylphenyl, phenylsulfonylphenyl, naphthyl, naphthyl 3,4-tetrahydronaphthyl, indanyl, fluorenyl, thienyl or furyl, where the ring systems mentioned are unsubstituted or substituted with 1-3 substituents which are the same or different and which are fluorine, chlorine, bromine, iodine, (C₁-C₂₀) -Alkyl, which is optionally substituted with 1 to 9 fluorine and / or chlorine atom, (C₃-C₂₀) -cycloalkyl, which optionally with one or two identical or different radicals from the series (C₁-C₄) - alkyl, (C₁- C₄) alkoxy, CF₃, fluorine, chlorine, bromine and hydroxy is substituted, (C₁-C₂₀) alkyl-Y, (C₃-C₂₀) -cycloalkyl-Y, which is optionally substituted as above cycloalkyl, (C₂-C₁₆) -Alkenyl, (C₂-C₁₆) -alkenyl-Y, phenyl-Y, phenyl- (C₁-C₂) -alkyl-Y, phenyl- (C₁ -C₂) alkyl, biphenylyl, CN, NO₂, phenyloxycarbonyl, benzyloxycarbonyl, (C₁-C₁₆) alkoxycarbonyl or (C₂-C₁₆) - alkenyloxycarbonyl, where phenyl is a constituent of the abovementioned radicals by 1, 2 or 3 identical or different radicals can be substituted from the series fluorine, chlorine, trifluoromethyl or hydroxy;
R (8) represents (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkoxy, phenyl, pentafluorophenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₂₀) alkyl, (C₂-C₂₀) alkenyl, (C₃-C₂₀) cycloalkyl, (C₁-C₂₀) alkyl-Z, (C₂-C₂₀) alkenyl-Z, (C₃-C₂₀) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₁₀) alkyl, phenyl- (C₁-C₁₀) alkyl-Z or C _a F _{2a + 1} means;
Y represents oxygen, sulfur, sulfinyl or sulfonyl;
Z represents NH, oxygen or sulfur;
a is an integer from 1 to 6;
b is an integer from 1 to 4, and
c is an integer from 1 to 6,
as fungicidal active ingredients for combating phytopathogenic fungi. 2. Use according to claim 1, in which
Aryl phenyl means
R (1) hydrogen, (C₁-C₁₆) alkyl, (C₃-C₁₆) cycloalkyl, (C₂-C₁₆) alkenyl, phenyl, phenyl- (C₁-C₈) alkyl, SiR (8) R (9) R (10), or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or polysubstituted, preferably up to triple, by identical or different radicals from the series fluorine, chlorine, CF₃, hydroxy , Mercapto, (C₁-C₁₆) alkyl, (C₃-C₁₆) cycloalkyl, (C₁-C₁₆) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, phenyl- (C₁ -C₁₆) alkyl, phenyl- (C₂-C₁₆) alkenyl, 1-phenylcyclopropyl, phenylmercapto- (C₁-C₄) alkyl, phenoxy- (C₂-C₄) alkyl or diphenyl- (C₁-C₁₀) alkyl means , where phenyl in the abovementioned radicals is unsubstituted or substituted one or more times, preferably up to three times, by identical or different radicals from the series, fluorine, chlorine, bromine, (C₁-C₁₂) alkyl, (C₃-C₁₂) -Cycloalkyl, hydroxy, mercapto, (C₁-C₁₂) alkoxy, phenyl, benzyl, phenethyl, phenylmercapto and C _a F _{2a + 1} , where two of these radicals can also be (C₁-C₄) alkylene dioxy;
R (3) is defined like R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₁₂) alkyl, (C₂-C₁₂) alkenyl, (C₃-C₁₆) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, C _b F _{2b + 1} , fluorine, chlorine, bromine and hydroxy, (C₁-C₁₂) alkyl-Y, (C₂-C₁₂) alkenyl-Y, (C₃ -C₁₆) - cycloalkyl-Y, phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, C _c F _{2c + 1} , CCl₃, YH, naphthyl, CN or NO₂, where in the above radicals phenyl and naphthyl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents from the series fluorine, chlorine, bromine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (4) with R (5), in the event that the substituents are bound at adjacent positions on the phenyl ring, together a (CH₂) _p chain with p equal to 3 or 4, or a monounsaturated (C₃ or C₄) - Can form alkenediyl chain;
R (6) hydrogen, (C₁-C₁₂) alkyl, (C₂-C₁₂) alkenyl, (C₁-C₁₂) alkyl-Y, (C₂-C₁₂) alkenyl-Y, phenyl, phenyl-Y, benzyl, Biphenylyl, fluorine, chlorine, bromine, C _c F _{2c + 1} , CCl₃, naphthyl or YH;
R (7) (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl, phenylmercaptophenyl, phenylsulfinylphenyl, phenylsulfonylphenyl, naphthyl, naphthyl 3,4-tetrahydronaphthyl, indanyl, fluorenyl, thienyl or furyl, where the ring systems mentioned are unsubstituted or substituted with 1-3 substituents which are the same or different and which are fluorine, chlorine, bromine, iodine, (C₁-C₁₆) -Alkyl, which is optionally substituted with 1 to 6 fluorine and / or chlorine atoms, (C₃-C₁ -C) cycloalkyl, which optionally with one or two identical or different radicals from the series (C₁-C₄) - alkyl, (C₁- C₄) alkoxy, CF₃, fluorine, chlorine and hydroxy is substituted, (C₁-C₁₆) - alkyl-Y, (C₃-C₁₆) -cycloalkyl-Y, which is optionally substituted as above cycloalkyl, (C₂-C₁₂) -alkenyl , (C₂-C₁₂) alkenyl-Y, phenyl-Y, phenyl- (C₁-C₂) -alkyl-Y, phenyl- (C₁-C ) -alkyl, biphenylyl, CN, NO₂, phenyloxycarbonyl, benzyloxycarbonyl, (C₁-C₁₂) alkoxycarbonyl or (C₂-C₁₂) alkenyloxycarbonyl, where phenyl is a constituent of the abovementioned radicals by 1, 2 or 3 identical or different radicals from the Series fluorine, chlorine, trifluoromethyl or hydroxy may be substituted;
R is (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₁-C₈) alkoxy, phenyl, pentafluorophenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₁-C₈) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₆) alkyl, (C₂-C₁₆) alkenyl, (C₃-C₁₆) cycloalkyl, (C₁-C₁₆) alkyl-Z, (C₂-C₁₆) alkenyl-Z, (C₃-C₁₆) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₈) alkyl, phenyl- (C₁-C₈) alkyl-Z or C _a F _{2a +1} means;
Y represents oxygen or sulfur;
Z represents NH, oxygen or sulfur;
a is an integer from 1 to 4;
b is an integer from 1 to 4; and
c is an integer from 1 to 6. 3. Use according to claim 1 or 2, in which
Aryl means phenyl;
R (1) hydrogen, (C₁-C₁₄) alkyl, (C₃-C₁₄) cycloalkyl, (C₂-C₁₄) alkenyl, phenyl, phenyl- (C₁-C₆) alkyl, SiR (8) R (9) R (10), or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or polysubstituted, preferably up to triple, by identical or different radicals from the series fluorine, chlorine, CF₃, hydroxy , Mercapto, (C₁-C₁₄) alkyl, (C₃-C₁₄) cycloalkyl, (C₁-C₁₄) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₁₄) cycloalkyl, (C₁-C₃) alkoxy- (C₁-C₃) alkyl, phenyl- (C₁ -C₁₄) -alkyl, phenyl- (C₂-C₁₄) -alkenyl, phenoxy- (C₂-C₃) -alkyl or diphenyl- (C₁-C₈) -alkyl means, where phenyl is unsubstituted or mono- or in the radicals mentioned above is substituted several times, preferably up to three times, by identical or different radicals from the series fluorine, chlorine, CF₃, (C₁-C₈) alkyl, (C₃-C₈) cycloalkyl, hydroxy, (C₁-C₈) alkoxy, phenyl, Benzyl, phenethyl;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₂) cycloalkyl, which is unsubstituted or substituted by one or two identical or different radicals from the series (C₁- C₄) alkyl, (C₁-C₄) alkoxy, CF₃, fluorine, chlorine and hydroxy, (C₁-C₁₀) alkyl-Y, (C₂-C₁₀) alkenyl-Y, (C₃-C₁₂) cycloalkyl-Y , Phenyl, phenyl-Y, phenyl- (C₁-C₂) -alkyl, phenyl- (C₁-C₂) -alkyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, CF₃ or YH, where in the above-mentioned radicals phenyl is unsubstituted or is substituted by 1, 2 or 3 identical or different substituents from the series fluorine, chlorine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (6) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₁-C₁₀) alkyl-Y, (C₂-C₁₀) alkenyl-Y, phenyl, phenyl-Y, benzyl, Is fluorine, chlorine, CF₃ or YH;
R (7) denotes (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₂₀) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl, benzyloxyphenyl or phenylmercaptophenyl, the ring systems mentioned being unsubstituted or with 1 -3 substituents, which are identical or different, are substituted, which are fluorine, chlorine, (C₁-C₁₂) -alkyl, which is optionally substituted by 1 to 3 fluorine and / or chlorine atoms, (C₃-C₁₂) -cycloalkyl, ( Are C₁-C₁₂) alkyl-Y, (C₃-C₁₂) cycloalkyl-Y, (C₂-C₁₀) alkenyl, (C₂-C₁₀) alkenyl-Y, phenyl-Y, benzyl-Y, benzyl or biphenylyl, where phenyl as a constituent of the abovementioned radicals can be substituted by 1, 2 or 3 identical or different radicals from the series fluorine, chlorine or trifluoromethyl;
R is (C₁-C₈) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy, phenyl or trityl;
R (9) and R (10) are the same or different and are (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₄) alkyl, (C₂-C₁₄) alkenyl, (C₃-C₁₄) cycloalkyl, (C₁-C₁₄) alkyl-Z, (C₂-C₁₄) alkenyl-Z, (C₃-C₁₄) cycloalkyl-Z, phenyl, phenyl-Z, phenyl-Y-phenyl-Z, phenyl- (C₁-C₆) alkyl, phenyl- (C₁-C₆) alkyl-Z or CF₃;
Y means oxygen or sulfur and
Z means NH or oxygen. 4. Use according to any one of claims 1 to 3, in which
Aryl means phenyl;
R (1) hydrogen, (C₁-C₁₂) alkyl, (C₃-C₁₂) cycloalkyl, (C₂-C₁₂) alkenyl, phenyl, phenyl- (C₁-C₄) alkyl, SiR (8) R (9) R (10), or CO-R (11) means, where phenyl in the abovementioned radicals is unsubstituted or mono- or disubstituted by identical or different radicals from the series fluorine, chlorine, CF₃, (C₁-C₁₂) - Alkyl, (C₃-C₁₂) cycloalkyl, (C₁-C₁₀) alkoxy, phenyl-Y or phenyl;
R (2) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₀) cycloalkyl, phenyl- (C₁-C₆) alkyl, phenyl- (C₂-C₆) alkenyl, 2-phenoxyethyl or diphenyl- (C₁-C₆) alkyl means, where phenyl is unsubstituted or mono- or disubstituted in the abovementioned radicals by identical or different radicals from the series fluorine, chlorine, (C₁-C₈) alkyl , (C₃-C₈) cycloalkyl, (C₁-C₈) alkoxy, phenyl, benzyl and CF₃;
R (3) is defined as R (2), where R (2) and R (3) each have the same or different meaning and R (2) and R (3) cannot simultaneously be hydrogen;
R (4) hydrogen, (C₁-C₈) alkyl, (C₂-C₈) alkenyl, (C₃-C₁₀) cycloalkyl, (C₁-C₈) alkyl-Y, (C₂-C₈) alkenyl-Y, (C₃-C₈) -cycloalkyl-Y, phenyl, phenyl-Y, benzyl, benzyl-Y, phenyl-Y-phenyl-Y, biphenylyl, fluorine, chlorine, or CF₃, wherein phenyl is unsubstituted in the radicals mentioned above or is substituted with 1, 2 or 3 identical or different substituents from the series fluorine, chlorine and CF₃;
R (5) is defined as R (4), where R (4) and R (5) are the same or different;
R (6) represents hydrogen;
R (7) denotes (C₁-C₁₀) alkyl, (C₂-C₁₂) alkenyl, (C₃-C₁₂) cycloalkyl, phenyl, biphenylyl, phenoxyphenyl, benzylphenyl or benzyloxyphenyl, the ring systems mentioned being unsubstituted or with 1-2 Substituents which are the same or different are substituted, which are fluorine, chlorine, (C₁-C₁₀) alkyl, (C₃-C₁₂) cycloalkyl, (C₁-C₁₂) alkyl-Y, (C₃-C₁₂) cycloalkyl- Y is (C₂-C₈) alkenyl, (C₂-C₈) alkenyl-Y, phenyl-Y, benzyl or biphenylyl;
R is (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy or phenyl;
R (9) and R (10) are the same or different and are (C₁-C₆) alkyl, (C₂-C₆) alkenyl, (C₁-C₆) alkoxy or phenyl;
R (11) hydrogen, (C₁-C₁₀) alkyl, (C₂-C₁₀) alkenyl, (C₃-C₁₀) cycloalkyl, (C₁-C₁₀) alkyl-Z, (C₂-C₁₀) alkenyl-Z, Is (C₃-C₁₀) cycloalkyl-Z, phenyl, phenyl-Z, benzyl or benzyl-Z;
Y represents oxygen or sulfur; and
Z means NH or oxygen. 5. Fungicidal compositions containing at least one fungicidally effective amount a compound of formula I according to any one of claims 1 to 4 together with the auxiliaries and additives customary for this application. 6. Plant protection products containing a fungicidally effective amount at least one compound of formula I according to one of claims 1 to 4 and at least one further active ingredient, preferably from the series of fungicides, Insecticides, attractants, sterilants, acaricides, nematicides and herbicides together with the auxiliaries and additives customary for this application. 7. Agents for use in wood protection or as a preservative in Paints, in cooling lubricants for metalworking or in drilling and Cutting oils containing an effective amount of at least one compound of the Formula I according to any one of claims 1 to 4 together with those for this Applications usual auxiliaries and additives. 8. Use of a compound of formula I according to one of the Claims 1 to 4 as wood preservatives or as preservatives in Paints, in cooling lubricants for metalworking or in drilling and Cutting oils. 9. A method of combating phytopathogenic fungi, thereby characterized in that one looks at this or the plants infested by them, Surfaces or substrates a fungicidally effective amount of a compound of the formula I applied according to claims 1 to 4.