| Title of Invention | NOVEL PHENYL-PROPARGYLETHER DERIVATIVES |
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| Abstract | The invention relates to phenyl-propargylether derivatives of general formula (I) including the optical isomers thereof and mixtures of such isomers, wherein R¿1? is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R¿2? and R¿3? are each independently hydrogen or alkyl, R¿4? is alkyl, alkenyl or alkynyl, R¿5? R¿6?, R¿7?, and R¿8? are each independently hydrogen or alkyl, R¿9? is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, R¿10? is optionally substituted aryl or optionally substituted heteroaryl, and Z is halogen, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted arylthio, optionally substituted alkylthio, optionally substituted alkenylthio, optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenylsulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl or optionally substituted alkynylsulfonyl. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi. |
| Full Text | Novel Phenvl-Proparqylether DeR1vatives The pR6sent invention R6lates to novel phenyl-propaR9ylether deR1vatives of formula I bol: •. It R6lates to the pR6paR8tion of those substances and to agrochemical compositions ccR11r sing at least one of those compounds as active ingR6dient. The invention R6lates also tc ' pR6paR8tion of the said compositions and to the use of the compounds or of the compc: i tions in controlling or pR6venting the infestation of plants by phytopathogenic micrcoR9a nisms, especially fungi. substituted alkynyl, R10 is optionally substituted aryl or optionally substituted heteroaryl, and Z is halogen, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted arylthic optionally substituted alkylthio, optionally substituted alkenylthio, optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenylsulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl or optionally substituted alkynylsulfonyl. In the above definition aryl includes aromatic hydrocarbon R1ngs like phenyl, naphthyl, anthR8cenyl, phenanthR6nyl and biphenyl like 1,3-biphenyl and 1,4-biphenyl, with phen>' being pR6ferR6d. The same definition applies wheR6 aryl is part of aryloxy or arylthio. Heteroaryl stands for aromatic R1ng systems compR1sing mono-, bi- or tR1cyclic systems wheR6in at least one oxygen, nitrogen or sulfur atom is pR6sent as a R1ng member. Examples aR6 furyl, thienyl, pyrrolyl, imidazolyl, pyR8zolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, tR1azolyl, tetR8zolyl, pyR1dyl, pyR1dazinyl, pyR1midinyl, pyR8zinyl, tR1azinyl, tetR8zinyl, indolyl, benzothiophenyl, benzofuR8nyl, benzimidazolyl, indazolyl, benzotR1azolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quin-oxalinyl, quinazolinyl, cinnolinyl and naphthyR1dinyl. The above aryl and heteroaryl groups may be optionally substituted. This means that they may carry one or moR6 identical or diffeR6nt substituents. Normally not moR6 than thR6e substituents aR6 pR6sent at the same time. Examples of substituents of aryl or heteroaryl groups aR6: alkyl, alkenyl. alkynyl, cycloaikyl, cycloalkyl-aikyl, phenyl and phenyl-alkyl, it being possible in tuR11 for all of the pR6ceding groups to carry one or moR6 identical or diffeR6nt halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy, alkylthio; haloalkylthio; aikylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycar-bonyl. Typical examples include 4-chlorophenyl, 4-bromophenyl, 3,4-dichlorophenyl, 4-chioro-3-fluorophenyl, 3-chloro-4-fluorophenyl, 4-methylphenyl, 4-ethylphenyl, 4-propar-gyloxyphenyl, 1-naphtyl, 2-naphtyl, 4-biphenylyl, 4'-chloro-4-biphenylyl, 5-chloro-thien2-yl, 5-methyl-thien-2-yl, 5-methyl-fur-2-yl, 5,6,7,8-tetR8hydro-1-naphthyl, 5,6,7,8-tetR8hydro-2-naphthyl, 3,4-dioxomethylenyl-phenyl, 3,4-dioxoethylenyl-phenyl, 6-benzothienyl, 7-benzo-thienyl, 3-methylphenyl, 4-fluorophenyl, 4-ethenylphenyl, 4-ethynylphenyl, 4-propylphenyl, 4-isopropylphenyl, 4-tert.butylphenyl, 4-ethoxyphenyl, 4-ethynyloxyphenyl, 4-phenoxyphe-nyl, 4-methylthiophenyl, 4-methylsulfonylphenyl, 4-cyanophenyl, 4-nitrophenyl, 4-meth-oxycarbonyl-phenyl, 3-bromophenyl, 3-chlorophenyl, 2-chloropheny!, 2,4-dichlorophenyl, 3,4,5-tR1chlorophenyl, 3,4-difluorophenyl, 3,4-dibromophenyl, 3,4-dimethoxyphenyl, 3,4-di-methylphenyl, 3-chIoro-4-cyanophenyl, 4-chloro-3-cyanophenyl, 3-bromo-4-methylphenyl, 4-methoxy-3-methylphenyl, 3-fiuoro-4-methoxyphenyl, 4-chloro-3-methylphenyl, 4-chloro-3-tR1fluoromethyl-phenyl, 4-bromo-3-chlorophenyl, 4-tR1fluoromethylphenyl, 4-tR1fluorome-thoxyphenyl, 4-methoxyphenyl, 4'-methyl-4-biphenylyl, 4'-tR1fluoromethyl-4-biphenylyl, 4'-bromo-4-biphenylyl, 4'-cyano-4-biphenylyl, 3'4'-dichIoro-4-biphenylyl, etc. Again, the same optional substituent may be pR6sent wheR6 aryl is part of aryloxy or arylthio. Optionally substituted alkyl, alkenyl or alkynyl groups may carry one or moR6 substituents selected from halogen, alkyl, alkoxy, alkylthio, cycloaikyl, phenyl, nitro, cyano, hydroxy, mercapto, alkylcarbonyl or alkoxycarbonyl. This also applies wheR6 alkyl, alkenyl or alkynyl is part of another substituent like alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenylyoxy, alkenylthio, alkenylsulfinyl, alkenylsufonyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl. PR6feR8bly, the number of substituents is no moR6 than thR6e with the exception of halogen, wheR6 the alkyl groups may be perhalogenated. In the above definitions -halogen- includes fluoR1ne, chloR1ne, bromine and iodine. The alkyl, alkenyl and alkynyl R8dicals may be stR8ight-chain or bR8nched. This applies also to the alkyl, alkenyl or alkynyl parts of other alkyl-, alkenyl- or alkynyl-containing groups. Depending upon the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be undeR9tood as being, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the isomeR9 theR6of, for example isopropyl, isobutyl, tert-butyl or sec-butyl, isopentyl or tert-pentyl. Cycloalkyl is, depending upon the number of carbon atoms mentioned, cyclopropyl, cyclo-butyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Depending upon the number of carbon atoms mentioned, alkenyl as a group or as a structuR8l element of other groups is to be undeR9tood as being, for example, ethenyl, aliyl, 1-propenyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl, 4-methyl-3-pentenyl or 4-methyl-3-hexenyl. Alkynyl as a group or as a structuR8l element of other groups is, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl, 1-ethyl-2-butynyl or octyn-1-yl. A haloalkyl group may contain one or moR6 (identical or diffeR6nt) halogen atoms, and for example may stand for CHCI2, CH2F, CCI3, CH2CI, CHF2, CF3, CH2CH2Br, C2CI5, CHsBr, CHCIBr, CF3CH2. etc.. The pR6sence of at least one asymmetR1c carbon atom in the compounds of formula I means that the compounds may occur in optically isomeR1c and enantiomeR1c forms. As a R6sult of the pR6sence of a possible aliphatic C=C double bond, geometR1c isomeR1sm may also occur. Formula I is intended to include all those possible isomeR1c forms and mixtuR6s theR6of. PR6ferR6d subgroups of compounds of formula I aR6 those wheR6in R1 is hydrogen, alkyl, cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by substituents selected from the group compR1sing alkyl, alkenyl. alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may in turn be substituted by one or several halogens; alkoxy; alkenyloxy; alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; or Ri is hydrogen, C1-C8 alkyl, Ca-CBcycloalkyl. phenyl or naphthyl; phenyl and naphthyl being optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C1-C8 alkylsulfonyl, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; or R1 is hydrogen, C1-C8 alky! or phenyl optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloaikylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; or Ri is hydrogen, C1-C8 alkyl or Cs-CBcycloalkyl; or Ri is hydrogen or C1-C4 alkyl; or R2 and R3 are independently of each other hydrogen or C1-C4 alkyl; or R2 and R3 are hydrogen; or R4 is C1-C8 alkyl, C2-C8alkenyl, or C2-C8 alkynyl; or R4 is C1-C6 alkyl; or R4 isC1-C4alkyl, or R4 is methyl or ethyl, especially methyl; or R5, R6, R7 and Ra are independently of each other hydrogen or C1-C4 alkyl; or R5, R6 and R7 are hydrogen and Rs is hydrogen, methyl or ethyl, preferably methyl; or R5, Ret R7 and Rs are hydrogen; or R9 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4alkenyl or C3-C4alkynyl; or R9 is hydrogen or C1-C4 alkyl; or R9 is hydrogen; or Rio is aryl or heteroaryl, each optionally substituted with substituents selected from the group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may be substituted with one or more halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl and alkynyloxycarbonyl; or R10 is phenyl, naphthyl or biphenyl, each optionally substituted by one to thR6e substituents selected from the group compR1sing C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfonyl, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; or R10 is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to thR6e substituents selected from the group compR1sing C1-C8alkyl, C1-C8 haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8 alkylthio, C1-C8haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; or Z is halogen, optionally substituted aryloxy or arylthio wheR6in in each the aryl may be optiortally substituted by one or moR6 substituents selected from the group compR1sing halogen, C1-C8alkoxy, C3-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C8 alkoxy-C1-C8alkyl, C1-C8 halo-alkoxy, C1-C8alkylthio, C1-C8 haioalkylthio, C1-C8 alkylsulfonyl, fomiyl, C2-Caalkanoyl, hydroxy, halogen, cyano, nitro, amino. C1-C8 alkylamino, di-C1-C8 alkylamino, carboxyl and C1-C8al-koxycarbonyl; or is optionally substituted C1-C8alkoxy, optionally substituted C2-C8alkenyl-oxy, optionally substituted C2-C8 alkynyloxy, optionally substituted C1-C8 alkylthio, optionally substituted C2-C8alkenylthio, optionally substituted C2-C8alkynylthio, optionally substituted C1-C8 alkylsulfinyj, optionally substituted C2-C8alkenylsulfinyl, optionally substituted C2-C8al-kynylsulfinyl, optionally substituted C1-C8 alkylsulfonyl, optionally substituted C2-C8alkenyl-sulfonyl or optionally substituted C2-Caalkynylsulfonyl wheR6in each alkyl, alkenyl or alkynyl group may carry one or moR6 substituents selected from the group compR1sing halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C2-C6cycloalkyl, nitro, cyano, hydroxy, phenyl, mercapto, C1-C4 alkylcarbonyl and C1-C4 alkoxycarbonyl; or Z is halogen; C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8alkynyloxy, C1-C8 alkoxy-C1-C8 alkoxy, C2-C8alkenyloxy-Ci-C8alkoxy, C2-Caalkynyloxy-C1-C8 alkoxy, C1-C8haloalkoxy, C2-C8 cyclo-alkyl-C1-C8 alkoxy, C1-C8alkylthio, C2-Caalkenylthio, C2-C8aIkynylthio, C1-C8 haloalkylthio, C2-C8 cycloalkyl-C1-C8alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C2-C8alkenylsuifinyl, C2-Caalkenylsulfonyl, C2-Caalkynylsulfinyl or C2-C8alkynylsulfonyl; or Z is halogen; C1-C8 alkoxy, C2-C8alkenyloxy, C3-C8 alkynyloxy, C1-C8 alkoxy-C1-C8 alkoxy, C2-C8alkenyloxy-C1-C8 alkoxy, C2-C8alkynyloxy-C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C8 cycloikyl-C1-C8 alkoxy, C1-C8 alkylthio, C2-C8alkenylthio, C2-Caalkynylthio, C1-C8 haloalkylthio or C2-C8 cycloalkyl-C1-C8alkylthio; or Z is halogen; C1-C8 alkoxy, C2-C8alkenyloxy, C2-C6alkynyloxy, C1-C4alkoxy-C1-C2alkoxy, C1-C8alkylthio, C2-C8 alkenylthio or C2-C8alkynylthio; or Z is C1-C8alkoxy, C2-C6alkenyloxy or C2-C6alkynyloxy. One preferred subgroup of the compounds of formula I consists of those compounds wherein R+ is hydrogen, and Z is C1-C8alkoxy, C2-C6alkenyloxy or C3-C8alkynyloxy. Further preferred subgroups are those wherein Ri is hydrogen, alkyl, cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by substituents selected from the group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may in turn be substituted by one or several halogens; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; and R4 is alkyl; and R10 is aryl or heteroaryl, each optionally substituted by substituents selected from to group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloal-kyl-alkyl, phenyl and phenylalkyl, where all these groups may be substituted by one or several halogen; alkoxy; alkenyloxy; alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl and alkynyloxycarbonyl; and Z is C1-C8alkoxy, C2-C6a!kenyloxy or C2-C6alkynyloxy ; or Ri is hydrogen, C1-C8alkyl, C3-C8cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by one to three substituents selected from the group comprising C1-C8alkyl, C3-C8alkenyl, C2-C8 alkynyl, C1-C8haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfonyl, halogen, cyano, nitro and C1-C8al-koxycarbonyl; and R2, R3, R5, Re, and R7 are hydrogen; and R4 and Rs are independently C1-C8alkyl; and R10 is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C1-C8alkyl, Ca-Caalkenyl, C2-C8alkynyl, Ci-C8haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfonyl, halogen, cyano, nitro and C1-C8alkoxycarbonyl; and R9 is hydrogen or C1-C4 alkyl; and Z is C1-C8alkoxy, C2-C6alkenyloxy or C2-C6alkynyloxy; or Ri is hydrogen, C1-C8alkyl, phenyl optionally substituted by one to three substituents selected from the group comprising C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, C1-C8haloal-koxy, C1-C8alkylthio, C1-C8haloalkylthio, halogen, cyano, nitro and C1-C8alkoxycarbonyl; and R2, R3, R5, R6, and R7 are hydrogen; and R4 and R8 are each independently methyl or ethyl; and R10 is phenyl, naphthyl. 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C1-C8alkyl, d-Cahaloalkyl, C1-C8al- koxy, C-C8 haloalkoxy, C1-C6 alkylthio, C-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 al-koxycarbonyl; R9 is hydrogen and Z is C1-C8 alkoxy, C2-C6 alkenyloxy or C2-C6 alkynyloxy. Other preferred subgroups of the compounds of formula I are those wherein Ri is hydrogen, alkyl, cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by substituents selected from the group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may in turn be substituted by one or several halogens; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; and R2 and R3 are independently of each other hydrogen or C1-C4alkyl; and R4 is C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; and R5, R6, R7 and R8 are independently of each other hydrogen or C1-C4alkyl; and R9 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl orC3-C4alkynyl; and Rio is aryl or heteroaryl, each optionally substituted with substituents selected from to group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may be substituted with one or more substituents selected from the group comprising halogen; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl and alkynyloxycarbonyl; and Z is halogen, optionally substituted aryloxy or arylthio wherein in each the aryl may be optionally substituted by one or more substituents selected from the group comprising halogen, C1-C8 alkoxy, C2-C8alkenyloxy, C2-C8 alkynyloxy, CrCBalkoxy-C-C8 alkyl, C-C8 halo-alkoxy, C1-C8 alkylthio, C-C8 haloalkylthio, C1-C6 alkylsulfonyl, formyl, C2-C8alkanoyl, hydroxy, halogen, cyano, nitro, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, carboxyl and C1-C8al-koxycarbonyl; or is optionally substituted C1-C6 alkoxy, optionally substituted C2-Caalke-nyloxy, optionally substituted C2-C8alkynyloxy, optionally substituted C1-C6 alkylthio, optionally substituted C2-C8 alkenylthio, optionally substituted C2-C8alkynylthio, optionally substituted C1-C8 alkylsulfinyl, optionally substituted C2-Caalkenylsulfinyl, optionally substituted C2-C8alkynylsulfinyl, optionally substituted C-C8 alkylsulfonyl, optionally substituted C2-C8 alkenylsulfonyl or optionally substituted C2-C8alkynylsulfonyl wherein each alkyl, alkenyl or alkynyl group may carry one or more substituents selected from the group compR1sing halogen, C1-C4 alkyl, C1-C4 alkoxy, alkylthio, C2-C6cycloalkyl, nitro, cyano, hydroxy, phenyl, mercapto, C1-C4 alkylcarbonyl and C1-C4 alkoxycarbonyl; or wheR6in R1 is hydrogen, C1-C8alkyI, C3-C8 cycioalkyI, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by one to thR6e substituents selected from the group compR1sing C1-C8aikyI, C3-C8 alkenyl, C2-C8 alkynyl, C1-C8haioalkyl, C1-C8 alkoxy, C1-C8haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C1-C8 alkylsulfonyl, halogen, cyano, nitro and C1-C8 al-koxycarbonyl; and R2 and R3 aR6 hydrogen; and R4 is C1-C6alkyI; and R5, R6 and R7 aR6 hydrogen and R8 is hydrogen, methyl or ethyl, pR6feR8bly methyl; and R9 is hydrogen or C1-C4 alkyl; and R10 is phenyl, naphthyl or biphenyl, each optionally substituted by one to thR6e substituents selected from the group compR1sing C1-C8alkyI, C3-C8 alkenyl, C3-C8 alkynyi, C1-C8haloalkyI, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C1-C8alkylsulfonyl, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is halogen; C1-C8 alkoxy, C3-C8 alkenyloxy, C1-C8alkynyloxy, C1-C8 alkoxy-C1-C8 alkoxy, C2-CBalkenyIoxy-Ci-C8alkoxy, C3-C8 alkynyloxy-C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 cyclo-alkyl-C1-C8 alkoxy, C1-C8 alkylthio, Cg-Cealkenylthio, C1-C8 alkynylthio, C1-C8 haloalkylthio, C2-C8 cycloalkyl-C1-C8 alkylthio, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl. C2-C8 alkenylsulfinyl, C2-C8aikenylsulfonyl, C2-C8 alkynylsulfinyl or C2-C8alkynylsulfony!; or wheR6in R1 is hydrogen, C1-C8 alkyl or phenyl optionally substituted by one to thR6e substituents selected from the group compR1sing C1-C8alkyI, C1-C8 haloalkyI, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and R2 and R3 aR6 hydrogen; and R4 is C1-C4 alkyl, and R5, R6 and R7 aR6 hydrogen and R8 is hydrogen or methyl; and R9 is hydrogen; and R10 is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one-to thR6e substituents selected from the group compR1sing C1-C8 alkyl, C1-C8 haloalkyI, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is halogen; C1-C8 alkoxy, C2-Caalkenyloxy, C2-C8alkynyloxy. C1-C4 alkoxy-Ci-C2alkoxy, C2-C8 alkylthio, C2-C8alkenylthio or C2-Caalkynylthio; or wheR6in R1 is hydrogen, C1-C8 alkyl or C2-C8 CycloalkyI; and R2, R9. R5, R6, R7, R9 and R9 aR6 hydrogen; and R4 is methy! or ethyl; and R10 is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to thR6e substituents selected from the group compR1sing aikyl, C1-C8halioalkyl, C1-C8alkoxy, C1-C8haloaikoxy, C1-C8aJkylthio, Ci-Cehaloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is C1-C8alkoxy, C2-C6alkenyloxy or C2-C6alkynyloxy. PR6ferR6d individual compounds aR6: 2-(4-bromO'phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-chloro-2-(4-chioro-phenyl)'N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-chioro-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-bromo-phenyl)-2-methoxy-N-[2-{3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyi]-acetamide, 2-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyioxy-phenyl)-ethyl]-acetamide, 2-(3,4-dichloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyIoxy-phenyl)-ethyl]-acetamide, 2-(4-chloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(3,4-dichloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy'4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide. 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy- acetamide, 2-(4-bromo-phenyi)-2-cyclopropylmethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyi)-ethyI]- acetamide, 2-(4-chloro-phenyl)-2-cyclopropylmethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-cyclopropylmethoxy-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyioxy-phenyl)- ethylj-acetamide, 2-(4-bromo-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-chloro-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyI]- acetamide, 2-(3,4-dichloro-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethy acetamide, 2-allyloxy-2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-allyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-allyloxy-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyI)-ethyl]- acetamide, 2-(4-bromo-phenyl)-2-(but-2-enyloxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(but-2-enyloxy)-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl^^ acetamide, 2-(but-2-enyloxy)-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide. 2-(4-chloro-phenyl)-N-[2-{3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-biphenyl-4-yl-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-naphthalen-2-yl-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-2-p-tolyl-acetamide, 2-(4-ethyl-phenyI)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop--2-ynyloxy-phenyl)-ethyt]-2-prop-2-ynyloxy-2-(4-tR1fluoromethyl- phenyl)-acetamide, 2-(4-bromo-phenyl)-2-but-2-ynyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-but-2-ynyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-but-2-ynyloxy-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynylsulfanyl- acetamide, 2-(4-chloro-phenyl)-N-[2-(3-R11ethoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynylsulfanyi- acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynylsulfanyl-acetamide, 2-allylsulfanyl-2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-allylsulfanyl-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-allylsulfanyl-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethy acetamide, 2-(4-bromo-phenyl)-N-[2-{3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4-chloro-phenyl)-N-[2-{3-methoxy-4-penl-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-R11ethoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyi)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(3,4-difluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4"Chloro-3"fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynyloxy-acetamide, and 2-(3-chloro-4-fiuoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyIoxy-phenyl)-ethyl]-2-prop-2- ynyloxy-acetamide. Certain mandelic acid deR1vatives have been proposed for controlling plant-destructive fungi (for example in WO 94/29267 and in WO 96/17840). The action of those pR6paR8tions is not. however, satisfactory in all aspects of agR1cultuR8l needs. SurpR1singly, with the compound structuR6 of formula I, new kinds of microbiocides having a high level of activity have been found. The propaR9ylether deR1vatives of formula I and displayed subformulae and intermediates may be obtained according to one of the processes of Schemes 1 to 4: wheR6in R4, R5. R6, R7 and R6 aR6 as defined for formula I, optionally in the pR6sence of a base and optionally in the pR6sence of a diluting agent. Carboxy-activated deR1vatives of the acid of formula II aR6 all compounds having an activated carboxyl group like an acid halide, such as an acid chloR1de, like symmetR1cal or mixed anhydR1des, such as mixed anhydR1des with O-alkylcarbonates, like activated esteR9, such as p-nitrophenylesteR9 or N-hydroxysuccinimidesteR9, as well as in-situ-formed activated forms of the amino acid of formula II with condensating agents, such as dicyclohexylcarbodiimide, carbonyldiimidazole, benzotR1azol-1 -yloxy-tR1s(dimethylamino)- phosphonium hexafluorophosphate, O-benzotR1azol-l-yl N,N,N\N'-bis(pentamethylene)-uronium hexafluorophosphate, O-benzotR1azol-1-yl N,N,N\N'-bis(tetR8methylene)uronium hexafluorophosphate, O-benzotR1azol-1-yl N,N,N',N'-tetR8methyluronium hexafluorophosphate or benzotR1azol-1-yloxy-tR1pyrrolidinophosphonium hexafluorophosphate. The mixed anhydR1des of the acids of the formula II may be pR6paR6d by R6action of an amino acid of formula II with chloroformic acid esteR9 like chloroformic acid alkylesteR9, such as ethyl chloroformate or isobutyl chloroformate, optionally in the pR6sence of an oR9anic or inoR9anic base like a tertiary amine, such as tR1ethylamine, N,N-diisopropyl-ethylamine, pyR1dine, N-methyl-pipeR1dine or N-methyl-morpholine. The pR6sent R6action is pR6feR8bly performed in a solvent like aromatic, non-aromatic or halogenated hydrocarbons, such as chlorohydrocarbons e.g. dichloromethane or toluene; ketones e.g. acetone; esteR9 e.g. ethyl acetate; amides e.g. N,N-dimethylformamide; nitR1les e.g. acetonitR1le; or etheR9 e.g. diethylether, tert-butyl-methylether, dioxane or tetR8hydro-fuR8ne or water. It is also possible to use mixtuR6s of these solvents. The R6action is performed optionally in the pR6sence of an oR9anic or inoR9anic base like a tertiary amine, e.g. tR1ethylamine, N,N-diisopropyl-ethylamine, pyR1dine, N-methyl-pipeR1dine or N-methyl-morpholine, like a metal hydroxide or a metal carbonate, pR6feR6ntially an alkali hydroxide or an alkali carbonate, such as lithium hydroxide, sodium hydroxide or potassium hydroxide at tempeR8tuR6s R8nging from -80°C to +150°C, pR6feR6ntially at tempeR8tuR6s R8nging from -40°C to +40°C. Step B: The compounds of formula I may then finally be pR6paR6d by R6acting a phenol of formula IV wheR6in R4, R5. R6, R7. R9, R9, R10 and Z aR6 as defined for formula ! with a compound of formula V wheR6in R1, R2 and R3 aR6 as defined for formula I and wheR6in Y is a leaving group like a halide such as a chloR1de or bromide or a sulfonic ester such as a tosylate, mesylate ortR1flate. The R6action is advantageously performed in a solvent like aromatic, non-aromatic or halogenated hydrocarbons, such as chlorohydrocarbons e.g. dichloromethane or toluene; ketones e.g. acetone or 2-butanone; esteR9 e.g. ethyl acetate; etheR9 e.g. diethylether, tert-butyl-methyjether, dioxane or tetrihydrofuR8ne, amides e.g. dimethylformamide, nitR1les e.g. acetonitR1le, alcohols e.g. methanol, ethanol, isopropanol, n-butanol or tert-butanol, sulfoxides e.g. dimethylsulfoxide or water. It is also possible to use mixtuR6s of these solvents. The R6action is performed optionally in the pR6sence of an oR9anic or inoR9anic base like a tertiary amine, such as tri1ethylamine, N,N-diisopropyl-ethylamine, pyR1dine, N-methyl-piperidine or N-methy!-morpholine, like a metal hydroxide, a metal carbonate or a metal alkoxide, pR6feR6ntially an alkali hydroxide, an alkali carbonate or an alkali alkoxide, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, sodium tert-butoxide or potassium tert-butoxide at tempeR8tuR6s R8nging from -80°C to +200°C, pR6feR6ntially at tempeR8tuR6s R8nging from 0°C to +120°C. step D: A compound of formula VII wheR6in R4, R5, R6, R7 and R8 aR6 as defined for formula I is alkylated with a compound of formula V (see Scheme 1) wheR6in R1, R2, R3 and Y aR6 as defined for Scheme 1 under the same conditions as defined for step B in Scheme 1. Step E: A compound of formula VIII wheR6in R1, R2, R3, R4, R5, R6, R7 and R9 aR6 as defined for formula I is dehydR8ted to an isocyanide of formula IX wheR6in R1, R2, R3, R4, R5, R6, R7 and R8 aR6 as defined for formula I under conditions known per se (D. Seebach, G. Adam, T. Gees, M. Schiess, W. Weigang, Chem. Ben 1988, 121, 507). Step F: An isocyanide of formula IX wheR6in R1, R2, R3, R4, R5, R6, R7 and R9 aR6 as defined for formula I is R6acted in a thR6e-component PasseR1ni R6action (J. March, Advanced OR9anic Chemistry, 4th ed., Wiley, 1992, p. 980) with an aldehyde or ketone of formula X, wheR6in R9 and R10 aR6 as defined for formula I in the pR6sence of a carboxylic acid XI wheR6in R11 is hydrogen or lower alkyl, typically acetic acid, to give a 0-acyl-α-hydroxy amide of formula XII, wheR6in R1, R2, R3. R4, R9, R6, R7, R9, R9 and R10 aR6 as defined for formula I. Step G: AlteR11atively to step F, an isocyanide of formula IX wheR6in R1, R2, R3, R4, R5, R6, R7 and R6 aR6 as defined for formula I is R6acted with an aldehyde or ketone of formula X in the pR6sence of titanium tetR8chloR1de to give an a-hydroxy amide of the formula XIII (wheR6 R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the same meaning as defined above) under conditions known per se (D. Seebach, G. Adam, T. Gees, M. Schiess, W. Weigang, Chem. Ber. 1988, 121, 507; O. Ort, U. Doller, W. R6issel, S. D. Lindell, T. L Hough, D. J. Simpson, J. P. Chung, Pesticide Sci, 1997, 50, 331). Step H: AlteR11atively to step F and step G, a compound of fomnula VIII, wheR6in R1, R2, R3, R4, R5, R6, R7 and R8 aR6 as defined for formula I is tR6ated with one phosgene equivalent (e.g. tR1phosgene) and a base (e.g. tR1ethylamine) and in a second step, without isolation of the isocyanide intermediate, is further tR6ated with titanium tetR8chloR1de and an aldehyde or ketone of formula X, wheR6in R9 and R10 as defined for formula I under conditions known per se (WO 96/17840) to give an a-hydroxy amide of the formula XIII, wheR6in R1, R2, R3, R4, R5, R6, R7, R6, R9 and R10 aR6 as defined for formula I. step I: An 0-acyl-a-hydroxy amide of formula XII wherein R1, R2, R3, R4, R5, R6. R7, R8, R9, R10 and R11 are as defined above is hydrolyzed to a an aα-hydroxy amide of formula XIII, wherein R1, R2, R3, R4, R5, R6. R7, R8. R9 and R10 are as defined for formula I under classical conditions (J. March, Advanced OR9anic Chemistry, 4th ed., Wiley, 1992). Step K: An a-hydroxy amide of formula XIII wherein R1, R2, R3. R4. R5. Re, R7. R8, R9 and R;o are as defined for formula I is reacted with a compound XIV wherein R12 is alkyl, alkenyl or alkynyl and Y is a leaving group like a halide such as a chloR1de or bromide or a sulfonic ester such as a tosylate, mesylate or tR1flate to a compound of formula la wherein R1, R2, R3, R4. R5, R6, R7, R8. R9 and R10 are as defined for formula I and R12 is alkyl, alkenyl or alkynyl under the same conditions as defined for step B in Scheme 1. Step L: An a-substituted amide of formula XVI wherein R1, R2, R3. R4. R5. Re, R7, R8. R9 and R10 are as defined for formula I and Y is a leaving group like a halide such as a chloR1de or bromide or a sulfonic ester such as a tosylate, mesylate or tR1flate, is reacted with a compound XV wherein R12 is alkyl, alkenyl or alkynyl to a compound of formula la wherein R1, R2, R3, R4, R5, Re, R7, Re, R9 and R10 are as defined for formula I and R12 is alkyl, alkenyl or alkynyl under the same conditions as defined for step B in Scheme 1. Step LA: The compound of subformula la, wherein R1, R2, R3, R4, R5. Re, R7, Re, R9 and R10 are as defined for formula I and R12 is alkyl, alkenyl or alkynyl may also be prepared by reacting a compound of formula XVIa wherein R1, R2, R3, R4, R9. Re, R7, Re, R9 and R10 are as defined for formula I and Y is a leaving group like a sulfonic ester such as a tosylate, mesylate or tR1flate with a compound of formula XV, wherein R12 is alkyl, alkenyl or alkynyl under conditions known per se (R. V. Hoffmann, J. OR9, Cham. 1995, 60, 7043). The reaction is performed optionally in the presence of an oR9anic base like a tertiary amine, such as tR1ethylamine, N,N-diisopropyi-ethylamine, pyR1dine, N-methyl-pipeR1dine or N-me-thyl-morpholine at tempeR8tures R8nging from -80°C to +200X, preferentially at tempeR8tures R8nging from 0°C to +120°C. step M: A dioxolanone XVII (obtained by the condensation of a mandelic acid with acetone under acid catalysis (see EP-A-071568) is subsequently treated with a base such as lithium diisopropylamide (LDA) and an alkylating agent R9-Y wherein R9 is alkyl and Y is a leaving group like a halide such as a chloride or bromide or a sulfonic ester such as a tosylate, mesylate ortrifiate, according to known procedures (F. Cavelier, S. Gomez, R. Jacquier, J. Verducci, Tetrahedron Lett. 1994, 2891, DE 4319887). Steps N, O and P: The resulting dioxolanone XVIII is either heated with the appropriate amine VI at temperatures in between 50-200°C (step O), or the dioxolanone is first hydrolysed in aqueous diluted mineral acid (e.g. HCI) or under basic conditions (aqueous sodium hydroxide (0-120°C; step N) to the substituted hydroxy acid XIX which then can be amidated (step P, according to step A, scheme 1). Hydroxy acids XIX can also be obtained by reaction of a Grignard reagent R10-MgHal (starting from an aryl-halide and Mg) with an appropriate a-keto acid ester (A. F. Hegarty, P. O'Neill, Synf/?es/s 1993, 606). Step Q: A ketone of formula XXIII, wherein R10 is as defined for formula I, is chlorinated to give a dichloroketone of formula XXV, wherein R10 is as defined for formula I, under conditions known per se (J. G. Aston, J. D. Newkirk, D. M. Jenkins, J. Dorsky, Org. Synth. Coll. VO/. 3, 1955, 538). Step R: A dichloroketone of formula XXV, wherein R10 is as defined for formula I, is reacted with an inorganic base such as sodium hydroxide or potassium hydroxide to give a a-hydroxy acid of formula XlXa, wherein R10 is as defined for formula I, under conditions known per se (J. G. Aston, J. D. Newkirk, D. M. Jenkins, J. Dorsky, Org. Synth. Coll. Vol. 3, 1955,538). Step S: A α-hydroxy acid of formula XlXa, wherein R10 is as defined for formula I is reacted with a mineral acid such as sulfuric acid, hydrochloric acid or nitric acid and a ketone of formula XXVii, wherein R' and R" are alkyl to give a dioxolanone XVIIa, wherein R10 is as defined for formula I and R' and R" are alkyl. Step T: A dioxolanone of formula XVIIa, wherein Rio is as defined for formula I and R' and R" are alkyl is reacted with an amine of formula XX, wherein R4 is as defined for formula I in the presence of a base, such as triethylamine, N,N-diisopropyl-ethylamine, pyridine, N-me-thyl-piperidine, N-methyl-morpholine, potassium carbonate or sodium carbonate at temperatures ranging from -80°C to +200°C, preferentially at temperatures ranging from 0°C to 120°C to give a compound of formula XXI, wherein R4 and R10 are as defined for formula I. Step U: A compound of formula XXI, wherein R4 and R10 are as defined for formula I, is reacted with a compound of formula XXII, wherein Y is a leaving group like a halide such as chlorine or bromine or a sulfonic ester group such as a tosylate, mesylate or triflate, under phase-transfer alkylation conditions in the presence of an inorganic base such as sodium hydroxide or potassium hydroxide and a phase-transfer catalyst like benzyltriethylammo-nium chloride or tetrabutylammonium bromide to obtain a compound of formula lb, wherein R4 and R10 are as defined for formula I. Step V: An aldehyde of formula XXIV, wherein R10 is as defined for formula I, is reacted with an inorganic cyanide, like sodium cyanide or potassium cyanide, in the presence of an inorganic sulfite, such as sodium bisulfite or potassium bisulfite to obtain a cyanohydrin of formula XXVI, wherein R10 is as defined for formula I, under conditions known per se (B. B. Corson. R. A. Dodge, S. A. Harris, J, S. Yeaw, Org. Synth, ColL Vol, 1,1941, 336). Step W: A cyanohydrin of formula XXVI, wherein R10 is as defined for formula I, is reacted with a mineral acid, such as sulfuric acid, hydrochloric acid or nitric acid to yield a a-hydroxy acid of formula XlXa, wherein Rio is as defined for formula I, under conditions known per se (B. B. Corson, R. A. Dodge, S. A. Harris, J. S. Yeaw, Org, Synth. ColL Vol. 1, 1941, 336). The compounds of formula I are oils or solids at room temperature and are distinguished by valuable microbiocidal properties. They can be used in the agricultural sector or related fields preventatively and curatively in the control of plant-destructive microorganisms. The compounds of formula I according to the invention are distinguished at low rates of concentration not only by outstanding microbiocidal, especially fungicidal, activity but also by being especially well tolerated by plants. Surprisingly, it has now been found that the compounds of formula I have for practical purposes a very advantageous microbiocidal spectrum in the control of phytopathogenic microorganisms, especially fungi. They possess very advantageous curative and preventive properties and are used in the protection of numerous crop plants. With the compounds of formula I it is possible to inhibit or destroy phytopathogenic microorganisms that occur on various crops of useful plants or on parts of such plants (fruit, blossom, leaves, stems, tubers, roots), while parts of the plants which grow later also remain protected, for example, against phytopathogenic fungi. The novel compounds of formula I prove to be effective against specific genera of the fungus class Fungi imperfecti (e.g. Cercospora), Basidiomycetes (e.g. Puccinia) and Ascomycetes (e.g. Erysiphe and Venturia) and especially against Oomycetes (e.g. Plasmopara, Peronospora, Pythium and Phytophthora). They therefore represent in plant protection a valuable addition to the compositions for controlling phytopathogenic fungi. The compounds of formula I can also be used as dressings for protecting seed (fruit, tubers, grains) and plant cuttings from fungal infections and against phytopathogenic fungi that occur in the soil. The invention relates also to compositions comprising compounds of formula I as active ingredient, especially plant-protecting compositions, and to the use thereof in the agricultural sector or related fields. In addition, the present invention includes the preparation of those compositions, wherein the active ingredient is homogeneously mixed with one or more of the substances or groups of substances described herein. Also included is a method of treating plants which is distinguished by the application of the novel compounds of formula I or of the novel compositions. Target crops to be protected within the scope of this invention comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, stone fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucurbi-taceae (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamon, camphor) and plants such as tobacco, nuts, coffee, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, and also ornamentals. The compounds of formula I are normally used in the form of compositions and can be applied to the area or plant to be treated simultaneously or in succession with other active ingredients. Those other active ingredients may be fertilisers, micronutrient donors or other preparations that influence plant growth. It is also possible to use selective herbicides or insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of those preparations, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology. The compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities. Such mixtures are not limited to two active ingredients (one of formula I and one of the list of other fungicides), but to the contrary many comprise more than one active ingredient of the component of formula I and more than one other fungicide. Mixing components which are particularly suited for this purpose include e.g. azoles such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole; pyrimidinyl carbinoles, such as ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such as bupirimate, dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamin, tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim. furalaxy], metalaxyl, R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline; carboxamides, such as carboxin, fenfuram, flutolanii, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine; strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, trifloxystrobin, picoxystrobin, BAS 500F (proposed name pyraclostrobin); dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; N-halomethylthiotetrahydrophthalimides, such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid; Cu-compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper; nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl; organo-p-derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl; various others, such as acibenzolar-S-methyl, anilazine, blasticidin-S, chinomethionate, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, SYP-LI90 (proposed name: flumorph), dithianon, etridiazole, famoxadone, fenamidone, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb, IKF-916, kasugamycin, methasulfocarb, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin, zoxamide (RH7281). Some particularly interesting mixtures in view of technical value in the agricultural practice (comprising at least the one mentioned compound of formula I together with the above mentioned mentioned other fungicide, but not being limited thereto, i.e. such mixtures may comprise additional components according to needs when controlling certain fungi on certain crop plants), having enhanced synergistic levels of fungicidal activity, or being especially well suited for the control of persistent or very damaging phytopathogenic fungi are among the following: 1) 2-phenyl-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound E1.002), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chIorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide; and 2) 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamicle(compouncl E1.011), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil. metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyi-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide, and 3) 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound E1.022), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide, and 4) 2-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound E1.033), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide, and 5) 2-(4-tolyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound El .045), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chIorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide, and 6) 2-(4-ethyl-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound El .053), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl- amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)- phenyl}-ethyl]-amide, and 7) 2-(3,4-difluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynyloxy-acetamide (compound E1.085), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin, chlorothalonil, metalaxyl, metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI. copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb. folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide, and 8) 2-(3-fluoro-4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound E1.091), combined with any one active ingredient selected from cymoxanil. trifloxystrobin. azoxystrobin, picoxystrobin. chlorothalonil, metalaxyl. metaiaxyl-M, pyraclostrobin (BAS500F). dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl. fludioxonil, mancozeb, folpet, fluazinam, iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yioxy)-phenyl}-ethyI]-amide. and 9) 2-(3,4-dichioro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyIoxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (compound E1.102), combined with any one active ingredient selected from cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin. chlorothalonil. metalaxyl, metaiaxyl-M. pyraclostrobin (BAS500F). dimethomorph, fosetyl-AI, copper-salts, acibenzolar-S-methyl, fludioxonil, mancozeb, folpet, fluazinam. iprovalicarb. zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1-yloxy)-phenyl}-ethyl]-amide. In the above mentioned mixtures, the mixture ratio of the active ingredients is so selected that it reaches optional control of the phytopathogenic microorganism on the host plants. This ratio is in general between 100:1 and 1:100. more preferably between 10:1 and 1:10 of a compound of formula I vis-a-vis the second fungicide. The mixtures may not only comprise one of the listed combinational active ingredients, but may comprise more than one additional active ingredients selected from that specified group, thus forming for example 3-way- or even 4-way-mixtures. Suitable carriers and surfactants may be solid or liquid and correspond to the substances ordinarily employed in formulation technology, such as e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilisers. Such carriers and additives are described, for example, in WO 95/30651. A preferred method of applying a compound of formula I, or an agrochemical composition comprising at least one of those compounds, is application to the foliage (foliar application), the frequency and the rate of application depending upon the risk of infestation by the pathogen in question. The compounds of formula I may also be applied to seed grains (coating) either by impregnating the grains with a liquid formulation of the active ingredient or by coating them with a solid formulation. The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in formulation technology, and are for that purpose advantageously formulated in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and by encapsulation in e.g. polymer substances. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. Advantageous rates of application are normally from 1 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, especially from 25 g to 750 g a.i./ha. When used as seed dressings, rates of from 0.001 g to 1.0 g of active ingredient per kg of seed are advantageously used. The formulations, i.e. the compositions, preparations or mixtures comprising the com-pound(s) (active ingredient(s)) of formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants). Further surfactants customarily used in formulation technology will be known to the person skilled in the art or can be found in the relevant technical literature. The agrochemical compositions usually comprise 0.01 to 99 % by weight, preferably 0.1 to 95 % by weight, of a compound of formula I, 99.99 to 1 % by weight, preferably 99.9 to 5 % by weight, of a solid or liquid adjuvant, and 0 to 25 % by weight, preferably 0.1 to 25 % by weight, of a surfactant. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations. The compositions may also comprise further ingredients, such as stabilisers, antifoams, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients for obtaining special effects. The Examples which follow illustrate the invention described above, without limiting the scope thereof in any way. Temperatures are given in degrees Celsius. Ph stands for phenyl. Formic acid (230 g, 5.0 mol) is added dropwise to acetic anhydride (383 g, 3.75 mol) at 0°C. This mixture is stirred for 2 hours at +55°C and subsequently cooled again to 0°C. Tetrahydrofuran (500 ml) is added at this temperature followed by 4-(2-amino-ethyl)-2-methoxy-phenol hydrochloride (50 g, 0.25 mol). The resulting white suspension is stirred for 18 hours at +75 °C, changing into a yellow solution. The reaction mixture is evaporated and the residue is submitted to flash-chromatography to yield N-[2-(4-hydroxy-3-methoxy-phe-nvl)-ethvl1-formamide. 1H-NMR (300 MHz. CDCl3): 2.85(t, 2H, CH2CH2), 3.57(t, 2H, CH2CH2), 3.82(s, 3H, OCH3), 5.69(bs, 1H, NH), 6.67 - 7.09(m, 3H, CH arom.), 8.12(s, 1H, CHO). Sodium methoxide (32 ml of a 5.4 M solution in methanol, 0.17 mol) is added to a solution of N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide (32 g, 0.16 mol) in methanol (400 ml). Propargyl bromide (20 g, 0.17 mol) is added and the mixture is refluxed for 4 hours. After evaporation the residue is taken up in ethyl acetate (400 ml) and washed with water (2 x 200 ml). The organic layer is dried over magnesium sulfate and evaporated. The residue is submitted to flash-chromatography to give the N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide. ^H-NMR (300 MHz, CDCIQ: 2.44 (t, 1H, C=CH), 2.73 (t, 2H, CH2CH2), 3.51 (t, 2H. CH2CH2). 3.82 (s, 3H, OCH3), 4.69 (m, 2H, OCH2), 5.53 (bs, 1H. NH), 6.62 - 6.95 (m, 3H, CH arom.), 8.09 (s, 1H, CHO). N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide (34 g, 0.14 mol) and triethylamine (34 g, 0.34 mol) are dissolved in dichloromethane (120 ml). Bis(trichloro-methyl) carbonate (triphosgene, 16 g, 55 mmol) in dichloromethane (80 ml) is added at +5°C. The mixture is stirred for 4 hours at +5°C and then cooled to -78°C. A solution of titanium tetrachloride (28 g, 0.15 mol) in dichloromethane (150 ml) is added and the mixture is stirred for 2 hours at -40°C. 4-Chlorobenzaldehyde (20 g, 0.14 mol) in dichloromethane (70 ml) is added dropwise and the mixture is stirred for 17 h at room temperature. The mixture is hydrolyzed with 5N HCI (80 ml), stirred 30 minutes at room temperature and washed with water. After evaporation of the organic layer the residue is submitted to flash-chromatography (ethyl acetate/ hexane) to give 2-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-me-thoxv-4-prQp-2-vnvloxv-phenvl)-ethvn-acetamide. 1H-NMR (300 MHz. CDCl3): 2.54 (t, 1H, CHCH), 2.72 (t, 2H, CH2CH2), 3.53 (t, 2H, CH2CH2), 3.84 (s, 3H, OCH3), 4.78 (m, 2H, OCH2), 4.98 (s, 1H, CHOH), 6.07 (bs, 1H, NH), 6.53 - 7.38 (m, 7H, CH arom.). d)2-(4-Chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-aceta-mide (2.6 g, 7.0 mmol) is dissolved in N,N-dimethylformamide (30 ml). Sodium hydride (0.18 g, 7.5 mmol) is added in portions at +5°C. The mixture is stirred for 30 minutes at room temperature. Subsequently iodomethane (1.1 g, 7.5 mmol) is added dropwise and the resulting mixture is stirred for further 3 hours at room temperature. The reaction mixture is poured on ice/water (200 ml) and extracted with ethyl acetate (2 x 200 ml). The combined organic layer is washed with brine (200 ml) and dried over magnesium sulfate. After evaporation of the solvent, the residue is purified by chromatography (ethyl acetate/hexane) to yield 2-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamlde. ^H-NMR (300 MHz, CDCy: 2.53 (t, 1H, C=CH), 2.80 (t, 2H, CH2CH2), 3.34 (s, 3H, OCH3), 3.55 (t. 2H, CH2CH2), 3.84 (s, 3H, OCH3), 4.58 (s, 1H, CHOH), 4.79 (m, 2H, OCH2), 6.68 - 7.34 (m, 8H, CH arom., NH). 4-Bromoacetophenone (100 g, 0.5 mol) is dissolved in 300 ml of glacial acetic acid. Chlorine gas is admitted at a rate that allows to control the reaction temperature not to exceed +60°C. The chlorination is continued until an excess of the halogen has been absorbed, indicated by the development of a yellow color. The reaction mixture is poured on ice and extracted with ethyl acetate. The organic phase is separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated. 1-(4-Bromo-phenyl)-2,2-dichloro-ethanone is obtained as residue sufficiently pure to be used in the next step. 1H-NMR (300 MHz. CDCI;^): 6.50 (s, 1H, CHCI2), 7.60 (d, 2H, CH arom.), 7.92 (d, 2H, CH arom.). Sodium hydroxide (72 g, 1.8 mol) is dissolved in 650 ml of water. The solution is heated to +60°C and 1-(4-bromo-phenyl)-2,2-dichloro-ethanone (130 g, 0.48 mol) is added dropwise in order to control the reaction temperature not to exceed +65°C. After the addition is complete, stirring is continued for 1 hour at +60°C. The reaction mixture is then cooled to +15°C and 95 ml of 10 N hydrochloric acid are added. Subsequently diethyl ether is added and the mixture is stirred vigorously for 30 minutes. The organic phase is separated and the aqueous layer is extracted twice with diethyl ether. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated to yield (4-bromo-phenyl)-hydroxy-acetic acid. 'H-NMR (300 MHz, CDCU): 4.95 (s, 1H, CHOH), 7.30 (d, 2H, CH arom.). 7.48 (d, 2H, CH arom.). (4-Bromo-phenyl)-hydroxy-acetic acid (97 g, 0.42 mol) is dissolved in 200 ml of acetone and cooled to -10°C. At this temperature 23 ml of concentrated sulfuric acid are added drop-wise. After the addition is complete, the reaction mixture is stirred at -10°C for further 30 minutes and is subsequently poured into a cooled (0°C) solution of sodium carbonate (86 g, mol) in 800 ml of water. The crystalline 5-(4-bromo-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-one is filtered, washed with ice-cold water and dried in the high-vacuum. 1H-NMR (300 MHz, 5-(4-Bromo-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-one (15 g, 55 mmol) is dissolved in 50 ml of ethanol. 4-(2-Amino-ethyl)-2-methoxy-phenol hydrochloride (14 g, 69 mmol) and triethyl-amine (7.0 g, 69 mmol) are added and the mixture is stirred for 72 hours at room temperature. The solvent is removed in vacuum and the residue is extracted with ethyl acetate and IN hydrochloric acid. The aqueous layer is extracted twice with ethyl acetate and the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The remaining 2-(4-bromo-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide is purified by chromatography on silicagel. 1H-NMR (300 MHz. CDCl2): 2.71 (t. 2H, CH2CH2), 3.54 (t, 2H, CH2CH2), 3.80 (s, 3H, OCH3), 5.59 (s, 1H, CHOH), 6.16 (bs, 1H, NH), 6.52 - 7.35 (m. 7H, CH arom.). e) A 80 % solution of propargyl bromide in toluene (10.5 g, 71 mmol) is added slowly at room temperature to a mixture of 2-(4-bromo-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide (11 g, 29 mmol), 30 % sodium hydroxide solution (14 ml, 0.14 mol) and catalytic amounts of tetrabutylammonium bromide in 40 ml of dichloromethane. The reaction mixture is stirred for 16 hours at +40°C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The organic phase is separated and the aqueous layer is extracted three times with dichloromethane. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate / hexane 1 : 1) to yield 2-(4-bromc-phenyi)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetam!de. ^H-NMR (300 MHz, CDCI.): 2.51 (t, 1H, C=CH), 2.54 (t, 1H, C=CH), 2.81 (t, 2H, CH2CH2), 3.54 (t, 2H, CH2CH2), 3.86 (s, 3H, OCH3), 3.97 (dd, 1H, OCH2), 4.20 (dd, 1H, OCH2), 4.78 (d, 2H, OCH2), 4.96 (s, 1H, CHOH), 6.70 - 7.52 (m, 8H, CH arom., NH). A solution of benzoyl peroxide (2.37 g. 9.8 mmol) in CH2CI2 is added to a vigorously stirred solution of 2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine (2.0 g. 9.8 mmol) in 49 ml of a carbonate buffer solution (pH = 10.5). The reaction mixture is stirred at room temperature for 6 h. The water layer is extracted twice with CH2CI2, the organic layers are combined and dried over Na2S04. After evaporation of the solvent the product is purified by flash chromatography (ethyl acetateihexane, 1:2) to yield N-ben2oyloxy-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine as an oil. BOP (2.0 g, 4.5 mmol) is added to a solution of (4-chloro-phenyl)-acetic acid (0.7 g, 4.1 mmol), N-benzoyloxy-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine (1.4 g, 4.3 mmol) and N-ethyldiisopropylamine (2.8 ml, 16.4 mmol) in 10 ml DMF. The reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into water and extracted three times with ethyl acetate. The organic phase is dried over Na2S04 and concentrated. The crude product is purified by flash chromatography (ethyl acetate:hexane, 1:3) to yield N-benzoyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide as an oil. Methanesulfonyl chloride (0.022 ml, 0.286 mmol) is added dropwise to a solution of 2-(4-chloro-phenyl)-N-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (0.1 g, 0.26 mmol), and Et3N (0.036 ml, 0.26mmol) in 1 ml CH2CI2 at 0°C. The reaction mixture is allowed to warm to room temperature and stirred for another 2 hours. The reaction mixture is then washed with water, 1N HCI, and brine and dried over Na2S04- After rotary evaporation, the product is purified by flash chromatography (ethyl acetate:hexane, 1:2) to yield 2-(4-chloro-phenyl)-N-mesyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide as a solid, mp. 91-93°C. e) To a solution of 2-(4-chloro-phenyl)-N-mesyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (452 mg, Immol) in a mixture of 6 ml acetonitrile and 6 ml n-pro-panol during a period of 12 hours a solution of triethylamine (0.146 ml, 1.05 mmol) in 12 ml of acetonitrile is added dropwise. The mixture is stirred for 20 hours at room temperature. The solvent and excess n-propanol is removed under reduced pressure and the residue was diluted with ethyl acetate (30 ml), washed with water, IN HCI, and brine, and dried with Na2S04. After evaporation of the solvent the product is purified by flash chromatography (ethyl acetate:hexane, 1:2) to yield 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide In form of an oil. 1H-NMR (300 MHz, CDC!.): 0.89(t, 3H, CH3), 1.58(q, 2H, CH2), 2.50(t, 1H, C=CH), 2.79(t, 2H, CH2CH2), 3.35(t, 2H, OCH2), 3.52(dt, 2H, CH2CH2), 3.83(s, 3H, OCH3), 4.63(s, 1H, CHOH), 4.74(d, 2H, OCH2), 6.67 - 7.30(m, 8H, CH arom., NH). To a mixture of thionyl chloride (3.7 g, 31 mmol) in toluene (10 ml) containing 3 drops of pyridine is added 4-bromomandeiic acid (2.9 g, 13 mmol) in diethylether (40 ml). The reaction mixture is refluxed for 2 hours. The solvent is removed and the residue is co-evaporated with toluene. Subsequently the residue is dissolved in dioxane (20 ml) and added to 2-(3-methoxy-4-prop-2-ynyloxy-pheny!)-ethylamine (2.2 g, 11 mmol) and triethylamine (1.0 g, 10 mmol) in dioxane (20 ml). The resulting mixture is stirred for 16 hours, diluted with water (100 ml) and extracted with ethyl acetate (2 x 200 ml). The combined organic layer is washed with brine (150 ml), dried over magnesium sulfate and evaporated. 2-(4-Bromo-phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide is obtained which is purified by chromatography on silica gel using ethyl/acetate/hexane as eluent. 1H-NMR (300 MHz. CDCl3): 2.53(t. 1H, C=CH), 2.82(t, 2H, CH2CH2), 3.60(t, 2H, CH2CH2), 3.87(s, 3H. OCH3), 4.79(d, 2H, OCH2), 5.29(s, 1H, CHCI). 6.70-7.48(m, 8H, CH arom., NH). To sodium methylmercaptide (0.85 g) in 1,4-dioxane (50 ml) is added 2-(4-bromo-phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (4.4 g). The reaction mixture is stirred under nitrogen at room temperature for 2 hours. It is extracted with ethyl acetate (2 X 200 ml). The organic layers are washed with brine (2 x 200 ml), combined, dried (MgS04) and the solvent is evaporated. 2-(4-Bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyi-oxy-phenyl)-ethyl]-2-methylthio-acetamide is obtained as an oil, which is purified by flash-column chromatography on silica gel using ethyl acetate/hexane. 1H-NMR (300 MHz. CDCI3): 2.00 (s, 3H), 2.52 (t, 1H), 2.80 (t, 2H), 3.56 (q, 2H), 3.82 (s, 3H), 4.36 (s, 1H). 4.75 (d, 2H), 6.67 (dd, 1H), 6.72 (d, 1H), 6.77 (t, 1H), 6.95 (d, 1H), 7.16 (d, 2H), 7.42 (d, 2H). According to the above procedure of Example E5 the compounds listed in table E5 are obtained. Analogously to the above examples the compounds of tables 1 to 35 are obtained. Ph stands for phenyl wherein the combination of the groups R1, R2, R3, R9 and R10 corresponds each to one row in table A. wherein the combination of the groups R1, R2, R3, R9 and R10 corresponds each to one row in table A. i wherein the combination of the groups R1, R2, R3, R9 and R10 corresponds each to one row in table A. Table 16: Compounds represented by the Formula 1.16 wherein the combination of the groups R1, R2, R3, R9 and R10 corresponds each to one row in table A. Table 23: Compounds represented by the Formula 1.23 wherein the combination of the groups R1, R2, R3, R9 and R10 corresponds each to one row in table A. Table 30: Compounds represented by the Formula 1.30 Table 34: Compounds represented by the Formula 1.34 Biological Examples D-1: Action against Plasmopara viticola on vines a) Residual-protective action Vine seedlings are sprayed at the 4- to 5-leaf stage with a spray mixture (0.02 % active ingredient) prepared from a wettable powder formulation of the test compound. After 24 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation for 6 days at 95-100 % relative humidity and +20°C. b) Residual-curative action Vine seedlings are infected at the 4- to 5-leaf stage with a sporangia suspension of the fungus. After incubation for 24 hours in a humidity chamber at 95-100 % relative humidity and +20°C, the infected plants are dried and sprayed with a spray mixture (0.02 % active ingredient) prepared from a wettable powder formulation of the test compound. After the spray coating has dried, the treated plants are placed in the humidity chamber again. Fungus infestation is evaluated 6 days after infection. D-2: Action against Phvtophthora on tomato plants a) Residual-protective action After a cultivation period of 3 weeks, tomato plants are sprayed with a spray mixture (0.02 % active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 5 days at 90-100 % relative humidity and +20°C. b) Systemic action After a cultivation period of 3 weeks, tomato plants are watered with a spray mixture (0.02 % active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above the ground. After 96 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100 % relative humidity D-3 : Action against Phvtophthora on potato plants a) Residual-protective action 2-3 week old potato plants (Bintje variety) are sprayed with a spray mixture (0.02 % active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100 % relative humidity and -i-20°C. b) Systemic action 2-3 week old potato plants (Bintje variety) are watered with a spray mixture (0.02 % active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above the ground. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100 % relative humidity and +20°C. Fungal infestation is effectively controlled with compounds of Tables 1 to 35. Compounds E1.003, E1.004, E1.009, E1.011, E1.012, E1.019, E1.020, E1.021, E1.022, El.025, E1.031, El.032, E1.033, E1.038, E1.045, E1.049, E1.050, E1.053, E1.085, E1.089, E1.090, E1.091, E1.102, E1.110, E1.112, E1.121, E1.125, E1.129 at 200 ppm inhibit fungal infestations in both tests D-3a) and D-3b) by 80-100 %. At the same time untreated plants showed pathogen attack of 80-100 %. including the optical isomers thereof and mixtures of such isomers, wherein Rt is hydrogen, aikyl, cycloalkyl or optionally substituted aryl, R2 and R3 are each independently hydrogen or alkyl, R4 is alkyl, alkenyl or alkynyl, R5, R6. R7, and R8 are each independently hydrogen or alkyl, R9 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, Rio is optionally substituted aryl or optionally substituted heteroaryl, and Z is halogen, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted arylthio, optionally substituted alkylthio, optionally substituted alkenylthio, optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenylsulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl or optionally substituted alkynylsutfonyl. 2. A compound according to claim 1 wherein Ri is hydrogen, alkyl, cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by substituents selected from the group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may in turn be substituted by one or several halogens; alkoxy; alkenyloxy; alkynyloxy; alkoxy-alkyl; haloalkoxy; alkytthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; and R2 and R3 are independently of each other hydrogen or C1-C4 alkyl; and R4 is C1-C8 alkyl, C2-C8 alkenyl, or Cz-Csalkynyl; and R5, R6, R7 and R6 are independently of each other hydrogen or C1-C4 alkyl; and R9 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4alkenyl or C3-C4alkynyl; and R10 is aryl or heteroaryl, each optionally substituted with substituents selected from to group comprising alkyl, alkenyl, alkynyl, cycloalkyi, cycloaikyl-alkyi, phenyl and phenylalkyi, where all these groups may be substituted with one or more substituents selected from the group comprising halogen; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; halo-alkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl and alkynyloxycarbonyl; and Z is halogen, optionally substituted aryloxy or arylthio wherein in each the aryl may be optionally substituted by one or more substituents selected from the group comprising halogen, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8alkynyloxy, C1-C6 alkoxy-C1-C8 alkyI, C1-C8 halo-alkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C2-C8 alkylsulfonyl, formyl, C2-C8 alkanoyI, hydroxy, halogen, cyano, nitro, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, carboxyl and C2-C8 al-koxycarbonyl; or is optionally substituted C2-C8 alkoxy, optionally substituted C2-C8alke-nyloxy, optionally substituted C2-CBalkynyloxy, optionally substituted C1-C8 alkylthio, optionally substituted C2-C8alkenylthio, optionally substituted C2-C8alkynylthio, optionally substituted C1-C8 alkylsulfinyl, optionally substituted C2-C8 alkenylsulfinyl, optionally substituted C2-C8alkynylsulfinyl, optionally substituted C1-C8 alkylsulfonyl, optionally substituted C2-C8alkenylsulfonyl or optionally substituted C2-C8alkynylsulfonyl wherein each alkyl, alkenyl or alkynyl group may carry one or more substituents selected from the group comprising halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C2-C8 cycloalkyI, nitro, cyano, hydroxy, phenyl, mercapto, C1-C4 alkylcarbonyl and C1-C4 alkoxycarbonyl. 3. A compound according to claim 1 wherein Ri is hydrogen, C1-C8 alkyI, C2-C8 cycloalkyI, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8 haloalkyI, C1-C8 alkoxy, C2-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C1-C8 alkylsulfonyl, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and R2 and R3 are hydrogen; and R4 is C1-C6 alkyI; and R5, R6 and R7 are hydrogen and Ra is hydrogen, methyl or ethyl, preferably methyl; and R9 is hydrogen or C1-C4 alkyl; an8 R10 is phenyl, naphthyl or biphenyl, each optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyI, C2-C8alkenyl, C2-C8alkynyl, C2-C8 haloalkyI, C1-C8 alkoxy, C1-C8 haloalkoxy. C1-C8 alkylthio, C1-C8 haloalkylthio, C1-C8 alkylsulfonyl, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is halogen; C1-C8 alkoxy, C2-C8alkenyloxy, C1-C8 alkynyloxy, C1-C8 alkoxy-C1-C8 alkoxy, C2-C8alkenyloxy-C1-C8 alkoxy, C2-C8alkynyloxy-Ci-C8alkoxy, C1-C8 haloaikoxy, Cs-Cacyclo-alkyl-C1-C8 alkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C1-C8 alkynylthio, C1-C8 haloalkylthio, C2-C8 cycloalkyJ-C1-C8 alkylthio, C1-C8 alkylsuJfinyl, C1-C8 alkylsulfonyl, C2-Caalkenylsulfinyl, C2-C8alkenylsulfonyl, C2-C8alkynylsulfinyl or C2-Caalkynylsulfonyl. 4. A compound of formula I according to claim 1 wherein R1 is hydrogen, C1-C8 alkyl or phenyl optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyI, C1-C8 haloalkyI, C1-C8 alkoxy, C1-C8 haloal-koxy, C1-C8 alkylthio, C1-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and R2 and R3 are hydrogen; and R4 is C1-C4 alkyl, and R5, R6 and R7 are hydrogen and R8 is hydrogen or methyl; and R9 is hydrogen; and Rio is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyI, C1-C8 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is halogen; C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C1-C4 alkoxy-Ci-C2alkoxy, C2-Caalkylthio, C2-C8alkenylthio or C2-Caalkynylthio. 5. A compound of formula I according to claim 1 wherein R1 is hydrogen, C1-C8 alkyI or C2-C8 cycloalkyI; and R2, R3, R5, R6, R7, R8 and R9 are hydrogen; and R4 is methyl or ethyl; and R10 is phenyl, naphthyl, 1,3-biphenyI or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C1-C8 alkyl, C1-C8 haloalkyI, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkylthio, C1-C8 haloalkylthio, halogen, cyano, nitro and C1-C8 alkoxycarbonyl; and Z is C1-C8 alkoxy, C2-C6alkenyloxy or C2-C6alkynyloxy. 6. A compound of formula I according to any of claims 1 to 5 wherein R1 is hydrogen or C1-C4alkyl. 7. A compound of formula I according to claim 1 selected from the group comprising 2-(4-bromo-phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-chloro-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-chloro-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-bromo-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(3,4-dichloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyi]-acetamide, 2-(4-bromo-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyI]-acetamide, 2-(4-chloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyI]-acetamide, 2-(3,4-dichloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide, 2-(4-chIoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-propoxy-acetamide, 2-(3.4-dichloro-phenyl)-N-[2-{3-methoxy-4-prop-2-ynyloxy-phenyI)-ethyl]-2-propoxy-acetamide, 2-(4-bromo-phenyl)-2-cyclopropylmethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-chloro-phenyl)-2-cyclopropylmethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-cyclopropylmethoxy-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-yny!oxy-phenyl)-ethyl]-acetamide, 2-(4-bromo-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(4-chloro-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-(3,4-dichloro-phenyl)-2-ethoxymethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-allyloxy-2-(4-bromo-phenyl)-N"[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-allyloxy-2-(4-chIoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide, 2-allyloxy-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-2-(but-2-enyloxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(but-2-enyloxy)-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyioxy-phenyl)-ethyl]- acetamide, 2-(but-2-enyloxy)-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-{3,4-dichIoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-biphenyl-4-yl-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop-2-yny!oxy-phenyl)-ethyl]-2-naphthalen-2-yl-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop-2-yny!oxy-phenyl)-ethyl]-2-prop-2-ynyloxy-2-p-tolyl-acetamide, 2-(4-ethyl-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-2-(4-trifluoromethyl- phenyl)-acetamide, 2-(4-bromo-phenyl)-2-but-2-ynyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-but-2-ynyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-but-2-ynyloxy-2-(3,4-dichloro-pheny!)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyisulfanyl- acetamide, 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynylsuifanyl- acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynylsulfanyl-acetamide, 2-ailylsulfanyl-2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-allylsulfanyl-2-(4-chioro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-allylsulfanyl-2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]- acetamide, 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(3,4-dichloro-phenyl)-N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide. 2-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(3,4-difluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy- acetamide, 2-(4-chloro-3-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynyloxy-acetamide, and 2-(3-chloro-4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2- ynyloxy-acetamide. 10. A composition according to claim 9 which comprises at least one additional fungici-dally active compound, preferably selected from the group consisting of cymoxanil, trifloxystrobin, azoxystrobin, picoxystrobin. chlorothaionil, metalaxyl. metalaxyl-M, pyraclostrobin (BAS500F), dimethomorph, fosetyl-AI, copper-salts, actbenzolar-S-methyl, fludioxonil, mancozeb, folpet. fluazinam. iprovalicarb, zoxamid and (S)-2-(methylsulfonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1 -yloxy)-phenyl}-ethyl]-amide. 11. A method of controlling and preventing an infestation of crop plants by phytopathogenic microorganisms, which comprises the application of a compound of formula I according to claim 1 as active ingredient to the plant, to parts of plants or to the locus thereof. 12. A method according to claim 11, wherein the phytopathogenic microorganisms are fungal organisms. 13. A process for the preparation of a compound of formula la according to claim 1 wherein R4 and R10 are as defined for formula I in claim 1, with a propargyiating agent of formula XXII (XXII) wherein Y is a leaving group, e.g. bromine or chlorine or a tosyl, mesyl or triftuoromethylsulfonyl. |
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| Patent Number | 208719 | |||||||||||||||
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| Indian Patent Application Number | IN/PCT/2002/1841/CHE | |||||||||||||||
| PG Journal Number | 13/2008 | |||||||||||||||
| Publication Date | 31-Mar-2008 | |||||||||||||||
| Grant Date | 07-Aug-2007 | |||||||||||||||
| Date of Filing | 11-Nov-2002 | |||||||||||||||
| Name of Patentee | M/S. SYNGENTA PARTICIPATIONS AG | |||||||||||||||
| Applicant Address | 4058 Basel (CH) | |||||||||||||||
Inventors:
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| PCT International Classification Number | A01N 37/36 | |||||||||||||||
| PCT International Application Number | PCT/EP2001/005530 | |||||||||||||||
| PCT International Filing date | 2001-05-15 | |||||||||||||||
PCT Conventions:
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