Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – N-c doai
Patent
1995-11-13
1998-03-17
Ambrose, Michael G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
N-c doai
514478, 514484, 514486, 514490, 558233, A01N 4722, C07C33310
Patent
active
057287295
DESCRIPTION:
BRIEF SUMMARY
This application was filed under 35 USC 371 and was based upon PCT International Application No. PCT/EP94/01417, filed May 4, 1994.
The invention relates to new 3-methoxy-2-phenyl-acrylic esters, to a process for their preparation, and to their use as pesticides.
It has already been disclosed that certain 3-methoxy-2-phenyl-acrylic esters have fungicidal properties (cf. EP-OS (European Published Specification) 0 178 826). For example, methyl 3-methoxy-2-(2-benzoyloxyphenyl)-acrylate can be used for combating fungi. However, the activity of this substance is not entirely satisfactory in all fields of application when used at low rates.
There have now been found new 3-methoxy-2-phenyl-acrylic esters of the formula ##STR2## in which R represents in each case optionally substituted alkyl, cycloalkyl or aryl and
If appropriate, the compounds of the formula (I) can exist as geometric and/or optical isomers or variously composed isomer mixtures, depending on the nature of the substituents. The invention relates to the pure isomers and to the isomer mixtures.
Furthermore, it has been found that 3-methoxy-2-phenyl-acrylic esters of the formula (I) are obtained when methyl 2-(2-hydroxyphenyl)-3-methoxy-acrylate, of the formula ##STR3## is reacted with N-acyl-isothiocyanates of the formula ##STR4## in which R and n have the abovementioned meaning, presence of an acid-binding agent.
Finally, it has been found that the new 3-methoxy-2-phenyl-acrylic esters of the formula (I) are highly suitable for use as pesticides.
Surprisingly, the 3-methoxy-2-phenyl-acrylic esters of the formula (I) according to the invention show a considerably better activity against phytopathogenic microorganisms than, for example, methyl 3-methoxy-2-(2-benzoyloxyphenyl)-acrylate, which is a prior-art active compound of the same direction of action and a similar constitution.
Formula (I) provides a general definition of the 3-methoxy-2-phenyl-acrylic esters according to the invention. carbon atoms, cycloalkyl having 3 to 8 carbon atoms, or aralkyl or aryl, each of which has 6 to 10 carbon atoms in the aryl moiety and, if appropriate, 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents, it being possible for the aryl moiety in each case to be substituted by straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl or alkenyloxy, each of which has 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each of which has 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched N-alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl or alkoxy moieties, in each case divalent alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms and each of which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, 3 to 7-membered heterocyclyl having 2 to 6 carbon atoms and 1 to 3 identical or different hetero atoms--in particular nitrogen, oxygen and/or sulphur-, and phenyl, phenoxy, benzyl, benzyloxy, phenylethyl and/or phenylethyloxy, each of which is optionally monosubstituted to pentasubstituted in the phenyl moiety by identical or different substituents from the series cons
REFERENCES:
Makhsumov, A.G. et al. Chemical Abstracts. vol. 88(Jun. 1978): Abstract No. 190561.
Dehne Heinz-Wilhelm
Gayer Herbert
Gerdes Peter
Ambrose Michael G.
Bayer Aktiengesellschaft
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