Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-05-20
1998-06-30
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514212, 514241, 514246, 514248, 514249, 514252, 514259, 540601, 544295, 544296, 544238, 544319, 544180, 544212, 544216, 544219, C07D23934, C07D23970, C07D40312, A01N 4354
Patent
active
057734453
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP94/03773, filed Nov. 14, 1994, published as WO95/14674 Jun. 1, 1995.
The invention relates to new methyl 3-methoxy-2-phenyl-acrylates, to a process for their preparation, and to their use as pesticides.
It is known that certain methyl 3-methoxy-acrylates, such as, for example, the compound methyl 3-methoxy-2-(6-phenyl-2-pyridylthio)-acrylate or the compound methyl have fungicidal properties (cf. for example EP 383 117).
However, the activity of these previously known compounds is not entirely satisfactory in all sorts of applications, in particular when low application rates and concentrations are used.
New methyl 3-methoxy-2-phenyl-acrylates of the general formula (I) ##STR2## in which Y represents fluorine, chlorine, bromine or iodine, --, --NH--, --N(CH.sub.3)--, --CH.sub.2 O-- or --CH.sub.2 S--, have been found.
If appropriate the compounds of the formula (I) can exist in the form of geometric isomers or variously composed isomer mixtures. The invention claims both the pure isomers and the isomer mixtures.
Furthermore, it has been found that the new methyl 3-methoxy-2-phenyl-acrylates of the general formula (I) ##STR3## in which Y represents fluorine, chlorine, bromine or iodine, --, --NH--, --N(CH.sub.3)--, --CH.sub.2 O-- or --CH.sub.2 S--, are obtained when ##STR4## is reacted with pyrimidine derivatives of the formula (III) ##STR5## in which R and Y have the abovementioned meaning and presence of a reaction auxiliary; or by process a), of the formula (Ia) ##STR6## in which X and Y independently of one another represent fluorine, chlorine, bromine or iodine, --, --NH--, --N(CH.sub.3)--, --CH.sub.2 O-- or --CH.sub.2 S--, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a catalyst.
Finally, it has been found that the new methyl 3-methoxy-2-phenyl-acrylates of the general formula (I) have a good activity against pests.
Surprisingly, the methyl 3-methoxy-2-phenyl-acrylates of the general formula (I) according to the invention show considerably better activity against phytopathogenic microorganisms compared with the methyl 3-methoxy-acrylates known from the prior art, such as, for example, the compound methyl 3-methoxy-2-(6-phenyl-2-pyridylthio)-acrylate or the compound methyl which are similar compounds chemically and/or from the point of view of their action.
Formula (I) provides a general definition of the methyl 3-methoxy-2-phenyl-acrylates according to the invention. Preferred compounds of the formula (I) are those in which formula Ar--Z--, in which monosubstituted or polysubstituted by identical or different substituents, or represents heteroaryl having 2 to 9 carbon atoms and 1 to 5 identical or different hetero atoms, and which is optionally monosubstituted or polysubstituted by identical or different substituents and/or benzo-fused, suitable substituents in each case being: in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, 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, halogenoalkylsulfinyl or halogenoalkylsulfonyl, 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, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each of which has 1 to 6 carbon atoms in the individual alkyl moieties, or in each case divalent alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the series comprising halogen and/or straight-chain or
Dehne Heinz-Wilhelm
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Bayer Aktiengesellschaft
Ford John M.
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