Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-01-20
2000-08-22
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549487, A01N 4308, C07D30730
Patent
active
061073369
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP97/03693 filed Jul. 7, 1997.
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel dihydrofuran-carboxamides, to a process for their preparation and to their use as microbicides.
BACKGROUND OF THE INVENTION
It is already known that certain dihydrofurancarboxanilides have fungicidal properties (cf. DE-A 1 914 954 and J. Pesticide Sci. 18 (1993), 245-251). Thus, for example, 2-methyl-4,5-dihydrofuran-3-carboxanilide and 2-methyl-4,5-dihydrofuran-3-N-(1,1,3-trimethyl-indan-4-yl)-carboxamide can be used for controlling fungi. The activity of these compounds is good, but in some cases leaves something to be desired at low application rates.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel dihydrofuran-carboxamides of the formula ##STR3## in which R represents groupings of the formulae ##STR4## in which R.sup.1 represents optionally substituted cycloalkyl, optionally substituted bicycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted aroxy, optionally substituted aralkyl or represents alkyl, to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, optionally substituted aralkyl, optionally substituted aralkyl and
Furthermore, it has been found that dihydrofuran-carboxamides of the formula (I) are obtained when 2-methyl-4,5-dihydrofuran-3-carbonyl halides of the formula ##STR5## in which Hal represents chlorine or bromine, presence of a diluent.
Finally, it has been found that the novel dihydrofuran-carboxamides of the formula (I) have very good microbicidal properties and can be employed for controlling undesirable microorganisms both in crop protection and in the protection of materials.
Surprisingly, the dihydrofuran-carboxamides according to the invention have considerably better fungicidal activity than 2-methyl-4,5-dihydrofuran-3-carboxanilide and 2-methyl-4,5-dihydrofuran-3-N-(1,1,3-trimethylindan-4-yl)-carboxamide, which are constitutionally similar prior-art active compounds of the same direction of action.
The formula (I) provides a general definition of the dihydrofuran-carboxamides according to the invention. ##STR6## in which R.sup.1 preferably represents cycloalkyl having 3 to 8 carbon atoms which is optionally mono- to trisubstituted by identical or different alkyl groups having 1 to 4 carbon atoms, represents bicycloalkyl having 7 to 12 carbon atoms which is optionally mono- to trisubstituted by identical or different alkyl groups having 1 to 4 carbon atoms, represents cycloalkenyl having 5 to 8 carbon atoms which is optionally mono- to trisubstituted by identical or different alkyl groups having 1 to 4 carbon atoms or represents cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituted by identical or different alkyl groups having 1 to 4 carbon atoms, or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, or may be mono- to trisubstituted in the phenyl moiety by identical or alkyl having 1 to 4 carbon atoms, carbon atoms, fluorine, chlorine, bromine, cycloalkyl having 3 to 8 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms or represents halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4 carbon atoms in the
REFERENCES:
patent: 5223526 (1993-06-01), McLoughlin et al.
patent: 5330995 (1994-07-01), Eicken et al.
patent: 5438070 (1995-08-01), Eicken et al.
patent: 5480897 (1996-01-01), Eicken et al.
patent: 5556988 (1996-09-01), Eicken et al.
patent: 5589493 (1996-12-01), Eicken et al.
Patent Abstracts of Japan, vol. 014, No. 417, 1990 & JP 02-157266 Mitsubishi Kasei Corp.
Journal of Pesticide Science, vol. 18, No. 3, Aug. 1993, pp. 245-251.
Chemische Berichte, 104 (month unavailable), 1971, pp. 734-738.
Bielefeldt Dietmar
Dutzmann Stefan
Elbe Hans-Ludwig
Kugler Martin
Kunisch Franz
Bayer Aktiengesellschaft
Dentz Bernard
Gil Joseph C.
Marmo Carol
LandOfFree
Dihydrofuran carboxamides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Dihydrofuran carboxamides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dihydrofuran carboxamides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-581616