Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-10-04
1998-08-04
Lambkin, Deborah C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549 71, 549 72, 549 73, A01N 4306, C07D33338, C07D33322
Patent
active
057894370
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/01173 Mar. 29, 1995.
The present invention relates to novel microbicidal compositions based on dibromothiophene-carboxylic acid derivatives which are known in some cases, and the use of these substances for controlling undesired microorganisms. Additionally, the invention also relates to new dibromo-thiophene-carboxylic acid derivatives and a plurality of processes for their preparation.
It has already been disclosed that certain halogenothiophene-carboxamide derivatives can be employed for controlling plant diseases (cf. EP-OS 0 450 355). The activity of these previously known compounds, however, is not completely satisfactory in all fields of application, in particular at low application rates.
Furthermore, certain 4,5-dibromo-thiophene-2-carboxylic acid derivatives are known, such as, for example, the compounds 4,5-dibromo-thiophene-2-carboxylic acid methyl ester (CA Reg. No. 62224-24-2) and ethyl ester (CA Reg. No. 62224-25-3) and 1,1-dimethylethyl ester (CA Reg. No. 62224-26-4) and 2-propinyl ester (CA Reg. No. 116 041-66-8) and 1-methyl-2-propinyl ester (CA Reg. No. 131 818-24-1) and 3-butinyl ester (CA Reg. No. 131 818-21-8) and N,N-dimethylamide (CA Reg. No. 111 859-96-2) and N-ethoxy-amide (CA Reg. No. 131 818-25-2) and also 4,5-dibromothiophene-2-carboxylic acid (CA Reg. No. 6324-10-3) and -carboxamide (Beilstein Reg. No. 129 357).
To date, nothing is known about fungicidal activity of these compounds.
It has now been found that the dibromo-thiophene-carboxylic acid derivatives, which are known in some cases, of the formula ##STR4## in which R represents the groups --XR.sup.1, --NR.sup.2 R.sup.3, --NR.sup.4 OR.sup.5 or --NR.sup.4 --N(R.sup.5).sub.2, where be substituted by halogen, cyano, amino, hydroxyl, mercapto, carboxyl, nitro, alkoxy, alkylthio, alkoxycarbonyl and/or the group ##STR5## or R.sup.1 represents optionally substituted alkenyl or optionally substituted alkinyl, or optionally substituted, tetrahydrofuran, tetrahydrothiophene, tetrahydropyran or tetrahydrothiopyran, each of which is optionally substituted, and aryl, aralkyl, hetaryl or hetarylalkyl, each of which is optionally substituted, alkyl which can be substituted by halogen, cyano, amino, hydroxyl, mercapto, nitro, alkoxy, alkylthio and/or the group ##STR6## or represent alkenyl which is optionally substituted by halogen, or alkinyl which is optionally substituted by halogen, or be substituted by alkyl, halogen, halogenoalkyl, cyano, alkylenedioxo, cycloalkyl which is optionally substituted by alkyl, and/or by optionally substituted phenyl, or tetrahydrothiopyran, each of which is optionally substituted, and optionally substituted aralkyloxy, optionally substituted, being possible for a CH.sub.2 group to be replaced by O, S or NR.sup.6, alkyl, alkenyl or alkinyl, each of which is optionally substituted; and optionally substituted aralkyl, alkenyl, optionally substituted alkinyl or optionally substituted benzyl and substituted alkenyl, optionally substituted alkinyl or optionally substituted benzyl, or possible for a CH.sub.2 group to be replaced by O, S or NR.sup.6, where R.sup.6 has the meanings indicated above,
Depending on the nature of the substituents, the compounds of the formula (I) can exist as geometric and/or optical isomers or isomer mixtures of differing composition. The invention relates both to the use of the pure isomers and of the isomer mixtures.
Formula (I) provides a general definition of the dibromo-thiophene-carboxylic acid derivatives which can be used according to the invention. --NR.sup.4 OR.sup.5 and --NR.sup.4 --N(R.sup.5).sub.2. be mono- to pentasubstituted, identically or differently, by halogen, cyano, amino, hydroxyl, mercapto, carboxyl, nitro; alkoxy, alkylthio or alkoxycarbonyl, each of which is straight-chain or branched, each having 1 to 6 carbon atoms in the individual alkyl moieties; and also the group --NR.sup.7 R.sup.8, or carbon atoms, each of which is optionally mono- to pentasubstituted, identically or differently, by halogen, or carbon atoms in th
REFERENCES:
patent: 3536473 (1970-10-01), Popoff et al.
patent: 5034049 (1991-07-01), Kober et al.
Assmann Lutz
Dehne Heinz-Wilhelm
Ecker Uta
Elbe Hans-Ludwig
Hanssler Gerd
Bayer Aktiengesellschaft
Lambkin Deborah C.
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