Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-01-28
2000-02-01
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 80, 548111, 548243, 548244, A01N 4352, C07D41312
Patent
active
060203544
DESCRIPTION:
BRIEF SUMMARY
HALOGENOBENZIMIDAZOLES
The present invention relates to new halogenobenzimidazoles, to a process for their preparation, and to their use as microbicides in crop protection and in the protection of materials. The invention furthermore relates to new intermediates and to a process for their preparation.
It has already been disclosed that certain benzimidazole derivatives have fungicidal properties (cf. DE-A 4 139 950 and EP-A 0 517 476). 2-Cyano-3-dimethylaminosulphonyl-6,6,7,7-tetrafluoro-[1,4]dioxino[2,3-f]be nzimidazole and 2-cyano-6,6-difluoro-2-methylaminosulphonyl-[1,3]dioxolo[4,5-f]benzimidazo le, for example, can be employed for controlling fungi. The efficacy of these substances is good, but leaves something to be desired in some cases when low rates of application are used.
There have now been found new halogenobenzimidazoles of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl, alkylcarbonyl alkoxycarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl or --Z--R.sup.5 or ##STR3## where R.sup.5 represents optionally substituted aryl or optionally substituted heterocyclyl, SO.sub.2, or CO, group being bonded to R.sup.5, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted arylsulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl, or bonded represent an optionally alkyl-substituted heterocyclic ring which can additionally contain an oxygen atom or an alkylimino group and each case together, represent an optionally substituted alkylene chain having 3 or 4 members in which one or two (non-adjacent) carbon atoms can be replaced by oxygen atoms, --CO--R.sup.9 or ##STR4## where Y represents oxygen or sulphur and represent alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkenyl, halogenoalkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, amino, alkylamino, dialkylamino, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted cycloalkylthio, optionally substituted cycloalkylamino, optionally substituted dicycloalkylamino or an optionally substituted saturated or unsaturated heterocyclic radical, or bonded represent an optionally substituted heterocyclic radical, and
Furthermore, it has been found that halogenobenzimidazoles of the formula (I) and their acid addition salts and metal salt complexes are obtained when ##STR5## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 and X have the abovementioned meanings, in the presence of a diluent, subjected to an addition reaction with an acid or a metal salt.
Finally, it has been found that the halogenobenzimidazoles of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be employed both in crop protection and in the protection of materials.
Surprisingly, the substances according to the invention display a better fungicidal activity than 2-cyano-3-dimethylaminosulphonyl-6,6,7,7-tetrafluoro-[1,4]-dioxino[2,3-f]b enzimidazole and 2-cyano-6,6-difluoro-2-dimethylaminosulphonyl-[1,3]-dioxolo[4,5-f]benzimid azole, which are prior-art active compounds of similar constitution and the same direction of action.
Formula (I) provides a general definition of the substances according to the invention. preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain
REFERENCES:
patent: 3988465 (1976-10-01), Rochling
patent: 5510364 (1996-04-01), Lunkenheimer, et al.
patent: 5585395 (1996-12-01), Lunkenheimer, et al.
Cram and Hammond, "Organic Chemistry", McGraw-Hill Book Co., NY (1964) 2nd Ed., pp. 565-567.
Chemical Abstracts, vol. 114, No. 15, Apr. 15, 1991, Abstract No. 143420v, M.W. Moon, et al. "Preparation o aminoheterocycloquinolines . . . agents", p. 785; Chemical Abstracts, Chemical Substances, 12th Collective Index, vol. 106-115, 1987-1991, Seite 13453CS: die Verbindugen mit den RN [132873-97-3] und [132873-96-2] & WO 90 15058 A (Upjohn Co.) Dec. 13, 1990.
Journal of Organic Chemistry, Bd. 49, Nr. 12, Jun. 15, 1984, Easton US, p. 2158-2164, XP002019110, T.M. Stevenson, et al.: "Defined Dimensional Alterations . . . lin-Naphthoadenosine", p. 2159; Spalte 1, Schema 1, die Verbindung Nr. 10.
Journal of the Chemical Society, 1963, Letchworth, GB, p. 2930-2937, XP002019111, D. Harrison, et al.: "Some 1- and 2-Halogenobenzimidazoles." p. 2936, Absatz 8.
Assmann Lutz
Marhold Albrecht
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Morris Patricia L.
LandOfFree
Halobenzimidazoles and their use as microbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Halobenzimidazoles and their use as microbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Halobenzimidazoles and their use as microbicides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-937858