Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-12-08
2000-03-28
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5143164, 5143251, 548111, C07D41312, C07D40112, A01N 4380, A01N 4358
Patent
active
060433779
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel imidazole derivatives, to a plurality of processes for their preparation and to their use as microbicides in crop protection and in the protection of materials.
BACKGROUND OF THE INVENTION
It is already known that certain imidazole derivatives have fungicidal properties (cf. EP-A 0 298 196). Thus, for example, 4-chloro-2-cyano-1-morpholine-N-ylsulphonyl-5-phenylimidazole or 4-chloro-2-cyano-5-phenyl-1-(2-thienylsulphonyl)-imidazole can be employed for controlling fungi. The activity of these substances 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 imidazole derivatives of the formula ##STR2## in which R.sup.1 and R.sup.2 are identical or different and independently of one another each represent hydrogen, halogen, cyano, thiocyanato, nitro, formyl, carboxyl, carbamoyl, thiocarbamoyl, alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl, halogenoalkenyl, halogenoalkenyloxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, alkoxinminoalkyl, cycloalkyl, alkylamino, hydroxyalkylaamino, dialkylamino, hydroximinoalkyl or represent Z-R.sup.4, where --*CH.sub.2 --Q--, --Q*--CH.sub.2 --, --*CQ--Q--CH.sub.2 --, --*CH.sub.2 --Q--CQ--, --*Q--CQ--CH.sub.2 --, --*Q--CQ--Q--CH.sub.2 --, --S(O).sub.n --, --*CH.sub.2 --S(O).sub.n --, --CQ-- or --*S(O).sub.n --CH.sub.2 --, in which case attached to R.sup.4, heterocyclyl, thiocyanato or the grouping ##STR3## in which R.sup.5 represents alkyl, ##STR4## in which Y represents oxygen or sulphur and radical which contains at least one nitrogen or oxygen atom, and halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkenyl, halogenoalkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, amino which is optionally substituted by alkyl, cycloalkyl or aryl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted cycloalkylthio, optionally substituted cycloalkylamnino or represent an optionally substituted, saturated or unsaturated heterocyclic radical, or attached represent an optionally substituted heterocyclic radical,
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with hetero atoms, such as in alkoxy, alkylthio or alkylamino.
Furthermore, it has been found that imidazole derivatives of the formula (I) and also their acid addition salts and metal salt complexes are obtained when ##STR5## in which R.sup.1 and R.sup.2 are each as defined above and are reacted with halides of the formula presence of a diluent, ##STR6## in which R.sup.1, R.sup.2 and A are each as defined above are reacted with hydrogen sulphide, if appropriate in the presence of a base and if appropriate in the presence of a diluent, or when ##STR7## in which R.sup.1, R.sup.2 and A are each as defined above are reacted with alkylating agents of the formula presence of a diluent, compounds of the formula (I).
Finally, it has been found that the imidazole derivatives of the formula (I) and also 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 for controlling undesirable microorganisms.
Surprisingly, the substances according to the invention have better fungicidal activity than 4-chloro-2-cyano-1-morpholine-N-ylsulphonyl-5-phenylimidazole or 4-chloro-2-cyano-5-phenyl-1-(2-thienylsulphonyl)-imidazole, which are constitutionally similar prior-art active compounds of the same direction of action.
The formula (I) provides a general definition of the substances according to the invention. ano
REFERENCES:
patent: 3519639 (1970-07-01), Budde et al.
patent: 3595873 (1971-07-01), Budde et al.
patent: 4179277 (1979-12-01), Beck et al.
patent: 4369186 (1983-01-01), Beck et al.
patent: 4734427 (1988-03-01), Riebel et al.
patent: 4804673 (1989-02-01), Saito et al.
patent: 4995898 (1991-02-01), Nasu et al.
patent: 5045557 (1991-09-01), Buss et al.
patent: 5096915 (1992-03-01), Parsons et al.
Patent Abstracts of Japan, vol. 11, No. 369 (C-461) Dec. 2, 1987 & JP 62 142164 A (Ishihara Sangyo Kaisha Ltd.) Jun. 25, 1987.
Patent Abstracts of Japan, vol. 18, No. 19(C-1152), Jan. 13, 1994 & JP 05 255269 A (Agro Kanesho Co. Ltd.) Oct. 5, 1993.
Chem. Ber. (month unavailable) 1877, vol. 10, 1365-1375 (see p. 1370), Wyss.
J. Heterocycl. Chem. (Sep. 1967) vol. 4, 399-402, Lutz et al.
Chem. Ber. (month unavailable) 1976, vol. 109, 1625-1637, Buchel et al.
J. Chem. Soc. (month unavailable) 1910, vol. 97, 1814-1832-(see p. 1824), Pyman.
J. Chem. Soc. Parkin Trans., I, (month unavailable) 1989, pp. 95-99, Palmer et al.
ACS Symp. Ser. (month unavailable) 1995, (Synthesis and Chemistry of Agrochemicals IV), pp. 375-383, Riordan et al.
Tetrahedron (month unavailable) 1994, vol. 50, No. 19, pp. 5741-5752, Suwinski et al.
Synlett, Apr. 1990, (5), pp. 277-278, Dudfield et al.
J. Heterocyclic Chem., Aug. 1981, pp. 997-1006, Cremlyn et al.
Assmann Lutz
Elbe Hans-Ludwig
Heil Markus
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Gil Joseph C.
Higel Floyd D.
Marmo Carol
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