Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-12-11
2000-08-15
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544280, C07D48704, A01N 4390
Patent
active
061037265
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to the use of Pyrrolopyrimidines, some of which are known, for controlling harmful plants and animals. Additionally, the invention also relates to novel pyrrolopyrimidines and to a process for their preparation.
BACKGROUND OF THE INVENTION
It is already known that certain pyrrolopyrimidines have pharmacological properties (cf. J. Med. Chem. 1995, (38), 3884-3888). However, a fungicidal or insecticidal activity of these compounds has hitherto not been described.
It has now been found that the pyrrolopyrimidines of the formula ##STR2## in which R.sup.1 represents halogen, alkoxy or halogenoalkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, substituted heteroaryl, halogen or alkyl and one or more heteroatoms or heteroatom groups, where the heteroatoms are not adjacent if a plurality of heteroatoms is present, suitable for controlling harmful plants and animals.
Surprisingly, the substances which can be used according to the invention have considerably better activity against harmful plants and animals than the constitutionally most similar compounds of the prior art having the same direction of action.
The formula (I) provides a general definition of the pyrrolopyrimidines which can be used according to the invention. having 1 to 4 carbon atoms or halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms. iodine, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms or halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms. represents heteroaryl having 3 to 12 ring members, where these radicals may in each case be mono- to pentasubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl; case 1 to 5 carbon atoms; halogenoalkylsulphonyl having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms; halogenoalkenyloxy having in each case 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms; hydroxirninoalkyl, alkoximinoalkyl or cyanirmino(alkoxy)alkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties; or alkylene having 3 or 4 carbon atoms with which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms; ##STR3## and also phenyl or phenoxy, where these two radicals may for their part be mono- to pentasubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carbamoyl, thiocarbamoyl, alkyl having 1 to 5 carbon atoms, phenyl; halogen atoms; to 4 carbon atoms and 1 to 5 identical or different halogen atoms; or alkylene having 3 to 4 carbon atoms which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms. hydrogen, fluorine, chlorine, bromine, iodine or alkyl having 1 to 4 carbon atoms. alkanediyl having 1 to 8 chain members, where 1 or 2 (non-adjacent) chain members are replaced by oxygen, sulphur and/or SO.sub.2 and where a termninal oxygen or sulphur atom or an SO.sub.2 group is in each case attached to a radical R.sup.3.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as an alkoxy, alkylthio or alkylamino. methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,
REFERENCES:
Renau et al., J. Med. Chem. 1996, 39, 3470-3476.
J. Med. Chem, 1995, 38, 3884-3888.
Chem. Ber., 1942, 75, p. 755.
J. Org. Chem., Oct. 1961, 26, p. 3809.
Chem. Ber., (month unavailable) 1979, 112, p. 3432.
Chem. Ber. (month unavailable) 1979, 112, 799.
Liebigs Ann. Chem. (month unavailable) 1984, pp. 273-282.
Liebigs Ann. Chem. (month unavailable) 1984, pp. 722-733.
Liebigs Ann. Chem. (month unavailable) 1985, pp. 312-320.
J. Med. Chem. (month unavailable) 1985, 28, pp. 1462-1467.
Renau et al., Chem. Abstract: 125:275786 (1996).
Altmann et al., Chem. Abstract: 127:293238 (1997).
Yamada et al., Chem. Abstract:121:230784 (1994).
Dutzmann Stefan
Erdelen Christoph
Kuhnt Dietmar
Markert Robert
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Jayaram B
Marmo Carol
Raymond Richard L.
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