Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-02-02
2000-10-10
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544215, 544309, 544310, 544311, 544312, 544313, 544314, 546290, 548135, 548136, 548182, 548206, 548225, 548243, 548259, 5482632, 548541, 549 62, 549475, A61K 31506, A61K 31513, C07D23954
Patent
active
061302252
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel substituted p-trifluoromethylphenyluracils, to a process for their preparation and to their use as herbicides.
It is known that certain substituted p-trifluoromethylphenyluracils, such as, for example, the compound 3-(3-chloro-4-trifluoromethyl-phenyl)-6-(2,6-difluoro-phenyl)-[1H,3H]-pyri midine-2,4-dione, have pesticidal properties, i.e. they are active against certain animal pests, in particular against insects and mites (cf. JP 05025142--cited in Chem. Abstracts 119:117269). However, nothing has yet been disclosed about a herbicidal activity of these compounds.
This invention, accordingly, provides the novel substituted p-trifluoromethylphenyluracils of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen, cyano or halogen, --CO-- or the grouping --N-A.sup.4 - in which A.sup.4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, each of which is optionally substituted by halogen, --CO-- or the grouping --N-A.sup.4 - in which A.sup.4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, each of which is optionally substituted by halogen, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chorosulphonyl, halogen, represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which is optionally substituted by halogen or alkoxy, represents alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which is optionally substituted by halogen, represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which is optionally substituted by halogen, cyano, carboxyl, alkyl and/or alkoxy-carbonyl, or represents aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen, alkyl, halogenoalkyl, alkyloxy, halogenoalkyloxy and/or alkoxy-carbonyl, hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolalkyl, thiazolalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy, alkyl, halogen- or alkoxy-substituted alkyl.
The novel substituted p-trifluoromethylphenyluracils of the general formula (I) are obtained when ##STR2## in which R.sup.3 and R.sup.4 are each as defined above and (III) ##STR3## in which R.sup.1 and R.sup.2 are each as defined above (p-trifluoromethylphenylcarbamates) of the general formula (IV) ##STR4## in which R.sup.1 and R.sup.2 are each as defined above and in the presence of a diluent, definitions of substituents are carried out by customary methods on the resulting compounds of the formula (I).
The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definitions of substituents, for example by customary electrophilic or nucleophilic substitution reactions (for example R.sup.2 : F.fwdarw.OH, SH, NH.sub.2, OCH.sub.3, SC.sub.2 H.sub.5, NHC.sub.3 H.sub.7 -i, NHSO.sub.2 CH.sub.3 ; R.sup.5 : H.fwdarw.NH.sub.2, CH.sub.3)--cf. also the preparation examples.
The novel substituted p-trifluoromethylphenyluracils of the general formula (I) have strong herbicidal activity. Additionally, they are well tolerated by important crop plants, such as, for example, wheat, barley and maize.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl--also in combination with heteroatoms, such as in alkoxy or a
REFERENCES:
patent: 3869457 (1975-03-01), Lutz et al.
patent: 5116404 (1992-05-01), Ishii et al.
patent: 5681794 (1997-10-01), Andree et al.
Chem. Abstracts, vol. 119, No. 11, Abstract No. 117269m & JP 05 025142 Feb. 2, 1993.
J. Heterocycl. Chem. 9, pp. 513-522, (month unavailable) 1992.
Andree Roland
Dollinger Markus
Drewes Mark-Wilhelm
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Gil Joseph C.
Shah Mukund J.
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