Substituted 1-amino-3-phenyluracil derivatives, their preparatio

Details Substituted 1-amino-3-phenyluracil derivatives, their preparatio Substituted 1-amino-3-phenyluracil derivatives, their preparatio

1998-02-25

1999-12-28

Clardy, S. Mark

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544242, 544298, 544309, 544311, 544312, 504242, A01N 4354, C07D23902, C07D23900, C07D23954

Patent

active

060081600

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel substituted aminouracils, to the preparation thereof and to their use as herbicides.
Certain substituted uracils are known to have herbicidal properties (cf. EP 408382/U.S. Pat. No. 5,084,084/U.S. Pat. No. 5,127,935/U.S. Pat. No. 5,154,755/EP 563384/EP 648749/WO 91/00278/U.S. Pat. No. 4,979,982/U.S. Pat. No. 5,169,430). However, these compounds are of no particular importance.
This invention, accordingly, provides the novel substituted aminouracils of the general formula (I) ##STR2## in which
R.sup.1 represents hydrogen, cyano or halogen,
R.sup.2 represents cyano or thiocarbamoyl,
R.sup.3 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkylcarbonyl, alkenyl, alkenylcarbonyl, alkinyl, alkinylcarbonyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl, cycloalkylalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl and heterocyclylcarbonyl,
R.sup.4 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkylcarbonyl, alkenyl, alkenylcarbonyl, alkinyl, alkinylcarbonyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl, cycloalkylalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl and heterocyclylcarbonyl, or together with R.sup.3 represents respectively optionally substituted alkanediyl, oxoalkanediyl or dioxoalkanediyl,
R.sup.5 represents hydrogen, halogen or respectively optionally substituted alkyl or alkoxy,
R.sup.6 represents optionally substituted alkyl,
R.sup.7 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl and alkinyl, and
R.sup.8 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl and alkinyl.
The novel substituted aminouracils of the general formula (I) are obtained when aminouracils of the general formula (II) ##STR3## in which
R.sup.1, R.sup.2, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each as defined above and
Z represents optionally substituted alkylsulphonylamino or the grouping NR.sup.3 R.sup.4, where R.sup.3 and R.sup.4 are each as defined above, (III), (IV), (V) or (VI)
R.sup.3 and R.sup.4 are each as defined above, in the presence of a diluent.
The compounds of the general formula (I) can be converted by conventional methods into other compounds of the general formula (I) according to the definition above, for example by deacylation with ammonium acetate/glacial acetic acid (R.sup.3 /R.sup.4 : --CO--CH.sub.3 .fwdarw.H) or by the addition of hydrogen sulphide (R.sup.2 : CN.fwdarw.CSNH.sub.2).
The novel substituted aminouracils of the general formula (I) have strong herbicidal properties.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R.sup.1 represents hydrogen, cyano, fluorine or chlorine,
R.sup.2 represents cyano or thiocarbamoyl,
R.sup.3 represents hydrogen or represents respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.4 -alkyl-carbonyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted alkyl, alkylcarbonyl, alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonyl having in each case up to 10 carbon atoms in the alkyl, alkenyl or alkinyl moieties,
R.sup.3 furthermore represents respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.4 -alkyl-carbonyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl or cycloalkylalkylcarbonyl having in each case 3 to 8 carbon atoms in the cycloalkyl moiety and optionally up to 4 carbon atoms in the alkyl moiety,
R.sup.3 furthermore represents arylcarbonyl or

REFERENCES:
patent: 5116404 (1992-05-01), Ishii et al.
patent: 5593945 (1997-01-01), Andree et al.
patent: 5681794 (1997-10-01), Andree et al.

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