Substituted phenyluracils

Details Substituted phenyluracils Substituted phenyluracils

2001-01-16

2002-09-24

Ford, John M. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S310000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06455697

ABSTRACT:

The invention relates to novel substituted phenyluracils, to processes for their preparation, to novel intermediates and to their use as herbicides.
It is known that certain substituted uracils 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 5,63,384, EP 648749, WO 91/00278, U.S. Pat. No. 4,979,982, U.S. Pat. No. 5,169,430, DE 4329537). However, these compounds have hitherto not attained any major importance.
This invention, accordingly, provides the novel substituted phenyluracils of the general formula (I)
in which
R
1
represents hydrogen, halogen or optionally substituted alkyl,
R
2
represents optionally substituted alkyl,
R
3
represents hydrogen, amino or respectively optionally substituted alkyl, alkenyl or alkinyl,
R
4
represents hydrogen, cyano or halogen,
R
5
represents cyano or thiocarbamoyl, and
R
6
represents one of the groupings below
—C(R
7
,R
8
)—C(R
7
,R
8
)—R
9
or —C(R
7
)═C(R
8
)—R
9
 in which
R
7
and R
8
are identical or different and each represents independently of the other hydrogen, hydroxyl, mercapto, halogen or respectively optionally substituted alkyl, alkoxy or alkylthio, and
R
9
represents cyano, formyl, alkylcarbonyl, the grouping —CO—OR
10
or the grouping —CO—N(R
11
,R
12
), where
R
10
represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl and heterocyclylalkyl,
R
11
represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkoxy, alkenyl and alkinyl, and
R
12
represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl and heterocyclylalkyl, or together with R
11
represents alkanediyl.
The novel substituted phenyluracils of the general formula (I) are obtained when
(a) aminophenyluracils of the general formula (II)
in which
R
1
, R
2
, R
3
, R
4
and R
5
are each as defined above,
or acid adducts of compounds of the formula (II)
are reacted with an alkali metal nitrite or alkyl nitrite and with a hydrogen halide (HX
1
) or a metal halide (MX
1
), if appropriate in the presence of a diluent, and the resulting diazonium salts of the general formula (III)
in which
R
1
, R
2
, R
3
, R
4
and R
5
are each as defined above and
X
1
represents halogen,
are reacted with acrylic acid derivatives of the general formula (IV)
C(R
7
R
8
)═C(R
7
)—R
9
  (IV)
in which
R
7
, R
8
and R
9
are each as defined above,
in the presence of hydrogen halides (HX
1
), if appropriate in the presence of catalysts, if appropriate in the presence of water and if appropriate in the presence of the organic solvent employed initially, or
(b) substituted phenyluracils of the general formula (Ia)
in which
R
1
, R
2
, R
3
, R
4
, R
5
, R
7
, R
8
and R
9
are each as defined above,
but where at least one of the radicals R
7
/R
8
represents hydrogen and at least one further radical R
7
/R
8
in a position vicinal to the first represents halogen
are reacted with an acid acceptor, if appropriate in the presence of a diluent.
It is also possible to convert the compounds of the general formula (I) into other compounds of the general formula (I) according to the above definition using other conventional methods, for example by amination or alkylation (e.g. R
3
: H→NH
2
, H→CH
3
), reaction with hydrogen sulphide (e.g. R
5
: CN→CSNH
2
), nucleophilic substitution (e.g. R
8
: Cl→SCH
3
), if appropriate addition of hydrogen, halogen or hydrogen halide to a C—C double bond (cf. definition of R
6
), hydrolysis (e.g. R
9
: CN→COOH).
If the compounds of the formula (I) according to the invention contain olefinic double bonds (cf. definition of R
6
), the invention relates both to the individual E and Z or cis and trans isomers separable by conventional methods, and also to any mixtures of these isomers.
The novel substituted phenyluracils of the general formula (I) have strong herbicidal activity.
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
1
represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkyl,
R
2
represents optionally fluorine- and/or chlorine-substituted C
1
-C
4
-alkyl,
R
3
represents hydrogen, amino, represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl or represents optionally fluorine- and/or chlorine-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl,
R
4
represents hydrogen, cyano, fluorine or chlorine,
R
5
represents cyano or thiocarbamoyl, and
R
6
represents one of the groupings below
—C(R
7
,R
8
)—C(R
7
,R
8
)—R
9
or —C(R
7
)═C(R
8
)—R
9
 in which
R
7
and R
8
are identical or different and each represents independently of the other hydrogen, hydroxyl, mercapto, fluorine, chlorine, bromine or respectively optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-alkylthio, and
R
9
represents cyano, formyl, C
1
-C
4
-alkyl-carbonyl, the grouping —CO—OR
10
or the grouping —CO—N(R
11
,R
12
), where
R
10
represents hydrogen or represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
10
-alkyl,
R
10
furthermore represents respectively optionally fluorine-, chlorine- or bromine-substituted C
3
-C
10
-alkenyl or C
3
-C
10
-alkinyl,
R
10
furthermore represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-carbonyl-substituted C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl,
R
10
furthermore represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio- or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl, phenyl- C
1
-C
4
-alkyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxaazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl, thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl,
R
11
represents hydrogen or represents respectively optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy,
R
11
furthermore represents respectively optionally fluorine-, chlorine- or bromine-substituted C
3
-C
6
-alkenyl or C
3
-C
6
-alkinyl, and
R
12
represents hydrogen or represents optionally cyano-, fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted C
1
-C
10
-alkyl,
R
12
furthermore represents respectively optionally fluorine-, chlorine- or bromine-substituted C
3
-C
10
-alkenyl or C
3
-C
10
-alkinyl,
R
12
furthermore represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-carbonyl-substituted C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl,
R
12
furthermore represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio- or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl, phenyl-C
1
-C
4
-alkyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxadiazolylmethyl, thi

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