3-aryluracils and intermediates for their preparation

Details 3-aryluracils and intermediates for their preparation 3-aryluracils and intermediates for their preparation

1997-08-26

2001-11-27

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C544S105000

Reexamination Certificate

active

06323154

ABSTRACT:

The present invention relates to novel 3-aryluracils of the general formula I
where the variables have the following meanings:
A is hydrogen, methyl oder amino;
R
1
is hydrogen or halogen;
R
2
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkythio, C
1
-C
6
-alkylsulfenyl or C
1
-C
6
-alkylsulfonyl;
R
3
is hydrogen, halogen or C
1
-C
6
-alkyl;
X is oxygen or —N(R
7
)—, R
7
being hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, (C
1
-C
6
-alkyl)carbonyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl;
Y
1
and Y
2
independently of one another are oxygen or sulfur;
Z is oxygen or —N(R
8
)—;
R
5
, R
6
, R
7
and R
8
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl;
or R
6
and R
8
together are a second chemical bond;
R
4
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, (C
1
-C
6
-alkyl)carbonyl, (C
3
-C
6
-alkenyl)carbonyl, (C
3
-C
6
-alkynyl)carbonyl or C
1
-C
6
-alkylsulfonyl, it being possible for each of the last-mentioned 9 radicals to carry, if desired, one to three substituents, in each case selected from the group consisting of
halogen, nitro, cyano, hydroxyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-alkoxy, C
3
-C
8
-cycloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfenyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylideneaminooxy,
the phenyl, phenoxy or phenylsulfonyl group, which can be unsubstituted or can carry one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-haloalkyl,
a 3- to 7-membered heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group having one to three hetero atoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, it being possible for the heterocycle to be saturated, partially or completely unsaturated or aromatic and, if desired, to carry one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkyl and (C
1
-C
6
-alkyl)-carbonyl,
a group —CO—R
9
, —O—CO—R
9
, —CO—OR
9
, —O—CO—OR
9
, —CO—SR
9
, —O—CO—SR
9
, —CO—N(R
9
)R
10
, —O—CO—N(R
9
)R
10
, —N(R
9
)R
10
or —C(NR″)—OR
12
,
R
9
being hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, phenyl or phenyl-C
1
-C
6
-alkyl, it being possible for the phenyl radicals to be unsubstituted or to carry one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-haloalkyl
R
10
being hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl or C
1
-C
6
-alkoxy, C
3
-C
6
alkenyloxy or (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkoxy
R
11
being C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy or (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkoxy
and
R
12
being C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or (C
1
-C
6
-alkoxy)-carbonyl-C
1
-C
1
-C
6
-alkyl
and the agriculturally utilizable salts of those compounds I in which A is hydrogen.
The invention additionally relates to
the use of the compounds I as herbicides and/or for the desiccation and/or defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active substances,
methods for controlling undesired vegetation and for the desiccation and/or defoliation of plants using the compounds I,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation and/or defoliation of plants using the compounds I, and
novel intermediates of the formulae IV, V, VIII, X and XII, from which the compounds I are obtainable.
EP-A 420 194 already describes compounds of the formulae IIa and IIIa
where R
a
is C
1
-C
7
-alkyl, C
3
-C
7
-alkenyl, C
3
-C
7
-alkynyl, halogen-C
1
-C
6
-alkyl, halogen-C
3
-C
6
-alkenyl or C
1
-C
4
-alkoxy-C
1
-C
3
-alkyl. The compounds IIa where A=methyl or amino and the compounds IIIa are ascribed herbicidal properties.
WO 90/15057 further discloses that, inter alia, compounds of the formula IIb
where
R
b
is, inter alia, hydrogen or C
1
-C
4
-alkyl;
R
c
is hydrogen or certain organic radicals bonded via carbon;
R
d
and R
e
are in each case hydrogen, halogen, C
1
-C
4
-alkyl or phenyl and
R
3
′ is hydrogen, halogen or C
1
-C
4
-alkyl, are also herbicidally active.
3-(3-oxo-2H-1,4-benzoxazin-6-yl)-6-haloalkyl-2,4-(1H, 3H)-pyrimidinedione derivatives of this type are further also disclosed in EP-A 408 382. They are described there as herbicides, together with compounds of the formulae IIIb and IIIc
where
R
f
is, inter alia, hydrogen or C
1
-C
3
-alkyl and
R
g
is hydrogen or certain organic radicals bonded via carbon.
According to the disclosure of U.S. Pat. No. 5,310,723, 3-(1-lower alkoxy-quinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracils, inter alia, are also herbicidally active.
Finally, EP-A 477 677 relates to 6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-, 6-(dimethylmaleimido)- and 6-(4,5,6,7-tetrahydroisoindol-2-yl)-1,4-benzoxazin-3(4H)-one derivatives which on the nitrogen of the oxazine ring carry a C
1-5
-alkoxy, C
3-4
-alkenyloxy, C
3-4
-alkynyloxy, cyclopropylmethoxy, C
2-3
-cyanoalkoxy, C
1-2
-alkoxy-C
1-2
-alkoxy or C
1-2
-alkylthio-C
1-2
-alkoxy group. Herbicidal properties are also indicated for these compounds.
The herbicidal properties of the known compounds, however, are not always completely satisfactory.
It is an object of the present invention to provide novel active compounds, in particular herbicidally active compounds, using which undesired plants can be specifically controlled better than previously. The object also extends to the provision of novel compounds having desiccant/defoliant activity.
We have found that this object is achieved by the 3-aryluracils of the formula I and their herbicidal action.
Herbicidal compositions have further been found which comprise the compounds I and have a very good herbicidal action. Processes for preparing these compositions and methods of controlling undesired plant growth using the compounds I have additionally been found.
In addition, it has been found that the compounds I are also suitable for the defoliation and desiccation of parts of plants, for which suitable crop plants are those such as cotton, potato, rape, sunflower, soybean or field beans, in particular cotton. With respect to this, compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and processes for the desiccation and/or defoliation of plants using the compounds I have been found.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers and then exist as enantiomer or diastereomer mixtures. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.
If A is hydrogen, the 3-aryluracils I can be present in the form of their agriculturally utilizable salts, the nature of the salt generally not mattering. In general, the salts of those bases are suitable in which the herbicidal action is not adversely affected in comparison with the free compound I.
Suitable basic salts are paticularly those of the alkali metals, preferably sodium and potassium salts, the alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and also ammonium salts in which the ammonium ion, if desired, can carry one to three C
1
-C
4
-alkyl or hydroxy-C
1
-C
4
-alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl-(2-hydroxyethyl)ammonium salts, in addition phosphonium salts, sulfonium salts su

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