3-(4-cyanophenyl) uracils

Details 3-(4-cyanophenyl) uracils 3-(4-cyanophenyl) uracils

2002-12-20

2003-12-02

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S312000

Reexamination Certificate

active

06656884

ABSTRACT:

The present invention relates to novel 3-(4-cyanophenyl)uracils of the general formula I
where the variables have the following meanings:
A is hydrogen, methyl or amino;
Y is oxygen or sulfur;
R
1
is hydrogen or halogen;
R
2
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-
6
-haloalkyl, C
1
-
6
-alkylthio, C
1
-C
6
-alkylsulfenyl or C
1
-C
6
-alkylsulfonyl;
R
3
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
4
is hydrogen, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkyl, C
3
-C
8
-cyclo-alkyl, 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 alkylsulfonyl, it being possible, if desired, for each of the last-mentioned 8 radicals to have attached to it 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
-alkylideneaminoxy,
the phenyl, phenoxy or phenylsulfonyl group which can be unsubstituted or have attached to it 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 and C
1
-C
6
-haloalkyl,
a 3- to 7-membered heterocyclyl or heterocyclyloxy group having one to three hetero atoms 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 fully unsaturated or aromatic and, if desired, to have attached to it 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—XR
5
, —OCO—XR
5
or —N(R
5
)R
6
where
X is a chemical bond, oxygen, sulfur or —N(R
6
)—;
R
5
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C6-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 group and the phenyl ring of the phenylalkyl group to be unsubstituted or to have attached to it 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
-haloalkyl, C
1
-C
6
-alkoxy and (C
1
-C
6
-alkyl)carbonyl or
X and R
5
together form a 3- to 7-membered heterocycle, bonded via nitrogen and having one to three hetero atoms 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 fully unsaturated or aromatic and, if desired, to have attached to it 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
-haloalkyl C
1
-C
6
-alkoxy and (C
1
-C
6
-alkyl)carbonyl; and
R
6
represents hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl or C
1
-C
6
-alkoxy, and the agriculturally useful salts of those compounds I where A is hydrogen.
The invention furthermore 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 desiccating and/or defoliating plants which comprise the compounds I as active ingredients,
methods of controlling undesirable vegetation and for desiccating and/or defoliating plants using the compounds I,
processes for the preparation of the compounds I and of herbicidal compositions and compositions for desiccating and/or defoliating plants using the compounds I, and
novel intermediates of the formulae III and IV from which the compounds I are obtainable.
Regarding the compounds I where A=hydrogen or methyl, EP-A 255 047 is of particular importance since it discloses quite generally 3-aryluracils of the formula II
where R
a
is hydrogen, C
1-4
-alkyl, C
1-4
-haloalkyl, formyl or C
2-6
-alkanoyl,
R
b
is C
1-4
-alkyl or C
1-4
-haloalkyl,
R
3
′ is hydrogen, halogen or C
1
-C
4
-alkyl,
R
c
is an ether group or a radical R—CO—O—, R—CS—O— or R—SO
2
—O— and
R
d
is halogen or cyano
and the salts of the compounds II where R
a
=hydrogen, as herbicides.
Examples of 3-phenyluracils in which the phenyl ring carries a cyano group para to the uracil radical (R
d
), and their herbicidal action, however, are not revealed by this document.
Certain 1-amino-3-phenyluracils which, however, do not carry a cyano group on the phenyl ring have already been disclosed as herbicides in EP-A-517 181 and JP-A 05/025 143.
However, the herbicidal or desiccant/defoliant properties of the known compounds are not always entirely satisfactory.
It was therefore an object of the present invention to provide novel, in particular herbicidally active compounds, which allow better, tailored control of undesirable plants than this was possible to date.
The object also extends to the provision of novel compounds which act as desiccants/defoliants.
We have found that this object is achieved by the 3-(4-cyanophenyl)uracils of the formula I and their herbicidal action.
There have furthermore been found herbicidal compositions which comprise the compounds I and have a very good herbicidal action. There have also been found processes for preparing these compositions and methods of controlling undesirable vegetation using the compounds I.
It has furthermore been found that the compounds I are also suitable for defoliating and desiccating parts of plants, suitable plants being crop plants such as cotton, potatoes, oilseed rape, sunflowers, soybeans or field beans, in particular cotton. Thus, there have been found compositions for the desiccation and/or defoliation of plants, processes for the preparation of these compositions, and methods of desiccating and/or defoliating plants using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can have one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. The invention relates to the pure enantiomers or diastereomers and to their mixtures.
If A is hydrogen, the 3-(4-cyanophenyl)uracils I can be present in the form of their agriculturally useful salts, the type of salt not being critical, as a rule. In general, suitable salts are salts of those bases which do not adversely affect the herbicidal action in comparison with the free compounds I.
Particularly suitable basic salts are those of the alkali metals, preferably sodium and potassium salts, of the alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and also ammonium salts where, if desired, the ammonium ion can have attached to it 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, furthermore phosphonium salts, sulfonium salts, such as, preferably, tri(C
1
-C
4
-alkyl)sulfonium salts, and sulfoxonium salts, such as, preferably, tri(C
1
-C
4
-alkyl)sulfoxonium salts.
The organic moieties mentioned for the substituents R
1
to R
6
or as radicals on phenyl rings or heterocycles are—like the meaning halogen—collective terms for individual enumerations of the individual group members. All carbon chains, ie. all alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfenyl, alkylsulfonyl, alkylcarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl and alkylideneaminoxy moieties can be straight-chain or branched. Unless otherwise indicated, halogenated substituents preferably have attached to them one to five identical or different halogen atoms.
Examples of individual meanings are:
halogen: fluorine, chlorine, bromine or iodine;
C
1
-C
4
-alkyl and the alkyl moieties of C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl and (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl: methyl,

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