Substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal...

Details Substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal... Substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal...

1999-06-23

2003-06-10

O'Sullivan, Peter (Department: 1621)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S288000, C504S290000, C504S292000, C504S293000, C504S310000, C504S343000, C504S348000, C504S349000, C549S014000, C549S022000, C549S372000, C549S425000, C558S422000, C564S251000, C564S300000

Reexamination Certificate

active

06576596

ABSTRACT:

The present invention relates to substituted 2-benzoyl-cyclohexane-1,3-diones of the formula I
where:
R
1
and R
2
are are each hydrogen, nitro, halogen, cyano, thiocyanato, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, —OR
5
, —OCOR
6
, —OSO
2
R
6
, —SH, —S(O)
n
R
7
, —SO
2
OR
5
, —SO
2
NR
5
R
8
, —NR
8
SO
2
R
6
or —NR
8
COR
6
;
R
3
is hydrogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, —OR
7
, —SR
7
or —NR
7
R
10
;
R
4
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
4
-C
6
-cycloalkenyl, C
3
-C
6
-alkynyl, —COR
9
, —CO
2
R
9
, —COSR
9
or —CONR
8
R
9
, where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned and R
9
of the radicals —COR
9
, —CO
2
R
9
, —COSR
9
and —CONR
8
R
9
may be partially or fully halogenated and/or carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R
10
, —OR
10
, —SR
10
, —NR
8
R
10
, ═NOR
10
, —OCOR
10
, —SCOR
10
, —NR
8
COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
8
R
10
, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted;
X is oxygen or NR
8
:
n is 0, 1 or 2;
R
5
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
6
is C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
7
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
8
is hydrogen or C
1
-C
6
-alkyl;
R
9
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, phenyl or benzyl;
R
10
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
Q is a cyclohexane-1,3-dione ring attached in position 2 with or without substitution;
and agriculturally useful salts thereof.
The invention additionally relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I or of compositions comprising them for controlling harmful plants.
2-Benzoylcyclohexane-1,3-diones are known from the literature, for example from EP-A 278 742, EP-A 298 680, EP-A 320 864 and WO 96/14285.
However, the herbicidal properties of these prior art compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.
We have found that this object is achieved by the 2-benzoyl-cyclohexane-1,3-diones of the formula I and their herbicidal action.
Furthermore, the invention provides herbicidal compositions comprising the compounds I and having a very good herbicidal activity. Additionally, the invention provides processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
The present invention also provides stereoisomers of the compounds of the formula I. Pure stereoisomers and also mixtures thereof are included.
The compounds of the formula I contain a carbon-nitrogen double bond and are therefore present as E isomers or Z isomers or as E/Z isomer mixtures. Furthermore, the compounds of the formula I may contain further carbon-carbon or carbon-nitrogen double bonds. The invention provides the pure geometric isomers and also mixtures thereof.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as mixtures of enantiomers or diastereomers. The invention provides the pure enantiomers or diastereomers and also mixtures thereof.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid additon salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.
Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms may be replaced by C
1
-C
4
-alkyl or hydroxyl-C
1
-C
4
-alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of usable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Emphasis is given to compounds of the formula I according to the invention where the variable Q is a cyclohexane-1,3-dione ring of the formula II linked in position 2
where II also represents the tautomeric formulae II′ and II″,
where
R
11
, R
12
, R
14
and R
16
are each hydrogen or C
1
-C
4
-alkyl;
R
13
is hydrogen, C
1
-C
4
-alkyl or C
3
-C
4
-cycloalkyl, where the last two groups may carry one to three of the following substituents: halogen, C
1
-C
4
-alkylthio or C
1
-C
4
-alkoxy; or
is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl; 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the last 6 radicals mentioned may be substituted by one to three C
1
-C
4
-alkyl radicals;
R
15
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
6
-alkoxycarbonyl; or
R
13
and R
16
together form a &pgr;-bond or a three- to six-membered carbocylic ring; or
the CR
13
R
14
unit is replaced by C═O.
Emphasis is also given to compounds of the formula I according to the invention where
R
4
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
4
-C
6
-cycloalkenyl, C
3
-C
6
-alkynyl, —COR
9
, —CO
2
R
9
, —COSR
9
or —CONR
8
R
9
where the alkyl, cycloalkyl, alkenyl-, cycloalkenyl and alkynyl radicals mentioned and R
9
of the radicals —COR
9
, —CO
2
R
9
, —COSR
9
and —CONR
8
R
9
may be partially or fully halogenated and/or carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R
10
, —OR
10
, —SR
10
, —NR
8
R
10
, ═NOR
10
, —OCOR
10
, —SCOR
10
, —NR
8
COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
8
R
10
, C
1
-C
4
-alkyliminooxy, C
1
-C
4
-alkoxyamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxy-C
2
-C
6
-alkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be partially or fully halogenated and/or carry one to three radicals from the following group:
nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkoxycarbonyl.
The organic moieties mentioned for the substituents R
1
-R
16
or as radicals on phenyl, hetaryl and heterocylyl rings represent collective terms for lists of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylthio, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl and alkynyl moieties, may be straight-chain or branched. Unless stated otherwise, preference is given to halogenated substituents carrying one to five identical or different halogens. Halogen is in each case fluorine, chlorine, bromine or iodine.
Furthermore, the following moities repre

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