Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones

Details Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones

1999-11-02

2002-04-16

Padmanabhan, Sreeni (Department: 1621)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S130000, C504S131000, C504S136000, C504S137000, C504S139000, C504S141000, C504S189000, C504S349000, C504S350000, C558S415000, C558S416000, C568S314000, C568S319000, C568S322000, C568S329000, C568S331000, C544S242000, C546S341000, C546S351000, C546S352000, C548S215000, C548S341500, C548S373100, C549S029000, C549S080000, C549S369000, C549S506000

Reexamination Certificate

active

06372693

ABSTRACT:

The present invention relates to 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I
where the variables have the following meanings:
R
1
, R
2
are 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
6
, —OCOR
7
, —OSO
2
R
7
, —SH, —S(O)
n
R
8
, —SO
2
OR
6
, —SO
2
NR
6
R
9
, —NR
9
SO
2
R
7
or —NR
9
COR
7
;
R
3
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl;
R
4
, R
5
are hydrogen, nitro, halogen, cyano, thiocyanato, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
4
-C
6
-cycloalkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkoxy, —COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
10
R
11
, —C(R
12
)═NR
13
, —PO(OR
10
)(OR
11
), C
1
-C
4
-alkyl which has attached to it a radical from amongst the following group: hydroxyl, —COR
10
, —CO
2
R
10
, —COSR
10
, —CONR
10
R
11
or —C(R
12
)═NR
13
; heterocyclyl, heterocyclyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, hetaryl, hetaryl-C
1
-C
4
-alkyl, it being possible for the six last-mentioned radicals to be substituted; or
R
4
and R
5
together form a C
2
-C
6
-alkanediyl chain which can be mono- to tetrasubstituted by C
1
-C
4
-alkyl and/or can be interrupted by oxygen or sulfur or by a nitrogen which is unsubstituted or substituted by C
1
-C
4
-alkyl;
n is 0, 1 or 2;
R
6
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
7
is C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
8
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
9
is hydrogen or C
1
-C
6
-alkyl;
R
10
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, phenyl or benzyl, it being possible for the two last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst 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
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
R
11
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl; or
R
10
and R
11
together form a C
2
-C
6
-alkanediyl chain which can be mono- to tetrasubstituted by C
1
-C
4
-alkyl and/or can be interrupted by oxygen or sulfur or by a nitrogen which is unsubstituted or substituted by C
1
-C
4
-alkyl;
R
12
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl or benzyl, it being possible for the two last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst the following group: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
l
-C
4
-haloalkoxy, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
R
13
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
—C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, phenyl, benzyl or phenyl-C
1
-C
4
-alkoxy, it being possible for the three last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst 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
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
Q is an unsubstituted or substituted cyclohexane-1,3-dione ring which is linked in the 2-position;
and to agriculturally useful salts thereof.
The invention furthermore relates to processes for the preparation of compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I and to compositions comprising them for controlling harmful plants.
WO 93/24446 discloses cyclohexane-1,3-diones which are substituted in the 2-position and which have anthelminthic and nematicidal properties. 2-Benzoylcyclohexane-1,3-diones are also known from the literature, for example from EP-A 135 191, EP-A 137 963 and EP-A 319 075. However, the herbicidal properties of these compounds and their crop plant tolerance are only moderately satisfactory.
It is an object of the present invention to find, in particular, herbicidally active compounds which have improved properties.
We have found that this object is achieved by the 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I and their herbicidal action.
We have furthermore found highly active herbicidal compositions which comprise the compounds I. In addition, we have found processes for the preparation of these compositions and methods of controlling undesired vegetation using the compounds I.
The present invention also relates to stereoisomers of the compounds of the formula I. This embraces not only pure stereoisomers, but also mixtures of these.
The compounds of the formula I contain a carbon-carbon double bond and are therefore present in the form of E isomers or Z isomers or E/Z; isomer mixtures. Furthermore, the compounds of the formula I can contain other carbon-carbon or carbon-nitrogen double bonds. The invention relates not only to the pure geometric isomers, but also to mixtures of these.
Equally, the compounds of the formula I can have one or more chiral centers, depending on the substitution pattern, in which case they exist as enantiomer or diastereomer mixtures. The invention relates not only to the pure enantiomers or diastereomers, but also to mixtures of these.
The compounds of the formula I can also exist in the form of their agriculturally useful salts, the type of salt generally being of no importance. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations, or anions, do not adversely affect the herbicidal action of the compounds I.
Cations which are suitable 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, zink and iron, and also ammonium, it being possible in this case, if desired, for one to four hydrogen atoms to be replaced by C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di-(2-hydroxyeth-1-yl)ammonium, 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 useful acid addition salts are mainly 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.
Mention must be made of the compounds of the formula I according to the invention where the variable Q is a cyclohexane-1,3-dione ring of the formula II
which is linked in the 2-position, II also representing the tautomeric formulae II′ and II″
where
R
14
, R
15
, R
17
and R
19
are hydrogen or C
1
-C
4
-alkyl;
R
16
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
3
-C
4
-cycloalkyl, it being possible for the three last-mentioned groups to have attached to them one to three of the following substituents: 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,

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