Hetaroyl cyclohexanedione derivatives with herbicidal effect

Details Hetaroyl cyclohexanedione derivatives with herbicidal effect Hetaroyl cyclohexanedione derivatives with herbicidal effect

1999-03-17

2002-11-12

Huang, Evelyn Mei (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S141000, C546S142000, C546S146000, C546S153000, C546S156000, C546S166000, C546S168000

Reexamination Certificate

active

06479436

ABSTRACT:

The present invention relates to novel hetaroyl derivatives of the formula I
where:
R
1
and R
2
are each hydrogen, nitro, halogen, cyano, thiocyanato, hydroxyl, mercapto, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
2
-C
6
-alkenylthio, C
2
-C
6
-alkynylthio, C
1
-C
6
-alkylsulfinyl, C
l
-C
6
-haloalkylsulfinyl, C
2
-C
6
-alkenylsulfinyl, C
2
-C
6
-alkynylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, C
2
-C
6
-alkenylsulfonyl, C
2
-C
6
-alkynylsulfonyl, C
1
-C
6
-alkoxysulfonyl, C
1
-C
6
-haloalkoxysulfonyl, C
2
-C
6
-alkenyloxysulfonyl, C
2
-C
6
-alkynyloxysulfonyl, phenyl, phenyloxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the last five substituents may be partially or fully halogenated and may carry one to three of the following groups:
nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
Z is a building block from the group consisting of Z
1
to Z
12
.
 where
R
3
, R
5
, R
7
and R
9
are each hydrogen, halogen, C
1
-C-
4
-alkyl, C
1
-C-
4
-haloalkyl, C
1
-C-
4
-alkoxy, C
1
-C-
4
-haloalkoxy, C
1
-C-
4
-alkylthio, C
1
-C-
4
-haloalkythio, nitro, cyano, hydroxyl, mercapto, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, C
2
-C
4
-alkenyloxy, C
2
-C
4
-alkynyloxy, C
2
-C
4
-alkenylthio, C
2
-C
4
-alkynylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-haloalkylsulfinyl, C
2
-C
4
-alkenylsulfinyl, C
2
-C
4
-alkynylsulfinyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, C
2
-C
4
-alkenylsulfonyl, C
2
-C
4
-alkynylsulfonyl C
1
-C
4
-alkoxysulfonyl, C
1
-C
4
-haloalkoxysulfonyl, C
2
-C
4
-alkenyloxysulfonyl, C
2
-C
4
alkynyloxysulfonyl, —NR
12
R
13
, —CO
2
R
12
, —CONR
12
R
13
, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the last five substituents may be partially or fully halogenated and may carry one to three of the following groups:
nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
R
4
, R
6
, R
8
and R
10
are each hydrogen, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio or C
1
-C
4
-haloalkylthio;
or a —CR
3
R
4
—, —CR
5
R
6
—, —CR
7
R
8
— or —CR
9
R
10
— unit may be replaced by C═O or C═NR
13
;
R
11
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, —CO
2
R
12
, —CONR
12
R
13
or SO
2
R
12
;
R
12
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or phenyl, where the last radical may be partially or fully halogenated and may carry one to three of the following radicals:
nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy;
R
13
is C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy or one of the radicals mentioned under R
12
;
Q is an unsubstituted or substituted cyclohexane-1,3-dione ring linked through position 2;
and their agriculturally useful salts.
The invention additionally relates to processes for preparing compounds of the formula I, to compositions comprising compounds of the formula I and to the use of these derivatives or to compositions comprising these derivatives for controlling harmful plants.
2-Hetaroylcyclohexanediones are known from the literature, for example from EP-A 283 261.
However, the herbicidal properties of these prior art compounds and their compatibility with crop plants are not entirely satisfactory. It is therefore an object of the present invention to provide novel, in particular herbicidally active, compounds with improved properties.
We have found that this object is achieved by the hetaroyl derivatives 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 plant growth using the compounds I.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, be present as enantiomers or as mixtures of diastereomer. The invention provides the pure enantiomers or diastereomers and 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 addition 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 which may, if desired, carry one to four C
1
-C
4
-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropyl-ammonium, tetramethylammonium, tetrabutylammonium, trimethyl-benzylammonium, and further phosphonium ions and 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 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.
Particular preference is given to the compounds of the formula I according to the invention where the variable Q is a cyclohexane-1,3-dione ring, linked through position 2, of the formula II
where II also represents the tautomeric forms II′ and II″
where
R
14
, R
15
, R
17
and R
19
are each hydrogen or C
1
-C
4
-alkyl;
R
16
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-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-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 may be substituted by one to three C
1
-C
4
-alkyl radicals;
R
18
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
6
-alkoxycarbonyl; or
R
16
and R
19
together form a bond or a three- to six-membered carbocyclic ring; or
the —CR
16
R
17
— unit may be replaced by C═O.
The organic moieties mentioned for the substituents R
1
-R
19
or as radicals on phenyl rings represent collective terms for lists of the individual group members. All hydrocarbon chains, ie. all the alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxysulfonyl, haloalkoxysulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkenyloxysulfonyl, alkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl, alkynylsulfonyl and alkynyloxysulfonyl 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 moieties represent, for example:
C
1
-C
4
-alkyl and the alkyl moieties of C
1
-C
4
-alkylcarbonyl: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl and the alkyl moieties of C
1
-C
6
-alkylcarbonyl: C
1
-C
4
-alkyl as mentioned above, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1

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