3-aminocarbonyl/3-aminothiocarbonyl-substituted...

Details 3-aminocarbonyl/3-aminothiocarbonyl-substituted... 3-aminocarbonyl/3-aminothiocarbonyl-substituted...

1999-06-23

2001-10-30

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C504S289000, C504S292000, C504S293000, C504S294000, C504S337000, C549S028000, C549S062000, C549S065000, C549S378000, C549S424000, C560S009000, C560S020000, C560S023000, C560S036000, C560S037000, C562S455000

Reexamination Certificate

active

06310245

ABSTRACT:

The present invention relates to 2-benzoylcyclohexane-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
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, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
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
, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and for R
9
of the radicals —COR
9
, —CO
2
R
9
, —COSR
9
and —CONR
8
R
9
to be partially or fully halogenated and/or to have attached to them 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, phenyl-C
1
-C
4
-alkyl, hetaryl, phenoxy, phenyl-C
1
-C
4
-alkoxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted;
X is oxygen or sulfur;
Z is oxygen or NR
8
;
m is 0 or 1;
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 an unsubstituted or substituted cyclohexane-1,3-dione ring which is linked in the 2-position;
where m is 1 if R
3
is hydrogen;
and to the agriculturally useful salts thereof.
Moreover, the invention relates to processes and to intermediates 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 of compositions comprising them for controlling harmful plants.
2-Benzoylcyclohexane-1,3-diones have been disclosed in the literature, for example in EP-A 278 742, EP-A 298 680, EP-A 320 864 and WO 96/14285.
However, the herbicidal properties of the prior-art compounds and their tolerance by crop plants are only moderately satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds which have improved properties.
We have found that this object is achieved by the 2-benzoylcyclohexane-1,3-diones of the formula I and their herbicidal activity.
Furthermore, there have been found herbicidal compositions which comprise the compounds I and which have a very good herbicidal activity. Moreover, there have been found processes for the preparation of these compositions and methods of controlling undesired vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can also contain 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 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 unimportant. In general, suitable salts are 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.
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 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 or hydroxy-C
1
-C
4
-alkyl and/or a phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition 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.
Compounds of the formula I according to the invention to be emphasised are those where the variable Q is a cyclohexane-1,3-dione ring of the formula II
where II also represents the tautomeric formulae II′, and II″,
which is linked in the 2-position and where
R
11
, R
12
, R
14
and R
16
are hydrogen or C
1
-C
4
-alkyl;
R
13
is hydrogen, C
1
-C
4
-alkyl or C
3
-C
4
-cycloalkyl, it being possible for the two last-mentioned groups to have attached to them 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, 1,4-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, it being possible for the 6 last-mentioned radicals to 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 carbocycylic ring;
 or
 the CR
13
R
14
unit can be replaced by C═O.
Compounds of the formula I according to the invention equally to be emphasized are those 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
, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and for R
9
of the radicals —COR
9
, —CO
2
R
9
, —COSR
9
and —CONR
8
R
9
to be partially or fully halogenated and/or to have attached to them 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, phenyl-C
1
-C
4
-alkyl, hetaryl, phenoxy, phenyl-C
1
-C
4
-alkoxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be partially or fully halogenated and/or to have attached to them one to three radicals selected from the group which follows:
 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 heterocyclyl rings are collective terms for individual enumerations 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, alkynyl moieties can be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably have attached to them one to five identical or different halogen atoms. Halogen is in each case fluorin

Affiliated with

Also associated with

Rating

3-aminocarbonyl/3-aminothiocarbonyl-substituted... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 3-aminocarbonyl/3-aminothiocarbonyl-substituted..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 3-aminocarbonyl/3-aminothiocarbonyl-substituted... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2581876