Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-07-25
2001-04-03
Stockton, Laura L. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S236800, C514S269000, C514S326000, C514S340000, C544S137000, C544S298000, C544S319000, C546S209000, C546S272100, C548S240000, C548S247000
Reexamination Certificate
active
06211216
ABSTRACT:
DESCRIPTION
Isoxazolyl- and isoxazolinyl-substituted benzoylcyclohexanediones, process for their preparation and their use as herbicides and plant growth regulators.
The invention relates to the technical field of the herbicides and plant growth regulators, in particular that of the herbicides for the selective control of weeds and weed grasses in useful plant crops.
It is already disclosed in various patents that certain benzoylcyclohexanediones, also those which are substituted for example, by a heterocyclic radical in the 3-position of the phenyl ring, have herbicidal properties. Thus in WO 98142648 benzoylcyclohexandiones are described which carry a heterocycle linked via a nitrogen atom in the position mentioned. A preferred heterocycle mentioned there is morpholine. WO 96/26200 discloses benzoylcyclohexanediones which carry various 5- or 6-membered heterocycles in the position mentioned. WO 97/46530 mentions pyridylcarbonylcyclohexanediones and benzoylcyclohexanediones which carry a heterocyclic radical in addition to others. In this case, the restriction is made for the benzoylcyclohexanediones described there that the phenyl ring must still carry three further substitutents if the heterocyclic radical is in the 3-position.
The use of the benzoylcyclohexanediones known from these patents is, however, frequently associated with disadvantages in practice. Thus the herbicidal or plant growth-regulating activity of the known compounds is not always adequate, or if the herbicidal activity is adequate undesired damage to the useful plants is observed.
The object of the present invention is the provision of compounds which have a herbicidal and plant growth-regulating action and which overcome the disadvantages known from the prior art.
The object is achieved by benzoylcyclohexanediones carrying a substituted isoxazoline radical in the 3-position of the phenyl ring, of the formula (I)
in which
A is a saturated or mono- or polyunsaturated hydrocarbon chain comprising one to eight carbon atoms as chain members, which is optionally substituted by one or more radicals from the group consisting of halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy and hydroxyl and which is optionally interrupted by one or two divalent units from the group consisting of oxygen, sulfur and carbonyl;
R
1
, is OR
11
, SR
11
, SOR
11
, SO
2
R
11
, CO
2
R
8
, CONR
8
R
9
,N(R
8
)COR
9
, N(R
8
)SO
2
R
9
, N(R
8
)—CO—X, P(O)R
8
R
9
, cyano, nitro, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, phenyl, phenoxy, phenylthio, heteroaryl, heteroaryloxy, heterocyclyl or heterocyclyloxy, where the nine last-mentioned radicals are optionally mono- or polysubstituted, or
A and R
1
together form a radical of the group consisting of heteroaryl and heterocyclyl, where these two mentioned radicals are optionally mono- or polysubstituted;
R
a
, R
b
, R
c
independently of one another are hydrogen, optionally mono- or polysubstituted C
1
-C
9
-alkyl, OR
11
, SR
11
, SOR
11
, SO
2
R
11
, CONH
2
, CONR
8
R
9
, cyano, nitro, halogen or the group A—R
1
, or
R
a
and R
c
together form a bond;
R
2
, R
3
, R
4
, and R
5
independently of one another are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, heteroaryloxy, heterocyclyloxy, alkylthio, arylthio, heteroarylthio, heterocyclylthio, heterocyclylalkylthio, amino, mono- or dialkylamino, mono- or diarylamino, N-alkyl-N-arylamino, cycloalkylamino, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, aminosulfonyl, mono- or dialkylaminosulfonyl, mono- or diarylaminosulfonyl, N-alkyl-N-arylaminosulfonyl, N-alkyl-N-heteroarylaminosulfonyl, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, heteroarylsulfonylamino, cycloalkylsulfonyl-N-alkylamino, arylsulfonyl-N-alkylamino, heteroarylsulfonyl-N-alkyiamino, heterocyclylsulfonyl-N-alkylamino, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carboxyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, arylalkylcarbonyloxy, aminocarbonyl, mono- or dialkylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, N-alkyl-N-heteroarylaminocarbonyl, N-alkyl-N-arylaminocarbonyloxy, aminocarbonylamino, mono- or dialkylaminocarbonylamino, mono- or diarylaminocarbonylamino, mono- or diheteroarylaminocarbonylamino, N-alkyl-N-arylaminocarbonylamino, mono- or dialkylcarbonylamino, mono- or diarylcarbonylamino, alkylcarbonyl-N-arylamino, arylcarbonyl-N-alkylamino, alkoxycarbonyloxy, cycloalkoxycarbonyloxy, aryloxycarbonyloxy, arylalkoxycarbonyloxy, alkoxycarbonylamino, cycloalkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl-N-alkylamino, formyl, halogen, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio, haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino, haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl, haloalkynylsulfonyl, haloalkylsulfinyl, haloalkenylsulfinyl, haloalkynylsulfinyl, haloalkylcarbonyl, haloalkenylcarbonyl, haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl, haloalkynyloxycarbonyl, haloalkylaminocarbonyl, haloalkenylaminocarbonyl, haloalkynylaminocarbonyl, haloalkoxycarbonylamino, haloalkylaminocarbonylamino, cyano, nitro, arylalkoxyalkoxy or alkoxyalkoxyall(oxy;
R
6
is OR
10
, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkenylsulfinyl, haloalkenylsulfinyl, alkynylsulfinyl, haloalkynylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenylsulfonyl, haloalkenylsulfonyl, alkynylsulfonyl, haloalkynylsulfonyl, optionally substituted phenylthio, cyano, cyanato, thiocyanato or halogen;
R
7
is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, phenyl, where the eight last-mentioned groups are optionally substituted by one or more, identical or different radicals from the group consisting of halogen, alkylthio and alkyloxy, or
two radicals R
7
bonded to a common carbon atom form a chain from the group consisting of OCH
2
CH
2
O, OCH
2
CH
2
CH
2
O, SCH
2
CH
2
S and SCH
2
CH
2
CH
2
S, this optionally being substituted by one to four methyl groups, or
two radicals R
7
bonded to directly adjacent carbon atoms form a bond or, with the carbon atoms carrying them, form a 3- to 6-membered ring optionally substituted by one or more, identical or different radicals from the group consisting of halogen, alkyl, alkylthio and alkoxy;
R
8
and R
9
independently of one another are hydrogen, alkyl, alkyloxy, alkoxy, alkenyl, alkenyloxy, alkynyl, haloalkyl, cycloalkyl, cyanoalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl or optionally substituted arylalkyl, or
R
8
and R
9
, together with the atom bonding them, form a 5- or 6-membered saturated, partially or completely unsaturated ring, which optionally contains one or two further heteratoms from the group consisting of oxygen and nitrogen and which is optionally substituted by one to three radicals from the group consisting of halogen, alkyl and oxo;
R
10
is hydrogen, alkyl, haloalkyl, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, benzoyl or phenylsulfonyl, the two last-mentioned groups optionally being substituted by one or more, identical or different radicals from the group consisting of alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano and nitro;
R
11
R
10
, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or cycloalkylalkyl;
X is a radical from the group consisting of heteroaryl and heterocyclyl;
Y is a divalent unit from the group consisting of O, S, N—H, N-alkyl, CHR
7
and C(R
7
)
2
;
Z is a divalent unit from the group consisting of O, S, SO, SO
2
, N—H, N-alkyl, CHR
7
and C(R
7
)
2
;
v is 0or 1;
w is 0,1,2,3 or 4,
with the proviso that at least two radicals from R
2
, R
3
, R
4
and R
5
are hydrogen.
N
Auler Thomas
Bieringer Hermann
Thürwächter Felix
Van Almsick Andreas
Willms Lothar
Aventis CorpScience GmbH
Frommer & Lawrence & Haug LLP
Stockton Laura L.
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