Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-05-13
2003-12-23
Solola, Taofiq (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C504S271000, C548S241000
Reexamination Certificate
active
06667333
ABSTRACT:
FIELD OF INVENTION
The present invention relates to certain 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylcyclohexenone derivatives and to processes for their preparation, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.
BACKGROUND INFORMATION
WO 96/26200 discloses herbicidal 2-benzoylcyclohexane-1,3-diones.
However, the herbicidal properties of the 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.
BRIEF SUMMARY
We have found that this object is achieved by the 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylcyclohexenone derivatives of the formula I
in which
A is C
1
-C
4
-alkanediyl which may carry one, two or three substituents selected from the group consisting of halogen and C
1
-C
4
-alkyl;
R
1
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, halogen or nitro;
R
2
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, cyano, halogen or nitro;
R
3
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
4
, R
5
independently of one another are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl; or
R
4
, R
5
together are C
1
-C
4
-alkanediyl which may carry one, two or three substituents selected from the group consisting of halogen and C
1
-C
4
-alkyl;
R
6
is hydroxyl, mercapto, halogen, OR
13
, SOR
14
, SR
13
or SO
2
R
14
;
R
7
, R
11
independently of one another are hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio or C
1
-C
4
-alkoxycarbonyl;
R
8
, R
10
, R
12
independently of one another are hydrogen or C
1
-C
4
-alkyl;
R
9
is hydrogen, hydroxyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, di(C
1
-C
6
-alkoxy)methyl, (C
1
-C
6
-alkoxy) (C
1
-C
6
-alkylthio)methyl, di(C
1
-C
6
-alkylthio)methyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-haloalkoxycarbonyl, 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 six last mentioned radicals may carry one, two or three substituents selected from C
1
-C
4
-alkyl; or
R
7
and R
8
or R
11
and R
12
together are C
1
-C
5
-alkanediyl which may carry one, two or three substituents selected from the group consisting of halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl and C
1
-C
4
-alkoxycarbonyl; or
R
8
and R
9
or R
9
and R
12
together are a chemical bond or C
1
-C
5
-alkanediyl which may carry one, two or three substituents selected from the group consisting of halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl and C
1
-C
4
-alkoxycarbonyl; or
R
8
and R
12
together are C
1
-C
4
-alkanediyl which may carry one, two or three substituents selected from the group consisting of halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxycarbonyl; or
R
9
and R
10
together are —O—(CH
2
)
p
—O—, —O—(CH
2
)
p
—S—, —S—(CH
2
)
p
—S—, —O—(CH
2
)
q
— or —S—(CH
2
)
q
— which may carry one, two or three substituents selected from the group consisting of halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl and C
1
-C
4
-alkoxycarbonyl; or
R
9
and R
10
together are an oxygen atom;
R
13
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
20
-alkylcarbonyl, C
2
-C
20
-alkenylcarbonyl, C
2
-C
6
-alkynylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-alkenyloxycarbonyl, C
3
-C
6
-alkynyloxycarbonyl, C
1
-C
6
-alkylthiocarbonyl, C
1
-C
6
-alkylaminocarbonyl, C
3
-C
6
-alkenylaminocarbonyl, C
3
-C
6
-alkynylaminocarbonyl, N,N-di(C
1
-C
6
-alkyl)aminocarbonyl, N-(C
3
-C
6
-alkenyl)-N-(C
1
-C
6
-alkyl)aminocarbonyl, N-(C
3
-C
6
-alkynyl)-N-(C
1
-C
6
-alkyl)aminocarbonyl, N-(C
1
-C
6
-alkoxy)-N-(C
1
-C
6
-alkyl)aminocarbonyl, N,N-di(C
1
-C
6
-alkyl)aminothiocarbonyl, C
1
-C
6
-alkoxyimino-C
1
-C
6
-alkyl, where the alkyl, alkoxy and cycloalkyl radicals mentioned may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, N,N-di-(C
1
-C
4
-alkyl)aminocarbonyl or C
3
-C
6
-cycloalkyl;
is phenyl, phenyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, heterocyclyl, heterocyclyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, where the phenyl or heterocyclyl radical of the radicals mentioned may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy;
R
14
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl or C
3
-C
6
-cycloalkyl, where the alkyl and cycloalkyl radicals mentioned may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, N,N-di(C
1
-C
4
-alkyl)aminocarbonyl or C
3
-C
6
-cycloalkyl;
is phenyl, phenyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, heterocycyl, heterocyclyl-C
1
-C
6
-alkyl or heterocyclylcarbonyl-C
1
-C
6
-alkyl, where the phenyl or heterocyclyl radical of the radicals mentioned may be partially or fully halogenated and/or may carry one, two or three substituents selected the group consisting of nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy;
p is 2, 3 or 4;
q is 1, 2, 3, 4 or 5;
and their agriculturally useful salts.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
DETAILED DESCRIPTION OF THE INVENTION
Depending on the substitution pattern, the compounds of the formula I may contain one or more centers of chirality, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures. The compounds of the formula I where R
6
═OH or SH can also be present as tautomers of the structure shown, or as tautomer mixtures.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the nature of the salt generally being immaterial. In general, the salts of those cations and the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and also ammonium where, if desired, one to four hydrogens may 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 addi
Baumann Ernst
Deyn Wolfgang von
Kudis Steffen
Langemann Klaus
Mayer Guido
BASF - Aktiengesellschaft
Keil & Weinkauf
Solola Taofiq
LandOfFree
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