3-(4,5-Dihydroisoxazol-5-yl)benzoylcyclohexenones and the...

Details 3-(4,5-Dihydroisoxazol-5-yl)benzoylcyclohexenones and the... 3-(4,5-Dihydroisoxazol-5-yl)benzoylcyclohexenones and the...

2002-11-14

2003-11-11

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S240000

Reexamination Certificate

active

06645919

ABSTRACT:

The present invention relates to 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula I
in which the variables have the following meanings:
R
1
, R
2
are hydrogen, nitro, halogen, cyano, 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 or C
1
-C
6
-haloalkylsulfonyl;
R
3
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
4
is hydrogen or C
1
-C
4
-alkyl;
R
5
, R
6
are hydrogen, halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkoxy)-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)amino-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)aminoimino-C
1
-C
4
-alkyl, hydroxyimino-C
1
-C
4
-alkyl, C
1
-C
6
-alkoxyimino-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-cyanoalkyl, C
3
-C
8
-cycloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxy-C
2
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, di(C
1
-C
4
-alkyl)amino, COR
8
, phenyl or benzyl, it being possible for the two last-mentioned substituents to be partially or fully halogenated and/or to have attached to them one to three of the following groups: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy; or
R
5
and R
6
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 by unsubstituted or C
1
-C
4
-alkyl-substituted nitrogen;
R
7
is halogen, cyano, hydroxyl, 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, amino, C
1
-C
6
-alkylamino, di(C
1
-C
6
-alkyl)amino, di(C
1
-C
4
-alkoxy)methyl, hydroxylamino-C
1
-C
4
-alkyl, C
1
-C
6
-alkoxyimino-C
1
-C
4
-alkyl or COR
8
;
R
8
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, hydroxyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxy-C
2
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy or NR
9
R
10
;
R
9
is hydrogen or C
1
-C
4
-alkyl;
R
10
is C
1
-C
4
-alkyl;
R
11
is a cyclohexenone of the formula II
 which is linked in the 2-position and where
R
12
is hydroxyl, mercapto, halogen, OR
19
, SR
19
, SOR
20
or SO
2
R
20
;
R
13
, R
17
are hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio or C
1
-C
4
-alkoxycarbonyl;
R
14
, R
16
, R
18
are hydrogen or C
1
-C
4
-alkyl;
R
15
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, it being possible for the six last-mentioned radicals to have attached to them one, two or three substituents selected from amongst C
1
-C
4
-alkyl; or
R
13
and R
14
or R
17
and R
18
together are C
1
-C
5
-alkanediyl which can have attached to it one, two or three substituents selected from amongst halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl;
R
14
and R
15
or R
15
and R
18
together are a chemical bond or C
1
-C
5
-alkanediyl which can have attached to it one, two or three substituents selected from amongst halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
14
and R
18
together are C
1
-C
5
-alkanediyl which can have attached to it one, two or three substituents selected from amongst halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
15
and R
16
together are —O—(CH
2
)
p
—O—, —O—(CH
2
)
p
—S—, —S—(CH
2
)
p
—S—, —O—(CH
2
)
q
— or —S—(CH2)
q
—, each of which can have attached to it one, two or three substituents selected from amongst halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
15
and R
16
together are an oxygen atom;
R
19
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, it being possible for the abovementioned alkyl, alkoxy and cycloalkyl radicals to be partially or fully halogenated and/or to have attached to them one, two or three substituents selected from amongst 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; 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, it being possible for the phenyl or heterocyclyl radical of the abovementioned radicals to be partially or fully halogenated and/or to have attached to it one, two or three substituents selected from amongst nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
20
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, it being possible for the abovementioned alkyl and cycloalkyl radicals to be partially or fully halogenated and/or to have attached to them one, two or three substituents selected from amongst 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; phenyl, phenyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, heterocyclyl, heterocyclyl-C
1
-C
6
-alkyl or heterocyclylcarbonyl-C
1
-C
6
-alkyl, it being possible for the phenyl or heterocyclyl radical of the abovementioned radicals to be partially or fully halogenated and/or to have attached to it one, two or three substituents selected from amongst nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
p is 2, 3 or 4;
q is 1, 2, 3, 4 or 5;
and to their agriculturally useful salts.
The invention furthermore relates to processes for the preparation of compounds of the formula I, to compositions comprising them, and to the use of these derivatives or compositions comprising them for controlling harmful plants.
Benzoylcyclohexenones are disclosed in the literature, for example in WO 96/26200.
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 find novel, in particular herbicidally active, compounds with improved properties.
We have found that this object is achieved by the 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula I and their herbicidal action.
Furthermore, there have been found herbicidal compositions which comprise the compounds I and which have very good herbicidal action. 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

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