Herbicidal halogenalkyl-substituted...

Details Herbicidal halogenalkyl-substituted... Herbicidal halogenalkyl-substituted...

2002-05-16

2003-07-29

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S240000

Reexamination Certificate

active

06599860

ABSTRACT:

The present invention relates to haloalkyl-substituted 3-(4,5-dihydroisoxazol-3-yl)benzoylcyclohexenones and to processes for their preparation, to compositions comprising them and to the use of these derivatives or compositions for controlling harmful plants.
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.
We have found that this object is achieved by the haloalkyl-substituted 3-(4,5-dihydroisoxazol-3-yl)benzoylcyclohexenones of the formula I
in which
R
1
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
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, halogen, cyano or nitro;
R
3
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
4
is C
1
-C
4
-haloalkyl;
R
5
, R
6
, R
7
independently of one another are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
8
is hydroxyl, mercapto, halogen, OR
15
, SR
15
, SOR
16
or SO
2
R
16
;
R
9
, R
13
independently of one another are hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio or C
1
-C
4
-alkoxycarbonyl;
R
10
, R
12
, R
14
independently of one another are hydrogen or C
1
-C
4
-alkyl;
R
11
is hydrogen, hydroxyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, di(Ci-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 lastmentioned radicals may carry one, two or three substituents selected from C
1
-C
4
-alkyl; or
R
9
and R
10
or R
13
and R
14
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
10
and R
11
or R
13
and R
14
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
10
and R
14
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
11
and R
12
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
11
and R
12
together are an oxygen atom;
R
15
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 and 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
16
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 and C
3
-C
6
-cycloalkyl; is 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, 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;
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.
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 enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures. The compounds of the formula I where R
8
=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 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.
The organic moieties mentioned for the substituents R
1
-R
16
or as radicals on phenyl

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