1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and...

Details 1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and... 1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and...

1998-11-20

2001-05-15

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S365400

Reexamination Certificate

active

06232271

ABSTRACT:

1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides
The invention relates to 1-methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles, to processes for their preparation and to their use as herbicides.
Herbicidally active pyrazolylpyrazoles are known from various publications. Thus, EP-A 0 542 388, WO 94108999 and WO 96109303 describe pyrazolylpyrazoles which carry hydrogen or optionally halogen-substituted alkyl, alkylthio or alkoxy in position 5. The German patent application No. 196 23 892.7, which has earlier priority but is not prior published, mentions pyrazolylpyrazoles which carry a radical from the group consisting of alkyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxy in position 5, where these radicals are in each case unsubstituted or substituted by halogen. WO 97/09313 discloses pyrazolylpyrazoles which are substituted in the 5-position of one of the pyrazole rings by, inter alia, an unsubstituted or substituted radical from the group consisting of alkyl, alkoxy and alkylthio, and in the 4-position of the other pyrazole ring by the thiocarbamoyl group.
Particular properties of, specifically, 1-methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles are not disclosed in these publications. Moreover, the herbicidal activity of the compounds mentioned in these publications is not always sufficient, or, if the herbicidal activity is sufficient, there are selectivity problems in crops of useful plants.
It is an object of the present invention to provide pyrazolylpyrazoles having superior biological properties.
This object is achieved by the 1-methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles of the formula (I)
in which
R
1
is C
1
-C
3
-alkyl, C
3
-C
8
-cycloalkyl or C
2
-C
3
-alkenyl, where these radicals are unsubstituted or substituted by one or more identical or different halogen atoms;
R
2
is halogen or cyano;
R
3
is cyano, nitro or thiocarbamoyl;
R
4
is halogen, C
1
-C
6
-alkyl which is unsubstituted or substituted by one or more identical or different halogen atoms, or is one of the groups
A is cyano or one of the groups
R
5
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, where the four last mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms;
R
6
is C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, where these four radicals are unsubstituted or substituted by one or more identical or different halogen atoms, di-(C
1
-C
4
-alkoxy)-C
1
-C
3
-alkyl or the group
R
7
is hydrogen, C
1
-C
4
alkyl or C
3
-C
8
-cycloalkyl, where the two last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms;
R
8
is C
1
-C
6
-alkyl whose carbon chain may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur and which is unsubstituted or substituted by one or more identical or different halogen atoms;
R
9
is hydrogen, C
1
-C
3
-alkyl, halogen, amino, C
1
-C
4
-alkylamino or di-(C
1
-C
4
-alkyl)amino;
R
10
is hydrogen, C
1
-C
3
-alkyl, halogen, amino, hydroxyl, C
1
-C
4
-alkylamino or di-(C
1
-C
4
-alkyl)amino;
R
11
is hydrogen, C
1
-C
3
-alkyl or the group XR
12
;
R
12
is C
1
-C
6
-alkyl whose carbon chain may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur and which is unsubstituted or substituted by one or more identical or different halogen atoms;
R
13
is C
1
-C
6
-alkyl whose carbon chain may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur and which is unsubstituted or substituted by one or more identical or different halogen atoms;
R
14
is C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, where these four radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxycarbonyl, cyano or halogen, and where the carbon chain of these four abovementioned radicals may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur;
R
15
is C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, where these four radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of C
1
-C
4
-alkoxycarbonyl or halogen, and where the carbon chain of these four abovementioned radicals may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or
R
14
and R
15
together with the linking nitrogen atom form a 3-, 5- or 6-membered saturated, partially saturated or maximally unsaturated ring which is unsubstituted or substituted by one or more methyl groups and where one carbon atom may be replaced by an oxygen atom;
R
16
, R
17
, R
18
, R
19
, R
20
and R
21
independently of one another are hydrogen, C
1
-C
4
-alkyl which is unsubstituted or substituted by one or more identical or different halogen atoms, or two of these radicals together form a bond;
X is oxygen or sulfur;
m is 0, 1 or 2;
n is 0, 1 or 2;
p is 0, 1 or 2 and
q is 1 or 2.
The term “halogen” includes fluorine, chlorine, bromine and iodine. Unless stated otherwise, preference is given to chlorine and fluorine.
The term “C
1
-C
3
-alkyl” is to be understood as the methyl, ethyl, propyl and isopropyl radical. “C
1
-C
6
-Alkyl” is to be understood as an unbranched or branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms, such as, for example, in addition to the abovementioned radicals the 1-butyl, 2-butyl, 2-methylpropyl, tert-butyl, pentyl, 2-methylbutyl, 1,1-dimethylpropyl and hexyl radical. Alkyl radicals having a different range of numbers of carbon atoms are to be understood analogously.
The term “C
3
-C
8
-cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
The terms “C
2
-C
6
-alkenyl” and “C
2
-C
6
-alkynyl” denote a straight-chain or, if possible, a branched hydrocarbon radical having 2, 3, 4, 5 or 6 carbon atoms, where this hydrocarbon radical includes at least one multiple bond, and this multiple bond can be located in any position of the unsaturated radical in question; preferably, it is not located at the carbon atom which is linked with the remaining molecular moiety of the compound of the formula (I). “C
2
-C
6
-Alkenyl” thus denotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl and the hexenyl group. “C
2
-C
6
-Alkynyl” denotes, for example, the ethynyl, propargyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl and the 2-hexynyl group. Alkenyl radicals and alkynyl radicals having a different range of numbers of carbon atoms are to be understood analogously.
If the carbon chain of an alkyl, alkenyl or alkynyl radical is interrupted by more than one heteroatom, these heteroatoms should not be directly adjacent to each other.
“C
1
-C
4
-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has, analogously, the meaning given under the definitions of alkyl. Alkyl radicals in other compound terms such as “C
1
-C
4
-alkylamino” are to be understood likewise. In the case of di-(C
1
-C
4
-alkyl)amino, the two alkyl radicals can be identical or different.
If a radical is multiply substituted, this is to be understood in such a way that at least two and at most all hydrogen atoms of this radical are substituted by identical or different other radicals. The possibilities of combining the various substituents of the formula (I) are to be understood in such a way that the general principles of the synthesis of chemical compounds are to be observed, i.e. that no compound

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