Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline...

Details Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline... Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline...

2000-09-13

2002-06-25

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C504S106000, C504S107000, C504S110000, C504S112000, C504S218000, C504S219000, C504S220000, C504S145000

Reexamination Certificate

active

06410480

ABSTRACT:

The present invention relates to novel herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives, to processes for their preparation, to compositions which comprise these compounds and may additionally comprise safeners, and to the use of these compounds as herbicides for controlling weeds and grasses, in particular in crops of useful plants.
3-Hydroxy-4-aryl-5-oxopyrazoline derivates having herbicidal action are described, for example, in EP-A-0 508 126, WO 96/25395 and WO 96/21652. We have now found novel 3-hydroxy-4-aryl-5-oxopyrazoline derivatives having herbicidal properties.
The present invention thus provides compounds of the formula I
in which
R
1
, R
2
and R
3
independently of one another are halogen, nitro, cyano, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
haloalkyl, C
2
-C
6
haloalkenyl, C
3
-C
6
cycloalkyl, halogen-substituted C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxyalkyl, C
1
-C
6
alkylthioalkyl, hydroxyl, mercapto, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, amino, C
1
-C
4
alkylamino or di(C
1
-C
4
-alkyl)amino;
R
4
and R
5
together are a group
—C—R
6
(R
7
)—O—C—R
8
(R
9
)—C—R
10
(R
11
)—C—R
12
(R
13
)—  (Z
1
),
—C—R
14
(R
15
)—C—R
16
(R
17
)—O—C—R
18
(R
19
)—C—R
20
(R
21
)—  (Z
2
),
or
—C—R
22
(R
23
)—C—R
24
(R
25
)—C—R
26
(R
27
)—O—C—R
28
(R
29
)—  (Z
3
);
in which
R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
, R
16
, R
17
, R
18
, R
19
, R
20
, R
21
, R
22
, R
23
, R
24
, R
25
, R
26
, R
27
, R
28
, and R
29
independently of one another are hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl where an alkylene ring, which together with the carbon atoms of the groups Z
1
, Z
2
or Z
3
contains 2 to 6 carbon atoms and may be interrupted by oxygen, may either be fused or spiro-linked to the carbon atoms of the groups Z
1
, Z
2
or Z
3
, or where this alkylene ring bridges at least one ring atom of the groups Z
1
, Z
2
or Z
3
;
G is hydrogen, —C(X
1
)—R
30
, —C(X
2
)—X
3
—R
31
, —C(X
4
)—N(R
32
)—R
33
, —SO
2
—R
34
, an alkali metal, alkaline earth metal, sulfonium or ammonium cation or —P(X
5
)(R
35
)—R
36
;
X
1
, X
2
, X
3
, X
4
and X
5
independently of one another are oxygen or sulfur; and
R
30
, R
31
, R
32
, R
33
, R
34
, R
35
and R
36
independently of one another are hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
2
-C
5
alkenyl, C
1
-C
5
alkoxyalkyl, C
3
-C
6
cycloalkyl or phenyl, and R
34
is additionally C
2
-C
20
alkenyl, C
2
-C
20
alkenyl substituted by halogen, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxy, thioalkyl, alkylthiocarbonyl, alkylcarbonylthio, alkylsulfonyl, alkylsulfoxyl, alkylaminosulfonyl, dialkylaminosultonyl, alkylsultonyloxy, alkylsulfonylamino, alkylamino, dialkylamino, alkylcarbonylamino, dialkylcarbonylamino, alkyl-alkylcarbonylamino, cyano, (C
3
-C
7
)cycloalkyl, (C
3
-C
7
)heterocyclyl, trialkylsilyl, trialkylsilyloxy, phenyl, substituted phenyl, heteroaryl or substituted heteroaryl, C
2
-C
20
alkynyl, C
2
-C
20
alkynyl substituted by halogen, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxy, thioalkyl, alkylthiocarbonyl, alkylcarbonylthio, alkylsulfonyl, alkylsulfoxyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyloxy, alkylsulfonylamino, alkyiamino, dialkylamino, alkylcarbonylamino, dialkylcarbonylamino, alkyl-alkylcarbonylamino, cyano, (C
3
-C
7
)cycloalkyl, (C
3
-C
7
)heterocyclyl, trialkylsilyl, trialkylsilyloxy, phenyl, substituted phenyl, heteroaryl or substituted heteroaryl, (C
1
-C
7
)cycloalkyl, (C
1
-C
7
)cycloalkyl substituted by halogen, haloalkyl, (C
1
-C
6
)alkyl, alkoxy, alkylcarbonyloxy, thioalkyl, alkylcarbonylthio, alkylamino, alkylcarbonylamino, trialkylsilyl or trialkylsilyloxy, heteroaryl, heteroaryl substituted by halogen, haloalkyt, nitro, cyano, (C
1
-C
6
)alkyl, alkoxy, alkylcarbonyloxy, thioalkyl, alkylcarbonylthio, alkylamino, alkylcarbonylamino, trialkylsilyl or trialkylsilyloxy, heteroaryloxy, substituted heteroaryloxy, heteroarylthio, substituted heteroarylthio, heteroarylamino, substituted heteroarylamino, diheteroarylamino, substituted diheteroarylamino, phenylamino, substituted phenylamino, diphenylamino, substituted diphenylamino, cycloalkylamino, substituted cycloalkylamino, dicycloalkylamino, substituted dicycloalkylamino, cycloalkoxy or substituted cycloalkoxy, and salts and diastereomers of the compounds of the formula I.
In the above definitions, halogen is to be understood as meaning fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine. The alkyl groups in the definitions of the substituents are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, and the isomeric pentyls and hexyls. Suitable cycloalkyl substituents contain 3 to 6 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. These may be mono- or polysubstituted by halogen, preferably by fluorine, chlorine or bromine. Alkenyl is to be understood as meaning, for example, vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. Alkynyl is, for example, ethinyl, propargyl, but-2-in-1-yl, 2-methylbutin-2-yl or but-3-in-2-yl. Haloalkyl groups preferably have a chain length of 1 to 4 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl. Suitable haloalkenyls are alkenyl groups which are mono- or polysubstituted by halogen, halogen being fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl. Among the C
2
-C
6
alkenyl groups which are mono-, di- or trisubstituted by halogen, preference is given to those having a chain length of 3 to 5 carbon atoms. Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, and the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Alkylthio groups preferably have a chain length of 1 to 4 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl. Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl. Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Alkoxyalkyl groups preferably have 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioet

Affiliated with

Also associated with

Rating

Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2935515