Herbicide agent

Details Herbicide agent Herbicide agent

2002-02-26

2003-04-29

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S136000

Reexamination Certificate

active

06555499

ABSTRACT:

This appl'n is a 371 of PCT/EP00/08659 filed Sep. 5, 2000.
A The present invention relates to new selectively herbicidal compositions for controlling grasses and weeds in crops of useful plants, especially in crops of maize and cereals, which compositions comprise a 3-hydroxy-4-(4-methylphenyl)-5-oxo-pyrazoline herbicide, a safener (counter-agent, antidote) and an oil additive and protect the useful plants but not the weeds against the phytotoxic action of the herbicide, and to the use of such compositions in controlling weeds in crops of useful plants.
When using herbicides, the cultivated plants may also suffer considerable damage, depending on, for example, the amount of herbicide used and the method of application, the cultivated plant, the nature of the soil and climatic conditions, for example hours of daylight, temperature and amounts of rainfall. In order to deal with that and similar problems, various substances have already been proposed as safeners, which are capable of antagonising the harmful effect of the herbicide on the cultivated plant, that is to say are capable of protecting the cultivated plant, without appreciably impairing the herbicidal action on the weeds to be acontrolled.
It has been found that the proposed safeners often act very specifically both with respect to the cultivated plants and with respect to the herbicide, and in some cases also in dependence on the method of application, that is to say, a particular safener is often suitable only for a particular cultivated plant and a specific class of herbicidal substance or a particular herbicide. For example, it has been found that although the safeners cloquintocet and cloquintocet-mexyl and mefenpyr and mefenpyr-diethyl, known from EP-A-0 191 736 (compound 1.316) and WO 91/07874 (Example 3) and from The Pesticide Manual, 11th Ed., British Crop Protection Council, Entry No. 154 and 462, are capable of protecting the cultivated plant from the phytotoxic action of particular 3-hydroxy-4-(4-methylphenyl)-5-oxo-pyrazoline derivatives, they do, however, reduce the herbicidal action on weeds in some cases.
U.S. Pat. No. 4,834,908 discloses that certain oil additive combinations can increase the herbicidal activity of compounds from the class of the cyclohexanediones, benzothiadiazinone dioxides, diphenyl ether herbicides and aryloxyphenoxy herbicides.
Although the 3-hydroxy-4-(4-methylphenyl)-5-oxo-pyrazoline derivatives are structurally completely different from the compounds disclosed in U.S. Pat. No. 4,834,908, the combination of such oil additives with the said 3-hydroxy-4-(4-methylphenyl)-5-oxo-pyrazoline derivatives likewise results in an increase in herbicidal activity but the cultivated plant is also damaged to a considerable extent. That herbicide/oil additive mixture is therefore not suitable for selectively controlling weeds in crops of useful plants.
It has now been found, surprisingly, that weeds can be selectively controlled very successfully using the particular 3-hydroxy-4-(4-methylphenyl)-5-oxo-pyrazoline herbicides without damaging the cultivated plant, by applying those compounds in combination with an additive comprising an oil of vegetable or animal origin or a mineral oil, alkyl esters thereof, or mixtures of those oils and oil derivatives, and with the safeners cloquintocet or mefenpyr.
The present invention accordingly relates to a selectively herbicidal composition that, in addition to comprising customary inert formulation adjuvants such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of
a) a herbicidally effective amount of a compound of formula I
 wherein
R
1
and R
3
are, each independently of the other, 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, halo-substituted C
3
-C
6
cycloalkyl, C
2
-C
6
alkoxyalkyl, C
2
-C
6
alkylthioalkyl, hydroxy, mercapto, C
1
-C
6
alkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, carbonyl, carboxyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
hydroxyalkyl, 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
),
wherein 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
are, each independently of the others, hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, it being possible for an alkylene ring, which together with the carbon atoms of the groups Z
1
, Z
2
or Z
3
contains from 2 to 6 carbon atoms and which may be interrupted by oxygen, to be either fused or spiro-bound to the carbon atoms of the groups
Z
1
, Z
2
or Z
3
or that 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
or —CH
2
—X
6
—R
37
;
X
1
, X
2
, X
3
, X
4
, X
5
and X
6
are, each independently of the others, oxygen or sulfur;
R
30
, R
31
, R
32
and R
33
are, each independently of the others, hydrogen, C
1
-C
10
alkyl, C
1
-C
10
-haloalkyl, C
1
-C
10
cyanoalkyl, C
1
-C
10
nitroalkyl, C
1
-C
10
aminoalkyl, C
1
-C
5
alkylamino-C
1
-C
5
alkyl, C
2
-C
8
dialkylamino-C
1
-C
5
alkyl, C
3
-C
7
cycloalkyl-C
1
-C
5
alkyl, C
2
-C
10
alkoxy-alkyl, C
4
-C
10
-alkenyloxy-alkyl, C
4
-C
10
alkynyloxy-alkyl, C
2
-C
10
alkylthio-alkyl, C
1
-C
5
alkysulfoxyl-C
1
-C
5
alkyl, C
1
-C
5
alkylsulfonyl-C
1
-C
5
alkyl, C
2
-C
8
alkylideneamino-oxy-C
1
-C
5
alkyl, C
1
-C
5
alkylcarbonyl-C
1
-C
5
alkyl, C
1
-C
5
alkoxycarbonyl-C
1
-C
5
alkyl, C
1
-C
5
amino-carbonyl-C
1
-C
5
alkyl, C
2
-C
8
dialkyl-amino-carbonyl-C
1
-C
5
alkyl, C
1
-C
5
alkylcarbonylamino-C
1
-C
5
alkyl, C
2
-C
5
alkylcarbonyl-(C
1
-C
5
alkyl)-aminoalkyl, C
3
-C
6
trialkylsilyl-C
1
-C
5
alkyl, phenyl-C
1
-C
5
alkyl, heteroaryl-C
1
-C
5
alkyl, phenoxy-C
1
-C
5
alkyl, heteroaryloxy-C
1
-C
5
alkyl, C
2
-C
5
alkenyl, C
2
-C
5
haloalkenyl, C
3
-C
8
cycloalkyl, phenyl, or C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted phenyl or heteroaryl or heteroarylamino, C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted heteroarylamino, diheteroarylamino, C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted diheteroarylamino, phenylamino, C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted phenylamino, diphenylamino, C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted diphenylamino, C
3
-C
7
cycloalkylamino, C
1
-C
3
alkyl-, C
1
-C
3
-haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted C
3
-C
7
cycloalkylamino, di-C
3
-C
7
cycloalkylamino, C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted di-C
3
-C
7
cycloalkylamino, C
3
-C
7
cycloalkoxy or C
1
-C
3
alkyl-, C
1
-C
3
haloalkyl-, C
1
-C
3
alkoxy-, C
1
-C
3
haloalkoxy-, halo-, cyano- or nitro-substituted C
3
-C
7
cycloalkoxy;
R
34
, R
35
and R
36
are hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
1
-C
10
cyanoalkyl, C
1
-C
10
-nitroalkyl, C
1
-C
10
aminoalkyl, C
1
-C
5
alkylamino-C
1
-C
5
alkyl, C
2
-C
8
dialkylamino-C
1
-C
5
alkyl, C
3
-C
7
cycloalkyl-C
1
-C
5
alkyl, C
2
-C
10
alkoxy-alkyl, C
4
-C
10
alkenyloxy-alkyl, C
4
-C
10
alkynyloxy-alkyl, C
2
-C
10
alkylthio-alkyl, C
1
-C
5
alkysulfoxyl-C
1
-C
5
alkyl, C
1
-C
5
alkylsulfonyl-C
1
-C
5
alkyl, C
2
-C
8
alkylideneamino-oxy-C
1
-C
5
alkyl, C
1
-C
5
alkylcar

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