Plant protecting and regulating compositions – Antidotes – Hetero ring containing antidote
Reexamination Certificate
2002-06-04
2003-12-09
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Antidotes
Hetero ring containing antidote
C504S271000
Reexamination Certificate
active
06660691
ABSTRACT:
The invention is in the technical field of the crop protection products, in particular herbicide/antidote combinations (active ingredient/safener combinations) which are suitable for use against competing harmful plants in crops of useful plants.
A large number of herbicidal active ingredients are known as inhibitors of the enzyme p-hydroxyphenylpyruvate dioxygenase (HPPD). Only recently, more such active ingredients were disclosed for example in WO 99/58509.
As is the case with many other herbicidal active ingredients, these HPPD inhibitors too are not always sufficiently well tolerated by (i.e. not sufficiently selective in) some important crop plants such as maize, rice or cereals, so that their use is very limited. They can therefore not be employed in some crops, or only at such low application rates that the desired broad herbicidal activity against harmful plants is not ensured. Specifically, many of the abovementioned herbicides cannot be employed as fully selective herbicides against harmful plants in maize, rice, cereals, sugar cane and some other crops.
To overcome these disadvantages, it is known to employ herbicidal active ingredients in combination with what is known as a safener or antidote. Thus, for example, WO 99/66795 describes various combinations of a large number of HPPD inhibitors with a multiplicity of safeners.
A safener is understood as meaning a compound which compensates for, or reduces, the phytotoxic properties of a herbicide with regard to useful plants, without substantially reducing the herbicidal activity against harmful plants.
Finding a safener for a specific groups of herbicides remains a difficult task since the mechanisms by which a safener reduces the harmful action of herbicides are not known in detail. The fact that a compound in combination with a specific herbicide acts as safener allows therefore no conclusions as to whether such a compound also has a safener action with other groups of herbicides. Thus, it has emerged when safeners were used for protecting the useful plants from herbicide damage that the safeners may still exhibit certain disadvantages in many cases. These include:
the safener reduces the activity of the herbicide against the harmful plants,
the useful-plant protecting properties are insufficient,
the spectrum of the useful plants in which the safener/herbicide is to be employed is not sufficiently wide in combination with a given herbicide,
a given safener cannot be combined with a sufficiently large number of herbicides.
It was an object of the present invention to provide further combinations of herbicides from the group of the HPPD inhibitors with safeners which are suitable for increasing the selectivity of these herbicides with regard to important crop plants.
There have now been found novel combinations of specific herbicides from the group of the HPPD inhibitors, specifically from the group of the benzoylpyrazoles, which have selected substituents attached in the 3-position of the benzoyl moiety, with some selected safeners which increase the selectivity of these herbicides with regard to important crop plants.
The invention therefore relates to a herbicidally active composition comprising
A) a herbicidally active amount of one or more compounds of the formula (I),
in which the symbols and indices have the following meanings:
R
1
is (C
1
-C
6
)-alkyl;
R
2
is hydrogen or (C
1
-C
6
)-alkyl;
R
3
is hydrogen, halogen, (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
)-alkylsulfinyl or (C
1
-C
6
)-alkylsulfonyl;
R
4
, R
5
, R
6
are hydrogen or (C
1
-C
6
)-alkyl;
R
7
is (C
1
-C
6
)-alkyl;
a is 0, 1 or 2; and
B) an antidote-effective amount of one or more compounds of the formula (II) or
in which the symbols have the following meanings:
R
8
, R
9
, R
10
independently of one another are hydrogen or (C
1
-C
4
)-alkyl, including the stereoisomers and the salts conventionally used in agriculture.
Herbicidally active amount for the purposes of the invention refers to an amount of one or more herbicides suitable for having an adverse effect on plant growth.
Antidote-effective amount for the purposes of the invention refers to an amount of one or more safeners suitable for at least partially counteracting the phytotoxic effect of the herbicide or herbicide mixture on a useful plant.
Unless specifically otherwise defined, the definitions given hereinbelow generally apply to the radicals in the formulae of (I) to (III) and the subsequent formulae.
The radicals alkyl, alkoxy, haloalkyl, haloalkoxy and alkylthio and the corresponding unsaturated and/or substituted radicals in the carbon skeleton can be in each case straight-chain or branched. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, preferably have 1 to 4 carbon atoms and are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl. “(C
1
-C
4
)-alkyl” is the abbreviation for alkyl having 1 to 4 carbon atoms; the same applies analogously to other general definitions of radicals with bracketed ranges of the possible number of carbon atoms.
Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl is alkyl, alkenyl or alkynyl which is partially or fully substituted by halogen, preferably by fluorine, chlorine, and/or bromine, in particular by fluorine or chlorine, for example CF
3
, CHF
2
, CH
2
F, CF
2
CF
3
, CH
2
FCClFH, CCl
3
, CHCl
2
, CH
2
CH
2
Cl. Haloalkoxy is, for example, OCF
3
, OCHF
2
, OCH
2
F, OCF
2
CF
3
, OCH
2
CF
3
and OCH
2
CH
2
Cl. The same applies analogously to other halogen-substituted radicals.
Formulae (I) to (III) also encompass all stereoisomers which have the same topological linkage of the atoms, and their mixtures. Such compounds contain one or more asymmetric carbon atoms or else double bonds which are not specified individually in the general formula. The possible stereoisomers which are defined by their specific spatial shape such as enantiomers, diasteriomers, Z- and E-isomers can be obtained from stereoisomer mixtures by customary methods or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
Suitable herbicidal active ingredients are in accordance with the invention those compounds of the formula (I) which cannot be employed on their own, or which can not be employed optimally on their own, in crops of useful plants such as cereal crops, rice or maize since they cause too much damage to the crop plants.
Herbicides of the formula (I) are disclosed for example in WO 99/65314 and WO 99/58509.
The publications cited contain detailed information on preparation processes and starting materials. These publications are expressly referred to, they are incorporated into the present application by reference.
The compounds of the formula (II) are known for example from WO 91/07874 and the literature cited therein and can be prepared by, or analogously to, the methods described therein. The compounds of the formula (III) are known from WO 95/07897 and literature cited therein and can be prepared by, or analogously to, the methods described therein.
The publications cited contain detailed information on preparation processes and starting materials. These publications are expressly referred to, they are incorporated into the present application by reference.
For the purposes of the present application, the term “herbicidal compositions” and “herbicide/safener combinations” are to be considered as equal.
Preferred herbicidal compositions are those which comprise compounds of the formula (I), in which the symbols and indices have the following meanings:
R
1
is (C
1
-C
6
)-alkyl;
R
2
is hydrogen or (C
1
-C
6
)-alkyl;
R
3
is halogen or (C
1
-C
6
)-alkyl;
R
4
, R
5
, R
6
are hydrogen, (C
1
-C
6
)-alkyl;
R
7
is (C
1
-C
6
)-alkyl;
a is 0, 1 or 2.
Also preferred are herbicidal compositions comprising safeners of the formula (II) and/or (III), in which R
8
, R
9
and R
10
independently of one another are hydrogen or (C
1
-C
2
)-alkyl.
Especially preferred are h
Almsick Andreas van
Bieringer Hermann
Hacker Erwin
Köhn Arnim
Willms Lothar
Aventis CropScience GmbH
Clardy S. Mark
Frommer Lawernce & Haug LLP
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