Combination of herbicides and safeners

Details Combination of herbicides and safeners Combination of herbicides and safeners

1999-06-21

2003-01-28

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S130000, C504S138000

Reexamination Certificate

active

06511940

ABSTRACT:

DESCRIPTION
The invention relates to the technical field of the crop protection products, in particular herbicide/antidote combinations (active substance/safener combinations) which are outstandingly suitable for the use against competing harmful plants in crops of useful plants.
Some of the more recent herbicidal active substances which inhibit p-phydroxyphenylpyruvate dioxygenase (HPPDO) have very good use characteristics and can be employed at very low application rates against a broad spectrum of grass weeds and broad-leaved weeds (see, for example, M. P. Prisbylla et al., Brighton Crop Protection Conference—Weeds (1993), 731-738). However, many of these highly efficient active substances are not fully compatible with (i.e. not sufficiently selective in) some important crop plants such as maize, rice or cereals, so that their use is strictly limited. In certain crops, they can therefore not be employed, or at such low application rates that the desired broad herbicidal efficacy towards harmful plants is not guaranteed. Specifically, many of the abovementioned herbicides cannot be employed fully selectively against harmful plants in maize, rice, cereals or some other crops.
To overcome these disadvantages, it is known to employ herbicidal active substances in combination with a so-called safener or antidote. A safener for the purpose of the invention is a compound or a mixture of compounds which compensates for, or reduces, the phytotoxic properties of a herbicide towards useful plants without substantially reducing the herbicidal action against harmful plants.
The identification of a safener for a particular class of herbicides remains a difficult task since the exact mechanisms by which a safener reduces the harmful effect of herbicides are unknown. The fact that a compound in combination with a particular herbicide acts as a safener allows no conclusions as to whether such a compound also acts as a safener with other classes of herbicide. Thus, it has emerged that, when using safeners for protecting the useful plants from herbicide damage, the safeners may still have a number of disadvantages in many cases. These are:
the safener reduces the action of the herbicides against the harmful plants,
the useful-plant-protecting properties are insufficient,
in combination with a given herbicide, the spectrum of the useful plants in which the safener/herbicide is to be used is insufficiently wide,
a given safener may not be combined with a sufficiently large number of herbicides.
It was an object of the present invention to identify compounds which, in combination with the abovementioned herbicides are suitable for increasing the selectivity of these herbicides towards important crop plants.
Surprisingly, a group of compounds has now been found which, together with specific herbicides which act as HPPDO inhibitors, increase the selectivity of these herbicides towards important crop plants.
The invention therefore relates to a herbicidally active composition comprising a mixture of
A a herbicidally active amount of one or more compounds of the formula (I)
 in which
V is a radical selected from the group consisting of (V1) to (V4),
 where the symbols and indices have the following meanings:
R is hydrogen, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)haloalkoxycarbonyl, COOH, cyano, preferably hydrogen, (C
1
-C
4
)alkoxycarbonyl;
R
1
is hydrogen or a (C
1
-C
7
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkenyl, (C
1
-C
4
)alkyl-(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)halocycloalkyl, (C
1
-C
4
)alkylthiocycloalkyl, (C
1
-C
4
)haloalkyl, (C
2
-C
4
)haloalkenyl, preferably (C
3
-C
7
)cycloalkyl, (C
1
-C
4
)alkyl-(C
3
-C
7
)cydoalkyl;
R
2
is hydrogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)haloalkyl, halogen, (C
1
-C
4
)haloalkoxy, cyano, nitro, preferably hydrogen;
R
3
is hydrogen or a (C
1
-C
4
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkoxy-(C
1
-C
4
)alkyl, (C
1
-C
4
)alkylcarbonyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)halo-alkylsulfonyl, arylsulfonyl, arylcarbonyl-(C
1
-C
4
)alkyl, aryl-(C
1
-C
4
)alkyl, preferably hydrogen, (C
1
-C
4
) alkyl, arylsulfonyl, benzyl;
R
4
is hydrogen or a (C
1
-C
7
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
1
-C
4
)haloalkyl, phenyl, benzyl, preferably (C
1
-C
4
)alkyl;
R
5
is a (C
1
-C
12
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkoxy-(C
1
-C
4
)alkyl, (C
1
-C
4
)dialkoxy-(C
1
-C
4
)alkyl, (C
1
-C
4
)alkylthio, halogen, substituted or unsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl, tetrahydrothiopyran-3-yl, 1-methylthio-cyclopropyl, 2-ethylthiopropyl, preferably (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy;
R
6
is hydroxyl or a (C
1
-C
4
)carbon-containing radical such as (C
1
-C
4
)alkoxy, (C
1
-C
4
)haloalkoxy, formyloxy, (C
1
-C
4
)alkylcarbonyloxy, (C
1
-C
4
)alkylsulfonyloxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)haloalkylthio, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylsulfonyl, preferably hydroxyl, (C
1
-C
4
)alkoxy;
R
7
is a (C
1
-C
7
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl, (C
3
-C
7
)cycloalkyl, (C
1
-C
4
)alkyl-(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)halocycloalkyl, preferably (C
3
-C
7
)cycloalkyl;
R
8
is cyano or a (C
1
-C
4
)carbon-containing radical such as (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)alkylcarbonyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylaminocarbonyl, (C
1
-C
4
)dialkylaminocarbonyl, preferably cyano;
m is an integer from 0 to 6, preferably 0 to 3,
and Z is a radical selected from the group consisting of (Z1) to (Z4),
 where the symbols and indices have the following meanings:
R
9
is nitro, amino, halogen or a (C
1
-C
8
)carbon-containing radical such as (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
1
-C
4
)haloalkyl, (C
2
-C
4
)haloalkenyl, (C
2
-C
4
)haloalkynyl, (C
1
-C
4
)haloalkoxy, (C
1
-C
4
)haloalkylthio, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylthio, arylsulfonyl, arylsulfinyl, arylthio, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkoxy-(C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylcarbonyl, (C
1
-C
4
)alkylaminosuffonyl, (C
1
-C
4
)dialkylaminosulfonyl, (C
1
-C
4
)-alkylcarbamoyl, (C
1
-C
4
)dialkylcarbamoyl, (C
1
-C
4
)alkoxy-(C
1
-C
4
)alkyl, phenoxy, cyano, aryl, alkylamino, dialkylamino, preferably (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)haloalkoxy, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)alkyl-sulfonyloxy, (C
1
-C
4
)alkylsulfonylamino, (C
1
-C
4
)alkoxycarbonyl;
R
10
is substituted or unsubstituted benzyl, substituted or unsubstituted heteroaryl, heterocyclyl, preferably furanyl, thiazolyl, triazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolinyl, morpholino, and imidazolyl; heteroaryl-(C
1
-C
4
)alkyl, preferably triazolylmethyl, pyrazolylmethyl, thiazolylmethyl, di-(C
1
-C
4
)alkylphosphono-C
1
-C
4
)alkyl, preferably diethylphosphonomethyl, dimethylphosphonomethyl or SF
5
;
R
11
is identical or different hydrogen, (C
1
-C
4
)alkyl, halogen, preferably (C
1
-C
4
)alkyl;
R
12
is identical or different (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, halogen, (C
1
-C
4
)haloalkyl, (C
2
-C
4
)haloalkenyl, (C
2
-C
4
)haloalkynyl, (C
1
-C
4
)haloalkoxy, (C
1
-C
4
)haloalkylthio, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)haloalkylsulfonyl, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)haloalkylsulfinyl, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkyl-carbonyl, (C
1
-C
4
)alkylaminosulfonyl, (C
1
-C
4
)dialkylaminosulfonyl, (C
1
-C
4
)alkylcarbamoyl, (C
1
-C
4
)dialkylcarbamoyl, (C
1
-C
4
)alkoxyalkyl, phenoxy, nitro, cyano, aryl, di-(C
1
-C
4
)alkylphosphono-(C
1
-C
4
)alkyl, preferably (C
1
-C
4
)alkyl, halogen, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)alkoxycarbonyl;
q is 0, 1, 3 or 4;
r is 0, 1, 2 or 3;
t is 1 or 2;
u is 0, 1 or 2;
v is 1

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