Herbicidal Compositions

Details Herbicidal Compositions Herbicidal Compositions

2001-06-15

2004-12-28

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

Reexamination Certificate

active

06835695

ABSTRACT:

The invention is in the technical field of the crop protection products, in particular, the invention relates to herbicidal compositions with a content of particular herbicidal compounds and specific surfactants which are outstandingly suitable for controlling harmful plants in crops.
Some of the more recent herbicidal active ingredients which inhibit p-hydroxyphenyl-pyruvate dioxygenase (HPPDO) show very good properties on use and can be employed in very low rates of application against a broad spectrum of graminaceous and broad-leaved weeds (see, for example, Prisbylla et al., Brighton Crop Protection Conference—Weeds (1993), 731-738).
U.S. Pat. No. 5,627,131 and EP 551650 disclose specific mixtures of herbicides with pre-emergence safeners.
It is furthermore known from various publications that herbicides from the series of the benzoylcyclohexanediones, being inhibitors of para-hydroxyphenyl-pyruvate dioxygenase, are based on the same mechanism of action as those from the series of the benzoylisoxazoles; in this context cf. J. Pesticide Sci. 21, 473-478 (1996); Weed Science 45, 601-609 (1997), Pesticide Science 50, 83-84, (1997) and Pesticide Outlook, 29-32, (December 1996). Moreover, it is known from Pesticide Science 50, 83-84, (1997) that, under certain conditions, benzoylisoxazoles can undergo rearrangements to give benzoyl-3-oxopropionitriles.
It is likewise known that the abovementioned herbicidal compounds can be combined with surfactants to produce standard formulations.
Thus, for example, WO 98/31223 describes the use of mixtures comprising a fatty acid ester or an alkoxy fatty acid, a terpene derivative and a pesticide. EP-A 0 968 649 describes dry formulations of herbicides comprising ethoxylated fatty alcohols. The herbicide-comprising mixtures mentioned therein do not always exhibit the desired potent herbicidal action.
The object of the present invention was to provide herbicidal compositions which have a particularly potent herbicidal action.
Surprisingly, it has now been found that herbicidal compositions comprising the compounds of the formula (I) stated hereinbelow in combination with specific surfactants achieve this object.
Thus, the present invention relates to herbicidal compositions comprising
A) one or more compounds of the formula (I)
where V is an unsubstituted or substituted heterocyclyl radical or a radical —CR
&agr;
═CR
&bgr;
R
&bgr;1
, where R
&agr;
and R
&bgr;
are identical or different carbon-containing C
1
-C
40
radicals which together can form an unsubstituted or substituted ring, and R
&bgr;1
is OH or a carbon-containing C
1
-C
40
radical, and Z is an unsubstituted or substituted aryl radical, and
B) one or more surfactants comprising, as structural element, at least 10, preferably 10-200, alkylene oxide units.
Surfactant B) preferably contains 10-150 alkylene oxide units, one or more carbon-containing C
1
-C
40
radicals and, if appropriate, one or more polar functional groups.
The term alkylene oxide units is preferably understood as meaning units of C
2
-C
10
-alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or hexylene oxide, it being possible for the units within the surfactant to be identical or different from each other.
Suitable polar functional groups include anionic groups such as carboxylate, carbonate, sulfate, sulfonate, phosphate or phosphonate, cationic groups such as groups with a cationic nitrogen atom, for example a pyridinium group or an —NR
y
3
-group, where R
y
radicals are identical or different and are H or an unsubstituted or substituted C
1
-C
10
-hydrocarbon radical such as C
1
-C
10
-alkyl, electrically neutral, polar groups such as carbonyl, imine, cyano or sulfonyl, or betainic groups such as
where m=1, 2, 3, 4 or 5 and R
x
are identical or different and are unsubstituted or substituted C
1
-C
10
-hydrocarbon radicals such as C
1
-C
10
-alkyl.
Preferably, the composition according to the invention comprises, as component B), one or more surfactants of the general formula (II)
R
&ggr;
-(EO)
x
(PO)
y
(EO)
z
—R
&dgr;
  (II)
where
EO denotes an ethylene oxide unit,
PO denotes a propylene oxide unit,
x denotes an integer from 1 to 50,
y denotes an integer from 0 to 50,
z denotes an integer from 0 to 50,
where the total (x+y+z)≦10 and ≧150, and
R
&ggr;
denotes OH, an unsubstituted or substituted C
1
-C
40
-hydrocarbonoxy radical, an O-acyl radical such as O—COR
1
, O—CO—OR
1
, O—CO—NR
I
R
II
, O—P(O)(R
I
)[(EO)
u
(OR
II
)] or O—P(O)[(EO)
u
(OR
I
)][(EO)
u
(OR
I
)] or NR
I
R
II
or [NR
I
R
II
R
III
]
⊕
X
⊖
, where R
I
, R
II
, and R
III
are identical or different and denote H or an unsubstituted or substituted C
1
-C
30
-hydrocarbon radical which can optionally be bound via a group (EO)
w
, where w is an integer from 1 to 50, X
⊖
is an anion (for example the anion of an organic acid such as a carboxylic acid anion, for example acetate or lactate, or the anion of an inorganic acid such as ½ sulfate, [O—SO
3
—CH
3
]
⊖
, sulfonate, ⅓ phosphate, phosphonate or halide such as Cl
⊖
or Br
⊖
), and u, v independently of one another denote an integer from 0 to 50, and
R
&dgr;
denotes H, an unsubstituted or substituted C
1
-C
40
-hydrocarbon radical, an acyl radical such as COR
I
, CO—OR
I
, CO—NR
I
R
II
, P(O)(R
I
)[(EO)
u
(OR
II
)] or P(O)[(EO)
u
(OR
I
)][(EO)
v
(OR
II
)] or NR
I
R
II
or [NR
I
R
II
R
III
]
⊕
X
⊖
, where R
I
, R
II
and R
III
are identical or different and denote H or an unsubstituted or substituted C
1
-C
30
-hydrocarbon radical which can optionally be bound via a group (EO)
w
, where w is an integer from 1 to 50, X
⊖
is an anion (for example the anion of an organic acid such as a carboxylic acid anion, for example acetate or lactate, or the anion of an inorganic acid such as ½ sulfate, [O—SO
3
—CH
3
]
⊖
, sulfonate, ⅓ phosphate, phosphonate or halide such as Cl
⊖
or Br
⊖
), and u, v independently of one another denote an integer from 0 to 50.
The abbreviation EO in formula (II) denotes an ethylene oxide unit, also when used in the definition of R
&ggr;
and R
&dgr;
.
Preferred surfactants of the formula (II) are those where the total (x+y+z)≧10 and ≦150, preferably 11-100, especially preferably 12-80, and
R
&ggr;
denotes OH, an unsubstituted or substituted C
1
-C
30
-hydrocarbonoxy radical, preferably a C
4
-C
20
-hydrocarbonoxy radical, such as a C
8
-, C
10
-, C
12
-, C
13
-(for example isotridecyl),C
14
-,C
16
-, C
18
-, C
20
-alkoxy radical, -alkenyloxy radical or -alkynyloxy radical, or an unsubstituted or substituted C
6
-C
14
-aryloxy radical, for example a C
6
-C
14
-aryloxy radical which is monosubstituted or polysubstituted by C
1
-C
20
-alkyl, such as p-octylphenoxy, p-nonylphenoxy, 2,4-dibutylphenoxy, 2,4,6-tri-isobutylphenoxy, 2,4,6-tri-n-butylphenoxy or 2,4,6-tri-sec-butylphenoxy, or R
&ggr;
denotes O—CO—R
I
, O—COOR
I
, NR
I
R
II
or [NR
I
R
II
R
III
]
⊕
X
⊖
, where R
I
, R
II
and R
III
are identical or different or denote H, an unsubstituted or substituted C
1
-C
30
-hydrocarbon radical, preferably a C
4
-C
20
-hydrocarbon radical, such as a C
8
-, C
10
-, C
12
-, C
13
-(for example isotridecyl), C
14
-, C
16
-, C
18
-, C
20
-alkyl radical, -alkenyl radical or -alkynyl radical, or an unsubstituted or substituted C
6
-C
14
-aryl radical, for example a C
6
-C
14
-aryl radical which is mono- or polysubstituted by C
1
-C
20
-alkyl such as p-octylphenyl, p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl, 2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl, or R
I
, R
II
and R
III
are identical or different and are (EO)
w
—R
IV
, where R
IV
is H or an unsubstituted or substituted C
1
-C
20
-hydrocarbon radical, such as a C
8
-, C
10
-, C
12
-, C
13
-(for example isotridecyl), C
14
-, C
16
-, C
18
-, C
20
-alkyl radical, -alkenyl radical or -alkynyl radical

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