Herbicidal compositions

Details Herbicidal compositions Herbicidal compositions

2001-06-15

2004-06-01

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S213000, C504S214000, C504S215000, C504S358000

Reexamination Certificate

active

06743754

ABSTRACT:

The invention lies in the technical field of the crop protection products; in particular, the invention relates to herbicidal compositions comprising certain sulfonylureas and/or their salts and specific surfactants, which compositions are outstandingly suitable for controlling harmful plants in crop plants.
The use of sulfonylureas as active component of crop protection compositions is known (for example EP-A-007 687, EP-A-030 138). Likewise, it is known to combine sulfonylureas such as nicosulfuron (Accent®) with surfactants (for example Weed Technology 1999, Vol. 13, pages 737-740).
It was an object of the present invention to provide herbicidal compositions having particularly high herbicidal activity.
Surprisingly, it has now been found that this object is achieved by herbicidal compositions which comprise certain sulfonylureas in combination with specific surfactants.
The present invention thus relates to herbicidal compositions comprising
A) one or more sulfonylureas of the formula (I) and/or their salts
in which
R
1
is C
2
-C
4
-alkoxy or CO—R
a
, where R
a
is OH, C
1
-C
6
-alkoxy or NR
b
R
c
, where R
b
and R
c
independently of one another are identical or different and are H or C
1
-C
6
-alkyl,
R
2
is halogen or (A)
n
—NR
d
R
e
, where n is zero or 1, A is a group CR
f
R
g
, where R
f
and R
g
independently of one another are identical or different and are H or C
1
-C
6
-alkyl, R
d
is H or C
1
-C
6
-alkyl and R
e
is H, C
1
-C
6
-alkyl or an acyl radical, where R
d
and R
e
may also form a heterocyclic ring and where, if R
1
is C
2
-C
4
-alkoxy, R
2
may also be H,
R
3
is H or C
1
-C
6
-alkyl,
m is zero or 1,
X and Y independently of one another are identical or different and are C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkylthio, where each of the three radicals mentioned is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio, or are C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-alkenyloxy or C
3
-C
6
-alkynyloxy, preferably C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy,
Z is CH or N,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 C
1
-C
40
-carbon-containing radicals and optionally one or more polar functional groups.
The term alkylene oxide units is preferably to be understood as meaning units of C
2
-C
10
-alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or hexylene oxide, where the units within the surfactant may be identical to or different from one another.
Suitable polar functional groups are, for example, anionic groups, such as carboxylate, carbonate, sulfate, sulfonate, phosphate or phosphonate, cationic groups, such as groups having a cationic nitrogen atom, for example a pyridinium group or an —NR
y
3
group, where R
y
are identical or different and are H or unsubstituted or substituted C
1
-C
10
-hydrocarbon radicals, 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 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 formula (II)
R
4
−(EO)
x
(PO)
y
(EO)
z
−R
5
  (II)
in which
EO is an ethylene oxide unit,
PO is a propylene oxide unit,
x is an integer from 1 to 50,
y is an integer from 0 to 50,
z is an integer from 0 to 50,
where the sum (x+y+z) is ≧10 and ≦150, and
R
4
is OH, an unsubstituted or substituted C
1
-C
40
-hydrocarbonoxy radical, an O-acyl radical, such as O—COR
I
, O—CO—OR
I
, O—CO—NR
I
R
II
, O—P(O)(R
I
)[(EO)
u
(OR
II
)] or O—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 are H or an unsubstituted or substituted C
1
-C
30
-hydrocarbon radical which may be attached via a group (EO)
w
, where w is an integer from 1 to 50, X
⊖
being 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 and v independently of one another being integers from 0 to 50, and
R
5
is 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 are H or an unsubstituted or substituted C
1
-C
30
-hydrocarbon radical which may be attached via a group (EO)
w
, where w is an integer from 1 to 50, X
⊖
being 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 and v independently of one another being integers from 0 to 50.
The abbreviation EO in formula (II) denotes an ethylene oxide unit, likewise when used in the definition of R
4
and R
5
.
Preference is given to surfactants of the formula (II) in which the sum (x+y+z) is ≧10 and ≦150, preferably 11-100, particularly preferably 12-80, and
R
4
is OH, an unsubstituted or substituted C
1
-C
30
-, preferably 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, for example mono- or poly-C
1
-C
20
-alkyl-substituted, C
6
-C
14
-aryloxy radical, such as p-octylphenoxy, p-nonylphenoxy, 2,4-dibutylphenoxy, 2,4,6-triisobutylphenoxy, 2,4,6-tri-n-butylphenoxy or 2,4,6-tri-sec-butylphenoxy, or R
4
is 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 and are H, an unsubstituted or substituted C
8
-C
30
-, preferably C
4
-C
20
-, hydrocarbon radical, such as a C
8
-, C
10
-, C
12
-, C
3
- (for example isotridecyl-), C
14
-, C
16
-, C
18
-, C
20
-alkyl radical, -alkenyl radical or -alkynyl radical, or an unsubstituted or substituted, for example mono- or poly-C
1
-C
20
-alkyl-substituted, C
6
-C
14
-aryl radical, such as p-octylphenyl, p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-triisobutylphenyl, 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 (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
-, C12,C
13
- (for example isotridecyl-), C
14
-, C
16
-, C18-, C
20
-alkyl radical, -alkenyl radical or -alkynyl radical, or an unsubstituted or substituted, for example mono- or poly-C
1
-C
20
-alkyl-substituted, C
6
-C
14
-aryl radical, such as p-octylphenyl, p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-triisobutylphenyl, 2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl, and w is an integer from 1 to 50, X
⊖
being an anion, and
R
5
is H, an unsubstituted or substituted C
1
-C
30
-, preferably C
1
-C
20
-, hydrocarbon radical, such as a C
1
-, C
2
-, C
3
-, C
4
-, C
5
-, C
6
-, C8-, 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, for example mono- or poly-C
1
-C
20
-alkyl-substituted, C
6
-C
14
-aryl radical, such as p-octylphenyl, p

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