Herbicidal composition

Details Herbicidal composition Herbicidal composition

2001-12-18

2004-02-17

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S359000

Reexamination Certificate

active

06693063

ABSTRACT:

The present invention relates to the field of chemical crop protection, in particular to combinations of specific herbicides of the hydroxybenzonitrile type with specific surfactants.
Herbicides of the hydroxybenzonitrile type, such as ioxynil or bromoxynil and derivatives thereof, such as salts or esters, are suitable for controlling undesirable vegetation, for example in crops such as corn or wheat.
It is also known that the abovementioned herbicidal compounds can be combined with surfactants for preparing standard formulations.
It was an object of the present invention to provide herbicidal compositions with particularly high herbicidal activity.
Surprisingly, it has now been found that this object is achieved by herbicidal compositions comprising herbicides of the hydroxybenzonitrile type of the formula (I) from below in combination with specific surfactants.
Accordingly, the present invention relates to herbicidal compositions, comprising
A) one or more compounds of the formula (I)
in which
Hal
1
and Hal
2
are identical or different halogen atoms such as F, Cl, Br, I, preferably Br or I, and
R
1
is H, a cation or a C
1
-C
20
-carbon-containing radical, and
B) one or more surfactants, comprising as structural elements at least 12 alkylene oxide units, preferably 12-200 alkylene oxide units.
Preferred compounds of the formula (I) are compounds in which R
1
is H, a C
1
-C
20
-carbon-containing radical, for example a C
1
-C
20
-acyl radical, or a cation such as an ammonium ion, for example
⊕
NH
4
,
⊕
NH
3
CH
2
CH
2
OH,
⊕
NH
2
(CH
2
CH
2
OH)
2
,
⊕
NH(CH
2
CH
2
OH)
3
,
⊕
N(CH
2
CH
2
OH)
4
,
⊕
NH
3
(C
1
-C
18
)-alkyl,
⊕
NH
2
[(C
1
-C
18
)-alkyl]
2
,
⊕
NH[(C—C
18
)-alkyl]
3
or
⊕
N[(C
1
-C
18
)-alkyl]
4
, a sulfonium ion, for example
⊕
S[(C
1
-C
6
)-alkyl]
3
, a phosphonium ion, for example
⊕
P[(C
1
-C
6
)-alkyl]
4
, an alkali metal ion, for example Na
⊕
or K
⊕
, or an alkaline earth metal ion, for example ½ Ca
2⊕
, or ½ Mg
2⊕
, or a transition group metal ion, for example, ½ Zn
2⊕
.
A C
1
-C
20
-carbon-containing radical R
1
can be unsubstituted or substituted, linear, branched or cyclic, saturated or unsaturated, aliphatic or (hetero)aromatic. Suitable substituents are, for example, one or more radicals from the group consisting of oxo, (═O), OH, (C
1
-C
6
)-(halo)alkyl or halogen (F, Cl, Br, I). R
1
is preferably a carbon-containing acyl radical, such as (C
1
-C
19
)-alkylcarbonyl, preferably (C
1
-C
10
)-alkylcarbonyl such as propylcarbonyl (butyrate), hexylcarbonyl (heptanoate) or heptylcarbonyl (octanoate).
Preference is furthermore given to compounds of the formula (I) in which Hal
1
and Hal
2
are identical halogen atoms, in particular Br or I.
The formula (I) also embraces all stereoisomers having the same topological attachment of the atoms, and mixtures thereof. Such compounds contain one or more asymmetrically substituted carbon atoms or else double bonds which are not specifically shown in the general formulae. The possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers and tautomers, defined by their specific spatial form, can be obtained by customary methods from mixtures of the stereoisomers or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
Compounds of the formula (I) are known, for example, from C. D. S. Tomlin, “The Pesticide Manual”, 12th edition (1999), The British Crop Protection Council, (ISBN 19 01 39 61 26); p. 110ff and p. 548ff.
Particularly preferred compounds of the formula (I) are, for example, bromoxynil (A1) and ioxynil (A5) and their salts and esters, such as bromoxynil-sodium (A2), bromoxynil-potassium (A3), bromoxynil-heptylcarbonyl (=bromoxynil-octanoate) (A4), ioxynil-sodium (A6), ioxynil-potassium (A7), ioxynil-heptylcarbonyl (=ioxynil-octanoate) (A8), bromoxynil-hexylcarbonyl (=bromoxynil-heptanoate) (A9), bromoxynil-propylcarbonyl (=bromoxynil-butyrate) (A10), ioxynil-hexylcarbonyl (=ioxynil-heptanoate) (A11) and ioxynil-propylcarbonyl (=ioxynil-butyrate) (A12) and mixtures thereof.
The surfactant B) preferably contains 12-200 alkylene oxide units, one or more C
1
-C
40
-carbon-containing radicals and, if appropriate, 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 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 radicals from the group consisting of H and 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
in which 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.
As component B), the composition according to the invention preferably comprises one or more surfactants of the formula (II)
R
&ggr;
—(EO)
x
(PO)
y
(EO)
z
—R
&dgr;
  (II)
in which
EO is an ethylene oxide unit,
PO is a propylene oxide unit,
x is an integer from 0 to 50, preferably 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)≧12 and ≦150, and
R
&dgr;
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
1
)[(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, and where X
⊖
is an anion (for example the anion of an inorganic 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, are integers from 0 to 50, and
R
&dgr;
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, and where 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 and v, independently of one another, are integers from 0 to 50.
The abbreviations EO and PO in formula (II) denote an ethylene oxide unit and a propylene oxide unit, respectively, also when used elsewhere in the description.
Preference is given to surfactants of the formula (II), in which the sum (x+y+z)≧12 and ≦150, preferably 12-100, particularly preferably 12-80, and
R
&ggr;
is OH, an unsubstituted or substituted C
1
-C
30
-hydro

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