Plant protecting and regulating compositions – Plant growth regulating compositions
Reexamination Certificate
2000-08-17
2002-07-16
Pryor, Alton (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
C504S127000, C504S206000
Reexamination Certificate
active
06420311
ABSTRACT:
TECHNICAL FIELD
This invention relates to surfactants, and, more particularly, to surfactants that enhance the bioefficacy of herbicides, and to herbicide compositions comprising such surfactants.
BACKGROUND OF THE INVENTION
Herbicide compositions are often characterized according to the identity of the active ingredient, and by the mode by which the active ingredient causes vegetation necrosis. Regardless of the active ingredient, most herbicides cause vegetation necrosis by interfering with one or more vital biological processes essential to the vegetation's survival. Yet, before the active ingredient of a herbicide can interfere with such biological processes, the active ingredient must somehow be absorbed into the vegetation. Unfortunately, this absorption is often hindered by the chemical nature of the active ingredient.
Accordingly, in addition to active ingredients, most herbicide compositions also comprise other components, commonly termed adjuvants, that enhance the performance and absorption of the active ingredient. One class of adjuvants that is frequently used is surfactants. Surfactants are useful in herbicide compositions because they tend to both enhance the absorbing properties of the active ingredient, as well as facilitate application of the herbicide.
The literature discloses various classes of surfactants, including alkoxylated diamines. However, the literature appears to lack any reference to the use of alkoxylated polyether diamines or esterified alkoxylated polyether diamines as suitable herbicide adjuvants. It is expected that both alkoxylated polyether diamines and esterified alkoxylated polyether diamines will function to improve the bioefficacy of herbicide compositions containing such surfactants. Accordingly, the present invention is directed toward surfactant adjuvants that include alkoxylated polyether diamines, esterified alkoxylated polyether diamines, and mixtures thereof, herbicide compositions comprising such surfactant adjuvants, and a method of controlling unwanted vegetation using such herbicide compositions.
SUMMARY OF THE INVENTION
The present invention provides for surfactants that are expected to further improve the bioefficacy of herbicides. The surfactants comprise alkoxylated polyether diamines (I), esterified alkoxylated polyether diamines (IIa) or (IIb), or mixtures thereof, with the following general structure:
where R
1
, R
2
, R
3
, and R
4
are each independently hydrogen, CH
3
, or CH
2
CH
3
; a, b, and c each vary from zero to about forty; R
5
and R
6
are each independently a straight or branched chain alkenyl group with from about two to about six carbon atoms; d, e, f, g, h, i, j, and k each vary from zero to about twenty-two; each R
7
is independently either a hydrogen or has the following general structure:
where each R
8
is independently a linear or branched alkyl or alkenyl with less than about twenty-two carbon atoms; and, R
9
is an alkyl or alkenyl with less than about twenty-two carbon atoms.
The present invention also provides for herbicide compositions that contain a surfactant of the present invention. The herbicide compositions comprise a herbicidal active ingredient, a surfactant of the present invention, and optionally, one or more formulation aids. The herbicide compositions of the present invention are expected to have a reduced tendency to cause eye and skin irritation.
The present invention additionally provides for a method of controlling unwanted weeds or vegetation using the herbicide compositions of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
The present invention relates to surfactants that are expected to enhance the bioefficacy of herbicides, herbicide compositions comprising such surfactants, and a method of controlling unwanted weeds or vegetation using the herbicide compositions of the present invention. The surfactants of the present invention are expected to enhance the bioefficacy of herbicides because they have twice the amine content as traditional herbicide surfactants (i.e. tallowamine ethoxylates). This increased amine content will likely enhance the ability of the herbicide to penetrate the tissue of the vegetation, thereby increasing the bioefficacy of the herbicide. In addition, the surfactants of the present invention are expected to have improved handling characteristics, including a lower volatility, due to the polyether “interior” structure of the surfactants. Further, when added to glyphosate solutions, the surfactants of the present invention produce cloud points at or above about 65° C., the commercial standard for glyphosate herbicide solutions.
The surfactants of the present invention may be used in conjunction with any number of herbicidal active ingredients, including, but not limited to, various salts of glyphosate and gluphosinate. However, the use of the surfactants of the present invention with glyphosate is of particular interest because glyphosate is probably the most widely used herbicide.
Glyphosate, or N-phosphonomethylglycine, is a broad-spectrum herbicide that is useful on essentially all annual and perennial plants, including, grasses, broad-leaved weeds, and woody plants. Glyphosate promotes plant necrosis by inhibiting aromatic amino acid biosynthesis. By inhibiting aromatic amino acid synthesis, and thereby protein synthesis, glyphosate initially suppresses plant growth, which is soon followed by plant necrosis.
In its free acid form, glyphosate has a low water solubility. As such, water-based glyphosate compositions typically contain a water soluble salt of glyphosate, such as the isopropylamine salt. For example, many commercially available herbicide compositions contain the water soluble mono-isopropylamine salt of glyphosate. Glyphosate, and various water soluble derivatives of glyphosate are available from numerous manufactures.
The surfactants of the present invention may be prepared by reacting a polyether diamine with one or more lower molecular weight alkylene oxides, at a temperature from about 100° C. to about 110° C., at a pressure of about 60 psig, and in the presence of a suitable alkaline catalyst. The polyether diamines may be alkoxylated to varying degrees. Preferably, the resulting polyether diamines have an alkylene oxide content less than about 90 percent.
The polyether diamine used to make the alkoxylated polyether diamine surfactants of the present invention should have the following general structure:
where R
1
, R
2
, R
3
, and R
4
are each independently hydrogen, CH
3
, or CH
2
CH
3
; and a, b, and c each vary from zero to about forty. Preferably, the polyether diamine comprises a JEFFAMINE® diamine (commercially available from the Huntsman Corporation, Houston, Tex.).
The lower molecular weight alkylene oxide may comprise one or more alkylene oxides with less than about six carbon atoms. Preferably, the alkylene oxide comprises ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof.
Any suitable alkoxylation catalyst may be used in the alkoxylation process. Preferably, the catalysts comprises a 45% aqueous solution of potassium hydroxide.
The resulting alkoxylated polyether diamine surfactants of the present invention have the following general structure:
where R
1
, R
2,
R
3,
and R
4
are each independently hydrogen, CH
3,
or CH
2
CH
3;
a, b, and c each vary from zero to about forty; R
5
and R
6
are each independently a straight or branched chain alkenyl group with from about two to about six carbon atoms; and d, e, f, g, h, i, j, and k each vary from zero to about twenty-two.
After preparation, the resulting alkoxylated polyether diamine surfactants of the present invention may then be blended with one or more formulation aids before being combined with a herbicide. Such formulation aids may include neutralizing agents, water, anti-freeze agents, or mixtures thereof. The neutralizing agents may include, but are not limited to, hydrochloric acid or sulfuric acid, carboxylic acids with less than about twenty carbon atoms, sulfonic acids, acid sulfates, acid phosphate es
Ashrawi Samir S.
Stridde Howard Meyer
Huntsman Petrochemical Corporation
Peffer Nicole
Pryor Alton
Stolle Russell R.
Whewell Christopher J.
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