Plant protecting and regulating compositions – Plant growth regulating compositions
Reexamination Certificate
1999-07-01
2002-02-19
Dees, Jose′ G. (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Reexamination Certificate
active
06348434
ABSTRACT:
BACKGROUND OF THE INVENTION
Emulsifiable concentrate (EC) formulations are favored liquid delivery systems for agriculturally active compounds. As a rule, conventional ECs contain an active ingredient, one or more surfactants which act as emulsifiers upon dilution of the EC with water, and a water immiscible solvent. Typical solvents for conventional EC formulations are aliphatic or aromatic hydrocarbons, as for example, xylene, Shellsol A or Solvesso 200. These solvents have very low solubilities in water and are capable of dissolving a wide range of active ingredients.
Due to the presence of the solvent, many pesticides formulated as an EC have advantages such as a higher degree of systemicity and higher overall activity compared to the same pesticide formulated as a wettable powder (WP), water dispersible granule (WG) or suspension concentrate (SC).
Such concentrates are easy to store and transport and various adjuvants may be added to increase the efficacy of the formulation. A good EC, however, requires that a stable emulsion is formed upon dilution with water, which emulsion does not separate upon standing. Furthermore, there should not be any crystallization of the active from the EC after water dilution. In addition, the EC itself has to be physico-chemically stable during extended storage periods and under widely varying storage temperatures.
International Patent Application WO 98/48624 suggests the improvement of the emulsion stability of ECs containing low amounts of a water-insoluble fluorinated active agricultural ingredients which optionally contains a diluent active agricultural ingredient, by using a comparably high amount of a water-insoluble C
6
-C
1
alkyl pyrrolidone. However, the C
6
-C
18
alkyl pyrrolidones are highly corrosive and too expensive to be used in a broad range herbicidal product for common use.
Moreover, WO 98/48624, preferably uses an ethoxylated nonyl phenol phosphate ester as an anionic surfactant. These surfactants may damage the environment due to their capability to form toxic metabolites and their use is not favored due to their suspected estrogenic activity.
Accordingly, it is an object of the present invention to provide novel, herbicidal ECs.
It is a further object of this invention to provide a stable, effective emulsifiable concentrate (EC) containing low amounts of at least one fluorinated herbicidal compound with high amounts of one or more herbicidal alkyl phenoxyacetates acting as a diluent which do not have the disadvantages of the ECs of the art.
It is also an object of the invention to provide methods for controlling undesired weed by contacting plants with a herbicidally effective amount of these EC formations upon dilution with water.
It is another object of the invention to provide selective herbicidal compositions obtainable by emulsifying the new ECs in water.
These and other objects and features of the invention will be more apparent from the detailed description set forth hereinbelow, and from the appended claims.
SUMMARY OF THE INVENTION
The present invention provides a novel stable, non-aqueous emulsifiable concentrate (EC) for herbicidally active compounds which consists essentially of
(a) 25 to 150 g/L of at least one fluorinated herbicidal compound,
(b) 400 to 900 g/L of one or more herbicidal alkyl phenoxyalkanoates,
(c) 10 to 100 g/L of at least one non-ionic surfactant,
(d) 10 to 100 g/L of at least one benzene sulfonate,
(e) 50 to 600 g/L of one or more solvents selected from the group consisting of aliphatic or aromatic hydrocarbons, methylated plant oils and water-miscible polar aprotic organic solvents, and
(f) optionally, up to 5 g/L of at least one defoamer:
These new emulsifiable concentrate formulations exhibit excellent selective herbicidal activity in various crops.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that the EC formulations consisting essentially of
(a) 25 to 150 g/L of at least one fluorinated herbicidal compound,
(b) 400 to 900 g/L of one or more herbicidal alkyl phenoxyalkanoates,
(c) 10 to 100 g/L of at least one non-ionic surfactant,
(d) 10 to 100 g/L of at least one benzene sulfonate,
(e) 50 to 600 g/L of one or more solvent selected from the group consisting of aliphatic or aromatic hydrocarbons, methylated plant oils and water-miscible polar aprotic organic solvents, and
(f) optionally, up to 5 g/L of at least one defoamer;
exhibit high physicochemical stability and excellent application properties.
As used herein in the new EC formulations, a “herbicidal compound” is a synthetic compound which has the capability of control undesired weeds in crops; and a “fluorinated herbicidal compound” is a synthetic compound which is substituted by at least one fluorine atom which has the capability of control undesired weeds in crops.
Suitable fluorinated herbicidal compounds are those which are solid at room temperature and are substantially insoluble in water, but soluble in an organic solvent.
Preferred fluorinated herbicides (a) are the compounds selected from the group consisting of:
acifluorfen, carfentrazone-ethyl, clodinafop-propargyl, diflufenican, dithiopyr, ethoxyfen-ethyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, fluazifop, fluchloralin, flufenacet (BAY FOE 5043 or fluthiamid), flumetsulam, flumioxazin, fluometuron, fluoroglycofen, flupoxam, fluridone, fluroxypyr, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, haloxyfop, isoxaflutole, lactofen, norflurazon, oxyfluorfen, picolinafen, propachlor, sulfentrazone, thiazopyr and trifluralin.
Most of these herbicidal compounds are described in “The Pesticide Manual,” 11th Edition, The British Crop Protection Council and The Royal Society of Chemistry, 1997, (hereinbelow abbreviated as “Pesticide Manual”).
Preferred for use in the present invention are the fluorinated herbicidal compounds of formula I
in which
R
1
and R
3
each independently represent a fluorine atom or a fluoroalkyl, preferably a C
1
-C
6
fluoroalkyl group, in particular a trifluoromethyl group;
R
2
represents a hydrogen atom or an optionally substituted alkyl or alkoxy group; and
m and n each independently represent an integer from 1 to 2.
Particularly preferred herbicidal compounds (a) are the picolinamides disclosed by EP-A-0 447 004, in particular those of formula I1
wherein R
1
and R3 are as described for formula I.
An especially preferred compound for use in the present invention is N-(4-fluorophenyl)-2-(3-&agr;,&agr;,&agr;-trifluoromethylphenoxy)-6-pyridinecarboxamide, also known as picolinafen.
The new ECs contain at least one fluorinated herbicide (a) and at least one herbicidal alkyl phenoxyacetate (b).
The herbicidal compounds can be, for example, compounds which possess a high herbicidal activity within a wide concentration range and/or at low dosages, and may be used in agriculture, in particular, for the selective control of undesired plants such as
Alopecurus myosuroides, Echinochloa crus
-
galli, Setaria viridis, Galium aparne, Stellaria media, Veronica persica, Lamium purpureum, Viola arvensis, Abutilon theophrasti, lpomoea purpurea
and
Amaranthus retroflexus
by pre- and post-emergence application, particularly in certain crops such as maize and rice.
Suitable herbicidal alkyl phenoxyalkanoates (b) are those which are liquid at room temperature and substantially insoluble in water, but soluble in an organic solvent.
Preferred alkyl phenoxyalkanoates are esters of 2-phenoxyacetic or 2-phenoxypropionic acid having a straight chained or branched C
2
-C
12
alkyl, in particular a branched C
4
-C
10
alkyl group. Most preferred are the 2-ethylhexyl esters.
Particularly preferred are the compounds of formula II
in which
R
4
each independently represents a halogen atom or a C
1-6
alkyl group,
R
5
and R
6
each independently represent a C
1-6
alkyl group,
R
7
represents a hydrogen atom or a methyl group, and
t represents an integer from 1 to 3.
Most preferred are the compounds selected from the group consisting of: 2-ethylhexyl(4-chloro-2-methylphenoxy)-acetate [also known as MCPA-
BASF - Aktiengesellschaft
Dees Jose′ G.
George Konata M.
Maurer Barbara V.
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