Herbicidal compositions

Details Herbicidal compositions Herbicidal compositions

2001-07-23

2003-06-03

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S214000, C504S333000, C504S363000

Reexamination Certificate

active

06573217

ABSTRACT:

The invention lies in the technical field of the crop protection products, in particular active substance/silicone surfactant/humectant combinations.
To control undesired harmful plants, a multiplicity of herbicides is available to the user, which can be employed as a function of the biological properties of the herbicides, the species of harmful plants to be controlled and the crop plant species. In this context, the herbicidal active substances are formulated in such a way that their application is as optimal as possible and that they have high activity. A variety of formulation auxiliaries such as wetters, dispersants, emulsifiers, antifoams, as solvents or fillers are employed for this purpose.
However, the reliability and the level of the control of the harmful plants vary as a function of environmental factors such as temperature, atmospheric humidity, soil moisture, light incidence, precipitation or soil type, which can lead to follow-up treatments in the event of poor activity or to the damage of useful plants in the case of unduly high rates of application.
A more reliable activity also has ecological advantages. To avoid poor activity, the user frequently increases the amount of active substance to be applied. However, the disadvantage of this procedure is that the active substances' potential to affect soil fauna, to leach from the soil or to enter surface waters increases.
The effect of humectants on a variety of pesticides is described in Adjuvants for Agrochemicals, CRC Press, Inc. (1992), pp. 261-271. WO 89/02570 discloses that humectants in conjunction with silicone surfactants can increase the activity of herbicides.
It was an object of the present invention to provide a herbicidal composition with improved level of action and improved reliability of action. This object is achieved by a herbicidal composition comprising specific sulfonamides in combination with silicone surfactants and humectants.
The present invention thus relates to a herbicidal composition comprising
a) one or more herbicidal active substances from the group of the grass-controlling sulfonamides,
b) one or more silicone surfactants, and
c) one or more humectants.
The grass-controlling sulfonamides which are present in the herbicidal composition according to the invention as component a) are understood to be sulfonamides which inhibit the growth of monocotyledonous harmful plants in a sustained manner. In particular, they encompass sulfonamides which are recommended by the manufacturer for use against monocotyledonous harmful plants, for example in the product brochures in question or in Pesticide Manual, 12th edition (2000), British Crop Protection Council.
Examples of especially suitable active substances from the group of the grass-controlling sulfonamides are grass-controlling sulfonylureas such as flucarbazone (MKH 6561), procarbazone (MKH 6562), sulfosulfuron, rimsulfuron, nicosulfuron, flupyrsulfuron, iodosulfuron-methyl, foramsulfuron (Agrow No. 338, PJB Publications Ltd. 1999, page 26) and mesosulfuron-methyl and/or their salts (Agrow No. 347, PJB Publications Ltd. 2000, page 22).
Very especially preferred are sulfonylureas of the formula (I) and/or their salts
in which
R
1
is CO—R
a
, in which R
a
is OH, C
1
-C
4
-alkoxy or NR
b
R
c
, in which R
b
and R
c
independently of one another are identical or different and are H or C
1
-C
4
-alkyl,
R
2
is halogen or (A)
n
—NR
d
R
e
in which n is zero or 1, A is a group CR′R″ in which R′ and R″ independently of one another are identical or different and are H or C
1
-C
4
-alkyl, R
d
is H or C
1
-C
4
-alkyl and R
e
is an acyl radical,
R
3
is H or C
1
-C
4
-alkyl,
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 abovementioned radicals 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, and
Z is CH or N.
Examples of sulfonylureas of the formula (I) and/or their salts are mesosulfuron-methyl, mesosulfuron-methyl-sodium, iodosulfuron-methyl, iodosulfuron-methyl-sodium, foramsulfuron and foramsulfuron-sodium.
Examples of suitable salts of the sulfonamides a) such as sulfonylureas are compounds in which the hydrogen of the —SO
2
—NH-group is replaced by an agriculturally suitable cation. Examples of these salts are metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium salts and potassium salts, or else ammonium salts or salts with organic amines. Equally, salt formation can be effected by an addition reaction of an acid with basic groups such as, for example, amino and alkylamino. Acids which are suitable for this purpose are strong inorganic and organic acids, for example HCl, HBr, H
2
SO
4
or HNO
3
.
The silicone surfactants present in the herbicidal composition according to the invention as component b) are understood as surfactants with at least one silicon atom, preferably 2 to 2000 silicon atoms.
The silicone surfactants b) which are present in the herbicidal compositions according to the invention are, for example, polyalkylene oxide-modified dimethylpolysiloxane copolymers which are commercially available for example under the trademark Silwet by Witco/Osi Corp., which was Union Carbide Corporation (USA). They are surface-active materials with discrete hydrophilic and hydrophobic segments. They have the following formula (I)
in which a is an integer of 3-24, b an integer of 0-15, x an integer of 0-3 and y an integer of 1-5, and Z is hydrogen, C
1
-C
3
-alkyl or an acyl group having 2 to 4 carbon atoms.
The Silwet silicone surfactants also include the products described in the Union Carbide brochure entitled “Silicones For the Agricultural Industry” SUI-356, 6/84, 5M and in “Surface Active Copolymers”, SUI-394A, 7185-5M, also from Union Carbide. Both brochures are incorporated in their entirety into the present description by reference.
Further suitable silicone surfactants which can be used for the purposes of the present invention are, for example SF-1188 (General Electric Company, Silicone Products Division, Rubber & Fluid Products Department, Waterford, N.Y. 12188), Silwet L-7607, the silicone glycols Q2-5309, Q2-5152, Q2-5852 and Q2-5853 by Dow Corning Corporation, Midland, Mich., mixtures of these, and similar products. Silicone surfactants of the formula (I) are described in particular in U.S. Pat. No. 3,299,112, which is incorporated in its entirety into the present description by reference. An especially preferred silicone surfactant has the formula Me
3
SiO[MeO(C
2
H
4
O)
7
C
3
H
6
SiMeO]SiMe
3
in which Me=methyl.
Other suitable silicone surfactants b) are silicone glycols, for example of the formula (II):
where Me hereinbelow denotes a methyl radical, R a divalent alkylene group having 2 to 6 carbon atoms, such as ethylene, trimethylene, tetramethylene or hexamethylene, preferably trimethylene, m is an integer of 3-24 and Z is hydrogen, a C
1
-C
3
-alkyl radical or an acyl group having 2 to 4 carbon atoms, preferably an acetoxy group.
The above-described silicone glycols are known in the art and can be prepared for example by coupling the corresponding glycol, which has a terminal allyl group, to a bis-siloxane structure which has a hydrogen atom at the central silicon atom, where the bis-siloxane structure can be represented as follows (in which Me=methyl):
In general, this coupling reaction is carried out in the presence of a platinum catalyst. It is known in the art that not all the glycol with the terminal allyl group is reacted in such coupling reactions and remains in the silicone glycol end product as contaminant. The present invention also encompasses herbicidal compositions with such contaminants.
Silicone glycol/silicone alkane terpolymers are also suitable

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