Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-05-20
2001-05-01
Shah, Mukund J. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S213000, C544S189000, C544S194000, C544S321000, C544S331000
Reexamination Certificate
active
06225260
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to quaternary ammonium salts of a sulfonylurea, methods for preparing quaternary ammonium salts of a sulfonylurea, and the use of such compounds as pesticides, herbicides, fungicides, and plant growth regulating agents.
BACKGROUND OF THE INVENTION
Sulfonylureas are known to be highly effective as herbicides and plant growth regulators. See, for example, U.S. Pat. Nos. 4,127,405; 4,169,719; 5,391,539; 5,488,029; 5,508,441; 5,580,842; 5,591,694; 5,599,769; 5,612,286; 5,635,450; 5,658,854; 5,688,745; 5,696,053; 5,714,436; and 5,747,421. However, aqueous solutions of sulfonylureas frequently degenerate within days and, therefore, cannot be stored for long periods of time.
There have been previous attempts to stabilize sulfonylureas in aqueous suspension compositions. For example, Sandell, U.S. Pat. No. 4,599,412, discloses a process for the preparation of solution formulations of sulfonylureas containing an agriculturally suitable cation, such as ammonium or substituted ammonium. Sandell also generally discloses that ammonium and quaternary ammonium salts of sulfonylureas can be prepared by treating the corresponding N-protonated sulfonylurea with an ammonium salt solution. Sandell notes, however, that these compounds are still susceptible to the degradative effects of moisture and impurities present in at least trace quantities in all practical solvent systems.
Hyson, U.S. Pat. No. 4,936,900, discloses compositions consisting essentially of a sulfonylurea and a carboxylic or an inorganic acid. No quaternary ammonium salts are disclosed.
Ort et al., U.S. Pat. No. 5,688,745, discloses salts of a sulfonylurea formed from bases, such as alkali metal carbonates, alkali metal hydroxides, alkaline earth metal hydroxides, ammonia, and ethanolamine, or acids, such as hydrochloric acid, nitric acid, trichloroacetic acid, acetic acid, and palmitic acid.
Schnabel et al., U.S. Pat. No. 5,696,053, is directed to a salt of a sulfonylurea containing a metal or ammonium ion.
Föry et al., PCT Publication No. WO 97/41112, discloses a salt of a sulfonylurea containing an alkali metal or alkaline earth metal atom.
SUMMARY OF THE INVENTION
Applicants have discovered quaternary ammonium salts of a sulfonylurea having high water solubility and high hydrolytic stability, and a method of preparing such compounds comprising contacting a quaternary ammonium hydroxide with a sulfonylurea to form the quaternary ammonium salt of a sulfonylurea.
Pesticidal, herbicidal, fungicidal, and plant growth regulating compositions comprising an effective amount of one or more of the quaternary ammonium salts of a sulfonylurea are a further embodiment of the present invention.
Still another embodiment is a method of controlling plants or fungi comprising applying an effective amount of one or more of the quaternary ammonium salts of a sulfonylurea of the present invention to the plants or fungi, the seeds of the plants, or the area on which the plants or fungi grow. Yet another embodiment is a method of regulating the growth of plants comprising applying an effective amount of one or more of the quaternary ammonium salts of a sulfonylurea of the present invention to the plants.
REFERENCES:
patent: 4479821 (1984-10-01), Meyer et al.
patent: 4681619 (1987-07-01), Meyer et al.
patent: 2073135 (1993-01-01), None
patent: 0 521 500 (1993-07-01), None
patent: 00/44226 (2000-08-01), None
Chen Chia-Chung
Tirol Arturo A.
Tseng Chuen-Ing
Wysong Robert D.
Balasubramanian Venkataraman
Darby & Darby
Lonza Inc.
Shah Mukund J.
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