Substituted 2-oxo-3-alkynoic acids and methods of use thereof

Details Substituted 2-oxo-3-alkynoic acids and methods of use thereof Substituted 2-oxo-3-alkynoic acids and methods of use thereof

1999-07-01

2001-03-20

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S313000, C504S314000, C504S320000, C504S321000, C504S325000

Reexamination Certificate

active

06204220

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the field of herbicides for use in agriculture. More specifically, the invention provides potent irreversible inhibitors of the pyruvate dehydrogenase multienzyme complex and methods of use therof.
BACKGROUND OF THE INVENTION
Several publications are referenced in this application by author name and year of publication in parentheses in order to more fully describe the state of the art to which this invention pertains. The disclosure of each of these publications is incorporated by reference herein.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds agronomically, in useful crops, including but not limited to cotton, rice, corn, wheat, and soybeans. Unchecked weed growth in such crops can cause significant losses, reducing profits to the farmer and increasing costs to the consumer.
In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for such purposes, but the search continues for products which are more effective, less costly, and environmentally safe.
SUMMARY OF THE INVENTION
In accordance with the present invention, argriculturally suitable compositions are provided which comprise certain 2-oxoalkynoic acids and derivatives thereof as well as methods of using such compositions as preemergence and/or post emergence herbicides. Representative compounds which are useful for practicing this invention are 2-oxo-3-butynoic acid, 2-oxo-3-pentynoic acid and 2-oxo-3 heptynoic acid. The synthetic scheme for synthesis of these compounds is provided in Example I.
In a preferred embodiment of the invention a herbicidal composition is provided which comprises a herbicidally effective amount of a compound having the formula:
wherein R represents H or the residue of a protecting group; R′ represents R″(CH
2
)
n
—, wherein R″ is selected from the group consisting of hydrogen or halogen, or R′ represents unsubstituted or substituted phenyl (C
6
H
5
), wherein the phenyl substituent is at least one selected from the group consisting of fluorine or trifluoromethyl; and n is an integer from 0-4, or an agriculturally suitable salt of the acid form of said compound, and a carrier medium is provided. In formula (I), R may be the residue of an ester protecting group which is cleavable by a plant esterase. Such an ester protecting group may be selected from the group consisting of a benzyloxymethyl ester and a methoxymethyl ester. Furthermore, R may be the residue of an ester protecting group that is photochemically cleavable. Representative of this type of protecting group is a phenyl-substituted phenyacyl ester. In another embodiment, R is the residue of a t-butyl ester protecting group.
The carrier medium comprises an inert liquid diluent and, optionally a surfactant. Preferably the liquid diluent is a solvent for the compound of formula I. Alternatively, the carrier medium may comprise an inert solid diluent.
The herbicidal composition of the invention may further comprise at least one additive selected from the group consisting of anti-foaming agents, anti-caking agents, anti-corrosive agents, anti-bacterial agents and anti-fungal agents. Finally the composition of the invention may include at least one additional herbicide selected from the group set forth in FIG.
7
.
In yet another aspect of the invention, a method for controlling the growth of undesired vegetation is provided. The method entails applying an herbicidally effective amount of the compositions of the invention to the site to be protected.


REFERENCES:
Devine et al. Physiology of Herbicide Action. Chapter 15, “Other Sites of Herbicide Action”. NJ: PTR Prentice Hall. p. 323-324, 1993.*
Brown et al. Biochemistry. 36(26):8071-8081. “2-Oxo-3-alkynoic Acids, Universal Mechanism-Based Inactivators of Thiamin Diphosphate-Dependent Decarboxylases: Synthesis and Evidence for Potent Inactivation of the Pyruvate Dehydrogenase Multienzyme Complex”, 1997.

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