Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-05-23
2003-05-06
Aulakh, Charanjit S. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S296000, C546S290000, C514S345000
Reexamination Certificate
active
06559170
ABSTRACT:
FIELD OF THE INVENTION
This invention is related to the field of compounds having fungicidal activity and processes to produce and use same.
BACKGROUND OF THE INVENTION
Our history is riddled with outbreaks of fungal diseases that have caused widespread human suffering. One need look no further than the Irish potato famine, which occurred from 1845 to 1860, where an estimated 1,000,000 people died, and an estimated 1,500,000 emigrated, to see the effects of a fungal disease.
Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield and the quality of the crop and consequently, increase the value of the crop. In most situations, the increase in value of the crop is worth at least three times the cost of the use of the fungicide. However, no one fungicide is useful in all situations. Consequently, research is being conducted to produce fungicides that are safer, that have better performance, that are easier to use, and that cost less.
In light of the above, the inventors provide this invention.
SUMMARY OF THE INVENTION
It is an object of this invention to provide compounds that have fungicidal activity.
It is an object of this invention to provide processes that produce compounds that have fungicidal activity.
It is an object of this invention to provide processes that use compounds that have fungicidal activity.
In accordance with this invention, processes to produce and processes to use compounds having a general formula according to formula one, and said compounds are provided.
While all the compounds of this invention have fungicidal activity, certain classes of compounds may be preferred for reasons such as, for example, greater efficacy, or ease of synthesis.
Throughout this document, all temperatures are given in degrees Celsius and all percentages are weight percentages, unless otherwise stated. The term “Me” refers to a methyl group. The term “Et” refers to an ethyl group. The term “Pr” refers to a propyl group. The term “ppm” refers to parts per million. The term, “psi” refers to pounds per square inch.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of this invention have a formula according to formula one.
In formula one:
A
1
, A
2
, A
3
, and A
4
are independently selected from the group consisting of hydro (—H), halo (—F, —Cl, —Br, and —I), and methyl (—CH
3
);
E is selected from the group consisting of aza (—N═) and methine (—CH═);
G is selected from the group consisting of oxo (O═) and thioxo (S═);
J is selected from the group consisting of oxy (—O—), amino (—NH—) and alkylamino (—NT
1
—) where T
1
is an alkyl group having 1 to 6 carbon atoms;
L
1
, L
2
, and L
3
are independently selected from the group consisting of hydro (—H), halo (—F, —Cl, —Br, and —I), cyano (—CN), methyl (—CH
3
), and mono, di, and trihalomethyl;
M is selected from the group consisting of thio (—S—), sulfinyl (—S(═O)—), and sulfonyl (—S(═O)
2
—); and
Q is selected from the group consisting of aryl (—Aryl), substituted aryl (—SAryl), heteroaryl (—HAryl), and substituted heteroaryl (—SHAryl), where “aryl” or “Ph” refers to a phenyl group and where “heteroaryl” refers to pyridyl, pyridinyl, pyrazinyl or pyridazinyl, and where said SAaryl and SHAryl have substituents that are independently selected from the group consisting C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halo-C
1
-C
6
alkyl, halo-C
1
-C
6
alkoxy, halo, nitro, carbo-C
1
-C
6
alkoxy, or cyano, arylalkyl, alkanoyl, benzoyl, amino, and substituted amino, preferably, hydro (—H), C
1
-C
6
alkyls, arylalkyl, alkanoyl, benzoyl, amino, and substituted amino where said substituted amino has substituents that are independently selected from the group consisting of hydro (—H), alkyl, arylalkyl, alkanoyl, benzoyl, and amino.
The term “alkyl”, “alkenyl”, or “alkynyl” refers to a unbranched or branched chain carbon group.
The term “alkoxy” refers to a unbranched or branched chain alkoxy group.
The term “haloalkyl” refers to a unbranched or branched alkyl group substituted with one or more halo atoms. The term “haloalkoxy” refers to an alkoxy group substituted with one or more halo atoms.
In general, these compounds can be produced by reacting a compound of formula two with a compound of formula three under suitable reaction conditions.
In formulas two and three, the variables are the same as in formula one and R is selected from the group consisting of halo (—F, —Cl, —Br, and —I), and alkylsulfonyl (—S(═O)
2
—T
2
) where T
2
is an alkyl group having from 1 to 6 carbon atoms.
In general, suitable reaction conditions include, the use of a strong base such as, for example, sodium hydride or potassium tert-butoxide, in a polar aprotic medium, such as, for example, tetrahydrofuran, diethylether, or dimethylsulfoxide, at temperatures that range from about 0 to about 100° C.
In general, these compounds can be used in a variety of ways. These compounds are preferably applied in the form of a formulation comprising one or more of the compounds with a phytologically-acceptable carrier. Concentrated formulations can be dispersed in water, or another liquid, for application, or formulations can be dust-like or granular, which can then be applied without further treatment. The formulations are prepared according to procedures which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of one or more of the compounds.
The formulations which are applied most often are aqueous suspensions or emulsions. Such water-soluble, water suspendable, or emulsifiable formulations are either solids, usually known as wettable powders, or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. The present invention contemplates all vehicles by which one or more of the compounds can be formulated for delivery and use as a fungicide.
As will be readily appreciated, any material to which these compounds can be added may be used, provided they yield the desired utility without significant interference with the activity of these compounds as antifungal agents.
Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of one or more of the compounds, an inert carrier and surfactants. The concentration of the compound in the wettable powder is usually from about 10% to about 90% w/w, more preferably about 25% to about 75% w/w. In the preparation of wettable powder formulations, the compounds can be compounded with any of the finely divided solids, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates or the like. In such operations, the finely divided carrier is ground or mixed with the compounds in a volatile organic solvent. Effective surfactants, comprising from about 0.5% to about 10% of the wettable powder, include sulfonated lignins, naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants, such as ethylene oxide adducts of alkyl phenols.
Emulsifiable concentrates of the compounds comprise a convenient concentration, such as from about 10% to about 50% w/w, in a suitable liquid. The compounds are dissolved in an inert carrier, which is either a water miscible solvent or a mixture of water-immiscible organic solvents, and emulsifiers. The concentrates may be diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions. Useful organic solvents include aromatics, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, such as, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-et
Carson Chrislyn Marie
Gajewski Robert Peter
Huang Zhengyu
Kirby Neil Vincent
Rieder Brent Jeffrey
Aulakh Charanjit S.
Corvin Carl D.
Dow AgroScience LLC
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