Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2003-02-27
2004-05-11
Huang, Evelyn Mei (Department: 1625)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S251000, C504S252000, C504S253000, C504S248000, C504S236000, C504S239000, C504S244000, C544S063000, C544S096000, C544S228000, C544S333000, C546S271400, C546S272400, C546S274100, C546S275400, C546S276400, C546S194000, C546S269400, C514S340000, C514S336000, C514S341000, C514S343000, C514S348000, C514S228800
Reexamination Certificate
active
06734143
ABSTRACT:
FIELD OF THE INVENTION
This invention is related to the field of compounds having fungicidal activity and processes to make and use such compounds.
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 of the 1850's, where an estimated 1,000,000 people died, 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 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 make 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.
DETAILED DESCRIPTION OF THE INVENTION
The compounds have a formula according to formula one. In formula one:
A is selected from the group consisting of oxy (—O—) and amino (—NH—);
E is selected from the group consisting of aza (—N═) and methine (—CH═);
j
1
, j
2
, j
3
, and J
4
are independently selected from the group consisting of hydro (—H), halo (—F, —Cl, —Br, and —I), C
1-4
alkyl, C
1-4
alkoxy, C
14
alkyl (mono or multi-halo), and C
1-4
alkylthio;
M
1
, M
2
, and M
3
are selected from the group consisting of hydro (—H), halo (—F, —Cl, —Br, and —I), C
1-4
alkyl, Cl
4
alkoxy, C
1-4
alkyl (mono or multi-halo), and C
1-4
alkylthio, nitro (—NO
2
), (mono or multi-halo) C
1-4
alkoxy;
Q is selected from the group consisting of oxy (—O—), NX (where X is selected from the group consisting of hydro (—H) and C
1-4
alkyl, or X is the connecting bond to the pyridyl), and CZ
1
Z
2
(where each Z is independently selected from the group consisting of hydro (—H) and C
1-4
alkyl, or one Z is the connecting bond to the pyridyl);
R is selected from the group consisting of oxy (—O—), NX
1
(where X
1
is selected from the group consisting of hydro (—H) and C
1-4
alkyl, or X
1
is the connecting bond to the pyridyl), and CZ
3
Z
4
(where each Z is independently selected from the group consisting of hydro (—H) and C
1-4
alkyl, or one Z is the connecting bond to the pyridyl); and
T is a C
1-2
carbon atom chain connecting Q to R where each carbon atom in this chain is fully saturated. Consequently, each carbon atom in the chain in T has four other single bonds. T can be optionally substituted with a C
1-4
alkyl or one of the single bonds can be the connecting bond to the pyridyl.
The term “alkyl”, “alkenyl”, or “alkynyl” refers to an unbranched or branched chain carbon group. The term “alkoxy” refers to an unbranched or branched chain alkoxy group. The term “haloalkyl” refers to an 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. 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 “Bu” refers to a butyl group. The term “EtOAc” refers to ethyl acetate. The term “ppm” refers to parts per million. The term, “psi” refers to pounds per square inch.
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 that are applied most often are aqueous suspensions or emulsions. Either such water-soluble, water suspendable, or emulsifiable formulations are 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. Usefully 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-ethoxyethanol.
Emulsifiers which can be advantageously employed herein can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and f
Butz Jenifer Lynn Adamski
Cetusic Jeannie Rachel Phillips
Gustafson Gary David
Kirby Neil Vincent
Mathieson John Todd
Corvin Carl D.
Dow AgroSciences LLC
Huang Evelyn Mei
Zettler Lynn M.
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