Fungicidal compositions and methods of making thereof

Details Fungicidal compositions and methods of making thereof Fungicidal compositions and methods of making thereof

2000-07-05

2001-09-18

Owens, Amelia (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S471000, C514S473000, C514S423000, C514S424000, C548S406000, C548S452000, C548S537000, C549S004000, C549S052000, C549S055000, C549S062000, C549S214000, C549S434000, C549S450000

Reexamination Certificate

active

06291513

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to certain novel substituted heterocyclic compounds, methods for synthesizing novel substituted heterocyclic compounds, a method for the control of Take-All disease in plants, particularly cereals, by the use of the compounds, and fungicidal compositions for controlling Take-All disease.
BACKGROUND OF THE INVENTION
Take-All disease is a serious problem in the production of cereals, particularly wheat and barley. It is caused by the soil-borne fungus
Gaeumannomyces graminis
(
Gg
). The fungus infects the roots of the plant, and grows throughout the root tissue, causing a black rot. The growth of the fungus in the roots and lower stems prevents the plant from obtaining sufficient water and/or nutrients from the soil, and is manifested as poor plant vigor and, in severe instances of disease, by the formation of “whiteheads,” which are barren or contain few, shriveled grains. Yield loss results. Gaeumannomyces species also infect other cereal crops, for example, rice and oats; and turf.
Currently the primary means of avoiding crop loss due to infestation of the soil by
Gg
has been to rotate the crop grown to one which is resistant
Gg
. However, in areas where the primary crops are cereals, rotation is not a desirable practice, and an effective control agent is greatly desired.
U.S. Pat. No. 5,486,621, hereby incorporated by reference, discloses a unique fungicidal composition, 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxarnide, which provides superior and unexpected control of Take-All disease. It is an object of this invention to provide novel methods for synthesizing this unique fungicide. In addition, International Application No. PCT/US92/08633 discloses a broad scope of compounds effective against Take-All disease. Objects of the present invention also include providing additional novel compounds which will control the growth of
Gg
in the soil to reduce crop loss and providing novel methods for preparing such compounds. Further objects of this invention include providing an effective method for control of Take-All disease in plants and fungicidal compositions that may be used for control of Take-All disease as a seed treatment or as a soil treatment.
These and other objects of the invention will be apparent to those skilled in this art from the following description of the invention.
SUMMARY OF THE INVENTION
The fungicidal compound 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide, claimed in U.S. Pat. No. 5,486,621, Formula (I):
has shown superior and unexpected control of the growth of the soil-borne fungus
Gaeumannomyces graminis
(
Gg
). The present invention provides a novel method for synthesizing this fungicidal compound which uses the compound 4-hydroxy4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide, Formula (II):
In addition, the compound of Formula (II) has unexpectedly been found to provide control of Take-All disease. Therefore, the compounds of Formula (D) are expected to provide such control as well. The structure of Formula (III) is:
or an agronomic salt thereof; wherein:
Q is —NH, S, or O;
W is O, or S;
X is —OH, —OAc, —OR, where R is lower alkyl;
Y is S, O, or —NH;
Z is —Si(R)
3
, —C(R)
3
, where R is lower alkyl;
R
1
is a lower alkyl, allyl, or propargyl;
R
2
is a lower alkyl or aryl; and
R
3
and R4 are independently chosen from hydrogen, a lower alkyl and aryl;
optionally, R
2
and R
3
together form a 5- or 6-membered ring.
As used herein, the term “alkyl,” unless otherwise indicated, means an alkyl radical, straight or branched chain, having, unless otherwise indicated, from 1 to 10 carbon atoms.
As used herein, the term “aryl,” unless otherwise indicated, means a phenyl substituted with alkyl, alkoxy, halogen, nitro or cyano.
The invention also provides methods for using and for synthesizing the fungicidal compound of Formulas (I)-(III), methods for controlling
Gg
comprising applying a fungicidally effective amount of the compound of Formulas (I)-(III), and fungicidal compositions for use in controlling
Gg.
DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS
Control of
Gg
diseases, including Take-All, using a chemical control agent may be accomplished in several ways. The agent may be applied directly to soil invested with
Gg
, for example, at the time of planting along with the seed. Alternatively, it may applied after planting and germination. Compositions for soil application include clay granules which may be applied in-furrow, as broadcast granules or as impregnated fertilizer granules. In addition, the agent may be applied to the soil as a preemergent or postemergent spray. Preferably, however, it is applied to the seed in a coating prior to planting. This technique is commonly used in may crops to provide fungicides for control of various phytopathological fungi.
Compositions of the present invention may comprise a fungicidally effective amount of one or more of the compounds described above and one or more adjuvants. The active ingredient may be present in such compositions at levels from about 0.01 to about 95 percent by weight. Other fungicides may also be included to provide a broader spectrum of fungal control or to enhance the control of Take-All disease provided by the compounds of the present invention. The choice of fungicides will depend on the crop and the diseases known to be a threat to that crop in the location of interest.
The fungicidal compositions of this invention, including concentrates which require dilution prior to application, may contain at least one active ingredient and an adjuvant in liquid or solid form. The compositions may be prepared by admixing the active ingredient with an adjuvant including diluents, extenders, agronomically acceptable carriers, and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, solutions, dispersions or emulsions. Thus, it is believed that the active ingredient could be used with an adjuvant such as a finely-divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any suitable combination of these.
Suitable wetting agents are believed to include alkyl benzene and alkyl naphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (particularly isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the mono-higher fatty acid esters of hexitol anhydrides (e.g., sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnaphthalene sulfonate and neutralized polyoxyethylated derivatives or ring-substituted alkyl phenol phosphates. Stabilizers may also be used to produce stable emulsions, such as magnesium aluminum silicate and xanthan gum.
Other formulations may include dust concentrates comprising from about 0.1 to about 60% by weight of the active ingredient on a suitable extender, optionally including other adjuvants to improve handling properties, e.g., graphite. These dusts may be diluted for application at concentrations within the range of from about 0.1 to about 10% by weight.
Concentrates may also be aqueous emulsions, prepared by stirring a nonaqueous solution of a water-insoluble active ingredient and an emulsification agent with water until uniform and then homogenizing to give stable emulsion of very finely-divided particles. Or they may be aqueous suspensions, prepared by milling a mixture of a water-insoluble active ingredient and wetting agents to give a suspension, characterized by its extremely small particle size, so that when diluted, coverage is very uniform. It is believed suitable concentrations of these formulations contain from about 0.1 to about 60%

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