Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-05-01
2001-12-25
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C514S535000, C514S496000, C514S616000, C560S043000, C564S048000
Reexamination Certificate
active
06333432
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the field of fungicidal compounds, compositions and methods, and more particularly to plant fungicides and methods involving the application of fungicidally effective amounts of such compounds and compositions to the locus of a plant pathogen. The present invention also provides novel compounds and methods useful in the preparation of fungicides and fungicidal compositions.
2. Description of the Prior Art
Varieties of antifungal compositions and methods are well known in the art. Antimycin, for example, has been identified as a naturally occurring substance produced by Streptomnyces spp which has efficacy as a fungicide. However, there has remained a need for new fungicides. The present invention provides fungicides which have a high residual activity, greater activity at lower application rates, and a broader spectrum of efficacy.
SUMMARY OF THE INVENTION
Briefly describing one aspect of the present invention, there are provided fungicidal compounds comprising acylated aminosalicylamides of the Formula I:
wherein m, n, q, X, Z, R
q
and R
1
-R
5
are as hereafter defined. The invention also encompasses hydrates, salts and complexes thereof.
The present invention also provides fungicidal compositions comprising the acylated aminosalicylamides in combination with phytologically acceptable carriers and/or diluents. Methods for the use of the acylated aminosalicylamides compounds and compositions are also disclosed.
In another aspect, the present invention includes compounds and methods for preparation of the acylated aminosalicylamides. Encompassed are certain novel intermediates, including ones having fungicidal efficacy, as well as methods for the preparation thereof.
It is an object of the present invention to provide acylated aminosalicylamides and compositions thereof which are effective as antifungal agents.
Another object of the present invention is to provide methods for the control and/or prevention of fungus infestations, which methods include the application of acylated aminosalicylamides and compositions containing same.
The present invention also has as an object the provision of certain intermediates, their methods of preparation and use in producing acylated aminosalicylamides, and optionally the use of such intermediates as fungicides.
Further objects and advantages of the present invention will be apparent from the description which follows.
DESCRIPTION OF THE PREFERRED EMBODIMENT
For the purposes of promoting an understanding of the principles of the invention, reference will now be made to the embodiments illustrated herein and specific language will be used to describe the same. It will nevertheless be understood that alterations, modifications and further applications of the invention are contemplated as would normally occur to one skilled in the art to which the invention relates. The present invention particularly contemplates such compounds, compositions and methods which are substantially equivalent to the inventions claimed herein.
General Scope of the Invention
The present invention relates to various acylated aminosalicylamide (“AASA”) compounds which are active as antifungal agents. Also included are formulations including the acylated aminosalicylamide compounds, and methods of using the AASA compounds and formulations. The methods of preparing the AASA compounds are also encompassed by the present invention, as well as certain intermediate compounds, and their method of preparation and optional use as fungicides.
Acylated Aminosalicylamide Compounds
The novel antifungal AASA compounds of the present invention are described by the following Formula I:
wherein:
a. m is 1 or 2;
b. ( )n represents a carbon chain including carbon atoms where n is 1 to 11;
c. q is from 0 to 2n;
d. X is hydrogen (“H”), halogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, cyclopropyl, cyano, NO
2
, C
1
-C
4
haloalkyl, hydroxy, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, C
1
-C
3
alkylsulfonyl, C
1
-C
3
alkylsulfinyl, C
1
-C
2
SCOalkyl, C
1
-C
3
NHalkyl, C
1
-C
3
N(alkyl)
2
, C
1
-C
3
NHCOalkyl, NHC(O)H, C
1
-C
3
N-alkyl COalkyl, C
1
-C
3
NHCONHalkyl, C
1
-C
2
NHCON(alkyl)
2
, NHC(O)R
x
, C(O)R
x
, C(O)OR
x
, or C(O)NR
x
R
x
, in which R
x
is independently H or C
1
-C
4
alkyl;
e. Z is H, C
1
-C
2
alkyl, CH
3
NH or Me
2
N;
f. R
1
and R
2
may be the same or different, but at least one of R
1
and R
2
must be H or methyl, and each of R
1
and R
2
is independently selected from the group consisting of H, cyano, C
1
-C
4
alkyl (straight chain or branched), C
2
-C
4
alkenyl (straight chain or branched), aryl, C
1
-C
4
haloalkyl (straight chain or branched), C
1
-C
4
carboalkoxy, and C
3
-C
6
cycloalkyl optionally substituted with one or more of OR
6
, SR
6
, NR
6
R
7
, halogen or cyano;
g. R
3
, R
4
, and R
5
may be the same or different and each of R
3
-R
5
is independently selected from the group consisting of H, halogen, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, C
3
-C
6
cycloalkoxy, aryloxy, C(═O)R
6
and C(═O)OR
6
;
h. each R
q
can be the same or different and each R
q
is defined as follows:
i. any or all of R
q
are H, halogen, cyano, C
1
-C
4
alkyl (straight chain or branched), C
2
-C
4
alkenyl (straight chain or branched), aryl, C
1
-C
4
haloalkyl (straight chain or branched), C
1
-C
4
alkoxy (straight chain or branched), C
1
-C
4
haloalkoxy (straight chain or branched), or C
1
-C
4
carboalkoxy, and C
3
-C
6
cycloalkyl optionally substituted with one or more of OR
6
, SR
6
, NR
6
R
7
, halogen or cyano;
ii. any of R
q
can be hydroxy provided that no two geminal R
q
are both hydroxy;
iii. any adjacent R
q
can be combined as unsaturations in the main chain to form alkenyl or alkynyl bonds as allowed by chemical bonding rules; and
iv. any of geminal R
q
can be combined in a double bond to an oxygen;
i. the number of substituents included as R
q
will vary depending on n and q in accordance with chemical bonding rules;
j. R
6
and R
7
may be the same or different and each of R
6
and R
7
is selected from the group consisting of H, C
1
-C
4
alkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
3
-C
6
cycloalkyl, aryl and C
1
-C
4
alkoxyalkyl, except that R
7
can not be H;
k. aryl, as used herein, may be unsubstituted or may have up to three substituents selected from the group consisting of halogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
3
-C
6
cycloalkyl, cyano, C
1
-C
4
haloalkyl, hydroxy, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy and aryloxy; and
l. when stereocenters are formed by various substitution patterns as described herein, all isomers are included in the definitions for the structure of Formula I.
The terms alkyl, alkylene, alkenylene and the like, as used herein, include within their scope both straight and branched groups, and the terms alkenyl, alkenylene and the like are intended to include groups containing one or more double bonds. The foregoing terms further contemplate either substituted or unsubstituted forms. A substituted form refers to substitution with one or more groups selected from halo, haloalkoxy, phenyl, alkoxy, carboalkoxy or amido, substituted with one or two alkyl groups.
The terms halogen and halo as used herein include chlorine, bromine, fluorine and iodine. The terms haloalkyl and the like refer to groups substituted with one or more halo atoms. It will be appreciated that certain combinations of substituent groups for compounds which fall within the definitions given herein will be impossible to prepare for steric and/or other chemical reasons. Such compounds are not included within the scope of the invention.
Various hydrates, salts and complexes of compounds of Formula I can be made in the conventional ways. For example, salts may be formed by replacing the hydroxyl hydrogen atom with a cation, for example, NH
4
+
,
+
N(CH
3
)
4
,
+
N(Bu)
4
, K
+
, Na
+
, Ca
++
, Li
+
, Mg
2+
, Fe
2+
, Cu
2+
, etc. These derivatives are also useful in accorda
Davis George E.
Fitzpatrick Gina M.
Orth Ann B.
Rogers Richard B.
Werk Todd L.
Corvin Carl D.
Kumar Shailendra
Loertscher Kenneth L.
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