Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-04
2002-03-12
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S450000, C546S314000, C546S336000, C549S266000, C549S267000, C549S271000
Reexamination Certificate
active
06355660
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the field of fungicidal compositions and methods. More particularly, the present invention concerns novel fungicidal heterocyclic aromatic amides and methods involving application of fungicidally effective amounts of such compounds to the locus of a plant pathogen. The present invention also concerns methods useful in the preparation of heterocyclic aromatic amides and their fungicidal compositions.
2. Description of the Prior Art
A variety of antifungal compositions and methods are well known in the art. Antimycin, for example, has been identified as a naturally occurring substance produced by Streptomyces spp. with antibiotic properties (Barrow, C. J.; et al.,
Journal of Antibiotics
, 1997, 50(9), 729). These substances have also been found to be effective fungicides (
The Merck Index
, Twelfth Edition, S. Budavari, Ed., Merck and Co., Whitehouse Station, N.J., 1996, p. 120). WO 97/08135 describes acylaminosalicylic acid amides which are useful as pesticides. EP-A-0-661269 discloses substituted heterocyclic carboxylic acid amides useful as medical drugs. JP-A-7-233165 discloses antifungal dilactones having 3-hydroxypyridinecarboxyl groups with antimycotic action. The iso-butyryl, tigloyl, iso-valeryl and 2-methylbutyryl derivatives of these latter compounds are further described in the following references:
Tetrahedron
1998, 54, 12745-12774
; J. Antibiot
. 1997, 50(7), 551
; J. Antibiot
. 1996, 49(7), 639
; J. Antibiot
. 1996, 49(12), 1226; and
Tetrahedron Lett
. 1998, 39, 4363-4366.
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, curative activity, and a broader spectrum of efficacy.
SUMMARY OF THE INVENTION
Briefly describing one aspect of the present invention, there are provided compounds comprising heterocyclic aromatic amides (HAA) of the Formula I:
wherein X
1
-X
4
, M, Z, and A are hereafter defined. The invention also encompasses hydrates, salts and complexes thereof.
The present invention also provides fungicidal compositions comprising the HAA in combination with phytologically acceptable carriers and/or diluents. Methods for the use of the heterocyclic aromatic amide compounds and compositions are also disclosed.
It is an object of the present invention to provide HAA 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 fungal infestations, which methods include the application of HAA and compositions containing same.
Further objects and advantages of the present invention will be apparent from the description which follows.
GENERAL SCOPE OF THE INVENTION
The present invention relates to various HAA compounds which are active as antifungal agents. Also included are formulations including the HAA compounds, and methods of using the HAA compounds and formulations. The methods of preparing the HAA compounds are also encompassed by the present invention and their method of preparation and use as fungicides.
HAA Compounds
The novel antifungal HAA compounds of the present invention are described by the following Formula I:
wherein:
a.
represents a 5- or 6-membered heterocyclic aromatic ring in which
(i) each of X
1
-X
4
is independently O, S, NR′, N, CR″ or a bond;
(ii) no more than one of X
1
-X
4
is O, S or NR′;
(iii) no more than one of X
1
-X
4
is a bond;
(iv) when any one of X
1
-X
4
is S, O or NR′, one of the adjacent X
1
-X
4
must represent a bond; and
(v) at least one of X
1
-X
4
must be O, S, NR′ or N; wherein
R′ is H, C
1
-C
3
alkyl, C
2
-C
3
alkenyl, C
2
-C
3
alkynyl, hydroxy, acyloxy, C
1
-C
6
alkoxymethyl, CHF
2
, cyclopropyl or C
1
-C
4
alkoxy; and R″ is independently H, halogen, cyano, hydroxy, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, cyclopropyl, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, C
1
-C
3
alkylthio, aryl, C
1
-C
3
NHC(O)alkyl, NHC(O)H, C
1
-C
3
haloalkylthio, C
2
-C
4
alkenyl, C
2
-C
4
haloalkenyl, C
2
-C
4
alkynyl, C
2
-C
4
haloalkynyl or nitro wherein adjacent R″ substituents may form a ring or adjacent R′ and R″ substituents may form a ring;
b) Z is O, S or NOR
Z
in which R
Z
is H or C
1
-C
3
alkyl; and
c) A represents
(i) C
1
-C
14
alkyl, C
2
-C
14
alkenyl, or C
2
-C
14
alkynyl, all of which may be branched or unbranched, unsubstituted or substituted with halogen, hydroxy, nitro, aroyl, aryloxy, C
1
-C
8
acyloxy, C
1
-C
6
alkylthio, arylthio, aryl, heteroaryl, heteroarylthio, heteroaryloxy, C
1
-C
6
acyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy,
(ii) C
3
-C
14
cycloalkyl, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C
1
-C
6
alkylthio, arylthio, heteroarylthio, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
8
acyloxy, aryl, heteroaryl, C
1
-C
6
acyl, carboaryloxy, carboheteroaryloxy, C
1
-C
6
carboalkoxy or amido unsubstituted or substituted with one or two C
1
-C
6
alkyl groups,
(iii) C
6
-C
14
bi- or tricyclic ring system, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C
1
-C
6
alkylthio, arylthio, heteroarylthio, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
8
acyloxy, aryl, heteroaryl, C
1
-C
6
acyl, carboaryloxy, carboheteroaryloxy, C
1
-C
6
carboalkoxy or amido unsubstituted or substituted with one or two C
1
-C
6
alkyl groups,
(iv) aryl or heteroaryl, which may be unsubstituted or substituted with nitro, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
cycloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, aryl, heteroaryl, halogen, hydroxy, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, carboaryloxy, carboheteroaryloxy, C
1
-C
6
carboalkoxy or amido unsubstituted or substituted with one or two C
1
-C
6
alkyl groups, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkylsulfinyl, C
1
-C
6
OC(O)alkyl, OC(O)aryl, C
3
-C
6
OC(O)cycloalkyl, C
1
-C
6
NHC(O)alkyl, C
3
-C
6
NHC(O)cycloalkyl, NHC(O)aryl, NHC(O)heteroaryl, C
3
-C
6
cycloalkylthio, C
3
-C
6
cycloalkylsulfonyl, C
3
-C
6
cycloalkylsulfinyl, aryloxy, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, C(O)R
Y
, C(NOR
X
)R
Y
, in which any alkyl or cycloalkyl containing substituent may be substituted with one or more halogens and in which any aryl or heteroaryl containing substituent may also be unsubstituted or substituted with halogen, cyano, nitro, aroyl, aryloxy, aryl, heteroaryl, C
1
-C
6
acyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
carboalkoxy or amido unsubstituted or substituted with one or two C
1
-C
6
alkyl groups, where R
Y
and R
X
are independently H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
3
-C
6
cycloalkyl, aryl or heteroaryl, and
(v)
where *=point of attachment in which
Q
1
, Q
2
are O or S;
W is O, CH
2
, CHR
6
, or a bond;
R
1
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
3
-C
8
cycloalkyl, aryl or heteroaryl;
R
2
is H, C
1
-C
3
alkyl, C
2
-C
5
alkenyl or C
2
-C
5
alkynyl;
R
3
is H, R
1
, OR
1
, OC(O)R
1
, OC(o)OR
1
or OC(O)NR
1
R
6
;
R
4
and R
5
are independently H, C
1
-C
6
alkyl, or C
2
-C
6
alkenyl, provided that the sum of carbons for R
4
plus R
5
is six or less, and further provided that R
4
and R
5
may be joined into a C
3
-C
6
ring;
R
6
and R
7
are independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 alkenyl or C2-C5 alkynyl provided that at least one of R
6
and R
7
is H;
with the proviso that when
wherein
R″ is H or OCH
3
, then
R
1
is not isobutyryl, tigloyl, isovaleryl, or 2-methylbutanoyl;
d) M represents
H, Si(t-Bu)Me
2
, Si(Ph)Me
2
, SiEt
3
,
Adamski Butz Jenifer L.
Dent, III William H.
Fitzpatrick Gina M.
Gajewski Robert P.
Henry Matthew J.
Corvin Carl D.
Dow AgroSciences LLC
Patel Sudhaker B.
Raymond Richard L.
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