Fungicidally active carboxylic acid amides

Details Fungicidally active carboxylic acid amides Fungicidally active carboxylic acid amides

2001-02-20

2004-01-27

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S190000, C564S191000, C558S414000, C558S433000

Reexamination Certificate

active

06683212

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain fungicidal amides, their compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
Japanese Patent Application JP 2,233,654 and International Publication WO 97/35838 disclose certain amides and their use as fungicides. V. Prelog and J. Thix in
Helv. Chim. Acta
(1982), 65(8), 2622-44 disclose certain cyclobutane carboxamides.
The fungicidal amides of the present invention are not disclosed in these publications.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula I including all geometric and stereoisomers, agricultural compositions containing them and their use as fungicides:
wherein
R
1
is hydrogen; halogen; C
1
-C
2
alkoxy; C
1
-C
2
haloalkoxy; cyano; or C
1
-C
2
alkyl optionally substituted with halogen, C
1
-C
2
alkoxy or cyano;
R
2
is hydrogen; halogen; or C
1
-C
4
alkyl optionally substituted with halogen, C
1
-C
2
alkoxy or cyano;
R
3
is hydrogen; halogen; C
1
-C
4
alkoxy; C
1
-C
4
haloalkoxy; or C
1
-C
4
alkyl optionally substituted with halogen, C
1
-C
2
alkoxy or cyano; or
R
2
and R
3
can be taken together as —CH
1
CH
2
—;
R
4
is C
1
-C
2
alkyl;
R
5
is R
6
, CH(R
8
)OR
6
, CH(R
8
)CH(R
7
)R
6
or C(R
8
)═C(R
7
)R
6
;
R
6
is phenyl; naphthalenyl; a 5- to 6-membered aromatic heterocyclic ring containing 1 to 2 heteroatoms selected from nitrogen, oxygen and sulfur; or a 9- to 10-membered fused aromatic bicyclic ring containing 1 to 2 heteroatoms each R
6
optionally substituted with one to three substituents selected from the group halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, Si(CH
3
)
3
, cyano, NHC(═O)R
9
and NHC(═S)R
9
;
R
7
is halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
8
is hydrogen; C
1
-C
6
alkyl; phenyl optionally substituted with halogen, cyano, C
1
-C
3
alkyl or C
1
-C
3
alkoxy; or pyridinyl optionally substituted with halogen, cyano, C
1
-C
3
alkyl or C
1
-C
3
alkoxy; and
each R
9
is hydrogen or C
1
-C
4
alkyl;
provided that
i) at least one of R
1
, R
2
and R
3
is other than hydrogen; and
ii) when R
2
and R
3
are taken together as —CH
2
CH
2
—, then R
5
is other than R
6
.
DETAILS OF THE INVENTION
In the above recitations, the term “alkyl”, used alone or in the compound words such as “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers.
The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F
3
C, ClCH
2
, CF
3
CH
2
and CF
3
CCl
2
. The term “haloalkoxy” is defined analogously to the term “haloalkyl. Examples of “haloalkoxy” include CF
3
O, CCl
3
CH
2
O, HCF
2
CH
2
CH
2
O and CF
3
CH
2
O.
The terms “aromatic” is defined as those rings or rings which satisfy the Hüickel rule. The term “aromatic heterocyclic ring” includes aromatic heterocycles (where aromatic indicates that the Hückel rule is satisfied). The heterocyclic rings can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. Examples of 5- to 6-membered aromatic heterocyclic rings include thienyl, isothiazolyl, thiazolyl, pyrrolyl and pyridinyl. The term “fused aromatic bicyclic ring” includes fused aromatic heterocycles (where aromatic indicates that the Hückel rule is satisfied). Examples of fused aromatic bicyclic rings containing 1 to 2 heteroatoms include benzofuranyl, benzo[b]thiophenyl and benzothiazolyl.
The total number of carbon atoms in a substituent group is indicated by the “C
i
-C
j
” prefix where i and j are numbers from 1 to 4. For example, C
1
-C
2
alkyl designates methyl and ethyl.
When a group contains a substituent which can be hydrogen, for example R
1
or R
2
, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a group is optionally substituted with a substituent, (e.g., C
1
-C
2
alkyl optionally substituted with halogen), then, when the group is not substituted with that substituent, it is recognized that this is equivalent to said group having a hydrogen substituent.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Compounds of Formula I can exist as cis and trans cyclobutane isomers. This invention comprises cis/trans mixtures as well as the pure isomers. The compounds of this invention can exist as R and S enantiomers at the carbon to which R
4
and R
5
are attached. Of particular note are the compounds of Formula I having the R configuration. The R configuration is as defined by the Cahn-Ingold-Prelog system. (See March, J.
Advanced Organic Chemistry;
3rd ed., John Wiley: New York, (1985).) This invention comprises racemic mixtures as well as pure enantiomers. Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises all compounds selected from Formula I. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
Preferred compounds for reasons of better activity and/or ease of synthesis are:
Preferred 1. Compounds of Formula I above wherein
R
1
is halogen or C
1
-C
2
alkyl optionally substituted with halogen;
R
2
is halogen or C
1
-C
2
alkyl optionally substituted with halogen;
R
3
is halogen or C
1
-C
2
alkyl optionally substituted with halogen;
R
4
is CH
3
;
R
5
is R
6
; and
R
6
is phenyl optionally substituted with one to two substituents selected from the group halogen, C
1
-C
4
alkyl, CF
3
, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy and cyano.
Preferred 2. Most preferred compounds include compounds of Preferred 1 selected from the group
[1(R)-cis]-N-[1-(4-bromophenyl)ethyl]-3-chloro-3-methyl-1-(trifluoromethyl)cyclobutanecarboxamide;
[1(R)-trans]-N-[1-(4-bromophenyl)ethyl]-3-chloro-3-methyl-1-(trifluoromethyl)cyclobutanecarboxamide;
[1(R)-trans]-N-[1-(4-bromophenyl)ethyl]-3-chloro-3-methyl-1-(trifluoromethyl)cyclobutanecarboxamide;
[1(R)-trans]-3-chloro-N-[1-(4chlorophenyl)ethyl]-3-methyl-1-(trifluoromethyl)cyclobutanecarboxamide;
[1(R)trans]-3-chloro-N-[1-(2,4-dichlorophenyl)ethyl]-3-methyl-1-(trifluoromethyl)cyclobutanecarboxamide;
(1R)-N-[1-(4-bromophenyl)ethyl]-1,3,3-trichlorocyclobutanecarboxamide;
[1(R)-trans]-N-[1-(4-bromophenyl)ethyl]-3-chloro-1,3-dimethylcyclobutanecarboxamide;
[1(R)cis]-N-[1-(4-bromophenyl)ethyl]-3-chloro-1,3-dimethylcyclobutanecarboxamide;
[1(R)-trans]-3-bromo-N-[1-(4-bromophenyl)ethyl]-1,3-dimethylcyclobutanecarboxamide;
[1(R)-cis]-3-bromo-N-[1-(4-bromophenyl)ethyl]-1,3-dimethylcyclobutanecarboxamide;
[1(R)-trans]-3-chloro-N-[1-(2,4-dichlorophenyl)ethyl

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