Fungicidal carboxamides

Details Fungicidal carboxamides Fungicidal carboxamides

2001-03-02

2003-11-04

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S542000, C514S424000, C514S427000

Reexamination Certificate

active

06642392

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain N-(arylpropyl), N-(aryloxyethyl), and N-(arylallyl)-carboxamides, their agriculturally suitable salts and 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.
U.S. Pat. No. 4,710,518 discloses compounds of Formula i and compositions thereof as fungicides:
wherein
X is halogen;
n is 1 or 2;
R
1
is hydrogen, halogen or lower alkyl;
R
2
is lower alkyl, halogen-substituted lower alkyl or hydrogen; and
R
3
is hydrogen or lower alkyl.
U.S. Pat. No. 4,946,867 discloses compounds of Formula ii, and compositions and method of use thereof, as fungicides:
wherein
R is C
2
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl or C
3
-C
6
cycloalkyl; and
X is Cl, Br, CF
3
or lower fluoroalkoxy group.
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
X is —O—, —CH(R
11
)— or ═C(R
11
)—;
R
1
is H or C
1
-C
2
alkyl;
R
2
is H; C
1
-C
6
alkyl; C
3
-C
6
cycloalkyl; or phenyl optionally substituted with halogen, cyano, C
1
-C
2
alkyl or C
1
-C
2
alkoxy;
R
3
is H, C
1
-C
3
alkyl optionally substituted with halogen or CN;
R
4
is H or C
1
-C
2
alkyl; or
R
3
and R
4
can be taken together as —CH
2
CH
2
CH
2
— or —CH
2
CH
2
CH
2
CH
2
CH
2
—;
R
5
is H, C
1-C
2
alkyl optionally substituted with halogen or CN;
R
6
is C
2
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
2
-C
8
alkynylalkenyl or C
3
-C
8
cycloalkyl, each optionally substituted with halogen;
R
7
is H, CN, halogen, C
1
-C
2
haloalkoxy or C
1
-C
2
haloalkylthio; or C
1
-C
4
alkyl C
2
-C
4
alkenyl or C
2
-C
4
alkynyl, each optionally, substituted with halogen or CN;
R
8
, R
9
and R
10
are each independently H, halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, or Si(CH
3
)
3
; and
R
11
is H, C
1
-C
5
alkyl, C
2
-C
5
alkenyl or C
2
-C
5
alkynyl.
DETAILS OF THE INVENTION
In the above recitations, the term “alkyl”, used in compound words such as “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl or i-propyl. The term “alkyl”, used alone includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl, hexyl, heptyl or octyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl, hexenyl, heptenyl and octenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl, hexynyl, heptynyl and octynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. “Alkynylalkenyl” is a compound word and includes straight-chain or branched alkyne substituted on a straight-chain or branched alkene. Examples of“alkynylalkenyl” include H
2
C═CHC(CH
3
)(C≡CH) and HC≡CCH═CHC(CH
3
)
2
.
In the above recitations, the term “alkoxy”, used in compound words such as “haloalkoxy” or “haloalkylthio” includes methyl and ethyl. Examples of“haloalkoxy” include CF
3
CH
2
O, CF
3
O, CHF
2
CF
2
O, HF
2
CO and CCl
3
CCl
2
O. Examples of “haloalkyl ” include CF
3
S, HF
2
CS, CCl
3
S, CHF
2
CF
2
S and CF
3
CH
2
S.
The term “halogen”, either alone, when a group is “optionally substituted with halogen” or in compound words such as “haloalkyl”, “haloalkoxy” or “haloalkylthio”; includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” or when a group is “optionally substituted with halogen”, said alkyl or group 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
. Examples of an alkyl group “optionally substituted with halogen” include CH(F)═CHC(CH
3
)(CH
2
F) and CH
2
═CHC(CH
3
)(CH
2
F).
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 6. For example, C
1
-C
3
alkyl designates methyl through propyl. When a group contains a substituent which can be hydrogen, for example R
1
or R
3
, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers 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). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises 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.
Of note are compounds where R
7
is other than H, especially when Z is Z-1. Also of note are compounds where R
7
is hydrogen and R
8
is other than hydrogen and when Z is Z-1 is attached to the carbon adjacent to the R
7
substituted carbon. Further of note are compounds where the carbon attached to R
1
has the (R) configuration.
Also of note are compounds wherein R
1
is H or CH
3
; R
2
is H or CH
3
; R
6
is C
2
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl or C
3
-C
6
cycloalkyl each optionally substituted with halogen; and R
7
is H, CN, halogen, C
1
-C
4
haloalkyl, C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkynyl each optionally substituted with halogen or CN.
Compounds of the invention include compounds of Formula Ia, Ib and Ic.
Preferred compounds for reasons of better activity and/or ease of synthesis are:
Preferred 1. Compounds of Formula I above and agriculturally suitable salts thereof, wherein:
Q is Q-1;
R
1
is CH
3
;
R
2
is H;
R
3
is CH
2
CH
3
; and
R
4
is CH
3
.
Preferred 2. Compounds of Preferred 1 wherein:
Z is Z-1 or Z-4;
R
7
is H, halogen, CN, C
1
-C
4
alkyl or C
2
-C
4
alkenyl;
R
8
is H or F and is in the para position with respect to X when Z is Z-1; and
R
9
is in the para position with respect to R
7
when Z is Z-1.
Preferred 3. Compounds of Preferred 1 wherein:
Z is Z-2 or Z-3; and
R
7
is H, halogen; CN, C
1
-C
3
alkyl or C
2
-C
4
alkenyl.
Preferred 4. Compounds of Formula I above and agriculturally suitable salts thereof, wherein:
Q is Q-2;
R
1
is CH
3
;
R
2
is H or phenyl optionally substituted with halogen, cyano, C
1
-C
2
alkyl or C
1
-C
2
alkoxy; and
R
6
is C
2
-C
6
alkyl or C
2
-C
6
alkenyl each optionally substituted with halogen.
Preferred 5. Compounds of Preferred 4 wherein:
Z is Z-1 or Z-4;
R
7
is H, halogen, C
1
-C
3
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkynyl;
R
8
is H or F and is in the para position with respect to X when Z is Z-1; and
R
9
is in the para position with respect to R
7
when Z is Z-1.
Preferred 6. Compounds of Preferred 4 wherein:
Z is Z-2 or Z-3; and
R
7
is H, halogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkynyl.
This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a

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