Use of phenylacetamides as plant protectives having...

Details Use of phenylacetamides as plant protectives having... Use of phenylacetamides as plant protectives having...

2001-08-21

2003-09-02

McKane, Joseph K. (Department: 1626)

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

Organic compounds

Nitriles

Reexamination Certificate

active

06613931

ABSTRACT:

The present invention relates to the use of phenylacetamides as crop protection agents, to novel crop protection compositions comprising, as active compounds, phenylacetamides, and to novel phenylacetamides.
The present invention provides the use of phenylacetamides of the formula I
as crop protection agents, where the radicals have the following meanings:
A is aryl which can be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-cyanoalkyl, C
2
-C
6
-alkyenyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
3
-C
6
-alkynyl-C
1
-C
6
-alkoxy, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkoxy-C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-cyanocycloalkoxy, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkoxy, C
3
-C
7
-halocycloalkyl, C
3
-C
7
-cyanocycloalkyl, C
3
-C
7
-halocycloalkoxy, C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkyl-C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkoxy-
5
-C
7
-cycloalkenyl, C
5
-C
7
-cyanocycloalkenyl, C
5
-C
7
-halocycloalkenyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, C
2
-C
6
-cyanoalkenyl, C
3
-C
6
-cyanoalkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-cyanoalkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-cyanoalkenyloxy, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-cyanoalkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarboxyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C
1
-C
6
-alkyl, aryl-C
2
-C
6
-alkenyl, aryl-C
3
-C
6
-alkynyl, aryl-C
1
-C
6
-alkoxy, aryl-C
2
-C
6
-alkenyloky, aryl-C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, aryl, aryloxy, arylthio or —C(R
4
)═NR
5
,
R
1
is aryl or aryl-C
1
-C
6
-alkyl, where the aryl radical can in each case be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy- C
1
-C
6
-alkyl, C
1
-C
6
-cyanoalkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy- C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
C
6
-alkoxy- C
3
-C
6
-alkynyl, C
3
-C
6
-alkynyl-C
1
C
6
-alkoxy, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkoxy- C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-cyanocycloalkoxy, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkoxy, C
3
-C
7
-halocycloalkyl, C
3
-C
7
-cyanocycloalkyl, C
3
-C
7
-halocycloalkoxy, C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkyl- C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkoxy- C
5
-C
7
-cycloalkenyl, C
5
-C
7
-cyanocycloalkenyl, C
5
-C
7
-halocycloalkenyl, C
1
-C
6
-haloalkyl, C
2
C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, C
2
-C
6
-cyanoalkenyl, C
3
-C
6
-cyanoalkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-cyanoalkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-cyanoalkenyloxy, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-alkynyloxy, C
-C
6
-alkylthio, C
1
-C
6
-cyanoalkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarboxyl- C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl- C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C
1
-C
6
-alkyl, aryl-C
2
-C
6
-alkenyl, aryl-C
3
-C
6
-alkynyl, aryl-C
1
-C
6
-alkoxy, aryl-C
2
-C
6
-alkenyloxy, aryl-C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, aryl, aryloxy, arylthio or —C(R
4
)═NR
5
,
R
2
, R
3
are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkylaryl, which may be unsubstituted or partially or fully halogenated or may carry one to three substituents selected from the group consisting of C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
C
4
-alkylthio, C
3
-C
7
-cycloalkyl, C
5
-C
7
-cycloalkenyl;
R
4
is hydrogen or C
1
-C
6
-alkyl,
R
5
is hydroxyl, C
1
-C
4
-alkoxy, aryl- C
1
-C
4
-alkoxy, aryloxy,
and their agriculturally useful salts.
Some of the compounds of the formula I are known from the literature.
WO 95/35283 describes trisubstituted phenyl derivatives as medicaments which act as PDE IV (phosphodiesterase IV) inhibitors. It describes in particular compounds of the following formula
where W is, inter alia, the group ═C(Y)—, where Y=halogen, alkyl, —X—R
a
or —N(R
b
), where X=O, S, SO, SO
2
; R
a
=hydrogen, alkyl; R
b
=hydrogen or alkyl; L=—CH(R
1
) (R
2
) where R
1
and R
2
=CN or —CONR
9
R
10
and R
9
and R
10
=hydrogen, alkyl, aralkyl or aryl; Z=one of the groups (A)-(D), described in more detail therein, where these groups have to be substituted by at least one aryl group (Ar).
EP 0 466 640 describes alpha-carbonylphenylacetonitrile derivatives as stabilizers for organic materials. The compounds of the formula
which are disclosed in that publication are suitable for stabilizing lubricating oils, fluids for processing metals, hydraulic fluids and thermoplastic polymers and elastomers. In the formula shown above, A is, inter alia, the group —NR
6
R
7
, where R
6
, R
7
may, inter alia, be hydrogen and unsubstituted phenyl or naphthyl. Two radicals R, R
1
, R
2
, R
3
or R
4
which are attached ortho to one another may also form the group —CH═CH—CH═CH—(naphthyl group).
DD 156,663 describes compounds of the formula below for use as plant growth stimulating agents for use in crop plants, such as, for example, maize, sunflower, tomato, soybean or beans:
The radicals have, inter alia, the following meanings: R
1
, R
2
: hydrogen, alkyl, cycloalkyl, aryl, haloaryl, aralkyl, alkenyl or alkanoyl; R
3
: hydrogen or alkyl. The compounds described are characterized by the fact that the phenyl group is in each case unsubstituted.
DE 2 008 692 describes cyanophenylacetamide derivatives of the formula below
as starting materials or intermediates for preparing indole-3-carboxylic acid derivatives. R
1
and R
2
are hydrogen, alkyl or aralkyl. The two radicals X and Y on the phenyl ring are, inter alia, hydrogen, halogen, alkyl, alkoxy, aralkoxy, trifluoromethyl, hydroxyl, amino, nitro, carboxyl or sulfoxy. Additionally, the phenyl ring may be substituted by an amino or nitro group.
Furthermore, the following individual compounds of the formula I are known from the scientific literature:
a) The compound where A=phenyl, R
1
=4-ethoxyphenyl, R
2
=H, R
3
=n-C
4
H
9
[N-(4-ethoxyphenyl)-2-cyano-2-phenylhexanamide] from Arch. Pharm. 321 (1988): 107.
b) The compound where A=phenyl, R
1
=4-ethoxyphenyl, R
2
=H, R
3
=C
2
H
5
; [N-(4-ethoxyphenyl)-2-cyano-2-phenylbutanamide from Arch. Pharm. 321 (1988), 739.
c) The compound where A=phenyl, R
1
=2,4,6-trimethoxyphenyl, R
2
=H, R
3
=H; [N-(2,4,6-trimethoxyphenyl)-2-cyano-2-phenylacetamide] from J. Med. Chem. 39,20 (1996), 3908.
d) The compound where A=4-methoxyphenyl, R
1
=2,6-dimethylphenyl, R
2
=H, R
3
=H; [N-(2,6,-dimethylphenyl)-2-cyano-2-phenylacetamide] from Liebigs Ann. Chem. 3, (1992): 239.
e) The compounds where A=phenyl, R
1
=2-methylphenyl, 3-methylphenyl or 4-methylphenyl, R
2
=H, R
3
=H; [N-(2-methylphenyl)-2-cyano-2-phenylacetamide; N-(3-methylphenyl)-2-cyano-2-phenylacetamide; N-(4-methylphenyl)-2-cyano-2-phenylacetamide] from Am. Chem. J. 39 (1908), 76.
Surprisingly, it has been found that compounds of the formula I can be used as crop protection agents having fungicidal and/or herbicidal action. They are suitable for treating plants, for example for controlling harmful fungi in useful plants (fungicidal a

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