Phenylacetic acid derivatives, process for their preparation...

Details Phenylacetic acid derivatives, process for their preparation... Phenylacetic acid derivatives, process for their preparation...

1998-02-24

2001-07-24

Wilson, James O. (Department: 1623)

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

Organic compounds

Amino nitrogen containing

C514S557000, C514S561000, C514S564000, C514S565000, C514S576000, C514S613000, C514S614000, C514S631000, C514S637000, C514S638000, C514S639000, C564S249000, C564S250000

Reexamination Certificate

active

06265613

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to phenylacetic acid derivatives of the formula I
where the substituents and the indexes have the following meanings:
X is NOCH
3
, CHOCH
3
and CHCH
3
;
Y is oxygen or NR
a
;
R
a
is hydrogen or C
1
-C
4
-alkyl;
R is cyano, nitro, trifluoromethyl, halogen, C
1
-C
4
-alkyl and C
1-C
4
-alkoxy;
m is 0, 1 or 2, it being possible for the radicals R to be different if m is 2;
R
1
is hydrogen or C
1
-C
6
-alkyl;
R
2
and R
3
independently of one another are
hydrogen, cyano, nitro, hydroxyl, amino, halogen,
C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkenylthio, C
2
-C
6
-alkenylamino, N—C
2
-C
6
-alkenyl-N—C
1
-C
6
-alkylamino, C
2
-C
6
-alkynyl, C
2
-C
6
-alkynyloxy, C
2
-C
6
-alkynylthio, C
2
-C
6
-alkynylamino, N—C
2
-C
6
-alkynyl-N—C
1
-C
6
-alkylamino, it being possible for the hydrocarbon radicals of these groups to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
2
-C
6
-alkenyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C
1
-C
4
-alkoxy, arylthio, aryl-C
1
-C
4
-alkylthio, hetaryl, hetaryloxy, hetaryl-C
1
-C
4
-alkoxy, hetarylthio, hetaryl-C
1
-C
4
-alkylthio, it being possible for the cyclic radicals, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
C
6
-cycloalkyl [sic], C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR
b
)—A
n
—R
c
;
C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-cycloalkylthio, C
3
-C
6
-cycloalkylamino, N—C
3
-C
6
-cycloalkyl-N—C
1
-C
6
-alkylamino, C
3
-C
6
-cycloalkenyl, C
3
-C
6
-cycloalkenyloxy, C
3
-C
6
-cycloalkenylthio, C
3
-C
6
-cycloalkenylamino, N—C
3
-C
6
-cycloalkenyl-N—C
1
-C
6
-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N—C
1
-C
6
-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N—C
1
-C
6
-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N—C
1
-C
6
-alkylamino, it being possible for the cyclic radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, C(═NOR
b
)—A
n
—R
c
or NR
f
—CO—D
n
—R
g
;
A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or C
1
-C
6
-alkyl;
D is oxygen or NR
h
;
n is 0 or 1;
R
b
, R
c
independently of one another are hydrogen or C
1
-C
6
-alkyl;
R
f
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
g
, R
h
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, aryl, aryl-C
1
-C
6
-alkyl, hetaryl and hetaryl-C
1
-C
6
-alkyl;
R
4
is one of the groups mentioned under R
2
or a group CR
d
═NOR
e
;
R
d
is one of the groups mentioned under R
2
;
R
e
is hydrogen,
C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
2
-C
10
-alkynyl, C
1
-C
10
-alkylcarbonyl, C
2
-C
10
-alkenylcarbonyl, C
3
-C
10
-alkynylcarbonyl or C
1
-C
10
-alkylsulfonyl, it being possible for these radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups, in turn, to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkyloxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR
b
)—A
n
—R
c
;
C
3
-C
6
-cycloalkyl, aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkyloxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, C(═NOR
b
)—A
n
—R
c
or NR
f
—CO—D—R
g
;
and to their salts.
The invention furthermore relates to processes for the preparation of these compounds and to compositions comprising them for controlling animal pests and harmful fungi.
The literature discloses phenylacetic acid derivatives for controlling animal pests and harmful fungi (WO-A 95/18,789, WOP-A 95/21,153, WO-A 95/21,154, WO-A 95/21,156).
However, it was an object of the present invention to provide compounds with an improved activity.
SUMMARY OF THE INVENTION
We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset.
We have furthermore found processes for their preparation, compositions comprising them for controlling animal pests and harmful fungi, and their use for this purpose.
DETAILED DESCRIPTION OF THE INVENTION
The compounds I are access

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