Phenylacetic acid derivatives, preparation thereof and...

Details Phenylacetic acid derivatives, preparation thereof and... Phenylacetic acid derivatives, preparation thereof and...

2000-02-03

2001-02-13

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S542000, C514S599000, C514S616000, C514S618000, C514S620000, C514S622000, C558S414000, C560S018000, C560S035000, C564S074000, C564S153000, C564S154000, C564S156000, C564S157000, C564S158000, C564S162000, C564S164000, C564S165000

Reexamination Certificate

active

06187812

ABSTRACT:

The present invention relates to phenylacetic acid derivatives of the formula I
where the substituents and the index have the following meanings:
X is oxygen or sulfur;
R is hydrogen and or C
1
-C
4
-alkyl;
R
1
is hydrogen and or C
1
-C
4
-alkyl;
R
2
is cyano, nitro, trifluoromethyl, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy;
m is 0, 1 or 2, it being possible for the R
2
radicals to be different if m is 2;
R
3
is hydrogen, cyano, nitro, hydroxyl, amino, halogen,
C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylamino or di-C
1
-C
4
-alkylamino;
R
4
is 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 partly or completely halogenated or to carry one to three of the following radicals: 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
-alkoxycarbonlyl, 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
-cycloalkoxy, 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 partly or completely halogenated and/or to carry 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, 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
6
)—A
n
—R
7
;
C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, 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 partly or completely halogenated or to carry 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 and hetaryloxy;
R
5
is hydrogen, C
1
-C
10
-alkyl, C
3
-C
6
-cycloalkyl, 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 partly or completely halogenated or to carry 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
5
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry 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
-alkyl amino, C
1
-C
6
-alkyl aminocarbonyl, 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
6
)—A
n
—R
7
;
aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry 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
-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 or C(═NOR
6
)—A
n
—R
7
;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C
1
-C
6
-alkyl;
n is 0 or 1;
R
6
is hydrogen or C
1
-C
6
-alkyl and
R
7
is hydrogen or C
1
-C
6
-alkyl,
and their salts.
The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.
Phenylacetic acid derivatives for pest control are disclosed in the literature (EP-A 398 692, EP-A 477 631, EP-A 513 580, EP-A 567 828, EP-A 528 682, EP-A 463 488, WO-A 92113,830).
It is an object of the present invention to provide novel compounds having improved action.
We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use within this context.
The compounds I are obtainable in various ways by processes known per se in the literature.
Fundamentally, it is insignificant in the synthesis of the compounds I whether the group
⊖
C(NOCH
3
)—CONRR
1
or the group —CH
2
ON═C(R
3
)—C(R
4
)NOR
5
is constructed first.
The construction of the group —C(NOCH
3
)—CONRR
1
is disclosed, for example, in the literature cited at the outset.
The manner of the synthesis of the —CH
2
ON—C(R
3
)═C(R
4
)—NOR
3
side chain essentially depends on the nature of the substituents R
3
and R
4
.
1. In the case in which R
3
and R
4
are not halogen, the construction of the group —CH
2
ON═C(R
3
)—C(R
4
)—NOR
5
in general proceeds by reacting a benzyl deriv

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