Phenylcarbamates, their preparation, and compositions...

Details Phenylcarbamates, their preparation, and compositions... Phenylcarbamates, their preparation, and compositions...

1999-07-21

2001-05-15

Geist, Gary (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

N-c doai

C560S024000, C560S027000, C560S029000, C560S030000

Reexamination Certificate

active

06232339

ABSTRACT:

The present invention relates to phenylcarbamates of the formula I
where:
R
1
is C
1
-C
4
-alkyl;
R
2
is cyano, nitro, trifluoromethyl, halogen, C
1
-C
4
-alkyl and C
1
-C
4
-alkoxy;
m is 0, 1 or 2, where the radicals R
2
may be different if m is 2;
R
3
is hydrogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
3
-C
6
-cycloalkyl;
R
4
, R
6
independently of one another are each 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, where these radicals may be partially or fully halogenated or may 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
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, where the cyclic groups for their part may be partially or fully halogenated or may 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
-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
7
)—A
n
—R
8
;
aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals may be partially or fully halogenated or may 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
-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 or C(═NOR
7
)—A
n
—R
8
;
R
5
is hydrogen,
C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, where the hydrocarbon radicals of these groups may be partially or fully halogenated or may 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
-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, where the cyclic radicals for their part may be partially or fully halogenated and/or may 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
7
)—A
n
—R
8
;
C
3
-C
6
-CyCloalkyl, C
3
-C
6
-CyCloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may 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;
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
7
is hydrogen or C
1
-C
6
-alkyl and
R
8
is hydrogen or C
1
-C
6
-alkyl,
and salts thereof.
Furthermore, the invention relates to processes and intermediates for preparing these compounds and to compositions comprising them for controlling animal pests and harmful fungi.
Phenylcarbamates having a methoximino group in the ortho position are disclosed in WO-A 93/15046. &agr;-Phenylacrylic acid and &agr;-phenyl-&agr;-methoximinoacetic acid derivatives having a methoximino group in the ortho position are known from EP-A 426 460, EP-A 460 575, EP-A 472 300, EP-A 585 751, WO-A 92/13830, WO-A 92/18487, WO-A 92/18494, JP-A 05/201 946 and JP-A 05/255 012. The compounds described therein carry a CH
2
O—N═CR′R″ group in the position ortho to the group corresponding to the carbamate substituent.
WO-A 97/15552 discloses those &agr;-phenylacrylic acid and &agr;-phenyl-&agr;-methoximinoacetic acid derivatives in which the CH
2
O—N═CR′R″ group carries cyano, alkyl, haloalkyl and cycloalkyl, and bisoxime ether groups, as substituents R′ and R″, respectively.
The compounds described in the abovementioned applications are suitable for use as crop protection agents against harmful fungi and in some cases against animal pests.
It is an object of the present invention to provide novel compounds having improved activity.
We have found that this object is achieved by the phenylcarbamates I defined at the outset. Additionally, we have found processes and intermediates for their preparation, and compositions comprising them for controlling animal pests and harmful fungi, and their use to this end.
The compounds I can be obtained by various routes according to processes known per se from the literature.
In principle, when synthesizing the compounds I it is immaterial whether the carbamate group —N(OCH
3
)—COOR
1
or the group
is synthesized first.
The synthesis of the carbamate group —N(OCH
3
)—COOR
1
is known, for example, from WO-A 93/15046.
1. The compounds of the formula I are generally synthesized by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.
In the formula II, L
1
is a nucleophilically replaceable leaving group, for example halogen or a sulfonate group, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine, in accordance with the methods described in Houben-Weyl, Vol. E 14b, p. 370f. and Houben-Weyl, Vol. 10/1, p. 1189f.
The required hydroxyimines III are obtained, for example, as desc

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