Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1998-04-23
2003-01-21
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C558S405000, C564S074000, C564S162000, C564S163000, C564S164000, C564S165000, C564S166000, C564S167000, C564S256000, C514S347000, C514S348000, C514S351000, C514S365000, C514S374000, C514S376000, C514S423000, C514S448000, C514S466000, C514S539000, C514S523000, C514S599000, C514S621000, C546S296000, C546S298000, C548S200000, C548S236000, C548S561000, C549S072000, C549S441000, C560S035000
Reexamination Certificate
active
06509379
ABSTRACT:
The present invention relates to phenylacetic acid derivatives of the formula I
where the variables have the following meanings:
X is NOCH
3
, CHOCH
3
or CHCH
3
;
Y is O or NZ, Z being hydrogen or C
1
-C
4
-alkyl;
R
1
is hydrogen 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 radicals R
2
to be different if m is 2;
R
3
is hydrogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or cyclopropyl;
R
4
is C
1
-C
4
-alkylenedioxy, the alkylene groups being partially or fully halogenated, or is one of the radicals:
—(C═O)—R
a
,
—C(═NOR
a
)—A
p
—R
b
,
—NR
c
—(C═O)—A
p
—R
a
,
—O—(C═O)—NR
a
R
b
or
—N(R
c
)—OR
d
, where
R
a
, R
b
independently of one another are hydrogen or in each case unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or hetaryl,
R
c
, R
d
independently of one another are hydrogen or in each case unsubstituted or substituted alkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyl, cycloalkylcarbonyl, cycloalkyloxycarbonyl, arylcarbonyl or hetarylcarbonyl,
p is 0 or 1 and
A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or C
1
-C
6
-alkyl;
n is 1 or 2, it being possible for the radicals R
4
to be different if n is 2;
R
5
is hydrogen,
C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, it being possible for these radicals 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
-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, arylthio, hetaryl, hetaryloxy, hetarylthio, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following substituents: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, 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, arylthio, hetaryl, hetaryloxy, hetarylthio and C
3
-C
6
-alkynyloxy;
C
3
-C
6
-cycloalkyl, which can be partially or fully halogenated and/or, independently of each other, can have attached to it one to three of the following groups: cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkylthio,
and to salts thereof.
Moreover, the invention relates to processes and intermediates for the preparation of these compounds and to their use for controlling animal pests and harmful fungi.
Phenylacetic acid derivatives for pest control have been disclosed in the literature (cf. WO-A 95/18789, WO-A 95/21153, WO-A 95/21154), but they are not yet satisfactory with a view to their activity.
It is an object of the present invention to provide novel compounds of this type which have an improved activity.
We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. Moreover, we have found processes and intermediates for their preparation, compositions comprising them for controlling animal pests and harmful fungi, and their use for these purposes.
The compounds I are accessible via various routes by processes known per se.
When synthesizing the compounds I, it is, in principle, irrelevant whether the group —C(X)—CO—Y—R
1
or the group
is first synthesized.
The synthesis of the group —C(X)—CO—Y—R
1
is disclosed, for example, in the publications cited at the outset and in the following: EP-A 242 070, EP-A 254 426, EP-A 370 629, EP-A 398 692, EP-A 422 597, EP-A 463 488, EP-A 472 300, EP-A 513 580, EP-A 656 352, German Application P 44 20 416.7.
When synthesizing the group
a procedure is generally followed in which a benzyl derivative of the formula II is reacted with a hydroxyimine of the formula III.
L
1
in formula II is a nucleophilically exchangeable leaving group, eg. halogen or sulfonate groups, 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, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine, following the methods described in Houben-Weyl, 4th Edition, Vol. E 14b, p. 370 et seq. and ibd. Vol. 10/1, p. 1189 et seq.
The hydroxyimine III which is required is obtained, for example, by reacting a corresponding dihydroxyimine IV with the compound of the formula VI
L
2
in formula VI is a nucleophilically exchangeable leaving group, eg. halogen or sulfonate groups, 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, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine as described in: Houben-Weyl, 4th Edition, Vol. E 14b, p. 307 et seq., p. 370 et seq. and p. 385 et seq.; ibid., 4th Edition, Vol. 10/4, p. 55 et seq., p. 180 et seq. and p. 217 et seq.; ibid., 4th Edition, Vol. E 5, p. 780 et seq.
Those compounds of the formula IV which are not already known can be prepared by methods known per se (cf. Gazz. Chim. Ital. 59 (1929), 719; Collect. Bull. Soc. Chim. Fr. 17 (1897), 71).
Alternatively, the compounds I can also be obtained by reacting the benzyl derivative II first with the dihydroxyimino derivative IV to give a corresponding benzyl oxime of the formula V, V subsequently being reacted with a compound of a [sic] formula VI to give I.
The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine following the methods described in Houben-weyl, 4th Edition, Vol. 10/1, p. 1189 et seq., Vol. E 14b, p. 307 et seq., p. 370 et seq. and p. 385 et seq., Vol. 10/4, p. 55 et seq., p. 180 et seq. and p. 217 et seq., Vol. E 5, p. 780 et seq.
Similarly, it is also possible to prepare the hydroxyimine [sic] of the formula III which is required from a carbonylhydroxyimine VII by reacting the latter with a hydroxylamine IXa or a salt thereof IXb.
Q
⊖
in formula IXb is the anion of an acid, in particular of an inorganic acid, eg. halide, such as chloride.
The reaction is carried out in a manner known per se in an inert organic solvent following the methods described in EP-A 513 580; Houben-Weyl, 4th Edition, Vol. 10/4, p. 73 et seq., Vol. E 14b, p. 369 et seq. and p. 385 et seq.
Those compounds of the formula VII which are not already known can be prepared by methods known per se (J. Am. Pharm. Assoc. 35 (1946), 15).
Alternatively, the compounds I can also be obtained by reacting the benzyl derivative II first with the carbonylhydroxyimino derivative VII to give a corresponding benzyloxyimine of the formula VIII, VIII subsequently being reacted with the hydroxylamine IXa or the salt thereof IXb to give I.
The reaction is carried out in a manner known per se in an inert organic solvent following the methods described in Houben-Weyl, 4th Edition, Vol. E 14b, p. 369 et seq., Vol. 10/1, p. 1189 et seq. and Vol. 10/4, p. 73 et s
Ammermann Eberhard
Bayer Herbert
Götz Norbert
Grammenos Wassilios
Grote Thomas
BASF - Aktiengesellschaft
Keil & Weinkauf
O'Sullivan Peter
LandOfFree
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