Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2002-01-16
2003-04-08
Gerstl, Robert (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S263000, C504S265000, C504S267000, C504S270000, C548S129000, C548S132000, C548S137000, C548S165000, C548S182000, C548S183000, C548S186000, C548S187000, C548S221000, C548S229000
Reexamination Certificate
active
06544931
ABSTRACT:
FIELD OF THE INVENTION
This application is a 371 of PCT/EP00/06461 filed Jul. 7, 2000.
The invention relates to novel substituted heteroaryloxyacetanilides, to a process and to intermediates for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain substituted heteroaryloxyacetanilides have herbicidal properties (cf. EP-A-037524, cf. also EP-A-005501, EP-A-18497, EP-A-37526, EP-A-37527, EP-A-94541, EP-A-100044, EP-A-148501, EP-A-300344, EP-A-348734, EP-A-348737, U.S. Pat. No. 4,509,971, U.S. Pat. No. 4,585,471, U.S. Pat. No. 4,645,525, U.S. Pat. No. 4,708,731, U.S. Pat. No. 4,968,342, and U.S. Pat. No. 4,988,380). However, the activity of these prior-art compounds is, in particular at low application rates and concentrations, not entirely satisfactory in all areas of use.
SUMMARY OF THE INVENTION
A substituted heteroaryloxyacetanilide of the general formula I
which has herbicidal activity.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel substituted heteroaryloxyacetanilides of the general formula (I)
in which
n represents the number 0, 1, 2 or 3,
R represents s-butyl, t-butyl, 1-ethyl-propyl, 2-propinyl, 1-methyl-2-propinyl, 1-ethyl-2-propinyl, 2-butinyl, 1-methyl-2-butinyl or 1-ethyl-2-butinyl,
X represents nitro, cyano, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethyl sulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, and
Z represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, oxadiazolyl, thiadiazolyl, each of which is optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or by (in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted) methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.
Preferred substituents or ranges of the radicals present in the formulae mentioned above and below are described below.
n preferably represents the number 0, 1 or 2.
R preferably represents s-butyl, t-butyl, 1-ethyl-propyl, 2-propinyl or 1-methyl-2-propinyl.
X preferably represents nitro, cyano, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
Z preferably represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, each of which is optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or by (in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted) methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.
n particularly preferably represents the number 0, 1 or 2.
R particularly preferably represents s-butyl, t-butyl, 1-ethyl-propyl, 2-propinyl or 1-methyl-2-propinyl.
X particularly preferably represents nitro, cyano, fluorine, chlorine, bromine or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
Z particularly preferably represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, each of which is optionally substituted by nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or by (in each case optionally fluorine- and/or chlorine-substituted) methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl.
n very particularly preferably represents the number 0 or 1.
R very particularly preferably represents t-butyl, 1-ethyl-propyl or 2-propinyl.
X very particularly preferably represents cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy.
Z very particularly preferably represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, each of which is optionally substituted by nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, fluorodichloromethyl, dichloromethyl, trichloromethyl, methylthio, ethylthio, n- or i-propylthio.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being preferred.
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
A very particularly preferred group are those compounds of the formula (I) in which
n represents the number 0 or 1,
R represents t-butyl,
X represents cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy, and
Z represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl or trichloromethyl.
A further very particularly preferred group are those compounds of the formula (I) in which
n represents the number 0 or 1,
R represents 2-propinyl,
X represents cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy, and
Z represents heteroaryl from the group consisting of oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl or trichloromethyl.
The novel substituted heteroaryloxyacetanilides of the general formula (I) have interesting biological properties. In particular, they have strong and selective herbicidal activity.
The novel substituted heteroaryloxyacetanilides of the general formula (I) are obtained when heteroarenes of the general formula (II)
Z—X
1
(II)
in which
Z is as defined above and
X
1
represents fluorine, chlorine, bromine, methylthio, methylsulphinyl or methylsulphonyl,
are reacted with hydroxyacetanilides of the general formula (III)
in which
n, R and X are each as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of
Dahmen Peter
Drewes Mark Wilhelm
Feucht Dieter
Kluth Joachim
Müller Klaus-Helmut
Bayer Aktiengesellschaft
Gerstl Robert
Henderson Richard E. L.
Mrozinski, Jr. John E.
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