Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-11-29
2002-01-15
Gerstl, Robert (Department: 1613)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S203000, C504S263000, C548S136000, C548S221000, C564S267000
Reexamination Certificate
active
06339042
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to certain novel heteroaryloxyacetic acid N-alkenylamides, to the preparation of such compounds, to herbicidal compositions containing such compounds, and to a method of combating undesired plant growth using such compounds.
U.S. Pat. No. 4,585,471 discloses, for example, a compound of formula
which are useful as herbicides.
European patent application EP 0 005 501 discloses herbicidal benzofused oxazol-2-yl- and thiazol-2-yl-oxyacetamides, in which the amido nitrogen atom is substituted by hydrogen atoms and/or by optionally substituted alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl or aryl groups.
European patent application EP 0 165 537 discloses a process for the preparation of benzofused oxazol-2-yl- and thiazol-2-yl-oxyacetamides, in which the amido nitrogen atom is substituted by one or two allyl groups, one cyclohex-1-enyl, one cyclohex-3-enyl or one vinyl group. The compounds are taught to be useful as herbicidal agents.
International Patent Aplication WO 97/08160 discloses N-(1-isopropyl-2-methyl-1-propenyl)-heteroaryloxyacetamides, useful as herbicides.
International Patent Application WO 99/25702 discloses herbicidal heteroaryloxyacetamides, in which the amido nitrogen atom is substituted by a cyclohexenyl group.
However, none of these references disclose heteroaromatic oxyacetamides in which the amido nitrogen atom is attached to a cyclohexadienyl moiety.
Although many of the known heteroaryloxyacetamides show considerable activity against various weeds, they suffer from disadvantages due to their lack of selectivity or because of their undesirable persistence in the environment. The N-3,3,5-trimethylcyclohexadienyl heteroaryloxyacetamides of the present invention overcome these disadvantages, and also have the advantage of being obtainable from the ready available isophorone starting material. The compounds according to the present invention combine high herbicidal activity with the necessary selectivity and enhanced soil degradation.
SUMMARY OF THE INVENTION
The present invention relates to the novel compounds of the formula I
wherein
Het represents an optionally substituted, optionally benzofused nitrogen containing 5- or 6-membered heteroaromatic group;
R
1
represents an alkyl, alkoxyalkyl or cycloalkyl group;
R
2
each independently represent an alkyl or alkenyl group, and
m represents 0 or an integer from 1 to 6.
Accordingly, the present invention provides novel compounds of formula I, methods for controlling undesired plant growth by contacting said plants with a herbicidally effective amount of the new compounds, selective herbicidal compositions containing the new compounds as active ingredients, and new processes for the preparation of the aforesaid novel compounds.
These compounds show excellent herbicidal activity at low dosages combined with higher selectivity in crops than those disclosed in the aforementioned prior act patent applications. They show an excellent selective herbicidal activity in certain crops, such as rice, maize, cereals, soybeans, sugarbeets, canola, sunflowers or potatoes, and enhanced soil degradation.
These and other objects and features of the invention will become more apparent from the detailed description set forth hereinbelow.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that the novel compounds of formula I show an excellent herbicidal activity against a broad range of weeds and exhibit a high degree of selectivity.
The term “optionally benzofused nitrogen containing 5- or 6-membered heteroaromatic group” means heteroaryl groups wherein the heteroatom or atoms are one to three nitrogen, oxygen or sulfur atoms, and includes azoles, such as pyrrole, pyrazole, and imidazole, oxazoles, thiazoles, thiadiazoles, azines such as pyridine, pyrimidine, pyrazine, pyridazine and triazines. Optionally benzofused azoles are preferred. Het preferably represents a thiadiazolyl, benzoxazolyl or benzthiazolyl group which may be substituted by one or more halogen atoms or alkyl, haloalkyl or phenyl groups.
When any groups are designated as being optionally substituted, the substituent groups which are optionally present may be any of those customarily employed in the modification and/or development of pesticidal compounds and are especially substituents that maintain or enhance the herbicidal activity associated with the compounds of the present invention, or influence persistence of action, soil or plant penetration, or any other desirable property of such herbicidal compounds.
There may be one or more of the same or different substituents present in each part of the molecules.
In relation to moieties defined above as comprising an optionally substituted heteroaryl group, such optional substituents include halogen, especially fluorine, chlorine and bromine atoms, and nitro, cyano, amino, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, C
1-4
-haloalkyl, C
1-4
-haloalkenyl, C
1-4
-haloalkoxy, C
1-4
-haloalkylthio and aryl groups such as phenyl. one to five substituents may be employed, with one or two substituents being preferred and one substituent being most preferred.
Het preferably represents a group selected from the formulae (1) and (2)
in which
R
3
represents a hydrogen or halogen atom or an alkyl or haloalkyl group; preferably a C
1-4
alkyl or C
1-4
fluoroalkyl group, in particular a trifluoromethyl group
X represents O or S;
Y represents independently of each other a halogen atom or an optionally substituted alkyl group, preferably a fluoro or chloro atom or a C
1-4
alkyl, C
1-4
fluoroalkyl, C
1-4
alkoxy or C
1-4
fluoroalkoxy group, and particularly, a chloro atom or methyl atom; and
n is an integer from 0 to 4, preferably 0 or 1.
The thiadiazole derivatives (1) and the benzoxazole derivatives (2) of formula I wherein X is an oxygen atom are particularly preferred.
Generally, if any of the above mentioned moieties comprises an alkyl or alkenyl group, such groups, unless otherwise specified, may be linear or branched and may contain up to 6, preferably 1 to 4, carbon atoms. Examples of such alkyl or alkenyl groups are methyl, ethyl, propyl, (1)-butyl, isobutyl, tertiary-butyl and prop-1-en-2-yl groups. The alkyl portion of a haloalkyl, haloalkoxy, haloalkylthio, alkylthio or alkoxy group suitably has from 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms.
Generally, if any of the above mentioned moieties comprises an alkoxyalkyl group, such groups, unless otherwise specified, may be linear or branched and may contain 2 to 12, preferably 3 to 5, carbon atoms. Examples of such groups are methoxymethyl, 2-methoxyethyl, 3-methoxypropyl, 2-methoxy-1-methylethyl and methoxybutyl.
“Halogen” means a fluorine, chlorine, bromine or iodine atom, and preferably is a fluorine, chlorine or bromine substitute.
Generally, if any of the above mentioned moieties comprises a haloalkyl group, such groups, unless otherwise specified, may be linear or branched and may contain 1 to 6, preferably 1 to 4, carbon atoms. Examples of such groups are halomethyl, haloethyl, halopropyl, haloisopropyl, halobutyl, haloisobutyl and halotertiary-butyl groups. Haloalkyl moieties of any groups within the definitions used herein can contain one or more halogen atoms, preferably fluorine, chlorine or bromine. Haloalkyl represents preferably mono-, di-, tri- or perfluoroalkyl groups, especially trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl or 1,1,1-trifluoroprop-2-yl groups, with trifluoromethyl being the most preferred.
R
1
preferably represents C
1-4
alkyl, C
1-6
alkoxy-C
1-6
-alkyl or C
3-7
cycloalkyl group with methyl, ethyl, propyl, isopropyl, cyclopropyl and 2-methoxyethyl groups being most preferred.
R
2
preferably each independently represent a C
1-4
alkyl or C
2-4
alkenyl group, and most preferably, a methyl group or prop-1-en-2-yl group. The m variable is preferably 1, 2 or 3, and most preferably is 3.
Particularly preferred are the compounds of formula IA,
wherein Het, R
1
and R
2
are as hereinbefore defined and the dashed line indicates the presence of t
Baltruschat Helmut Siegfried
Newton Trevor
American Cyanamid Co.
Gerstl Robert
Maurer Barbara V.
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