Herbicidal tetrazolinone derivatives

Details Herbicidal tetrazolinone derivatives Herbicidal tetrazolinone derivatives

2002-02-05

2003-09-23

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S251000

Reexamination Certificate

active

06624121

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel tetrazolinone derivatives, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It has already been known that certain kinds of tetrazole derivatives show herbicidal activity (Japanese Laid-open Patent Application Nos. 12275/1999 and 21280/1999). Moreover, it has further already been known, that certain kinds of heterocyclic derivatives also show herbicidal activity (U.S. Pat. Nos. 5,834,402 and 5,846,906).
SUMMARY OF THE INVENTION
The present invention provides novel tetrazolinones of the general formula (I)
wherein
R
1
represents halogen, C
1-4
alkyl, C
1-4
haloalkyl, C
1-4
alkoxy, C
1-4
alkylthio, C
1-4
alkylsulfonyl, C
1-4
alkylsulfonyloxy, C
2-5
alkoxycarbonyl, C
2-6
alkoxyalkyl, C
2-6
alkylthioalkyl, nitro or cyano,
R
2
represents a hydrogen atom, C
1-6
alkyl, C
3-6
cycloalkyl which may be optionally substituted with halogen or C
1-3
alkyl, C
1-4
haloalkyl, or phenyl which may be optionally substituted with halogen, C
1-3
alkyl, C
1-3
haloalkyl or nitro,
m represents 0, 1 or 2
n represents 0 or 1, and
Q represents one of the groups disclosed herein.
The present invention further provides methods of using the novel tetrazolinones as herbicides.
The present invention yet further provides a process for preparation of the novel tetrazolinones.
DETAILED DESCRIPTION OF THE INVENTION
There have now been found novel tetrazolinone derivatives of the general formula (I)
wherein
R
1
represents halogen, C
1-4
alkyl, C
1-4
haloalkyl, C
1-4
alkoxy, C
1-4
alkylthio, C
1-4
alkylsulfonyl, C
1-4
alkylsulfonyloxy, C
2-5
alkoxycarbonyl, C
2-6
alkoxyalkyl, C
2-6
alkylthioalkyl, nitro or cyano,
R
2
represents a hydrogen atom, C
1-6
alkyl, C
3-6
cycloalkyl which may be optionally substituted with halogen or C
1-3
alkyl, C
1-4
haloalkyl, or phenyl which may be optionally substituted with halogen, C
1-3
alkyl, C
1-3
haloalkyl or nitro,
m represents 0, 1 or 2; while the two R
1
substituents may be identical or different, in case m represents 2,
n represents 0 or 1, and
Q represents one of the following groups
 in which
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
each independently represent a hydrogen atom or C
1-4
alkyl, or
R
3
and R
8
may form an ethylene chain together,
R
9
represents C
1-4
alkyl,
R
10
represents C
1-4
alkyl or C
3-6
cycloalkyl which may be optionally substituted with methyl.
The compounds of the general formula (I), according to the invention, can be obtained by a process in which
a) compounds of the general formula (IIa)
 wherein
R
1
, R
2
, m and n have the same definition as aforementioned, and
T
1
represents one of the following groups
 in which
R
3
, R
4
, R
5
, R
6
, R
7
, R
8
and R
9
have the same definition as mentioned above,
are reacted to a rearrangement in the presence of a base and a cyanide, or
b) in case that Q represents group (Q-2):
compounds of the general formula (IIb)
wherein
R
1
, R
2
, m and n have the same definitions as mentioned above, and
T
2
represents one of the following groups;
 in which
R
9
has the same definition as mentioned above,
are reacted to a rearrangement in the presence of a base, or
c) in case that Q represents group (Q-3):
compounds of the general formula (III)
wherein
R
1
, R
2
, R
10
, m and n have the same definitions as mentioned above, and
R
11
represents C
1-4
alkyl, preferably methyl or ethyl,
are reacted with hydroxylamine, or
d) in case that Q represents group (Q-4):
compounds of the general formula (Ib)
wherein
R
1
, R
2
, R
10
, m and n have the same definition as mentioned above,
are reacted to a ring-opening in the presence of a base.
The tetrazolinone derivatives of the general formula (I) provided by the present invention show a superior herbicidal activity compared with the compounds described in the aforementioned prior art literatures.
In the general formulae:
“Halogen” represents fluoro, chloro, bromo or iodo, and preferably represents fluoro, chloro or bromo.
“Alkyl” may be straight or branched chain and there may be mentioned, for example, C
1-6
alkyl specifically methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, neo-, or tert-pentyl, n- or iso-hexyl.
As “cycloalkyl” there can be mentioned, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. These cycloalkyls may be optionally substituted with halogen (for example, fluorine, chlorine or bromine), C
1-3
alkyl (for example, methyl, ethyl, n- or iso-propyl) and in case a plurality of substituents exist, they may be identical or different.
As specific examples of such substituted cycloalkyls there can be mentioned 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-n-propylcyclopropyl, 1-methyl-2-fluoro-cyclopropyl, 2-methylcyclopropyl, 2-fluorocyclopropyl, 1-methyl-2,2-difluorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, 2,2-difluorocyclopropyl, 2-methylcyclopentyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 2,5-dimethyl-cyclohexyl.
“Haloalkyl” represents straight or branched chain alkyl, of which at least one hydrogen is substituted with halogen, and there may be mentioned, for example, C
1-4
alkyl substituted with 1 to 6 fluorine atoms and/or chlorine atoms, and more specifically for example difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, di-chloromethyl, 2-chloro-1,1,2-trifluoroethyl, 3-fluoropropyl, 3-chloropropyl, 2,2,3,3,3-pentafluoropropyl or 1,2,2,3,3,3-hexafluoropropyl.
“Alkoxy” represents an —O-alkyl group, of which the alkyl part has the above-mentioned meaning. “Alkoxy” and can be, for example, C
1-4
alkoxy, and more specifically for example methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy.
“Alkylthio” represents an -S-alkyl group, of which the alkyl part has the above-mentioned meaning. “Alkylthio” can be, for example, C
1-4
alkylthio, and more specifically for example methylthio, ethylthio, n- or iso-propylthio, n-, iso-, sec- or tert-butylthio.
“Alkylsulfonyl” represents a —SO
2
-alkyl group, of which the alkyl part has the above-mentioned meaning. “Alkylsulfonyl” can be, for example, C
1-4
alkylsulfonyl, and more specifically for example methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl.
“Alkylsulfonyloxy” represents a —O—SO
2
-alkyl group, of which the alkyl part has the above-mentioned meaning. “Alkylsulfonyloxy” can be, for example, C
1-4
alkylsulfonyloxy, and more specifically for example methylsulfonyloxy, ethylsulfonyloxy, n- or iso-propylsulfonyloxy, n-, iso-, sec- or tert-butylsulfonyloxy.
“Alkoxycarbonyl” represents a —CO—O-alkyl group, of which the alkyl part has the above-mentioned meaning. “Alkoxycarbonyl” can be, for example, C
2-5
alkoxycarbonyl, and more specifically for example methoxycarbonyl, ethoxycarbonyl, n- or iso-propoxycarbonyl, n-, iso-, sec- or tert-butoxycarbonyl.
“Alkoxyalkyl” represents alkyl substituted with alkoxy and can be, for example, C
2-6
alkoxyalkyl, and more specifically for example methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-methoxy-1-methylethyl, methoxypropyl, methoxybutyl, methoxypentyl, ethoxymethyl, n- or iso-propoxymethyl, n-, iso-, sec- or tert-butoxymethyl.
“Alkylthioalkyl” represents alkyl substituted with alkylthio and can be, for example, C
2-6
alkylthioalkyl, and more specifically for example methylthiomethyl, methylthiomethyl, 1-methylthiopropyl, 2-methylthiopropyl, 1-methyl-2-methylthioethyl, methylthiobutyl, methylthiopentyl, ethylthiomethyl, n- or iso-propylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl.
As a preferred group of compounds of the present invention there can be mentioned the compounds of the aforementioned general formula (I) wherein
R
1
represents fluoro, chloro, bromo, methyl, ethyl, C
1-2
haloalkyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy, methoxycarbonyl, ethoxycarbonyl, C
2-4
alkoxyalkyl, C
2-4
alkylthioalkyl, nitro or cyano,
R
2
repr

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