Tetrazolinone derivatives

Details Tetrazolinone derivatives Tetrazolinone derivatives

2003-06-30

2004-09-14

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S251000

Reexamination Certificate

active

06790810

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to novel tetrazolinone derivatives, to processes for their preparation and to their use as herbicides.
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
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.


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