Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2003-02-20
2004-08-03
Ramsuer, Robert W. (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S251000
Reexamination Certificate
active
06770599
ABSTRACT:
The present invention relates to novel tetrazole derivatives, to processes for their preparation, to their intermediates, to their use as herbicides and to novel herbicidal compositions for use in paddy fields.
It has been already known that certain kinds of tetrazole derivatives show a herbicidal activity (cf. Japanese Laid-open Patent Application No. 12275/1999, No. 21280/1999 etc.). Furthermore, it has been known that certain kinds of heterocyclic derivatives show a herbicidal activity (cf. U.S. Pat. Nos. 5,834,402, 5,846,906, DE-A-19846792, WO 99/10327 etc.).
There have now been found novel tetrazole derivatives of the formula (I)
wherein
R
1
represents halogen, methyl, ethyl, halomethyl, methoxy, ethoxy, C
1-2
haloalkoxy, methylthio, ethylthio, C
1-3
alkylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy, nitro or cyano,
R
2
represents C
1-6
alkyl or C
3-6
cycloalkyl which may be optionally substituted with halogen or C
1-3
alkyl, or represents C
1-4
haloallyl, C
2-6
alkenyl, or phenyl which may be optionally substituted with halogen, C
1-3
alkyl, C
1-2
haloalkyl or nitro,
m represents 0, 1 or 2,
and the two R
1
substituents may be identical or different, in case m represents 2,
n represents 1 or 2,
Q represents one of the following groups
wherein
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
are identical or different and each represents a hydrogen atom or methyl,
R
9
represents a hydrogen atom, halogen, C
1-3
alkyl, halomethyl, methoxy or nitro,
R
10
represents C
1-6
alkyl,
R
11
represents halogen, and
k represents 1 or 2.
The compounds of the formula (I), according to the invention, can be obtained by a process wherein
a) in case of preparing a compound of the formula (I) wherein Q represents groups (Q-1) or (Q-2):
compounds of the formula (II)
wherein
R
1
, R
2
, m and n have the same definition as aforementioned, and
T
1
represents one of the following groups
wherein
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
have the same definition as aforementioned,
are reacted to a rearrangement in the presence of inert solvents, and if appropriate, in the presence of a base and a cyanide, and if appropriate, in the presence of a phase-transfer catalyst,
or
b) in case of preparing a compound of the formula (I) wherein Q represents groups (Q-6) or (Q-7) and R
11
in said groups represents chloro or bromo:
compounds of the formula (Ib)
wherein
R
1
, R
2
, m and n have the same definition as aforementioned, and
Q
b
represents one of the following groups
wherein
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
have the same definition as aforementioned,
are reacted with a halogenating agent in the presence of inert solvents,
or
c) in case of preparing a compound of the formula (I) wherein Q represents groups (Q-3), (Q-4) or (Q-5):
compounds of the formula (Ic)
wherein
R
1
, R
2
, m and n have the same definition as aforementioned, and
Q
c
represents one of the following groups
wherein
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
have the same definition as aforementioned,
R
11c
represents chloro or bromo,
are reacted with compounds of the formula (III)
R
12
—SH (III)
wherein
R
12
represents the following group
or
R
10
wherein
R
9
, R
10
and k have the same definition as aforementioned,
in the presence of inert solvents, and if appropriate, in the presence of an acid binding agent.
The tetrazole derivatives of the formula (I) provided by the present invention show stronger herbicidal activity than with the compounds described in the aforementioned prior art references.
In the formulae:
“Halogen” represents fluoro, chloro, bromo or iodo, and preferably represents fluoro, chloro or bromo.
“Alkyl” can be straight chain or branched chain and there can be specifically mentioned, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, neo-, or tert-pentyl and n- or iso-hexyl.
“Cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. These cycloalkyls may be optionally substituted with halogen (for example, fluoro, chloro, bromo etc.), C
1-3
alkyl (for example, methyl, ethyl, n- or iso-propyl etc.) and in case that a plurality of substituents exist, they may be identical or different. As specific examples of such substituted cycloalkyls there can be mentioned 1-methylcyclo-propyl, 1-ethylcyclopropyl, 1-n-propylcyclopropyl, 1-methyl-2-fluorocyclopropyl, 2-methylcyclopropyl, 2-fluorocyclopropyl, 1-methyl-2,2-difluorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, 2,2difluorocyclopropyl, 2-methylcyclopentyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,6-dimethylcyclohexyl and 2,5-dimethylcyclohexyl.
As “alkenyl” there can be mentioned, for example, vinyl, allyl, 1-methylallyl, 1,1-dimetylallyl and 2-butenyl.
“Haloalkyl” represents straight chain or branched chain alkyl, of which at least one hydrogen is substituted with halogen, and there can be mentioned, for example, C
1-4
alkyl substituted with 1-6 fluoro and/or chloro, specifically difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, dichloromethyl, 2-chloro-1,1,2-trifluoroethyl, 3-fluoropropyl, 3-chloropropyl, 2,2,3,3,3-pentafluoropropyl and 1,2,2,3,3,3-hexa-fluoropropyl.
The Haloalkyl part in “haloalkoxy” can have the same definition as the afore mentioned “haloalkyl” and as “haloalkoxy” there can be specifically mentioned, for example, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2,2-trifluoroethoxy and 3-chloropropoxy.
“Alkylsulfonyl” represents an alkyl-SO
2
-group, wherein the alkyl part has the above-mentioned meaning, and includes specifically methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl.
As preferred definitions in the formula (I) there can be mentioned:
R
1
preferably represents fluoro, chloro, bromo, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, C
1-2
haloalkoxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy, nitro or cyano.
R
2
preferably represents C
1-3
alkyl, cyclopropyl which may be optionally substituted with fluoro, chloro, methyl or ethyl, C
1-3
haloalkyl, C
2-4
alkenyl, or phenyl which may be optionally substituted with fluoro, chloro, methyl, ethyl, trifluoromethyl or nitro.
m preferably represents 1 or 2.
n preferably represents 1 or 2.
R
9
preferably represents a hydrogen atom, fluoro, chloro, methyl, ethyl or tri-fluoromethyl.
R
10
preferably represents methyl or ethyl.
R
11
preferably represents chloro or bromo.
k preferably represents 1.
As more preferred definitions in the formula (I) there can be mentioned:
R
1
more preferably represents chloro, bromo, methyl or methylsulfonyl,
R
2
more preferably represents methyl, ethyl, n-propyl, isopropyl or cyclopropyl,
m more preferably represents 2, and in this case the two R
1
substituents are bond respectively to the 2-position and 4-position of a benzene ring and the two R
1
substituents may be identical or different.
n more preferably represents represents 1.
In a most preferred group of the inventive compounds the group
bonds to the 3-position (acccording to formula (I)) of the benzene ring. In another most preferred group Q represents one of the following groups
The substituents among the different ranges of preference can be combined without limitation among each other. limitation among each other.
However, as a preferred group of compounds there may be explicitly mentioned the compounds of the formula (I) wherein the substituents have the preferred meaning as described above, and as a more preferred group of compounds there may be explicitly mentioned the compounds of the formula (I) wherein the substituents have the more preferred meaning as described above.
The aforementioned preparation process (a) can be illustrated by the following reaction formula, in case of using, for example, 3-oxo-1-cyclohexenyl 2,4-dichloro-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}benzoate as the starting material.
The aforementioned preparation process (b) can be illustrated by the following reaction formula, in case of using, f
Goto Toshio
Narabu Shin-ichi
Shirakura Shinichi
Ueno Chieko
Yanagi Akihiko
Bayer CropScience KK
Harmuth Raymond J.
Henderson Richard E. L.
Ramsuer Robert W.
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