Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-10-30
2004-03-16
Rotman, Alan L. (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S217000, C548S237000
Reexamination Certificate
active
06706664
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a benzoxazole compound, a process for producing the same and a herbicide containing the same as an effective ingredient.
BACKGROUND ART
As a similar compound to a compound (1) according to the present invention, there is a compound represented by the following formula:
wherein R
1
to R
6
each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a halogen atom or a nitro group; A and B each represents O or S; R
7
represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, etc.; and R
8
represents an alkyl group having 1 to 6 carbon atoms, etc.,
as disclosed in Japanese Provisional Patent Publication No. 139767/1998.
However, this compound is a compound different in at least —NR
8
CBR
9
portion from the compound of the present invention.
Accordingly, since the compound (1) of the present invention is novel, its use has never been known. Also, a compound (6) which is a synthetic intermediate thereof is also a novel compound.
An object of the present invention is to provide a herbicide containing a benzoxazole compound as an effective ingredient.
SUMMARY OF THE INVENTION
The present inventors have earnestly investigated to solve the above-mentioned problems, and as a result, they have found that a chemical containing a novel benzoxazole derivative as an effective ingredient is effective as a herbicide whereby they have accomplished the present invention.
That is, the present invention is as follows:
The first invention relates to a benzoxazole compound represented by the following formula (1):
wherein R
1
to R
4
each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, a cyano group, a carboxyl group, an alkoxycarbonyl group having 2 to 5 carbon atoms, R
8
S(O)
n
or R
9
NH group; R
8
represents an alkyl group having 1 to 6 carbon atoms; n is an integer of 0 to 2; R
9
represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms; or a trifluoromethylcarbonyl group; R
5
represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, a cyano group or R
8
S(O)
n
; R
8
has the same meaning as defined above; R
6
represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a cyano group, a nitro group or a haloalkyl group having 1 to 4 carbon atoms; R
7
represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms or a phenyl group; and X represents O, S, SO or SO
2
.
The second invention relates to a process for preparing a compound (1′) represented by the following formula (1′) where X in the formula (1) is an oxygen atom or a sulfur atom:
wherein R
1
to R
7
have the same meanings as defined above; and X′ represents an oxygen atom or a sulfur atom,
which comprises allowing a compound (2) represented by the following formula (2):
wherein R
1
to R
4
and R
7
have the same meanings as defined above; and Y represents a halogen atom, a methanesulfonyloxy group or a p-toluenesulfonyloxy group,
to react with a compound represented by the following formula (3):
wherein R
5
and R
6
; and X′ have the same meanings as defined above,
in a solvent in the presence of a base.
The third invention relates to a process for preparing the compound (1) represented by the above formula (1), which comprises allowing a compound (4) represented by the following formula (4):
wherein R
1
to R
4
have the same meanings as defined above,
to react with a compound represented by the following formula (5):
wherein R
5
to R
7
and X have the same meanings as defined above,
or a reactive derivative thereof.
The fourth invention relates to a compound represented by the following formula (6):
wherein R
1
to R
7
have the same meanings as defined above.
The fifth invention relates to a herbicide containing the above-mentioned compound (1) as an effective ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
In the following, the present invention is explained in detail.
Incidentally, in the explanation of the invention, it is mentioned as a compound (numeral) with an Arabic numeral with blankets attached to a chemical formula (for example, that shown by the formula (1) is also referred to as the compound (1).).
Symbols such as R
1
to R
7
, X, X′, Y, etc. shown in the compounds (1) to (6) of the present invention have the meanings as mentioned below. (R
1
to R
4
)
As R
1
to R
4
, there may be mentioned a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, a cyano group, a carboxyl group, an alkoxycarbonyl group having 2 to 5 carbon atoms, R
8
S(O)
n
or R
9
NH group.
Incidentally, R
8
represents an alkyl group having 1 to 6 carbon atoms; n is an integer of 0 to 2; and R
9
represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkylcarbonyl group having 2 to 4 carbon atoms.
(1) In R
1
to R
4
,
the alkyl group is a straight or branched one; preferably that having 1 to 4 carbon atoms; more preferably that having 1 to 3 carbon atoms (for example, there may be mentioned a methyl group, an ethyl group and a propyl group.).
The alkoxy group is a straight or branched one; preferably that having 1 to 4 carbon atoms; more preferably that having 1 to 3 carbon atoms (for example, there may be mentioned a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group.).
The haloalkyl group is a straight or branched one; preferably that having 1 to 4 carbon atoms which has a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; more preferably that having 1 to 3 carbon atoms (for example, there may be mentioned a chloromethyl group, a chloroethyl group and a trifluoromethyl group.).
The haloalkoxy group is a straight or branched one; preferably that having 1 to 4 carbon atoms; more preferably that having 1 to 3 carbon atoms which has a fluorine atom, a chlorine atom, a bromine atom or an iodine atom (for example, there may be mentioned a trifluoromethoxy group and a trifluoroethoxy group.).
The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; preferably a chlorine atom.
The alkoxycarbonyl group is a straight or branched one; preferably that having an alkoxy with 1 to 4 carbon atoms; more preferably that having an alkoxy with 1 to 3 carbon atoms (for example, there may be mentioned a methoxycarbonyl group, an ethoxycarbonyl group and an isopropoxycarbonyl group.).
(2) In R
8
,
R
6
is a straight or branched alkyl group; preferably that having 1 to 4 carbon atoms; more preferably that having 1 to 3 carbon atoms (for example, there may be mentioned a methyl group.).
(3) In n,
n is an integer of 0, 1 or 2, preferably 0 or 2.
(4) In R
9
,
as R
9
, there may be mentioned a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a trifluoromethylcarbonyl group.
The alkyl group is a straight or branched one; preferably those having 1 to 4 carbon atoms; more preferably those having 1 to 3 carbon atoms (for example, there may be mentioned a methyl group, an ethyl group, a propyl group.).
The alkylcarbonyl group is a straight or branched one; preferably those having alkyl with 1 to 3 carbon atoms; more preferably those having alkyl with 1 or 2 carbon atoms (for example, there may be mentioned a methylcarbonyl group, an ethylcarbonyl group.).
(R
5
)
As R
5
, there may be mentione
Asahara Takehiko
Fukuda Shohei
Nakamura Akira
Okada Tatsuo
Oohida Satoshi
Shameem Golamm M M
UBE Industries Ltd.
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