Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-01-22
2002-10-01
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S319000
Reexamination Certificate
active
06458748
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel di- or trifluoromethanesulfonyl anilide derivative or a salt thereof; a process for production thereof; a herbicide containing said derivative or salt as an active ingredient; and novel raw material compounds used in said process.
BACKGROUND ART
It is known that N-fluoromethanesulfonyl anilide derivatives having a pyrimidinyl-containing group at the 2-position, for example, an N-trifluoromethanesulfonyl anilide derivative of 2-pyrimidinylmethyl-substituted or 2-pyrimidinyloxy or thioxy-substituted aniline has a herbicidal activity (see National Publication of International Patent Application No. 7-501053 and WO 93/09099).
It is also known that an N-trifluoromethanesulfonyl anilide derivative of 2-pyrimidinylhydroxymethyl-substituted aniline has a plant growth-regulating activity (see WO 96/41799).
However, it is not yet known that any of N-di- or trifluoromethanesulfonyl derivatives of aniline having a pyrimidinyl-containing group at the 2-position has a herbicidal activity.
In the cultivation of paddy rice, it has been an important task in recent years to control noxious weeds which emerge in paddy field and which are difficult to control effectively with conventional herbicides, i.e. difficult-to-control weeds. These weeds emerge over a long period of time and, therefore, need to be controlled over a long period of time. Gramineous weeds (other than rice plant) belonging to the same family as rice plant belongs to, for example,
Echinochloa oryzicola
Vasing., etc. emerge over a long period of time as well and grow actively and rapidly; therefore, their control is important as well. No herbicide is developed currently which has a high activity to the above weeds and can control them. Hence, it is desired to develop a chemical agent which has a high herbicidal activity not only to difficult-to-control weeds but also to gramineous weeds, which can control a wide variety of weeds emerging in paddy field, over a long period of time, and which is highly safe to mammals.
Under the above situation, the present invention aims at providing a novel compound which is effective for the removal of a wide variety of weeds including difficult-to-control weeds, emerging in paddy field and which is safe to mammals; a process for production thereof; a herbicide containing the compound as an active ingredient; and novel raw material compounds used in said process.
DISCLOSURE OF THE INVENTION
The present inventors made an intensive study to develop a novel compound having a herbicidal activity. As a result, the present inventors found out that an N-di- or a trifluoromethanesulfonyl derivative of 2-pyrimidinylhydroxymethyl-substituted aniline has a herbicidal activity to a wide variety of weeds at a low dosage, is very effective particularly to gramineous weeds and, moreover, is highly safe to mammals. The present invention has been completed based on the above finding.
The present invention provides a di-, or trifluoromethanesulfonyl anilide derivative represented by the following general formula (I):
(wherein R
1
is a hydrogen atom, an alkyl group or an alkoxyalkyl group; and R
2
is a hydrogen atom when R
1
is a hydrogen atom or an alkyl group, and is a hydrogen atom or a fluorine atom when R
1
is an alkoxyalkyl group), or a salt thereof, both of said derivative and said salt having a herbicidal activity.
Each of the compounds represented by the general formula (I) can be produced, for example, by reacting a 2-substituted aniline derivative (II) with a di- or trifluoromethanesulfonyl halide or trifluoromethanesulfonic-acid anhydride according to the following reaction formula (1):
(wherein X is a halogen atom, and R
1
and R
2
each have the same definition as given above), or by reducing a 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)-N-di- or trifluoromethanesulfonyl anilide derivative (III) according to the following reaction formula (2):
(wherein R
1
and R
2
each have the same definition as given above).
The compounds represented by the general formula (II) or (III), used in the above production processes are also novel compounds not described in any literature.
In the present compound represented by the general formula (I), R
1
is a hydrogen atom, an alkyl group or an alkoxyalkyl group. The alkyl group is preferably a straight chain or branched chain alkyl group having 1 to 5 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tertbutyl group, n-pentyl group, 1-methylbutyl group, n-hexyl group or the like. The alkoxyalkyl group is preferably a straight chain or branched chain alkoxyalkyl group having 2 to 6 carbon atoms, such as methoxymethyl group, methoxyethyl group, ethoxyethyl group, 3-ethoxypropyl group, 1-methyl-3-methoxybutyl group or the like.
In the present compound represented by the general formula (I), R
2
is a hydrogen atom when R
1
is a hydrogen atom or an alkyl group, and is a hydrogen atom or a fluorine atom when R
1
is an alkoxyalkyl group. When R
2
is a hydrogen atom, the present compound represented by the general formula (I) is a difluoromethanesulfonyl anilide derivative; when R
2
is a fluorine atom, the present compound represented by the general formula (I) is a trifluoromethanesulfonyl anilide derivative.
The salt of the compound represented by the general formula (I) is a salt between the sulfonylamide group moiety of the compound and a base. As the base, there can be mentioned a sodium salt and a potassium salt.
As the representative examples of the di- or trifluoromethanesulfonyl anilide derivative represented by the general formula (I), there can be mentioned 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-methoxymethyl-N-difluoromethanesulfonyl anilide, 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-methoxyethyl-N-difluoromethanesulfonyl anilide, 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-ethoxymethyl-N-difluoromethanesulfonyl anilide, 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-N-difluoromethanesulfonyl anilide, 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-ethyl-N-difluoromethaesulfonyl anilide, 2-[( 4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-methoxymethyl-N-trifluoromethanesulfonyl anilide, 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-methoxyethyl-N-trifluoromethanesulfonyl anilide, and 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-ethoxymethyl-N-trifluoromethanesulfonyl anilide.
The compound represented by the general formula (I) can be produced, for example, by reacting a 2-substituted aniline derivative represented by the general formula (II) with a di- or trifluoromethanesulfonyl halide or trifluoromethanesulfonic acid anhydride according to the above-shown reaction formula (1), or by reducing a 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)-N-di- or trifluoromethanesulfonyl anilide derivative represented by the general formula (III) according to the above-shown reaction formula (2).
The former process is conducted ordinarily in the presence of a base in an inert solvent such as aliphatic or alicyclic hydrocarbon (e.g. pentane, hexane or cyclohexane), aromatic hydrocarbon (e.g. toluene or xylene), halogenated hydrocarbon (e.g. dichloromethane or chloroform), ether (e.g. diethyl ether, tetrahydrofuran or 1,4-dioxane), ester (e.g. methyl acetate or ethyl acetate), nitrile (e.g. acetonitrile or propionitrile), aprotic polar solvent (e.g. N,N-dimethylformamide, N,N-dimethyl sulfoxide or sulfolane) or mixture thereof.
The base used above is a base conventionally used in a reaction between aniline and acid halide, such as alkali metal hydroxide (e.g. sodium hydroxide or potassium hydroxide), alkaline earth metal hydroxide (e.g. calcium hydroxide) or organic base (e.g. trimethylamine, triethylamine, N,N-dimethylaniline or pyridine).
The reaction temperature is selected in a range of −70 to 250° C., preferably −70 to 40° C. The reaction time differs depending upon the kinds of raw material compounds us
Danjo Takeshi
Nakatani Masao
Ono Yukimasa
Tamaru Masatoshi
Yanagisawa Katsutada
Ford John M.
Ihara Chemical Industry Co. Ltd.
Kubovcik & Kubovcik
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