5-Iodo-4-phenethylaminopyrimidine derivative, intermediate...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C544S326000

Reexamination Certificate

active

06521627

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a novel 5-iodo-4-phenethylaminopyrimidine derivative useful as agricultural and horticultural pesticides, a novel 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine which is a preparation intermediate thereof, processes for producing these compounds and agricultural and horticultural pesticides.
PRIOR ART
Some 4,5-dihalogeno-6-(&agr;-substituted ethyl)pyrimidines useful as an intermediate for medicines or agricultural chemicals have been known (for example, Japanese Provisional Patent Publication No. 320141/1993, etc.). However, 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine in which the 5-position of the pyrimidine ring is substituted by an iodine atom as in the present invention has not yet been disclosed.
Moreover, as a 4-phenethylaminopyrimidine derivative which is similar to the present invention, there is Japanese Provisional Patent PublicationNo. 258223/1995. However, the 4-phenethylaminopyrimidine derivative in which the 5-position of the pyrimidine ring is substituted by an iodine atom has not been disclosed.
Accordingly, the 5-iodo-4-phenethylaminopyrimidine derivative of the present invention would be a novel compound is a novel compound and it has been not known to have agricultural and horticultural pesticidal activities.
An object of the present invention is to provide a novel 5-iodo-4-phenethylaminopyrimidine derivative, its process for producing the same, and an agricultural and horticultural pesticide containing the same as an effective ingredient.
Another object of the present invention is to provide a novel 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine which is useful as an intermediate for medicines and agricultural chemicals.
SUMMARY OF THE INVENTION
The present inventors have studied to solve the above-mentioned problems, and as a result, they have found that a novel 5-iodo-4-phenethylaminopyrimidine has remarkable agricultural and horticultural insecticidal, acaricidal, nematocidal and fungicidal activities whereby they have accomplished the present invention.
Also, the present inventors have also studied to solve the above-mentioned problems, and as a result, they have found a process for producing a novel 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine, whereby they have accomplished the present invention.
That is, the present invention is as mentioned below.
The first invention relates to a 5-iodo-4-phenethylaminopyrimidine derivative represented by the following formula (1):
wherein R
1
represents a halogen atom, an acyloxy group having 2 to 4 carbon atoms or a hydroxyl group; R
2
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms;
n is an integer of 1 to 3; and * represents an asymmetric carbon atom.
The second invention relates to a process for producing the 5-iodo-4-phenethylaminopyrimidine derivative represented by the above-mentioned formula (1) which comprises allowing a pyrimidine represented by the following formula (2):
wherein R
1
and * have the same meanings as defined above, to react with a phenethylamine represented by the following formula (3):
wherein R
2
and n have the same meanings as defined above.
The third invention relates to a 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine represented by the following formula (2):
wherein R
1
and * have the same meanings as defined above.
The fourth invention relates to a process for producing 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine represented by the following formula (2-1):
wherein R
3
represents a chlorine atom or a bromine atom and * has the same meaning as defined above, which comprises allowing a pyrimidine represented by the following formula (4):
to react with a halogen represented by the following formula (5):
(R
3
)
2
  (5)
wherein R
3
has the same meaning as defined above.
The fifth invention relates to a process for producing a 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine represented by the following formula (2-2):
wherein R
4
represents an acyloxy group having 2 to 4 carbon atoms, and * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-1):
wherein R
3
and * have the same meanings as defined above, to react with a lower aliphatic acid represented by the following formula (6):
R
4
—H   (6)
wherein R
4
has the same meaning as defined above.
The sixth invention relates to a process for producing a 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine represented
by the following formula (2-3):
wherein * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-2):
wherein R
4
and * have the same meanings as defined above, to react with an inorganic base represented by the following formula (7):
M—OH   (7)
wherein M represents an alkali metal.
The seventh invention relates to a process for producing a 4-chloro-5-iodo-6-(&agr;-substituted ethyl)pyrimidine represented by the following formula (2-4):
wherein * has the same meaning as defined above, which comprises allowing the pyrimidine represented by the following formula (2-3):
wherein * has the same meaning as defined above, to react with a fluorinating agent represented by the following formula (8):
The eighth invention relates to agricultural and horticultural pesticides containing the 5-iodo-4-phenethylaminopyrimidine represented by the above-mentioned formula (1) as an effective ingredient.
DETAILED DESCRIPTION OF THE INVENTION
In the following, the present invention is explained in detail.
Various kinds of the substituents mentioned in the above respective compounds are as follows.
(R
1
)
R
1
represents a halogen atom, an acyloxy group having 2 to 4 carbon atoms or a hydroxyl group.
As the halogen atom, there may be mentioned a chlorine atom, an iodine atom, a bromine atom, a fluorine atom, etc.; and preferably a chlorine atom and a fluorine atom.
As the acyloxy group having 2 to 4 carbon atom, there may be mentioned those having a straight or branched alkyl group; preferably an acetyloxy group.
(R
2
)
R
2
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms.
As the halogen atom in R
2
, there may be mentioned a chlorine atom, an iodine atom, a bromine atom, a fluorine atom, etc.; and preferably a chlorine atom and a fluorine atom.
As the alkyl group having 1 to 4 carbon atoms, there may be mentioned a straight or branched alkyl group; and preferably a methyl group.
As the haloalkyl group having 1 to 4 carbon atoms, there may be mentioned a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2-fluoroethyl group, etc., and preferably a trifluoromethyl group.
As the alkoxy group having 1 to 4 carbon atoms, there may be mentioned a straight or branched one, and preferably a methoxy group.
As the haloalkoxy group having 1 to 4 carbon atoms, there may be mentioned a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2-fluoroethoxy group, etc., and more preferably a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group.
(n)
n is an integer of 1 to 3; and preferably 1 or 2.
The compounds (1) of the present invention have an amino group so that an acid addition salt derived therefrom is also included in the present invention.
As an acid which forms an acid addition salt, there may be mentioned, for example, an inorganic acid such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.; a carboxylic acid such as formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, etc.; a sulfonic acid such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.; saccharine, etc.
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