Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-02-21
1999-12-28
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546329, 548203, 548205, 558 8, C07C27708, C07C27936, C07C27318, C07D27728, C07D21338, C07D20948
Patent
active
060083638
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing guanidine derivatives which are useful as insecticides, novel intermediates therefor, and a process for producing the intermediates.
BACKGROUND ART
EP-A 376279 corresponding to JP-A H3(1991)-157308, for instance, describes guanidine derivatives having pesticidal activity and a process for producing the derivatives. Moreover, as an improved production process for the guanidine derivatives, EP-A 452782 corresponding to JP-A H5(1993)-9173 discloses a production process via an isothiourea derivative having a cyclic diacyl group as shown in the following schema 1. ##STR2## wherein R.sub.1, R.sub.2, R.sub.4a, and R.sub.5a are the same or different, H or a hydrocarbon group which may optionally be substituted; A' is a divalent hydrocarbon group which may optionally be substituted; Q' is a heterocyclic group which may optionally be substituted; X' is an electron withdrawing group; Y.sub.1 and Y.sub.2 are the same or different, a leaving group; n is 0 or 1.
Furthermore, EP-A 375907 corresponding to JP-A H2(1990)-288860 discloses guanidine derivatives having pesticidal activity, and the following process for producing the derivatives. ##STR3## wherein R.sup.1' and R.sup.2' are hydrogen or C.sub.1-4 alkyl, R.sup.4' is C.sub.1-4 alkyl, Z is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halegen or C.sub.1-4 alkyl, R.sup.5' and R.sup.6' are hydrogen or C.sub.1-4 alkyl.
However, in these processes for producing the guanidine derivatives, there are some problems such that a mercaptan compound of RSH (wherein R is a hydrocarbon group which may optionally be substituted) having bad smell is formed as a by-product.
In the above state of the art, the object of present invention is to provide a process which is advantageous to an industrial mass production of guanidine derivatives in a higher yield by simple and convenient reaction procedures without bad smell, novel intermediates therefor, and a process for producing the intermediates.
DISCLOSURE OF INVENTION
To accomplish the above-mentioned object, the inventors of the present invention earnestly explored for a new production route to a guanidine derivative of the formula [I]: ##STR4## wherein R.sup.2 is H or a hydrocarbon group which may optionally be substituted; R.sup.3 is an amino group which may optionally be substituted; Q is a heterocyclic group which may optionally be substituted; X is an electron attracting group; n is 0 or 1.
As a result, the inventors discovered that an N-cyclodiacyl-N'-substituted isourea derivative of the formula [IV]: ##STR5## wherein R.sup.1 is a hydrocarbon group which may optionally be substituted, A is a divalent hydrocarbon group which may optionally be substituted, and X is as defined above, can be produced in high yield by reacting an N-substituted isourea derivative of the formula [II]: ##STR6## wherein the symbols are as defined above, or a salt thereof, with a compound of the formula [III]: ##STR7## wherein Y.sup.1 and Y.sup.2 are the same or different, a leaving group; A is as defined above.
The inventors further found that a compound of the formula [VI]: ##STR8## wherein the symbols are as defined above, or a salt thereof, can be produced in high yield by reacting the compound [IV] with a compound of the formula [V]:
Based on the above findings, the inventors did further research and found surprisingly that when the compound [VI] or a salt thereof is reacted with an amine or a salt thereof either in water or in a mixture of water and an organic solvent, the guanidine derivative [I] or a salt thereof is produced in high yield.
And, the inventors further found that the compound [VI] or a salt thereof can be produced by reacting the compound [II] or a salt thereof with the compound [V] or a salt thereof not via the compound [IV]. The inventors did further reseach and discovered to their own surprise that the compound [VI] or a salt thereof can be produced in a further improved yield by conducting t
REFERENCES:
patent: 5034404 (1991-07-01), Uneme et al.
patent: 5180833 (1993-01-01), Uneme et al.
patent: 5214152 (1993-05-01), Minamida et al.
patent: 5489603 (1996-02-01), Uneme et al.
Heyboer et al, Rec, Trav. Chim., vol. 81, pp. 69 to 72, 1962.
Ishizuka Hitoshi
Kamiya Yasuo
Konobe Masato
Uneme Hideki
Higel Floyd D.
Takeda Chemical Industries Ltd.
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