Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1986-03-26
1987-09-15
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07C12912
Patent
active
046940863
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to novel guanidine derivatives which can be effectively used as the fungicide to the plant which shows high fungicidal activity against many kinds of plant diseases such as pear black spot. Alternaria leaf spot of apple. Alternaria black spot of strawberry, tobacco brown spot and black spot of apple with substantially no phytotoxicity to plant.
DESCRIPTION OF THE PRIOR ART
It has been known that the guanidino compounds can be the effective fungicide against the plant diseases particularly caused by fungi.
For example, in the prior arts, the guanidino compound having the following formula was well used as such a fungicide. ##STR2##
This guanidino compound, however, has the defects that it does not possess a sufficient antifungal property and it brings about high order of phytotoxicity to the plant if it is used in a high concentration so as to attain a sufficient antifungal effect. In particular, the latter is to be decisive because according to the general method of usage fungicide is sprayed to the plant in the state of solution, dispersion, or emulsion and thereafter the concentration of guanidino compound as the fungicide on the plant becomes extremely high by evaporation of the solvent. According to Japanese Patent Publication No. 42-16607, it is also known that di(8-guanidino octyl)amine possesses an antifungal property for the plant.
But this compound cannot be said to be satisfactory in view of both fungicidal activity and phytotoxicity to the plant.
DISCLOSURE OF THE INVENTION
The first object of the present invention is to provide novel guanidine derivatives which can be effectively utilized as such a fungicide as possessing a high fungicidal activity against the plant diseases and, at the same time, having substantially no phytotoxicity to the plant.
The second object of the present invention is to provide the novel guanidine derivatives which can be effectively utilized as the fungicide possessing a high fungicidal activity especially against plant diseases such as pear black spot. Alternaria leaf spot of apple. Alternaria black spot of strawberry, tobacco brown spot and black spot of apple without substantially imparting damage to the plants thereof.
It has now been found that the objects of the present invention can be effectively attained by the novel guanidine derivatives selected from the group consisting of the compound having the following formula (I) and the acid adducts thereof. ##STR3##
Further, it has been found that the objects of the present invention can be more effectively attained by acid adducts of the compound having the above formula (I) derived from an acid selected from sulfuric acid, acetic acid, or hydrochloic acid.
DESCRIPTION OF THE PREFERRED EMBODIMENT OF THE INVENTION
At first a process for producing the guanidine derivatives of the present invention, subsequently said guanidine derivatives themselves, and finally the fungicidal activity of said guanidine derivatives, are described.
The guanidine derivatives of the present invention are provided by reacting 1,6,11-triaminoundecane with isothiourea derivatives respresented by the following formula (II). ##STR4## wherein R represents lower alkyl, benzyl, and aralkyl.
This reaction is shown in the following reaction formula (III). ##STR5##
The isothiourea derivative represented by the above formula (II) is subjected to the reaction in the state of the salt thereof with strong acid such as sulfuric acid, nitric acid, hydrochloric acid, carbonic acid, formic acid, acetic acid, propionic acid, oxalic acid, furmaric acid, or citric acid.
S-methylisothiourea sulfate out of isothiourea derivatives is most preferably used.
1,6,11-triaminoundecane can be prepared by the conventional methods, for example by heating .epsilon.-caprolactam at a temperature higher than 300.degree. C. in the presence of a strong base selected from oxides or hydroxides of alkali metal or alkaliearth metal to form 7-(5'-aminopentyl)-3,4,5,6-tetrahydro-2H-azepin and thereafter subjecting it to
REFERENCES:
patent: 3499927 (1970-03-01), Badcock et al.
Morimoto Hiroshi
Ohura Akio
Hendriksen L.
Killos Paul J.
Miller Austin R.
Toray Industries Inc.
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