Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Biocides; animal or insect repellents or attractants
Patent
1999-08-26
2000-11-07
McKane, Joseph
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Biocides; animal or insect repellents or attractants
514720, 514520, 558423, 568593, A61K 31275, A61K 31075, C07C25559, C07C 4312, A01N 2534
Patent
active
06143311&
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel iodopropargyl derivatives which have a reduced smell as well as a wide antimicrobial spectrum and a high antimicrobial activity. Moreover, it relates to antimicrobial, antifungal and also preservative or antimold agents comprising said derivatives as an active ingredient, which can be suitably used industrially.
BACKGROUND ART
It is hitherto known that an organic iodide series of antimicrobial agents such as 1-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy]benzene and 1-[[(3-iodo-2-propynyl)oxy]-methoxy]-3-methylbenzene, both of which are described in JP-B-47/24121 as 4-chlorophenyl 3-iodopropargyl formal and meta-cresyl 3-iodopropargyl formal, respectively, 3-bromo-2,3-diiodo-2-propenyl-ethylcarbonate and 3-iodo-2-propynyl-butylcarbamate are predominantly used for preservative and antimold purposes for wood. Moreover, antifungal agents such as phenyl-11-iodo-10-undecynoate and 3-iodo-2-propynyl-2,4,5-trichlorophenyl ether are known in the art. Although each of the above antimicrobial agents has a particular antimicrobial spectrum, it may have drawbacks such as a relatively high toxicity against the human body, an insufficient effect on particular microorganisms and/or a strong smell.
Among others, 1-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy]benzene has excellent properties such as a particularly high antimicrobial activity against mold and a low toxicity against the human body, and therefore, it is practically used based on these properties. However, the compound has a strong, characteristic, unpleasant smell. Thus, the compound gives rise to a difficulty in its application when used at a high concentration. Accordingly, the use of the compound is often limited to preservative and antimold purposes for wood stored outdoors.
Accordingly, the present inventors intended to develop compounds having a reduced smell together with a wide antimicrobial spectrum and a high antimicrobial activity.
DISCLOSURE OF THE INVENTION
In order to develop compounds having the above properties, the present inventors prepared a variety of iodopropargyl derivatives represented by the following formula (2): ##STR2## wherein R.sup.1 is an alkoxy group or a cyano group, and R.sup.2 is a hydrogen atom or a methyl group, and investigated their properties.
As a result, it was found that a particular iodopropargyl derivative has a reduced smell and also a wide antimicrobial spectrum and a high antimicrobial activity, and the present invention has been accomplished as follows.
The present invention provides iodopropargyl derivatives represented by the following formula (1): ##STR3## wherein R.sup.1 is a methoxy group or a cyano group.
Also, the present invention provides antimicrobial, antifungal and preservative or antimold agents comprising the iodopropargyl derivatives of the above formula (1) as an active ingredient.
BEST MODE FOR PRACTICING THE INVENTION
In the following, the present invention is described in more detail.
In the context of the present invention, the term "antimicrobial agent" means an agent having an effect on inhibition of proliferation of microorganisms such as bacteria, fungi and algae or on killing of these microorganisms.
The term "antifungal agent" means an agent having an effect on inhibition of proliferation of fungi or on killing of fungi.
The term "preservative or antimold agent" means an agent having an effect on inhibition of proliferation of rot-inducing microorganisms or decay fungi or on killing of these microorganisms.
Among the iodopropargyl derivatives of the formula (2), there are a group of compounds which have a reduced smell as well as a wide antimicrobial spectrum and a high antimicrobial activity, as shown in the Examples below.
From the viewpoint of the antimicrobial activity, preferable compounds are those of the formula (2) wherein R.sup.1 is a para-substituted methoxy or cyano group. More preferable compounds are those of the formula (2) wherein R.sup.1 is a para-substituted methoxy or cyano group and R.sup.1 is a hydrogen atom.
REFERENCES:
patent: 3660499 (1972-05-01), Kobayashi et al.
patent: 3923870 (1975-12-01), Singer
patent: 4487781 (1984-12-01), Morisawa et al.
Chikusa Yasuo
Moriwaki Masafumi
Ohnishi Toshimasa
Saijo Shigeya
Tanaka Ikuya
McKane Joseph
Nagase & Company, Ltd.
Nagase Chemicals Ltd.
Sackey Ebenezer
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