Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-07-01
1998-09-22
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514542, 558390, A61K 31535, C07C25503
Patent
active
058114246
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/01846 filed on Nov. 1, 1994.
FIELD OF THE INVENTION
The present invention relates to novel amino-acid amide derivatives as well as to agricultural or horticultural fungicides containing the same as active ingredients.
BACKGROUND ART
Heretofore, it is known that the amino-acid amide derivatives such as N.sup.2 -tert-butoxycarbonyl-N.sup.1 -(2-phenoxyethyl)-D-alanine and N.sup.2 -tert-butoxycarbonyl-N.sup.1 -(2-phenylthioethyl)-D-alanine (Japanese Patent Application, First Publication, No. Sho 62-89696) are intermediates for medicines; however, the utility of the amino-acid amide derivatives are not known. In addition, it is known that the amino-acid amide derivatives such as N-(tert-butoxycarbonyl)-L-valine-1-(4-methylphenyl)ethylamide (Japanese Patent Application, First Publication, No. Hei 3-5451), N.sup.2 (Japanese Patent Application, First Publication, No. Hei 3-153657), and the like are useful for biocides.
However, the fungicidal activities of fungicides may become degraded because of the emergence of resistant fungi after repeated uses of the fungicides. For this reason, as well as because of environmental problems, it is desired to provide a novel fungicide which can efficiently control harmful fungi even at a low concentration.
DISCLOSURE OF THE INVENTION
In order to develop a fungicide possessing fungicidal activity superior to that of known fungicides, the present inventors have synthesized various amino-acid amide derivatives and have carried out extensive research in connection with their effects on the biological activities of fungi. As a result, we have found that the compounds according to the present invention, possessing a substituted or non-substituted phenoxy group, a substituted or non-substituted benzyloxy group, a substituted or non-substituted alkoxy group, and the like, as a terminal group, exhibit a broad spectrum of anti-fungal activity especially against cucumber downy mildew, grape downy mildew, and tomato late blight in small amounts, while at the same time do not hinder desirable plant growth.
According to an aspect of the present invention, there is provided ##STR2##
wherein R.sup.1 represents
(a) a lower alkyl group (optionally having at least one same or different substituent selected from the group consisting of a halogen atom, an alkoxy group, and a cyano group),
(b) a lower alkenyl group,
(c) a lower alkynyl group,
(d) a cycloalkyl group (optionally having at least one substituent selected from the group consisting of methyl group and a halogen atom),
(e) a cycloalkylalkyl group,
(f) a cycloalkenyl group,
(g) a cyclic ether group,
(h) a phenyl group (optionally having at least one same or different substituent selected from the group consisting of halogen atom, halogen atom,
(i) an aralkyl group (optionally having at least one same or different substituent selected from the group consisting of a methyl group, a cyano group, and a nitro group), or
(j) a heterocyclic group,
R.sup.2 represents a lower alkyl group, a lower alkenyl group, a cycloalkyl group, or a phenyl group (optionally having at least one substituent of halogen atom),
R.sup.3 represents a hydrogen atom or a lower alkyl group,
R.sup.4 represents a hydrogen atom, a lower alkyl group, or a cyano group,
R.sup.5, R.sup.6, and R.sup.7 independently represent a hydrogen atom or a lower alkyl group,
R.sup.8 represents a hydrogen atom, a lower alkyl group, an aralkyl group, a phenyl group, an alkoxycarbonyl group, or a cyano group,
Z.sup.1 and Z.sup.2 independently represent an oxygen atom or a sulfur atom,
Z.sup.3 represents
an oxygen atom,
a sulfur atom,
a group ##STR3## (wherein R.sup.10 represents a hydrogen atom, a methyl group, an acetyl group, a benzoyl group, a methoxycarbonyl group, or a methoxymethyl group),
a sulfinyl group,
a sulfonyl group,
a group --C(O)O--,
a group ##STR4## (wherein R.sup.11 represents a hydrogen atom or a lower alkyl group),
Q represents substituent selected from the group consisting of
a lower alkyl group which may be substituted with a
REFERENCES:
patent: 5574064 (1996-11-01), Shibata et al.
Hayashi Shigeru
Kojima Yoshiyuki
Sakai Jun-etsu
Shibata Masaru
Sugiyama Kazuhiko
Ihara Chemical Industry Co. Ltd.
Kumiai Chemical Industry Co. Ltd.
Richter Johann
Sackey Ebenezer O.
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