Amino-acid amide derivatives, processes for preparing the same,

Details Amino-acid amide derivatives, processes for preparing the same, Amino-acid amide derivatives, processes for preparing the same,

1997-02-03

1998-08-04

Powers, Fiona T.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514375, 514394, 548178, 548180, 548217, 5483097, A01N 4352, A01N 4376, A01N 4378, C07D23516, C07D26356

Patent

active

057894280

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to novel amino-acid amide derivatives and to processes for their preparation. The present invention also relates to agricultural or horticultural fungicides containing the same as active ingredients and to a method for killing fungi.


BACKGROUND ART

Heretofore, it is known that amino-acid amide derivatives, such as, for -phenoxycarbonyl-L-valinamide are useful as biocides (Japanese Patent Application, First Publication, No. Hei 3-153657). In addition, it is also known that amino-acid amide derivatives, such as, for example, N.sup.1 N.sup.2 -tert-butoxycarbonyl-N.sup.1 (European Patent No. 587110).
However, the fungicidal activities of fungicides may decrease because of the emergence of resistant fungi after repeated use of the fungicides. For this reason, as well as because of environmental problems, it is desired to provide novel fungicides which can efficiently control harmful fungi even at low concentrations.


DISCLOSURE OF THE INVENTION

In order to develop fungicides possessing fungicidal activities superior to those 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 physiological activities of fungi. As a result, we have found that the compounds according to the present invention, possessing a benzothiazole ring, a benzoxazole ring, or a benzimidazole ring bonded to an amine moiety, exhibit a broad spectrum of anti-fungal activity at low dose especially against tomato late blight, potato late blight, grape downy mildew, and cucumber downy mildew, while at the same time do not hinder desirable plant growth.
According to aspects of the present invention, there are provided
(1) an amino-acid amide derivative represented by the formula: ##STR2##
wherein R.sup.1 represents a C1.about.C6 alkyl group, a C3.about.C8 cycloalkyl group, a phenyl group (optionally having at least one same or different halogen atom substituent), or a benzyl group,
R.sup.2 represents a hydrogen atom or a methyl group,
X represents a halogen atom, a methyl group, a methoxy group, a methylthio group, a cyano group, or a trifluoromethyl group,
Y represents a C1.about.C6 alkyl group,
A represents an oxygen atom, a sulfur atom, or a group of the formula: ##STR3## (wherein R.sup.3 represents a hydrogen atom, a C1.about.C6 alkyl group, a C1.about.C6 alkoxymethyl group, or an acyl group), and
n represents 0 or an integer from 1 to 3,
(2) a process for preparing an amino-acid amide derivative represented by the formula: ##STR4##
(wherein R.sup.1, R.sup.2, X, Y, A, and n have the same meanings as defined in (1)), the formula: ##STR5##
(wherein R.sup.1 and Y have the same meanings as defined above), or the amino-acid amide derivative possessing an activated carboxyl group, with an amine represented by the formula: ##STR6##
(wherein R.sup.2, X, A, and n have the same meanings as defined above),
(3) a process for preparing an amino-acid amide derivative represented by the formula: ##STR7##
(wherein R.sup.1, R.sup.2, X, Y, A, and n have the same meanings as defined above), ##STR8## (wherein Z represents a halogen atom or a group of the formula: R.sup.1 OC(O)O--, R.sup.1 has the same meaning as defined above), with an amine represented by a formula: ##STR9##
(wherein R.sup.2, X, Y, A, and n have the same meanings as defined above), acid salt thereof including a tosylate in the presence of a base if necessary,
(4) an agricultural or horticultural fungicide including the amino-acid amide derivative as defined above as an active ingredient, and
(5) a method for killing agriculturally or horticulturally harmful fungi which comprises a step of using a fungicidally effective amount of an amino-acid amide derivative as defined above.
The terms employed in this specification of the present invention are defined as follows.
The term "alkyl group" is used herein to mean a straight or branched alkyl group possessing 1 to 6 carbon atoms including, but not limited to, a methyl g

REFERENCES:
patent: 5158962 (1992-10-01), Seitz et al.
patent: 5395824 (1995-03-01), Higuchi et al.
patent: 5428167 (1995-06-01), Wissner et al.
patent: 5430150 (1995-07-01), Trova et al.
Maekawa et al., Agric. Biol. Chem., 41 (5), 811-818, 1977.
Maekawa et al., Chemical Abstracts, 87:202070, 1977.
Vermehren et al., Chemical Abstracts, 122:133844, 1995.

Affiliated with

Also associated with

Rating

Amino-acid amide derivatives, processes for preparing the same, does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Amino-acid amide derivatives, processes for preparing the same, , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amino-acid amide derivatives, processes for preparing the same, will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1177562