Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-05-12
1996-12-10
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546323, C07D21381, A01N 4340
Patent
active
055831516
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT92/02556 filed Nov. 6, 1992.
The invention relates to new substituted pyridine-4-carboxamides, to a plurality of processes for their preparation, and to their use for the generation of resistance in plants against attack by undesired microorganisms.
It is known that certain pyridine-4-carboxylic acid derivatives can be used for generating resistance in plants against attack by phytopathogenic microorganisms (cf. EP-OS (European Published Specification) 0,268,775). 2,6-Dichloropyridine-4-carboxylic acid, methyl 2,6-dichloropyridine-4-carboxylate and .alpha.-(4-chlorophenyl)benzyl 2,6-dichloropyridine-4-carboxylate, for example, can be used for the abovementioned purpose. However, the activity of these substances is not always satisfactory, in particular when low application rates are used.
New substituted pyridine-4-carboxamides of the formula ##STR2## in which R.sup.1 represents hydrogen or alkyl, ##STR3## or -SO.sub.2 -R.sup.7, where R.sup.4 represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkoxy, optionally substituted alkanoyl or optionally substituted alkoxycarbonyl, substituted alkanoyl, optionally substituted aroyl, optionally substituted heteroarylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylsulphonyl or optionally substituted arylsulphonyl, or bonded represent an optionally substituted heterocycle, substituted alkenyl, optionally substituted alkinyl, optionally substituted alkanoyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl or optionally substituted heterocyclylcarbonyl, represent an optionally substituted five- or six-membered ring which can contain one or two hetero atoms, one or two keto groups and an SO.sub.2 group,
Depending on the nature of the substituents, the compounds of the formula (I) can exist in the form of geometric and/or optical isomers or variously composed isomer mixtures. The invention relates to the pure isomers and to the isomer mixtures.
Furthermore, it has been found that substituted pyridine-4-carboxamides of the formula (I) are obtained when ##STR4## in which
R.sup.1, X.sup.1 and X.sup.2 have the abovementioned meaning, are reacted with compounds of the formula ##STR5## in which
R.sup.2 and R.sup.3 have the abovementioned meaning and
E.sup.1 represents a suitable leaving group,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or ##STR6## in which
R.sup.1, X.sup.1 and X.sup.2 have the abovementioned meaning, are reacted with aldehydes of the formula ##STR7## in which
R.sup.2 has the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or ##STR8## in which
R.sup.1, R.sup.2, X.sup.1 and X.sup.2 have the abovementioned meaning, are reacted either
.alpha.) with carbinols or mercaptans of the formula
in which alkenyl, optionally substituted alkinyl, optionally substituted alkanoyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl or optionally substituted heterocyclylcarbonyl, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or
.beta.) with acid anhydrides of the formula ##STR9##
in which aryl or optionally substituted heterocyclyl,
or
.gamma.) with amines of the formula ##STR10##
in which
in which ##STR11## in which
R.sup.1, R.sup.2, X.sup.1 and X.sup.2 have the abovementioned meaning, are reacted with alcohols of the formula,
R.sup.10 represents alkyl,
in the presence of an oxidant and if appropriate in the presence of a diluent, or ##STR12## in which
X.sup.1 and X.sup.2 have the abovementioned meaning and
E.sup.2 represen
REFERENCES:
patent: 3398155 (1968-08-01), Horrom
Dehne Heinz-Wilhelm
Dutzmann Stefan
H anssler Gerd
Lunkenheimer Winfried
Schulz Uta
Bayer Aktiengesellschaft
Davis Zinna Northington
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