Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-11-19
1999-08-31
Fan, Jane
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504248, 5462704, 546193, A01N 4340, C07D40140
Patent
active
059453800
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new pyridyl-thiazoles, several processes for their preparation and their use for protecting plants against attack by undesirable microorganisms.
It has already been disclosed that certain halogenopyridine-4-carboxylic acid derivatives can be employed for generating resistance in plants against attack by phytopathogenic microorganisms (cf. EP-OS (European Published Specification) 0 268 775 and DE-OS (German Published Specification) 4 138 026). Thus, for example, 2,6-dichloropyridine-4-carboxylic acid, methyl 2,6-dichloropyridine-4-carboxylate and .alpha.-(4-chlorophenyl)-benzyl 2,6-dichloropyridine-4-carboxylate can be used for the purpose mentioned. However, the action of these substances is not always satisfactory, above all when low amounts are applied. Furthermore, the direct fungicidal action of these compounds leaves something to be desired.
New pyridyl-thiazoles of the formula ##STR3## in which R represents alkyl, ##STR4## wherein R.sup.1 represents hydrogen or --CO--R.sup.5, alkoxycarbonyl, alkylamino, optionally substituted aryl, optionally substituted arylamino or optionally substituted arylsulphonylamino, or bonded, represent a cyclic imide of the formula ##STR5## wherein A represents optionally substituted alkanediyl or optionally substituted alkenediyl,
It has furthermore been found that pyridyl-thiazoles of the formula (I) and salts and acid adducts thereof are obtained by a process in which ##STR6## in which X.sup.1 and X.sup.2 have the abovementioned meanings and ##STR7## in which R has the abovementioned meaning, presence of an acid-binding agent, or ##STR8## in which X.sup.1 and X.sup.2 have the abovementioned meanings, ##STR9## in which R.sup.5 has the abovementioned meaning or ##STR10## in which A has the abovementioned meaning, or ##STR11## in which R.sup.5 has the abovementioned meaning and substituted arylsulphonyl, or ##STR12## in which R.sup.3 and R.sup.4 have the abovementioned meanings and of a catalyst and if appropriate in the presence of an acid-binding agent, then reacted with an acid or base.
Finally, it has been found that the pyridyl-thiazoles of the formula (I) and salts and acid adducts thereof can be used particularly suitably for protecting plants against attack by undesirable microorganisms. The substances according to the invention are suitable both for generating resistance in plants against attack by undesirable microorganisms and as microbicides for combating the microorganisms directly.
Surprisingly, the substances according to the invention are more suitable for generating resistance in plants against attack by phytopathogenic microorganisms than 2,6-dichloro-pyridine-4-carboxylic acid, methyl 2,6-dichloro-pyridine-4-carboxylate and .alpha.-(4-chlorophenyl)-benzyl 2,6-dichloro-pyridine-4-carboxylate, which are structurally similar compounds which are already known from the prior art and have the same type of action. Furthermore, the substances according to the invention surprisingly are also superior in respect of their fungicidal activity to the substances already described which are structurally the most similar.
Where appropriate, the substances according to the invention can be in the form of mixtures of various possible isomeric forms, such as, for example, in the form of stereoisomers or tautomers. The invention relates both to stereoisomers and to tautomers, and also to any desired mixtures of these isomers.
Formula (I) provides a general definition of the pyridyl-thiazoles according to the invention. carbon atoms or the groups ##STR13## R.sup.1 also preferably represents hydrogen or --CO--R.sup.5. R.sup.2 also preferably represents hydrogen or --CO--R.sup.6. having 1 to 4 carbon atoms. dialkylamino having 1 to 4 carbon atoms in each alkyl group. straight-chain or branched alkyl having 1 to 6 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group, alkylamino having 1 to 6 carbon atoms, aryl having 6 to 10 carbon atoms, arylamino having 6 to 10 carbon atoms or arylsulphonylamino having 6 to 10 carbon ato
REFERENCES:
CA 117:131190, Pilkington, 1992.
CA 87 : 135172, Le Count et al. 1977.
Dehne Heinz-Wilhelm
Dutzmann Stefan
Gallenkamp Bernd
Hanssler Gerd
Stenzel Klaus
Bayer Aktiengesellschaft
Fan Jane
LandOfFree
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