Amino acid derivatives and their use as pesticides

Details Amino acid derivatives and their use as pesticides Amino acid derivatives and their use as pesticides

1996-12-20

1998-09-29

Kumar, Shailendra

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

514456, 549407, 564194, 564196, A61K 31165, C07C23305, C07C23110

Patent

active

058146695

DESCRIPTION:

BRIEF SUMMARY
The invention relates novel amino acid derivatives, to a process for their preparation and to their use as pesticides, in particular as fungicides, and as intermediates for preparing known substituted amino acid derivatives with fungicidal activity.
It is already known that certain substituted amino acid derivatives have fungicidal properties and are obtained by reacting substituted amino acids with appropriate amines (compare EP-A 0 472 995).
Furthermore, certain amines of substituted amino acids are known (compare EP-A 0 587 110).
Novel compounds of the general formula (I) ##STR1## in which A represents straight-chain or branched alkylene or substituted heterocyclyl, and now been found, excepting the compounds N.sup.1
Aryl preferably represents hereinafter in each case unsubstituted or substituted phenyl, benzothiophene, benzofuran, suitable and preferred substituents being halogen, cyano, alkyl, halogenoalkyl, alkoxy and halogenoalkoxy.
Alkyl preferably represents hereinafter straight-chain or branched alkyl with 1 to 6, in particular 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, n-, i-, t-butyl and, in particular, i-propyl and s-butyl and represents cyclic alkyl with 3 to 6 carbon atoms such as, in particular, cyclopentyl.
Alkylene preferably represents hereinafter straight-chain or branched alkylene with 1 to 6, preferably 1-4 carbon atoms such as, in particular 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1-methyl-1,2-ethylene, 2-methyl-1,2-ethylene, 1,1-dimethyl-methylene.
Preferred compounds are those of the formula (I) ##STR2## in which A represents 1,1-ethylene or 1,2-ethylene, benzothiophene or benzofuran, substituents which are mentioned being halogen, cyano, alkyl, halogenoalkyl, alkoxy and halogenoalkoxy, and
Particularly preferred compounds are those of the formula (I) in which substituted in the phenyl ring once to three times by methyl, methoxy, trifluoromethyl, trifluoromethoxy, ethyl, ethoxy, fluorine, chlorine and/or cyano, and
Very particularly preferred compounds are those of the formula (Ia) ##STR3## in which R.sup.1 represents chlorine, methyl, ethyl or methoxy, and their salts.
The compounds of the formula (I) contain two centres of chirality and may thus exist in various enantiomeric and diastereomeric mixtures which can, where appropriate, be separated in a conventional way. Both the pure enantiomers and diastereomers and the mixtures are claimed according to the invention.
For the sake of simplicity reference will always be made hereinafter to compounds of the formula (I) although both the pure compounds and the mixtures with various contents of isomeric, enantiomeric and diastereomeric compounds are meant.
A corresponding statement applies to the compounds of the formulae (III) and (IV) which also follow.
It has furthermore been found that the compounds of the formula (I) ##STR4## in which A represents straight-chain or branched alkylene or substituted heterocyclyl, and oxazolidinediones of the formula (II) ##STR5## in which R has the abovementioned meaning, where appropriate, in the presence of a reaction aid.
It has additionally been found that the novel amino acid derivatives of the formula (I) can be used as pesticides.
Preferred compounds of the formula (I) are those in which the underlying amino acid is the compound with the L configuration, and the amine of the formula (III) which is employed is either racemic or has the R configuration or the S configuration at the asymmetric carbon atom.
The oxazolidinediones of the formula (II) to be used as starting material for carrying out the process according to the invention are known (compare Angew. Chem. 93, 793 (1981)) and can be obtained by the process described therein, by reacting the appropriate amino acids with phosgene in a conventional way.
The amines which are additionally to be used as starting materials for carrying out the process according to the invention are generally defined by formula (III).
The amines of the formula (III) are generally known compounds of organic chemistry.
Diluents suitable for the proce

REFERENCES:
patent: 4918105 (1990-04-01), Cartwiright et al.

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