Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides

Details Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides

1998-06-30

1999-08-24

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548128, C07D28508, A01N 4382

Patent

active

059425288

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel acylated 5-amino-1,2,4-thiadiazoles, a process for their preparation, and to their use for controlling animal pests and as fungicides.
It is already known that certain acylated 4-cyano-5-aminoisothiazoles have insecticidal properties (cf. for example EP-A-0 623 282).
However, the potency and persistency of these prior-art compounds is not always entirely satisfactory, in particular at low application rates and concentrations.
The invention provides novel acylated 5-amino-1,2,4-thiadiazoles of the formula (I) ##STR2## in which R.sup.1 represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, alkylcarbonyl, alkylsulphonyl, respectively optionally substituted arylcarbonyl, arylsulphonyl or arylalkyl or optionally substituted cycloalkyl, cycloalkyl or optionally substituted cycloalkenyl and
Furthermore, it has been found that the acylated 5-amino-1,2,4-thiadiazoles of the formula (I) are obtained when ##STR3## in which R.sup.1 and R.sup.2 each have the meanings stated above are reacted with acid halides of the formula (III)
Finally, it has been found that the novel acylated 5-amino-1,2,4-thiadiazoles of the formula (I) have pronounced biological properties and are especially suitable as fungicides and for controlling animal pests, in particular insects, arachnids and nematodes encountered in agriculture, in forestry, in the protection of stored products and materials, and in the hygiene sector.
Formula (I) provides a general definition of the acylated 5-amino-1,2,4-thiadiazoles according to the invention.
Preferred substituents or ranges of the radicals mentioned in the formulae given hereinabove and hereinbelow will now be illustrated. -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.3 -C.sub.6 -cycloalkyl which is optionally mono- to trisubstituted by identical or different C.sub.1 -C.sub.4 -alkyl or halogen substituents, -C.sub.4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl-carbonyl, C.sub.1 -C.sub.4 -alkylsulphonyl, phenylcarbonyl, phenylsulphonyl or benzyl, each of which is optionally mono- to trisubstituted on the phenyl ring by identical or different substituents from the group consisting of halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.2 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.2 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or C.sub.1 -C.sub.2 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or represents C.sub.3 -C.sub.6 -cycloalkyl which is optionally mono- to trisubstituted by identical or different C.sub.1 -C.sub.4 -alkyl or halogen substituents, trisubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.12 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.12 -alkylthio, C.sub.1 -C.sub.12 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -halogenoalkenyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.3 -C.sub.8 -cycloalkyl which is optionally mono- to trisubstituted by identical or different C.sub.1 -C.sub.4 -alkyl or halogen subst

REFERENCES:
patent: 5705650 (1998-01-01), Tatsuta

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