Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-05-11
1999-10-26
Stockton, Laura L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
514372, 548213, 548214, A01N 4380, C07D27503
Patent
active
059728434
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel acylated 5-aminoisothiazoles, processes for their preparation and their use for controlling animal pests.
It is already known that certain acylated 4-cyano-5-aminoisothiazoles have insecticidal properties (cf., for example, EP-A 0 623 282).
However, the activity and range of action of these compounds are not always completely satisfactory, especially when low amounts are applied and at low concentrations.
Novel acylated 5-aminoisothiazoles of the formula (I) ##STR2## in which R.sup.1 represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl or thiocarbamoyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl, cycloalkyl or optionally substituted cycloalkenyl and
It has furthermore been found that the acylated 5-aminoisothiazoles of the formula (I) are obtained by a process in which ##STR3## in which R.sup.1, R.sup.2 and R.sup.3 have the above-mentioned meaning, ##STR4## in which R.sup.1, R.sup.3, R.sup.4 and Y have the above-mentioned meaning, presence of a diluent and if appropriate in the presence of a catalyst, or presence of a diluent, ##STR5## in which R.sup.1, R.sup.4 and Y have the above-mentioned meaning and diluent.
Finally, it has been found that the novel acylated 5-aminoisothiazoles of the formula (I) have highly pronounced biological properties, and above all are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forestry, in the preservation of stored products and materials and in the hygiene sector.
The formula (I) provides a general definition of the acylated 5-aminoisothiazoles according to the invention.
Preferred substituents and ranges of the radicals listed in the formulae mentioned above and below are explained in the following. -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 or C.sub.1 -C.sub.4 -alkylthio, or represents C.sub.3 -C.sub.6 -cycloalkyl which is optionally substituted once to three times in an identical or different manner by C.sub.1 -C.sub.4 -alkyl or halogen. C.sub.1 -C.sub.4 -alkoxy-carbonyl, C.sub.2 -C.sub.4 -alkenyloxy-carbonyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -halogenoalkylsulfinyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 -halogenoalkylsulfonyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, or represents thiocarbamoyl. -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 -alkylsulfonyl or phenylcarbonyl, phenylsulfonyl or benzyl, in each case optionally substituted in the phenyl ring once to three times in an identical or different manner, possible substituents in each case being 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 substituted o
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Chem. Ber. vol. 97, Oct. 1964, Weinheim, pp. 3106-3117, Goerdeler J. et al., "Synthese von 5-amino-3-hydroxy(alkoxy-,amino-) isothiazo len und von Derivaten der Pyrimidinthione-(4)".
Indian J. Chem. vol. 16B, Sep. 1978, pp. 752-754, Rajappa, S. et al., "Synthesis of Thiophenes: Part VI --Synthesis of 2-Nitro-& 2,4-Dinitrothiophenes by direct Ring-closure Reactions".
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Erdelen Christoph
Heil Markus
Mencke Norbert
Turberg Andreas
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Stockton Laura L.
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