N-sulfonyliminodithio compounds useful for in plant and material

Details N-sulfonyliminodithio compounds useful for in plant and material N-sulfonyliminodithio compounds useful for in plant and material

1998-02-18

1999-07-20

O'Sullivan, Peter

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

504154, 504160, 514456, 558 2, 549366, A01N 4332, A01N 4106

Patent

active

059256753

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new N-sulphonyliminodithio compounds, processes for their preparation, and use in plant and material protection.
N-sulphonyliminodialkylthio compounds of similar structure which are biologically inactive have already been described (R. Gompper, H. Haigele; Chem. Ber. 99, 2885 (1966).
Structurally similar N-arylsulphonyliminodithio compounds are likewise known, a biological action is not described (M. Hans, H. Dehne, R. Hartwig; Z. Chem. 26, 204 (1986).
Further N-arylsulphonyliminothiocarboxylic acid diesters are described as herbicide safeners (EP 112 289).
Surprisingly, it has now been found that the new N-sulphonyliminodithio compounds of the general formula (I) ##STR2## in which R.sup.1 and R.sup.2 represent optionally substituted alkyl, alkenyl or alkinyl, and the protection of plants and materials. Additionally, new processes for the preparation of N-sulphonyliminodithio compounds of the formula (I) have been found.
Formula (I) provides a general definition of the new N-sulphonyliminodithio compounds according to the invention. Preferred compounds of the formula (I) are those in which or branched alkyl having 1 is 10 carbon atoms, straight-chain or branched alkenyl having 2 to 10 carbon atoms or straight-chain or branched alkinyl having 2 to 10 carbon atoms, which in each case are optionally mono- to polysubstituted identically or differently by halogen, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, acyl having 1 to 6 carbon atoms, acyloxy having 1 to 6 carbon atoms, (alkoxy)-carbonyl having 1 to 6 carbon atoms, amino which is optionally identically or differently substituted by alkyl or aryl, optionally in each case substituted phenoxy, aryl, pyridyl or pyridyloxy, nitro or cyano, and 10 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, alkoxy having 1 to 10 carbon atoms, halogenoalkoxy having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, alkylthio having 1 to 10 carbon atoms, halogenoalkylthio having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, amino, monoalkylamino with straight-chain or branched alkyl radicals having 1 to 6 carbon atoms, dialkylamino with identical or different, straight-chain or branched alkyl radicals each having 1 to 6 carbon atoms, cycloalkyl having 1 to 6 carbon atoms, methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, nitro or cyano.
Particularly preferred compounds of the formula (I) are those in which or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms or straight-chain or branched alkinyl having 2 to 8 carbon atoms, which in each case are optionally mono- to tetrasubstituted identically or differently by fluorine, chlorine, alkoxy having 1 to 5 carbon atoms, halogenoalkoxy having 1 to 5 carbon atoms and 1 to 5 fluorine and/or chlorine atoms, alylthio having 1 to 5 carbon atoms, halogenoalkylthio having 1 to 5 carbon atoms and 1 to 5 fluorine and/or chlorine atoms, acyl having 1 to 5 carbon atoms, acyloxy having 1 to 5 carbon atoms, alkoxycarbonyl having 1 to 5 carbon atoms, amino which is optionally identically or differently substituted by alkyl having 1 to 4 carbon atoms and/or phenyl, optionally in each case substituted phenoxy, aryl, pyridyl or pyridyloxy, nitro or cyano, and fluorine, chlorine, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 6 fluorine and/or chlorine atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 6 fluorine and/or chlorine atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 6 fluorine and/or chlorine atoms, amino, monoalkylamino with alkyl radicals of 1 to 4 carbon atoms, dialkylamino with identi

REFERENCES:
patent: 3322788 (1967-05-01), Gompper et al.
Zeitschrift Fur Chemie, vol., 26, No. 6, Jun. 1986, Leipzig, DE pp. 204-205.
Chemische Bedrichte, vol. 99m No. 9, Sep. 1, 1966, Weinheim, DE, pp. 2885-2899.
Chemische Bedrichte, vol. 99m No. 9, Sep. 1, 1966, Weinheim, DE, pp. 2900-2904.

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