A sulfonic anhydride derivative from dibenzyl trisulphide with agro-chemical activities.
In the present study, the biologically active natural product dibenzyl trisulphide (DTS) which was previously isolated from the sub-tropical shrub Petiveria alliacea was transformed to methyl benzyl sulphonic anhydride (MBSA) using a "one pot" transformation method. The anhydride was evaluated for anti-microbial activities on the bacteria, Bacillus subtilis and Pseudomonas fluorescens and found to be 2.5 fold more effective than the commercial agents isoniazid and ampicillin in inhibiting the growth of B. subtilis, while on P. fluorescens it was 2.5, 5.0 and 10.0 fold more inhibitory than isoniazid, ampicillin and dibenzyl trisulphide, respectively. DTS was inactive on B. subtillis. The MIC value (microgram/spot) found for DTS on the plant pathogenic fungus, Cladosporium cucumerinum was 5.0 microgram/spot, while MBSA gave a value of 0.1 microgram/spot, compared with 1.25 and 0.16 microgram/spot for the commercial agents ketoconazole and nystatin, respectively. On the larval nematode (Meloidogyne incognita) MBSA inflicted 97.72% and 57.47% Abbotts nematicidal activities at 125.0 and 62.5 ppm, respectively, while DTS had no effect at 125.0 ppm. Nematodes which were immobilized by the low concentrations of MBSA were unable to re-activate when exposed to 10.0 ppm picrotoxin, thus suggesting that the anhydride nematicidal activity is independent of the GABA-ergic neurophysiological pathway.MBSA demonstrated a strong dose dependent radicular suppression effect (r=0.984), on the radicles of Latuca sativa germinating seeds. DTS was weakly active.
Williams
L A D
LA
Institute for Chemistry, University of Hohenheim, Garbenstr 30, D-70574, Stuttgart, Germany. ladwill@uni-hohenheim.de
Vasquez
E
E
Klaiber
I
I
Kraus
W
W
Rosner
H
H
D000818:Animals; D001412:Bacillus subtilis; D001593:Benzyl Compounds / Q000737:chemistry / Q000494:pharmacology*; D002963:Cladosporium; D007814:Larva; D009348:Nematoda; D010571:Pest Control; D011551:Pseudomonas fluorescens; D013440:Sulfides / Q000737:chemistry / Q000494:pharmacology*; D018675:Toxicity Tests
D001593:Benzyl Compounds; D013440:Sulfides; C474504:methyl benzyl sulfonic anhydride