Hydrolysis and photolysis of the fungicide triforine

Abstract

The main decomposition products formed from triforine by hydrolysis in solution and by photolysis were isolated and identified. In aqueous solution at 21°, hydrolysis proceeds rapidly by formation of chloride ions and, through several intermediates, 1‐(dihydroxyacetyl)piperazine and piperazine. Photolysis by ultraviolet light in the absence of water leads preferentially to the removal of one side chain, the second side chain being attacked more slowly. In aqueous solution, triforine is rapidly destroyed by ultraviolet light. N‐(2,2‐Dichlorovinyl)formamide was isolated as an intermediate photodecomposition product.

Resistance to triforine: A nonexistent problem?

“…With this fungicide, a remarkable molecular endurance in plants (Fuchs and Ost, 1976;) is accompanied by a half-life in dilute aqueous solutions of only two to three days (Fuchs and Ost, 1976;Darda et al, 1977).…”

Absorption, metabolism and excretion of the fungicide triforine in the rat

“…The more hydrophilic metabolite M i was rather more rapidly excreted than Mz. The ratio M1 : hlz in the urine of the 0-10 h interval was 56 : 37; in the total urine during the S. Darda (1) Front 0-24 h period however it was 32 : 68. Disregarding the minor metabolites, it can be estimated that 36% of the ["Cl-dose administered was excreted renally as [14C]-Mz and 17% as [14C]-M1 within 24 h. The metabolite M2 will be referred to hereafter as the major urinary metabolite of triforine.…”