Four pure isothiocyanates (methyl, 2-propenyl, benzyl and 2-phenylethyl isothiocyanate), hydrolysing tissue of two brassicas rich in either 2-propenyl or 2-phenylethyl isothiocyanate, and the methyl isothiocyanate-generating pesticide metam-sodium were tested in vapour exposure tests for biological activity against a model soil insect both in vitro and in the presence of three contrasting soils and under four temperatures from 5 to 20 degrees C. The purpose was to develop an understanding of the factors controlling isothiocyanate release and maintenance in soil in order to identify advantageous attributes to seek in utilising brassicas for isothiocyanate-based biofumigation. Methyl isothiocyanate, structurally the simplest and the most volatile, was the most biologically active isothiocyanate under all conditions. It was less affected by the presence of soil and by lower temperature than the longer-chain aliphatic 2-propenyl isothiocyanate. The activity of the less volatile aromatic isothiocyanates was reduced much more by soil, with a decline up to many thousand-fold in the presence of soil with high organic matter content at lower temperature. Metam-sodium closely reflected the methyl isothiocyanate results. The results indicate that brassicas rich in aliphatic isothiocyanates are more likely to have the potential to exert stronger isothiocyanate-based biofumigation effects than those similarly rich in aromatic isothiocyanates.
A total of 570 lyophilised Brassica root and shoot tissue samples were hydrolyzed, and the liberated isothiocyanates (ITCs) were analyzed by gas chromatography-flame photometric detection (GC-FPD). Glucosinolates (GSLs) were extracted from samples of the same tissues and analyzed by high-performance liquid chromatography (HPLC). The concentrations of six GSLs/ITCs (2-propenyl, 3-butyl, 4-pentenyl, benzyl, 4-methylthiobutyl, and 2-phenylethyl) as determined by the two techniques were compared. In 79% of the samples, the concentration of GSLs in the tissues was greater than that of the ITCs released on hydrolysis. Several possible reasons for the difference are proposed, including the effect of tissue storage time, hydrolysis of GSLs may be less efficient than the GSL extraction procedure, or some of the ITCs formed reacted with plant proteins and amino acids in the sample and were therefore not detected in the extract. GSL concentration in plant tissues is used to estimate the biofumigation potential of the plant tissue, whereas the actual biofumigation effect is thought to be due to the ITCs formed by hydrolysis of the plant-based GSLs. The variation between ITC and GSL values therefore has implications for the assessment of the biofumigation potential of the plant tissue.
First instars of the soil-inhabiting whitefringed weevil, Naupactus leucoloma (Boheman), are a particularly good bioassay model for assessing volatile soil fumigants and biofumigants. Eggs are readily obtained and can be stored for long periods with larvae hatched on demand and the first instar is non-feeding, surviving without food or shelter. Longevity varies with temperature, but readily accommodates the period required to conduct bioassays without appreciable mortality of untreated controls. In vitro bioassays of pure methyl isothiocyanate, the active ingredient from metham sodium soil fumigant, and the less volatile 2-phenylethyl isothiocyanate, sensitively detected differences in toxicity and effects of temperature. Bioassay of volatiles emitted from hydrolysed tissue of various isothiocyanate-producing Brassica plants revealed widely varying toxicity effects, indicating that bioassays with N. leucoloma are a sensitive and relevant indicator of the potential of different plants for biofumigation of soil-borne pest organisms.
Enhanced biodegradation of methyl isothiocyanate (MITC), the toxin produced by the broad-spectrum biocide metham sodium, substantially reduced its toxicity to whitefringed weevil, Naupactus leucoloma (Boheman), in laboratory tests using metham sodium-treated field soils. A level of enhanced biodegradation in a highly degrading soil that reduced MITC production and persistence to approximately 10% of that in a mildly degrading soil caused a doubling of the LC 90 . Given the very high acute toxicity of MITC, this superficially limited effect in reality demonstrates the dramatic impact that severe levels of enhanced biodegradation can have in reducing the efficacy of metham sodium for control of soil-borne pests and diseases.
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