The use of allelopathic cover crops in reduced tillage cropping systems may provide an ecologically sound and environmentally safe management strategy for weed control. Growers often plant winter rye (Secale cereale L.) for increased soil organic matter and soil protection. Spring-planted living rye reduced weed biomass by 93% over plots without rye. Residues of fall-planted/spring-killed rye reduced total weed biomass over bare-ground controls. Rye residues also reduced total weed biomass by 63% when poplar excelsior was used as a control for the mulch effect, suggesting that allelopathy, in addition to the physical effects of the mulch, did contribute to weed control in these systems. In greenhouse studies, rye root leachates reduced tomato dry weight by 25-30%, which is additional evidence that rye is allelopathic to other plant species.

A variety of crops, cultivars, and accessions have been evaluated over the past six years for superior capability to suppress weed growth. The most successful of these approaches has been to grow cover crops of rye (Secale cereale), wheat (Triticum aestivum), sorghum (Sorghum bicolor), or barley (Hordeum vulgare) to a height of 40-50 cm, desiccate the crops by contact herbicides or freezing, and allow their residues to remain on the soil surface. Often, up to 95% control of important agroecosystem weed species was obtained for a 30- to 60-day period following desiccation of the cover crop. The plant residues on the soil surface exhibit numerous physical and chemical attributes that contribute to weed suppression. Physical aspects include shading and reduced soil temperatures which were similarly achieved using poplar (Populus) excelsior as a control mulch. Chemical aspects apparently include direct release of toxins, as well as production of phytotoxic microbial products. Numerous chemicals appear to work in concert or in an additive or synergistic manner to reduce weed germination and growth.

Two phytotoxic compounds [2,4-dihydroxy-1,4(2H)-benzoxazin-3-one (DIBOA) and 2(3H)-benzoxazolinone (BOA)] were previously isolated and identified in 35-day-old greenhouse-grown rye shoot tissue. Both compounds were also detected by TLC in greenhouse-grown root and fieldgrown shoot tissue. The concentration of DIBOA varied in the tissues, with the greatest quantity detected in greenhouse-grown shoots. DIBOA and BOA were compared with β-phenyllactic acid (PLA) and β-hydroxybutyric acid (HBA) for activity on seed germination and seedling growth and were consistently more toxic than either compound. Dicot species tested, including lettuce (Lactuca sativa L.), tomato (Lycopersicon esculentum Mill.), and redroot pigweed (Amaranthus retroflexus L.), were 30% more sensitive than the monocots tested. Of the two benzoxazinone compounds, DIBOA was most toxic to seedling growth. DIBOA and BOA reduced chlorophyll production inChlamydomonas rheinhardtii Dangeard, by 50% at 7.5 × 10(-5) M and 1.0 × 10(-3) M, respectively. Both DIBOA and BOA inhibited emergence of barnyardgrass (Echinochloa crusgalli L. Beauv.), cress (Lepidium sativum L.), and lettuce when applied to soil, indicating their potential for allelopathic activity.

Under simulated no-till conditions in the greenhouse, rye (Secale cereale L. ‘Wheeler’) residues reduced emergence of lettuce (Lactuca sativa L. ‘Ithaca’) and proso millet (Panicum miliaceum L. # PANMI) by 58 and 35%, respectively, over that obtained with a wood shaving control mulch. Rye shoot tissue inhibited lettuce germination 52% more than root tissue. Petri dish bioassays of residue in soil confirmed phytotoxicity on cress (Lepidium sativum L. ‘Curly’), lettuce, barnyardgrass (Echinochloa crus-galli L. Beauv. # ECHCG), and proso millet. Radicle elongation was a more senstive measure of phytotoxicity than germination per se. Phytotoxicity increased as the distance from seeds to rye residues decreased. While rye shoot residues caused 40% greater inhibition of cress radicle elongation in sterile soil than nonsterile soil, barnyardgrass was equally inhibited in both soil regimes. Phytotoxicity decreased in nonsterile soil, indicating that the compounds were degraded by microorganisms. Phytotoxic compounds in shoots were water extractable. Cress and barnyardgrass responded similarly to both aqueous rye extracts and to residues added to soil.

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The metabolism of cycloate, a thiocarbamate herbicide, was investigated in mature radish leaf. Twelve new metabolites were identified by liquid chromatographic/mass spectrometric analysis using fast atom bombardment and packed capillary liquid chromatography columns. Full-scan and tandem mass spectrometric methods were employed. Application of the on-column focusing technique resulted in identifications with injections of as little as 15 ng of metabolite (20 ppb in radish). This injection technique allows the practical use of packed capillary liquid chromatography/mass spectrometry in sample-limited applications. Cycloate is oxidized to several ring-hydroxylated isomers that are subsequently glucosylated and esterified with malonic acid. Cycloate is also conjugated with glutathione. Metabolic hydrolysis of the glutathione conjugate formed a cysteine conjugate that is further metabolized by amidation with either malonic or acetic acid. Transamination of the cysteine conjugate gave a thiolactic acid derivative. Metabolites were also identified that were the result of both ring-hydroxylation and conjugation with glutathione. One of these, an N-acetylcysteine conjugate, is the first report of a mercapturic acid in plants. The structures of two of the new metabolites were confirmed by chemical synthesis.