Distribution of the carcinogenic terpene ptaquiloside in bracken fronds,rhizomes (Pteridium aquilinum), and litter in Denmark

The distribution of ptaquiloside (PTA) was studied in four Danish bracken populations in order to evaluate the transfer of PTA from ferns to soil. Populations showed statistically significant differences in PTA contents of fronds and rhizomes despite large in-site variations. The highest concentrations were encountered in fronds with concentrations ranging between 213 and 2145 g/g, while rhizomes had concentrations between 11 and 902 g/g. PTA was present in soil materials in amounts of 0.22–8.49 g/g but apparently with no correlation with PTA contents of fronds or rhizomes. Laboratory tests showed that water could leach PTA from bracken fronds, which is in support of the high soil contents observed at sites exposed to heavy showers just before sampling. The observed soil contents correspond to estimated soil solution concentrations of 200–8500 g/liter, demonstrating a substantial risk of PTA contamination of surface water and groundwater.     

Seasonal variation in phytotoxicity of bracken (Pteridium aquilinum L. Kuhn)

Laboratory bioassays were used to test for the phytotoxicity of volatile compounds, fresh plant material as a seed bed, and water extracts from bracken [Pteridium aquilinum (L.) Kuhn] pinnules to germination and seedling growth of aspen (Populus tremula L.) and Scots pine (Pinus sylvestris L.). Fronds were sampled from two bracken populations, one in the south and one in the north of Sweden. All three bioassays showed inhibitory effects, and these varied seasonally with the most inhibitory effects occurring in May, June, and September. The peak of inhibition in May and June coincides with the start of the growing season when bracken still is immature and vulnerable to interference from other species. The increase in inhibitory effects in September appears to be due to transformation of natural products or an accumulation of inhibitory compounds that are released during decomposition following frond death. Addition of activated carbon did not remove the inhibitory effects.     

The role of phytoecdysteroids in bracken fern,Pteridium aquilinum (L.) Kuhn as a defense against phytophagous insect attack

Analysis of green bracken fronds collected during July, August, and October, 1975, for phytoecdysteroids showed that these compounds occur in only trace amounts (0.25–0.53 g/kg fresh weight [FW]). The effect of ecdysteroids on the feeding behavior of seven species of insect showed that four species were deterred at ecdysteroid concentrations at or above 60 mg/kg FW diet; one species of insect at 6 mg/kg or above, and two species which were not affected at the higher concentrations. It was concluded that the levels of phytoecdysteroids in bracken would not deter insects from feeding on the plant. The previously published data relevant to the possible role of phytoecdysteroids as defense compounds are also discussed.     

Ontogenic variation of biologically active metabolites ofPteridium aquilinum (L. Kuhn) pterosins A and B,and ptaquiloside in a bracken population of the tropical andes

A negative correlation has been found between the amounts of pterosins A and B and ptaquiloside per biomass unit, and the growth stage of the blade of bracken. Their concentration decreased progressively from the crozierto the mature frond, where it attained less than 5% of the initial value. The growth was measured following the total blade length, its height, moisture content, and time of emergence from the soil surface. Quantitation of these compounds was achieved by HPLC using a water extraction, methylene chloride treatment, and silica gel microcolumn cleanup sequence. Pterosins were unevenly distributed in the blade, whereas ptaquiloside maintained a constant concentration throughout. Rhizomes contained only minor amounts of these compounds. Their possible role as semiochemicals in bracken is discussed.     

Assessment of allelopathic potential inArtemisia princeps var.Orientalis residues

Field and laboratory studies were conducted to examine the differential phytotoxicity of residues ofArtemisia princeps var.orientalis (wormwood) using various plants as test species. Seedling elongation and dry weights of receptor plants were inversely proportional to the concentration and incubation time of dry leaves ofA. princeps var.orientalis in vermiculite. In seedling growth tests with abandoned field soils (control) and soil underneath wormwood plants (test), the elongation, dry weight, and caloric content of seedlings grown in the soil from under wormwood plants were severely inhibited, thereby suggesting that certain growth inhibitors were released from wormwood and the inhibitor remained in the soil.     

Role of allelopathy as a possible factor associated with the rising dominance ofBunias orientalis L. (Brassicaceae) in some native plant assemblages

Leaf extracts ofBunias orientalis were shown to inhibit seed germination of a variety of cultivar plant species and of species cooccurring withB. orientalis in the field. Root exudate solutions and leaf litter leachates ofB. orientalis were tested for their allelopathic activity using seedling growth assays. Additionally, in comparative seedling growth assays soil cores removed from denseB. orientalis stands were tested bimonthly for elevated allelopathic effects. The impact of root exudates on seedling growth was generally weak and varied between species. Similar results were obtained for the effect ofB. orientalis leaf litter leachates on seedlings grown in sand culture relative to the effect of leaf litter leachates of a plant species mixture. When soil as a growth substrate was used, no consistent differences in seedling growth were obtained between the two litter leachate treatments. In the soil core experiment seedlings grown in soil cores collected from a denseB. orientalis stand unexpectedly showed better performance than seedlings grown in soil cores collected from a nearby mixed plant stand withoutB. orientalis, at least in early spring and late autumn. Predominating nutrient effects are, therefore, assumed to conceal a potentially increased allelopathic effect of soil beneath denseB. orientalis stands. It is concluded that other factors than allelopathy must be investigated to explain the rapid establishment of dense stands of this alien plant species.     

A chemical basis for differential allelopathic potential of sorghum hybrids on wheat

The basis for differential allelopathic potentials among sorghum (Sorghum bicolor L. Moench) hybrids was investigated by conducting quantitative and qualitative studies of their phenolic contents. Total phenolic content in sorghum plant parts varied within hybrids, among hybrids, and between growing seasons. Inhibition of wheat (Triticum aestivum L.) radicle growth was positively associated (r=0.66) with concentrations of total phenolics contained in plant parts. Extracts from culms contributed the higherst proportion of toxicity from sorghum plants, inhibiting radicle growth up to 74.7%. Concentrations of five phenolic acids,p-hydroxybenzoic (POH), vanillic (VAN), syringic (SYR),p-coumaric (PCO), and ferulic (FER), differed in all plant parts of the three sorghum hybrids. Concentrations of POH, VAN, and SYR were consistently higher than PCO and FER. PCO and FER wer absent from some plant parts, with FER being the most frequently missing. Inhibition of wheat radicle growth was found to be positively associated with the concentration of each phenolic acid. Vanillic acid was most highly associated (r=0.44) with inhition. Thus, above-ground sorghum tissues contained phenolic acids that contributed to allelopathic potential. Additionally, sorghum roots exuded POH, VAN, and SYR that may enhance the overall allelopathic potential of sorghum during growth and after harvest when residues remain on the soil surface or are incorporated prior to planting a subsquent crop.Journal article No. 12245 of the Missouri Agricultural Experiment Station. Product names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the products, and the use of names by USDA implies no approval of the products to the exclusion of others that may be suitable.     

Accelerated soil mineralization,nitrification, and revegetation of abandoned fields due to the removal of crop-soil phytotoxicity

In an abandoned corn field, clear-cutting of crop vegetation increased the productivity, species richness, and nonannuals in the following years after abandonment, as compared to the control plots from which crop vegetation was not removed. The increase in plant growth was apparently due to the elimination of allelopathic chemicals from the soil, which normally are released from the standing crop. Removal of vegetation also increased the soil mineralization of Ca²⁺, Mg²⁺, K⁺, NH₄ ⁺ and NO₃ ^–-N. This situation encouraged species having higher mineral requirements to rapidly invade the fields in the successive years. Clear-cutting also increased the nitrification process by removing the inhibitors of nitrification. The number ofNitrosomonas was always significantly higher in the harvested plots as compared to unharvested plots. Phenolic phytotoxins were isolated from the crop residue and soil. Further, these phytotoxins were significantly higher in the unharvested crops as compared to clear-cut plots, in most samples. Whatever the direct or indirect additional explanation for increased biomass, nonannuals and richness in successive years, it is clear that the removal of standing crop has a definite influence.     

Growth Inhibitory Effects of Nutgrass (Cyperus rotundus) on Rice (Oryza sativa) Seedlings

Growth inhibitory effects of aqueous extracts and leachates of leaves and tubers of Cyperus rotundus L. were investigated by using rice (Oryza sativa L.) seedling as a bioassay material. Both the extracts and leachates of Cyperus were inhibitory to the growth of rice seedlings. Growth inhibition was more pronounced in the presence of aqueous extracts than the leachates. The extract and leachate of leaves had higher total phenolic contents than those of the tubers. Soil amendment with fresh leaves of Cyperus reduced plant height, leaf area, and root and shoot weight of rice seedlings. Total phenolic content was higher in soil amended with fresh Cyperus leaves than the unamended control soil. Nineteen compounds were tentatively identified from the aqueous extracts of leaves and tubers by ethyl acetate extraction followed by gas chromatography–mass spectroscopy (GC-MS). Dicarboxylic, phenolic, and fatty acids were the major compounds. Our results suggest that Cyperus may affect the growth and establishment of rice seedlings after sowing or transplanting, especially when Cyperus plants are mixed in soil during land preparation by ploughing in rain-fed rice culture.     

Interactions betweenKalmia and black spruce: Isolation and identification of allelopathic compounds

Aqueous extracts of fresh leaves and organic soil of northern sheep laurel (Kalmia angustifolia var.angustifolia) were found to be inhibitory to the growth of black spruce (Picea mariana) germinants. Primary root growth of black spruce was more affected by the extracts than was shoot growth. The growth inhibition caused by the leaf extract was most pronounced under acidic conditions (pH 3–4). The aqueous extract ofKalmia leaves contained ferulic, vanillic, syringic, gentisic,m-coumaric,p-coumaric,o-hydroxyphenylacetic, andp-hydroxybenzoic acids as well as some other unknown compounds. These compounds were isolated from the aqueous extract ofKalmia leaves by ethyl acetate extraction and identified using thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC). Bioassay indicated that the overall toxicity of the phenolic compounds to black spruce appeared to increase in the order ofo-hydroxyphenylacetic,p-hydroxybenzoic, vanillic,p-coumaric, gentisic, syringic, ferulic, andm-coumaric acids.     

Geographic Variation in Sex Pheromone Blend of Hemileuca electra from Southern California

Differences were found in the pheromonally mediated mate location systems of two subspecies of Hemileuca electra, H. electra electra (Hee) and H. e. mojavensis (Hem), from southern California. Hem female pheromone gland extracts contained eight times as much (10E,12Z)-hexadeca-10,12-dienal (E10,Z12–16:Ald) and half as much hexadecyl acetate (16:Ac) as Hee extracts. Relative amounts of the other major component of the pheromone blends, (10E,12Z)-hexadeca-10,12-dien-1-ol (E10,Z12–16:OH) did not differ between the two subspecies. In coupled gas chromatography–electroantennogram studies, responses of male antennae to 1:1:1 mixtures of the three principal components (E10,Z12–16:Ac, E10,Z12–16:OH, E10,Z12–16:Ald) also differed, with Hem antennae producing significantly larger responses to E10,Z12–16:Ald and significantly smaller responses to 10E,12Z–16:Ac than Hee. In field trials, male Hem were attracted to Hem females in preference to Hee females. Males of a second species, H. burnsi, which is sympatric with Hem but not Hee, also were attracted to females of Hee transported to their range. Field tests of blends of synthesized pheromone components confirmed that male Hem preferred E10,Z12–16:Ald ratios of 10–100% of the major component, E10,Z12–16:Ac, whereas males of Hee and H. burnsi responded optimally to ratios of 0.3–1% E10,Z12–16:Ald to E10,Z12–16:Ac. 16:Ac added to lures increased attraction of Hee but not Hem males. The data presented are consistent with reproductive character displacement, whereby the Hem subspecies has modified its pheromone-based mating system to reduce interference from sympatric H. burnsi.     

Solution volume and seed number: Often overlooked factors in allelopathic bioassays

Cucumber seeds were germinated under various combinations of solution volume and seed number with a range of ferulic acid concentrations. At each concentration, radicle growth decreased as the relative amount of ferulic acid available per seed increased from (25 seeds/5 ml) to 5 (5 seeds/5 ml) to 19 (25 seeds/95 ml). With 2.0 mM ferulic acid in buffered solution, radicle lengths after 48 hr ranged from 71 to 47% of control. The amount of ferulic acid remaining in 2.0 mM solution after 48 hr was directly proportional to the amount initially available per seed, and ranged from 9 to 91%. Solution volume and seed number also significantly affected inhibition by vanillic acid, caffeic acid, and juglone. With 0.1 mM juglone, radicle lengths after 48 hr were 88% of control with 25 seeds/5 ml, 68% with 5 seeds/5 ml, and 56% with 25 seeds/90 ml. The data demonstrated that lower phytotoxin concentrations can produce equivalent or greater inhibitory effects than higher concentrations when the amount available per seed for uptake is greater. Equivalent inhibition of radicle growth was observed with 1.0 mM (5 seeds/5 ml) and 2.0 mM (25 seeds/5 ml) ferulic acid. Available literature on herbicides indicates that similar effects occur in greenhouse and field studies.     

Why Phenolic Acids Are Unlikely Primary Allelochemicals in Rice

Allelopathy in rice (Oryza sativa, L.) effective against weeds has been found in about 3.5% of tested rice germplasm in both laboratory and field experimentation. However, the allelochemicals responsible for growth inhibition of rice-associated weeds have not yet been identified. In the literature, phenolic acids are often mentioned as putative allelochemicals. If phenolic acids commonly reach growth inhibitory concentrations in rice ecosystems, it must be expected that the degree of tolerance to phenolic acids will vary among traditional rice cultivars or plant species adapted to rice environments having inherently different phenolic acid concentrations. Phenolic acids concentrations are normally greater in submerged than in aerobic soils. A dose–response study, however, showed that seedlings of rice cultivars adapted to submerged anaerobic soils did not have higher level of tolerance against p-hydroxybenzoic acid than did seedlings of varieties adapted to aerobic upland soils. Moreover, traditional rice cultivars had no greater tolerance than did improved cultivars that were recently bred for traits other than tolerance of phenolic acids. Similarly, there were no differences in tolerance of p-hydroxybenzoic acid between two Echinochloa weed species adapted to either anaerobic or aerobic growth conditions. Thus, neither the rice cultivars nor weed species had evolved different tolerance levels against the phenolic acid. However, all rice cultivars had significantly greater tolerance of p-hydroxybenzoic acid than did either weed species. In a second experiment, the rates at which rice plants released phenolic acids into solution cultures were measured for at least one month, the time period of greatest allelopathic activity following planting under field conditions. The maximum release rate of phenolic acids during the first month of growth was approximately 10 g/plant/day. At a conventional plant density, the release rate of phenolic acids would be approximately 1 mg/m²day. This order of release rate cannot provide concentrations remotely close to phytotoxic levels determined for these rice cultivars and weed species. The results presented in this paper do not preclude the possibility that phenolic acids might be one component in a mixture of chemicals that, when present simultaneously, are allelopathic.     

The role of lanierone in the chemical ecology ofIps pini (Coleoptera: Scolytidae) in California

Five doses of lanierone (2-hydroxy-4,4,6-trimethyl-2,5-cyclohexadien-1-one) were tested with one dose of enantiomerically pure [99.4% (4R)-(–)] ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) for activity as an aggregation pheromone ofIps pini (Say) in California. The response ofI. pini to 1 mg/day ipsdienol + 20 g/day lanierone was significantly greater than the response to ipsdienol alone, but the response pattern did not demonstrate a clear dose-response relationship. The response to the highest dose of lanierone (2 mg/day) was significantly lower than the response to ipsdienol alone. Ipsdienol attracted significantly moreI. pini than a male-infested log. Lanierone did not alter the percentage of maleI. pini responding to ipsdienol alone. Neither sex ofI. pini orDendroctonus brevicomis LeConte from California produced detectable amounts of lanierone, but myrcene-aerated maleD. brevicomis produced 97.8%-(4S)-(+)-ipsdienol. The black-bellied clerid,Enoclerus lecontei (Wolcott) (Coleoptera: Cleridae) was attracted to lanierone when released with ipsdienol. Neither compound was attractive when released alone, proving synergism for the kairomone of this predator. Lanierone did not influence the response of the predatorsTemnochila chlorodia (Mannerheim) (Coleoptera: Trogositidae) andEnoclerus sphegeus (F.) (Coleoptera: Cleridae), which were attracted to all treatments containing ipsdienol.Tomicobia tibialis Ashmead (Hymenoptera: Pteromalidae) responded in significantly greater numbers to the male-infested log than it did to ipsdienol or ipsdienol + 20 g/day lanierone.     

Kinetics of the Natural Evolution of Hydrogen Cyanide in Plants in Neotropical <Emphasis Type="Italic">Pteridium arachnoideum</Emphasis> and its Ecological Significance

The time-dependent natural release of hydrogen cyanide (HCN) was studied quantitatively using young croziers of the neotropical bracken fern Pteridium arachnoideum. HCN production was quantified in crushed tissue using a flow reactor at 30.0 ± 0.1C. Released HCN was carried into appropriate traps with a moist air flow. Aliquots were drawn from the traps at fixed time intervals, and the HCN concentration was evaluated spectroscopically. All available prunasin (Pru), the only cyanogenic glycoside present, underwent decomposition into HCN in less than 1200 min. Fiddleheads (N = 76) contained 1.84–107.70 mg Pru g^–1 dw in a continuous fashion suggesting genetic polymorphism. Acyanogenic morphs were rare (1/77). From the kinetics of the samples with Pru content near the median histographic distribution (N = 46), accumulated HCN formation as a function of time, initial velocities, average HCN production rate, and corresponding rate equations were obtained. Initial and average velocities correlated well with total Pru content. The yield of cyanide liberation varied widely between 0.51 and 47.86 g HCN min^–1 g^–1 dw and was a linear function of [Pru]_t. However, the -glucosidase enzyme involved in this reaction was not rate limiting and occurs in excess in the natural system. Enzyme activity was found to be independent of [Pru]_t. The contribution of HCN as an allomone-upon-request against herbivores was assessed quantitatively. Bracken fiddleheads produced a pulse of HCN soon after tissue injury that waned rapidly, leaving a large portion of intact prunasin to decompose more slowly in the herbivores lumen. The balance between the external and internal courses was found to depend on the concentration of prunasin in the plant, the amount of crozier eaten, and the time used to consume it.     

Allelochemicals Isolated from Tissues of the Invasive Weed Garlic Mustard (Alliaria petiolata)

Garlic mustard (Alliaria petiolata) is a naturalized Eurasian species that has invaded woodlands and degraded habitats in the eastern United States and Canada. Several phytotoxic hydrolysis products of glucosinolates, principally allyl isothiocyanate (AITC) and benzyl isothiocyanate (BzITC), were isolated from dichloromethane extracts of garlic mustard tissues. AITC and BzITC were much more phytotoxic to wheat (Triticum aestivum) than their respective parent glucosinolates sinigrin and glucotropaeolin. However, garden cress (Lepidium sativum) growth was inhibited to a greater degree by glucotropaeolin than BzITC, possibly due to conversion to BzITC by endogenous myrosinase. Sinigrin and glucotropaeolin were not detected in leaf/stem tissues harvested at the initiation of flowering, but were present in leaves and stems harvested in the autumn. Sinigrin levels in roots were similar for both sampling dates, but autumn-harvested roots contained glucotropaeolin at levels over three times higher than spring-harvested roots. The dominance of garlic mustard in forest ecosystems may be attributable in part to release of these phytotoxins, especially from root tissues.     

Use of water and EDTA extractions to estimate available (free and reversibly bound) phenolic acids in Cecil soils

Sterile and microbe reinfested Cecil A_p and B_t soil materials amended with 0 to 5 µmol/g of ferulic acid,p-coumaric acid,p-hydroxybenzoic acid, or vanillic acid were extracted after varying time intervals with water, EDTA, or NaOH to characterize sorption of cinnamic and benzoic acid derivatives and to determine the effectiveness of water and EDTA extractions in estimating concentrations of free and reversibly bound phenolic acids in soils. Basic EDTA (0.5 M, pH 8) extractions and water extractions provided good estimates of both free and reversibly bound cinnamic acid derivatives, but not of benzoic acid derivatives. Neutral EDTA (0.25 M, pH 7) and water extractions, however, were effective for both cinnamic and benzoic acid derivatives Rapid initial sorption of both cinnamic and benzoic acid derivatives was followed by slow long-term sorption of the cinnamic acid derivatives. Slow long-term sorption was not observed for the benzoic acid derivatives. The amount of sorption of phenolic acids in soil materials was directly related to the concentration of phenolic acids added to soil materials. The addition of a second phenolic acid to the soil materials did not substantially affect the sorption of each individual phenolic acid. Sodium hydroxide extractions, which were made only after phenolic acids in phenolic acid-amended and non-amended soil material were depleted by microbes, confirmed that neutral EDTA and water extractions of soils can be used to make accurate estimates of baseline (residual) levels of free and reversibly bound phenolic acids available to soil microbes and, thus, potentially to seeds and roots.The use of trade names in this publication does not imply endorsement by the North Carolina Agricultural Research Service of products named, nor criticism of similar ones not mentioned.     

Isolation and characterization of allelopathic volatiles from mugwort (<Emphasis Type="Italic">Artemisia vulgaris</Emphasis>)

Several volatile allelochemicals were identified and characterized from fresh leaf tissue of three distinct populations of the invasive perennial weed, mugwort (Artemisia vulgaris). A unique bioassay was used to demonstrate the release of volatile allelochemicals from leaf tissues. Leaf volatiles were trapped and analyzed via gas chromatography coupled with mass spectrometry. Some of the components identified were terpenes, including camphor, eucalyptol, -pinene, and -pinene. Those commercially available were tested individually to determine their phytotoxicity. Concentrations of detectable volatiles differed in both absolute and relative proportions among the mugwort populations. The three mugwort populations consisted of a taller, highly branched population (ITH-1); a shorter, lesser-branched population (ITH-2) (both grown from rhizome fragments from managed landscapes); and a population grown from seed with lobed leaves (VT). Considerable interspecific variation existed in leaf morphology and leaf surface chemistry. Bioassays revealed that none of the individual monoterpenes could account for the observed phytotoxicity imparted by total leaf volatiles, suggesting a synergistic effect or activity of a component not tested. Despite inability to detect a single dominant phytotoxic compound, decreases in total terpene concentration with increase in leaf age correlated with decreases in phytotoxicity. The presence of bioactive terpenoids in leaf surface chemistry of younger mugwort tissue suggests a potential role for terpenoids in mugwort establishment and proliferation in introduced habitats.     

Comparative analysis of allelopathic effects produced by four forestry species during decomposition process in their soils in Galicia (NW Spain)

The development of toxicity produced by vegetable litter of four forest species (Quercus robur L.,Pinus radiata D.Don.,Eucalyptus globulus Labill, andAcacia melanoxylon R.Br.) was studied during the decomposition process in each of the soils where the species were found. The toxicity of the extracts was measured by the effects produced on germination and growth ofLactuca saliva L. var. Great Lakes seeds. The phenolic composition of the leaves of the four species was also studied using high-performance liquid chromatographic analysis (HPLC). It was verified that toxicity was clearly reflected in the first stages of leaf decomposition inE. globulus andA. melanoxylon, due to phytotoxic compounds liberated by their litter. At the end of half a year of decomposition, inhibition due to the vegetable material was not observed, but the soils associated with these two species appeared to be responsible for the toxic effects. On the other hand, the phenolic profiles are quite different among the four species, and greater complexity in the two toxic species (E. globulus andA. melanoxylon) was observed.     

Biotransformation of 2-Benzoxazolinone to 2-Amino-(3<Emphasis Type="Italic">H</Emphasis>)-Phenoxazin-3-one and 2-Acetylamino-(3<Emphasis Type="Italic">H</Emphasis>)-Phenoxazin-3-one in Soil

An alternative to the use of synthetic pesticides is to exploit the natural defense chemicals produced by cereals. An important class of allelochemicals is cyclic hydroxamic acids and related benzoxazolinones. A prolonged degradation experiment of the allelochemical compound from rye 2-benzoxazolinone (BOA) was carried out for up to 90 d at 15°C at three different concentration levels, 3, 3000, and 30,000 nmol BOA· g soil^–1, respectively, in a sandy loam soil. Two main degradation products, 2-amino-(3H)-phenoxazin-3-one (APO) and 2-acetylamino-(3H)-phenoxazin-3-one (AAPO), were identified and quantified by LC-ESI-MS-MS. The half-life of BOA increased with higher levels of BOA added to the soil. Half-lives of BOA, APO, and AAPO were determined by fitting a single first-order model to the degradation data. Half-life of BOA was determined to be 0.6 d in the 3 nmol BOA g soil^–1 treatment. Half-lives of BOA, APO, and AAPO were 3.1, 2.7, and 2.1 d, respectively, in the 3000 nmol BOA· g soil^–1 treatment. In the 30,000 nmol BOA· g soil^–1 treatment, the half-lives were 31 d for BOA and 45 d for APO. The microbial community structure was not affected by addition of BOA to the soil as investigated by analysis of signature fatty acids. The results suggest that the exploitability of BOA for crop protection is dependent on the existing concentration of BOA in the soil and the timing of incorporation of hydroxamic acid synthesizing crops into the soil.