Alfalfa metabolism of propham

Root-treated alfalfa absorbs, translocates, and metabolizes [phenyl-¹⁴C]isopropyl carbanilate ([¹⁴C]propham). After 7 days of root treatment, the distribution of radiolabel was 73% for shoots and 27% for roots. Shoots and roots were extracted and separated into the polar, nonpolar, and solid residual components using a mixture of chloroform, methanol and water. The insoluble residues accounted for approximately 40% of the ¹⁴C found in shoots and roots. The nonpolar fraction (6.1% of the radiolabel in shoots and roots) was not characterized, but was shown to be some component other than parent propham. Propham was not found in either shoots or roots. The polar metabolites were partly purified on Amberlite XAD-2. Cellulase-liberated aglycones were derivatized and separated by high-performance liquid and gas-liquid chromatography. The infrared, nuclear magnetic resonance, and mass spectral data showed that the polar metabolites of alfalfa shoots and roots were glycoside conjugates of isopropyl 2-hydroxycarbanilate (2-hydroxypropham) and isopropyl 4-hydroxycarbanilate (4-hydroxypropham). Conjugated 4-hydroxypropham accounted for 45.9% of the ¹⁴C in the shoots and 3.4% of the ¹⁴C in the roots. Conjugated 2-hydroxypropham accounted for 3.4% of the ¹⁴C in the shoots and 1.4% of the ¹⁴C in the roots.     

Metabolism of isopropyl carbanilate by soybean plants

Root-treated soybean plants absorb, translocate, and metabolize isopropyl carbanilatephenyl-¹⁴C (propham-¹⁴C). After a 3-day treatment period and removal of the exogenous ¹⁴C treating solution, only small concentrations of ¹⁴C-labeled materials were found in newly emerging tissues. A measurable concentration of radiocarbon was found in the seed pods, but the fruit tissues were shown to be free of any dectable ¹⁴C-labeling. Three days after removal of the exogenous propham-¹⁴C, the parent herbicide was completely metabolized by all tissues. Polar products and nonextractable residues were found in roots, stems, and leaves after a 3-day treatment period. The polar metabolites were not translocated once they were formed in either the roots or shoots.Conjugated polar metabolites were isolated, partially purified, and the prophamphenyl-¹⁴C moiety characterized. The aglycone moiety of the polar metabolites was liberated either by methanol-HCl solvolysis or by enzyme hydrolysis with β-glucosidase or hesperidinase. The aglycone from all three procedures was derivatized, purified and characterized by NMR, ir, and mass spectral analysis. The only aglycone was the derivative of isopropyl-2-hydroxycarbanilate which was at least in part conjugated as a glycoside.     

Metabolism of isopropyl carbanilate (propham) in alfalfa grown in nutrient solution

Alfalfa plants, Moapa variety, were grown in nutrient solution containing isopropylring-[¹⁴C] carbanilate (43.8 μCi/liter propham). After 8 days, 41.2% of the radioactivity initially added to the nutrient culture was recovered; 10.9% of this was from shoots, 3.4% from roots and 26.9% from nutrient medium. Nonextracted residues accounted for 23% of the radioactivity in shoots and 62% of that in roots. The parent herbicide constituted 53 and 38% of the radioactivity extracted from shoots and roots, respectively. The balance of extracted ¹⁴C was polar metabolites which were purified and subjected to enzymatic and acid hydrolysis. Four aglycones were isolated, three of which were purified by thin-layer chromatography and characterized by mass spectrometry. The principal aglycones were: isopropyl-2-hydroxycarbanilate, isopropyl-4-hydroxycarbanilate, and 1-hydroxy-2-propylcarbanilate. The fourth aglycone was not identified.     

Animal metabolism of propham (isopropyl carbanilate): The fate of residues in alfalfa when consumed by the rat and sheep

Alfalfa was root-treated with [¹⁴C]propham (isopropyl carbanilate[¹⁴C-phenyl(U)]) for 7 days and then harvested and freeze-dried. Rats and sheep were orally given either ¹⁴C-labeled alfalfa roots ([¹⁴C]root) or ¹⁴C-labeled alfalfa shoots ([¹⁴C]shoot). When the [¹⁴C]root was given, 6.5–11.0% of the ¹⁴C was excreted in the urine and 84.6–89.4% was excreted in the feces within 96 h after treatment. Less than 3% of the ¹⁴C remained in the carcass (total body—gastrointestinal tract and contents) 96 h after treatment. When [¹⁴C]shoot was given, 53.2–55.2% of the ¹⁴C was excreted in the urine, 32.1–43.4% was excreted in the feces, and the carcass contained 0.2–1.1% of the ¹⁴C 96 h after treatment. When the insoluble fraction (not extracted by a mixture of CHCl₃, CH₃OH, and H₂O) of both alfalfa roots and shoots was fed to rats, more than 86% of the ¹⁴C was excreted in the feces and less than 3% remained in the carcass 96 h after treatment. The major radiolabeled metabolites in the urine of the sheep fed ¹⁴C shoot were purified by chromatography and identified as the sulfate ester and the glucuronic acid conjugates of isopropyl 4-hydroxycarbanilate. Metabolites in the urine of the sheep treated with [¹⁴C]root were tentatively identified as conjugated forms of isopropyl 4-hydroxycarbanilate, isopropyl 2-hydroxycarbanilate, and 4-hydroxyaniline. The combined urine of rats dosed with [¹⁴C]shoot and [¹⁴C]root contained metabolites tentatively identified as conjugated forms of isopropyl 4-hydroxycarbanilate, isopropyl 2-hydroxycarbanilate, and 4-hydroxyaniline.     

Effect of isopropyl-3-chlorocarbanilate and isopropyl-3-chlorohydroxycarbanilate analogs upon oxidative phosphorylation in plant mitochondria

The effects of the herbicide, isopropyl-3-chlorocarbanilate, and its hydroxylated metabolites, isopropyl-5-chloro-2-hydroxycarbanilate and isopropyl-3-chloro-4-hydroxycarbanilate, upon NADH oxidation, P_i uptake or release, and ATP formation were studied in corn mitochondria. The results indicated that 0.1 mM isopropyl-3-chlorocarbanilate and the 2-hydroxy-metabolite inhibited NADH oxidation by 30% whereas only the 2-hydroxy-metabolite inhibited NADH-linked ATP formation (85–100%). Dinitrophenol and the 2-hydroxy-metabolite exerted similar effects upon respiration, phosphorylation, and ATPase activity. The 4-hydroxy-metabolite (0.1 mM) exerted no effect upon respiration, phosphorylation, or ATPase activity. The β-O-glucoside conjugates of the hydroxymetabolities of isopropyl-3-chlorocarbanilate did not inhibit NADH-linked respiration or phosphorylation at 0.1 mM concentrations. Comparative studies with corn, cucumber, and soybean mitochondria indicated that the parent herbicide and its metabolites affected respiration and phosphorylation activities in a similar manner.     

S-cysteinyl-hydroxychlorpropham: Formation of the S-cysteinyl conjugate of isopropyl-3′-chloro-4′-hydroxycarbanilate in oat (Avena sativa L.)

Isopropyl-3′-chlorocarbanilate (chlorpropham) forms phenolic metabolites, isopropyl-3′-chloro-4′-hydroxycarbanilate (I), and isopropyl-5′-chloro-2′-hydroxycarbanilate (II), in several plant species. In oat, which is a chlorpropham-susceptible plant, I was converted to an S-cysteinyl-conjugate (III). The reaction in vitro was catalyzed by a partially purified, soluble enzyme. The formation of III by the enzyme preparation and by oat shoot sections was compared. Mass spectral data indicated the presence of an aryl-thioether bond, and chloro-, hydroxy-, and isopropylcarbanilate groups in III. The results of this investigation indicate that III was isopropyl-[(2-amino-2-carboxyethyl)thio]-chloro-hydroxycarbanilate (S-cysteinyl-hydroxychlorpropham).     

Deamination of metribuzin in tolerant and susceptible soybean (Glycine max) cultivars

The deamination of metribuzin was studied in vitro in peroxisomes isolated from the leaves of soybean cultivars which were either metribuzin tolerant, intermediate, or sensitive. The deamination rate observed with peroxisomes from tolerant leaves was about twice the rate observed with peroxisomes from sensitive leaves. The intermediate group was also intermediate with respect to the in-vitro deamination rate. Tolerant and sensitive intact soybean plants were pulse-labeled with [¹⁴C]metribuzin via the roots for 5 h. The extractable radioactivity in roots, stems and leaves was measured and separated into metabolites after the 5 h pulse and after an additional 24 h growth in water. The level of DA (deaminated metribuzin) was always significantly higher in the stems and leaves of tolerant soybean plants (4.8–10.0% of the extracted radioactivity) than in sensitive stems and leaves (1.8–2.9%). Conjugates were rapidly formed in tolerant as well as in sensitive soybean tissues. More conjugates were found in the tolerant cultivars, especially after the 5 + 24 h incubation time. Labeled [¹⁴C]DA fed to soybean plants via the roots was conjugated two to four times faster than [¹⁴C]metribuzin. Tolerant soybean tissue conjugated [¹⁴C] DA two to three times faster than sensitive tissue. The results are interpreted as showing that, in tolerant soybean plants, metribuzin is metabolized via deamination and subsequent conjugation, in addition to the well-known direct conjugation of metribuzin parent compound.     

Uptake, translocation and phytotoxicity of root-absorbed haloxyfop in soybean, Festuca rubra L. and Festuca arundinacea Schreb

The concentrations of haloxyfop in nutrient solution required to reduce the total plant dry weight of soybean (Glycine max L. Merr. ‘Evans’), red fescue (Festuca rubra L. ‘Pennlawn’), and tall fescue (Festuca arundinacea Schreb. ‘Houndog’) by 50% (GR₅₀) were determined. The GR₅₀) values for soybean, red fescue and tall fescue were 76 μM, 3μM and 0.4 μM, respectively. The reduction in growth in roots and shoots of soybean was similar. In contrast, the relative reduction in root tissue weight was greater than that for foliar tissue in both grass species. The amount of ¹⁴C-haloxyfop in soybean roots or shoots was higher than in red fescue or tall fescue. Red fescue accumulated less haloxyfop in the foliage than in the roots. On the other hand, similar amounts of ¹⁴C-haloxyfop accumulated in both organs in both soybean and tall fescue. ¹⁴C-haloxyfop appeared to be actively absorbed by the roots of all species. Soybean absorbed more nutrient solution, but utilized it less on a per gram dry matter produced basis than the grass species. Differences in the uptake and translocation of haloxyfop by roots do not account for differences in tolerance between species. However, a higher level of retention of haloxyfop in the roots of red fescue than in tall fescue may provide the former with an additional selectivity advantage under conditions where there is significant root exposure to the herbicide.     

Uptake patterns of soil-applied 45Ca and 32P in some legume species as influenced by differential trifluralin placement

The effect of localized placement of trifluralin on uptake patterns of soil-applied ⁴⁵Ca in vetch (Vicia sativa L.), pea (Pisum sativum L.) and soybean (Glycine max) and ³²P in vetch and pea was investigated in two soil zones in the roots and in the shoot zone before and after plant emergence. When trifluralin was in the upper root zone severe inhibition of lateral roots occurred as well as a marked decrease in uptake of ⁴⁵Ca and ³²P from this zone. Root growth in the lower zone was unaffected, but uptake of ⁴⁵Ca and ³²P was slightly reduced. Compensatory adventitious root growth as well as a marked increase in uptake of ⁴⁵Ca and ³²P occurred in the shoot zone. Neither root growth nor uptake of ⁴⁵Ca or ³²P in the upper root zone were affected by the presence of trifluralin in the lower root region. When trifluralin was placed in the shoot zone after plant emergence, adven-titious roots on the shoots were inhibited and uptake of ⁴⁵Ca and ³²P was reduced.     

Absorption and fate of imazapyr in leafy spurge (Euphorbia esula)

Imazapyr absorption, translocation, root release and metabolism were examined in leafy spurge (Euphorbia esula L.). Leafy spurge plants were propagated from root cuttings and [¹⁴C]imazapyr was applied to growth-chambergrown plants in a water + 28% urea ammonium nitrate + nonionic surfactant solution (98.75 + 1 + 0.25 by volume). Plants were harvested two and eight days after herbicide treatment (DAT) and divided into: treated leaf, stem and leaves above treated leaf, stem and leaves below the treated leaf, crown, root, dormant and elongated adventitious shoot buds. Imazapyr absorption increased from 62.5% 2 DAT to 80.0% 8 DAT. Herbicide translocation out of the treated leaf and accumulation in roots and adventitious shoot buds was apparent 2 DAT. By the end of the eight-day translocation period only 14% of applied ¹⁴C remained in the treated leaf, while 17% had translocated into the root system. Elongated and dormant adventitious shoot buds accumulated 3.2- and 1.8-fold more ¹⁴C, respectively, 8 DAT than did root tissue based on Bq g^?1 dry weight. Root release of ¹⁴C was evident 2 DAT, and by 8 DAT 19.4% of the ¹⁴C reaching the root system was released into the rooting medium. There was no metabolism of imazapyr in crown, root or adventitious shoot buds 2 DAT; however, imazapyr metabolism was evident in the treated leaf 2 and 8 DAT. Imazapyr phytotoxicity to leafy spurge appears to result from high imazapyr absorption, translocation to underground meristematic areas (roots and adventitious shoot buds), and a slow rate of metabolism.     

Uptake and fate of triticonazole applied as seed treatment to spring wheat (Triticum aestivum L.)

Following seed treatment of wheat (Triticum aestivum L.) with ¹⁴C-labelled triticonazole at a dose of 1·8 g kg^-1 seed, the uptake of radioactivity by shoots and roots was investigated from the two- to three-leaf stage up to the beginning of the booting phase, 80 days after sowing. Triticonazole equivalents taken up by wheat plants reached 5·7% and 14·6% of the applied dose in the shoots and the roots, respectively. Between the two- to three-leaf stage and the beginning of the booting phase, the concentration of triticonazole equivalents in the shoots decreased from 2·5 to 0·15 μg g^-1 fresh weight. This was attributed to uptake of triticonazole by roots not keeping pace with shoot growth and increased retention in the roots of triticonazole taken up. The main factor limiting the uptake of triticonazole by the roots may be the rapid growth of the uptake-active apical root parts out of the dressing zone which had formed in the soil. Distribution of triticonazole equivalents taken up by the main shoot showed a decreasing concentration gradient from the oldest to the youngest leaf. An increase in the seed treatment dose was investigated as a way to increase the concentration of triticonazole in the shoots, but its influence remained limited. © 1998 SCI     

Uptake and phytotoxicity of chlorsulfuron in Zea mays L. in the presence of 1,8-naphthalic anhydride

The sites of uptake of chlorsulfuron in maize (Zea mays L.) were investigated at three different growth stages. Exposure of seedling roots, or shoots separately, to herbicide-treated sand over 4 days resulted in inhibition of both roots and shoots. Exposure of seedling roots to chlorsulfuron-treated soil over 21 days severely inhibited both roots and foliage, while separate shoot exposure also reduced both foliage and root growth. After plant emergence, exposure of the crown root node, growing point and lower stem to treated soil reduced foliage and root growth, but exposure of the shoot above the growing point caused only slight inhibition of foliage and had no effect on roots. The herbicide safener 1,8-naphthalic anhydride (NA) applied as a dust (10 g kg^?1 seed weight), or as a 50 mg 1^?1 suspension in water to maize seeds, reduced the root inhibition by chlorsulfuron in 4-day-old seedlings. NA completely prevented both foliage and root injury when chlorsulfuron was placed in soil in the shoot zone before emergence, or in the shoot zone below the soil surface after plant emergence. NA slightly decreased injury to foliage, but not to roots when chlorsulfuron was placed in soil in the root zone before emergence. NA seed treatment protected both roots and foliage against injury from foliarly applied chlorsulfuron. Plants were also protected when a suspension of NA in water was sprayed on the foliage seven days before chlorsulfuron. When a mixture of NA and chlorsulfuron was applied to foliage, root injury was reduced more than foliage injury.     

Metribuzin degradation in soil: I—effects of soybean residue amendment,metribuzin level,and soil depth

Plant residue and soil depth effects on metribuzin degradation were investigated. Dundee silt loam soil collected at depth increments of 0–10 cm (SUR) and 10–35 cm (SUB) was treated with labeled [5^?14 C]metribuzin. Samples were assayed at several time points up to 140 days after treatment. Soybean residue was added to half of the SUR samples (RES), with remaining SUR unamended (NORES). None of the SUB samples were amended with soybean residue. Metribuzin mineralization to ¹⁴CO₂ proceeded more slowly in RES and SUB than in NORES and SUR, respectively. Extractable components in SUR samples included polar metabolites, plus deaminated metribuzin (DA) in the RES, and parent metribuzin in the NORES. Deaminated diketometribuzin (DADK) and metribuzin comprised major ¹⁴C components extracted from SUB, while in SUR, faster degradation of metabolites resulted in metrizubin as the primary identifiable compound. Unextractable ¹⁴C increased until day 35 for both RES and NORES, after which it remained constant for NORES. but declined for RES. A corresponding rise in RES polar ¹⁴C suggested that as soybean residue decomposed, ¹⁴C bound in the residue was released as extractable polar material. Soil with soybean residue accumulation may alter metabolite degradation patterns, but does not impede initial metribuzin degradation. Depth differences in metribuzin degradation were attributed to reductions in microbial activity with increasing soil depth.     

Glyphosate effects on Canada thistle (Cirsium arvense) roots, root buds, and shoots

Glyphosate ? ? Mention of irademark or proprietary product does not constitute a gtiarantee or warranty oC the product by the U.S. Department of Agriculture and does nut imply its approval to the exclusion of other products thai may also be suitable.
was sprayed at 0009–1·12 kg a.i. ha^?1 on the foliage of large potted glasshouse-grown Canada thistle [Cirsium arvense (L.) Scop.], which had extensive, well-developed roots. Increasing the glyphosate rate progressively reduced the total number of visible adventitious root buds plus emerged secondary shoots per plant proportionately more than root biomass, 10 days after treatment. Cortical tissue of thickened propagative roots became soft, water-soaked, darkened, and some regions decomposed, exposing strands of vascular tissue. Lateral roots completely decomposed. When thickened roots were segmented to stimulate secondary shoot emergence from root buds 10 days after foliar treatment, Fewer secondary shoots emerged than expected from the number of visible adventitious root buds present on both control and herbicide-treated plants. Increasing the rate of glyphosate also reduced the regrowth potential of root buds proportionately more than root biomass. Regrowth potential was measured as the number of emerged secondary shoots 35 days after segmenting unearthed roots from plants that had been sprayed 10 days earlier. When foliar-applied at 0·28 kg ha^?1, glyphosate decreased the regrowth potential of root buds to zero in 2 and 3 days, as measured by secondary shoot dry weight and number, respectively, even though root fresh weight was unchanged 3 days after foliar treatment. These dose-response and time-course experiments demonstrate that glyphosate did not reduce root biomass as much as it decreased root bud numbers and secondary shoot regrowth potential from root buds.     

Comparative metabolism of atrazine and EPTC in proso millet (Panicum miliaceum L.) and corn

The purpose of this study was to examine the differential activities of proso millet (Panicum miliaceum L.) and corn (Zea mays L.) with respect to atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-S-triazine] and EPTC (S-ethyldipropyl thiocarbamate) metabolism. GSH-S-transferase was isolated from proso millet shoots and roots. When assayed spectrophotometrically using CDNB (1-chloro 2,4-dinitrobenzene) as a substrate, the shoot enzyme had only 10% of the activity of corn shoot enzyme while the root enzyme had 33% the activity of corn root enzyme. However, when proso millet shoot GSH-S-transferase was assayed in vitro using ¹⁴C-ring-labeled atrazine, it degraded the atrazine to water-soluble products at the same rate as the corn shoot enzyme. Incubation of excised proso millet and corn roots with [¹⁴C]EPTC indicated that uptake of EPTC was similar in both plants. However, proso millet metabolized the EPTC to water-soluble products at only half the rate of corn. Glutathione levels of proso millet roots were 35.9 μg GSH/g fresh wt, compared with 65.4 μg GSH/g fresh wt for corn. However, a 2.5-day pretreatment with R-25788 (N,N-diallyl-2-2-dichloroacetamide) elevated proso millet GSH levels to 62.7 μg GSH/g fresh wt. R-25788 did not elevate the activity of proso millet GSH-S-transferase, in contrast to its effects on corn. We conclude that differences in response to atrazine and EPTC in proso millet and corn are a result of their differential metabolism.     

Effects of picloram on the synthesis of soluble plant proteins as determined by gel electrophoresis

Changes in soluble proteins synthesized in soybean (Glycine max L.), safflower (Carthamus tinctorius L.), radish (Raphanus sativus L.), and barley (Hordeum vulgare L.) treated with either growth promotive or inhibitory concentrations of picloram (4-amino-3,5,6-trichloropicolinic acid) were determined by polyacrylamide gel electrophoresis and isoelectric focusing. A special gel mixture was developed which provided resolution of protein bands superior to that obtained by standard gel electrophoresis. Growth promotive concentrations of picloram caused both qualitative and quantitative alterations in the band patterns of soluble proteins of safflower, radish, and barley roots and shoots. Isoelectric focusing was applied for the separation and identification of soluble protein fractions from soybean and barley roots and shoots treated primarily with growth inhibitory concentrations of picloram (except for barley shoot tissues). More than 35 clear bands were distinguishable in a typical gel electrophoretogram for either soybean or barley tissue (4-day-old plants). Approximate pI values of the bands from barley root protein were determined from a pH gradient diagram. Protein band patterns of picloram-treated samples were changed qualitatively and quantitatively, in comparison with controls, mostly in the range above pI 6, and predominantly in the neutral and basic protein regions. Band patterns for 96-hr root samples treated with growth inhibitory concentrations of picloram were more similar to those from 48-hr (soybean) or 55-hr (barley) than 96-hr control seedlings. A quantitative decrease in intensity of a band which had the same pI value as that of RNase was noticed in both the treated samples and 2- or 3-day-old control seedlings.     

Acifluorfen metabolism in soybean: Diphenylether bond cleavage and the formation of homoglutathione, cysteine, and glucose conjugates

Metabolism of the substituted diphenylether herbicide, acifluorfen [sodium 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate], was studied in excised leaf tissues of soybean [Glycine max (L.) Merr. ‘Evans’]. Studies with [chlorophenyl-¹⁴C]- and [nitrophenyl-¹⁴C]acifluorfen showed that the diphenylether bond was rapidly cleaved. From 85 to 95% of the absorbed [¹⁴C]acifluorfen was metabolized in less than 24 hr. Major polar metabolites were isolated and purified by solvent partitioning, adsorption, thin layer, and high-performance liquid chromatography. The major [chlorophenyl-¹⁴C]-labeled metabolite was identified as a malonyl-β- -glucoside (I) of 2-chloro-4-trifluoromethylphenol. Major [nitrophenyl-¹⁴C]-labeled metabolites were identified as a homoglutathione conjugate [S-(3-carboxy-4-nitrophenyl) γ-glutamyl-cysteinyl-β-alanine] (II), and a cysteine conjugate [S-(3-carboxy-4-nitrophenyl)cysteine] (III).     

Metabolism of [14C]vernolate in soybeans

Penetration and metabolism of [¹⁴C]vernolate in soybean [Glycine max (L.) Merr. var Ransom] pods and seeds were measured 0, 1, 4, 24, 48, or 72 hr after treatment which occurred at 40 days after flowering. Total ¹⁴C recovery decreased ca. 50% within 4 hr and the loss of ¹⁴C was considered to be a measure of volatility. Total nonpolar extractants decreased in a logarithmic pattern which approached 10% of total ¹⁴C recovered within 24–48 hr. Total polar extractants increased in a logarithmic pattern to a maximum of 90% of total ¹⁴C recovered within 24 hr. Seed nonpolar extractants never exceeded 2% of the total ¹⁴C recovered while pod nonpolar extractants consisted of vernolate plus an unidentified component that did not thin-layer chromatograph (TLC) as the sulfone or sulfoxide. Pod polar extractants increased with time to ca. 75% of the total ¹⁴C recovered (24–48 hr) and decreased to ca. 58% at 72 hr after treatment. Seed polar extractants averaged ca. 10% of total ¹⁴C recovered for the first 48 hr after treatment and then increased to 30% of total ¹⁴C recovered. Thus, [¹⁴C]vernolate per se concentration decreased to <1% of applied material within 72 hr through volatilization and degradation of nonpolar extractants to polar products. Polar metabolites showed two major patterns of vernolate detoxification. One detoxification system produced ¹⁴C-metabolites whose R_f's were equivalent to that reported in corn (Zea mays L.) [J. P. Hubbell and J. E. Casida, [J. Agric. Food Chem. 25, 404 (1977)] and accounted for <30% of the pod polar extractants. A second detoxification system was most prevalent in soybean pod and seed tissues and resulted in very rapid modification of vernolate with an unidentified product that was 85% of the extracted ¹⁴C within 4 hr after treatment and which decreased in concentration with time. Therefore, unexplained vernolate detoxification system(s) exist in soybean pod and seed.     

Metabolism of EPTC in germinating corn: Sulfone as the true carbamoylating agent

Corn (Zea mays L. single cross hybrid Mv 620) was germinated in a petri dish with addition of carbonyl[¹⁴C]EPTC (S-ethyl-N,N-dipropylthiocarbamate). The shoots and roots of 4-day-old seedlings were crushed and extracted in 80% methanol. On the chromatogram of the extract three radioactive peaks were found. The main peak was identified as S-(N,N-dipropylcarbamoyl)-glutathione. For the comparison of carbamoylating ability [¹⁴C]EPTC, [¹⁴C]EPTC-sulfoxide, and [¹⁴C]EPTC-sulfone were incubated with glutathione. Only EPTC-sulfone reacted in the 10-day incubation time. In aquatic solutions EPTC and EPTC-sulfoxide proved to be stable during the 10 days compared to EPTC-sulfone which quickly degraded, S-(N,N-Dipropylcarbamoyl)-glutathione was converted to S-(N,N-dipropylcarbamoyl)-cysteine in corn shoot homogenate. [¹⁴C]EPTC, [¹⁴C]EPTC-sulfoxide and [¹⁴C]EPTC-sulfone were added to corn shoot homogeneates and each of the three mixtures were analyzed by chromatography after 1 day incubation. EPTC was partly oxidized to EPTC-sulfoxide. EPTC-sulfoxide did not change and EPTC-sulfone produced similar metabolites as had been found in the germination experiment.     

Interactions between soil-applied herbicides in the roots of some legume species

The effects on plant growth of applying trifluralin or nitralin combination with simazine, atrazine, prometryne and linuron to the upper 5-cm root region of vetch (Vicia sativa L.), pea (Pisum sativum L.) and soybean (Glycine max) were investigated. Foliar injury due to herbicides of the second group was markedly reduced in each species by simultaneous treatment with trifluralin or nitralin both of which inhibited lateral root growth without affecting aerial plant growth or tap root extension growth. This inhibition of lateral root growth in roots treated with trifluralin or nitralin was associated with reduced uptake and subsequent transport to the foliage of ¹⁴C-labelled simazine in vetch and pea and ¹⁴C-labelled atrazine in soybean. This probably accounted for the reduction in simazine and atrazine phytotoxicity. In the presence of trifluralin or nitralin comparatively higher amounts of radioactivity were retained in the roots of pea and soybean and this reduced the amount of ¹⁴C available for transport to the foliage. This was not evident in vetch.