The effect of root-absorbed PSII inhibitors on Kautsky curve parameters in sugar beet

The effects of the photosystem II inhibitors metamitron and terbuthylazine on the shape of the Kautsky (chlorophyll fluorescence induction) curve were investigated in sugar beet grown in hydroponic culture. The objective of the study was to trace recovery processes following herbicide injury using Kautsky curve parameters. Metamitron is used for selective weed control in sugar beet because it is metabolized in this crop. In contrast, terbuthylazine is toxic to sugar beet. Two hours after treatment, various fluorescence induction curve parameters, such as maximum quantum efficiency (F_V/F_m), the relative changes at the J step (F_vj) and area (the area between the Kautsky curve and maximum fluorescence, F_m), were affected by metamitron at concentration ranges of 70–280 mg active ingredient (a.i.) L^?1 in plants treated at the four‐true‐leaf stage. Shortly after herbicide application, F_v/F_m was more affected by the hydrophilic metamitron [log(K_ow) = 0.83] than by the lipophilic terbuthylazine [log(K_ow) = 3.21], but these differences between compounds were alleviated as metamitron was metabolized and terbuthylazine was not. Terbuthylazine at 1 mg a.i. L^?1 affected sugar beet at the four‐ and six‐true‐leaf stages to the same extent, whereas metamitron at a dose of 140 mg a.i. L^?1 affected much more at four‐ than at the six‐true‐leaf stage. Sugar beet recovered from metamitron injury even at high doses (140 and 280 mg a.i. L^?1). Fluorescence induction curve parameters were similarly affected by terbuthylazine and, although sugar beet recovered from terbuthylazine injury at low doses (<0.2 mg a.i. L^?1), the Kautsky curve was irreversibly affected at higher doses (1–10 mg a.i. L^?1), leading finally to plant death. Older plants were affected later, and recovered sooner, from both herbicides.     

Characterisation of energy-dependent efflux of imazalil and fenarimol in isolates of Penicillium italicum with a low,medium and high degree of resistance to DMI-fungicides

Differential accumulation of [¹⁴C]imazalil and [¹⁴C]fenarimol by germlings of wild-type and DMI-resistant isolates ofPenicillium italicum was studied at various pH values. At pH 7 and 8 the low-resistant isolate E_300–3 accumulated 22% and 35%, respectively, less imazalil than the wild-type isolate W₅. Imazalil accumulation at pH 5 and 6 was similar. Isolate E_300–3 also accumulated less fenarimol as compared with the wild-type isolate. This difference was much more obvious than for imazalil and was observed at all pH values tested. Differences in accumulation of both imazalil and fenarimol between low (E_300–3), medium (H₁₇) and high resistant (I₃₃) isolates were not observed. These results suggest that decreased accumulation of DMIs is responsible for a low level of resistance only and that additional mechanisms of resistance might operate in isolates with a medium and high degree of resistance. With all isolates fenarimol accumulation was energy-dependent. This was not obvious for imazalil.The wild-type and DMI-resistant isolates had a similar plasma membrane potential as determined with the probe [¹⁴C]tetraphenylphosphonium bromide ([¹⁴C]TPP⁺). Various test compounds, among which ATPase inhibitors, ionophoric antibiotics and calmodulin antagonists, affected the accumulation of [¹⁴C]TPP⁺, [¹⁴C]imazalil and [¹⁴C]fenarimol. No obvious correlation between the effects of the test compounds on accumulation levels of the fungicides and [¹⁴C]TPP⁺ could be observed. These results indicate that the plasma membrane potential does not mediate the efflux of DMI fungicides byP. italicum.     

A study of ethylene and CO2 evolution from ethephon in tobacco

Buffers and leaf discs of mature tobacco (Nicotiana tabacum L.) were utilized to study [¹⁴C]-ethylene and ¹⁴CO₂ evolution from radiolabeled ethephon, (2-chloroethyl)phosphonic acid. Metabolic fate of [¹⁴C]ethephon in leaf discs was investigated by use of thin-layer chromatography, high-voltage paper electrophoresis, autoradiography, and liquid scintillation spectroscopy. The evolution of labeled ethylene generally increased with increasing buffer pH, buffer volume, and dosage of [¹⁴C]ethephon. [¹⁴C]Ethylene was evolved, increasingly with time, from [¹⁴C]ethephon either added to the buffer or applied to leaf discs. The rate of [¹⁴C]ethylene evolution was maximum during the first day and leveled off on the fourth day. More than 50% of the total [¹⁴C]ethylene evolution over a 96-hr period was recovered during the first 24 hr after [¹⁴C]ethephon application. No ¹⁴CO₂ was evolved when [¹⁴C]ethephon was degraded in the presence of buffer or leaf discs. Only ethephon itself, and no detectable metabolite thereof, was discovered in the methanolic extract of the leaf disc tissue. An insignificant amount of ¹⁴C activity (approximately 2% of the extracted ¹⁴C) was detected in the residue. By means of gas chromatography, it was confirmed that in buffers and tobacco leaf tissue ethephon breaks down to release ethylene but not CO₂.     

Microbial dealkylation of trifluralin in pure culture

Mixed populations of soil microorganisms were enriched in the presence of trifluralin (α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) and 180 pure strains were subsequently isolated. About a third were able to liberate 1.5–6% ¹⁴CO₂ from 0.15 mM [propyl-1-¹⁴C]trifluralin after growing for 21 days on a complex medium. One strain, identified as a Candida sp., showed a ¹⁴CO₂ evolution of 11%. The amount of liberated ¹⁴CO₂ could not be enhanced by adding small concentrations (<3%) of solvents to the culture, by varying the concentration of trifluralin, or by varying the composition of the complex medium. The Candida sp. was unable to cleave the aromatic ring of trifluralin or to use trifluralin as a sole source of carbon or nitrogen. Only traces (< 1%) of dealkylated trifluralin were accumulated in the culture.     

Metabolic studies of 14C-labeled propham and chlorpropham in the female rat

The tissue distribution and excretion of ¹⁴C-labeled propham and chlorpropham were investigated in the adult female rat after a single oral dosage. The average 3-day urinary excretions of radioactivity were 55.9%, 82.6%, 79.5%, and 85.4% of an oral dose of chain [¹⁴C] chlorpropham, ring [¹⁴C] chlorpropham, chain [¹⁴C] propham, and ring [¹⁴C] propham, respectively. With chain [¹⁴C] chlorpropham 35.4 ± 7.5% of the administered radioactivity appeared in the respired air, whereas only 5.0 ± 0.8% was found in CO₂ from chain [¹⁴C] propham. There was no significant difference in the rate of excretion or the route of elimination among rats receiving different oral dosages, ranging from less than 4 mg/kg to 200 mg/kg. The radioactivity was distributed in all tissues with highest concentration found in the kidney. The average biological half-life of ¹⁴C from chlorpropham and propham in most organs was short, ranging between 3 and 8 hr; however, in brain, fat, and muscle, the half-life was about twice the value for other organs.Both compounds were metabolized by hydrolytic and oxidative mechanisms and the resulting metabolites were excreted either as free forms or as conjugates.Subcellular distribution of ¹⁴C in the rat liver and kidney after an oral administration of chlorpropham and propham was investigated. The percentage distribution of ¹⁴C in the particulate and soluble fractions was dependent on the elapsed time after dosing.     

The toxicological significance of paraoxon deethylation

The in vivo formation of deethylation and hydrolytic products of paraoxon degradation after parathion or paraoxon administration was nearly equal in control male rats, and the relative abundance of metabolites was not appreciably altered by pretreatment of rats with enzymeinducing agents. However, pretreatment with inducers dramatically increased the oxidative paraoxon O-deethylase of male rat liver while having little effect on hydrolytic enzymes. Prior to induction, the hepatic O-deethylase activity was greatly inferior to the various hydrolytic enzymes, but nearly equal levels of both enzyme systems were found after induction. These results indicate that a large portion of the hepatic hydrolases detected in vitro is not active in vivo. It also appears that the majority of the induced hepatic deethylase was not involved in vivo at the dosage levels employed. The in vivo metabolism of monoethyl paraoxon was also demonstrated. The predominant metabolite of ethyl-[1-¹⁴C]monoethyl paraoxon is ¹⁴CO₂, while phenyl-[1-¹⁴C]monoethyl paraoxon yielded 4-nitro[1-¹⁴C]phenol. Paraoxon deethylation was also shown to be an important detoxication mechanism in female rats and male mice and must be considered in interpreting the toxicological properties of parathion and paraoxon.     

Alachlor influence on sorghum growth and gibberellin precursor synthesis

Growth (14 days) of sorghum (Sorghum bicolor L. cv G522 DR) from seed planted in sand into which alachlor [2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide] was uniformly incorporated (0, 0.07, 0.14, 0.28, 0.56, 1.12, 2.24, or 4.48 kg/ha) was reduced by 0.14 kg/ha and severely inhibited (88%) by 0.56 kg/ha while cellular water cotent was not greatly influenced by 0.56 kg/ha. When added into the nutrient solution bathing the roots of 96-hr sorghum seedlings, alachlor (0, 0.0156, 0.0312, 0.0625, 0.125, 0.25, 0.5, 1, 2, 4, 8, 16, 32, 64, or 128 ppmw) was not lethal to 14-day-old sorghum at rates up to 32 ppmw (92% survival); however, shoot and root lengths were reduced 43 and 58%, respectively. Alachlor inhibition of sorghum growth appears to be closely associated with inhibition of cell enlargement; the coleoptile is the most susceptible stage of sorghum growth to alachlor. This situation closely resembles growth where gibberellic acid (GA) synthesis is inhibited. [2-¹⁴C]Mevalonic acid ([2-¹⁴C]MVA) incorporation into terpenoid GA precursors was evaluated using a cell-free enzyme system from etiolated sorghum coleoptiles. Alachlor did not inhibit total ¹⁴C incorporation but incorporation of ¹⁴C into kaurenol and sterols was decreased ca 80 and 75%, respectively, by 10^?6M alachlor. Analyses for [¹⁴C]geranylgeraniol (GG), [¹⁴C]farnesol, and [¹⁴C]geraniol contents showed accumulation of [¹⁴C]farnesol and [¹⁴C]GG, and decreased [¹⁴C]geraniol. When seeds to which CGA-43089 [α-(cyanomethoximino)-benzacetonitrile] was applied 8 weeks prior to planting were substituted for untreated seeds, incorporation of [2-¹⁴C]MVA into [¹⁴C]kaurenol was increased by alachlor while [¹⁴C]GG and [¹⁴C]farnesol accumulated and [¹⁴C]geraniol was absent at 10^?6M alachlor. Additionally, sterol content increased in “safened” systems but was still decreased by alachlor. These data demonstrate multiple sites of alachlor activity in the GA and terpenoid biosynthetic pathway.     

Aerobic soil metabolism of metsulfuron-methyl

A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20°C. Both [phenyl-U-¹⁴C]- and [triazine-2-¹⁴C]metsulfuron-methyl were used. The soil was treated with [¹⁴C]metsulfuron-methyl (0.1 mg kg⁻¹) and incubated in flow-through systems for one year. The degradation rate constants, DT₅₀, and DT₉₀ were obtained based on the first-order and biphasic models. The DT₅₀ (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9–11 days, 95% confidence limits) in the non-sterile soil and 20 days (12–32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-¹⁴C] and [triazine-2-¹⁴C]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[[[[[[[(acetylamino)carbohyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[[[[[amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. © 1999 Society of Chemical Industry     

Localizing the action of two thiadiazolyl herbicidal derivatives

Enzymatically isolated leaf cells from navy beans (Phaseolus vulgaris L., cv. “Tuscola”) were used to study the effect of buthidazole (3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone) and tebuthiuron (N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-N,N′-dimethylurea) on photosynthesis, protein, ribonucleic acid (RNA), and lipid synthesis. The incorporation of NaH¹⁴CO₃, [¹⁴C]leucine, [¹⁴C]uracil, and [¹⁴C]acetic acid as substrates for the respective metabolic process was measured. Time-course and concentration studies included incubation periods of 30, 60, and 120 min and concentrations of 0.1, 1, 10, and 100 μM of both herbicides. Photosynthesis was very sensitive to both buthidazole and tebuthiuron and was inhibited in 30 min by 0.1 μM concentrations. RNA and lipid syntheses were inhibited 50 and 87%, respectively, by buthidazole and 42 and 64%, respectively, by tebuthiuron after 120 min at 100 μM concentration. Protein synthesis was not affected by any herbicide at any concentration or any exposure time period. The inhibitory effects of buthidazole and tebuthiuron on RNA and lipid syntheses may be involved in the ultimate herbicidal action of these herbicidal chemicals.     

Alkylation of guanine in mice in vivo by organophosphorus insecticides. I. Trichlorphone and butonate

Following intraperitoneal administration to male mice of trichlorphone, 4 mg/animal = 160 mg/kg and butonate, 5 and 10 mg/animal = 200 and 400 mg/kg, labeled by ¹⁴C in the OCH₃-groups, nucleic acids taken from different organs and urine were analyzed for [7-¹⁴C]methylguanine. The limit of detection was 2 × 10^?8, calculated as ¹⁴C relative to the total dose. The maximum of ¹⁴C in 7-methylguanine was 2 × 10^?7 in lung, kidney, and testicles and 3 × 10^?6 in liver. The excretion rate of 7-MeG from nucleic acids is very rapid, a halflife of 2.0 hr was measured in liver from butonate and of < 24 hr was calculated in the whole body from trichlorphone, contrary to the excretion rate of 3.0–3.5 days following administration of strongly genotoxic agents. The relative amounts of [7-¹⁴C]methylguanine excreted in the urine were determined and compared with data for dichlorvos, dimethyl sulfate, and methyl methanesulfonate from the literature. Following intraperiotoneal administration, the methylating capability towards N-7 of guanine in nucleic acids is given by the ratio of about 100:10:25 for dichlorvos, butonate, and trichlorphone, respectively.     

Comparative effects of three isoxazole-urea herbicidal derivatives on the metabolism of enzymatically isolated soybean leaf cells*

The effects of the herbicide isouron and of its plant degradation products designated as metabolite l {N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-N-methylurea} and metabolite 2 {N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-urea} on the metabolism of enzymatically isolated leaf cells of soybean [Glycine max (L.) Merr., cv. Essex] were compared under laboratory conditions. Photosynthesis, protein synthesis, ribonucleic acid synthesis, and lipid synthesis were assayed by the incorporation of NaH¹⁴CO₃, [¹⁴C]-leucine, [¹⁴C]-uracil, and [¹⁴C]-acetate, respectively, into the isolated cells. Time-course and concentration studies included incubation periods of 30, 60, and 120 min and concentrations of 0.1, 1, 10 and 100 μM of the three herbicides. The urea derivative of isouron (metabolite 2) was the least active of the three compounds. The activity of the mono-methylated derivative of isouron (metabolite 1) was comparable to that of isouron and the sensitivity of the four processes to both chemicals decreased in the order: photosynthesis > ribonucleic acid synthesis > lipid synthesis > protein synthesis. The concentration of isouron that caused a 50% inhibition of photosynthesis of the isolated soybean leaf cells was calculated at 0.51 μM. The effects of isouron and metabolite 1 on photosynthesis, lipid and RNA synthesis appeared to be independent of incubation lime as maximal inhibition occurred within 30 min. Inhibition of protein synthesis by both chemicals was time-dependent, increasing in magnitude with concomitant increases in incubation time.     

Microbial metabolism of propanil and 3,4-dichloroaniline

A Pseudomonas sp. which grew on 4-chloroaniline as a sole source of carbon and nitrogen was able to degrade 15% of 0.05 mM [¹⁴C]3,4-dichloroaniline to ¹⁴CO₂ within 10 days in presence of 1.5 mM 4-chloroaniline. The catabolic enzymes which degraded 3,4-dichloroaniline to CO₂ were inducible by 4-chloroaniline and by 3,4-dichloroaniline. However, their activity was much lower on 3,4-dichloroaniline than on 4-chloroaniline. The strain showed no significant growth on 3,4-dichloroaniline as a sole source of carbon and nitrogen. Soils supplemented with [ring-¹⁴C]propanil and the Pseudomonas sp. evolved 25–50% ¹⁴CO₂ within 5 days. The ¹⁴CO₂ evolution remained below 1% in absence of the Pseudomonas sp.     

Degradation and adsorption of carbendazim and 2-aminobenzimidazole in soil

Increasing adsorption of [¹⁴C]-labelled carbendazim in soil took place within a few weeks of incubation and was greatest in soil with a high organic matter content. Carbendazim was slowly decomposed in soil, mainly by soil microorganisms. After 250 days of incubation in two unsterilised soils, 13 and 5% respectively of added [¹⁴C]-carbendazim was recovered compared with 70 and 50% respectively from sterile soils; 4–8% of added carbendazim was recovered as 2-aminobenzimidazole (2-AB) from both unsterilised and sterile soil. After 270 days' incubation, 33 and 9% of ¹⁴C was recovered as ¹⁴CO₂ from soil supplied with [¹⁴C]-carbendazim (20 and 100 mg/kg) respectively. Degradation started more rapidly when carbendazim was added to soil preincubated with the fungicide but the degradation rate was very low in all cases, indicating that the compound is a poor microbial energy source and that the degradation is a co-metabolic process. 2-AB was found as a degradation product although it appeared to be unstable in soil, decomposing rapidly after a lag period of about 3 weeks; small amounts remained in the soil for several months, however, presumably adsorbed on soil particles.     

Fate of [14C]diflubenzuron on cotton and in soil

Aqueous suspensions and oil emulsions of a commercial [¹⁴C]diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide) formulation (Dimilin W-25) remained on the leaf surface of greenhouse-treated plant tissues. Absorption, translocation, and metabolism of the [¹⁴C]diflubenzuron were not significant. Less than 0.05% of the applied ¹⁴C was found in newly developed plant tissues 28 days after spray treatment. [¹⁴C]Diflubenzuron was degraded in soil. After 91 days, biometer flask studies showed that 28% of the ¹⁴C incorporated into the soil as [¹⁴C]diflubenzuron was recovered as ¹⁴CO₂. Major dichloromethane-soluble soil residues were identified as unreacted [¹⁴C]diflubenzuron and [¹⁴C]4-chlorophenylurea. A minor unknown degradation product cochromatographed with 2,6-difluorobenzoic acid. Insoluble ¹⁴C-residues increased with time and represented 67.8% of the residual ¹⁴C in the soil 89 days after treatment. Cotton plants grown for 89 days in [¹⁴C]diflubenzuron-treated soil contained only 3% of the ¹⁴C applied to the soil. Small quantities of acetonitrile-soluble [¹⁴C]4-chlorophenylurea were isolated from the foliar tissues. Root tissues contained small amounts of [¹⁴C]diflubenzuron and trace quantities of a minor ¹⁴C-product that chromotographed similarly to 2,6-difluorobenzoic acid. Most of the ¹⁴C in the plant tissues (84–93%) was associated with an insoluble residue fraction 89 days after treatment.     

Distribution of the radioactivity in sugar beet plants treated with [14C]aldicarb

Sugar beet plants were grown in the field, after in-furrow application of [¹⁴C]aldicarb (3 kg of aldicarb ha^?1) at planting. Some plants (the growing plants) were harvested 99 days after sowing and the rest (the ripe plants) 196 days after sowing. The percentages of the weights of [¹⁴C]aldicarb equivalents (the total aldicarb plus aldicarb sulphoxide and sulphone, plus all the other metabolites of [¹⁴C]aldicarb which contain ¹⁴C, expressed as aldicarb equivalents) incorporated into the beet plants, relative to the weight applied to the soil, were 2.8 and 1.8, respectively for the growing and ripe plants. The concentrations of [¹⁴C]aldicarb equivalents (mg kg^?1 fresh weight) in the growing and ripe plants, respectively were: blades of the external leaves, 3.16 and 0.93; blades of the internal leaves, 0.63 and 0.68; petioles of the external leaves, 0.51 and 0.26; petioles of the internal leaves, 0.15 and 0.05; crowns, 0.14 and 0.15; roots, 0.16 and 0.13. The proportions of the extractable aldicarb plus aldicarb sulphoxide and aldicarb sulphone determined by gas-liquid chromatography (expressed as aldicarb equivalents) relative to [¹⁴C]aldicarb equivalents, in the external and internal leaf blades of the growing beets, were 56 and 60%, respectively; these values declined to 25 and 19%, respectively in the ripe plants. The proportion was 21 % or less in all other parts of the growing and ripe plants.     

S-Ethyl dipropylthiocarbamate, N,N-Diallyl-2-chloroacetamide,and 2-chloroallyl diethyldithiocarbamate influence on sulfhydryl-dependent sucrose accumulation

l-[U-¹⁴C]sucrose accumulation by phloem sieve tube members (PSTM) of wheat (Triticum aestivum L. ‘Holley’) and sorghum (Sorghum bicolor L. ‘G522 DR’) was inhibited by the nonpermeant sulfhydryl inhibitor p-chloromercuribenzenesulfonic acid (PCMBS), and this inhibition was reversed by the permeant sulfhydryl protectants dithiothreitol (DTT) and dithioerythritol (DTE). S-Ethyl dipropylthiocarbamate (EPTC) (≤0.1 mM) did not inhibit [¹⁴C]sucrose accumulation by wheat or sorghum PSTM. N-N-Diallyl-2-chloroacetamide (CDAA) (1 mM) inhibited [¹⁴C]sucrose accumulation by sorghum but not by wheat PSTM. The inhibition of [¹⁴C]sucrose accumulation in sorghum PSTM by the membrane permeant CDAA was reversed by DTT. Sorghum growth was inhibited by <1 μM CDAA. Membrane permeant 2-chloroallyl diethyldithiocarbamate (CDEC) (0.1 mM) inhibited [¹⁴C]sucrose accumulation by PSTM of sorghum but not wheat. The inhibition of sucrose accumulation in sorghum PSTM by 0.1 mM CDEC was reversed by DDT.     

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).     

Characterization of residues in soybeans grown in soil treated with 1,3-dichloropropene soil fumigant

The metabolism of cis- and trans-1,3-dichloropropene (1,3-D) was studied in soybean plants grown in soil treated 24 days prior to planting with [U-¹⁴C]E- and Z-1,3-dichloropropene at 380 liters ha^?1. Isolation and identification of the ¹⁴C residue from soybean plants at 84 days (forage) and 176 days (mature) after application showed that no 1,3-dichloropropene or its putative metabolites, 3-chloroallyl alcohol and 3-chloroacrylic acid, could be detected in any of the tissues. The components of the ¹⁴C residue included major plant constituents (i.e. fatty acids, protein, pigments, organic acids, sucrose and other carbohydrates, and lignin).     

Influence of nitrogen fertilisers on the persistence of carbaryl and carbofuran in flooded soils

Ammonium sulphate and urea, but not potassium sulphate, increased the persistence of carbaryl in a flooded laterite soil with a low native nitrogen content (0.04%), but not in an alluvial soil with a higher nitrogen content (0.11%). Thus, NH₄⁺ but not SO₄^2-, contributed to the increased persistence of carbaryl. Likewise, ammonium sulphate increased the persistence of carbofuran in the laterite soil, but not in the alluvial soil. Significant accumulations of 1-naphthol and 2,3-dihydro-2, 2-dimethylbenzofuran-7-ol (‘carbofuran phenol’), in soils treated with carbaryl or carbofuran, suggested hydrolysis as the major pathway of degradation. Treatment of the two soils with ammonium sulphate, urea or potassium sulphate led to a decrease in soil-bound residues and an increase in the respective hydrolysis products, compared with untreated soils. Sorption studies indicated that NH₄⁺ and SO₄^2- compete with carbaryl, 1-naphthol and carbofuran for sorption and exchange sites in the complex soil system. Evolution of [¹⁴C]carbon dioxide from ring-¹⁴C in carbaryl and carbofuran was negligible. Consequently, after 40 days, more than 50% of the ¹⁴C in [¹⁴C]carbaryl and [¹⁴C]carbofuran remained in the soils as hydrolysis products (1-naphthol or 2,3-dihydro-2,2-dimethylbenzofuran-7-ol) plus soil-bound residues.     

Absorption, translocation and metabolism of metamitron in Chenopodium album

BACKGROUND: In recent years, common lambsquarters (Chenopodium album L.) populations from sugar beet fields in different European countries have responded as resistant to the as‐triazinone metamitron. The populations have been found to have the same D1 point mutation as known for atrazine‐resistant biotypes (Ser₂₆₄ to Gly). However, pot experiments revealed that metamitron resistance is not as clear‐cut as observed with triazine resistance in the past. The objectives of this study were to clarify the absorption, translocation and metabolic fate of metamitron in C. album. RESULTS: Root absorption and foliar absorption experiments showed minor differences in absorption, translocation and metabolism of metamitron between the susceptible and resistant C. album populations. A rapid metabolism in the C. album populations was observed when metamitron was absorbed by the roots. The primary products of metamitron metabolism were identified as deamino‐metamitron and metamitron‐N‐glucoside. PABA, known to inhibit the deamination of metribuzin, did not alter the metabolism of metamitron, and nor did the cytochrome P450 inhibitor PBO. However, inhibition of metamitron metabolism in the presence of the cytochrome P450 inhibitor ABT was demonstrated. CONCLUSION: Metamitron metabolism in C. album may act as a basic tolerance mechanism, which can be important in circumstances favouring this degradation pathway. Copyright © 2011 Society of Chemical Industry