Response of spring cereal crops to soil residues of ethofumesate*

For evaluation of soil residues of ethofumseate [(±)2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl-methylsulphonate], spring barley (Hordeum vulgare L.) and spring wheat (Triticum aestivum L.) were sown in soil planted 11 months previously with sugar-beet (Beta vulgaris L.) and previously treated with band or broad-cast applications of the herbicide at rates of 1.68-4.48 kg/ha. The height of barley and wheat was suppressed only where ethofumesate was applied broadcast and the soil was not ploughed after sugar-beet harvest. Three months after sowing, the 4.48 kg/ha rate suppressed the height of barley 18% and wheat 34%. In another experiment, barley grew normally on soil treated the previous year with pre-planting and post-emergence applications of ethofumesate where ploughing followed sugar-beet harvest. For all treatments, yields of straw and grain were not significantly lower than those of the untreated check plots. The dissipation of ethofumesate 24 weeks after application to sugar-beet was 89–100% when applied on a band compared to 85-95% when applied broadcast.     

Absorption and translocation of 14C-3,6-dichloropicolinic acid in Cirsium arvense (L.) Scop.

Experiments were conducted in a growth cabinet to investigate the absorption and translocation of ¹⁴C-3, 6-dichloropicolinic acid by Cirsium arvense (L.) Scop. (Canada thistle, creeping thistle), a sensitive species. Applications were made, either to the middle four leaves of 12-cm-tall vegetative plants grown under low (40%) and/or high (>95%) relative humidity (r.h.), or to four upper or lower leaves of 30-cm-tall flowering plants grown under low r.h. Following application to vegetative plants, absorption and translocation of ¹⁴C-3,6-dichloropicolinic acid was rapid and was approximately doubled by high r.h. High r.h. increased the amount of radioactivity retained by the treated leaves or translocated to the shoots but did not affect greatly the amount retained in the roots. The herbicide was highly mobile, with over half of that absorbed, translocated out of the treated leaves after two days. The apex accumulated most of the radioactivity, while approximately 8% was recovered from the roots. The absorption and translocation patterns were similar to those reported in the literature for picloram in C. arvense. Absorption of 3,6-dichloropicolinic acid was greater in vegetative than in flowering C. arvense plants, and placement of herbicide on lower leaves tended to decrease the amount of radioactivity recovered from shoot apex and increase the amount recovered from the roots. Approximately 15% of the applied radioactivity could not be recovered from treated plants by 2 days after treatment.     

三唑酮及其代谢产物三唑醇在橡胶树植株中的迁移富集行为

三唑酮是一种重要的橡胶树白粉病防治药剂,明确三唑酮及其代谢物三唑醇在橡胶树上的迁移富集行为有利于提高其农药的靶标利用率。本研究基于QuEChERS法,采用气相色谱-串联质谱(GC-MS/MS)技术首次建立了三唑酮和三唑醇在橡胶树植株根、茎、叶中的残留分析方法。采用水培条件下根部施药和土培条件下叶部施药的方式,分别研究了三唑酮及三唑醇在橡胶树植株中的迁移富集行为。结果表明：橡胶树植株可快速将三唑酮代谢成三唑醇,2种药剂均可从植株根部通过茎部迁移至叶部,但在植株各部位中的富集行为具有较大差异,其生物富集系数大小依次为根部>茎部>叶部,且茎部和叶部的转运系数均小于1,表明三唑酮及三唑醇很难在橡胶树植株中向上迁移,易被根部富集;在对橡胶树植株叶部施药时,三唑酮亦可快速代谢成三唑醇,2种农药在植株不同部位的叶片间迁移能力较差。该研究可为优化三唑酮等农药在橡胶树上的施用方案提供重要的数据支撑。     

The foliar uptake of isoproturon by wheat and Alopecurus myosuroides huds

The uptake and translocation of ¹⁴C-isoproturon (3-p-cumenyl-1-1,-dimethylurea) in wheat (tolerant) and backgrass (sensitive) following foliar treatment under controlled environmental conditions were examined. The amount of ¹⁴C-isoproturon translocated through the xylem was about 10 times that translocated through the phloem in both wheat and blackgrass. However, 25.5% of the applied ¹⁴C-isoproturon was translocated in the xylem in blackgrass, compared with 8.9% in wheat. ¹⁴C-isoproturon did not respond significantly to induced sink-demand in either species. Leaf-disc autoradiograms revealed the absorption of ¹⁴C-isoproturon by the minor veins and translocation into the cut vein endings. No significant differences were found in between wheat and blackgrass in this respect.     

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.     

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.     

INVESTIGATIONS ON SKELETON WEED (CHONDRILLA JUNCEA L.) WITH PICLORAM AND 2,4-D

Summary. Picloram is decarboxylated to a negligible extent in roots of skeleton weed: applied to leaves it kills roots better than 2,4-D; it penetrates leaves better than 2,4-D and disrupts the translocation system more, does not leak considerably into the soil from roots by the time of appropriate harvests, yet is not as well translocated as 2,4-D. Under such conditions its ability to kill roots to a greater depth is attributable to its greater intrinsic toxicity.
There is some evidence that under certain field conditions useful movement or uptake of picloram may occur via the soil.
Recherches sur Chondrilla juncea L . avee le plclorame et le 2,4-D.     

Factors affecting benfuresate activity against purple nutsedge (Cyperus rotundas L.)

Benfuresate (2-3-dihydro-3,3-dimethylbenzofu-ran-5-yl ethanesulfonate) is a selective herbicide for the control of purple nutsedge in cotton. Under outdoor conditions, purple nutsedge was sensitive to benfuresate incorporated in soil up to eight days after initiation of shoot sprouting from the tuber. Older seedlings recovered from the damage. During the period of susceptibility to benfuresate, young shoots more sensitive than the roots. Under controlled environmental conditions, benfuresate applied directly to apical buds developing from the tuber caused severe damage to the treated bud and induced abrupt development of axillary buds. Negligible amounts of the applied herbicide were translocated from the treated part to the other buds and roots. Application of the herbicide to fully developed leaves had no effect, probably because of its rapid metabolism and low basipetal mobility. Its relatively high volatility may also contribute to its low foliar post-emergence activity. Tubers also absorbed herbicide vapours. Root uptake of ¹⁴C-benfuresate resulted in a rapid accumulation of ¹⁴C in the shoot, which had no effect on the purple nutsedge plant, regardless of concentration. The herbicide is rapidly converted, mainly to a non-phytotoxic polar product. These results may explain the high sensitivity of the weed to benfuresate at early growth stages, and the lack of sensitivity in mature plants.     

Atrazine soil metabolism in maize fields treated with organic fertilizers

The metabolism of atrazine in soil was studied in two maize fields located in regions with different soil types. Treatments were cow manure or pig slurry (50 tonnes each ha^-1) applied once either in March or in November before sowing, or green manure incorporated in March. Control plots were not treated with organic fertilizers. Atrazine at 0.75 or 1.0 kg a.i. ha^-1 was applied after sowing. In the 0-12 cm soil layer, the main atrazine metabolites found were deethylatrazine and hydroxyatrazine. Low concentrations of deisopropylatrazine and 6-chloro-1, 3, 5-triazine-2, 4-diamine were also observed. During the 4 months after sowing, the organic fertilizers decreased the rate of atrazine degradation, but subsequently there were no differences between treated and control plots. At harvest, the concentrations of atrazine and its metabolites were very low and similar in all plots. The organic fertilizers thus did not cause atrazine metabolites to accumulate in soil. In addition, atrazine and its metabolites were never detected below 12 cm in any of the plots.     

Comparison of foliar and soil formulations of neonicotinoid insecticides for control of potato leafhopper, Empoasca fabae (Homoptera: Cicadellidae), in wine grapes

BACKGROUND: The potential of systemic neonicotinoid insecticides to control potato leafhopper, Empoasca fabae (Harris), a damaging pest of wine grapes in the eastern United States, was investigated. Soil or foliar applications were made to potted or field‐grown vines, and the response of leafhoppers was determined in clip cages over the following month on young or mature leaves. RESULTS: Foliar application of imidacloprid caused immediate and long‐lasting reductions in E. fabae survival on both leaf ages, whereas the activity of soil‐applied imidacloprid was delayed. Clothianidin, imidacloprid and thiamethoxam all provided long‐lasting reduction in leafhopper survival on young and mature foliage when applied through either delivery route. However, the percentage of moribund nymphs was significantly greater on foliar‐treated vines and increased over time in mature and immature leaves compared with soil‐treated vines. Residue analysis of foliar‐applied imidacloprid showed an 89% decline in mature leaves from day 1 to day 27, and a 98% decline in immature leaves over the same time period. Comparison of soil‐applied clothianidin, imidacloprid and thiamethoxam in field‐grown vines showed significant reduction in E. fabae only on mature leaves of vines treated with thiamethoxam. CONCLUSIONS: Neonicotinoids can control E. fabae in small vines, even in rapidly expanding foliage where this pest causes greatest injury. Soil application provides superior long‐term vine protection because declining residues on foliar‐treated vines lead to suboptimal activity within 2–3 weeks. Vineyard managers of susceptible cultivars may take advantage of this approach to E. fabae management by using foliar applications of the three neonicotinoids tested here, or by using soil‐applied thiamethoxam. Copyright © 2011 Society of Chemical Industry     

Comparison of the uptake, movement and metabolism of fluroxypyr in Stellaria media and Viola arvensis

The uptake, movement and metabolism of fluroxypyr* is compared in two contrasting weed species, Stellaria media (susceptible) and Viola arvensis (moderately resistant). Similar rates of uptake occurred in both species, with a rapid cuticular uptake of 50% of that applied within 4 h. Total uptake by the underlying leaf tissue reached 66.6% and 70.8% in S. media and V. arvensis after 7 days. In translocation studies, in which ¹⁴C-fluroxypyr was applied to previously sprayed plants, 5.1% of applied ¹⁴C-activity was translocated from the treated leaves of S. media after 1 day, which increased to 42.2% after 7 days, recovered mainly from the stem tissue. In V. arvensis translocation was similar after 24 h however, after 7 days over 40% of applied ¹⁴C-activity remained in the treated leaves and only 9.7% was translocated, mainly to the developing leaves and apical tissue. ¹⁴C-activity extracted from the cuticle was the methylheptyl ester of fluroxypyr in both species. In the treated leaves and apical tissue, ¹⁴C-activity was the free acid of fluroxypyr and polar conjugates with a significantly greater proportion of the acid in S. media. It is concluded that the resistance or V. arvensis is partially due to reduced translocation and greater conjugation than in the susceptible S. media.     

Physiological basis of bentazon tolerance in rice (Oryza sativa L.) lines

In the present study, 98.8 mm of bentazon was applied to 3‐leaf stage rice seedlings. Two tolerant lines, M202 and cv. TNG67, showed slightly visible injury, photosystem II inhibition, as well as a low level of lipid peroxidation 7 days after application compared with the susceptible lines. Further physiological study of the mechanism of differential tolerance among Japonica and Indica types indicated that, although the tolerant Japonica lines M202 and cv. TNG67 absorbed more ¹⁴C‐bentazon, most of the ¹⁴C remained in the treated leaf or translocated to older leaves. However, two susceptible lines, FSK (Japonica) and IR36 (Indica), absorbed less ¹⁴C‐bentazon throughout the experiment, and most of the ¹⁴C was translocated from the treated leaves to younger leaves, which might result in the death of developing tissues. In addition, more bentazon residue and less polar metabolites were detected in these two susceptible lines. It is proposed that the higher tolerance of lines M202 and TNG67 to bentazon could be mainly due to a higher rate of metabolism of this herbicide, and partially due to less translocation to developing tissues.     

Selectivity factors relative to asulam for Senecio jacobaea L. control in Medicago sativa L. I. Retention,uptake and translocation*

Senecio jacobaea L. and Medicago sativa L. plants grown in a glasshouse were treated with foliar applications of aqueous solutions of asulam. Retention on foliage, uptake and translocation were measured in both species. Retention was greater in S. jacobaea than in M. sativa when no surfactant was added and similar when surfactant was added. Addition of surfactant modified spray distribution and increased asulam uptake in M. saliva but did not in S. jacobaea. S. jacobaea translocated over twice as much asulam from the treated area as M. sativa. These data suggest that surfactant should not be added for maximum selectivity. Differences in species response to asulam treatments are partially, but not entirely, explained by differences in retention, uptake and translocation.     

Movement of phorate and metabolites from treated leaflets to aphid colonies on broad bean plants

Aphid colonies were established on one second-node leaflet of young broad bean plants and sublethal treatments of ¹⁴C-labelled phorate were applied to the adjacent leaflets. After 3 days, the amounts of toxic and non-toxic ¹⁴C-labelled compounds in the aphids, their honeydew and the untreated foliage were determined. There were no significant differences between the amounts in leaves at the same level on the plant when infested and aphid-free plants were compared, but the aphids and their honey-dew contained two and 23 times as much of the toxic and non-toxic ¹⁴C-compounds, respectively, found in the host leaflets. Following translocation to aphids on leaves above or below treated leaflets, the aphid colonies again contained more labelled compounds than the host-plant leaves. The movement of non-toxic compounds into the roots was reduced when the aphid colonies were situated on foliage between the site of treatment and the roots. More of the toxic and the non-toxic fractions were translocated downwards from the third to the second leaf than in the reverse direction.     

STUDIES ON HERBICIDE CONTENTS IN ROOTS OF SKELETON WEED (CHONDRILLA JUNCEA L.) FOLLOWING LEAF APPLICATIONS

Summary. The herbicides studied were 2,4-D, 2,4-DB, dicamba and orthoarsenic acid. Herbicide content in the roots was taken as an overall measure of penetration into and absorption by the leaves, and of translocation to the roots.
A significantly greater 2,4-D content resulted from foliar application at pH 3–5 than at higher values, though at pH 8–5 the inclusion of triethanolamine significantly increased the 2,4-D content. No evidence was obtained that a greater 2,4-D content should result from foliage applications of 2,4-DB than from 2,4-D. Dicamba gave a greater herbicide content than 2,4-D when applied at high concentration at 20° C but not at 25° C, probably because of less injury at the lower temperature.
Concentrations of Tween 20 up to 2% had no deleterious effect on the 2,4-D content; on the other hand 2,4-D content was lowered by 0–25% or more of cetyltrimethyl-ammonium bromide. Poor wetting is not the cause of the variable herbicide contents sometimes obtained.
Orthoarsenic acid, which has given better control of the weed than 2,4-D, was very poorly translocated; its effectiveness is due to its high intrinsic toxicity.
Etudes sur la teneur en herbicide des racines de Chondrilla juncea L. á la suite d'applications sur les feuilles     

Uptake and translocation of some pesticides by hypocotyls of radish seedlings

Some of the factors affecting absorption and translocation of pesticides by the hypocotyls of intact radish (Raphanus sativus, L., cv. Black Spanish) seedlings have been studied, particular attention being given to the triazine herbicides simazine, atrazine and atraton. Uptake and translocation appear to be largely passive processes and by contrast with foliar absorption seem to be unaffected by humidity, con-centration, light and by the aqueous solubilities of the compounds. Diffusion across the tissues of the hypocotyl, rather than rate of transpiration, appears to determine the rate at which atrazine and simazine are translocated to the cotyledons. For several pesticides there is a qualitative relationship between the percentages of the compounds translocated to the upper portion of the shoots and their partition coefficients in oil/water systems. In conclusion, some consideration is given to the relative importance of uptake by roots and shoots under field conditions.     

Environmental behaviour and translocation of imidacloprid in eggplant,cabbage and mustard

The recently registered insecticide, imidacloprid, was applied to three vegetable crops at 20 and 40 g AI ha⁻¹. The persistence of the parent insecticide and its translocation, along with the quantification of the metabolites formed on these crops are presented. The parent insecticide dissipated with a half‐life of 3–5 days and persisted longest on mustard leaves. The detectable limit of the HPLC method was 0.01 µg g⁻¹. The metabolites 1‐(6‐chloropyridin‐3‐yl‐methyl)imidazolidin‐2‐one and 6‐chloronicotinic acid were found to be translocated by day 10 in eggplant, cabbage leaves and mustard leaves but not in cabbage curd. The MRL of imidacloprid is not documented by the FAO/WHO on these crops and comparison of the MPI with the TMRC, calculated on the residue data generated in this study, establishes the safety of the schedule. © 2000 Society of Chemical Industry     

Fate of [14C]daminozide and [14C]maleic hydrazide in American elm (Ulmus americana L.)

Radiolabelled daminozide and maleic hydrazide (MH) were injected into American elm seedlings, kept in nutrient solution, to determine their translocation pattern and metabolic fate. Both compounds were rapidly translocated to all parts of the plant. After 21 days, 13% of the applied ¹⁴C was exuded into the nutrient solution from the roots of the plants treated with MH. Using gel-filtration and thin-layer chromatographic techniques, it was determined that daminozide did not form any metabolite, and that MH was converted into a MH-sugar complex. A significant amount of ¹⁴C was unextractable from the plant tissue.     

Translocation and degradation of pyrazosulfuron-ethyl in rice soil

BACKGROUND: Pyrazosulfuron‐ethyl {ethyl 5‐[(4,6‐dimethoxypyrimidin‐2‐ylcarbamoyl)‐sulfamoyl]‐1‐methylpyrazole‐4‐carboxylate} is a new rice herbicide belonging to the sulfonylurea group. This study reports the translocation of ¹⁴C‐pyrazosulfuron‐ethyl to rice plants and its degradation in rice‐planted and unplanted soil. RESULTS: Pyrazosulfuron‐ethyl did not show any appreciable translocation to rice shoots, as ¹⁴C‐activity translocated to the aerial portion never exceeded 1% of the initially applied ¹⁴C‐activity over a 25 day period. Results suggested that the dissipation of pyrazosulfuron‐ethyl from soils followed first‐order kinetics with a half‐life of 5.5 and 6.9 days in rice‐planted and unplanted soils respectively. HPLC analysis of the organic extract of soil samples showed the formation of three metabolites, namely ethyl 5‐(aminosulfonyl)‐1‐methyl‐1‐H‐pyrazole‐4‐carboxylate, 5‐[({[(4,6‐dimethoxy‐2 pyrimidinyl)‐amino]‐carbonyl} amino)‐sulfonyl]‐1‐methyl‐1H‐pyrazole‐4‐carboxylic acid and 2‐amino‐4,6‐dimethoxy pyrimidine, in both rice‐planted and unplanted soils. CONCLUSION: The study indicates that pyrazosulfuron‐ethyl was a short‐lived compound in the soil and was degraded relatively faster in rice‐planted soil than in unplanted soil. The herbicide did not show any appreciable translocation to rice plants. Copyright © 2011 Society of Chemical Industry     

Soybean shoot metabolism of isopropyl-3-chlorocarbanilate: Ortho and para aryl hydroxylation

This laboratory reported that isopropyl-3-chlorocarbanilate-phenyl-U-¹⁴C (chlorpropham-phenyl-¹⁴C) was absorbed, translocated, and metabolized by soybean plants. Both polar metabolites and insoluble residues were found in roots, whereas only polar metabolites were found in shoot tissues. In both roots and shoots the polar metabolites were shown to be the O-glucoside of isopropyl-2-hydroxy-5-chlorocarbanilate (2-hydroxy-chlorpropham). In shoot tissue there were other polar metabolites that were not identified. The experiments with soybeans have been repeated, but with new isolation and purification procedures. The plants were root treated with both chlorpropham-phenyl-¹⁴C and isopropyl-3-chlorocarbanilate-2-isopropyl-¹⁴C. The roots and shoots were extracted and separated into the polar, nonpolar, and insoluble metabolic components, using the Bligh-Dyer extraction method. The polar metabolites were separated by gel permeation chromatography. Further purification was accomplished on Amberlite XAD-2. The polar metabolites from the shoot and root tissues were hydrolyzed either by β-glucosidase or hesperidinase. The enzyme liberated aglycones were derivatized and separated by gas-liquid chromatography, and the components were characterized by mass spectrometry or NMR. The results of this study showed that the polar metabolites of soybean shoots were 2-hydroxy-chlorpropham and isopropyl-4-hydroxy-3-chlorocarbanilate (4-hydroxy-chlorpropham). These two hydroxy-chlorpropham metabolites were found in soybean shoots at a ratio of approximately 1:1. The only aglycone found in root tissue was 2-hydroxy-chlorpropham. Using the new procedures, no evidence was obtained for the presence of the unidentified polar metabolites that were previously observed in shoot tissues.