Comparative uptake and metabolism of methazole in prickly sida and cotton

The comparative uptake and metabolism of ¹⁴C-labeled 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione (methazole), a herbicide, in prickly sida (Sida spinosa L.) and cotton (Gossypium hirsutum L.) were investigated as physiological bases for herbicidal selectivity, using thin layer chromatography, autoradiography, and liquid scintillation counting. Prickly sida and cotton readily absorbed and translocated ¹⁴C from nutrient solution containing [¹⁴C]methazole. Only acropetal translocation of ¹⁴C was observed. Methazole was rapidly metabolized to 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU) and other metabolites by both species. Although metabolism appeared to be qualitatively the same, quantitative differences between species were evident. Methazole was converted to DCPMU (also phytotoxic) more readily by prickly sida than cotton; however, DCPMU was more readily detoxified to 1-(3,4-dichlorophenyl) urea (DCPU) by cotton than prickly sida. More ¹⁴C per unit weight was present in the prickly sida shoots than in cotton shoots. Also, a larger portion of the methanol-extractable ¹⁴C was herbicidal in the shoots of prickly sida than of cotton. Thus, the differential tolerances of prickly sida and cotton to methazole may be explained, in part, by differential uptake and metabolism of methazole and DCPMU.     

The degradation of methazole in soil. II. Studies with methazole,methazole degradation products and diuron

[¹⁴C]-Labelled methazole, 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU), 1-(3,4-dichlorophenyl)urea (DCPU), and diuron were incubated in soil at 20°C and field capacity soil moisture content. Decomposition followed first-order kinetics; half-lives for degradation of these four compounds were 2.4, 144, 30 and 108 days respectively. The amount of DCPMU and DCPU that could be extracted decreased with time and the decrease was accompanied by the generation of an equivalent amount of ¹⁴CO₂. This was not so in the studies with diuron and methazole, however, and the decrease in the concentrations of radioactivity extracted from soil treated with these compounds could not be entirely accounted for as carbon dioxide. It is concluded that the unextractable radiochemical that was present was DCPMU. Methazole appeared to be degraded through DCPMU to 3,4-dichloroaniline (DCA) with the production of only traces of DCPU.     

Aspects of the selective phytotoxicity of methazole. HI. Behaviour in plants following foliar treatment

Absorption of methazole by leaves of onion (Allium cepa), Stellaria media, Matricaria matricarioides and Veronica persica was rapid for the first 24 h after treatment and continued at a slower rate for up to 6 days to reach a maximum of between 35 and 60% of the amount applied. Differences in absorption between species were generally small. Absorption by the cotyledon of onion was greater than absorption into true leaves. Methazole on the leaf surface degraded to 3-(3,4-dichlorophenyl)-1-methylurea (DCPMU) and small amounts of this degraded to 3-(3,4-dichlorophenyl) urea (DCPU). Methazole absorbed into leaves was relatively stable in M. matricarioides and DCPMU accumulated slowly. The rate of degradation was more rapid in the cotyledons than in the true leaves. Both in leaves and in cotyledons of onion and S. media, methazole degraded rapidly to DCPMU and this accumulated; in those of V. persica, DCPMU was degraded quickly to DCPU and unidentified products. The amount of DCPMU accumulated in the shoots was broadly correlated with the relative phytotoxicity of methazole to the different species, except for young seedlings of V. persica which contained no DCPMU but were susceptible to methazole.     

Aspects of the selective phytotoxicity of methazole. II. Behaviour in plants following root exposure

The absorption, translocation and degradation of methazole were examined in onion, Stellaria media, Matricaria matricarioides and Veronica persica grown in culture solution. After a short period of initial rapid uptake, all four species absorbed herbicide and water in the same proportions. Translocation of herbicide to the shoots was directly proportional to transpiration, but the apparent solute concentration in the xylem was less than that in the external solution and varied between the species. A smaller percentage of the total absorbed herbicide was translocated to the shoot in V. persica, the most tolerant species. Methazole was relatively stable in M. matricariodes and was degraded slowly to 3-(3,4-dicnlorophenyl)-1-methylurea (DCPMU). It was degraded rapidly to DCPMU in the other three species and this accumulated in onion and S. media. In V. persica DCPMU was degraded further to 3-(3,4-dichlorophenyl) urea (DCPU). Methazole was not an active inhibitor of photosynthesis by isolated spinach chloroplasts. Both DCPMU and DCPU inhibited photosynthesis but DCPMU was 200-times more active than DCPU. Variations in the concentrations of DCPMU in the shoots of the different species largely accounted for the variations in their response to methazole applied pre-emergence.     

The degradation of methazole in soil. I. Effects of soil type,soil temperature and soil moisture content

[¹⁴C]-Labelled methazole was incubated in six soils at 25°C and with soil moisture at field capacity. Under these conditions, methazole was unstable, the concentration declined following first-order kinetics with half-life values in the soils ranging from 2.3 to 5.0 days. The main degradation product was 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU) which was more stable than the parent compound. After about 160 days, DCPMU accounted for 30 to 45% of the initial methazole concentration. Degradation of methazole and DCPMU was affected by soil temperature and moisture content. With methazole, half-lives in one soil at field capacity moisture content and temperatures of 25, 15 and 5°C were 3.5, 8.7 and 31.1 days respectively. The half-life at 25°C was increased to 5.0 days at 50% of field capacity and 9.6 days at 25% of field capacity. A proportion of the initial radioactivity added to the soil could not be extracted and this proportion increased with time. After 160 days this unextractable radioactivity accounted for up to 70% of the amount applied.     

Growth and reproduction of Cyperus esculentus L. and Cyperus rotundus L.

The growth of both species (as characterized by their total dry weight, inflorescence dry weight, root and rhizome dry weight and number of shoots per pot) was similar, but they differed in the manner in which the dry weight was partitioned to reproductive structures. Each species partitioned less than 2% of its dry weight into floral formation. However, yellow nutsedge (Cyperus esculentus L.) partitioned only 28% of its dry weight to tubers, whereas purple nutsedge (C. rotundus L.) partitioned 50% of its dry weight to fewer and larger tubers. The allocation of dry weight to reproductive structures was related to changes in day-length. Yellow nutsedge tuber formation increased as day-length decreased from 14.5 to 12.5 h, while floral formation did not begin until the day-length dropped below 14 h. Purple nutsedge formed inflorescences earlier and production continued throughout the remainder of the study, but tuber formation was curvilinear and accelerated as the day-length decreased.     

Metabolic fate of bioxone in cotton

The metabolic fate of the ¹⁴C-labeled herbicide, 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione (bioxone), in cotton (Gossypium hirsutum L. “Acala 4-42-77”) was studied using thin-layer chromatography, autoradiography, and counting. Bioxone-¹⁴C was readily metabolized by cotton tissue to 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU) and 1-(3,4-dichlorophenyl)urea (DCPU). Leaf discs metabolized bioxone-¹⁴C rapidly; 12 hr posttreatment, 65% of the ¹⁴C in methanol extracts was in forms other than intact herbicide. Excised leaves treated through the petiole with either heterocyclic ring-labeled or phenyl ring-labeled herbicide contained little bioxone-¹⁴C after 1 day; DCPMU was formed early then decreased with time. DCPU accounted for 55–70% of the ¹⁴C in excised leaves 3 days posttreatment. In intact plants treated via the roots, the herbicide was rapidly metabolized in the roots to DCPMU and DCPU; little or no intact herbicide was translocated to the leaves. Little radioactivity accumulated in the roots with time; the radioactivity in the leaves accounted for 80–90% of the methanol-soluble ¹⁴C 47 days posttreatment. Most of the ¹⁴C in the leaves was recovered as DCPU (50–60%) and unidentified polar metabolite(s) which remained at the origin of the thin-layer plates (30–40%). The percentage of radioactivity which remained in cotton residue after methanol extraction increased with time. Digestion of the plant residues with the proteolytic enzyme pronase indicated that some of the nonextractable ¹⁴C may be DCPMU and DCPU complexed with proteins. Similar metabolic patterns were noted after treatment with either heterocyclic ring-labeled or phenyl ring-labeled bioxone-¹⁴C. Generally, bioxone was metabolized to DCPMU which in turn was demethylated to DCPU. The herbicide and DCPMU were 20 times as toxic as DCPU to oat (Avena sativa L.), a susceptible species.     

Control of purple nutsedge (Cyperus rotundus) in cotton with benfuresate

The herbicide benfuresate applied preplanting to cotton (Gossypium hirsutum L.) fields infested with purple nutsedge (Cyperus rotundus L.) inhibited nutsedge growth for several weeks and was found selective for cotton. The best nutsedge control was achieved when the herbicide was mechanically incorporated following a preplant broadcast or band application which was activated by a sprinkler irrigation. The rate of benfuresate needed for effective and selective nutsedge control in cotton ranged from 0.80 to 1.60 kg/ha, the higher rates necessary in soils with higher clay and organic matter contents.     

EFFECT OF MINIMUM SOIL TEMPERATURE ON DIFFERENTIAL DISTRIBUTION OF CYPERUS ROTUNDUS AND C. ESCULENTUS IN THE UNITED STATES*

Summary. The response of tubers to low temperatures was investigated to gain insight into a physiological basis for the differential distribution of Cyperus esculentus L. (yellow nutsedge) and C. rotundus L. (purple nutsedge) in the United States. Only C. esculentus tubers survived the winter of 1968–69 in the field at Urbana, Illinois. Less than 10% of C. rotundus tubers survived at 2°C for 12 weeks, whereas more than 95% of C. esculentus tubers survived this treatment. Exposures to -2°C for 4 h or longer killed 50% of C. rotundus tubers, whereas - 6·5°C was required to kill 50% of C esculentus tubers. C. rotundus distribution is restricted to regions where the soil seldom freezes, whereas C. esculentus is distributed in regions where the soil temperatures often get below freezing. Survival of C. esculentus tubers in soil which frequently freezes may account for its wide distribution. Death of C. rotundus tubers in soils which freeze apparently is the reason why the species is restricted to the southeastern and southwestern regions of the U.S.A. L'Influence de la température du sol sur la répartition différentielle de Cyperus rotundus et de Cyperus esculentus aux Etats-Unis     

Factors affecting glyphosate activity in Imperata cylindrica (L) Beau, and Cyperus votundus L. I. Effect of soil moisture

Established Greenhouse grown plants of cogongrass Imperata cylindrica (L) Beauv.) and purple nutsedge (Cyperus rotundusL.) were given three different soil moisture regimes; field capacity, moderate stress and extreme stress, followed 6 weeks later by glyphosate [(N-phosphonomeihyl) glydne] applications to the shoots at 0.2,0.4 and 0.8 kg/ha for Imperata and 0.3,0.6 and 1.12 kg/ha for Cyperus. Field capacity watering stimulated most vegetative growth in hoth species. Glyphosate given at field capacity decreased shoot dry weight in both species, and rhizome length, rhizome dry weight and total carbohydrate in Imperata and total number of tuber-bulbs in Cyperus. In contrast. at extreme soil moisture stress, glyphosate showed reduced activity which appeared to be related to the physiological and morphological behaviour of the plants arising from the drought trealment. Application of waier to the roots of the plants grown at soil moisture stress. I week before and I week afler glypbosate spraying, enhanced glyphosate activity, probably because of the recovery of processes disturbed by ibe soil moisture deficit.     

Degradation of the herbicide benzoylprop-ethyl in soil

The degradation of [¹⁴C] benzoyl prop ethyl (SUFFIX,^a ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate) in four soils has been studied under laboratory conditions. The major degradation product of benzoylprop ethyl at up to 4 months after treatment was its corresponding carboxylic acid (II). On further storage this compound became firmly bound to soil before it underwent a slow debenzoylation process which led to the formation of a number of products including N-3,4-dichlorophenylalanine (IV), benzoic acid, 3,4-dichloroaniline (DCA), which was mainly present complexed with humic acids, and other polar products. Although these polar products were not identified, they were probably degradation products of DCA, since they were also formed when DCA was added to soil. No 3,3′,4,4′-tetrachloroazobenzene (TCAB) was detected in any of the soils at limits of detectability ranging from 0.01-0.001 parts/million. Since N-3,4-dichlorophenylalanine (IV) and 3,4-dichloroaniline were transient degradation products of benzoylprop ethyl, the metabolism in soil of radiolabelled samples of these compounds was also studied. In these laboratory experiments the persistence of the herbicide increased as the organic matter content of the soil increased and the time for depletion of half of the applied benzoylprop ethyl varied from 1 week in sandy loam and clay loam soils to 12 weeks in a peat soil.     

Crop rotation effects on Cyperus rotundus and C. esculentus population dynamics in southern California vegetable production

Control options for Cyperus rotundus and Cyperus esculentus (purple and yellow nutsedge) were evaluated within three cropping systems in the low desert of southern California: (1) standard vegetable crop rotation (weed‐free, uncontrolled nutsedge and cultivation) with spring cantaloupe (Cucumis melo) – summer fallow – winter broccoli (Brassica oleracea), (2) cover crop rotation (halosulfuron and smother crop) with spring wheat (Triticum aestivum)/corn (Zea mays) – summer sudangrass (Sorghum sudanense) – Winter Fallow, (3) rotation with solarization (non‐solarization and solarization) with spring wheat – summer fallow/solarization – winter broccoli. After two growing seasons, broccoli was planted without Cyperus control, to study the effect on yield. Cyperus rotundus tubers increased from 0.66 tubers per m² to 1260 tubers per m² in the uncontrolled treatment over two seasons. Cultivation during the growing season reduced C. rotundus tubers by 93% compared with the uncontrolled plots. Cover crop rotation did not reduce the number of C. rotundus tubers significantly, despite the dense sudangrass canopy shading the soil during most of the summer. Cyperus rotundus was effectively controlled by the solarization treatment. All methods controlled C. esculentus, especially when there were no crops growing in the summer. When broccoli was grown after two years of various management strategies, the cultivation treatment showed a 44% yield reduction compared with the weed‐free control, while the solarization treatment increased broccoli yield by 64% compared with the non‐solarization treatment. Rotations that included sudangrass had low broccoli yield when either C. rotundus or C. esculentus were present.     

Weed flora and seed yield in quinoa crop (Chenopodium quinoa Willd.) as affected by tillage systems and fertilization practices

The effects of tillage system and fertilization regimes on weed flora in quinoa (Chenopodium quinoa Willd.) were evaluated by means of two field experiments in 2011 and 2012. The experiments were laid out in a split-plot design with two main plots (conventional and minimum tillage) and four sub-plots (fertilization regimes). The results indicated that weed biomass and density in quinoa were influenced by the different fertilization and tillage treatments. Moreover, seed yield in conventional was 5%–13% higher than that of minimum tillage, probably due to the lower weed density and biomass. Concerning fertilization treatments, total weed density and biomass increased under manure application and inorganic fertilization. Tillage effects on weeds were species specific. The density of perennial weeds such as purple nutsedge (Cyperus rotundus L.) and the density of small-seeded weeds such as redroot pigweed (Amaranthus retroflexus L.) and common purslane (Portulaca oleracea L.) were significantly lower under the conventional tillage than under the minimum tillage system.     

Interaction between purple nutsedge,maize and soybean

The study was designed to determine the mode of interaction between maize ( Zea mays L.) and soybean ( Glycine max Merr.) in association with purple nutsedge. This was investigated under glasshouse conditions using the replacement (substitutive) series design. Maize and soybean competed with purple nutsedge for growth resources, and purple nutsedge significantly retarded the growth and development of maize and soybean. Maize was more susceptible to purple nutsedge interference compared with soybean.     

Effects of humidity and moisture stress on glyphosate control of Cyperus rotundus L.*

Glyphosate at 2 kg/ha was more effective in reducing regrowth of purple nutsedge (Cyperus rotundus L.) scapes at 90% than at 50% relative humidity (r.h.), and more effective at ?2 bars than at ?11 bars of plant water potential. Regrowth of treated plants subjected to water potentials of ?1 to ?8 bars was reduced 54–60% while at ?11 bars growth inhibition was only 34%. A time interval of as little as 8 h between application and excision was sufficient to give 47% reduction in regrowth at 90% r.h. None of the treated plants, except those clipped immediately after application, produced new shoots from the basal bulb, while all the untreated control plants produced one or more new shoots. Experiments using ¹⁴C-glyphosate substantiated these results. Three times more ¹⁴C-label was translocated into the underground parts of nutsedge at 90% than at 50% r.h. Twice as much translocated at ?2 bars than at ?11 bars of water potential.     

Effects of isothiocyanates on purple (Cyperus rotundus L.) and yellow nutsedge (Cyperus esculentus L.)

Purple and yellow nutsedge are two of the most troublesome weeds in the world. In the south-eastern USA, both weeds are common in vegetable crops and are the most difficult weeds to control in this region. A greenhouse experiment was conducted to evaluate the herbicidal activity of five liquid isothiocyanates (ITCs) (benzoyl, o -tolyl, m -tolyl, tert -octyl, and 3-fluorophenyl) on purple and yellow nutsedge. All ITCs were applied to soil in jars at 0, 100, 1000, 5000, and 10 000 nmol g⁻¹ of soil and sealed for 72 h to prevent gaseous losses, followed by nutsedge growth evaluations after an additional 18 days. All ITCs reduced purple and yellow nutsedge shoot density and shoot biomass over the concentrations evaluated, with differences in the effectiveness on each species apparent among the compounds. Based on the lethal concentration values for shoot density, all ITCs were more effective in suppressing purple nutsedge than yellow nutsedge. Benzoyl and 3-fluorophenyl were generally the most effective of the five ITCs evaluated.     

Effect of glyphosate on the sprouting of Cyperus rotundus L. tubers

Post-emergence applications of glyphosate [N-(phosphonomethyl)glycine] have been shown not to eradicate purple nutsedge (Cyperus rotundus L.) in the field. It was not known if this was due to failure to control emerged plants or if dormant tubers produced new plants after application. Studies with individual plants were conducted in screenhouse facilities to determine the effects of glyphosate rate, time for translocation, area of foliage treated, and shade on the sprouting ability of tubers attached to treated plants. Rates of 1.5–2.0 kg/ha glyphosate inhibited tuber sprouting; 72 h were required for complete translocation at 1.0 kg/ha whereas 36 h were sufficient at 2.0 kg/ha. Treating less than all of the foliage reduced foliar control and increased tuber sprouting. Shading treated plants reduced control of the foliage but did not affect glyphosate translocation to the tubers. These studies showed that glyphosate kills C. rotundus foliage and the tubers attached to treated plants. Therefore, regrowth after glyphosate application under field conditions is due to dormant tubers which sprout after treatment.     

Chemical control of perennial nutsedge (Cyperus rotundus L.) in tropical upland rice

Five herbicides were tested in the dry and in the wet season for their effectiveness in conlrolling perennial nutsedge (Cyperus rotundus L.) in direct-seeded upland rice in the tropics. K-223 [N-(α,α-dimethylbenzyl)-N'-P-tolyl urea] gave the best results. When broadcast sprayed at 8.0 kg a.i./ha in the dry season and 10 kg a.i./ha in the wet season and immediately mixed into the soit just before drilling, K-223 gave excellent perennial nutsedge control with no visible crop damage and increased the grain yield. Bentazone at 2.0 kg a.i./ha applied 7 days after crop emergence was highly selective and gave fair control of nutsedge without being toxic to the crop. MBR 8251 [1.1,1-trifluoro-4′-(phenylsulfonyl) methane-sulfono-o-toluidide] at 2.0 kg a.i./ha, mecoprop (MCPP) at 1.5 kg a.c./ha and fenoprop (silvex) at 1.0 kg a.e./ha applied 7, 14 and 7 days, respectively after crop emergence provided a fair degree of nutsedge control. Fenoprop and MBR 8251 caused slight and mecoprop moderate initial toxicity, but the injury sustained did not significantly affect crop yield.     

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.     

The degradation of the herbicide benzoylprop ethyl on the foliage of cereal seedlings

The breakdown of the herbicide benzoylprop ethyl [SUFFIX, ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate] has been examined in wheat, oat, and barley seedlings after application of ¹⁴C-labeled herbicide to the foliage.Within 15 days of the application the route and rate of the breakdown were similar in the plants of all three species. Some of the herbicide was present in the plants in a complexed form which could be extracted from the plant with organic solvents and converted back into the herbicide on treatment with hot acid. Evidence was obtained for hydrolysis of the herbicide in the plant to give its des-ethyl analog which conjugated with plant sugars. There was some evidence for a small degree of degradation of benzoylprop ethyl by debenzoylation to give products which also conjugated or complexed.There was no evidence for the formation of 3,4-dichloroaniline in the plants.