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.     

Some physicochemical factors influencing foliar uptake enhancement of glyphosatemono(isopropylammonium) by polyoxyethylene surfactants

Structure-concentration–foliar uptake enhancement relationships between commercial polyoxyethylene primary aliphatic alcohol (A), nonylphenol (NP), primary aliphatic amine (AM) surfactants and the herbicide glyphosatemono(isopropylammonium) were studied in experiments with wheat (Triticum aestivum L.) and field bean (Vicia faba L.) plants growing under controlled-environment conditions. Candidate surfactants had mean molar ethylene oxide (EO) contents ranging from 5 to 20 and were added at concentrations varying from 0·2 to 10 g litre^?-1 to [¹⁴C]glyphosate formulations in acetone–water. Rates and total amounts of herbicide uptake from c. 0·2–μl droplet applications of formulations to leaves were influenced by surfactant EO content, surfactant hydrophobe composition, surfactant concentration, glyphosate concentration and plant species, in a complex manner. Surfactant effects were most pronounced at 0·5 g acid equivalent (a.e.) glyphosate litre^?-1 where, for both target species, surfactants of high EO content (15–20) were most effective at enhancing herbicide uptake: surfactants of lower EO content (5–10) frequently reduced, or failed to improve, glyphosate absorption. Whereas, at optimal EO content, AM surfactants caused greatest uptake enhancement on wheat, A surfactants gave the best overall performance on field bean; NP surfactants were generally the least efficient class of adjuvants on both species. Threshold concentrations of surfactants needed to increase glyphosate uptake were much higher in field bean than wheat (c. 2 g litre^?-1 and < 1 g litre^?-1, respectively); less herbicide was taken up by both species at high AM surfactant concentrations. At 5 and 10 g a.e. glyphosate litre^?-1, there were substantial increases in herbicide absorption and surfactant addition could cause effects on uptake that were different from those observed at lower herbicide doses. In particular, the influence of EO content on glyphosate uptake was now much less marked in both species, especially with AM surfactants. The fundamental importance of glyphosate concentration for its uptake was further emphasised by experiments using formulations with constant a.i./surfactant weight ratios. Any increased foliar penetration resulting from inclusion of surfactants in 0·5 g litre^?-1 [¹⁴C]glyphosate formulations gave concomitant increases in the amounts of radiolabel that were translocated away from the site of application. At these low herbicide doses, translocation of absorbed [¹⁴C]glyphosate in wheat was c. twice that in field bean; surfactant addition to the formulation did not increase the proportion transported in wheat but substantially enhanced it in field bean.     

Differential effect of diclofop-methyl on fatty acid biosynthesis in leaves of sensitive and tolerant plant species

The herbicide diclofop-methyl caused an early and pronounced inhibition of the incorporation of [¹⁴C]acetate into leaf lipids of the sensitive plant species maize (Zea may L.), wild oat (Avena fatua L.), and barnyardgrass (Echinochloa crus-galli L.). With an EC₅₀ value of approximately 10^?7M inhibition was already apparent 0.5–4 hr after herbicide application. The fatty acid biosynthesis of tolerant bean (Phaseolus vulgaris L.), sugar beet (Beta vulgaris L.), and soybean (Glycine max L.) was not affected, with one exception [wheat (Triticum aestivum L.) belongs to the more tolerant species]; the inhibition of fatty acid biosynthesis, however, was in the same order of magnitude as in sensitive plants. More detailed studies showed that in wheat a recovery from inhibition of fatty acid biosynthesis occurred. Four days after herbicide application (0.18 kg diclofop-methyl/ha) in wheat normal fatty acid biosynthesis was restored, whereas in sensitive maize a 60% inhibition was maintained over the whole experimental period (8 days). The results support the view that tolerance of wheat to diclofop-methyl is based on its inactivation in leaves, whereas the tolerance of dicotyledonous species may probably lie at the level of the site of action of diclofop-methyl. In experiments with intact leaves, the inhibition of fatty acid biosynthesis resulted in an enhanced flow of [¹⁴C]acetate into organic acids and amino acids. This effect, however, was not always reproducible in experiments with leaf pieces or isolated root tips.     

Metabolic fate of methazole in purple and yellow nutsedge

The mechanisms for the tolerance of purple nutsedge (Cyperus rotundus L.) and susceptibility of yellow nutsedge (Cyperus esculentus L.) to methazole [2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione] were studied. Both species absorbed and translocated[¹⁴C]methazole and metabolites from nutrient solution; however, greater amounts of ¹⁴C per unit weight were detected in yellow than in purple nutsedge. Although intact plants and excised leaves of both species rapidly metabolized methazole to DCPMU [1-(3,4-dichlorophenyl)-3-methylurea], detoxification of DCPMU to DCPU [1-(3,4-dichlorophenyl) urea] occurred more slowly in yellow than in purple nutsedge. Compared to yellow nutsedge, a greater percentage of the radioactivity in purple nutsedge was recovered as polar products. Polar products were converted to the free forms of the parent herbicide and to phytotoxic DCPMU by proteolytic enzyme digestion. Based on the findings of this study, at least three mechanisms (differential absorption, metabolism, and formation of polar products) account for the differential tolerance of these two species to methazole.     

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.     

Differential phytotoxicity of glyphosate in maize seedlings following applications to roots or shoot

The transport and differential phytotoxicity of glyphosate was investigated in maize seedlings following application of the herbicide to either roots or shoots. One-leaf maize seedlings (Zea mays L.) were maintained in graduated cylinders (250 mL) containing nutrient solution. Half of the test plants were placed in cylinders (100 mL) containing different ¹⁴C-glyphosate concentrations; the remainder received foliar appliation of ¹⁴C-glyphosate. After 26 h, the roots and the treated leaves were washed with distilled water, and the plants placed again in cylinders (250 mL) containing fresh nutrient solution for 5 days. Plants were weighed, and split into root, seed, cotyledon, coleoptile, mesocotyl, first leaf and apex. The recovery of ¹⁴C-glyphosate was over 86%. For both application treatments, the shoot apex was the major sink of the mobilized glyphosate (47.9 ± 2.93% for root absorption and 45.8 ± 2.91% for foliar absorption). Expressed on a tissue fresh weight basis, approximately 0.26 μg a.e. g⁻¹ of glyphosate in the apex produced a 50% reduction of plant fresh weight (ED₅₀) when the herbicide was applied to the root. However, the ED₅₀ following foliar absorption was only 0.042 μg a.e. g⁻¹ in the apex, thus maize seedlings were much more sensitive to foliar application of the herbicide.     

Retention,absorption, translocation and distribution of sethoxydim in monocotyledonous and dicotyledonous plants*

Quackgrass [Elymus repens (L.) Gould =Agropyron repens (L.) Beauv.] and barnyardgrass [Echinochloa crus-galli (L.) Beauv.] were more than one hundred times more susceptible to sethoxydim than alfalfa (Medicago sativa L. 'Saranac') or navybean (Phaseolus vulgaris L. 'Seafarer'). Uptake of sethoxydim From soil following post-emergence applications caused negligible reduction in E. crus-galli fresh weight. More than 80% of foliar-applied ¹⁴C-sethoxydim was absorbed within 6 h in all species. Translocation occurred in all species with accumulation of ¹⁴C in rapidly growing plant tissues. Translocation to the roots was less than 8% of total in all species. Most of the extracted ¹⁴C initially partitioned into an ethyl acetate-soluble fraction. The proportion of ¹⁴C in the ethyl acetate-soluble fraction decreased with time with a concomitant increase of that in the insoluble fraction. Differences in the quantity of ¹⁴C in the ethyl acetate-soluble fraction did not account for the observed selectivity.     

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.     

Some chemical and physical properties of epronaz,a new herbicide

A brief account is given of the work leading up to the synthesis of epronaz (BTS 30 843), 1-(N-ethyl-N-propylcarbamoyl)-3-propylsulphonyl-1,2,4-triazole, a new pre- and early post-emergence herbicide for annual grasses. The synthesis is described, together with the occurrence and isolation of all three possible positional isomers in the final (carbamoylation) stage. The evidence for the structure assigned to epronaz is presented together with that for the other two isomers, and their interconversion is described. Some chemical properties of epronaz are described, with particular reference to its hydrolysis and its ability to function as a carbamoylating agent, in relation to persistence in the environment and to mode of action respectively. Some physical properties are also reported, including vapour pressure, solubility, and spectra. The mass spectral fragmentation pattern is also discussed.     

Absorption, translocation, and fate of propyzamide in witloof chicory (Cichorium intybus L.) and common amaranth (Amaranthus retroflexus L.)

Witloof chicory (Cichorium intybus L.) is tolerant to propyzamide and common amaranth (Amaranthus retroflexus L.) is sensitive. The absorption, translocation, and metabolism of propyzamide was studied in seedlings of witloof chicory and common amaranth to determine if differences in these processes cause the differential sensitivity. At 24,48, and 72 h after root treatment, there was no difference in the concentration of ¹⁴C (g^?1 plant dry wt) in com-mon amaranth and witloof chicory. Approximately 50% of the absorbed ¹⁴C was translocated out of the roots to shoots of both species at 24 and 48 h after treatment. After 72 h about 55 and 74% of the absorbed ¹⁴C was translocated to shoots of witloof chicory and common amaranth, respectively. Distribution of ¹⁴C (g^?1 plant dry wt) in plant parts of witloof chicory and common amaranth seedlings was similar. Roots of both species accumulated the highest concentration of total ¹⁴C, whereas shoots contained the lowest. Thin layer chromatography revealed that the herbicide was metabolized in neither species 48 h after treatment. No differences were found in absorption, translocation, or metabolism between witloof chicory and common amaranth with regard to propyzamide.     

Selectivity of glyphosate in creeping red fescue and reed canarygrass*

The differential tolerance of resislant creeping red fescue (Fes- tuca rubra L, var, rutra) and susceptibie reed canarygrass (Pha- laris arundinacea L.) seedlings to glyphosate [N-(phosphono- meihyDglycine) was confirmed under growth chamber condilions. The absorption, transiocation and metabolism of ¹⁴C-glyphosate was examined in both species to determine if differences in these processes could account for the observed selectivity, Creepmg red fescue actually absorbed more glyphosate than did t-eed canarygrass, and both species rapidly translocated the herbicide throughout their respective tissues. No metabolism of glyphosate was detected in either species. Differential interception and retention of the glyphosate spray can probably be eliminated as possible selectivity mechanisms. The relative tolerance of creeping red fescue to glyphosale appears to be related to its ability lo regenerate roots and shoots from the crown of the plant, but the mechanism of resistance remains obscure.     

Studies on the selectivity of alloxydim-sodium in plants

Alloxydim-sodium, methyl 3-[1-(allyloxyimino)butyl]-4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-enecarboxylate sodium salt, is a selective herbicide which controls grass weeds in a wide range of broad-leaf crops. Spray retention, tested at two growth stages, was generally greater for the broad-leaf crops (cotton, sugarbeet, flax, beans and peas) than for wild oat (Avena fatua L.), blackgrass (Alopecurus myosuroides Huds), barley and couch grass [Agropyron repens (L.) Beauv.], and did not contribute to selectivity between susceptible and tolerant species. Broad-leaf crops tolerated 2820 g alloxydim-sodium ha^?1, three times the recommended rate used to control annual grasses. Differential uptake and translocation were not factors contributing to selectivity. In wild oat, blackgrass and sugarbeet, uptake and translocation of ¹⁴C continued during a period of 14 days after treatment with [¹⁴C]alloxydim-sodium. Translocation in susceptible and tolerant species was predominately symplastic. Over 40% of the applied ¹⁴C was eliminated from treated wild oat, blackgrass and sugarbeet plants within 7 days, due to degradation and volatilisation. A greater proportion of the methanol-soluble radioactivity extracted from leaves and roots was present as water-soluble polar metabolites in sugarbeet, than in wild oats, 7 days after treatment. The proportion of unaltered alloxydim in the organo-soluble fraction of a methanol extract was greater in wild oat than in sugarbeet. Differential metabolism appears to be one of the factors contributing to alloxydim-sodium selectivity between sugarbeet and wild oat.     

Foliar absorption and translocation of nicosulfuron and rimsulfuron in five annual weed species

Ambrosia artemisüfolia L. (common ragweed) and Digitaria ischaemum Schreb. (smooth crabgrass) are not controlled by nicosulfuron and rimsulfuron at the highest recommended application rates, whereas Panicum miliaceum L. (wild proso millet), Amaranthus retroflexus L. (redroot pigweed) and Avena fatua L. (wild oat) are susceptible. The foliar absorption and translocation of ¹⁴C-nicosulfuron and ¹⁴C-rimsulf uron were studied in these weed species up to 48 h after treatment (HAT). Differences in herbicide uptake and translocation were not correlated with the species susceptibility. By 48 HAT, more than 50% of both herbicides remained on the treated leaf surface. Foliar absorption of rimsulfuron was greater than that of nicosulfuron in A. retroflexus, P. miliaceum and A. artemisüfolia. Most of the absorbed herbicide remained in the treated leaf of each weed species. Export of ¹⁴C–nicosulfuron ranged from 28 to 54% of that absorbed, in contrast to 15 to 39% for ¹⁴C–rimsulfuron. The absorption and translocation rates of both herbicides were highest within the initial 6 HAT, and decreased thereafter. Both herbicides showed approximately the same distribution pattern within each weed species.     

Physiological responses of maize and sorghum to four different safeners for metazachlor

The ability of the herbicide safeners, BAS-145138 (1-dichloroacetyl-hexahydro-3,3,8a-trimethyl-pyrrolo(1,2a)pyrimidin-6(2H)-one), dichlormid (N,N-diallyl-2,2-dichloroacetamide), flurazole (phenylmethyl ester), and MG-191 (2-dichloromelhyl-2-methyl-1,3-dioxolane) for preventing metazachlor injury to maize (Zea mays L.) and sorghum (Sorghum bicolor L.) seedlings were compared with their effects on ¹⁴C-metazachlor metabolism to a glutathione (GSH) conjugate, effects on non-protein thiol contents (mainly GSH) and effects on Glutathione S-transferase (GST) activity in these two species. Sorghum shoot growth was reduced by 41% and maize shoot growth was reduced by 54%, by metazachlor concentrations in vermiculite nutrient culture of 0·6 μM and 7·5μM, respectively. In this system, all four compounds had significant activity as safeners for metazachlor in both sorghum and maize seedlings. BAS-145138 and flurazole were the most effective safeners in maize and sorghum, respectively. In the absence of safeners, the rate of non-enzymatic conjugation of metazachlor and GSH was much greater than the enzymatic rate. However, the rate of enzymatic conjugation of metazachlor with GSH was increased by safener treatment in both maize and sorghum. Safener effectiveness was highly correlated with increases in ¹⁴C-metazachlor uptake and metabolism in both species. Safener effectiveness was more highly correlated with safener effects on GST activity in maize or sorghum when ¹⁴C-metazachlor was used as the substrate than when the non-specific CDNB (1-chloro-2,4-dinitrobenzene) was used as the substrate. Safener effectiveness was also strongly correlated with safener effects on GSH levels in sorghum, but not in maize, possibly because of the greater importance of non-enzymatic conjugation of metazachlor with GSH in sorghum as compared to maize.     

Spreading and penetration of herbicides dissolved in oil carriers*

Four non-phytotoxic paraffinic oils of increasing viscosities and boiling ranges were compared as carriers for 2,4-D, dinoseb and terbacil under glasshouse conditions. Terbacil and dinoseb activity was increased approximately ten-fold in the oil carriers (150 1/ha) v. water on ivyleaf morning glory (Ipomoea hederacea (L.) Jacq.), cucumber (Cucumis sativus L.) and sorghum (Sorghum bicolor (L.) Moench). 2,4-D activity on bean (Phaseolus vulgaris L.) and sorghum was not increased by the oil carriers. The four oils showed similar effectiveness as herbicide carriers except that a trend existed towards increased herbicide activity in the medium to high viscosity, low volatile oils. ¹⁴C-chlorpropham was applied in a non-phytotoxic oil carrier to the leaves of morning glory, cucumber and sorghum. It moved externally on the upper but not on the lower leaf surface to the shoot apex of all plants, but internal herbicide transport was not evident. Similarly, greater surface movement and penetration of ¹⁴C-2,4-D occurred in sorghum, when applied in the same oil carrier v. water with surfactant, but herbicide translocation was not affected. The penetration and translocation pattern of ¹⁴C-2,4-D applied in four non-phytotoxic oil carriers of increasing viscosities were studied in bean (Phaseolus vulgaris L.). All oil carriers, as compared to 2,4-D in water-surfactant greatly enhanced herbicide penetration through both upper and lower primary leaf surfaces and subsequent translocation. The extent of oil carrier movement on the leaf surface did not determine the distance of subsequent herbicide translocation which was the same for all four oil carriers, but did influence amount of the herbicide translocated. Approximately the same quantity of ¹⁴C was absorbed through both upper and lower leaf surfaces for both ¹⁴C-chlorpropham and ¹⁴C-2,4-D in oil carriers, indicating that stomatal penetration is not a factor in determining rate of oil entry into leaves. This work indicates the importance of measuring oil carrier mobility on the leaf surface, when studying the effects of such carriers on herbicide penetration and translocation. Etalement et penetration d'herbicides dissous dans des supports huileux. Quatre huiles paraffiniques non toxiques ayant des viscosityés et des zones d'ébullition croissantes ont été comparées, en serre, comme supports pour le 2,4-D, le dinosébe et le terbacile. L'activité du terbacile et du dinosébe a été approxi-mativement multipliée par dix dans les supports huileux (150 1/ha) par rapport au support hydrique, sur le liseron (Ipomoea hederacea (L.) Jacq.), le concombre (Cucumis sativus L.) et le sorgho (Sorghum bicolor (L.) Moench). L'activité du 2,4-D sur le haricot (Phaseolus vulgaris L.) et le sorgho n'a pas été accrue par les supports huileux. Les quatre huiles ont manifeste une efficacité analogue en tant que supports pour les herbicides; toutefois, l'activitd herbicide tend à s'accroître entre les viscosityés moyennes et fortes, pour des huiles à basse volatilityé. Le chlorprophame-¹⁴C a été appliqué dans un support huileux non phytotoxique sur les feuilles de liseron, de concombre et de sorgho. II migre extérieurement sur la face foliaire supérieure mais pas sur la face inférieure vers l'apex des tiges de toutes ces plantes; cependant la migration en surface et une pénétration plus importantes du 2,4-D-¹⁴C se sont manifestoes dans le sorgho lorsque I'herbicide a été appliqué dans le meme support huileux, en comparaison avec le support eau plus agent tensio-actif, mais la migration interne de I'herbicide n'a pas été affectée. Le mode de pénétration et de migration du 2,4-D-¹⁴C appliqué dans quatre supports huileux non phytotoxiques, de viscosités croissantes, a étéétudié chez le haricot (Phaselous vulgaris L.). Tous les supports huileux, par comparaison avec l'eau plus un agent tensio-actif, ont hjrtement augmenté la pénétration du 2,4-D à travers les faces supérieure et inférieure de la feuille, ainsi que sa migration ultérieure. L'étendue du déplacement du support huileux sur la surface foliaire n'a pas déterminé la distance de la migration ultérieure de I'herbicide, laquelle fut identique pour les quatre huiles, mais elle a influencé la quantité d'herbicide transportée. Une quantité approximativement identique de ¹⁴C a été absorbie á travers les faces supérieure et inférieure de la feuille pour le chlorprophame ¹⁴C et le 2,4-D-¹⁴C dans les supports huileux, ce qui montre que la pénétration par les stomates n'est pas un facteur déterminant de la dose de pénétration de I'huile dans les feuilles. Ce travail met en évidence l'importance de la mesure de la mobilité du support huileux sur la surface foliaire lorsqu'on étudie les elTets de tels supports sur la pénétration et la migration de I'herbicide. Verteilung und Penetration von in öl gekosten Herbiziden Vier nicht phytotoxische Paraffinöle unterschiedlicher Viskos-ität und von verschiedenem Siedebereich wurden als Träger für 2,4-D, Dinoseb und Terbacil unter Gewächshausbeding-ungen miteinander verglichen. Die Wirkung von Terbacil und Dinoseb mit den Ölen als Träger (150 1/ha) gegenüber Ipomoea hederacea (L.) Jacq., Cucumis sativus L. und Sorghum bicolor (L.) Moench. war, verglichen mit Wasser als Trager, um etwa zehnmal besser. Die Wirkung von 2,4-D auf Phaseolus vulgaris L. und Sorghum wurde durch die Ole nicht verbessert. Die vier Öle wirkten als TrSgersubstanz fur die Herbizide etwa gleich gut. Es bestand aber eine Beziehung derart, dass Öle mit mittlerer bis hoher Viskositat und geringer Fluchtigkeit eine verbesserte Herbizidaktivitat bewirkten. ¹⁴C-Chlorpropham wurde in einem nicht phytotoxischen Öl auf die Blätter von Ipomoea, Cucumis und Sorghum appliziert. Es breitete sich bei alien Pflanzen auf der Blatto-berseite, nicht jedoch auf der Biattunterseite, bis zum Sprossapex aus. Ein Transport des Herbizids in der Pflanze wurde nicht beobachtet. Ahnlich war es mit ¹⁴C-2,4-D bei Sorghum: verglichen mit Wasser plus Surfactant bewirkte das gleiche Öl eine grössere Flächenausbreitung und eine verbesserte Penetration; die Translokation des Herbizids wurde jedoch nicht beeinflusst. Die Penetration und Translokation von ¹⁴C-2,4-D, appliziert in vier nicht phytotoxischen Oien mit unterschiedlicher Viskosität, wurde an Phaseolus untersucht. Im Yerg-leich zu 2,4-D in Wasser plus Surfactant bewirkten alle Ole eine wesentlich verbesserte Penetration und Translokation des Herbizids. Die mit Öl bedeckte Blattoberflache hatte keinen Einfluss auf die Translokationsstrecke des Herbizids. Diese Distanz der Herbizidtranslokation war bei alien Ölen gleich gross. Die Menge an transloziertem 2,4-D war jedoch unterschiedlich gross. Von dem in den verschiedenen Ölen gelösten ¹⁴C-Chlor-propham und ¹⁴C-2,4-D wurde ungefahr die gleiche Menge an ¹⁴C sowohl durch die Blattober- wie auch durch die Biattunterseite absorbiert, was darauf hinweist, dass die Penetration des Öls in das Blatt nicht durch die Aufnahmer-ate über die Stomata bestimmt wird. Diese Arbeit weist auf die Bedeutung von Untersuchungen hin, die sich mit der Messung der Beweglichkeit von Öl-Trägerstoffen auf der Blattfläche beschäftigen, wenn die Wirkung solcher Träger auf die Penetration und Translokation von Herbiziden untersucht werden soll.     

Effect of non-ionic nonylphenol surfactants on surface physicochemical properties, uptake and distribution of asulam and diflufenican

The effect of non-ionic nonylphenol (NP) surfactants containing 4–14 ethylene oxide (EO) molecules on the distribution of asulam and diflufenican was investigated in Pteridium aquilinum L. Kuhn and Avena fatua L. The distribution of the herbicides was dependent on the EO content and concentration of surfactant and differed between plant species and herbicide. The surface properties of contact angle, droplet diameter and surface tension were examined. For solutions of asulam, the greatest reductions in contact angle, surface tension and greatest droplet diameter were obtained with surfactants of EO 6.5–10 (at 0.001–0.1%). For solutions of diflufenican, these responses were greatest when applied with surfactant of EO 4. Surfactants of EO 6.5–10 increased the uptake and translocation of [¹⁴C]asulam in P. aquilinum, particularly at surfactant concentrations of 0.01 % and 0.1 %. All surfactants increased uptake of [¹⁴C]asulam in A. fatua with no significant effects of surfactant EO number or concentration. For both species, there was a positive correlation between the optimum surface characteristics of the herbicide droplets and the uptake of asulam. With diflufenican, greatest uptake and translocation by mature frond tissue of P. aquilinum occurred at the highest concentration of surfactant EO 4; in A. fatua, however, uptake and translocation were not significantly affected by any of the surfactants.     

Effect of CGA 123407 as a safener for pretilachlor in rice (Oryza sativa L.). Recordings of elongation rates of single rice leaves

The elongation rates of single attached leaves of rice (Oryza saliva L.) were recorded. The effect of pretilachlor on the elongation rates and the safening effect of CGA 123407 [4, 6-dichloro-2-phenyl-pyrimidine] were evaluated. Both chemicals were applied to the roots in a nutrient solution. Pretilachlor reduced leaf elongation in concentrations as low as 300 μg^?1 (9–6 × 10^?7 M) but. for combination trials with the safener, 3 mg 1^?1 (9–6 × 10^?6 M) was used. in combination with pretilachlor the safener prevented damage in very low concentrations. The ratio of pretilachlor to safener, 30:1, was sufficient when both chemicals were given to roots in nutrient solution, although for field work the ratio of 3:1 is recommended. The safener alone did not influence the elongation rate of rice leaves in the concentrations used. When pretilachlor was given to the roots and CGA 123407 to the shoot, some delay in the herbicidal action was recorded but even with high concentrations of the safener no continuous safening effect was achieved. CGA 123407 was also effective when given previous to the herbicide. This proved true even with a 2-day interval between safener uptake and application of the herbicide. When pretilachlor was given first, the safener effected recovery to various degrees when given 1–4 days after the herbicide application. When pretilachlor was given for a limited period of time only (1–3 days) and was subsequently removed from the nutrient solution, recovery of the plant occurred. It is speculated that the safener either helps this recovery or else competitively prevents the herbicide from occupying the sites of action or from keeping them occupied for a long period of time.     

Glyphosate resistance in common ragweed ( A mbrosia artemisiifolia L.) from Mississippi,USA

Glyphosate is one of the most commonly used broad‐spectrum herbicides over the last 40 years. Due to the widespread adoption of glyphosate‐resistant (GR) crop technology, especially corn, cotton and soybean, several weed species have evolved resistance to this herbicide. Research was conducted to confirm and characterize the magnitude and mechanism of glyphosate resistance in two GR common ragweed ( A mbrosia artemisiifolia L.) biotypes from Mississippi, USA. A glyphosate‐susceptible (GS) biotype was included for comparison. The effective glyphosate dose to reduce the growth of the treated plants by 50% for the GR1, GR2 and GS biotypes was 0.58, 0.46 and 0.11 kg ae ha^?1, respectively, indicating that the level of resistance was five and fourfold that of the GS biotype for GR1 and GR2, respectively. Studies using ¹⁴ C‐glyphosate have not indicated any difference in its absorption between the biotypes, but the GR1 and GR2 biotypes translocated more ¹⁴ C‐glyphosate, compared to the GS biotype. This difference in translocation within resistant biotypes is unique. There was no amino acid substitution at codon 106 that was detected by the 5‐enolpyruvylshikimate‐3‐phosphate synthase gene sequence analysis of the resistant and susceptible biotypes. Therefore, the mechanism of resistance to glyphosate in common ragweed biotypes from Mississippi is not related to a target site mutation or reduced absorption and/or translocation of glyphosate.     

Studies on the mode of action of asulam,aminotriazole and glyphosate in Equisetum arvense L. (field horsetail). II: The metabolism of [14C]asulam, [14C]aminotriazole and [14C]glyphosate

The metabolism of [¹⁴C]asulam (methyl 4-aminophenylsulphonylcarbamate), [¹⁴C] aminotriazole (1H-1,2,4-triazol-3-ylamine) and [¹⁴C]glyphosate (N-(phosphonomethyl)glycine) were assessed in Equisetum arvense L. (field horsetail). Following application of the test herbicides (4mg?0.3 °Ci herbicide/shoot) to the shoots of 2-year-old pot-grown plants, the total recovery of ¹⁴C-label after 1 week and 8 weeks was high for all three herbicides (>80-0% of applied radioactivity). Asulam was persistent (>69-7% of recovered radioactivity) in both shoots and rhizomes. Sulphanilamide, a hydrolysis product of asulam, accounted for the remainder of the recovered radioactivity. Aminotriazole showed evidence of conjugation in shoots and rhizomes. The principal ¹⁴C-labelled component in shoots was composed of high proportions of aminotriazole (>76-3%) together with the metabolites: X (ninhydrin positive), β-(3-amino-1,2,4-triazolyl-1-)α-alanine, Y (diazotization positive) and various unidentified compounds. Rhizomes generally contained lower proportions of intact aminotriazole (>59.4%) together with the metabolites X,Y and unidentified compounds. The proportion of aminotriazole did not decrease with time in shoots or rhizomes; however, the ratio of metabolite X: Y moved in favour of Y as the interval after treatment increased. Glyphosate was extensively metabolised in shoots and rhizomes to yield aminomethylphosphonic acid (AMPA) and various unidentified compounds. Differential metabolism appears to be one of the factors which may govern the persistence and toxicity of the test herbicides in E. arvense.     

Biological activity of the new herbicide LGC-40863 {benzophenone O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime}

Herbicidal characteristics of the experimental compound LGC-40863 (ISO proposed common name: pyribenzoxim) were investigated in greenhouse and field. In the greenhouse, LGC-40863 had strong post-emergent activity on various grass and broadleaf weeds including Echinochloa crus-galli L. Beauv., Alopecurus myosuroides Huds. and Polygonum hydropiper L., while it was safe in rice (Oryza sativa L.), wheat (Triticum aestivum L.) and zoysiagrass (Zoysia japonica Steud; (a turf species). Among important rice weeds, E. crus-galli was controlled over a wide window from the one-leaf to the six-leaf stages. In the field, LGC-40863 provided excellent control of E. crus-galli (>95%) at 30 to 40 g ha^-1 when applied alone, or at 15 to 30 g ha^-1 when applied in combination with pendimethalin, while it did not cause injury to rice at up to 60 g ha^-1. These results suggest that LGC-40863 has potential as a new selective post-emergent herbicide in rice. © 1997 SCI