A root bioassay procedure for the determination of chlorsulfuron, diclofop acid and sethoxydim residues in soils

Measurement of the root lengths of pre-ger-minated oat seedlings (Avena sativa L. var. Sioux) grown in the dark in treated soils was used to assay residues of diclofop acid (2-[4-(2,4-dichloro-phenoxy)phenoxy]propionate) and sethoxydim (2-[1-(ethoxyimino)-butyl]-5-[2-(ethylthio)-propy]-3-hydroxy-2-cyclohexene-1-one). Similar measurements involving maize seedlings (Zea Mays L. var. Sunny Vee) were also used to determine residues of the herbicide chlorsulfuron (2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbony]benzenesulfonamide) in soils. The procedure appeared to be reproducible with residues of chlorsulfuron, diclofop acid and sethoxydim being detectable at amounts of 0.001, 0.2 and 0.05 μg g^?1 respectively.     

The response of resistant and susceptible plants to diclofop-methyl

Wild oat (Avena fatua L.) plants sprayed at the 2-or 3-leaf stages of growth with diclotop-methyl developed chlorosis over the entire leaf blade of all leaves. The leaves became necfrotic ⁷days after spraying Shool growth was inhibited. In wheat (Triticum aesicum L cv.Waldron) discrete chlorotic areas developed only where the herbicide convicted the 2nd or 3rd leaf with no visible injury so new growth uf'ter treutment. Growth inhibition of susceptible oat (Avena sativa L. cv. Garry) was sensitive to placement of diclutop-methyl near the upica and meristematic sites of the plant. Chlorosis and necrosis were independent of herbicide placement. Selective herbicide placement induced chlorosis only or both chlorosis and growth inhibition Root growth in wild oat and barley (Hordeum rulgare L. cv. Dickson) was strongly inhibited by 1–0 μM diclofop-methyl. Wild oat shoots were killed when seedlings were root-treated with 10 μM diclofop-melhyl. The 100 μM rool treatment killed barley shoots but only stunted the growth of wheat shoots by approximately 50%. In root-ireated wheat plants the shoots were turgid and developed a light purple colour, whereas in foliar-treated plants the shoots developed discrete chlorotic areas.     

Enantioselective transformation of the herbicides diclofop-methyl and fenoxaprop-ethyl in soil

The separate enantiomers of diclofop-methyl and fenoxaprop-ethyl were incubated with two soils under aerobic conditions. Rapid hydrolysis to the corresponding acids diclofop and fenoxaprop was observed. At various time intervals after soil treatment the parent compound and its free acid were extracted and the extracts were investigated by high-performance liquid chromatography. The determination of the K:S-ratio using a chiral stationary phase revealed that no racemisation of the esters took place. However, inversion of the hydrolysis products was observed. In both soils the acids with the S-configuration showed a significantly higher inversion tendency than the acids with the R-configuration. In one soil the S-acids of both herbicides were inverted (50% inversion in 4–7 days) to yield, ultimately, a residue containing 70% R- and 30% S-enantiomer.     

禾草灵防除春麦田禾本科杂草药效试验初报

1　材料与方法1 1　供试药剂供试药剂有 2 8%、36 %禾草灵乳油 (浙江一帆农药化工有限公司产 )、6 9%骠马水乳剂 (德国艾格福公司产 )。1 2　试验设计试验在西宁彭家寨乡彭家寨村小麦田进行 ,防除以野燕麦为主的禾本科杂草。设2 8%禾草灵ＥＣ每公顷商品量 (下同 )2 40 0ｍｌ、30 0 0ｍｌ、36 0 0ｍｌ,36 %乐草灵ＥＣ每公顷 1 80 0ｍｌ、2 340ｍｌ、2 70 0ｍｌ,6 9%骠马水收稿日期 :2 0 0 1- 0 6 - 0 4乳剂每公顷 750ｍｌ,以喷清水为对照 ,共 8个处理。小区面积 1 8ｍ2 ,重复 4次 ,随机排列。 5月 1 2日施药 ,施药前 4ｄ田间灌苗头水。喷…     

Catalytic hydrolysis of diclofop-methyl on Ca-, Na- and K-montmorillonites

The decomposition of the herbicide diclofop-methyl (methyl (RS)-2-(4-(2,4-dichlorophenoxy)phenoxy)propionate), on homoionic Ca-, Na- and K-montmorillonite in hydroalcoholic suspension was investigated. The results show that the solvolysis of the pesticide affords two products: diclofop (RS)-2-(4-(2,4-dichlorophenoxy)phenoxy)propionic acid) and diclofop-ethyl (ethyl (RS)-2-(4-(22,4-dichlorophenoxy)phenoxy)propionate). The former is always the main product of hydrolysis on the Ca-, Na- and K-clays, whereas the latter, arising from a transesterification reaction, is favoured only by the presence of Ca-and Na-clays. The solvolysis reaction follows the adsorption of the herbicide on the clay, as evidenced by the shift of the IR stretching value of the ester group of the molecule, depending on the polarising power of the saturating ions.     

Root exudation of diclofop-methyl and triasulfuron from foliar-treated durum wheat and ryegrass

In this study, we evaluated the release of diclofop-methyl and triasulfuron from the roots of foliar-treated ryegrass and wheat. The study with ¹⁴C-diclofop-methyl indicated a basipetal translocation of foliar-applied herbicide in wheat and ryegrass. No root exudation from ¹⁴C-diclofop-methyl-treated wheat plants was observed, while 20 days after treatment (DAT) 0.2–0.9% of radioactivity absorbed by ryegrass was found exuded in the growing medium. Root exudation was stimulated three to six times by the presence of untreated wheat or ryegrass sharing the growing medium with diclofop-methyl-treated ryegrass. No subsequent uptake of exuded radiolabel by untreated plants (ryegrass or wheat) in the same pot with ¹⁴C-diclofop-methyl-treated ryegrass was observed. The study with ¹⁴C-triasulfuron indicated a basipetal translocation of foliar-applied herbicide in wheat and ryegrass and also into the growing medium. By 20 DAT, 0.5–4.2% of radioactivity absorbed by wheat or ryegrass was found exuded in the growing medium. The presence of untreated plants (wheat or ryegrass) in the same pot as triasulfuron-treated ryegrass or wheat induced exudation seven to 32 times more. The study also revealed a subsequent uptake of exuded compounds by untreated wheat or ryegrass sharing the medium of ¹⁴C-triasulfuron-treated plants. This study has demonstrated for the first time that the root exudation of exogenous compounds can be related to plant arrangement in pots. The implication is that herbicide root exudation and transfer, a form of allelopathy, could be significant in the field. A precise estimation of environmental fate, unexpected ecological side effects and residual activity of herbicides may require quantification of such exudation.     

Response of wheat and oat seedlings to root-applied diclofop-methyl and 2,4-dichlorophenoxyacetic acid

Roots of wheat and oat seedlings were treated with diclofop-methyl (methyl 2-[4-(2′,4′-dichlorophenoxy)phenoxy]propanoate) in a specially designed Plexiglas treatment apparatus. Diclofopmethyl severely inhibited the root growth of susceptible oat seedlings but roots of resistant wheat seedlings were unaffected. Diclofop-methyl at 0.3 μM reduced the growth of oat roots to 50% of the control. Direct contact between diclofop-methyl and the inhibited root zone was necessary for growth inhibition since other parts of the seedling (roots and shoots) isolated from contact with diclofop-methyl solution by a physical barrier were unaffected. Diclofop (2-[4-(2′,4′-dichlorophenoxy)phenoxy]propionic acid), the free acid metabolite of diclofop-methyl, was somewhat more phytotoxic than the parent compound. The herbicide, 2,4-dichlorophenoxyacetic acid (2,4-D), which engenders auxin responses, slightly enhanced the inhibition of oat root growth by diclofop-methyl. The primary wheat metabolite, ring-hydroxylated diclofop, was nonphytotoxic to oat root growth, whereas the acetylated derivative of the primary water-soluble oat metabolite (neutral glucose ester of diclofop) inhibited oat root growth to the same extent as diclofop-methyl. These results support the hypothesis that the basis for selectivity between resistant wheat and susceptible oat is the metabolism of diclofop-methyl by aryl hydroxylation and conjugation but not glucose ester conjugation. Translocation is also not an important factor in the phytotoxic activity of diclofop-methyl.     

Interaction between diclofop-methyl and 2,4-D in wild oat (Avena fatua L.) and cultivated oat (Avena sativa L.), and fate of diclofop-methyl in cultivated oat

Influence of 2,4-D on toxicity of diclofop-methyl to Avena sativa (cv. Selma) and Arena fatua at 2·5 leaf stage has been evaluated under controlled conditions. Effects of 2,4-D on the fate of diclofop-methyl in cultivated oat have also been studied. Mixture with 2,4-D reduced the toxicity of diclofop-methyl to both species. When applied immediately after diclofop-methyl treatment, 2,4-D still reduced herbicide toxicity to wild oat. This reduction was smaller in cultivated oat. and was only observed at higher phytotoxicity. No interaction was observed when a 10-day period separated the two applications. In mixture, 2,4-D enhanced diclofop-methyl penetration and diclofop acid conjugation in cultivated oat, and it slightly increased conjugation when applied separately. None of these effects clearly explain the reduction of diclofop-methyl toxicity by 2, 4-D in cultivated oat. Other processes are possibly involved and could be connected with the site of action of diclofop-methyl.     

Taxonomic evaluation of Italian populations of Lolium spp. resistant and susceptible to diclofop-methyl

A comprehensive research project was set up to characterize by different approaches some Italian populations of Lolium spp. susceptible and resistant to diclofop-methyl. The present study was aimed at the taxonomic identification of these Lolium populations on the basis of the electrophoretic analysis of seed reserve proteins. Electrophoresis confirmed the great range of variation detected by preliminary morphological analysis. Approximately half the individuals in each population could be classified as belonging to Lolium multiflorum or Lolium rigidum , the most common Lolium species present in the area. However, electrophoretic patterns revealed a significant number (40–60%) of hybrid individuals in all populations. The origin of these off-types was postulated as resulting from both intrageneric hybridization among different Lolium species and intergeneric hybridization between Lolium and Festuca genera. No significant differences were detected in the taxonomy of herbicide-susceptible and -resistant populations.     

Distribution of diclofop-methyl and metabolites in oat (Avena sativa L.) protoplasts

The metabolism of the herbicide diclofop-methyl and the distribution of it and its metabolites have been investigated in a system utilizing isolated oat protoplasts (Avena sativa L. ‘Cascade’). Accumulations of ¹⁴C-diclofop-methyl were found in membrane fractions of the protoplasts. Diclofop-methyl partitioned into the lipid phase of the protoplast plasma membrane. Comparatively small amounts of diclofop were found associated with the protoplasts. Diclofop-methyl was converted to diclofop in the treatment solution by hydrolytic enzymes associated with the external surface of the protoplast. Approximately 78% of the radiolabel recovered from the treatment solution was diclofop. The two major accumulations of radiolabel were found in the water insoluble portion (membrane fraction) of the protoplast as diclofop-methyl and in the treatment solution as diclofop. Repartition du diclofop-methyl et de ses métabolites dans les protoplastes d'avoine (Avena sativa L.) Le métabolisme de l'herbicide diclofop-methyl (DM) et la répartition du DM et de ses métabolites ont étéétudiés dans un système faisant appel à des protoplastes d'avoine isolés (Avena sativa L.) ‘Cascade’. Des accumulations de ¹⁴C-diclofop-methyl ont été trouvées dans la fraction membranaire des protoplastes. Le diclofop-methyl est passé dans la phase pidique de la membrane plasmique du protoplaste. En comparaison, de petites quantités de diclofop ont été trouvées en association avec les protoplastes. Le diclofop-methyl a été converti en diclofop par des hydrolases associées à la surface externe des protoplastes. Approximativement 78% des traces radioactives retrouvées dans la solution de traitement étaient du diclofop. Les deux principales accumulations de radioactivitéétaient trouvées dans la fraction insoluble dans l'eau des protoplastes (fraction membranaire) sous forme de diclofop-méthyl et, dans la solution de traitement, sous forme de diclofop. Verteilung von Diclofop-methyl und Metaboliten in Hafer- (Avena sativa L.)-Protoplasten Der Abbau von ¹⁴C-markiertem Diclofop-methyl und die Verteilung des Wirkstoffs sowie eines Metaboliten wurden in isolierten Protoplasten von Hafer (Avena sativa L. ‘Cascade’) untersucht. Der Wirkstoff war in den Protoplastenmembranen angereichert, wobei eine Anlagerung an die Lipidphase der Plasmamembran festgestellt wurde. Von Diclofop waren vergleichsweise geringe Mengen an die Protoplasten gebunden. Diclofop-methyl wurde in der Versuchslösung durch hydrolytische Enzyme, die an der Protoplastenaussenfläche lagen, zu Diclofop umgewandelt. Radioaktiv markierte Stoffe wurden hauptsächlich als Diclofop-methyl am Protoplasten-membransystem und als Diclofop (mit 78% der eingebrachten ¹⁴C-Aktivität) in der Lösung gefunden.     

Growth and yield responses of Italian ryegrass (Lolium multiflorum) to diclofop-methyl and ozone

We evaluated the combined effects of diclofop‐methyl herbicide application and the air pollutant ozone (O₃) on diclofop‐methyl‐resistant and ‐susceptible biotypes of Italian ryegrass (Lolium multiflorum). We conducted two experiments, one with a long vegetative growth period and the other with a short vegetative growth in late spring with seed production in summer. As expected, because of its phytotoxicity, the herbicide alone reduced total vegetative biomass, leaf area, tiller number and seed production at most sampling periods in susceptible plants for both experiments. However, it had variable effects on resistant plants, including a positive effect on seed production. Ozone alone delayed vegetative biomass accumulation and reduced leaf area and seed biomass in both experiments. However, the effects of O₃ on some parameters were altered by herbicide rate and/or biotype. Especially notable was a greater reduction in seed biomass because of O₃ in resistant than in susceptible plants with no herbicide. If these apparent differential responses to herbicide and O₃ stress of susceptible and resistant plants are confirmed and persist over time, evolutionary tradeoffs may occur. For example, the frequency of resistant plants in a population may be altered in response to interactions between herbicides and other anthropogenic stresses.     

In vitro sensitivity of wheat and oat mitochondria to the selective herbicide,diclofop-methyl

Compared to diclofop-methyl (methyl 2-[4-(2′,4′-dichlorophenoxy)phenoxy]propanoate), diclofop (the demethylated derivative) was a more potent inhibitor of polarographically monitored state 3 respiration of mitochondrial preparations isolated from shoots of dark-grown wheat (Triticum aestivum L. cv. Neepawa) and oat (Avena sativa L. cv. Terra) seedlings. Wheat and oat mitochondria demonstrated essentially similar concentration-response patterns for the uncoupler-like stimulation of state 4 respiration and the inhibition of state 3 respiration by diclofop, thereby intimating that differential mitochondrial sensitivity was not a selectivity factor between these species. Diclofop suppression of unconstrained oxygen utilization elicited by the respiratory uncoupler FCCP indicated that inhibition of state 3 respiration involved interference with some site(s) on the mitochondrial electron transport chain and not with energy transfer directly. Cytochrome c oxidase activity was not affected by diclofop, but succinate- and malate-PMS oxidoreductase activities were inhibited by diclofop. Enhanced rates of passive mitochondrial swelling in isotonic KCl medium in the presence of diclofop pointed to a direct influence on the permeability properties of the inner mitochondrial membrane and indicated that membrane disruption could have been a factor in the effects elicited by diclofop on mitochondrial respiration. However, it does not appear that specific interference with mitochondrial functionality is the primary mechanism of phytotoxicity in susceptible plants.     

Compatible and antagonistic mixtures of diclofop-methyl and flamprop-methyl with herbicides used to control broad-leaved weeds

In glasshouse experiments, the addition of four ‘pyridine herbicides’ (substituted picolinic and pyridyloxyacetic acids) to either diclofop-methyl or flamprop-methyl had little effect on wild oat (Avena fatua) control. This contrasts with the serious antagonisms which occur with 2, 4-D and 2, 3, 6-TBA. With wild and cultivated oat, l'-methylheptyl (4-amino-3, 5-dichloro-6-fluoro-2-pyridyl)oxyacetate (Dowco 433) was completely compatible with diclofop-methyl and flamprop-methyl, and there was evidence that its presence improved the control of wild oats. Picloram, 3, 6-dichloropicolinic acid and triclopyr had only slight effects on phytotoxicity. The control of cleavers (Galium aparine) by picloram, triclopyr and Dowco 433 was not significantly reduced by addition of flamprop-methyl. Preliminary metabolism studies suggest that picloram does not greatly increase the rate of diclofop detoxification as do 2, 4-D and 2, 3, 6-TBA, and the observed compatibility could well be a direct consequence of this. The absence in these greenhouse experiments of serious antagonism between the pyridine herbicides and diclofop-methyl or flamprop-methyl suggests that ‘tank mixes’ of these herbicides could be used for the control of both broad-leaved weeds and wild oats.     

Abscisic acid as a protectant of Avena fatua L. against diclofop-methyl activity

The imposition of water stress before or al the time of spraying diclofop-methyl reduced efficacy against wild oat (Avena fatua L.). Similar reductions in herbicide performance were obtained by application of 20 μg of the methyl ester of abscisic acid (ABA) to plants with three to four leaves before spraying with I kg ha^?1 diclofop-methyl. Application of 40–100 μg ABA per plant effectively protected plants against damage from diclofop-methyl applied at 1 5–2 0 kg ha ^?1. The application of 20 μg ABA induced rapid stomatal closure and a reduction in leaf extension rate, which were sustained for 7–8 days after treatment. These changes were associated with an overall reduction in shoot growth. ABA-treated plants that were additionally sprayed with diclofop-methyl sustained ABA symptoms, but no additional weight loss or leaf chlorosis. The mechanism of the protective action of ABA on diclofop-methyl has not been determined.     

Use of adjuvants to improve control of black-grass (Alopecurus myosuroides Huds.) by diclofop-methyl

In pot and field experiments the addition of Ethylan D256 surfactant to spray solutions improved control of black-grass (Alopecurus myosuroides Huds.) by diclofop-methyl. Various other surfactants and oil adjuvants enhanced phytotoxicity but, generally, to a lesser extent. Ethylan D256 had most effect with applications made at early growth stages. Control of older plants was generally poor, whether or not the surfactant was added. Addition of Ethylan D256 had little effect on selectivity between A. myosuroides and cereals from lower than recommended doses of diclofop-methyl, but there was a suggestion of yield reduction from higher doses. Tank mixing with esters of ioxynil and bromoxynil sometimes improved control by diclofop-methyl but in other circumstances either had no effect or reduced phytotoxicity. Applications of diclofop-methyl in 60 or 120 1 ha^?1 spray volume were as effective as applications in 240 1 ha^?1.     

Seed oils as additives: penetration of triolein, methyloleate and diclofop-methyl in maize leaves

Methyl ester derivatives of seed oils have a greater effect on graminicide efficacy than the parent oils. To explain this difference, we investigated the penetration of the radiolabelled oils, triolein (TRI) and methyl oleate (MEO), in maize leaves, and their influence on diclofop-methyl penetration. Over a period of 3 h 30% of applied TRI penetrated maize leaves, but no further penetration was observed. In contrast, MEO entry proceeded regularly to 72% over a period of 27 h. The amount of oil found in epicuticular wax (chloroform wash) was generally less than 4% of the recovered label, and was even lower (<1%) in ‘glossy 1’ hybrids which have no crystalline epicuticular wax. In the latter plants, TRI and MEO penetration over 27 h was only 1 and 27%, respectively. Addition of an emulsifier did not modify the behaviour of the oils. The initial rate of penetration of radiolabelled diclofop-methyl into maize leaves was dramatically increased by both oils (7-5-fold by TRI, 11.8-fold by MEO). The penetration of diclofop-methyl in the leaves of ‘glossy’ hybrids was low (4% over 27 h), and it was not affected either by TRI or by the emulsifier, whereas MEO increased it sevenfold. This preliminary study shows the differences in behaviour and effect that may exist between seed oils and their methyl ester derivatives, and it emphasizes the importance of cuticular structure with regard to oil action. Utilization des huiles végétales comme adjuvants: pénétration dans les feuilles de maïs de la trioleïne, du méthyloleate et du diclofop-méthyl Les dérivés méthylestérifiés d'huiles végétales ont un effet plus important sur l'efficacité des herbicides antigraminées que les huiles d'origine. Pour expliquer cette différence, nous avons étudié la pénétration de deux huiles radioactives, la trioléine (TRI) et le méihyloléate (MEO) dans les feuilles de maïs, ainsi que leur effet sur la pénétration du diclofop-méthyl. En 3 h, 30% de TRI appliquée pénétrait les feuilles de maïs mais aucune pénétration ultérieure n'était observée. Au contraire, la pénétration de MEO se poursuivait régulièrement jusqu'à 72% en 27 h. La quantité d'huile trouvée dans les cires épicuticulaires (lavage au chloroforme) était généralement inférieure à 4% de la radioactivité récupérée, et inférieure à 1% chez les maïs ‘glossy 1’ qui n'ont pas de cires épicuticulaires cristallines. Dans ces dernières plantes, la pénétration de TRI et MEO était, respectivement, de seulement 1 et 27% en 27 h. L'addition d'un émulgateur ne modifiait pas le comportement des huiles. La vitesse initiale de pénétration du diclofop-méthyl radioactif dans les feuilles de mais était augmentée de manière importante par les deux huiles (TRI: × 7,5; MEO: × 11,8). La pénétration du diclofopméthyl dans les feuilles des hybrides ‘glossy’était faible (4% en 27 h). Elle n'était affectée ni par TRI ni par l'émulgateur alors que MEO l'augmentait (×7). Cette étude préliminaire montre les différences de comportement et d'effet qui pourraient exister entre huiles végétales et leurs dérivés méthyl ester; elle souligne aussi l'importance de la structure cuticulaire dans l'action des huiles. Aus Samen gewonnene Öle als Additive: Penetration von Triolein, Methyloleat und Diclofopmethyl in Maisblätter Methylester von aus Samen gewonnenen Ölen verbessern die Wirksamkeit von Graminiziden mehr als die Grundstoffe. Um diese Unterschiede genauer zu erkennen, wurde die Penetration der radioaktiv markierten Ole Triolein (TRI) und Methyloleat (MEO) in Maisblätter und ihr Einfluβ auf die Aufnahme von Diclofop-methyl untersucht. In 3 h wurden 30% des applizierten TRI von Maisblättern aufgenommen, aber eine weitere Aufnahme wurde nicht festgestellt. Im Gegensatz dazu wurde MEO innerhalb 27 h kontinuierlich bis zu 72% aufgenommen. Die Menge des in der epikutikularen Wachsschicht gefundenen Öls (Lösung in Chloroform) war allgemein <4% der wiedergefundenen Radioaktivität und war sogar geringer (< 1%) in ‘Glossy-1’-Hybriden, die kein kristallines epikutikulares Wachs haben. Bei solchen Pflanzen lag die TRI- und die MEO-Penetration in 27 h bei nur 1 bzw. 27%. Durch Zugabe eines Emulgators konnte das Verhalten der Öle nicht geändert werden. Die anfängliche Aufnahmerate für das radioaktiv markierte Diclofop-methyl in Maisblättern wurde durch beide Öle auβerordentlich gesteigert (TRI: 7,5 mal; MEO: 11,8 mal). Die Penetration von Diclofop-methyl in die Blätter der ‘Glossy’-Hybriden war gering (4% in 27 h). Durch TRI oder den Emulgator wurde sie nicht beeinfluβt, mit MEO jedoch gesteigert (7mal). Diese vorläufige Untersuchung zeigt Unter-schiede in Verhalten und Wirkung der Öle und ihrer Methylester, und sie unterstreicht die Bedeutung der kutikularen Strukturen für die Wirkung von Ölen.     

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.     

The role of fungal endophyte infection in the evolution of Lolium multiflorum resistance to diclofop-methyl

Diclofop-methyl resistance was evaluated in populations of Italian ryegrass ( Lolium multiflorum Lam.) infected and uninfected with fungal endophyte ( Neotyphodium ). Survival was tested in susceptible populations using herbicide screening. The results served as inputs to a model for investigating the role of endophyte infection in the evolution of L. multiflorum resistance to herbicide. The tolerance of infected plants varied depending on the origin of the population and the herbicide dose. Only in some populations and at some diclofop-methyl doses did plants infected with these endophytes have higher survivorship than endophyte-free plants. The model demonstrated that endophytes might indeed play an important role in the evolution of herbicide-resistant weeds, delaying the appearance of herbicide resistance.     

Resistance to diclofop-methyl in two Lolium spp. populations from Italy: studies on the mechanism of resistance

The mechanisms of herbicide resistance were investigated in two diclofop-methyl-resistant Lolium spp. populations from central Italy, Roma '94 and Tuscania '97. These two populations were compared with two susceptible Italian populations (Vetralla '94, Tarquinia '97) and a resistant and a susceptible population from Australia, SLR31 and VLR1. The activity of acetyl Co-A carboxylase (ACCase) extracted from susceptible (S) or resistant (R) individuals from the Italian populations was inhibited by both aryloxyphenoxypropanoate (diclofop acid and fluazifop acid) and cyclohexanedione (sethoxydim) herbicides. Diclofop-methyl was rapidly de-esterified to diclofop acid at a similar rate in both R and S populations. In all populations, diclofop acid was subsequently degraded to other metabolites. The rate of degradation of diclofop acid was not significantly faster in R than in S populations; however, diclofop acid was degraded more completely in Roma '94 and Tuscania '97 compared with the S populations. Application of the mixed-function oxidase inhibitor 1-aminobenzotriazole (ABT) significantly enhanced diclofop-methyl toxicity towards both R populations, but not in S populations. However, enhanced herbicide metabolism does not completely account for the measured resistance level. A mechanism other than an altered ACCase and enhanced herbicide metabolism appears to be responsible for resistance to diclofop-methyl in Roma '94 and Tuscania '97.     

The influence of temperature on barley (Hordeum vulgare L.) tolerance to diclofop-methyl or fenoxaprop-P-ethyl mixtures

The influence of temperature and evaluation date on the biological activity of diclofop-methyl or of herbicide mixtures containing fenoxaprop-P-ethyl in barley were investigated. Herbicidal injury was evaluated based upon per cent fresh weight reduction compared with untreated plants. ‘Ellice’ barley was injured more than ‘Bonanza’ or ‘TR112’ at 25/20°C (day/night), averaged over herbicides and evaluation dates. Diclofop-methyl injury was similar at 10/8°C, 17/14°C, and 25/20°C, averaged over evaluation dates. However, injury increased from 1 week after treatment to 2 weeks after treatment at 10/8°C and 17/14°C but not at 25/20°C. This injury appeared to be related to plant growth rate, as the greatest injury of treated plants and the greatest fresh weight of untreated plants at 2 weeks after treatment were observed at 17/14°C. A formulated mixture of fenoxaprop-P-ethyl plus the safener fenchlorazole-ethyl was the most injurious to barley while a mixture of fenoxaprop-P-ethyl plus chlorophenoxy herbicides injured barley to a lesser degree, and was similar to injury from diclofop-methyl. Injury from either of the two herbicide mixtures containing fenoxaprop-P-ethyl was greatest at 10/8°C. Influence de la température sur la tolérance de l'orge (Hordeum vulgare L.) au diclofop-méthyl et à des mélanges contenant du fénoxaprop-P-éthyl L'influence de la température et de la date d'évaluation sur l'activité biologique du diclofopméthyl et de mélanges d'herbicides contenant du fénoxaprop-P-éthyl a étéétudiée chez l'orge. L'effet herbicide était évalué par le pourcentage de réduction de matière fraîche par rapport au témoin. La variété‘Ellice’était plus touchée que les variétés ‘Bonanza’ ou TR112' à 25/20°C (lumière/obscurité), les herbicides et les dates d'évaluation étant confondus. La phototoxicité du diclofop-méthyl était similaire à 10/8°C, 17/14°C et 25/20°C, les dates d'évaluation étant confondues. La phytotoxicité augmentait entre une et deux semaines après le traitement à 10/8°C et 17/14°C, mais pas à 25/20°C. Cette phytotoxicité paraissait liée à la vitesse de croissance car la phytotoxicité sur plantes traitées et le traitement étaient maximaux à 17/14°C. Un mélange formulé de fénoxaprop-P-éthyl et de l'antidote fenchlorazole-éthyl était le plus phytotoxique. Le diclofop-méthyl ainsi qu'un mélange de fénoxaprop-P-éthyl et d'herbicides phénoxy-chlorés étaient les moins phytotoxiques. La phytotoxicité occasionnée par les deux mélanges contenant du fénoxaprop-P-éthyl était plus importante à 10/8°C. Einfluß der Temperatur auf die Toleranz von Gerste (Horde um vulgäre L.) gegenüber Diclofop-methyl oder Fenoxaprop-P-ethyl-Präparaten Zur Untersuchung des Einflusses der Temperatur auf die Wirkung von Diclofop-methyl oder Fenoxaprop-P-ethyl-haltigen Herbiziden auf Gerste wurde der Herbizidschaden in % der Frischmasse unbehandelter Pflanzen zu verschiedenen Terminen bestimmt. Die Sorte ‘Ellice’ wurde bei 25/20°C im Mittel über die Herbizide und die Termine stärker geschädigt als ‘Bonanza’ oder ‘TR112’. Die Schädigungen durch Diclofop-methyl waren bei 10/8, 17/14 und 25/20°C, gemittelt über die Boniturtermine, ähnlich. aber die Schäden nahmen bei den beiden niedrigeren Temperaturbereichen, doch nicht bei 25/20°C, von der 1. zur 2. Woche nach der Behandlungzu. Der Schaden lag offensichtlich in der Wachstumsrate, denn er war nach 2 Wochen bei 17/14°C bei den behandelten Pflanzen am höchsten, als bei den unbehandelten Pflanzen die Frischmasse am größten war. Eine Fenoxaprop-P-ethyl-Formulierung mil dem Safener Fenchlorazol-ethyl schädigte die Gerste sehr, während eine Mischung von Fenoxaprop-P-ethyl mit Chlorphenoxy-Herbiziden weniger schädigte, ähnlich wie Diclofop-methyl. Die Schäden von den beiden Fenoxaprop-P-ethyl-Herbiziden waren bei 10/8°C am stärksten.