In vitro activity and binding characteristics of the hydroxybenzonitriles in chloroplasts isolated from Matricaria inodora and Viola arvensis

The electron transport inhibition, uncoupling, and binding of ioxynil and bromoxynil salts is compared in chloroplast fragments isolated from two weed species with contrasting responses to the hydroxybenzonitriles. Ioxynil Na was three to four times more inhibitory than bromoxynil K towards DCPIP and SiMo reduction in both Matricaria inodora and Viola arvensis. Ioxynil Na was also a more potent uncoupler of PSI-dependent electron transport from ascorbate/DCPIP to methyl viologen. Uncoupling occurred at concentrations higher than those that inhibited electron transport. Binding studies with [¹⁴C]bromoxynil K and [¹⁴C]ioxynil Na salts revealed slightly biphasic curves with no significant difference in the amounts of the two herbicides bound at a given concentration. The ratios of inhibition constant (K_i) and binding constant (K_b) were approximately one for ioxynil Na and three for bromoxynil K. Radiolabelled herbicide displacement studies revealed that ioxynil Na could partially displace bound [¹⁴C]bromoxynil K, but bromoxynil K could not displace bound ioxynil Na at biochemically active concentrations. Ioxynil Na may be a more effective inhibitor than bromoxynil K because it binds more strongly to the thylakoid membrane.     

Control of Galium aparine (cleavers) in winter cereals with mecoprop alone or with ioxynil plus bromoxynil

A series of eleven field experiments over two seasons investigated the control of Galium aparine (cleavers) with mecoprop and a proprietary mixture of ioxynil plus bromoxynil. Applications of mecoprop (2?4 kg a.e. ha^?1) between December and March gave variable results but a mixture of ioxynil + bromoxynil (0?6 kg a.i. ha^?1) and mecoprop improved control up to at least 90%, at most sites. Applications of mecoprop alone in April were most effective and frequently achieved more than 90% control. In May, when the G. aparine plants were very large, it was less successful. The reasons for the environmental effects on performance are discussed. Preliminary examination of the effect of soil temperature on mecoprop activity indicates that the reliability of control increases with increasing temperature (0–12°C). An average of 94% control was achieved when soil temperatures were greater than 6°C. La destruction de Galium aparine (Gaillet) dans les cereales d'hiver avec du mecoprop seul ou avec ioxynil plus bromoxynil     

Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS)

It is shown that potentially persistent transformation products can be formed from the herbicides bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) and ioxynil (3,5-diiodo-4-hydroxybenzonitrile), and possible leaching to groundwater is discussed. A similar process to the formation of BAM (2,6-dichlorobenzamide) from the herbicide dichlobenil (2,6-dichlorobenzonitrile) can be anticipated as bromoxynil and ioxynil are analogues of dichlobenil and they are degraded by the enzymes nitrilase, nitrile hydratase and amidase. A biodegradation study using cultured Variovorax sp. DSM 11402, a species commonly found in soil, demonstrated that ioxynil and bromoxynil were fully transformed into their corresponding amides in 2-5 days. These amides were not further degraded within 18 days, and formation of other degradation products was not observed. These results are in agreement with biodegradation experiments with dichlobenil. In soil, dichlobenil is transformed into its only observed degradation product BAM, which is persistent and mobile, and has been found in 19% of 5000 samples of Danish groundwater. Variovorax sp. is known to degrade the non-halogenated analogue benzamide, suggesting that degradation of the three amides may be hindered by the halogenated substituents (meta-Br; meta-I; ortho-Cl). This hypothesis is supported by QSAR modelling of fundamental properties. Using a new optimised liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, the sorption and desorption properties of bromoxynil and ioxynil were characterised in sandy topsoil at four concentration levels. The estimated sorption coefficient K(d) was 1.4 L kg(-1) for bromoxynil and 5.4 L kg(-1) for ioxynil, indicating weak to moderate sorption to topsoil. Desorption of the herbicides showed that they were strongly and irreversible bound to the soil (K(des) > K(d)). The amount of herbicide desorbed depended on the initial concentration level. At low levels, K(des) values were higher, indicating stronger binding than at higher levels. The isocratic LC-MS/MS method developed for simultaneous detection of bromoxynil, ioxynil and their main degradation products is described. Using negative electrospray ionisation (ESI-), the detection limits were 0.4-1.0 microg L(-1), with relative standard deviations of 4-10% (n = 10) using direct injection without clean-up steps. The standard curves showed linearity in the range 5-100 microg L(-1) with r(2) > 0.992.     

Glasshouse trials with controlled drop application of some foliage-applied herbicides

MCPA, mecoprop, dichlorprop, dicamba, 2,3,6-TBA, bentazone, ioxynil/bromoxynil (a mixture), barban, difenzoquat and chlorfenprop-methyl were applied by spinning disc in controlled drop sizes from 150-350μm and at very low volume rates (5–45 1/ha), to the foliage of some dicotyledonous weed species or wild oats (Avena fatua L.). The same herbicides were also applied by means of conventional hydraulic nozzles at volume rates of about 200 1/ha. Most of these herbicides performed as well at very low volume rates as with the conventional application, the major exceptions being bentazone, ioxynil/bromoxynil (both of which have distinct contact effects) and dichlorprop. Comparisons between oil and water as the diluent at a very low volume rates suggest that there may be situations when oil is preferable and others when water is.     

The effect on yield of mixtures and sequences of herbicides for the control of Alopecurus myosuroides Huds. and broad-leaved weeds in winter cereals

Mixed infestations of Alopecurus m yosuroides Huds. and broad-leaved weeds in winter cereals were controlled with a commercial formulation of ioxynil + bromoxynil + mecoprop. used in mixtures or as sequences with isoproturon or clofop-isobutyl. As well as controlling A. myosuroides the mixtures, applied in the autumn, gave good control of Veronica persica Poir., Galium aparine L. Lilhospermum arvense L. and Viola arvensis Murr. weeds which were resistant to isoproturon used alone. A. myosuroides had the major influence on crop yield in three experiments. High infestations of A. myosuroides reduced the broad-leaved weeds so that crop yields were only slightly improved when all the weeds were controlled compared with the control of A. myosuroides alone. In the remaining experiment. V. persica was very competitive with wheat; additional control of A. myosuroides improved yields considerably. Ioxynil + bromoxynil + mecoprop gave better final control of broad-leaved weeds when applied in the spring rather than the autumn but the sequence of a spring application following isoproturon or clofop-isobutyl in the autumn did not improve yields compared with the mixtures applied in the autumn. In all experiments, the highest yields were obtained from controlling both A. myosuroides and broad-leaved weeds in the autumn, provided that good control of A. myosuroides was obtained.     

喹草酮与辛酰溴苯腈复配应用于小麦田的除草效果及对小麦的安全性

为明确新型除草剂喹草酮应用于小麦田的除草效果及对小麦的安全性,在温室内采用共毒系数法对喹草酮与辛酰溴苯腈联合作用进行测定,并验证喹草酮与辛酰溴苯腈两者混用以及与双氟磺草胺三者混用时对小麦田杂草的防效,以及对小麦的安全性。温室试验结果表明,喹草酮对阿拉伯婆婆纳Veronica persica防效优,试验剂量下全部死亡,对播娘蒿Descurainia sophia和麦家公 Lithospermum arvense的GR₅₀分别为12.67 g （a.i.）/hm²和152.99 g （a.i.）/hm²;辛酰溴苯腈对播娘蒿和麦家公防效优,其GR₅₀分别为26.22 g （a.i.）/hm²和13.36 g （a.i.）/hm²,对阿拉伯婆婆纳防效略差,GR₅₀为85.12 g （a.i.）/hm²。喹草酮与辛酰溴苯腈按有效成分用量1：1~1：2.5配比时,阿拉伯婆婆纳全部死亡,对播娘蒿的共毒系数在140.34~202.77之间,呈明显增效作用,对麦家公的共毒系数达700.00以上,也呈明显增效作用。田间试验结果表明,喹草酮对阿拉伯婆婆纳防效高,而对猪殃殃Galium aparine和播娘蒿略差;辛酰溴苯腈作用速度快,但后期部分杂草返青,喹草酮与辛酰溴苯腈复配后优势互补,对小麦田阔叶杂草阿拉伯婆婆纳、猪殃殃和播娘蒿防效均优,鲜重防效在88.54%~ 93.83%之间,且杂草死亡速度快,在2种药剂基础上加入双氟磺草胺后,鲜重防效在96.12%以上。喹草酮单剂或与辛酰溴苯腈、双氟磺草胺的混配处理不影响小麦的正常生长。     

Bromoxynil degradation in a Mississippi silt loam soil

BACKGROUND: The objectives of these laboratory experiments were: (1) to assess bromoxynil sorption, mineralization, bound residue formation and extractable residue persistence in a Dundee silt loam collected from 0–2 cm and 2–10 cm depths under continuous conventional tillage and no‐tillage; (2) to assess the effects of autoclaving on bromoxynil mineralization and bound residue formation; (3) to determine the partitioning of non‐extractable residues; and (4) to ascertain the effects of bromoxynil concentration on extractable and bound residues and metabolite formation. RESULTS: Bromoxynil K_d values ranged from 0.7 to 1.4 L kg^?1 and were positively correlated with soil organic carbon. Cumulative mineralization (38.5% ± 1.5), bound residue formation (46.5% ± 0.5) and persistence of extractable residues (T_1/2 < 1 day) in non‐autoclaved soils were independent of tillage and depth. Autoclaving decreased mineralization and bound residue formation 257‐fold and 6.0‐fold respectively. Bromoxynil persistence in soil was rate independent (T_1/2 < 1 day), and the majority of non‐extractable residues (87%) were associated with the humic acid fraction of soil organic matter. CONCLUSIONS: Irrespective of tillage or depth, bromoxynil half‐life in native soil is less than 1 day owing to rapid incorporation of the herbicide into non‐extractable residues. Bound residue formation is governed principally by biochemical metabolite formation and primarily associated with soil humic acids that are moderately bioavailable for mineralization. These data indicate that the risk of off‐site transport of bromoxynil residues is low owing to rapid incorporation into non‐extractable residues. Published 2009 by John Wiley & Sons, Ltd     

Studies on the effects of herbicides on soil nitrification,II

The effects of selected herbicides have been studied on the following parameters of soil nitrification processes: the rates of nitrate and nitrite formation from ammonia in freshly perfused soils and in soils previously saturated with nitrifying organisms in an improved perfusion apparatus; the rates of oxygen consumption and of oxidation of ammonia and nitrite in washed cell suspensions of Nitrosomonas europaea and Nitrobacter winogradskii, respectively; the rates of growth of those two organisms in newly established cultures; the rates of oxygen uptake by soil enriched in nitrifying organisms; the rates of proliferation of nitrifying populations in freshly perfused soil. ID50 values were computed for all parameters and herbicides studied. On average, the most sensitive parameters were the metabolism and growth of the two organisms in pure culture, while the least sensitive were the corresponding measures in the soil environment. Similarly, herbicides fell into four distinct groups. The most toxic were the formulated octanoates of bromoxynil and ioxynil (NPH1320 and Totril, respectively); next in order of toxicity were chlorbufam, phenmedipham, formulated oxadiazon, formulated legurame, ioxynil, formulated trifluralin, and bromoxynil; low toxicity was shown by terbacil, dicamba, and tricamba, whereas asulam and the related experimental herbicide MB9555 showed activity on some parameters at the very highest concentrations only. Comparisons of soil with pure-culture parameters showed that the relative toxicities of herbicides to Nitrosomonas in culture bore little relationship to those in soil. The inhibitions of Nitrobacter proliferations in soil on the other hand were correlated with the inhibitions of growth and metabolism in pure culture. Within these overall effects, individual herbicides showed marked differential actions on various parameters. Thus, the formulated octanoates of bromoxynil and ioxynil were extremely toxic to the growth of nitrifying organisms in culture, an action probably due to an unknown formulation component. Relative to other herbicides, bromoxynil and ioxynil were more effective on nitrification processes in the soil environment. Both in culture and in the soil, Nitrobacter is more sensitive than Nitrosomonas to these four herbicides. Legurame and oxadiazon are relatively more toxic to Nitrosomonas in culture, but this differential action is not demonstrable in the soil. Dicamba, tricamba, trifluralin, and chlorbufam are more toxic to Nitrobacter than to Nitrosomonas in the soil environment. Formulated trifluralin seems to exert a stimulating action on the growth of nitrifying organisms, but only in the soil; suppression of antagonistic organisms is suggested as a possible cause. Extrapolation of these results to the field situation suggests that the only herbicide which might cause small inhibitions of nitrification at field rates is terbacil, which is disproportionately toxic at low concentrations. At rates somewhat in excess of normal, the formulated octanoates of bromoxynil and ioxynil and possibly dicamba and oxadiazon could also cause small inhibitions.     

Communication to the Editor Degradation of Bromoxynil,Ioxynil, Dichlobenil and their Mixtures by Agrobacterium radiobacter 8/4

Degradation of three benzonitrile herbicides, bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), ioxynil (3,5-diiodo-4-hydroxybenzonitrile), dichlobenil (2,6-dichlorobenzonitrile), and their mixtures by the soil micro-organism Agrobacterium radiobacter 8/4 was studied in batch cultures. Bromoxynil was found to be most rapidly degraded, while dichlobenil had the lowest toxicity to our strain. All transformations of studied benzonitriles were performed by the nitrile hydratase which has been shown to act on a broad range of substituted aromatic nitriles. © 1997 SCI.     

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.     

Recovery of non-target plants affected by airborne bromoxynil-octanoate and metribuzin

The present study was conducted to evaluate the recovery potential of non‐target plants affected by two airborne herbicides. Sunflower at the two‐leaf stage was used as a test plant and exposed for 24 h in a wind tunnel to a range of concentrations of airborne bromoxynil‐octanoate and metribuzin. Quantum yield (φ_PSII) of exposed leaves and of the second leaf pair developed after exposure was determined at a particular time up to 16 days following exposure. Maximum depression in quantum yield of exposed leaves from which a complete recovery occurred within 16 days was 63% for bromoxynil‐octanoate and 60% for metribuzin respectively. The corresponding maximum concentrations were 1.310 and 0.390 μg m^?3 respectively. The second leaf pair was also affected and showed a similar recovery potential. From the results it can be concluded that the significance of airborne bromoxynil‐octanoate and metribuzin must not be overestimated, as sunflower and non‐target plants with a similar sensitivity are likely to recover from air concentrations of both herbicides reported under field conditions.     

Degradation of ioxynil to CO2 in soil

Degradation of ioxynil (4-hydroxy-3,5-diiodobenzonitrile) to CO₂ was detected in a clay loam, high organic matter content soil. The majority of radioactivity was recovered as ¹⁴CO₂ from both ring-labeled and cyano-labeled ioxynil; however, ¹⁴CO₂ was always released from cyano-labeled ioxynil at a much faster initial rate. No ¹⁴CO₂ was released in treated sterile soil, either aerobically or anaerobically. Production of ¹⁴CO₂ from cyanolabeled and ring-labeled ioxynil was greatly inhibited by HgCl₂ (10^?5M), and p-chloromercuribenzoate (5 × 10^?5M), but slightly inhibited by ferricyanide (10^?4M). No ¹⁴CO₂ was evolved from ring-labeled ioxynil under anaerobic conditions. These observations indicated that the degradation of ioxynil to CO₂ in soil was a microbial action and was oxygen dependent. This is consistent with the known mechanism of oxygenases in degrading benzene rings. Anaerobically, a small amount of ¹⁴CO₂ was released from cyano-labeled ioxynil. Thin-layer chromatographic analyses of the culture supernatant revealed that 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid were intermediate metabolites.     

Asulam mixtures for weed control in flax

Five field experiments were conducted from 1972 to 1975 to evaluate weed control in flax (Linum usitatissimum L.) using post-emergence treatments of asulam [methyl (4-aminobenzenesulphonyl) carbamatel alone and in combination with other herbicides. The ¹⁴C-asulam absorption by leaf segments and roots of glasshouse grown wild oats (Avena fatua L.) was also investigated. Asulam at 1.12 kg/ha gave good wild oat control and acceptable control of green foxtail (Setaria viridis (L.) Beauv.). However, wild oat control was poorer when asulam was combined with other herbicides: on a 3-year average, as compared with asulam alone at equal rates, the asulam+MCPA mixture resulted in a greater antagonism and a significant 6% reduction in flax seed yield, whereas the asulam+bromoxynil/MCPA mixture gave the least antagonistic effect, improved broadleaf weed control and increased yield by 13%. In mixtures, the potassium salt of MCPA was more compatible with asulam for weed control than the amine form. Both leaf segments and roots of wild oats absorbed and distributed less ¹⁴C-asulam from solutions containing MCPA than from those containing bromoxynil or bromoxynil/MCPA.     

Effect of some substituted benzonitriles on photosynthetic activity of spinach and wheat in vivo and in vitro

The inhibitory effects of nine nitro and/or bromo-substituted benzonitrile compounds on the photosynthetic electron flow in isolated chloroplasts and on the in vivo CO₂ fixation of spinach (Spinacia oteracea L.) and wheat (Triticum aesticum L. cv. Bezoslaya) were investigated. Bromoxynil and 3-nitro-5-hromo-4-hydroxy-bcnzonitrile were the strongest and equally effective inhibitors of Ihe in vivo CO₂ fixation of spinach, hut in wheat the nitro-bromo-compound is ineffective and 3-nitro-benzonitrile is even more inhibitory than bromoxynil. None of the substances affected DCPIPH → methylviologen reduction. In the inhibition of the DCPIP reduction only the 3,5-disuhstituted 4-hydroxy-derivatives were effective. The fact that these compounds affect only the PS II reaction with both H₂O and DPC as electron donors suggests a site of inhibition on the reducing side of PS II, between Ihe PS II reaction centre and ihe DCPIP Site. It is suggested that in the inhibition of the DCPIP reduction only steric factors are important and the different electron configuration of the sterieally similar molecules may be involved only in the absorption and translocation processes of the compounds.     

Use of a potentiometric vital dye to determine the effect of the herbicide bromoxynil octanoate on mitochondrial bioenenergetics in Chlamydomonas reinhardtii

BACKGROUND: The aims of the present study were to validate a vital mitochondrial potentiometric staining method in Chlamydomonas reinhardtii and to utilise this method to examine the effect of the herbicide bromoxynil octanoate on mitochondrial potential in this species. A range of stains was investigated, including Rhodamine 123, DASPMI, Mitotracker Green, Mitotracker Orange and JC‐1. RESULTS: Rhodamine 123 (R123) had the highest utility of several candidate stains. Incubation with both 5 and 10 µM carbonyl cyanide 3‐chlorophenylhydrazone caused significant fluorescence collapse [Dunn's post test (40.00, P < 0.01) and (45.49, P < 0.01) respectively], demonstrating that the R123 fluorescence reported mitochondrial potential. The effect of the herbicide bromoxynil octanoate was examined. Exposure to 0.1 mM of bromoxynil resulted in a significant increased mitochondrial fluorescence compared with the baseline (Mann–Whitney U = 222, P < 0.002), while concentrations of 1 mM and greater resulted in significant, almost complete loss of mitochondrial potential [mean fluorescence ratio = 1.193–1.289 (where a ratio of 1 represents total potential loss), Mann–Whitney U = 0.0, P < 0.001 (1 mM ), 0.0, P < 0.0001 (2 mM ), 0.0, P < 0.0001 (5 mM )]. EC₅₀ of the collapse in mitochondrial potential owing to bromoxynil incubation occurred at 0.72 mM , and the mean t₅₀ of bromoxynil octanoate action was 93 s. CONCLUSIONS: R123 is a sensitive potentiometric dye in C. reinhardtii that may find further use in investigations of both mitochondrial bioenergetics in plants and environmental toxicology. Copyright © 2011 Society of Chemical Industry     

Interaction between glyphosate and various herbicides for broadleaved weed control

The effects of several herbicides for broadleaved weed control on glyphosate (n-phosphonomethyl glycine) phytotoxicity to wheat (Triticum aestivum L.), barley (Hordeum vulgare L.) and wild oats (Avena fatua L.) were studied in the greenhouse. In tank mixtures, dicamba (3,6-dichloro-o-anisic acid), 2,4-D (2,4-dichlorophenoxy-acetic acid) and bromoxynil (3,5-dibromo-4-hydroxy benzonitrile) reduced the phytotoxicity of threshold rates of glyphosate on all three species. With increasing rates of the herbicides for broadleaved weed control relative to a fixed rate of glyphosate, there was a general trend towards increased antagonism. Increasing glyphosate rates above the threshold level in mixtures containing a fixed rate of herbicides for broadleaved weed control overcame the antagonism. Both the inert and active ingredients of 2,4-D amine and ester appeared to be involved in the antagonism. There was no reduction in glyphosate phytotoxicity on the annual grasses when 2,4-D or bromoxynil were sprayed sequentially at various times in relation to glyphosate. When droplets of bromoxynil and glyphosate were placed side by side on a leaf, glyphosate phytotoxicity was not reduced, whereas when the two herbicides were mixed and applied as one droplet, considerable reduction in glyphosate phytotoxicity occurred. These results suggest that the reduction in glyphosate phytotoxicity caused by tank mixing with herbicides such as 2,4-D, bromoxynil and dicamba may be due to a physical or chemical incompatability within the tank mixture rather than to a biological interaction in the plant.     

CHEMICAL AND BIOLOGICAL PROPERTIES OF TWO NEW HERBICIDES—IOXYNIL AND BROMOXYNIL

Summary. The preparation of ioxynil, bromoxynil, and their salts is described, and information on solubilities and stability to storage is summarized. Although the toxicology of the herbicides is to be reported in greater detail, a preliminary statement is made here. Evidence of herbicidat activity under glasshouse conditions is indicated briefly, and supports the conclusion that both compounds are effective when applied to the foliage of a wide range of dicotyledon weed species. Seedlings of some weed species resistant to the phenoxy alkanoic acids are controlled under glasshouse conditions at doses as low as 0.125 lb/ac, and ioxynil has a wider range of activity than bromoxynil at these low doses. Graminaceous species tolerate 4–8 lb/ac of both herbicides without injury, and certain leguminous crops tolerate one or other herbicide at doses of 0.5–0.75 lb/ac. The contact action of the herbicides is rapid, there are also slower systemic effects, and seed germination is inhibited. In susceptible species the level of post-emergence activity is shown to be influenced by the growth stage of the weed, the distribution of herbicide on the foliage, and environmental factors of which light intensity appears to be most important.
Propriétés chimiques et biologiques de deux nouveaux herbicides: ioxynil et bromoxynil     

Physiological basis for antagonism induced by mixtures of quizalofop-ethyl and bromoxynil in maize (Zea mays)

In this study, the physiological basis for antagonism induced by mixtures of quizalofop‐ethyl and bromoxynil was investigated in maize seedlings. In sequential applications, antagonism was observed when bromoxynil was applied before quizalofop‐ethyl or in a mixture with quizalofop‐ethyl, but was minimal when bromoxynil was applied afterwards. The degree of antagonism differed with application rates of bromoxynil and with the timing of the treatment. When test herbicides were applied locally to the second leaf, the inhibition of photosystem II (PS‐II) in the herbicide‐treated leaf was higher with the mixture than with bromoxynil or quizalofop‐ethyl alone. Subsequent growth of the untreated third leaf inhibited by quizalofop‐ethyl alone then recovered, depending on the dose of bromoxynil. There was no evidence that bromoxynil affected absorption of quizalofop‐ethyl. In local applications at different positions on the second leaf, antagonism was only observed when quizalofop‐ethyl was applied to the distal part of the leaf and bromoxynil applied to the proximal part. The antagonism of bromoxynil + quizalofop‐ethyl did not occur at the level of acetyl CoA carboxylase and Hill reaction, as revealed by in vitro assays. These results suggest that bromoxynil inhibits the phloem transport of quizalofop‐ethyl and thus antagonises its whole‐plant activity in maize.     

THE BASIS OF THE DIFFERENTIAL PHYTOTOXICITY OF 4-HYDROXY-3,5-DI-IODOBENZONITRlLE*

Summary. Entry of ioxynil-¹⁴C into portions of leaves was greater with mustard than with barley or pea and was unrelated to stomatal density. Measurement of ioxynil content of sprayed plants showed that by increasing the concentration of ioxynil and adding a surfactant, almost as much ioxynil could be made to enter barley as entered mustard from a lower concentration without surfactant. Auto radiographs showed that a limited amount of ¹⁴C was translocated to a small extent in plants following localized application of ioxynil-¹⁴C. An experiment comparing leaf removal by cutting with destruction of equivalent leaf areas by ioxynil treatment suggested a greater translocated effect of ioxynil with mustard than with pea or barley. Les principes de la phytotoxicité différentielle du 4-hydroxy-3,5-di-iodobetZonitrile II. Absorption et migration     

Interaction of ioxynil and mecoprop when applied to Stellaria media (L.) Vill.

The interaction of ioxynil and mecoprop applied to Stellaria media (L.) Vill. was investigated under controlled environmental conditions and several statistical methods were used to test for positive or negative interactions employing a multiplicative survival model. Information on the contribution of each herbicide to the total effect was gained by recording numbers of shoots and leaves, internode length and photosynthetic carbon dioxide exchange. Results showed that ioxynil and mecoprop can interact strongly, but the degree and direction of this interaction varied according to both the growth stage of the plants at spraying and the length of time between spraying and assessment of response. In general a synergistic interaction occurred where plants were younger at spraying and with a longer period of time between spraying and assessment of effects. These results are discussed in relation to the potential for using reduced doses of this herbicide mixture, and the importance of the design and interpretation of interaction studies are considered. Action réciproque de l'ioxynil et du MCPP appliqués sur Stellaria media (L.) Vill. L'action réciproque de l'ioxynil et du MCPP, appliqués sur Stellaria media (L.) Vill., a fait l'objet d'une étude dans des conditions ambientales contrôlées; plusieurs méthodes d'analyse statistique ont été mis en oeuvre pour déceler des actions réciproques positives ou négatives en utilisant un modèle multiplicatif de survivance. Les nombres de pousses et de feuilles, la longeur de l'entre-noeud et l'échange photosynthétique de l'acide carbonique ont été signalés pour obtenir des renseignements sur la part de chaque herbicide dans l'effet global. Les résultats ont révélé que l'ioxynil et le MCPP sont capables d'une forte action réciproque mais le niveau et le sens de cette interaction ont varié selon le stade de développement des plantes au moment de la pulvérisation ainsi que l'intervalle entre la pulvérisation et l'évaluation de la réaction. En général, une interaction synergique s'est fait voir plus les plantes étaient jeunes au moment de la pulvérisation et plus l'intervalle entre celle-ci et l'evaluation des effets était grand. Ces résultats sont discutées par rapport à la possibilité d'employer des doses réduites de cette association herbicide; on considère aussi l'importance du plan expérimental et de l'interprétation dans les études d'actions réciproques. Wechselwirkung von Ioxynil und Mecoprop auf Stellaria media (L.) Vill. Am Beispiel von Stellaria media (L.) Vill. wurde das Zusammenwirken von Ioxynil und Mecoprop unter kontrollierten Umweltbedingungen studiert. An einem multiplikativen Ueberlebensmodell wurden verschiedene statistische Methoden eingesetzt, um positive oder negative Wechselwirkungen aufzudecken. Zur Erarbeitung der notwendigen Information über den Beitrag jedes Herbizids zur Gesamtwirkung wurden folgende Parameter bestimmt: Anzahl Sprosse und Blätter, Länge der Internodien und der photosynthetische CO₂-Austausch. Die Resultate zeigten, dass Ioxynil und Mecoprop stark zusammenwirken können, wobei aber Grad und Qualität der Wechselwirkung (positiv oder negativ) je nach Alter der Pflanzen bei der Behandlung und Intervall zwischen Behandlung und Messung der Reaktion variierten. Der Trend zu Synergismus war umso ausgeprägter, je jünger die Pflanzen bei der Behandlung und je länger die Intervalle zwischen letzterer und den Messungen waren. Die Ergebnisse werden einerseits im Hinblick auf die Möglichkeit der Verwendung reduzierter Aufwandmengen dieser Herbizidmischung diskutiert, aber auch bezüglich der Wichtigkeit der Versuchsanlage zur Interpretation von Untersuchungen über Wechselwirkungen.