Persistence of terbacil and trifluralin under different soil and climatic conditions

Soil samples were collected from forty-three field trials conducted on ten soil types to investigate the residual activity of terbacil and trifluralin at the end of the cropping season, approximately 6 months after application. The soil was bioassayed in a glasshouse using soya beans and German millet for terbacil and trifluralin respectively. At 1 kg/ha terbacil phytotoxic residues occurred in a majority of the trials, while at 2 kg/ha such a carry-over could be found in every case. Trifluralin doses of up to 1 kg/ha did not persist in toxic amounts in most soils, while application of 2 kg/ha showed residual activity in 74% of the trials and application of 4 kg/ha killed German millet in all instances. Results are also presented from the time-rate dissipation studies conducted on both herbicides by assaying soil samples collected at monthly intervals. Both organic matter and clay content of the trial sites affected the persistence of terbacil, while trifluralin residues were influenced only by the soil organic matter content. Trial sites receiving high rainfall showed considerably less residues of terbacil, but the persistence of trifluralin was not affected by rainfall to any appreciable extent.     

Measurement and modelling of glyphosate fate compared with that of herbicides replaced as a result of the introduction of glyphosate-resistant oilseed rape

BACKGROUND: Crops resistant to glyphosate may mitigate the increasing contamination of the environment by herbicides, since their weeding requires smaller amounts of herbicides and fewer active ingredients. However, there are few published data comparing the fate of glyphosate with that of substitute herbicides under similar soil and climatic conditions. The objectives of the work reported here were (i) to evaluate and compare the fate in soil in field conditions of glyphosate, as used on glyphosate-resistant oilseed rape, with that of two herbicides frequently used for weed control on the same crop, albeit non-resistant: trifluralin and metazachlor, and (ii) to compare field results with predictions of the pesticide root zone model (PRZM), parameterized with laboratory data. Dissipation and vertical distribution in the soil profile of glyphosate, trifluralin and metazachlor were monitored in an experimental site located in Eastern France for 1 year. RESULTS: Herbicide persistence in the field increased as follows: metazachlor < glyphosate < trifluralin, contrary to laboratory results showing glyphosate to be least persistent. The main metabolite of glyphosate-aminomethylphosphonic acid (AMPA)-was more persistent than glyphosate. AMPA and trifluralin had the largest vertical mobility, followed by metazachlor and glyphosate. PRZM underestimated the dissipation rate of glyphosate in the field and the formation of AMPA, but its predictions for trifluralin and metazachlor were correct. The simulation of herbicides and AMPA distribution in the soil profile was satisfactory, but the mobility of trifluralin and metazachlor was slightly underestimated, probably because PRZM ignores preferential flow. In general, data from the laboratory allowed an acceptable parameterization of the model, as indicated by goodness-of-fit indices. CONCLUSION: Because of the detection of AMPA in the deep soil layer, the replacement of both trifluralin and metazachlor with glyphosate might not contribute to decreasing environmental contamination by herbicides. PRZM may be used to evaluate and to compare other weed control strategies for herbicide-resistant as well as non-resistant crops.     

Persistence and metabolism of dinitroaniline herbicides in soils

The persistence, binding, and metabolism of six dinitroaniline herbicides, including trifluralin, profluralin, dinitramine, butralin, fluchloralin, and chlornidine, added to Matapeake silt loam were determined after 3, 5, and 7 months. Dinitramine was rapidly degraded during the first 5 months, while butralin and chlornidine were less persistent than fluchloralin, profluralin, and trifluralin after 7 months. The latter three herbicides were similar in persistence and binding properties. The parent herbicide was the major extractable product detected in soil at each sampling time. Degradation products were identified by cochromatography on thin-layer plates, retention times on gas-liquid and high-pressure liquid chromatography, and mass spectral analysis. Dealkylated and cyclic derivatives of the parent herbicide were detected as metabolites. The cyclic products included benzimidazole derivatives of dinitramine, trifluralin, and fluchloralin; a morpholine derivative of chlornidine; and a quinoxaline derivative of fluchloralin. A unique metabolite of butralin was derived from the parent material by the loss of one nitro substituent.     

Environmental fate of herbicides trifluralin, metazachlor, metamitron and sulcotrione compared with that of glyphosate, a substitute broad spectrum herbicide for different glyphosate-resistant crops

The introduction of crops resistant to the broad spectrum herbicide glyphosate, N-(phosphonomethyl)glycine, may constitute an answer to increased contamination of the environment by herbicides, since it should reduce the total amount of herbicide needed and the number of active ingredients. However, there are few published data comparing the fate of glyphosate in the environment, particularly in soil, with that of substitute herbicides. The objective of this study is to compare the fate of glyphosate in three soils with that of four herbicides frequently used on crops that might be glyphosate resistant: trifluralin, alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, and metazachlor, 2-chloro-N-(pyrazol-1-ylmethyl)acet-2',6'-xylidide for oilseed rape, metamitron, 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one for sugarbeet and sulcotrione, 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione for maize. The distribution of herbicides between the volatilized, mineralized, extractable and non-extractable fractions was studied, along with the formation of their metabolites in laboratory experiments using 14C-labelled herbicides, over a period of 140 days. The main dissipation pathways were mineralization for glyphosate and sulcotrione, volatilization for trifluralin and non-extractable residues formation for metazachlor and metamitron. The five herbicides had low persistence. Glyphosate had the shortest half-life, which varied with soil type, whereas trifluralin had the longest. The half-lives of metazachlor and sulcotrione were comparable, whereas that of metamitron was highly variable. Glyphosate, metazachlor and sulcotrione were degraded into persistent metabolites. Low amounts of trifluralin and metamitron metabolites were observed. At 140 days after herbicide applications, the amounts of glyphosate and its metabolite residues in soils were the lowest in two soils, but not in the third soil, a loamy sand with low pH. The environmental advantage in using glyphosate due to its rapid degradation is counterbalanced by accumulation of aminomethylphosphonic acid specifically in the context of extensive use of glyphosate.     

Effects of repeated applications of ten soil-active herbicides on weed population,residue accumulation and nitrification*

Ten herbicides, bromacil, chlorthal-dimethyl, diphenamid, diuron, fluometuron, neburon, prometryne, pyrazon, simazine and trifluralin at two doses were repeatedly sprayed, in autumn and in spring, for 4 consecutive years on non-cultivated, sprinkler-irrigated field plots. Herbicidal effect was assessed at 1–2 month intervals on the natural weed population and after each observation a paraquat + diquat spray destroyed emerged weeds. The response of various weed species to herbicides varied markedly but a herbicide-induced shift in the composition of weed population did not occur, presumably because of the paraquat treatment. The overall phytotoxicity to weeds present was, in decreasing order: diuron, bromacil, simazine, trifluralin, prometryne, neburon, fluometuron, pyrazon, diphenamid, chlorthal-dimethyl. Persistence of herbicides was in decreasing order: diuron = bromacil, simazine, neburon (at higher rate), fluometuron, trifluralin, prometryne. Control produced by pyrazon improved with the number of applications, but that of diphenamid and chlorthal-dimethyl remained weak and short. After repeated applications, the activity of these herbicides increased or remained at similar level, but in no case decreased. Soil samples were taken 5 months after each application and bioassayed. Phytotoxic residues were detected beneath the disturbed top-soil from bromacil, diuron, fluometuron and simazine after the first application, and from neburon after the second application; residues from trifluralin were found in the top soil only after the fifth application. After the seventh spraying, residues of bromacil were found in the 45–60-cm soil layer. Ammonia content in soil samples taken from treated plots after the fourth, sixth and seventh application was generally similar to the untreated control. In these samples, nitrate content appeared to be correlated negatively with remaining weed number; the control thus contained less nitrate than efficient herbicidal treatments. Soil samples taken after the seventh application of bromacil, diuron, fluometuron, neburon and simazine, which contained appreciable residual concentrations, did not show significant differences from control, in an in vitro nitrification test.     

Trifluralin persistence under two different soil and climatic conditions

An investigation of the persistence of trifluralin was conducted as field experiments over a two year period at latitudes 60°N and 70°N respectively, paying special attention to the soil and climatic conditions. These experiments included glasshouse bioassays with Lolium multiflorum. gas-chromatographic residue analyses and qualitative and quantitative studies on soil bacteria. Special attention was devoted to clay minerals as well as to the soil organic matter. 100 g or 500 g of trifluralin a.i. ha^?1 were applied in the spring 1978 with a reapplication on half of the area the following spring (1979). The phytotoxicity of trifluralin appeared more severe on re-treated plots compared with single applications even at approximately equal residue levels. Trifluralin did not seem to have any real influence on the total number of soil bacteria. A qualitative change of the bacterial flora was however observed as a relative increase of non-sporeformers, Gram negatives and Actinomy-cetes and a relative depression of the Coryneform bacteria/Arthrobacter group. Even at a recommended dosage, a carry-over phytotoxicity the following year may occur, especially when the content of organic matter in the soil is low. Care should therefore be taken when using this herbicide on the same field in two successive years. The properties of the soil seemed to exert a greater influence than the climatic factors on the persistence of trifluralin.     

Mobility and persistence of four herbicides in soil of a South Australian vineyard

The use of persistent herbicides has increased the potential for contamination of soil, soil water and groundwater. The mobility, dissipation and fate of four herbicides, norflurazon, oxadiazon, oxyfluorfen and trifluralin, used in South Australian viticulture, have been studied in a typical sand‐over‐clay vineyard soil. Following herbicide application at field rates to plots up‐slope of miniature lysimeters, surface soil and soil water were sampled regularly over the period of annual rainfall. The concentration of each herbicide in the soil cores, surface soil and soil water was determined by GLC‐NPD following solid‐phase concentration procedures where necessary. Oxadiazon dissipated more quickly than the other three herbicides in the soil. Norflurazon was the most mobile of these herbicides in this soil. However all four herbicides were found in the soil water within the first year, though only norflurazon was found in the soil water in the subsequent year. Norflurazon moved laterally to a greater extent than the other herbicides. © 2000 Society of Chemical Industry     

The effect of some herbicides on vesicular-arbuscular endophyte abundance in the soil and on infection of host roots

The effect of the herbicides di-allate, diquat, diuron, paraquat, tri-allate and trifluralin, at a range of application rates from 0.5 to 32 times that recommended by the manufacturers, on vesicular-arbuscular (V-A) endophyte spore abundance in the soil and on infection of wheat roots was investigated in field and glasshouse experiments. Paraquat and diquat had no measurable effect on V-A endophyte spore abundance. There was a slight trend to lower V-A endophyte spore numbers at high rates of application of di-allate and tri-allate but no trend for the other chemicals. Infection intensity (% root length infected) declined at high rates of di-allate and led to lower mycorrhizal root weights. The phosphorus content of the shoots was also reduced by di-allate. High doses of di-allate, diuron, tri-allate and trifluralin reduced most parameters of plant growth more than mycorrhizal parameters. It is therefore concluded that at normal application rates these chemicals are unlikely to affect adversely endomycorrhiza formation or function.     

The effect of herbicides on respiration and transformation of nitrogen in two soils II. Dalapon, pyrazone and trifluralin

The effects of dalapon, pyrazone and trifluralin at 100 ppm on carbon dioxide evolution and nitrogen transformation in two soils have been investigated in the laboratory. None of the herbicides had any adverse effects on carbon dioxide evolution or mineralisation of nitrogen. In Triangle soil (organic carbon 3.9%, pH 5.4) dalapon and pyrazone inhibited nitrification for at least 3 weeks. In Boddington Barn soil (organiccarbon 1.5%, pH 6.6) this effect was not observed. Dalapon degraded rapidly during the first 6 weeks, but pyrazone and trifluralin were more persistent.     

Design and synthesis of N-(2,4=difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (diflufenican), a novel pre- and early post-emergence herbicide for use in winter cereals

The pre- and early post-emergence herbicidal activity of diflufenican, a novel herbicide, is reported and attention is drawn to its ability to control important weeds in winter cereals, including Galium aparine, Veronica hederifolia, Veronica persica and Viola arvensis, which are resistant to substituted-urea herbicides. The synthesis of a series of related compounds is described and the relationship between structure and activities against a range of plant species is examined in respect of changes in the phenyl, phenoxy and pyridine rings. The design and synthesis of a small number of compounds combining the best patterns of substitution in each of the rings is described. The resulting optimisation of herbicidal activity in the series is reported, together with field trial results comparing the herbicidal efficacy, crop selectivity and soil persistence of the most active structures.     

生物源除草活性物质开发及应用研究进展

生物源除草剂是一种环境友好型除草剂,是未来除草剂的发展方向之一。本文从生物源除草剂应用的角度出发,综述了历年来国内外生物源除草活性物质在除草领域的研究进展,对生物源除草活性物质及其衍生物的开发和应用现状进行了系统的归纳和总结。其中植物源除草活性物质包括松科、桃金娘科、芸香科、唇形科和菊科等植物的提取物、分泌物和化学改性衍生物;微生物源除草活性物质包括真菌、细菌、放线菌、病毒和它们的次生代谢产物。本文可为生物源除草剂的开发和应用提供一定参考。     

PERSISTENCE OF PHYTOTOXIC RESIDUES OF TRIAZINE HERBICIDES IN SOIL

Summary. A bioassay technique for the determination of phytotoxic residues of triazine herbicides and monuron in soil from field plots is described. The effect of a dilution series with untreated soil on shoot growth of Italian ryegrass ( Lolium multiflorum Lam.) is compared with that in a corresponding assay at the lime of application of the herbicide. This method was used to compare the persistence of residues of simazine, propazine, prometon and monuron, and to compare persistence in 3 years and in three soil types. The time required for disappearance of 80% of the activity following application of 2 lb/ac of simazine varied from 7 to 27 weeks, according to the year. Prometon was the most persistent of the triazines tested.
Persistance de résidus phyloloxiques d'herbicides à base de triazines dans le sol     

11种除草剂对小麦田恶性杂草阿拉伯婆婆纳的防除效果

针对我国黄淮海冬麦部分区域恶性杂草阿拉伯婆婆纳,开展了田间茎叶处理除草剂筛选试验,并比较了不同施药时期防效的差异.结果表明,防除阿拉伯婆婆纳,越冬前施用除草剂的防效优于返青期施药,可选择10％苯磺隆可湿性粉剂27.00 g/hm2,或56％2甲4氯钠可溶粉剂1 260.00 g/hm2,或40％唑草酮水分散粒剂36.0...     

Synthesis and herbicidal potential of substituted aurones

BACKGROUND: With the objective of exploring the herbicidal activity of substituted aurones, a series of 4,6‐disubstituted and 4,5,6‐trisubstituted aurones were synthesised, and their herbicidal activities against Brassica campestris L. and Echinochloa crusgalli (L.) Beauv. were evaluated in laboratory bioassays. Effects of some of the compounds were evaluated on seed germination. The most active compounds in the laboratory were evaluated in the greenhouse. RESULTS: The compounds were characterised by ¹H NMR, ¹³C NMR and HRMS; some of them were further identified by IR. A (Z)‐configuration was assigned to the aurones, based on spectroscopic and crystallographic data. Bioassay results of root growth showed that the aurones had a moderate herbicidal activity against the dicotyledonous plant Brassica campestris. (Z)‐2‐Phenylmethylene‐4,6‐dimethoxy‐3(2H)‐benzofuranone(6o) was the most active compound, with 81.3 and 88.5% inhibition at 10 and 100 µg ml^?1 respectively, equal to the activity of mesotrione. Some of the aurones possessed some inhibition of germination on several plant species. For glasshouse tests, the substituted aurones had lower herbicidal activity than metolachlor and mesotrione. CONCLUSION: It is possible that aurone derivatives, which possess structures different from those of the commercial herbicides, may become novel lead compounds for the development of herbicides against dicotyledonous weeds with further structure modification. Copyright © 2012 Society of Chemical Industry     

Pre-sowing herbicides in irrigated cotton (Gossypium barbadense L.) and ground nut (Arachis hypogaea L.) in the Sudan. I. Weed control and crop yields achieved with trifluralin and benfluralin.

Trifluralin in cotton and benfluralin in groudnut. incorporated pre-planting. gave satisfactory control of grass weeds and increased crop yields substantially. Oxadiazon as a pre-planting treatment did not give satisfactory additional control of dicotyledons resistant to the first two herbicides. A post-sowing mechanical ridging operation controlled some herbicide resistant weeds, but its effects depended on timing, weed species and growing conditions. Supportive hand weeding of resistant weeds (mainly dicotyledons) was most effective 4 weeks after crop emergence. Crop yields similar to clean weeded controls were achieved by combining trifluralin or benfluralin with moderate supportive hand weeding and re-ridging. Herbicide applications could be made several months before crop planting during the dry season, giving more effective use of spray equipment and operatives. Delays of up to 24 hours between spraying and incorporation by normal cultivation could be tolerated without loss of herbicidal activity.     

A comparison of crop and non-crop plants as sensitive indicator species for regulatory testing

The effectiveness of regulatory non-target plant testing using crop species to predict the phytotoxicicity of herbicides to non-crop species was evaluated for eleven herbicides. These herbicides were representative of eight chemical classes and six modes of action. Data for non-crop plants from pre-emergence and post-emergence efficacy screening studies were compared with those for the most sensitive crop species defined by regulatory tests conducted to meet US EPA requirements. Testing under pre-emergence conditions for ten compounds indicated that for five of the compounds (K-815910, trifluralin, pyridyloxy A, pyridyloxy B and cyanazine), the most sensitive crop species was more sensitive than all the non-crop species evaluated. For metsulfuron-methyl, chlorimuron-ethyl, hexazinone and bromacil, only one of the non-crop species evaluated was more sensitive than the most sensitive crop species from regulatory tests. Data for the tenth compound, chloroacetamide, showed that four of 32 non-crop species tested in efficacy screens had at least one rate at which greater visual effects were observed than were observed for the most sensitive crop response in a regulatory test. The results of post-emergence exposure comparisons for five of the compounds (pyridyloxy A, cloransulam-methyl, chlorimuron-ethyl, cyanazine and hexazinone) indicated that the most sensitive crop species were more sensitive than all the non-crop species evaluated. Data for pyridyloxy B, metsulfuron-methyl and bromacil indicated that only one of the non-crop species evaluated was more sensitive than the most sensitive crop species. For trifluralin, three of the eight non-crop species were more sensitive than the most sensitive crop species. Data for K-815910 indicated that four of the fourteen non-crop species tested were marginally more sensitive than the most sensitive crop, but were within the same range of sensitivity. These results indicate that the current regulatory test batteries and methods using crop species effectively provide suitable sensitive indicator plants for the eleven diverse herbicides evaluated. This comparison indicates that crop species sensitivity to test substances is likely to be representative of non-crop herbaceous species response, regardless of chemical class, mode of action and magnitude or route of exposure.     

氟乐灵等5种除草剂对棉花枯萎病发生及棉花抗病性的影响

在温室盆栽条件下,研究了5种常用除草剂(氟乐灵、除草醚、丁草胺、扑草净和草甘膦)对棉花枯萎病发生及棉花抗病性的影响。结果表明:施用除草剂同时接种病原,氟乐灵播前土壤处理减轻了浙肖棉1号(感病)和中棉12号(抗病)棉花苗期枯萎病的发生;而其他4种除草剂则不同程度地促进了苗期枯萎病的发生。播前土壤药剂处理,出苗1周后接种病原,氟乐灵和除草醚提高了棉花对枯萎病的抗性,扑草净降低了棉花的扰病性,而草甘膦则不影响棉花的抗病性。     

Soil persistence experiments with [14C]2,4-D in herbicidal mixtures, and field persistence studies with tri-allate and trifluralin both singly and combined

The persistence of [¹⁴C]2,4-D at a rate equivalent to 1 kg/ha was studied in the laboratory on a heavy clay and a sandy loam at 85%of field capacity and 20°C both alone and in the presence of 1 kg/ha dicamba, dichlorprop, difenzoquat, TCA, and 2,4,5-T. The persistence of 2,4,5-T was also monitored in both soils under the same conditions in the presence and absence of [¹⁴C]2,4-D. All soils were extracted at weekly intervals using aqueous acidic acetonitrile and analysed for [¹⁴C]2,4-D remainining radiochemical techniques. The extracts containing 2,4.5-T were additionally analysed gas chromatographically for that herbicide. In each soil type the half-life of the 2,4-D was similar regardless of whether applied singly or in combination with the five herbicides tested. Similarly, [¹⁴C]2,4-D did not affect the breakdown of 2,4,5-T in either soil type. The persistence of tri-allate (1·5 kg/ha) and trifluralin (0·75 kg/ha) both singly and in combination were compared using small field plots at two locations in Saskatchewan. Applications were made during May of 1977 and 1978 and the plots were sampled and analysed for herbicide(s) remaining after 10 and 20 weeks, respectively. The results indicate that within experimental error the loss of both tri-allate and trifluralin from the plots treated with the mixture was the same as from plots treated with the individual compounds.     

Behavior and persistence in soil of benefin

The phytotoxicity of benefin, as assessed by sorghum on various soils and soil mixtures, was significantly correlated with the organic matter content but not with the clay or lime content of the soils. After 1 month of incubation no significant activity remained from 2 ppm benefin, and after 2 months only slight activity remained from 4 ppm. Benefin was less persistent than trifluralin and more persistent than nitralin.     

Persistence studies with [14C] 2,4-D in soils previously treated with herbicides and pesticides

The persistence of [¹⁴C] 2,4-D at a rate equivalent to 1 kg/ha was compared under laboratory conditions in samples of heavy clay, sandy loam, and clay loam at 85% of field capacity moisture and 20 ± 1°C which had either received no pre-treatment, or had been pre-treated for 7 days at the 2 μg/g level with the herbicides benzoylprop-ethyl, diclofop-methyl, dinitramine, flamprop-methyl, nitrofen, picloram, tri-allate, trifluralin, and a combination of tri-allate and trifluralin. The breakdown of [¹⁴C] 2,4-D was also studied in the same soils that had similarly received pre-treatments of 2 μg/g of the cereal seed dressing Vitaflo-DB, the insecticide, malathion, and a combination of Vitaflo-DB and malathion. In each soil type, the half-life of the 2,4-D was similar regardless of whether the soil had, or had not, received any pre-treatment, indicating that none of the chemicals investigated adversely affected the soil degradation of 2,4-D.