Fate of metsulfuron-methyl in soils in relation to pedo-climatic conditions

The dependence of the behaviour of metsulfuron-methyl on soil pH was confirmed during incubations under controlled laboratory conditions with two French soils used for wheat cropping. The fate of [¹⁴C] residues from [triazine-¹⁴C]metsulfuron-methyl was studied by combining different experimen-tal conditions: soil pH (8·1 and 5·2), temperature (28 and 10°C), soil moisture (90 and 50% of soil water holding capacity) and microbial activity (sterile and non-sterile conditions). Metsulfuron-methyl degradation was mainly influenced by soil pH and temperature. The metsulfuron-methyl half-life varied from five days in the acidic soil to 69 days in the alkaline soil. Under sterile conditions, the half-life increased in alkaline soil to 139 days but was not changed in the acidic soil. Metsulfuron-methyl degradation mainly resulted in the formation of the amino-triazine. In the acidic soil, degradation was characterised by rapid hydrolysis giving two specific unidentified metabolites, not detected during incubations in the alkaline soil. Bound residues formation and metsulfuron-methyl mineralisation were highly correlated. The extent of bound residue formation increased when soil water content decreased and was maximal [48 (±4)% of the applied metsulfuron-methyl after 98 incubation days] in the acidic soil at 50% of the water holding capacity and 28°C. Otherwise, bound residues represented between 13 and 32% of the initial radioactivity. © 1998 SCI     

Model Predictions and Field Measurements of Chlorsulfuron Leaching under Non-steady-state Flow Conditions

Model simulations of chlorsulfuron (1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea) leaching in a loamy soil were made with the mechanistic dual-porosity model MACRO. Comparisons were made with a data set obtained in a lysimeter experiment in which leaching was measured during an 11-month period after applying chlorsulfuron at two rates (4 and 8 g ha⁻¹). In this experiment, peak concentrations appeared c.6 months after pesticide application, reaching levels of 14 and 21 ng litre⁻¹ in the low- and high-dose treatments, respectively. These peak concentrations appeared after c.70 mm of accumulated leachate, implying that some of the herbicide was displaced through the soil columns by non-equilibrium flow processes. Model calibration was limited to parameters related to evapotranspiration, water uptake by roots and degradation rates in the subsoil. With this minimum amount of calibration, the model successfully described the leaching pattern of chlorsulfuron, provided that the two-flow domain option in the model was used. Running the model in one-flow domain resulted in considerable underestimates of leaching of chlorsulfuron over the short-term (<1 year). The degradation rate in the subsoil was also found to be critical. It had to be increased about fivefold to match measured chlorsulfuron concentrations in leachate. At such concentrations, 0·012 g ha⁻¹ of chlorsulfuron (0·3% of that applied) was predicted to leach through the soil profile during the 11-month simulation period when the lower dose of the compound was applied.     

Aerobic soil metabolism of metsulfuron-methyl

A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20°C. Both [phenyl-U-¹⁴C]- and [triazine-2-¹⁴C]metsulfuron-methyl were used. The soil was treated with [¹⁴C]metsulfuron-methyl (0.1 mg kg⁻¹) and incubated in flow-through systems for one year. The degradation rate constants, DT₅₀, and DT₉₀ were obtained based on the first-order and biphasic models. The DT₅₀ (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9–11 days, 95% confidence limits) in the non-sterile soil and 20 days (12–32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-¹⁴C] and [triazine-2-¹⁴C]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[[[[[[[(acetylamino)carbohyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[[[[[amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. © 1999 Society of Chemical Industry     

异噁唑草酮在土壤表面光解及在土壤中的降解和淋溶特性

为合理评估除草剂异唑草酮的环境风险,在实验室模拟条件下,研究了异唑草酮在土壤 (红壤土)表面光解以及在不同质地土壤 (潮土、水稻土和红壤土) 中的降解和淋溶特性。结果表明:异唑草酮在土壤表面的光解遵循一级反应动力学方程c_t = 4.23e–0.008t (r = 0.937),半衰期为82.5 h;其在潮土、水稻土和红壤土中的降解均符合一级动力学方程,好氧条件下,异唑草酮在3种土壤中的降解半衰期分别为10.5、43.3和139 h,厌氧条件下的降解半衰期分别为19.4、18.4和158 h;其在潮土、水稻土和红壤土中的淋溶系数 (R_f) 分别为0.417 0、0.083 3和0.083 3。研究表明:异唑草酮在土壤表面光解速率较慢,而在土壤中好氧及厌氧条件下降解速率均较快,残留期短;其在土壤中淋溶性较弱,不易对周围环境及地下水造成污染风险。     

Degradation of [14C]Terbuthylazine and [14C]Atrazine in Laboratory Soil Microcosms

The degradation and formation of major chlorinated metabolites of terbuthylazine and atrazine in three soils (loamy clay, calcareous clay and high clay) were studied in laboratory experiments using molecules labelled with ¹⁴C on the s-triazine ring. Soil microcosms were treated with the equivalent of 1 kg ha^-1 of herbicide and incubated in the dark for 45 days at 20(±1)°C. The quantity of [¹⁴C]carbon dioxide evolved in the soils treated with atrazine was negligible and could not be attributed to mineralization of the parent molecule. The mineralization of terbuthylazine accounted for 0·9–1·2% of the initial radioactivity. In the soils studied, the extrapolated half-lives varied from 88 to 116 days for terbuthylazine and 66 to 105 days for atrazine, with no significant differences for the three soils and the two molecules. The deethyl metabolites of the two s-triazines and the deisopropyl-atrazine metabolite appeared during the incubation in the three soils. The completely dealkylated metabolite was not detected in any of the soils. After 45 days of incubation, the non-extractable soil residues for the high clay, loamy clay and calcareous clay soils represented for terbuthylazine, 33·5, 38·3 and 43·1% and for atrazine, 19·8, 20·8 and 22·3% of the initial radioactivity. © 1997 SCI.     

Chemical hydrolysis of 2-chloro-4,6-bis(alkylamino)-1,3,5-triazine herbicides and their breakdown in soil under the influence of adsorption

The determination of rate constants and the calculation of the activation parameters [activation energy (E_a), free energy of activation(ΔG^≠)and entropy of activation (ΔS^≠)] demonstrated the identity of the reaction kinetics of chemical hydrolysis of the chlorinated triazine herbicides simazine, atrazine, propazine and terbuthylazine. Persistence in soil could be estimated, from the hydrolytic half-life time, only in pH regions where these compounds were also sensitive to chemical hydrolysis. In general, the rate of hydrolysis increased in the presence of soil as the result of a catalysing effect of the soil in their breakdown. When half-lives in soil of these triazine herbicides were compared with adsorption constants, a functional relationship was observed in both soil types; as adsorption increased the half-life in soil also increased.     

Persistence of Chlorpyrifos in Soils under Different Moisture Regimes

Chlorpyrifos is an organophosphorus insecticide used to control insect pests in soil. The fate of chlorpyrifos in soils under different moisture regimes is of interest because application directions specify soil-surface treatments for a number of agricultural and urban pests. Chlorpyrifos was degraded rapidly in all air-dry soils and slightly more slowly in soils at field capacity and/or under submerged conditions. Degradation rates were influenced by clay-catalysed hydrolysis under air-dry conditions and neutral or alkaline hydrolysis under submerged conditions. Degradation was faster in Bellary soil (chromic haplustert) and slower in Chettalli soil (ustic palehumult) under all three moisture regimes. The calculated half-lives ranged from 1·6 to 10·0, 5·2 to 22·0 and 8·7 to 25·1 days under air-dry, field capacity and submergence respectively at an application rate of 10 mg kg^-1. © 1997 SCI.     

Quantitative bioassays for determining residues and availability to plants of sulphonylurea herbicides

A bioassay procedure for quantitative determination of sulphonylurea herbicides is described. Turnips (Brassica rapa) were found very suitable as test plants and gave results within 10 days. Six sulphonylurea compounds were investigated for their activity in three widely differing soils. The potential availability to plants was calculated from the dose-response curves of vermiculite (non-sorptive substrate) and the corresponding ED₅₀-values of the soils. The dose-response relationship (logistic curve) was described by a computer model by a position parameter, the slope of the curve and the minimum and maximum fresh weights of plants. The limit of quantitative detection in the range of ED₃₀ in vermiculite was 0·06 μg 1^?1 for sulfometuron and 1·03 μg 1^?1 for DPX-L5300, methy12-([4-methoxy-6-methyl-1,3,5-triazin-2-yl (methyl)carbamoyl]-sulphamoyl) benzoate. Results with turnips showed that sulfometuron was the most active compound in all substrates (ED₅₀ in vermiculite 0·12 μg 1^?1) followed by chlorsulfuron, metsulfuron-methyl, triasulfuron, DPX-M6316, methyl 3-([(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbamoyl]-aminosulphaphamoyl)-2-thiophenecarboxylate, and DPX-L5300 which had ED₅₀ or 1·98 μg 1^?1, The Horotiu sandy loam soil showed the highest ED₅₀-values and the lowest plant availability for all compounds compared to the other soils. Probit and logistic evaluation methods for deriving dose-response relationships are compared and their applicability is discussed.     

Hydrolysis of triasulfuron,metsulfuron‐methyl and chlorsulfuron in alkaline soil and aqueous solutions

The hydrolysis of triasulfuron, metsulfuron‐methyl and chlorsulfuron in aqueous buffer solutions and in soil suspensions at pH values ranging from 5.2 to 11.2 was investigated. Hydrolysis of all three compounds in both aqueous buffer and soil suspensions was highly pH‐sensitive. The rate of hydrolysis was much faster in the acidic pH range (5.2–6.2) than under neutral and moderately alkaline conditions (8.2–9.4), but it increased rapidly as the pH exceeded 10.2. All three compounds degraded faster at pH 5.2 than at pH 11.2. Hydrolysis rates of all three compounds could be described well with pseudo‐first‐order kinetics. There were no significant differences (P = 0.05) in the rate constants (k, day⁻¹) of the three compounds in soil suspensions from those in buffer solutions within the pH ranges studied. A functional relationship based on the propensity of nonionic and anionic species of the herbicides to hydrolyse was used to describe the dependence of the ‘rate constant’ on pH. The hydrolysis involving attack by neutral water was at least 100‐fold faster when the sulfonylurea herbicides were undissociated (acidic conditions) than when they were present as the anion at near neutral pH. In aqueous buffer solution at pH > 11, a prominent degradation pathway involved O‐demethylation of metsulfuron‐methyl to yield a highly polar degradate, and hydrolytic opening of the triazine ring. It is concluded that these herbicides are not likely to degrade substantially through hydrolysis in most agricultural alkaline soils. © 2000 Society of Chemical Industry     

Degradation of mecoprop at different concentrations in surface and sub-surface soil

Biodegradation of [ring-¹⁴C] mecoprop (2-(4-chloro-2-methylphenoxy)propionic acid) was determined in surface and sub-surface soil at concentrations of 0·0005, 0·05, 0·5, 5, 50, 500, 5000 and 25000 mg kg^-1. The kinetics of mineralisation were evaluated from the mineralisation rates as a function of time and by non-linear regression analysis. In the sub-surface soil, degradation was 6–8 times slower than in surface soil, but the shape of the curves was the same in both layers. At concentrations between 0·0005 and 0·5 mg kg^-1, in both surface and sub-surface soil, degradation was initially zero-order followed by first-order kinetics. At 5 to 500 mg kg^-1 in surface soil and 5 to 50 mg kg^-1 in sub-surface soil the degradation rate was initially either constant or decreasing followed by exponential degradation indicating increasing populations of mecoprop decomposers in the soil. At 5000 and 25000 mg kg^-1 in the surface soil and at 500, 5000 and 25000 mg kg^-1 in the sub-surface soil, the degradation was negligible, as determined by the percentage [¹⁴C] carbon dioxide evolved. By non-linear regression, the three-half order model was found to describe the mineralisation. © 1998 SCI     

Spatial variability in the degradation rates of isoproturon and chlorotoluron in a clay soil

Thirty separate soil samples were taken from different locations at the Brimstone farm experimental site, Oxfordshire, UK. Incubations of isoproturon under standard conditions (15 °C; ?33 kPa soil water potential) indicated considerable variation in degradation rate in the soil, with the time to 50% loss (DT₅₀) varying from 6 to 30 days. These differences were confirmed in a second comparative experiment in which degradation rates were assessed in 11 samples of the same soil in two separate laboratories using an identical protocol. There was a significant negative linear relationship (r²= 0.746) between the DT₅₀ values and soil pH in this group of soils. In a third experiment, degradation rates of the related compound chlorotoluron were compared with those of isoproturon in 12 separate soil samples, six of which had been stored for several months, and six of which were freshly collected from the field. Degradation of both herbicides occurred more slowly in the stored samples than in the fresh samples but, in all of them, chlorotoluron degraded more slowly than isoproturon, and there was a highly significant linear relationship (r²=0.916) between the respective DT₅₀ values.     

Degradation of guanidated amine acetates

The active ingredient of the fungicide ‘Panoctine’ is a standardised mixture of guanidated amine acetates (GTA). This mixture was degraded in German standard soils with half-lives of 400–600 days. GTA dressed on to wheat seed at 0.75 g kg^? had a half-life of 20 days when seed was incubated in Petri dishes at 25°C and of 80 days on seed sown in pots of soil stored outside. These results demonstrate a substantial influence of the test system on the degradation times of guanidated amine acetates.     

Photolytic versus microbial degradation of clomazone in a flooded California rice field soil

BACKGROUND: Clomazone is a popular herbicide used on California rice fields and exhibits rapid anaerobic microbial degradation (t_1/2 = 7.9 days). To test the potential of direct and indirect photolytic degradation as a cofactor in the overall degradation rate, sacrificial time‐series microcosms were amended with water, non‐sterilized soil + water and sterilized soil + water. Clomazone was added to each microcosm, which was then exposed to natural and artificial sunlight over 35 days. Water and acetonitrile extracts were analyzed for clomazone and metabolites via LC/MS/MS. RESULTS: The calculated pseudo‐first‐order degradation rate constants (k) were k_water = 0–0.005 ± 0.003 day^?1, k_sterile = 0–0.005 ± 0.003 day^?1 and k_non?sterile = 0.010 ± 0.002–0.044 ± 0.007 day^?1, depending on light type. The formation of ring‐open clomazone, a microbial metabolite, correlated with clomazone degradation. Trace amounts of 5‐hydroxyclomazone (m/z = 256 → 125), aromatic hydroxyclomazone (m/z = 256 → 141) and an unknown product (m/z = 268 → 125) were observed. CONCLUSIONS: The photolytic degradation rate depends on both light type and the quality of the chromophores that induce indirect photolysis. Microbial degradation was found to be sensitive to temperature fluctuations. Overall, microbes are shown to be more detrimental to the environmental fate of clomazone than photolysis. Copyright © 2012 Society of Chemical Industry     

Aerobic soil metabolism of flupyrazofos

To elucidate the fate of flupyrazofos [O,O-diethyl O-(1-phenyl-3-trifluoromethyl-5-pyrazoyl)phosphorothionate] in soil, an aerobic soil metabolism study was carried out for 60 days with [¹⁴C]flupyrazofos applied at a concentration of 0·38 μg g^-1 to a loamy soil. The material balance ranged from 103·5% to 86·9% and the half-life of [¹⁴C]flupyrazofos was calculated to be 13·6 days. The metabolites identified during the study were 1-phenyl-3-trifluoromethyl-5-hydroxypyrazole (PTMHP) and O,O-diethyl O-(1-phenyl-3-trifluoromethyl-5-pyrazoyl)phosphate (flupyrazofos oxon), with maximum levels of 9·8% and 1·6% of applied radiocarbon, respectively. Evolved [¹⁴C]carbon dioxide accounted for up to 5·3% of applied radiocarbon and no volatile products were detected during the study. Non-extractable ¹⁴C-residue reached 31·6% of applied material at 60 days after treatment and radiocarbon was distributed almost evenly in humin, humic acid and fulvic acid fraction. © 1998 Society of Chemical Industry     

Phytotoxicity and persistence of chlorsulfuron as affected by activated charcoal

Two bioassay procedures, using petri-dishes and pots, based on the root growth of pregerminated maize were used to study the residual phytotoxicity of chlorsulfuron under field conditions. Both bioassay procedures appeared to be equally reproducible and sensitive with residues of chlorsulfuron being detectable from 0·25 to 10·0 ng g^-1. The results indicated that persistence, movement and phytotoxicity increased with increasing rate of chlorsulfuron, but persistence of the herbicide was shorter in wet compared to dry field conditions. As little as 1 g a.i. ha^-1 of incorporated chlorsulfuron under warm and dry field conditions caused a stunting effect on maize plants (Hybrid F₁, Damon) and reduced yield by 53% compared to untreated control plants; while 5·0 and 10·0 g a.i. ha^-1 of incorporated chlorsulfuron killed all maize plants. However, under wetter field conditions, incorporated chlorsulfuron at 1·25, 2·5 and 5·0 g a.i. ha^-1 caused a stunting effect on maize plants (Hybrid F₁, ARIS) and decreased yield by 16, 57 and 92%, respectively, compared to untreated control. Incorporation of 50 kg ha^-1 of activated charcoal inactivated completely chlorsulfuron incorporated at 1·25 and 2·5 g a.i. ha^-1 and did not affect yield of maize compared to untreated control. Higher rates of activated charcoal such as 100 and 200 kg ha^-1 also inactivated chlorsulfuron applied at 1·25–5·0 g a.i. ha^-1 and did not affect grain yield of maize. Phytotoxicité et persistance du chlorsulfuron Deux méthodes d'essais biologiques, à savoir en boîte de Petri ou en pot, Basées sur la croissance des racines de maïs prégermé ont été utilisées pour étudier la phytotoxicité résiduelle du chlorsulfuron en conditions de plein champ. Les deux méthodes sont également reproductibles et sensibles à des niveaux de détection pour les résidus de chlorsulfuron de 0,25 à 10 ng g^-1. Les résultats montrent que la persistance et la phytotoxicité augmentent avec des doses croissantes de chlorsulfuron, mais la persistance est plus courte dans des conditions de plein champ humides que séches. Une dose aussi faible que 1 g de matiére active ha^-1 de chtorsulfuron incorporé en conditions chaudes et séches a causé un effet retard sur les plants de maïs (hybride F₁, Damon) et a réduit de 53% le rendement par rapport au témoin non traité; des doses de 5 à 10 g de matiére active ha^-1 de chlorsulfuron incorporé ont tué tous les pieds de maïs. Cependant, en conditions plus humides, le chlorsulfuron incorporéà 1,25, 2,5 et 5 g de matiére active ha^-1 a causé un effet retard sur le maïs (hybride F₁ ARIS) et a réduit le rendement par rapport au témoin non traité respectivement de 16, 57 et 92%. L'incorporation de 50 kg ha^-1 de charbon actif a complément inactive le chlorsulfuron incorporéà 1,25 et 2,5 g de matiére active ha^-1 et n'a pas eu de répercussion sur le rendement par rapport au témoin non traité. Des doses plus élevées de charbon actif comme 100 et 200 kg ha^-1 ont inactivé le chlorsulfuron appliquéà 1,25–5 g matiére active ha^-1et n'ont pas affecté le poids en grain du maïs. Ueber die Beeinflussung von Phytotoxizität und Wirkungsdauer von Chlorsulfuron durch Aklivkohle Zum Studium der Residualwirkung von Chlorsulfuron unter Feldbedingungen wurden zwei Bioassaymethoden, eine in Petrischalen, die andere in Töpfen, eingesetzt. Beide Methoden basierten auf dem Wurzelwachstum von vorgekeimtem Mais. Es zeigte sich, dass beide Versuchsverfahren in gleichem Masse reproduzierbar und empfindlich und in der Lage sind Rückstände von 0,25–10,0 ng g^-1 nachzuweisen. Mit steigender Chlorsulfurondosis wurde eine zunehmende Phytotoxizität, Persistenz und Mobilität des Herbizids festgestellt. Die Persistenz war unter feuchten Feldbedingungen kürzer als bei Trockenheit. Bis zu einer unteren Grenze von 1,0 g a.i. ha^-1 verursachte inkorporiertes Chlorsulfuron, unter trockenen und warmen Feldbedingungen an Mais (Hybride F₁, Damon) Wachstumshemmungen und Erntereduktionen von 53%, verglichen mit unbehandelten Kontrollpflanzen. Unter feuchteren Bedingungen, jedoch, hatten 1,25, 2,5 and 5,0 g a.i. ha^-1 eingearbeitetes Chlorsulfuron an Mais (Hybride F₁ ARIS) Wachstumshemmungen und Ernteverluste von 16, 57 und 92% zur Folge. Die Einarbeitung von 50 kg ha^-1 Aktivkohle inaktivierte 1,25 g und 2,5 g ha^-1 inkorporierles Chlorsulfuron vollständig und hatte keinerlei negative Auswirkungen auf die Maisernte, im Vergleich zu unbehandelten Kontrollen. Höhere Mengen von Aktivkohle, wie 100 und 200 kg ha^-1, inaktivierten auch Chlorsulfuronmengen von 1,25–5 g ha^-1 und hatten keinen Einfluss auf den Kömerertrag.     

Aerobic Metabolism of Flupropacil in Sandy Loam Soil

The aerobic soil metabolism of [¹⁴C]flupropacil (isopropyl 2-chloro-5-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoate) was determined in microbially active, sieved (2-mm) sandy loam soil with a soil moisture content of 75% at 1/3 bar. The soil was treated with [¹⁴C]flupropacil at 0·5 mg kg⁻¹ (twice the field use rate) and placed in incubation flasks connected to a series of traps (50 g litre⁻¹ NaOH, 0·5M H₂SO₄, ethylene glycol) and incubated at 25(±1)°C. Soil was sampled at 0, 3, 9, 20, 30, 48, 76, 120, 181 and 238 days of aerobic incubation. Volatiles were collected once every two weeks and on the day of soil sampling. Flupropacil metabolized with a half-life of 79 days under aerobic conditions. The major metabolite was flupropacil acid which accounted for up to 69·1% of the initially applied radioactivity at Day 238. Each of the two minor metabolites detected at the end of the study accounted for less than 0·5%. One of the minor metabolites was identified as C4242 acid (2-chloro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid). Only a negligible portion (less than 0·3%) of the applied flupropacil was mineralized to [¹⁴C]carbon dioxide. Extractable radioactivity ranged from 78·9% to 95·5%, with bound residues accounting for 3·2%–23·4%. The material balance ranged from 91·6% to 104·4%.     

Behaviour of metamitron and hydroxy-chlorothalonil in low-humic sandy soils

The behaviour of the herbicide metamitron and of the main transformation product, hydroxy-chlorothalonil (HTI), of the fungicide chlorothalonil was studied to assess the risk of leaching from low-humic sandy soil. The adsorption of metamitron corresponded to a K_om value of about 60 dm³ kg⁻¹ (moderate adsorption). The half-life of metamitron in soil at 15 °C was only three days, presumably due to adaptation of the micro-organisms. In the autumn, the residue of metamitron in the soil profiles corresponded to less than 1% of the cumulative dosage. The half-life of chlorothalonil at 15 °C was about 12 days and about 45% of it was transformed to HTI. The adsorption of HTI to the soils corresponded to a K_om value of 260 dm³ kg⁻¹. The incubation study (15 °C) showed the transformation of HTI in the soils to be very slow. The amounts of HTI remaining in the soil profiles in the autumn corresponded to 4 and 16% of the cumulative dosage of chlorothalonil. In winter, the HTI residue decreased by 40% relative to the autumn level. Occasionally, HTI could be detected in the upper ground-water level (at a depth of about 1 m), at an average concentration of 0.1 to 0.2 µg dm⁻³. © 1999 Society of Chemical Industry     

Adsorption, transport and degradation of fipronil termiticide in three Hawaii soils

BACKGROUND: The behavior of the termiticide fipronil in soils was studied to assess its potential to contaminate ground and surface water. This study characterizes (1) adsorption of fipronil in three different soils, (2) transport of fipronil through leaching and runoff under simulated rainfall in these soils and (3) degradation of fipronil to fipronil sulfide and fipronil sulfone in these soils. RESULTS: The adsorption experiments showed a Freundlich isotherm for fipronil with K_oc equal to 1184 L kg^?1. In the leaching experiments, the concentration of fipronil and its metabolites in leachate and runoff decreased asymptotically with time. The concentration of fipronil in the leachate from the three soils correlated inversely with soil organic carbon content. The degradation experiment showed that the half‐life of fipronil in the soils ranged from 28 to 34 days when soil moisture content was 75% of field capacities, and that 10.7–23.5% of the degraded fipronil was transformed into the two metabolites (fipronil sulfide and fipronil sulfone). CONCLUSION: Fipronil showed large losses through leaching but small losses via runoff owing to low volumes of runoff water generated and/or negligible particle‐facilitated transport of fipronil. The half‐life values of fipronil in all three soils were similar. Copyright © 2011 Society of Chemical Industry     

Sorption–desorption of 'aged' isoxaflutole and diketonitrile degradate in soil

Isoxaflutole is a relatively new herbicide used for weed control in maize. The objective of this research was to increase the understanding of the behaviour and environmental fate of isoxaflutole and its diketonitrile (DKN) degradate in soil, including determination of the strength of sorption to soil and whether sorption is affected by ageing. In sandy loam (SL) and silty clay (SiCl) soils, ¹⁴C‐isoxaflutole was found to dissipate rapidly after application to soil; recovery ranged from ～42% to 68% at week 0, and recovery had decreased to <10% at week 12. Decreases in ¹⁴C isoxaflutole residues over time in SL and SiCl soils are consistent with hydrolysis of isoxaflutole and formation of bound DKN residues in the soil. DKN recovery from freshly treated SiCl and SL soils was 41% to 52%. After a 12‐week incubation in SL soil at pH 7.1 and 8.0, recoveries were similar, ～40%. However, at week 12 in SL soil pH 5.7, DKN recovery decreased to ～28%. DKN recovery in SiCl soil at week 12 was <10%. Increases in sorption of DKN in SL at pH 5.7 and SiCl soil over time indicate that the DKN degradate is tightly bound to the soil and sorption is affected by soil pH and soil type. Sorption of ¹⁴C‐DKN in the SiCl soil more than doubled with ageing compared with the lower K_d sorption coefficient values of the SL soils. In the SiCl soil at time 0, the K_d was 0.6; at 1 week, K_d increased to 2; and at the end of the 12‐week incubation period, K_d was 4.5. This strong binding of DKN to the soil may be due to chelate formation in the interlayer of the clay.     

Studies on photodegradation of chlorimuron-ethyl in soil

Photolysis of chlorimuron-ethyl was studied on a soil surface under sunlight and UV light. Eight photoproducts were isolated and characterised by spectroscopic methods. Major photoproducts are formed by cleavage of the sulfonylurea bridge and minor products are formed via dechlorination, hydrolysis and cyclisation. The rates of photodegradation of chlorimuron-ethyl on different soils followed first-order rate kinetics, with half lives of 22·3 h, 9·4 h, 4·9 h (UV) and 20·7 days, 11·1 days and 11·1 days (sunlight) for alluvial, red and laterite soils, respectively. The differences in rates of photodegradation were dependent upon the soil pH. © 1997 SCI